ChemicalBook--->CAS DataBase List--->165111-46-6

165111-46-6

165111-46-6 Structure

165111-46-6 Structure
IdentificationBack Directory
[Name]

Methyl 2-bromomethyl-4-cyanobenzoate
[CAS]

165111-46-6
[Synonyms]

Methyl 2-bromomethyl-4-cyanobenzoate
Benzoic acid, 2-(bromomethyl)-4-cyano-, methyl ester
[Molecular Formula]

C10H8BrNO2
[MDL Number]

MFCD09864855
[MOL File]

165111-46-6.mol
[Molecular Weight]

254.08
Chemical PropertiesBack Directory
[Boiling point ]

380.5±37.0 °C(Predicted)
[density ]

1.53±0.1 g/cm3(Predicted)
[storage temp. ]

under inert gas (nitrogen or Argon) at 2-8°C
[Appearance]

White to off-white Solid
[InChI]

InChI=1S/C10H8BrNO2/c1-14-10(13)9-3-2-7(6-12)4-8(9)5-11/h2-4H,5H2,1H3
[InChIKey]

QMLVCVLSZNSKJM-UHFFFAOYSA-N
[SMILES]

C(OC)(=O)C1=CC=C(C#N)C=C1CBr
Safety DataBack Directory
[HS Code ]

2916399090
Spectrum DetailBack Directory
[Spectrum Detail]

Methyl 2-bromomethyl-4-cyanobenzoate(165111-46-6)1HNMR
Hazard InformationBack Directory
[Synthesis]

methyl 4-cyano-2-methylbenzoate

103261-67-2

Methyl 2-bromomethyl-4-cyanobenzoate

165111-46-6

General procedure for the synthesis of methyl 2-bromomethyl-4-cyanobenzoate from methyl 4-cyano-2-methylbenzoate: Methyl 4-cyano-2-methylbenzoate (4.0 g, 22.83 mmol) was dissolved in carbon tetrachloride (150 mL) and N-bromosuccinimide (NBS, 4.88 g, 27.4 mmol) was added to form a suspension. The suspension was heated at 80 °C for 5 min. Subsequently, azobisisobutyronitrile (AIBN, 1.88 g, 11.42 mmol) was added and stirred continuously at 80 °C for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and filtered. The filtrate was concentrated to give the crude product. Purification by silica gel column chromatography using a solvent mixture of ethyl acetate (EA) and petroleum ether (gradient elution, 0% to 5% EA) resulted in methyl 2-bromomethyl-4-cyanobenzoate (3.84 g, 66.9% yield) as a white solid.

[References]

[1] Patent: WO2017/201069, 2017, A1. Location in patent: Paragraph 0510
[2] Patent: US5591752, 1997, A
[3] Patent: US2009/82368, 2009, A1. Location in patent: Page/Page column 41-42
[4] Patent: WO2013/79452, 2013, A1. Location in patent: Page/Page column 165
[5] Patent: US2014/45855, 2014, A1. Location in patent: Paragraph 0552
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