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Acetonitrile


Other Names:

ACN

Methyl cyanide






General Information:


Structure:



CAS Number: 75-05-8

Molecular Weight: 41.05 g/mol

Appearance: Colorless liquid

Chemical Formula: CH3CN

Melting Point: -48 C

Boiling Point: 80-82 C

Density: 0.786 g/mL


Acetonitrile (ACN) is a polar aprotic solvent used for a variety of different reactions. Common reactions employing ACN as a solvent include substitutions, SNAr reactions, brominations, and iodinations. Acetonitrile is also widely used as part of the mobile phase in HPLC and LCMS. The use of ACN as a reagent is not very common, but one example is in Ritter reactions.




Common Uses:


Solvent for reactions





Solvent (mobile phase) for reverse phase purifications



Procedure excerpt:

…it was concentrated and purified by reverse phase HPLC (20-95% 0.1% TFA/ACN in 0.1% TFA/H2O) to provide the product as a yellow…




Reagent in Ritter reactions





Safety:


Acetonitrile (ACN) is slightly/moderately toxic. It can be metabolized in the body to hydrogen cyanide, but cases of acetonitrile poisoning are not common. Acetonitrile is highly flammable.




References:


1) WO2016011930, page 173

2) WO2012129338, page 151

3) Wikipedia: Acetonitrile (link)

4) www.sigmaaldrich.com: Acetonitrile (link)

5) www.alfa.com: A19862 Acetonitrile, 99% (link)

6) Kurti, L.; Czako, B.; Strategic Applications of Named Reactions in Organic Synthesis