271004

Sigma-Aldrich

Acetonitrile

anhydrous, 99.8%

Synonym(s):
Cyanomethane, Methyl cyanide, ACN, Ethyl nitrile
Linear Formula:
CH3CN
CAS Number:
Molecular Weight:
41.05
Beilstein/REAXYS Number:
741857
EC Number:
MDL number:
eCl@ss:
39031501
PubChem Substance ID:
NACRES:
NA.21

Quality Level

grade

anhydrous

vapor density

1.41 (vs air)

vapor pressure

72.8 mmHg ( 20 °C)

assay

99.8%

form

liquid

autoignition temp.

973 °F

expl. lim.

16 %

application(s)

solid phase extraction (SPE): suitable

impurities

<0.001% water
<0.005% water (100 mL pkg)

evapn. residue

<0.0005%

color

colorless

refractive index

n20/D 1.344 (lit.)

bp

81-82 °C (lit.)

mp

−45 °C (lit.)

solubility

water: soluble (completely)

density

0.786 g/mL at 25 °C (lit.)

SMILES string

CC#N

InChI

1S/C2H3N/c1-2-3/h1H3

InChI key

WEVYAHXRMPXWCK-UHFFFAOYSA-N

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General description

Acetonitrile, an aliphatic nitrile, is widely used as an organic solvent and intermediate in organic syntheses. It is transparent to UV-visible light, which makes it highly applicable in spectrophotometric and fluorimetric techniques. MeCN is utilized as a mobile phase component in many chromatographic techniques, due to its low viscosity, high elution strength and miscibility in water. It also plays a major role as an extractant medium in liquid-liquid extraction, solid-phase extraction or microextraction.

Application

Acetonitrile may be used as a solvent to prepare:
  • 1,2-Azidoalcohols and 1,2-azidoamines via cerium(III) chloride assisted ring opening of epoxides and aziridines by sodium azide.
  • Cyano-bearing indolinones by oxidative arylalkylation of olefins in the presence of palladium catalyst.

It may also be used as a reactant to synthesize:
  • Bis (diphenylphosphino) acetonitrile by reacting with n-butyllithium and then with chlorodiphenylphosphine.
  • β-Acetamido ketones via coupling reaction with ketones or ketoesters and aldehydes in the presence of cobalt(II) chloride.

Packaging

1, 6×1, 2, 4×2 L in Sure/Seal™
100, 12×100 mL in Sure/Seal™
200 L in Pure-Pac™ 1
18 L in Pure-Pac™ 1
20, 50 L in Pure-Pac™ 2

pictograms

FlameExclamation mark

signalword

Danger

hazcat

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Flam. Liq. 2

storage_class_code

3 - Flammable liquids

WGK Germany

WGK 2

Flash Point F

35.6 °F - closed cup

Flash Point C

2.0 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Bis (diphenylphosphino) acetonitrile: Synthesis, ligand properties and application in catalytic carbon?carbon coupling
Braun L, et al.
Dalton Transactions, 14, 1409-1415 (2007)
Cobalt-catalysed three-component coupling involving ketones or ketoesters, aldehydes and acetonitrile: a novel one-pot synthesis of ?-acetamido ketones
Madhavaa Reddy M.
Journal of the Chemical Society. Chemical Communications, 6, 713-714 (1994)
Eagleson M.
Concise Encyclopedia Chemistry, 56-56 (1994)
Cerium (III) chloride promoted highly regioselective ring opening of epoxides and aziridines using NaN3 in acetonitrile: a facile synthesis of 1,2-azidoalcohols and 1,2-azidoamines.
Sabitha G, et al.
Organic Letters, 4(3), 343-345 (2002)
Palladium-Catalyzed Oxidative Arylalkylation of Activated Alkenes: Dual C-H Bond Cleavage of an Arene and Acetonitrile.
Wu T, et al.
Angewandte Chemie (International Edition in English), 50(52), 12578-12581 (2011)
Articles
Amide bonds are ubiquitous in both nature and industrial applications. They are vital to the structure and function of biological macromolecules and polymers. The importance of this functionality has resulted in numerous approaches to its formation, ranging from stoichiometric activation of carboxylic acids to more recent advances in catalytic amide bond formation.
Read More

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