Product Name

  • Name

    2-Cyanobenzyl bromide

  • EINECS 231-555-8
  • CAS No. 22115-41-9
  • Article Data22
  • CAS DataBase
  • Density 1.51g/cm3
  • Solubility Slightly soluble in water
  • Melting Point 72-74 °C(lit.)
  • Formula C8H6BrN
  • Boiling Point 264.6 °C at 760 mmHg
  • Molecular Weight 196.046
  • Flash Point 113.8 °C
  • Transport Information UN 3261 8/PG 2
  • Appearance White to light yellow crystal powder
  • Safety 26-36/37/39-45-28A
  • Risk Codes 34
  • Molecular Structure Molecular Structure of 22115-41-9 (2-Cyanobenzyl bromide)
  • Hazard Symbols CorrosiveC
  • Synonyms o-Tolunitrile,a-bromo- (8CI);(2-Cyanophenyl)methyl bromide;1-(Bromomethyl)-2-cyanobenzene;2-(Bromomethyl)benzonitrile;2-Cyano-a-bromotoluene;2-Cyanobenzyl bromide;o-(Bromomethyl)benzonitrile;o-Cyanobenzyl bromide;a-Bromo-2-cyanotoluene;a-Bromo-o-tolunitrile;a-Bromo-o-toluonitrile;
  • PSA 23.79000
  • LogP 2.45318

Synthetic route

2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
With dihydrogen peroxide; bromine In dichloromethane; water for 4h; Reflux;98%
With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 90℃; for 2h;80%
With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 80 - 90℃; for 5.08333h; Inert atmosphere;69%
C14H21NOSi

C14H21NOSi

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
With phosphorus tribromide In dichloromethane at 40℃; for 8h; Time;93%
dicyanozinc
557-21-1

dicyanozinc

1-Bromo-2-bromomethyl-benzene
3433-80-5

1-Bromo-2-bromomethyl-benzene

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,2-Ph2-3,4-bis(2,4,6-(t-Bu)3-phenylphophinidene)cyclobutene; zinc In various solvent(s) at 100℃; for 16h;60%
bicyclo[4.2.0]octa-1(6),2,4-trien-7-one O-(4-(trifluoromethyl)benzoyl) oxime

bicyclo[4.2.0]octa-1(6),2,4-trien-7-one O-(4-(trifluoromethyl)benzoyl) oxime

A

2-cyanobenzyl 4-(trifluoromethyl)benzoate

2-cyanobenzyl 4-(trifluoromethyl)benzoate

B

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
With carbon tetrabromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine; tetrabutylammomium bromide; copper(I) bromide In N,N-dimethyl-formamide at 20℃; for 12h; Schlenk technique; Inert atmosphere;A 52%
B 13%
2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

A

2-(dibromomethyl)benzonitrile
655-63-0

2-(dibromomethyl)benzonitrile

B

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
at 150 - 200℃; bei der Bromierung im Sonnenlicht;
2-cyanobenzylselenocyanate

2-cyanobenzylselenocyanate

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
With hydrogen bromide at 100℃; im Druckrohr;
2-cyanobenzylselenocyanate

2-cyanobenzylselenocyanate

A

2-selanylmethyl-benzonitrile; hydrobromide

2-selanylmethyl-benzonitrile; hydrobromide

B

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
With hydrogen bromide at 100℃; im geschlossenen Rohr;
2-Methylbenzonitrile
529-19-1

2-Methylbenzonitrile

bromine
7726-95-6

bromine

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-cyanobenzylselenocyanate

2-cyanobenzylselenocyanate

hydrogen bromide
10035-10-6, 12258-64-9

hydrogen bromide

A

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

B

hydrobromide of pseudoselenophthalimidein/e

hydrobromide of pseudoselenophthalimidein/e

Conditions
ConditionsYield
at 100℃; im Druckrohr;
...Expand
2-cyanobenzyl chloride
612-13-5

2-cyanobenzyl chloride

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: alcohol
2: fuming hydrobromic acid / 100 °C / im Druckrohr
View Scheme
Multi-step reaction with 2 steps
1: alcohol
2: fuming hydrobromic acid / 100 °C / im geschlossenen Rohr
View Scheme
benzyl bromide
100-39-0

benzyl bromide

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde
120578-03-2

(E)-3-[2-(7-chloro-2-quinolinyl)ethenyl]benzaldehyde

N,N-dimethyl-3-mercaptopropionamide
92065-71-9

N,N-dimethyl-3-mercaptopropionamide

thioacetic acid
507-09-5

thioacetic acid

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
In methanol; hexane; ethyl acetate; trifluoroacetic acid; trifluoroacetic anhydride
...Expand
benzocyclobutenone
3469-06-5

