4-(CHLOROMETHYL)BENZYL ALCOHOL 99 Chemical Properties

Melting point:

58-60 °C (lit.)

Boiling point:

276℃

Density 

1.195

Flash point:

123℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

wooly solid

pka

14.27±0.10(Predicted)

color 

White

InChI

InChI=1S/C8H9ClO/c9-5-7-1-3-8(6-10)4-2-7/h1-4,10H,5-6H2

InChIKey

OGALXJIOJZXBBP-UHFFFAOYSA-N

SMILES

C1(CO)=CC=C(CCl)C=C1

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 1759 8/PG 2

WGK Germany 

3

HS Code 

2906290090

4-(CHLOROMETHYL)BENZYL ALCOHOL 99 Usage And Synthesis

Uses

4-(Chloromethyl)benzyl alcohol may be used in the synthesis of 4-(chloromethyl)benzyl acetate.

General Description

4-(Chloromethyl)benzyl alcohol can be synthesized from 4-(chloromethyl)benzoyl chloride.

Synthesis

Example 1: (1) Synthesis of [4-(chloromethyl)benzyl]alcohol: To a solution of tetrahydrofuran containing 4-(chloromethyl)benzoic acid (60 mL THF), 1M borane-THF solution (90 mL) was slowly added. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, methanol (50 mL) was added to quench the reaction. Subsequently, the solvent was removed by rotary evaporator and the obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate = 4/1 to 3/1) to afford 4-(chloromethyl)benzyl alcohol (8.84 g, 96% yield) as a colorless solid.

References

[1] Patent: WO2003/106403, 2003, A1. Location in patent: Page 23
[2] Patent: US5387709, 1995, A
[3] Patent: WO2015/51045, 2015, A2. Location in patent: Page/Page column 161-162
[4] Patent: US2016/215288, 2016, A1. Location in patent: Paragraph 0602; 0611
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4481 - 4486

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