In order to work efficiently and safely with a chemical compound, knowing its properties, applications, and risks involved is essential. 1-Bromobutane is an organic compound which has wide applications in the pharmaceutical, agrochemical, and laboratory research industries. As with all other chemicals, working with 1-Bromobutane demands understanding of its chemical properties and safety measures as outlined in its Safety Data Sheet (SDS). This guide aims to provide 1-Bromobutane’s essential information including its properties, uses, and safety instructions while focusing on the most important aspects to pay attention to. This information will be helpful to anyone whether a researcher, chemist, or industrial professional, so they will be able to handle 1-Bromobutane properly and safely.
What is the Property of 1-Bromobutane?
1-Bromobutane is a colorless to light yellow liquid with the molecular formula C4H9Br. Its boiling point is approximately 101 °C (214 °F) and is slightly soluble in water, although it dissolves effortlessly in organic solvents. Like 1-bromobutane, it is also flammable and has a strong pungent odor.
Physical Properties of 1-Bromobutane
1-Bromobutane has a number of noteworthy physical properties. Its molecular weight is 137.02 g/mol, and it is a clear to pale yellow liquid. The compound’s melting point is roughly -112 °C (-169.6 °F) and boiling point is 101 °C (214 °F), thus it can be considered volatile at room temperature. 1-Bromobutane has a density of 1.276 g/cm³ at 20 °C (68 °F), which is greater than water.
1-Bromobutane’s solubility in water is limited to a mere 0.49 g/L at 25 °C (77 °F), where it can be classified as non-polar. However, 1-Bromobutane will readily dissolve in organic solvents such as ethanol, ether, and benzene. At room temperature, the refractive index of 1-bromobutane ranges from 1.438 to 1.440, which describes the angle at which light passing through it is bent. Furthermore, 1-bromobutane has a flash point of 23 °C (73 °F), demonstrating its flammable nature and the need to store and handle it under strict regulated measures.
These reasons explain why 1-Bromobutane is extensively embraced in organic synthesis. Although it is flammable and hazardous, this compound is still used widely.
How Does 1-Bromobutane React With Other Chemicals?
1-Bromobutane is a primary alkyl halide and is actively involved in many different chemical reactions which makes it easy to use in organic synthesis as a reagent. One remarkable reaction is the nucleophilic substitution reaction where one of the bromine atoms is replaced by a nucleophile. For instance, 1-Bromobutane can be treated with sodium hydroxide (NaOH) in elevated temperatures where an SN2 reaction will transform it into butanol. Such reactions exemplify its utility in the production of alcohols and other derivatives.
Moreover, 1-Bromobutane is involved in the preparation of organometallic reagents: butyl magnesium bromide, which is a reagent in Grignard reactions. Grignard reagents are essential in the construction of carbon to carbon bonds and complex molecules. For example, 1-Bromobutane can be reacted with magnesium in dry ether solvent to create this important intermediate.
With exposure to heat of any kind, or flames, it can decompose while simultaneously releasing toxic fumes such as hydrogen bromide (HBr). This highlights the need for safe handling of the compound during reactions involving heat. The different conditions of 1-Bromobutane allow for its use under a variety of situations, making it an ideal compound for industrial and laboratory use.
Applications and Uses of 1-Bromobutane in Organic Synthesis
It is well known that 1-bromobutane can be used as an alkylating agent in organic synthesis. It’s widespread use in grading reagents can be attributed to its high reactivity as well as its capacity to form carbon-carbon bonds. It can undergo reaction with Magnesium in dry ether to form butylmagnesium bromide . This intermediate reagent is pivotal for a variety of reactions, especially in the synthesis of alcohols, acids and other complex organic molecules.
