369675

Sigma-Aldrich

(S)-(+)-α-Methoxy-α-(trifluoromethyl)phenylacetyl chloride

99%

Synonym(s):
(S)-(+)-MTPA-Cl, Mosher’s acid chloride
Linear Formula:
C6H5C(OCH3)(CF3)COCl
CAS Number:
Molecular Weight:
252.62
Beilstein/REAXYS Number:
3591562
MDL number:
PubChem Substance ID:
NACRES:
NA.22
Pricing and availability is not currently available.

Quality Level

assay

99%

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.469 (lit.)

bp

213-214 °C (lit.)

density

1.35 g/mL at 25 °C (lit.)

storage temp.

−20°C

SMILES string

CO[C@@](C(Cl)=O)(c1ccccc1)C(F)(F)F

InChI

1S/C10H8ClF3O2/c1-16-9(8(11)15,10(12,13)14)7-5-3-2-4-6-7/h2-6H,1H3/t9-/m1/s1

InChI key

PAORVUMOXXAMPL-SECBINFHSA-N

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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.

Packaging

50, 250 mg in glass bottle
Bottomless glass bottle. Contents are inside inserted fused cone.

Application

Used in the synthesis of natural products and pheromones.

Other Notes

doi:10.1038/nprot.2007.354

Pictograms

Corrosion

Signal Word

Danger

Hazard Statements

Precautionary Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 3265 8 / PGII

WGK Germany

WGK 3

Flash Point(F)

192.2 °F - closed cup

Flash Point(C)

89 °C - closed cup

José Luis García Ruano et al.
Organic letters, 6(11), 1757-1760 (2004-05-21)
A new type of vinylogous tin-Pummerer rearrangement reaction was observed when benzyl tin derivatives containing a sulfinyl group at the ortho position were allowed to react with acyl chlorides or TFAA. The reaction is thought to proceed by nucleophilic attack...
Seyed H Goldansaz et al.
Journal of chemical ecology, 30(4), 819-834 (2004-07-21)
Females of the potato aphid Macrosiphum euphorbiae exhibit typical calling behavior, with virgin female oviparae raising their back legs off the substrate to release sex pheromone from glands on the tibia. Airborne collections from calling oviparae were analyzed by GC...
Synthesis of beta-hydroxyaldehydes with stereogenic quaternary carbon centers by direct organocatalytic asymmetric aldol reactions.
Nobuyuki Mase et al.
Angewandte Chemie (International ed. in English), 43(18), 2420-2423 (2004-04-29)
Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons.
Hoye TR, et al.
Nature Protocols, 2(10), 2451-2458 (2007)
K J Miller et al.
Journal of chromatography, 307(2), 335-342 (1984-05-11)
High-performance liquid chromatography (HPLC) was employed for resolution of enantiomers of chiral ring-substituted 1-phenyl-2- aminopropanes (amphetamines) and 1-phenylethylamine following derivatization with four chiral reagents: (R)-(+)-1-phenylethyl isocyanate ( PEIC ), (-)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride ( MTPA X Cl), 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl isothiocyanate ( GITC )...

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