HEXANENITRILE Chemical Properties

Melting point:

−80 °C(lit.)

Boiling point:

161-164 °C(lit.)

Density 

0.809 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.406(lit.)

Flash point:

110 °F

form 

clear liquid

color 

Colorless to Light yellow

Dielectric constant

17.3（25℃）

InChI

1S/C6H11N/c1-2-3-4-5-6-7/h2-5H2,1H3

InChIKey

AILKHAQXUAOOFU-UHFFFAOYSA-N

SMILES

CCCCCC#N

LogP

1.660

CAS DataBase Reference

628-73-9(CAS DataBase Reference)

EPA Substance Registry System

Hexanenitrile (628-73-9)

Safety Information

Hazard Codes 

Xn

Risk Statements 

10-22-36/37/38

Safety Statements 

36/37

RIDADR 

UN 1993 3/PG 3

WGK Germany 

3

RTECS 

MO3900000

TSCA 

TSCA listed

HS Code 

2926.90.5050

HazardClass 

3.2

PackingGroup 

III

Storage Class

3 - Flammable liquids

Hazard Classifications

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

MSDS

• Language:English Provider:SigmaAldrich

HEXANENITRILE Usage And Synthesis

Application

Acetonitriles belong to the nitrile class of compounds and are important precursor compounds for many products, such as polyamides, pigments and dyes, pharmaceuticals, and agrochemicals. The application of nitrile compounds in the fragrance industry has recently developed rapidly, offering advantages such as long-lasting aroma, stable performance, and non-irritating properties, making them a major class of novel synthetic fragrances. The cyano group in nitrile compounds is easily converted into other functional groups, such as carboxylic acids, amides, aldehydes, and primary amines, and is widely used in the total synthesis research of natural products.

Chemical Properties

Colorless liquid. Melting point -80.3℃, boiling point 163.6℃, 47.2℃ (1.33kPa), relative density 0.8051 (20/4℃), refractive index 1.4068, flash point 43℃. Soluble in ethanol, ether, very slightly soluble in water.

Synthesis Reference(s)

Canadian Journal of Chemistry, 58, p. 2271, 1980 DOI: 10.1139/v80-365
The Journal of Organic Chemistry, 46, p. 4111, 1981 DOI: 10.1021/jo00334a001

Synthesis

Protected by nitrogen, in a 100 mL three-necked flask equipped with a thermometer, anhydrous acetonitrile (10 mL), dimethylsulfoxide (0.03 mmol, 2.5 mg, 0.01 equiv), n-hexanamide (3 mmol, 345 mg, 1.0 equiv), and triethylamine (1.04 mL, 7.5 mmol, 2.5 equiv) were added sequentially, and the temperature was set at room temperature A solution of oxalyl chloride (0.31 mL, 3.6 mmol, 1.2equiv) in anhydrous acetonitrile (5 mL) was slowly added dropwise with a constant pressure dropping funnel. After dropwise addition, continue stirring for 40 min, filtration, filtrate spin dry, add distilled water (15 mL), extract with ethyl acetate (3x 10 mL), combine the organic phases, washed with saturated aqueous sodium chloride solution (30 mL), anhydrous sodium sulfate dry. Filtration, spinning to remove the solvent to obtain the crude product, purified by column chromatography separation (petroleum ether / ethyl acetate = 9:1), to obtain 233 mg of hexanenitrile, the yield was 80%.

Purification Methods

Wash the nitrile twice with half-volumes of conc HCl, then with saturated aqueous NaHCO3, dry over MgSO4, filter and distil it. [Beilstein 2 H 324, 2 I 141, 2 II 286, 2 III 733, 2 IV 930.]

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