ChemicalBook > CAS DataBase List > Benzyl bromide

Benzyl bromide

Product Name
Benzyl bromide
CAS No.
100-39-0
Chemical Name
Benzyl bromide
Synonyms
bromomethylbenzene;1-Bromotoluene;cyclite;ALPHA-BROMOTOLUENE;1-(Bromomethyl)benzene;ai3-15300;Benzybromide;Bromo Thluene;-Bromotoluene;BENZYL BROMIDE
CBNumber
CB6761035
Molecular Formula
C7H7Br
Formula Weight
171.03
MOL File
100-39-0.mol
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Benzyl bromide Property

Melting point:
-3 °C
Boiling point:
198-199 °C(lit.)
Density 
1.44 g/mL at 20 °C
vapor density 
5.8 (vs air)
vapor pressure 
0.5 hPa (20 °C)
refractive index 
n20/D 1.575(lit.)
Flash point:
188 °F
storage temp. 
Store below +30°C.
solubility 
Miscible with benzene, carbon tetrachloride, ethanol and ether.
form 
Liquid
color 
Clear colorless to yellow
Odor
Very sharp, pungent, like tear gas.
Sensitive 
Moisture Sensitive/Light Sensitive
Merck 
14,1128
BRN 
385801
Dielectric constant
5.1（20℃）
Stability:
Stable. Combustible. Incompatible with strong oxidizing agents.
InChIKey
AGEZXYOZHKGVCM-UHFFFAOYSA-N
CAS DataBase Reference
100-39-0(CAS DataBase Reference)
NIST Chemistry Reference
Benzene, (bromomethyl)-(100-39-0)
EPA Substance Registry System
Benzyl bromide (100-39-0)
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Safety

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
39-2
RIDADR 
UN 1737 6.1/PG 2
WGK Germany 
2
RTECS 
XS7965000
F 
9-19-21
TSCA 
Yes
HS Code 
2903 99 80
HazardClass 
6.1
PackingGroup 
II
Hazardous Substances Data
100-39-0(Hazardous Substances Data)
Toxicity
dns-esc 1300 mmol/L ZKKOBW 92,177,78
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
B17905
Product name
Benzyl bromide
Purity
reagent grade, 98%
Packaging
25g
Price
$22.4
Updated
2024/03/01
Sigma-Aldrich
Product number
B17905
Product name
Benzyl bromide
Purity
reagent grade, 98%
Packaging
2.5kg
Price
$302
Updated
2024/03/01
TCI Chemical
Product number
B0411
Product name
Benzyl Bromide (stabilized with Propylene Oxide)
Purity
>98.0%(GC)
Packaging
25g
Price
$17
Updated
2024/03/01
TCI Chemical
Product number
B0411
Product name
Benzyl Bromide (stabilized with Propylene Oxide)
Purity
>98.0%(GC)
Packaging
100g
Price
$45
Updated
2024/03/01
Alfa Aesar
Product number
A13535
Product name
Benzyl bromide, 99%
Packaging
50g
Price
$34.9
Updated
2024/03/01
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Benzyl bromide Chemical Properties,Usage,Production

Description

Benzyl bromide is a combustible, colorless toyellow liquid with a pleasant odor. Molecularweight=171.05;Specific gravity (H2O:1) =1.438; Boilingpoint= 198℃; Freezing/Melting point =-4.0℃;Flashpoint =79℃ (cc). Hazard Identification (based on NFPA-704 M Rating System): Health 3, Flammability 2,Reactivity 1. Insoluble in water (slowly decomposes).

Chemical Properties

Benzyl bromide is an aromatic compound in which the benzene ring substituted with a bromomethyl group, and is produced by the reaction of toluene with bromine in the presence of an oxidizing agent. It is a combustible, colorless to yellow liquid with a pleasant odor. insoluble in water and easily soluble in most organic solvents. Has a strong tearing effect and unpleasant pungent odor, minimum irritant concentration of 4 mg/m3, intolerable concentration of 50-60 mg/m3.

Uses

Making foaming and frothing agents, organic synthesis.