The most recent 1-Bromobutane studies demonstrate increasing usage in the pharmaceutical and agrochemical industries. As indicated by a recent survey, there is growth in the 1-Bromobutane industry as it is increasingly needed in the manufacture of active pharmaceutical ingredients, critical components in a drug for its synthesis. For example, 1-Bromobutane is crucial in the building block used in the thermic development of certain therapeutic agents, which supports its use in large scale industrial reactions. Additionally, these researches assert that 1-Bromobutane plays a pivotal role in agrochemicals for the effective synthesis of pesticides and herbicides.
Also, laboratory studies indicate that 1-Bromobutane may be used in the preparation of ionic liquids, a new class of compounds that have low volatility, are thermally stable, and can be used as green solvents. These pointers indicate its role in the development of green chemistry. At this point, it is essential to highlight the fact that while its uses are numerous, its practical reliability is still a concern, especially because of its possible toxicity and the formation of dangerous substances like hydrogen bromide during decomposition. A careful strategy relating to controlled storage would be needed to minimize a number of risks in the industry and laboratory.
How Can You Ensure Safety Information When Handling 1-Bromobutane?
- Use Proper Protective Equipment: Wear gloves and goggles, along with a lab coat, to reduce skin and eye contact to a minimum.
- Work in a Well-Ventilated Area: Avoid inhalation of vapors by using fume hoods.
- Store Appropriately: 1-bromobutane should be stored in a cool and dry place. The container must be tightly sealed to prevent ingress of vapours and protected from heat sources. Also, the container should not be stored near incompatible materials.
- Follow Disposal Guidelines: 1-bromobutane and contaminated materials must be disposed of in accordance with local hazardous waste regulations.
- Be Prepared for Emergencies: In case of accidental exposure, exposure to hazardous vapours or spillage, safety equipment such as eyewash stations and spill kits should be kept on hand, ready for use.
Understanding the Hazard Class of 1-Bromobutane
Under the Globally Harmonized System of Classification and Labeling of Chemicals (GHS), 1-bromobutane is marked as a chemical of concern. Each GHS hazard class and attribute is interconnected, covering the substance’s physical and environmental dangers, potential health effects, and its emissions profile. Important summary info includes:
- Flammable Liquid (Category 2): 1-Bromobutane is classified as a flammable chemical. As with many brromobutane compounds, 1-bromobutane has a low flash point. Its flash point is approximately 25 degrees celsius (77 degrees Fahrenheit). Like other bromomethanes, 1-bromobutane ignites readily when exposed to flame or elevated temperatures.
- Skin and Eye Irritation (Category 2 and 2A): Skin exposure can result in the irritation of skin and eyes. Repeated exposure may cause increased irritation or dermatitis.
- Specific Target Organ Toxicity – Single Exposure (Category 3): Inhalation of the vapors can cause irritation and dulling of the respiratory track, as well as possible cough, sleepiness, and dizziness surfacing.
- Aquatic Toxicity (Acute and Chronic – Category 2): 1-Bromobutane is deemed hazardous for the environment, especially for water ecosystems, as it is believed to pose danger to living creatures in the water. When entering waters, it has the ability to cause long term damage.
Specific handling procedures and management strategies
Certain strategies of handling and management are very important when working with 1-bromobutane. This chemical should be kept sealed in strong containers and stored in a dry and cool ventilated place that is not exposed to heat or strong light or acids and strong oxidizers. A temperature lower than 30°C (86°F) is preferable due to increased stability of the chemical, hence less possibility of decomposition.
While handling 1-bromobutane, individuals should use appropriate Personal Protective Equipment (PPE) such as chemical gloves, safety goggles, and lab coats to protect the skin and eyes. As recent safety data suggests, the OSHA and other comparable international institutions have recommended exposure limits, but confirmed exposure limits and jurisdictional thresholds differ by region. It is best to check local regulations for exact numbers.
Inhalation of vapors is strictly contraindicated as vapor exposure will result in irritation and even drowsiness. 1-bromobutane requires proper ventilation, including the use of fume hoods in laboratory and industrial settings. Moreover, all spills and leaks must be controlled using inert absorbent materials to mitigate environmental harm. Waste must be disposed of according to local guidelines as this substance is highly toxic to aquatic life. Recent studies indicate the compound persists in water environments while adversely affecting aquatic organisms, heightening the need to restrict its release into water bodies.
