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

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(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE Basic information

Product Name:
(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE
Synonyms:
  • (+)-ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)PHENYLACETYL CHLORIDE
  • (S)-(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, 98+%
  • (S)-(+)-MTPA-Cl, Moshers acid chloride
  • (S)-(+)-^a-Methoxy-^a-(trifluoromethyl)phenylacetyl chloride, 98+%
  • (S)-(+)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride,99%
  • (R)-(-)-A-METHOXY-A-(TRIFLUOROMETHYL)PHENYLACETYL CHLORIDE
  • (R)-(-)-ALPHA-METHOXY-ALPHA-(TRIFLUOROMETHYL)BENZENEACETYLCHLORIDE
  • R(-)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID CHLORIDE
CAS:
20445-33-4
MF:
C10H8ClF3O2
MW:
252.62
EINECS:
633-847-5
Product Categories:
  • Analytical Chemistry
  • e.e. / Absolute Configuration Determination (NMR)
  • Enantiomer Excess & Absolute Configuration Determination
Mol File:
20445-33-4.mol
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(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)
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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
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 CHLORIDESupplier

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