(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE Chemical Properties

Boiling point:

213-214 °C(lit.)

alpha 

D24 +129.0± 0.2° (c = 5.17 in CCl4)

Density 

1.35 g/mL at 25 °C(lit.)

refractive index 

n20/D 1.47(lit.)

Flash point:

194 °F

storage temp. 

-20°C

form 

Liquid

Specific Gravity

1.353

color 

Clear colorless to light yellow

optical activity

[α]20/D +137±2°, c = 6.4% in carbon tetrachloride

Water Solubility 

Slightly miscible with water.

Sensitive 

Moisture Sensitive

Merck 

14,6280

BRN 

3591564

CAS DataBase Reference

20445-33-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

C

Risk Statements 

34-43

Safety Statements 

26-36/37/39-45-27

RIDADR 

UN 3265 8/PG 2

WGK Germany 

3

F 

10-21

Hazard Note 

Corrosive/Freeze

HazardClass 

8

PackingGroup 

II

HS Code 

29189900

MSDS

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(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE Usage And Synthesis

Chemical Properties

clear colorless to light yellow liquid

Uses

(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride is used in the preparation of natural products and pheromones. It is also employed as a derivatization enantiomeric purity reagent used for the determination of enantiomeric purity of alcohol and amines by gas chromatography.

Uses

Used in the synthesis of natural products and pheromones.

Uses

Resolution of enantiomers primarily of alcohols and amines.

General Description

(S)-(+)-α-Methoxy-α-trifluoromethylphenylacetyl chloride is commonly used as a derivatizing agent in Mosher ester analysis and Mosher amide analysis, which are NMR-based methods for determining the absolute configuration of the chiral carbon center in secondary alcohols and amines, respectively.

Purification Methods

The most likely impurity is the free acid due to hydrolysis and should be checked by IR. If free from acid, then distil, taking care to keep moisture out of the apparatus. Otherwise add SOCl2 and reflux for 5hours and distil it. Note that shorter reflux times result in a higher boiling fraction (b 130-155o/1mm) which has been identified as the anhydride. [Dale et al. J Org Chem 34 2543 1969, for enantiomeric purity see Dale & Mosher J Am Chem Soc 97 512 1973.]

(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE(20445-33-4)Related Product Information

• (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE
• 1-Pentanol
• Phenylacetyl chloride
• 3,3,3-TRIFLUOROPROPIONYL CHLORIDE
• (R)-2-CHLORO-1-PHENYLETHANOL
• 3-CHLORO-1,1,1-TRIFLUOROPROPANE
• (S)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetic acid
• (S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE
• ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE,(+/-)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE
• 4-FLUORO-3-(TRIFLUOROMETHYL)ANISOLE
• 1-CHLORO-2-METHYL-2-PROPANOL
• Methoxyacetyl chloride
• 1-PHENYL-2,2,2-TRIFLUOROETHANOL
• (+/-)-2-CHLORO-1-PHENYLETHANOL
• 1-CHLORO-3-FLUOROISOPROPANOL
• (R)-(+)-alpha-Methoxy-alpha-trifluoromethylphenylacetic acid
• (+/-)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID
• Acetyl chloride