Addressing Spills and Contaminated Clothing
It is essential to manage both contaminated clothing and spills with particular care due to their potential hazards. Contaminated clothes must be handled as outlined in the organization’s protocol. Employees must remove contaminated clothing and place them in labeled, sealed bags to reduce exposure. These items should not be put through regular washing cycles as this will lead to cross-contamination. Such items need to be incinerated or laundered by specialized facilities designed to deal with hazardous materials.
Every spill, no matter how small, requires immediate attention to mitigate potential harm to the environment. Small spills can be contained and cleaned using non-reactive (inert) materials such as sand, vermiculite, or commercial spill pads. For larger spills, secondary containment measures such as absorbent booms and specialized spill kits are recommended. The latest research from the Environmental Protection Agency (EPA) indicates that rapid containment can reduce the risk of groundwater contamination by 65%.
Every type of spilled waste should be kept in clearly marked containers made of chemically resistant materials and aligned with local and global waste regulations. A recent study conducted this year showed, improper chemical disposal leads to 20% of documented hazardous contamination incidences. This number, alone, reinforces the need for strict compliance with disposal guidelines. Compliance with governing policies, as well as proper incident documentation for risk management should also be maintained.
How is 1-Bromobutane Synthesized?
The reaction of 1-butanol with hydrobromic acid, in the presence of sulfuric acid as a catalyst, synthesizes 1-bromobutane. This reaction is categorized as a nucleophilic substitution reaction, which replaces the hydroxyl group (-OH) present in 1-butanol with bromine yielding 1-bromobutane. The reaction should be conducted under controlled temperatures for safety and efficiency.
Common Methods of 1-Bromobutane Synthesis
The common methods of 1-bromobutane synthesis include nucleophilic substitution using hydrobromic acid (HBr), phosphorus tribromide (PBr3), or sodium bromide and sulfuric acid.
| Method | Reagent | Catalyst | Conditions | Yield |
|---|---|---|---|---|
| HBr Reaction | HBr | H2SO4 | Controlled heat | High |
| PBr3 Method | PBr3 | None | Ambient | Moderate |
| NaBr-H2SO4 Method | NaBr, H2SO4 | None | Heated | High |
The Role of Hydrogen Bromide in the Synthesis Process
Hydrogen bromide (HBr) is important in the synthesis of 1-bromobutane as it provides the bromide ion necessary for the nucleophilic substitution reaction. This process usually revolves around the treatment of 1-butanol with HBr in the presence of acids, wherein sulfuric acid (H2SO4) is used as a catalyst for increasing the reaction rate. The advantage of using HBr lies in its high reactivity and consistent results. As stated recently, this process can result in greater than 90% yield under certain conditions, which makes it one of the best methods offered for the synthesis of 1-bromobutane.
As with most organic reactions, the mechanism begins with the protonation of the hydroxyl group (-OH) of 1-butanol by sulfuric acid, which transforms it to a better leaving group. Thereafter, bromide ion from HBr performs nucleophilic attack and replaces the hydroxyl group to give the product 1-bromobutane. These types of reactions are done under moderate heating (around 90–100 °C) in order to enhance the reaction rates while minimizing side reactions.
Newer research also investigates other factors related to environmental impacts of this technique. New methods focus on reducing environmental impact and maximizing atom economy. Also, modern methods including microwave heating and heating without solvents have been proven to increase the yield together with the sustainability of the process. Such breakthroughs continue to demonstrate why the HBr approach is still a preferred method for synthesizing 1-bromobutane in both industrial and laboratory contexts.
