Methanol

Other Names:

Methyl alcohol

General Information:

Structure:

CAS Number: 67-56-1

Molecular Weight: 32.04 g/mol

Appearance: Colorless liquid

Melting Point: -98 C

Boiling Point: 64.7 C

Density: 0.791 g/mL at 25 C

Methanol is a common solvent with a wide variety of uses in organic chemistry.

Common Uses:

Reagent in Fisher esterifications

Procedure excerpt:

To a solution of the SM (25.0 g, 127.4 mmol) in MeOH (100 mL) was added a catalytic amount of H2SO4 (~10 drops). The mixture was refluxed overnight, after which time . . .

[full procedure]

Reagent in Pinner reactions

Procedure excerpt:

A solution of the SM (3.8 g, 13.8 mmol) in MeOH (40.0 mL) was saturated with dry HCl gas. The reaction was kept standing for 16 h, after which time the reaction . . .

[full procedure]

Solvent for reactions

Procedure excerpt:

10% Pd/C (2.50 g, 23.5 mmol) was added under a N2 atmosphere to a chilled (ice bath) solution of the SM (15.0 g, 67.5 mmol) in MeOH (400 mL). The flask was . . .

[full procedure]

Solvent for silica gel chromatography

Procedure excerpt:

. . . The crude product was purified by silica gel column chromatography (0-10% MeOH/DCM) to provide the product . . .

[full procedure]

Solvent for triturations

Procedure excerpt:

. . . MeOH (5 mL) and H2O (6 mL) were added to form a slurry which was stirred at RT for 1 h. The resulting solid was filtered to provide the product . . .

[full procedure]

Solvent for recrystallizations

Procedure excerpt:

. . . purified on silica gel (0-10% EtOAc/hexane) to give a white solid. The solid was recrystallized from MeOH to provide the product . . .

[full procedure]

Safety:

Methanol is considered highly toxic to humans. It is metabolized by the body to formic acid. As little as 10 mL methanol can cause permanent blindness, 30-100 mL causes death. Methanol is a highly flammable liquid.

References:

1) Patent Reference: WO2012112946, page 43, (11.2 MB)

2) Patent Reference: WO2014149164, page 234, (23.7 MB)

3) Patent Reference: WO2011014535, page 40, (17.3 MB)

4) Patent Reference: WO2015051043, page 60, (9.7 MB)

5) Patent Reference: WO2012129344, page 132, (7.3 MB)

6) Patent Reference: WO2010045258, page 120, (12.0 MB)

7) Wikipedia: Methanol (link)

8) www.sigmaaldrich.com: Methanol (link)