Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > 2-Bromobutane

2-Bromobutane

2-Bromobutane structure

2-Bromobutane 

structure
  • CAS No:

    78-76-2

  • Formula:

    C4H9Br

  • Chemical Name:

    2-Bromobutane

  • Synonyms:

    Butane,2-bromo-;2-Bromobutane;sec-Butyl bromide;Methylethylbromomethane;2-Butyl bromide;(±)-sec-Butyl bromide;(±)-2-Bromobutane;NSC 8417;5787-31-5

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

colourless liquid with a pleasant odour

2-Bromobutane Basic Attributes

137.02

137.02

505949

201-140-7

8417

2339

DTXSID7021499

Clear, colorless liquid

29033036

Characteristics

0

2.56

Clear colorless to yellow-brown Liquid

1.2425 g/cm3 @ Temp: 25 °C

-112 °C

91.2 °C

70 °F

1.436

H2O: insoluble

Flammables area

70 hPa (20 °C)

Inflammable in case of open flame, high temperature, oxidant; decomposition of toxic bromide gas by high heat

2.6-6.6%(V)

Pleasant odor

Henry's Law constant = 1.6X10-2 atm-cu m/mol at 25 °C (est)

FREEZING POINT: LESS THAN -50 °C|Index of refraction = 1.4359-1.4362 at 20 °C/D; Specific optical rotation = +42.64 deg at 20 °C/D /d-form/|Index of refraction = 1.4368 at 20 °C/D; Specific optical rotation = -43.7 deg at 20 °C/D /l-form/|...Can react with oxidizing materials|Insoluble in water; soluble in ethanol, chloroform; miscible with ether, acetone /Butane, 2-bromo-, (l)-/|For more Other Experimental Properties (Complete) data for 2-BROMOBUTANE (7 total), please visit the HSDB record page.

Highly flammable. Insoluble in water.

Halogenated Organic Compounds

Highly Flammable

Halogenated aliphatic compounds, such as 2-BROMOBUTANE, are moderately or very reactive. Halogenated organics generally become less reactive as more of their hydrogen atoms are replaced with halogen atoms. Low molecular weight haloalkanes are highly flammable and can react with some metals to form dangerous products. Materials in this group are incompatible with strong oxidizing and reducing agents. Also, they are incompatible with many amines, nitrides, azo/diazo compounds, alkali metals, and epoxides. Gives toxic fumes of bromine when burned.

34.41 kJ/mol at 25 °C

Safety Information

II

3

UN 2339 3/PG 2

2

11-36/37/38-10-52

16-23-24/25-37/39-26

EJ6228000

F,Xi

Treasury is ventilated, low temperature and dry; stored separately from oxidant

Irritant/Highly Flammable

Stable. Flammable. Incompatible with strong oxidizing agents.

P210

H225

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

...Can react with oxidizing materials

Special Hazards of Combustion Products: Toxic fumes of Br Behavior in Fire: May form explosive mixtures with air in a fire. (USCG, 1999)|Flammable - 3rd degree

|Danger|H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P234, P240, P241, P242, P243, P260, P264, P273, P280, P301+P330+P331, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P363, P370+P378, P390, P403+P235, P404, P405, and P501|Aggregated GHS information provided by 53 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H225: Highly Flammable liquid and vapor [Danger Flammable liquids]|P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. LARGE SPILL: Consider initial downwind evacuation for at least 300 meters (1000 feet). FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

Excerpt from ERG Guide 130 [Flammable Liquids (Water-Immiscible / Noxious)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). All equipment used when handling the product must be grounded. Do not touch or walk through spilled material. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. A vapor-suppressing foam may be used to reduce vapors. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. Use clean, non-sparking tools to collect absorbed material. LARGE SPILL: Dike far ahead of liquid spill for later disposal. Water spray may reduce vapor, but may not prevent ignition in closed spaces. (ERG, 2016)

Approved respirator, chemical-resistant gloves, safety goggles, other protective clothing. (USCG, 1999)|Personnel Protection: ... Wear appropriate chemical protective gloves, boots and goggles.

Dangerous, when exposed to heat or flame.

To fight fire use water, spray or mist, foam, carbon dioxide, or dry chemical.|If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources.|Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.

/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.|/GUIDE 130: FLAMMABLE LIQUIDS (Non-Polar/Water-Immiscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.|For more DOT Emergency Guidelines (Complete) data for 2-BROMOBUTANE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Toxicity

sec-Butyl bromide's production and use as an alkylating agent and in synthesis(1) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that sec-butyl bromide is expected to have high mobility in soil(SRC). Volatilization of sec-butyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.6X10-2 atm-cu m/mole(SRC), using a fragment constant estimation method(3). sec-Butyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 57 mm Hg(4). Biodegradation data were not available(SRC, 2005).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 68(SRC), determined from a structure estimation method(2), indicates that sec-butyl bromide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.6X10-2 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 3.5 hours and 4.7 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 19(SRC), from an estimated log Kow of 2.58(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sec-butyl bromide, which has a vapor pressure of 57 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase sec-butyl bromide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 12 days(SRC), calculated from its rate constant of 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). sec-Butyl bromide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of sec-butyl bromide with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 12 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). sec-Butyl bromide is expected to hydrolyze quickly based on neutral hydrolysis half-lives of similar compounds such as isopropyl bromide (2.1 days) and n-propyl bromide (26 days)(2). sec-Butyl bromide does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 19 was calculated for sec-butyl bromide(SRC), using an estimated log Kow of 2.58(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of sec-butyl bromide can be estimated to be 68(SRC). According to a classification scheme(2), this estimated Koc value suggests that sec-butyl bromide is expected to have high mobility in soil.

