Benzyl Alcohol

Other Names:

Phenylmethanol

Phenylcarbinol

Benzenemethanol

BnOH

General Information:

Structure:

CAS Number: 100-51-6

Molecular Weight: 108.14 g/mol

Appearance: Colorless liquid

Melting Point: -15 C

Boiling Point: 205 C

Density: 1.045 g/mL at 25 C

Acidity (pKa): 15.40

Benzyl alcohol is generally used as a reagent in organic chemistry, although in some other industries it finds common use as a solvent.

Common Uses:

Nucleophilic reagent for SNAr reactions

Procedure excerpt:

To a solution of NaH (60% in mineral oil) (1.75 equiv) in DMF (0.5 M) was added benzyl alcohol (2.5 equiv) dropwise. After stirring 30 min, the aryl chloride . . .

[full procedure]

Reagent for forming Cbz protected amines in Curtius rearrangements

Procedure excerpt:

. . . the SM (1.45 g, 7.31 mmol) and TEA (1.02 mL, 7.31 mmol) in toluene (15 mL). The mixture was stirred at 90 C for 2 h. Then, benzyl alcohol (0.75 mL, 7.31 mmol) was added . . .

[full procedure]

Safety:

Benzyl alcohol is highly irritating and damaging to the eye. It is not known to be a carcinogen, teratogen, or reproductive hazard. Benzyl alcohol has a low acute toxicity.

References:

1) Patent Reference: WO2010026121, page 59, (3.6 MB)

2) Patent Reference: WO2016020526, page 58, (5.6 MB)

3) Wikipedia: Benzyl alcohol (link)

4) www.sigmaaldrich.com: Benzyl alcohol (link)

5) www.alfa.com: 41218 Benzyl alcohol, ACS, 99+% (link)