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Merck
CN

369675

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

99%

Synonym(s):

(S)-(+)-MTPA-Cl, Mosher’s acid chloride

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About This Item

Linear Formula:
C6H5C(OCH3)(CF3)COCl
CAS Number:
20445-33-4
Molecular Weight:
252.62
UNSPSC Code:
12352101
NACRES:
NA.22
PubChem Substance ID:
24863007
MDL number:
MFCD00067105
Beilstein/REAXYS Number:
3591562
Assay:
99%
Form:
liquid

Key Documents

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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

SMILES string

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

InChI key

PAORVUMOXXAMPL-SECBINFHSA-N

assay

99%

form

liquid

optical purity

ee: 98% (GLC)

Quality Level

200

bp

213-214 °C (lit.)

density

1.35 g/mL at 25 °C (lit.)

functional group

acyl chloride, ether, fluoro, phenyl

storage temp.

−20°C

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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.

Application

Used in the synthesis of natural products and pheromones.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

doi:10.1038/nprot.2007.354

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

192.2 °F - closed cup

flash_point_c

89 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCL7047
BCCG0230
BCBZ2911
BCBN8548V
BCBC2856V

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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
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)
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
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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