3-ACETYLBENZONITRILE Chemical Properties

Melting point:

98-100 °C (lit.)

Boiling point:

120 °C (5 mmHg)

Density 

1.1555 (rough estimate)

refractive index 

1.4500 (estimate)

Flash point:

120°C/5mm

storage temp. 

Sealed in dry,Room Temperature

solubility 

4g/l

form 

Powder

color 

Pale yellow-orange to brown

Water Solubility 

Insoluble in water.

BRN 

2079629

InChI

InChI=1S/C9H7NO/c1-7(11)9-4-2-3-8(5-9)6-10/h2-5H,1H3

InChIKey

SBCFGFDAZCTSRH-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

6136-68-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-37/39

RIDADR 

3439

WGK Germany 

3

Hazard Note 

Harmful/Irritant

TSCA 

T

HazardClass 

6.1

PackingGroup 

III

HS Code 

29269090

Storage Class

11 - Combustible Solids

Hazard Classifications

Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

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

3-ACETYLBENZONITRILE Usage And Synthesis

Uses

3-Acetylbenzonitrile has been used in the preparation of 3-(hydroxyacetyl)benzonitrile, and 3-(1-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenylimino)ethyl)benzonitrile.

Description

3-Acetylbenzonitrile is a pharmaceutical intermediate compound. As its molecular structure contains both cyano (-CN) and acetyl (-COCH₃) functional groups, it is frequently used as a core building block for the synthesis of various bioactive heterocyclic compounds, such as sodium channel blockers. Furthermore, it can also be used in the preparation of OLED materials.

Chemical Properties

Pale yellowish-orange to brown powder

Uses

Preparation of (q2-2-Acetyl-4-cyanophenyl)tetra- carbonylmanganese by Reaction of 3-Acetylbenzonitrile with Benzylpentacarbonylmanganese. Four aromatic amidoximes were synthesized by reacting hydroxylamine with 1,3 -dicyanobenzene, 1,4- dicyanobenzene, 3-acetylbenzonitrile, and 4-acetylbenzonitrile. Darzens condensation of 3-acetylbenzonitrile provided aldehyde.

Uses

3-Acetylbenzonitrile has been used in the preparation of:

• 3-(hydroxyacetyl)benzonitrile
• 3-(1-(3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylphenylimino)ethyl)benzonitrile

Definition

ChEBI: 3-Acetylbenzonitrile is an aromatic ketone.

Reactions

The reaction of 3-Acetylbenzonitrile and substituted benzaldehyde can be used for the synthesis of substituted 3-((E)-3-substituted phenylacryloyl)benzonitriles^[1].

Synthesis Reference(s)

Tetrahedron Letters, 28, p. 2053, 1987 DOI: 10.1016/S0040-4039(00)96043-X

Synthesis

The preparation of 3-acetylbenzonitrile is usually achieved by the following steps: starting from benzoic acid, reacting with acetyl chloride to produce 3-acetylbenzoic acid. 3-acetylbenzoic acid is converted into 3-acetylbenzonitrile by decarboxylation.

References

[1] D. KAMALAKKANNAN . Synthesis and assessment of substituent effect of some 3-((E)-3-substituted phenylacryloyl)benzonitriles[J]. Journal of Molecular Structure, 2022. DOI:10.1016/j.molstruc.2022.133218.

3-ACETYLBENZONITRILE(6136-68-1)Related Product Information

• 1,4-DIAMINO-2,3-DICYANO-9,10-ANTHRAQUINONE
• 3-(2-Bromoacetyl)benzonitrile
• 6-Cyano-1-indanone
• 2,3-dihydro-1-oxo-1H-indene-4-carbonitrile
• 3-ACETYLBENZONITRILE
• 4-Acetylbenzonitrile
• 2-ACETYLBENZONITRILE
• 4-ACETYLBENZONITRILE,P-ACETYLBENZONITRILE
• Benzonitrile
• Acetophenone
• 3'-CYANO-2-PHENYLACETOPHENONE
• 3-CYANO-4'-METHOXYBENZOPHENONE
• 3-[(E)-3-(DIMETHYLAMINO)-2-PROPENOYL]BENZENECARBONITRILE
• 2-(2-BROMOPHENYL)-3'-CYANOACETOPHENONE
• 3-CYANO-3'-IODOBENZOPHENONE
• 3-CYANO-4'-IODOBENZOPHENONE
• 7-(3-CYANOPHENYL)-7-OXOHEPTANENITRILE
• 4-(3-CYANOPHENYL)-4-OXOBUTYRONITRILE