Uses

Benzyl bromide is widely useful in organic synthesis as a benzyl protecting group for alcohols and carboxylic acids. It is used in the preparation of foaming and frothing agents, quaternary ammonium compounds, peniclins, photographic chemicals, synthetic resins, dyes and plasticizers and esters. It is also involved in the synthesis of (E)-(2-Iodovinyl)benzene by reacting it with diiodomethane.

Application

Benzyl bromide is an aromatic halide that is mainly used as a protecting agent for protecting hydroxy group of alcohols via O-benzylation reaction. It has been used as an initiator in the synthesis of poly(styrene-b-methylmethacrylate) copolymers by atom transfer radical polymerization. It can undergo Menschutkin reaction with 1, 2-dimethylimidazole to form 3-benzyl-1, 2-dimethylimidazolium bromide.

Preparation

Benzyl bromide is synthesized by toluene bromination. Toluene heated to 50°C, add bromine reaction, the reaction temperature of 75-80°C, reaction 6h, fractional distillation at atmospheric pressure to remove the fraction before 140°C, and then distillation under reduced pressure, collect 112-114°C(2.0kPa) fraction, to get benzyl bromide.

Definition

ChEBI: Benzyl bromide is a member of the class of benzyl bromides that is toluene substituted on the alpha-carbon with bromine. It has a role as a lachrymator.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 3412, 1973 DOI: 10.1021/ja00791a072
Tetrahedron Letters, 29, p. 707, 1988 DOI: 10.1016/S0040-4039(00)80190-2
The Journal of Organic Chemistry, 51, p. 929, 1986 DOI: 10.1021/jo00356a032

General Description

Benzyl bromide appears as a colorless liquid with an agreeable odor. Toxic by inhalation and by skin absorption. It is slightly soluble in water and denser than water (density 1.44 g / cm3 (Aldrich)). A lachrymator. Corrosive to metals and tissue.

Air & Water Reactions

Sensitive to exposure to light and moisture. Slightly soluble in water.

Reactivity Profile

Benzyl bromide reacts with water, alcohols, common metals (except nickel and lead), bases, amines and oxidizing agents. . Benzyl bromide stored over activated 4A molecular sieve burst a bottle due to condensation-polymerization reaction with generation of HBr gas, [Chem. Eng. News, 1979, 57(12), 74].

Hazard

Highly toxic. Corrosive to skin and tissue. A lachrymator.

Health Hazard

Inhalation causes irritation of nose and throat; severe exposure may cause pulmonary edema. Vapors cause severe eye irritation; liquid can burn eyes. Skin contact causes irritation. Ingestion causes irritation of mouth and stomach.

Chemical Reactivity

Reactivity with Water Reacts slowly generating hydrogen bromide (hydrobromic acid); Reactivity with Common Materials: Decomposes rapidly in the presence of all common metals except nickel and lead, liberating heat and hydrogen bromide; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Rinse with sodium bicarbonate or lime solution; Polymerization: Polymerizes with evolution of heat and hydrogen bromide when in presence with all common metals except nickel and lead; Inhibitor of Polymerization: None.

Safety Profile

Intensely irritating and corrosiveto skin, eyes, and mucous membranes. Large doses causecentral nervous system depression. Mutation datareported. Reaction with molecular sieve produces toxichydrogen bromide gas.

Potential Exposure

It is used as a chemical intermediate; in organic syntheses; as a foaming and frothing agent.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seekmedical attention immediately. If this chemical contactsthe skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attentionimmediately. If this chemical has been inhaled, removefrom exposure, begin rescue breathing (using universalprecautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transferpromptly to a medical facility. When this chemical hasbeen swallowed, get medical attention. If victim is conscious,administer water or milk. Do not induce vomiting.Medical observation is recommended for 24 48 h afterbreathing overexposure, as pulmonary edema may bedelayed. As first aid for pulmonary edema, a doctor orauthorized paramedic may consider administering a corticosteroid spray

storage

Color Code—Blue: Health Hazard/Poison: Storein a secure poison location. Color Code—White: Corrosiveor Contact Hazard; Store separately in a corrosion-resistantlocation. Store in tightly closed containers in a cool, wellventilated area away from water and other incompatiblematerials listed above.