benzocyclobutenone

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydroxylamine hydrochloride; sodium acetate / methanol / 12 h / 75 °C / Inert atmosphere
2: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
3: carbon tetrabromide; copper(I) bromide; tetrabutylammomium bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide / 12 h / 20 °C / Schlenk technique; Inert atmosphere
View Scheme
bicyclo[4.2.0]octa-1(6),2,4-trien-7-one oxime

bicyclo[4.2.0]octa-1(6),2,4-trien-7-one oxime

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere
2: carbon tetrabromide; copper(I) bromide; tetrabutylammomium bromide; N,N,N',N'',N'''-pentamethyldiethylenetriamine / N,N-dimethyl-formamide / 12 h / 20 °C / Schlenk technique; Inert atmosphere
View Scheme
o-bromobenzyl alcohol
18982-54-2

o-bromobenzyl alcohol

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1H-imidazole / dichloromethane / 20 °C
2: tris-(dibenzylideneacetone)dipalladium(0); zinc / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere
3: phosphorus tribromide / dichloromethane / 8 h / 40 °C
View Scheme
((2-bromobenzyl)oxy)(tert-butyl)dimethylsilane
94236-20-1

((2-bromobenzyl)oxy)(tert-butyl)dimethylsilane

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tris-(dibenzylideneacetone)dipalladium(0); zinc / N,N-dimethyl-formamide / 6 h / 100 °C / Inert atmosphere
2: phosphorus tribromide / dichloromethane / 8 h / 40 °C
View Scheme
piperidine
110-89-4

piperidine

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-Piperidinomethyl-benzonitril
135277-08-6

2-Piperidinomethyl-benzonitril

Conditions
ConditionsYield
In diethyl ether for 8h;100%
2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-(bromomethyl)benzaldehyde
60633-91-2

2-(bromomethyl)benzaldehyde

Conditions
ConditionsYield
Stage #1: 2-(bromomethyl)benzonitrile With diisobutylaluminium hydride In n-heptane; dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;
Stage #2: With hydrogen bromide In n-heptane; dichloromethane at 0℃; for 1h; Inert atmosphere;		100%
With diisobutylaluminium hydride In n-heptane; dichloromethane at 0 - 20℃; for 3h; Reduction;97%
With diisobutylaluminium hydride In n-heptane; dichloromethane at 20℃; for 3.5h; Inert atmosphere; Cooling with ice;97%
C21H33NO2
1088482-37-4

C21H33NO2

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

N-(2'-cyanobenzyl)-N,N-dimethyl-N-{(1S)-1-[(-)-8-phenylmenthyloxycarbonylethyl]}ammonium bromide
1088481-89-3

N-(2'-cyanobenzyl)-N,N-dimethyl-N-{(1S)-1-[(-)-8-phenylmenthyloxycarbonylethyl]}ammonium bromide

Conditions
ConditionsYield
In acetonitrile at 20℃; for 48h;100%
N-methylmethane sulphonamide
1184-85-6

N-methylmethane sulphonamide

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

N-(2-cyano-benzyl)-N-methyl-methanesulfonamide
1257706-19-6

N-(2-cyano-benzyl)-N-methyl-methanesulfonamide

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 18h;100%
1-hydroxy-3,6,7-tris(methoxymethoxy)-9H-xanthen-9-one
1314917-55-9

1-hydroxy-3,6,7-tris(methoxymethoxy)-9H-xanthen-9-one

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

C27H25NO9
1314917-91-3

C27H25NO9

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 6h;100%
benzyl 2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-2-(perfluorophenylsulfonamido)acetamido)benzoate
1455006-14-0

benzyl 2-(benzyloxy)-4-(N-(4-cyclohexylbenzyl)-2-(perfluorophenylsulfonamido)acetamido)benzoate

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

benzyl 2-(benzyloxy)-4-(2-(N-(2-cyanobenzyl)-2,3,4,5,6-pentafluorophenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate
1455006-33-3

benzyl 2-(benzyloxy)-4-(2-(N-(2-cyanobenzyl)-2,3,4,5,6-pentafluorophenylsulfonamido)-N-(4-cyclohexylbenzyl)acetamido)benzoate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; Inert atmosphere;100%
3-mercapto-5H-1,2,4-triazino[5,6-b]indole
28668-95-3

3-mercapto-5H-1,2,4-triazino[5,6-b]indole

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

3-((2’-cyanobenzyl)thio)-5H-[1,2,4]triazino[5,6-b]indole
292057-70-6

3-((2’-cyanobenzyl)thio)-5H-[1,2,4]triazino[5,6-b]indole

Conditions
ConditionsYield
With triethylamine In methanol at 20℃; for 16h;100%
(2-cyanophenyl)carbamic acid ethyl ester
41534-70-7

(2-cyanophenyl)carbamic acid ethyl ester

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

ethyl (2-cyanobenzyl)(2-cyanophenyl)carbamate

ethyl (2-cyanobenzyl)(2-cyanophenyl)carbamate

Conditions
ConditionsYield
Stage #1: (2-cyanophenyl)carbamic acid ethyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: 2-(bromomethyl)benzonitrile In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere;		100%
2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

ethanethiol
75-08-1

ethanethiol

2-Ethylsulfanylmethyl-benzonitrile
176983-04-3

2-Ethylsulfanylmethyl-benzonitrile

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran for 5h;99%
6,7-dimethoxy-1-(2',2'-diphenyl-1'-ethenyl)-3,4-dihydroisoquinoline
537040-39-4

6,7-dimethoxy-1-(2',2'-diphenyl-1'-ethenyl)-3,4-dihydroisoquinoline

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-(2-cyanobenzyl)-1-(2',2'-diphenyl-1-ethenyl)-6,7-dimethoxy-3,4-dihydroisoquinolinium bromide

2-(2-cyanobenzyl)-1-(2',2'-diphenyl-1-ethenyl)-6,7-dimethoxy-3,4-dihydroisoquinolinium bromide

Conditions
ConditionsYield
In diethyl ether99%
2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

5,6-dimethyl-2-mercaptobenzimidazole
3287-79-4

5,6-dimethyl-2-mercaptobenzimidazole

2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile

2-((5,6-dimethylbenzimidazole-2-ylthio)methyl)benzenecarbonitrile

Conditions
ConditionsYield
With triethylamine In N-methyl-acetamide; water99%
4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid

4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylic acid

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

(2-cyanophenyl)methyl 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylate

(2-cyanophenyl)methyl 4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-2-oxo-3,4-dihydropyridine-5-carboxylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 18h;99%
dimethyl amine
124-40-3

dimethyl amine

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

2-((dimethylamino)methyl)benzonitrile
53369-76-9

2-((dimethylamino)methyl)benzonitrile

Conditions
ConditionsYield
In diethyl ether; water at 20℃;98%
In benzene
In diethyl ether
In diethyl ether for 8h;
In N,N-dimethyl-formamide at 20℃; for 10h;
ethyl (RS)-2-(benzylideneamino)propanoate
60930-36-1

ethyl (RS)-2-(benzylideneamino)propanoate

2-(bromomethyl)benzonitrile
22115-41-9

2-(bromomethyl)benzonitrile

ethyl (RS)-2-(benzylideneamino)-3-(2-cyanophenyl)-2-methylpropanoate
1142954-12-8

ethyl (RS)-2-(benzylideneamino)-3-(2-cyanophenyl)-2-methylpropanoate

Conditions
ConditionsYield
With potassium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In dichloromethane98%

2-Cyanobenzyl bromide Specification

The IUPAC name of o-Cyanobenzyl bromide is 2-(bromomethyl)benzonitrile. With the CAS registry number 22115-41-9, it is also named as benzonitrile, 2-(bromomethyl)-. The product's categories are benzyl bromide; benzyl; cyanide. It is white to light yellow crystal powder which should be sealed in the container and stored in the cool and dry place.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.36; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.36; (4)ACD/LogD (pH 7.4): 2.36; (5)ACD/BCF (pH 5.5): 36.34; (6)ACD/BCF (pH 7.4): 36.34; (7)ACD/KOC (pH 5.5): 455.51; (8)ACD/KOC (pH 7.4): 455.51; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.588; (13)Molar Refractivity: 43.67 cm3; (14)Molar Volume: 129.7 cm3; (15)Polarizability: 17.31×10-24 cm3; (16)Surface Tension: 49.5 dyne/cm; (17)Enthalpy of Vaporization: 50.25 kJ/mol; (18)Vapour Pressure: 0.00961 mmHg at 25°C; (19)Rotatable Bond Count: 1; (20)Exact Mass: 194.968362; (21)MonoIsotopic Mass: 194.968362; (22)Topological Polar Surface Area: 23.8; (23)Heavy Atom Count: 10; (24)Complexity: 147.

Preparation of o-Cyanobenzyl bromide: It can be obtained by 2-methyl-benzonitrile. This reaction needs reagent NBS and AIBN and solvent CCl4 at temperature of 90 °C. The reaction time is 2 hours. The yield is 80%. 

Uses of o-Cyanobenzyl bromide: It reacts with pyrrolidine to get 2-(1-Pyrrolidinyl-methyl)benzonitril. This reaction needs reagent solvent diethyl ether. The reaction time is 8 hours. The yield is 88 %.

When you are using this chemical, please be cautious about it as the following:
It can cause burns. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. After contact with skin, wash immediately with plenty of soap-suds. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure.
1. SMILES:BrCc1ccccc1C#N
2. InChI:InChI=1/C8H6BrN/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5H2 
3. InChIKey:QGXNHCXKWFNKCG-UHFFFAOYAX

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