Formation of Grignard Reagent Using 1-Bromobutane
1-Bromobutane is an important starting compound for the preparation of Grignard reagents which are used extensively in various organic reactions. It undergoes reaction with magnesium in dry ether solvents such as diethyl ether or THF to form butylmagnesium bromide which is a versatile Grignard reagent. This reagent undergoes nucleophilic addition reactions quite readily, one example is reacting with carbonyl groups to form alcohols.
Studies emphasize the effectiveness of using 1-bromobutane in forming Grignard reagents. Their formation is substantially impacted by the reaction parameters, such as the magnesium and 1-bromobutane’s temperature and cleanliness. For example, above 90% reaction yields can be achieved with high-purity magnesium turnings or ribbon shaped magnesium. Moreover, lack of moisture and oxygen is crucial since these elements can deactivate the Grignard reagent.
These reagents continue to be utilized for large-scale industrial production of pharmaceuticals, agrochemicals, and polymers. One example would be butylmagnesium bromide which is a vital intermediate chemical in synthesizing some secondary and tertiary alcohols that are utilized in drug development. Additionally, new developments of in-line monitoring systems and reactor technologies have improved the Grignard reagent manufacturing process by increasing scalability and reproducibility for safer handling of the highly reactive compounds involved.
What is the Chemical Identification of 1-Bromobutane?
1-Bromobutane, or n-butyl bromide, is an organic compound that can be categorized by its chemical formula C4H9Br. It is part of the class of alkyl halides and contains a butane chain that has a hydrogen atom replaced with bromine. Its molecular weight is about 137.02 g/mol
Getting to Know the CAS Number: 109-65-9
1-Bromobutane has been assigned CAS (Chemical Abstracts Service) number 109-65-9 which has become synonymous with the chemical id 1-bromobutane. Like other critically acclaimed and recognized identifiers, this number helps eliminate information loss while sharing details about the chemical in question across industries, domains, and fields of research.
CAS 109-65-9 describes 1-Bromobutane as a liquid that is colorless and volatile, with a boiling point around 101 degrees celsius. At room temperature (20 degrees celsius), the density would be 1.27 g/cm³, meaning that it would be a little less soluble in water, but highly soluble in organic substances such as ethanol, acetone, and diethyl ether. This compound is highly volatile and flammable, and so care should be taken to avoid ignition and exposure in the event that the compound is burnt.
It has become popular in organic synthesis, especially for butylating butane into other molecular structures. Most ‘pharma’ and agro-chemicals manufactured and even some intermediates for synthetic materials rely on this compound. It must be stored in a cool ventilated place away from open flames and other strongly oxidizing chemicals.
In all ‘Br-Butane’ related research, the CAS number is the only piece of information needed to access untapped wealth of information, detailed and reliable data from multiple platforms without any parallel or comparison in consistency.
1-Bromobutane Specification and Documentation
Memorizing the specifications and a document checklist for ‘Br-butane’ batch works is crucial to guarantee efficacy across repetitions and eliminate reaction to reaction variations. The precisions required for substances claim their purity, boiling point and even the cited potential impurities need to be described in the certificate of analysis. These documents alongside the COA serve as proof enabling me to rely on precision and trust the tests for validity prior to performing the tests. For work safety and compliance, permit me claim there are no better resources than safety datasheets. Sticking to these permits me reliability while enabling complete precision during my work as well.
Significance of MSDS and SDS Documents for 1-Bromobutane
The Material Safety Data Sheet (MSDS) and Safety Data Sheet (SDS) are essential documents for the appropriate use, handling, and storage of 1-bromobutane. Flammable and hazardous liquid 1-bromobutane (CAS Number 109-65-9) has a flashpoint of approximately 18°C (64°F), requiring it to be stored in a cool and well-ventilated place far from sources of combustion. Its boiling point is around 101°C (213.8°F) and at standard temperature, its density is about 1.269 g/cm³.
As outlined in the SDS, exposure to 1-bromobutane may lead to skin, eye and respiratory system irritation. One risk of chronic exposure is damage to the nervous system. When handling the chemical, PPE such as gloves, safety goggles and protective clothing are indispensable. Additionally, breathing the chemical can be prevented by providing adequate ventilation or using fume hoods.
