Formaldehyde

Other Names:

Formalin

Methanal

Methyl aldehyde

General Information:

Structure:

CAS Number: 50-00-0

Molecular Weight: 30.03 g/mol

Appearance: Colorless gas (at room temperature)

Formaldehyde is the simplest aldehyde.

Common Uses:

Reagent for reductive methylation (reductive amination) of amines

Procedure excerpt:

To a mixture of the SM (115 mg, 0.36 mmol) and formaldehyde (aq, excess) in MeOH (10 mL) was added NaBH(OAc)3 (382 mg, 1.80 mmol) at RT. The reaction mixture . . .

[full procedure]

Reagent in Pictet-Spengler reactions

Procedure excerpt:

A solution of the SM (165 g, 1.0 mol) and aq formaldehyde (37 wt%, 30 g, 1.0 mol) in formic acid (1.5 L) was stirred at 50 C overnight. The solvent was removed in vacuo to provide . . .

[full procedure]

Reagent in the hydroxymethylation of Grignard reagents to give primary alcohols

Safety:

Formaldehyde is a known carcinogen and is highly toxic to all animals.

References:

1) Patent Reference: WO2016011390, page 65, (20.2 MB)

2) Patent Reference: WO2016014463, page 91, (6.7 MB)

3) Coates, R. M.; Denmark, S. E.; Handbook of Reagents for Organic Synthesis, Reagents, Auxiliaries, and Catalysts for C-C Bond Formation

4) Wikipedia: Formaldehyde (link)

5) www.sigmaaldrich.com: Formaldehyde solution - 37 wt. % in H2O (link)