The Henry's Law constant for sec-butyl bromide is estimated as 1.6X10-2 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that sec-butyl bromide is expected to volatilize rapidly from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 3.5 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 4.7 days(SRC). sec-Butyl bromide's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). sec-Butyl bromide is expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 57 mm Hg(3).

Occupational exposure to sec-butyl bromide may occur through inhalation and dermal contact with this compound at workplaces where sec-butyl bromide is produced or used. (SRC)

Drug Information

Irritating to eyes, nose, throat, upper respiratory tract, and skin. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. (USCG, 1999)

Call a physician. EYES: Flush with running water for at least 15 minutes. SKIN: remove contaminated clothing and shoes. Flush affected areas with plenty of running water. Wash with soap and water. INHALATION: Move victim to fresh air. If breathing has stopped, give artificial respiration. If breathing is difficult, give oxygen. INGESTION: If victim is conscious, have victim drink water and have victim induce vomiting. If victim is unconscious, do nothing except keep victim warm. (USCG, 1999)

/SIGNS AND SYMPTOMS/ .../SRP: CNS depression/ in high concentrations.

2-bromobutane

2-Bromobutane Use and Manufacturing

Methods of Manufacturing

It is derived from the reaction of sec-butanol with hydrobromic acid in the presence of sulfuric acid. Slowly add concentrated sulfur to hydrobromic acid to mix, then add sec-butanol, reflux for 2-3 hours, distill out the bromide, separate the distillate, and take the organic phase in order to dilute with water, concentrated hydrochloric acid, water, sodium carbonate The solution was washed with water and dried with anhydrous calcium chloride. Finally, the 90.5-92.5°C fraction is collected by distillation to obtain the finished product.

Uses

In the field of chemistry, 2-bromobutane is widely used as an intermediate in organic synthesis, especially in the preparation of various butyl compounds. Due to the presence of its bromine atoms, it can undergo halogen exchange via SN1 or SN2 reactions to generate a variety of other organic compounds to meet different chemical needs. In addition, it is also used in the production of medicine, pesticides and dyes, and its application fields are wide and important. The versatility of 2-bromobutane lies in its potential applications in organic synthesis. As a Grignard reagent, it can be used to form carbon-carbon bonds, allowing the synthesis of more complex organic molecules. This ability makes 2-bromobutane a valuable intermediate for the production of a wide range of chemicals, pharmaceuticals and other industrially relevant compounds. The ability to form Grignard reagents, combined with its relatively simple structure, makes 2-bromobutane a useful tool in the hands of organic chemists. By performing selective reactions and transformations, researchers and industrial chemists can harness the unique properties of this organic compound to create a wide variety of products that contribute to advances in various fields, including pharmaceuticals, agrochemicals and specialty chemicals. For example, in the pharmaceutical industry, 2-bromobutane can be used to prepare complex organic molecules with specific biological activities. These molecules could be precursors for new types of drugs that could help treat everything from the common cold to rare genetic disorders and even cancer. Through precisely controlled chemical reactions, it is possible to ensure where and how 2-bromobutane is added to the molecule to optimize its pharmacological and bioavailability properties. In the field of agrochemicals, 2-bromobutane can be used to synthesize compounds with insecticidal, bactericidal or herbicidal activity. These chemicals play a vital role in protecting crops from pests and diseases and ensuring the security and stability of the global food supply. Through the chemical reactions they participate in, new pesticides that have less impact on the environment and are more selective to target organisms can be designed. In addition, 2-bromobutane has a wide range of applications in the synthesis of specialty chemicals. For example, it can be used to prepare high-performance polymers, optical materials, electronic chemicals, etc. These materials are widely used in aerospace, communications, energy and other high-tech fields, promoting the rapid development of science and technology. The versatility of 2-bromobutane and its potential for forming carbon-carbon bonds have made it an integral part of the modern chemical industry. With the continuous progress and innovation of organic synthesis technology, the application prospect of 2-bromobutane will be broader, providing new solutions to solve various chemical and engineering challenges. The combination of 2-bromobutane's physical and chemical properties, as well as its versatility in organic synthesis, make it a valuable and widely used organic compound in chemistry and other fields.

Butane, 2-bromo-: ACTIVE

Fire Hazards -> Flammable - 3rd degree

Computed Properties

Molecular Weight:137.02
XLogP3:2.3
Rotatable Bond Count:1
Exact Mass:135.98876
Monoisotopic Mass:135.98876
Heavy Atom Count:5
Complexity:19.6
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Recommended Suppliers of 2-Bromobutane

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.