Shipping

UN1737 Benzyl Bromide, Hazard class: 6.1; Labels: 6.1—Poisonous materials, 8—Corrosive material.

Purification Methods

Wash benzyl chloride with conc H2SO4 (CARE), water, 10% Na2CO3 or NaHCO3 solution, and again with water. Dry it with CaCl2, Na2CO3 or MgSO4 and fractionally distil it in the dark, under reduced pressure. It has also been thoroughly degassed at 10-6 mm and redistilled in the dark. This gives material with max (MeCN): 226nm ( 8200) [Mohammed & Kosower J Am Chem Soc 93 2709 1971]. [Beilstein 5 IV 829.] Handle in a fume cupboard, extremely LACHRYMATORY.

Incompatibilities

May form explosive mixture with air. Contact with water forms hydrogen bromide and benzyl alcohol. Incompatible with strong oxidizers, bases, magnesium. Attacks metals, except nickel and lead, in the presence of moisture.

Waste Disposal

Pour into vermiculite, sodium bicarbonate, or a sand-soda ash mixture and transfer to paper boxes, then to an open incinerator. Alternatively, mix Benzyl Bromide 417 with flammable solvent and spray into incinerator equipped with after burner and alkali scrubber.

Benzyl bromide Preparation Products And Raw materials

Raw materials

Preparation Products

2-(Boc-aminomethyl)-piperidine (S)-(-)-N-Benzyl-1-phenylethylamine Diethyl benzylmalonate 1-BENZYL-1,4-DIAZEPANE Candesartan 2-Methyl-1-phenyl-2-propanol 4-Amino-1-benzylpiperidine O-(2-MethoxyEthoxy)BenzeneSulfonamide 2-(4-BENZYLOXYPHENYL)ETHANOL N-(4-(Benzyloxy)benzylidene)-4-fluoroaniline CYCLOPROTHRIN Benzyldimethylhexadecylammonium chloride Cinosulfuron 3,5-Dibenzyloxybenzyl alcohol 4-BENZYLOXY-3-METHOXYBENZALDEHYDE trans-2,5-Dimethylpiperazine Sulindac 4-(Boc-Aminomethyl)piperidine TERBUTALINE SULFATE 7-Hydroxyindole 4-Benzyloxybenzeneboronic acid 3-Benzyloxybenzaldehyde 3,5-BIS(BENZYLOXY)BENZYL BROMIDE 1-BENZYL-2-IMIDAZOLECARBOXYLIC ACID Indobufen 4-BENZYLOXYANILINE 1,3,5-Benzenetricarboxaldehyde Anagrelide Butenafine hydrochloride 6-CHLORO-1H-PYRROLO[2,3-B]PYRIDINE Benzyldodecyldimethylammonium bromide 5-Hydroxyindole N-BOC-O-Benzyl-L-serine 2-Hydroxydiphenylmethane BOC-3-IODO-D-ALANINE BENZYL ESTER 3-METHYLADENINE (R)-(-)-Benzyl glycidyl ether 4-METHYL-1-PHENYL-2-PENTANOL CROCONAZOLE alpha-[4-[2-(diethylamino)ethoxy]phenyl]-alpha-phenylphenethyl alcohol
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View Lastest Price from Benzyl bromide manufacturers

Wuhan Boyuan Import & Export Co., LTD
Product
Benzyl bromide 100-39-0
Price
US $0.00-0.00/KG
Min. Order
10KG
Purity
99%
Supply Ability
5000tons
Release date
2023-04-04
Henan Fengda Chemical Co., Ltd
Product
Benzyl bromide 100-39-0
Price
US $100.00-1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2023-12-25
Shanxi Naipu Import and Export Co.,Ltd
Product
Benzyl bromide 100-39-0
Price
US $10.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
500tons/month
Release date
2021-10-25

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