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369675

Sigma-Aldrich

(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
Beilstein:
3591562
MDL number:
MFCD00067105
UNSPSC Code:
12352101
PubChem Substance ID:
24863007
NACRES:
NA.22

Assay

99%

form

liquid

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.

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

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

192.2 °F - closed cup

Flash Point(C)

89 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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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