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100-39-0

Basic Information
CAS No.: 100-39-0
Name: Benzene,(bromomethyl)-
Article Data: 503
Cas Database
Molecular Structure:
Molecular Structure of 100-39-0 (Benzene,(bromomethyl)-)
Formula: C7H7Br
Molecular Weight: 171.037
Synonyms: Toluene,a-bromo- (8CI);(Bromomethyl)benzene;(Bromophenyl)methane;1-Bromomethylbenzene;NSC 8041;Phenylmethyl bromide;a-Bromotoluene;w-Bromotoluene;
EINECS: 202-847-3
Density: 1.438 g/cm3
Melting Point: -3 ºC
Boiling Point: 198.499 ºC at 760 mmHg
Flash Point: 86.667 ºC
Solubility: N/A
Appearance: clear light amber liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 39-2
Transport Information: UN 1737 6.1/PG 2
PSA: 0.00000
LogP: 2.58150
Synthetic route
108-88-3

toluene

100-39-0

benzyl bromide

Conditions
ConditionsYield
With bromine In tetrachloromethane for 1.5h; Ambient temperature;100%
With manganese(IV) oxide; bromine In dichloromethane at 0℃; for 1h; Product distribution; Further Variations:; Solvents; Temperatures; reaction time;100%
With bromine; sodium t-butanolate In cyclohexane Heating;100%
100-51-6

benzyl alcohol

100-39-0

benzyl bromide

Conditions
ConditionsYield
With 1,1,1,2,2,2-hexamethyldisilane; pyridinium hydrobromide perbromide In chloroform at 25℃; for 0.5h;100%
With phosphorus tribromide In benzene at 20℃;100%
Stage #1: benzyl alcohol With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane for 0.0833333h;
Stage #2: With potassium bromide In dichloromethane; N,N-dimethyl-formamide for 0.5h;
99%

cis-{(PhCH2)2Co(III)(2,2'-bipyridine)2}ClO4

100-39-0

benzyl bromide

Conditions
ConditionsYield
With bromine In acetonitrile one-electron oxidn. of cis-Co complex by Br2 at 298 K; monitored by (1)H-NMR;100%
103514-63-2

C13H25N3PS(1+)

100-39-0

benzyl bromide

Conditions
ConditionsYield
With bromide In N,N-dimethyl-formamide98%
100-52-7

benzaldehyde

100-39-0

benzyl bromide

Conditions
ConditionsYield
With Dichloromethylsilane; phosphorus tribromide; iron(III) chloride In acetonitrile for 4h; Heating;97%
With polymethylhydrosiloxane; dimethylbromosulphonium bromide In chloroform at 20℃; for 5h;96%
With chloro-trimethyl-silane; 1,1,3,3-Tetramethyldisiloxane; lithium bromide In acetonitrile at 80℃; for 30h;94%
620-05-3

iodomethylbenzene

100-39-0

benzyl bromide

Conditions
ConditionsYield
With bismuth(III) bromide In 1,2-dichloro-ethane at 25℃; for 2.25h;97%
With pyridine; tributyltin bromide at 50℃; Thermodynamic data; Equilibrium constant; other temperatures, Δ G;26 % Spectr.
936-51-6

2-phenyl-1,3-dioxolane

100-39-0

benzyl bromide

Conditions
ConditionsYield
With triethylsilane; Acetyl bromide; tin(II) bromide In dichloromethane for 3h; Ambient temperature;96%
1927-62-4

tetrahydro-2-(benzyloxy)-2H-pyran

100-39-0

benzyl bromide

Conditions
ConditionsYield
With 4-aminophenyl diphenylphosphinite; N-Bromosuccinimide In dichloromethane at 20℃; for 2h;95%
With boron trifluoride diethyl etherate; lithium bromide In acetonitrile for 24h; Ambient temperature;89%
With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate; bromine at 80℃; for 2h;89%
350-50-5

benzyl fluoride

100-39-0

benzyl bromide

Conditions
ConditionsYield
With hydrogen bromide at 130℃; for 1h;95%
Multi-step reaction with 2 steps
1: 12 N HCl / 105 °C
2: 93 percent / 47percent aq. HBr / 1 h / 130 °C
View Scheme
14642-79-6

benzyloxy-trimethylsilane

100-39-0

benzyl bromide

Conditions
ConditionsYield
With 4-aminophenyl diphenylphosphinite; bromine In dichloromethane at 20℃;95%
With 1-(2-OPPh2-propyl)-3-methylimidazolium hexafluorophosphate; bromine at 80℃; for 1h;87%
With Tri-n-butylfluorphosphoniumbromid In benzene at 20℃; for 24h;81%
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Specification

The Benzyl bromide, with the CAS registry number 100-39-0, is also known as a-Bromotoluene. It belongs to the product categories of Pharmaceutical Intermediates; Aromatic Halides (substituted); Organics; Benzyl; Biochemistry; Reagents for Oligosaccharide Synthesis. Its EINECS registry number is 202-847-3. This chemical's molecular formula is C7H7Br and molecular weight is 171.03. What's more, both its IUPAC name and systematic name are the same which is called Bromomethylbenzene. It is an organic compound consisting of a benzene ring substituted with a bromomethyl group. This chemical is a colorless liquid that is decomposed slowly in water.

Physical properties about Benzyl bromide are: (1)ACD/LogP: 2.81; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.805; (4)ACD/LogD (pH 7.4): 2.805; (5)ACD/BCF (pH 5.5): 79.805; (6)ACD/BCF (pH 7.4): 79.805; (7)ACD/KOC (pH 5.5): 799.993; (8)ACD/KOC (pH 7.4): 799.993; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 0 Å2; (13)Index of Refraction: 1.568; (14)Molar Refractivity: 38.901 cm3; (15)Molar Volume: 118.926 cm3; (16)Surface Tension: 38.493 dyne/cm; (17)Density: 1.438 g/cm3; (18)Flash Point: 86.667 °C; (19)Enthalpy of Vaporization: 41.693 kJ/mol; (20)Boiling Point: 198.499 °C at 760 mmHg; (21)Vapour Pressure: 0.506 mmHg at 25 °C.

Preparation of Benzyl bromide: this chemical can be prepared by Benzyloxy-tert-butyl-dimethylsilan. This reaction needs reagent BBr3 and solvent CH2Cl2 at ambient temperature. The reaction time is 10 min. The yield is 90 %.

 Benzyl bromide can be prepared by Benzyloxy-tert-butyl-dimethylsilan.

Uses of Benzyl bromide: (1) It is used in organic synthesis for the introduction of the benzyl protecting group for alcohols and carboxylic acids. It is also used as a war gas. (2) it is used to produce other chemicals. For example, it can react with 4-Acetoxymethyl-pyridine to get 4-Benzyloximethyl-pyridine. The reaction occurs with reagents 18-crown-6, KOH and solvent benzene at ambient temperature. The yield is 87 %.

Benzyl bromide can react with 4-Acetoxymethyl-pyridine to get 4-Benzyloximethyl-pyridine.

When you are dealing with this chemical, you should be very careful. This chemical is inflammation to the skin, eyes and respiratory system or other mucous membranes. Therefore, you should wear eye/face protection and keep out of the reach of children.

You can still convert the following datas into molecular structure:
(1) SMILES: c1ccc(cc1)CBr
(2) InChI: InChI=1S/C7H7Br/c8-6-7-4-2-1-3-5-7/h1-5H,6H2
(3) InChIKey: AGEZXYOZHKGVCM-UHFFFAOYSA-N