ChemicalBook > CAS DataBase List > 2-Cyanobenzyl bromide

2-Cyanobenzyl bromide

Product Name: 2-Cyanobenzyl bromide
CAS No.: 22115-41-9
Chemical Name: 2-Cyanobenzyl bromide
Synonyms: 2-(BROMOMETHYL)BENZONITRILE;ALPHA-BROMO-O-TOLUNITRILE;Ortho Cyano Benzyl Bromide;AKOS 92624;Alogliptin-2;AKOS BBS-00000052;Cyanobenzyl bromide;α-Bromo-o-toluntrile;2-cynobenzyl bromide;A-BROMO-O-TOLUNITRILE
CBNumber: CB3241402
Molecular Formula: C8H6BrN
Formula Weight: 196.04
MOL File: 22115-41-9.mol

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2-Cyanobenzyl bromide Property

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)

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Safety

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

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

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

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

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

P363Wash contaminated clothing before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 144711
Product name: 2-(Bromomethyl)benzonitrile
Purity: ≥97%
Packaging: 5g
Price: $50.6
Updated: 2025/07/31

Sigma-Aldrich

Product number: 144711
Product name: 2-(Bromomethyl)benzonitrile
Purity: ≥97%
Packaging: 25g
Price: $165
Updated: 2025/07/31

TCI Chemical

Product number: C1556
Product name: 2-Cyanobenzyl Bromide
Purity: >98.0%(GC)
Packaging: 10g
Price: $61
Updated: 2025/07/31

TCI Chemical

Product number: C1556
Product name: 2-Cyanobenzyl Bromide
Purity: >98.0%(GC)
Packaging: 25g
Price: $119
Updated: 2025/07/31

Sigma-Aldrich

Product number: 144711
Product name: 2-(Bromomethyl)benzonitrile
Purity: ≥97%
Packaging: 100g
Price: $237
Updated: 2023/01/07

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2-Cyanobenzyl bromide Chemical Properties,Usage,Production

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

Synthesis

529-19-1

22115-41-9

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-Cyanobenzyl bromide manufacturers

Hefei Lbao Physical & Chemical Science Co.,Ltd

Product: 2-Cyanobenzyl bromide 22115-41-9
Price: US $0.00/kg
Min. Order: 1kg
Purity: 98%
Supply Ability: Customise
Release date: 2025-10-31

WUHAN FORTUNA CHEMICAL CO., LTD

Product: 2-Cyanobenzyl bromide 22115-41-9
Price: US $0.00/KG
Min. Order: 1KG
Purity: 98%min
Supply Ability: 30tons/month
Release date: 2023-04-07

Hebei Yanxi Chemical Co., Ltd.

Product: 2-Cyanobenzyl bromide 22115-41-9
Price: US $30.00-13.00/kg
Min. Order: 1kg
Purity: 0.99
Supply Ability: 10 tons
Release date: 2023-11-23

22115-41-9, 2-Cyanobenzyl bromideRelated Search:

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

Adjacent cyano benzyl broMide

O-CYANOBENZYL BROMIDE

ALPHA-BROMO-O-TOLUNITRILE

ALPHA-BROMO-O-TOLUONITRILE

AKOS 92624

AKOS BBS-00000052

A-BROMO-O-TOLUNITRILE

alpha-bromo-ortho-tolunitrile

2-CYANOBENZYL BROMIDE

2-(BROMOMETHYL)BENZONITRILE

2-Cyanobenzyl bromide 2-(Bromomethyl)benzonitrile

o-Cyanobenzyl Bromid 2-(Bromomethyl)Benzonitrile

Alogliptin-2

2-(Bromomethyl)benzonitrile >=97%

α-Bromo-o-toluntrile

a-Bromo-o-tolunitrile, (2-Cyanobenzyl bromide)

ALPHA-BROMO-ORTHO-TOLUNITRILE, 97+%

Alpha-Bromo-O-Tolunitrile98%

Benzonitrile, 2-(bromomethyl)-

à-bromo-o-tolunitrile

α-bromo-o-tolunitrile

2-Cyanobenzyl bromide 98%

2-Cyanobenzylbromide98%

2-CYANIDE BENZYL BROMIDE 99+%

2-(Bromomethyl)benzonitrile, 97% - (See B24278)

α-Bromo-o-tolunitrile, 2-Cyanobenzyl bromide

2-(bromomethy)benzonitrile

2-(Bromomethyl)benzonitrile,98%

α-Bromo-o-tolunitrile ,97%

-Cyano benzyl broMide (O-Cyano benzyl broMide)

2-(Bromomethyl)benzonitrile 98%

2-(Bromomethyl)benzonitrile alpha-Bromo-o-tolunitrile

o-(Bromomethyl)benzonitrile

(2-Cyanophenyl)Methyl broMide

2-CyanobenzylBromide&gt

Cyanobenzyl bromide

Ortho Cyano Benzyl Bromide

alogliptin impurities160

alogliptin impurities13

alpha-Bromo-o-tolunitrile,2-Cyano benzyl bromide

1-Pyrrolidinepropanoicacid,2,11-dioxo-

Alpha bromo toluoyl nitrile

(2-Cyanophenyl)methyl bromide (Alogliptin Impurity)

Alogliptin intermediate 2-Cyanobenzyl bromide

2-cynobenzyl bromide

Alogliptin Impurity 02

22115-41-9

22115-14-9

2215-41-9

BrCH2C6H4CN

Cyanides/Nitriles

Organic Building Blocks

Nitrogen Compounds

C8 to C9

Building Blocks

cyanide| alkyl bromide

22115-41-9