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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:
  • (R)-(fi)-alpha-methoxy-alpha-trifluoromethylphenylacetylchloride
  • (R)-(-)-alpha-Methoxy-alpha-(trifluoromethyl)phenylacetyl chloride, 98+%
  • (R)-(-)-MTPA-Cl, Moshers acid chloride
  • (S)-2-Methoxy-2-phenyl-3,3,3-trifluoropropionic acid chloride
  • (S)-2-Methoxy-3,3,3-trifluoro-2-phenylpropionic acid chloride
  • (S)-2-Phenyl-2-methoxy-3,3,3-trifluoropropionic acid chloride
  • [S,(+)]-α-Methoxy-α-(trifluoromethyl)benzeneacetic acid chloride
  • (R)-(-)-^a-Methoxy-^a-(trifluoromethyl)phenylacetyl chloride, 98+%
CAS:
39637-99-5
MF:
C10H8ClF3O2
MW:
252.62
EINECS:
621-758-4
Product Categories:
  • Analytical Chemistry
  • e.e. / Absolute Configuration Determination (NMR)
  • Enantiomer Excess & Absolute Configuration Determination
Mol File:
39637-99-5.mol
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(S)-(+)-ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETYL CHLORIDE Chemical Properties

Boiling point:
213-214 °C(lit.)
alpha 
D25 -10.0± 0.1° (neat, l = 1)
Density 
1.35 g/mL at 25 °C(lit.)
refractive index 
n20/D 1.469(lit.)
Flash point:
194 °F
storage temp. 
Inert atmosphere,Store in freezer, under -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 
Sparingly miscible with water.
Sensitive 
Moisture Sensitive
Merck 
14,6280
BRN 
3591565
CAS DataBase Reference
39637-99-5(CAS DataBase Reference)
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Safety Information

Hazard Codes 
C
Risk Statements 
34
Safety Statements 
26-27-36/37/39-45
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

(R)-(-)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride is used as a chiral acylating reagent, which is used in the resolution of amino acid enantiomers like 2,5-dimethoxy-4-methylamphetamine. It is also suitable for the determination of the optical composition of compounds extracted from biological fluids.

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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