4-Bromobenzoylacetonitrile Chemical Properties

Melting point:

161-163

Boiling point:

370.0±27.0 °C(Predicted)

Density 

1.523±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

form 

solid

pka

7.37±0.10(Predicted)

Appearance

Light yellow to yellow Solid

InChI

1S/C9H6BrNO/c10-8-3-1-7(2-4-8)9(12)5-6-11/h1-4H,5H2

InChIKey

HSNWUXWZCSDJPL-UHFFFAOYSA-N

SMILES

Brc1ccc(cc1)C(=O)CC#N

CAS DataBase Reference

4592-94-3(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2926907090

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

4-Bromobenzoylacetonitrile Usage And Synthesis

Uses

4-Bromobenzoylacetonitrile is a useful research chemical used in the preparation of mechanistic studies, and fluorescence of naphtho[1,8-bc]pyrans via rhodium-catalyzed cascade oxidative annulation of benzoylacetonitriles with internal alkynes.

Synthesis

4-Bromobenzoylacetonitrile can be prepared from 3-bromobenzoic acid as a reaction material, the intermediate 3-bromobenzoic acid methyl ester is prepared first, and 4-bromobenzoylacetonitrile is generated under the action of sodium cyanide.

Purification Methods

The nitrile is purified by dissolving in slightly alkaline H2O (charcoal), filtering and acidifying with HCl to give colourless needles (m 162-163o). It recrystallises from EtOH. With Me2SO4/KOH at 130o it gives 4-bromo-methoxycinnamylnitrile m 58.5-59.5o (from high boiling pet ether) [Fuson & Wolf J Am Chem Soc 61 1940 1939, Grathaus & Dains J Am Chem Soc 58 1334 1936]. [Beilstein 10 III 2998.]

4-Bromobenzoylacetonitrile(4592-94-3)Related Product Information

• Bromoxynil octanoate
• 2-Bromofluorobenzene
• 4'-Bromopropiophenone
• 3-Bromoanisole
• Benzoylacetonitrile
• Bromoxynil
• Bromobenzyl cyanide
• (3-Methoxyphenyl)acetonitrile
• cyanoacetaldehyde
• 2-BROMOBENZOYLACETONITRILE
• 2-[(DIMETHYLAMINO)METHYLENE]-3-(4-BROMOPHENYL)-3-OXO-PROPANENITRILE
• 3-(4-BROMO-1-NAPHTHYL)-3-OXOPROPANENITRILE
• 3-(4-Bromo-2-fluorophenyl)-3-oxopropanenitrile
• 3-BROMOBENZOYLACETONITRILE
• 4-Bromobenzoylacetonitrile
• AURORA KA-7439
• AURORA 13454
• AURORA KA-7445