No Less Important concern described in the SDS is the ecological impact. 1-Bromobutane is moderately harmful to aquatic organisms and its environmental discharge is forbidden. Such waste must be disposed of in accordance with local laws that protect the environment and legal boundaries. Guidelines within MSDS and SDS allow for the safe human and environmental handling of 1-Bromobutane.
What are the Reaction Characteristics of 1-Bromobutane?
1-Bromobutane mostly undergoes substitution and elimination reactions. It is reactive owing to the presence of a polar carbon-bromine bond which makes it undergo nucleophilic attack. Substitution reactions usually occur with the replacement of bromine with a nucleophile. Furthermore, elimination reactions can form alkenes. Each of these reactions happens with certain conditions, and which reaction will occur depends on the reagents and the environment.
1-Bromobutane as an Alkylating Agent
1-Bromobutane is very good as an alkylating agent because it can be used to butylate many substrates. This property is important in organic synthesis for forming C-C and C- heteroatom bonds which are essential during the construction of complex molecules. The alkylation reactions of 1-Bromobutane take place because of the polar carbon-bromine bonds which allow bromine to be substituted by nucleophiles.
As an example, 1-Bromobutane will react in a Williamson ether synthesis with sodium ethoxide (C2H5ONa) to form butoxyethane. Also, 1-Bromobutane is in the production of Quaternary ammonium salts by reacting with tertiary amines, which are used in the manufacture of surfactants and antiseptics.
Reactivity with Strong Oxidizing Agents
1-Bromobutane has very few direct reactions with strong oxidizing agents because of the stable structure of the alkyl bromide. However, strong oxidizers can sometimes initiate the conversion of 1-Bromobutane to butanol or other substituted oxygen forms of butane via substitution reactions. For example, 1-bromobutane can undergo hydrolysis with silver nitrate (AgNO3) in the presence of ethanol, leading to the formation of butanol. This reaction is often used in organic chemistry for alkyl halides and is known as the fall of krebs and heins reaction.
Recent studies suggest that the reactivity of 1-Bromobutane with oxidizing agents is greatly dependent on the polarity of the solvent utilized. For example, polar aprotic solvents like dimethyl sulfoxide (DMSO) or acetonitrile tend to increase the reactivity because they stabilize the intermediate dipole reaction. There are some data with optimally controlled reactions along with other suitable conditions where substituted 1-Bromobutane results in about 85 percent of butanol with very few side reactions ensuring efficient reaction completion.
In terms of safety, depending on the chemical properties 1-bromobutane has, a more careful manner is needed to deal with oxidizing agents, because improper conditions might lead to some dangerous unwanted by-products or exothermic reactions that might lead to some safety problems.
Grasping the Basics of the Rate Coefficient for the Reaction of 1-Bromobutane
The rate coefficient for the reaction of 1-Bromobutane is impacted by temperature, solvent, and catalyst due to its physical properties. In most lab settings, the reaction occurs under second order kinetics where the rate depends on the concentration of 1-Bromobutane and the nucleophile present in the reaction mixture. It has also been noted that temperatures and highly polar solventsmay increase solvent effects and therefore reaction rates via activation energy lowering methods..
Reference sources
- Effect of alkyl-group flexibility on the melting point of imidazolium-based ionic liquids
- Authors: K. Bernardino et al.
- Journal: The Journal of Chemical Physics
- Publication Date: 2020-07-28
- Key Findings: This study investigates how the flexibility of alkyl groups in imidazolium-based ionic liquids affects their melting points. The research uses molecular dynamics simulations to determine the melting points of specific ionic liquids and examines the impact of molecular flexibility on melting behavior.
- Methodology: The authors employed molecular dynamics simulations to analyze the melting points of 1-ethyl-3-methyl-imidazolium hexafluorophosphate and 1-decyl-3-methyl-imidazolium hexafluorophosphate, focusing on the rotational flexibility of dihedral angles in both solid and liquid phases(Bernardino et al., 2020, p. 044504).
