1-Bromobutane Property

Melting point:

-112 °C

Boiling point:

100-104 °C(lit.)

Density 

1.276 g/mL at 25 °C(lit.)

vapor density 

4.7 (vs air)

vapor pressure 

150 mm Hg ( 50 °C)

refractive index 

n20/D 1.439(lit.)

Flash point:

23 °C

storage temp. 

Store below +30°C.

solubility 

0.6g/l

form 

Liquid

color 

Clear colorless to light yellow

Odor

characteristic odor

explosive limit

2.8-6.6%, 100°F

Water Solubility 

0.608 g/L (30 ºC)

Merck 

14,1553

BRN 

1098260

Dielectric constant

7.1600000000000001

Stability:

Stable. Flammable - note low flash point. Incompatible with strong oxidizing agents, strong bases.

InChIKey

MPPPKRYCTPRNTB-UHFFFAOYSA-N

LogP

2.75

CAS DataBase Reference

109-65-9(CAS DataBase Reference)

NIST Chemistry Reference

Butane, 1-bromo-(109-65-9)

EPA Substance Registry System

1-Bromobutane (109-65-9)

Safety

Hazard Codes 

F,Xi,N

Risk Statements 

11-36/37/38-51/53-10

Safety Statements 

16-26-60-37/39

RIDADR 

UN 1126 3/PG 2

WGK Germany 

2

RTECS 

EJ6225000

Autoignition Temperature

509 °F

TSCA 

Yes

HazardClass 

3

PackingGroup 

II

HS Code 

29033036

Hazardous Substances Data

109-65-9(Hazardous Substances Data)

Toxicity

LD50 orally in Rabbit: 2761 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P273Avoid release to the environment.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1-Bromobutane Chemical Properties,Usage,Production

Physical properties

1-Bromobutane is a highly flammable, colorlessliquid with a pleasant odor. Molecular weight = 137.04.Boiling point =101.6℃; Specific gravity (H2O:1) = 1.276at 20℃; Freezing/Melting point = 2112.4; Vapor density(air 5 1) = 4.68; Flash point =18℃ (21℃ for sec-isomer).Autoigniton temperature = 265℃. Explosive limits:LEL =2.6% at 100℃; UEL =6.6% at 100℃. HazardIdentification (based on NFPA-704 M Rating System):Health 2, Flammability 3, Reactivity 0. Insoluble in water.

Chemical Properties

1-bromobutane appears as a clear colorless to slightly yellow liquid with aroma. Flash point 65°F. Denser than water and insoluble in water, soluble in organic solvents such as alcohol, ether and chloroform.Vapors heavier than air.

Uses

1-Bromobutane is used as an intermediate in organic synthesis and as a solvent for cleaning and degreasing. It acts as an alkylating agent as well as to prepare organometallic compounds such as n-butyllithium. It is also involved in the synthesis of procaine and tetracaine. It reacts with magnesium metal to prepare the Grignard reagent, which is used to form carbon-carbon bonds.

Application

1-Bromobutane may be used as a derivatization reagent for multiple functional groups (amino, carboxyl, and phenolic hydroxyl groups) of amino acids to improve hydrophobicities and basicities of the amino acids. It may also be used as an internal standard for the quantification of 1- and 2-bromopropane in human urine by headspace gas chromatography.

Synthesis Reference(s)

Journal of the American Chemical Society, 86, p. 964, 1964 DOI: 10.1021/ja01059a073
Organic Syntheses, Coll. Vol. 1, p. 25, 1941
Synthesis, p. 326, 1982

General Description

1-Bromobutane, an alkyl halide, is an alkylating agent. Its rotational constants, nuclear quadrupole constants and centrifugal distortion constants have been stated based on microwave spectral data. The rate coefficient for the reaction of 1-bromobutane with hydrogen atoms has been reported to be 2.4±1.2x1010cm3mol-1s-1.

Air & Water Reactions

Highly flammable. Insoluble in water.

Reactivity Profile

1-Bromobutane is incompatible with strong bases and oxidizers [USCG, 1999].

Hazard

Flammable, dangerous fire risk.

Health Hazard

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

Safety Profile

Moderately toxic by intraperitoneal route. Mddly toxic by inhalation. Dangerous fire hazard when exposed to heat, flame, or oxidizers. Violent reaction with bromobenzene + sodium above 30℃. Can react with oxidizing materials. To fight fire, use CO2, dry chemical, mist or spray. See also BROMIDES.

Synthesis

1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced from bimolecular nucleophilic substitution reactions (Sn2).
The preparation method of 1-bromobutane is as follows: stirring n-butanol, sodium bromide, water and sulfuric acid evenly, heating under reflux for 3 hours, steaming out the crude bromobutane, washing with water, treating with cold concentrated sulfuric acid, and distilling to obtain the finished product.
Reaction equation: CH3CH2CH2CH2OH+NaBr+H2SO4→CH3CH2CH2CH2Br+Na2SO4+H2O
This halide is easily prepared by reacting butan-1-ol (primary alcohol) with sodium bromide solution and excess of concentrated sulfuric acid. The reaction between sodium bromide and sulphuric acid origins hydrobromic acid.

Potential Exposure

Butyl bromide is used to make otherchemicals and in making pharmaceuticals.

First aid

If 1-Bromobutane gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

storage

Color Code—Red: Flammability Hazard: Store ina flammable liquid storage area or approved cabinet awayfrom ignition sources and corrosive and reactive materials.Prior to working with Butyl bromide you should be trainedon its proper handling and storage. Store in tightly closedcontainers in a cool, well-ventilated area. Sources of ignition, such as smoking and open flames, are prohibitedwhere Butyl bromide is handled, used, or stored. Metal containers involving the transfer of 5 gallons or more of Butylbromide should be grounded and bonded. Drums must beequipped with self-closing valves, pressure vacuum bungs,and flame arresters. Use only nonsparking tools and equipment, especially when opening and closing containers ofButyl bromide.

Shipping

UN1126 & UN23391- & 2-Bromobutane, Hazard Class: 3; Labels: 3—Flammable liquid.

Purification Methods

Wash the bromide with conc H2SO4, water, 10% Na2CO3 and again with H2O. Dry it over CaCl2, CaSO4 or K2CO3, and distil it. Redistil it after drying with P2O5, or pass it through two columns containing 5:1 silica gel/Celite mixture and store it with freshly activated alumina. [Beilstein 1 IV 258.]

Incompatibilities

1-Bromobutane vapors may form explosive mixtures with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fire or explosion. Keep away from alkaline materials, strong bases, strong acids, oxyacids, epoxides. May accumulate static charge and cause its vapors to ignite.

Waste Disposal

Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed