2-Cyanobenzyl bromide Chemical Properties

Melting point:

72-74 °C(lit.)

Boiling point:

111 °C / 1.5mmHg

Density 

1.5466 (rough estimate)

refractive index 

1.6550 (estimate)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

Water Solubility 

Slightly soluble in water

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly)

form 

Crystalline Powder or Chunks

color 

White to gray-brown

BRN 

742605

InChI

InChI=1S/C8H6BrN/c9-5-7-3-1-2-4-8(7)6-10/h1-4H,5H2

InChIKey

QGXNHCXKWFNKCG-UHFFFAOYSA-N

SMILES

C(#N)C1=CC=CC=C1CBr

CAS DataBase Reference

22115-41-9(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45-28A

RIDADR 

UN 3261 8/PG 2

WGK Germany 

3

F 

10-19-21

Hazard Note 

Corrosive

HazardClass 

8

PackingGroup 

II

HS Code 

29269090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

2-Cyanobenzyl bromide Usage And Synthesis

Description

2-(Bromomethyl)benzonitrile reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)meth-yl]benzonitrile. It undergoes base-promoted condensation reaction with homophthalic anhydride to yield 6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-one.

Chemical Properties

White to light yellow crystal powder

Uses

2-(Bromomethyl)benzonitrile is an intermediate in the synthesis of Alogliptin, an oral antihyperglycemic agent that is a selective inhibitor of the enzyme dipeptidyl peptidase-4 (DPP-4). Antidiabetic agent.
Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package.

General Description

2-(Bromomethyl)benzonitrile reacts with 2H-tetrazole in the presence of KOH to yield 4-[(2H-tetra-zol-2-yl)meth-yl]benzonitrile. It undergoes base-promoted condensation reaction with homophthalic anhydride to yield 6,11-dihydro-5H-indeno[1,2-c]isoquinolin-5-one.

Synthesis

General procedure for the synthesis of 2-cyanobenzyl bromide from o-toluonitrile: Azobisisobutyronitrile (AIBN, 29.25 mmol) was added to a solution of 2-methylbenzyl cyanide (325 mmol) and N-bromosuccinimide (NBS, 346 mmol) in carbon tetrachloride (300 mL). The reaction mixture was heated at 90°C for 2 h and subsequently cooled to room temperature. The precipitated solid was removed by filtration and the filtrate was washed with saturated aqueous sodium bicarbonate solution (4 x 120 mL), dried over sodium sulfate and concentrated. The resulting solid was washed with hexane (4 x 500 mL) and dried to give 2-(bromomethyl)benzonitrile in 57% yield as a yellow solid. A solution of 2-(bromomethyl)benzyl cyanide (214 mmol) in dimethyl sulfoxide (40 mL) was slowly added to a solution of ethyl 2-hydroxyacetate (431 mmol) and sodium ethoxide (215 mmol) in dimethyl sulfoxide (14.5 mL) over 90 minutes. The reaction mixture was kept at room temperature for 1 hour, followed by heating at 65°C for 5 hours and finally cooled to room temperature. The reaction mixture was diluted with ice water (50 g), extracted with ether (3 x 500 mL) and the combined organic layers were dried over sodium sulfate and concentrated. The residue was purified by column chromatography (petroleum ether/ethyl acetate, 100:1 to 50:1) to give [(2-cyanobenzyl)oxy]ethyl acetate as a yellow oil.

Purification Methods

Purify the nitrile by steam distillation. Extract the distillate with Et2O, dry the extract (Na2SO4), evaporate and distil the residue. The solidified distillate can be recrystallised from pet ether or cyclohexane. NMR (CDCl3) : 7.8-7.2 (m 4H), 4.62 (s, 2H), IR max 2238 cm1 . [Drory Chem Ber 24 2570 1891, Borsche et al. Chem Ber 74 685 1934, Buckley et al. Aust J Chem 22 594 1969, Beilstein 9 III 2312.] LACHRYMATORY.

References

[1] Organic Process Research and Development, 1998, vol. 2, # 4, p. 261 - 269
[2] Chemistry - A European Journal, 2002, vol. 8, # 9, p. 2000 - 2004
[3] Journal of Organic Chemistry, 2014, vol. 79, # 23, p. 11592 - 11608
[4] Patent: WO2009/55437, 2009, A2. Location in patent: Page/Page column 61; 62
[5] Dyes and Pigments, 2014, vol. 102, p. 63 - 70

2-Cyanobenzyl bromide(22115-41-9)Related Product Information

• Sodium cyanoborohydride
• Benzonitrile
• Sodium bromate
• Methylene dithiocyanate
• Allyl bromide
• Ethidium bromide
• Ethyl N-cyanoethanimideate
• Benzyl bromide
• Rocuronium bromide
• Diethylstilbestrol
• ETHYL 2-CYANOACRYLATE
• α-Bromocinnamaldehyde
• 2-CYANO-4-FLUOROBENZYL BROMIDE
• Benzeneacetonitrile
• 4-Nitrobenzyl bromide
• 2-cyano-5-fluorobenzylbroMide
• Bromine
• Methyl bromide