- Melting Point, Enthalpy of Fusion, and Heat Capacity Measurements of Several Polyfunctional, Industrially Important Compounds by Differential Scanning Calorimetry
- Authors: Joseph Hogge et al.
- Journal: Journal of Chemical & Engineering Data
- Publication Date: 2018-05-04
- Key Findings: This paper reports on the melting points and other thermal properties of various industrially important compounds, providing essential data for understanding their thermal behavior.
- Methodology: The study utilized differential scanning calorimetry (DSC) to measure melting temperatures, enthalpies of fusion, and heat capacities of several compounds(Hogge et al., 2018, pp. 2500–2511).
- Phase Behavior, Densities, and Isothermal Compressibility of Carbon Dioxide + 1-Bromobutane, Carbon Dioxide + 1-Chlorobutane, and Carbon Dioxide + 1-Methylimidazole
- Authors: Xiaoting Chen et al.
- Journal: Journal of Chemical & Engineering Data
- Publication Date: 2010-01-14
- Key Findings: This study explores the phase behavior and critical parameters of mixtures involving 1-bromobutane, providing insights into its interactions with carbon dioxide.
- Methodology: The authors conducted experiments using a high-pressure variable-volume view cell to determine phase behavior and densities of the mixtures(Chen et al., 2010, pp. 385–399).
Frequently Asked Questions (FAQs)
Q: What is the melting point of 1-bromobutane?
A: Butyl bromide’s melting point is around negative one hundred and twelve degrees Celsius, and negative one hundred sixty nine point six Fahrenheit. At room temperature, butyl bromide is rather fluid.
Q: How does 1-bromobutane react with Hydrogen?
A: A catalyst along with specific conditions is necessary for the reaction of butyl bromide and hydrogen. While it is possible for hydrogen atoms to substitute for the bromine atom of butyl bromide, such reactions are rarely conducted in the lab.
Q: Is 1-bromobutane insoluble in water?
A: 1-bromobutane does remain insoluble in water and can be classified a non polar solvent for organic compounds.
Q: What safety precautions should be taken when handling 1-bromobutane?
A: Vigorously rub with water while removing contacts until the wash is clear. Do not sniff vapors as it irritates the lungs. While wearing goggles and gloves, do not touch skin, eyes, or breathe in 1-bromobutane, as its fumes will irritate the trachea.
Q: Can 1-bromobutane be used to prepare organometallic compounds?
A: Yes, 1-bromobutane can be used for the preparation of organometallic compounds and as such reagents will undergo reactions with magnesium metal to produce organomagnesium compounds Grignard, organometallic compounds that serve as building blocks in diverse organic synthesis.
Q: What n-butylbromide refers to and it’s relationship to 1-bromobutane.
A: n-butylbromide is a synonym for 1-bromobutane which means that both terms correspond to the same chemical compound and are frequently utilized in an interchangeable manner.
Q: What is the behavior of 1-bromobutane in chromatography?
A: 1-bromobutane will be separated from other mixture components in chromatography and will behave differently from other components in the mixture due to its boiling point, polarity, and other physical and chemical characteristics.
Q: What reactions occur when 1-bromobutane is treated with alkaline reagents?
A: Alkaline reagents when mixed with 1-bromobutane result to undergo a nucleophilic substitution reaction where usually alcohols such as n-butanol are formed.
Q: What are the spectroscopic techniques to calculate the rotational constants of 1-bromobutane?
A: Spectroscopic techniques can be used to estimate the rotational constants of 1-bromobutane and this helps in knowing the molecular structure and dynamics of the compound.
Q: Compare and contrast 1-bromobutane with 2-bromopropane.
A: 1-bromobutane differs from 2-bromopropane as both are classified differently as brominated hydrocarbons where one is linear and the other is a branched chain which makes them differ in chemical and physical properties.
