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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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50 MG
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250 MG
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About This Item

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

$72.30

Available to ship onApril 29, 2025Details

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Quality Level

200

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.)

functional group

acyl chloride
ether
fluoro
phenyl

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.[1]

Application

Used in the synthesis of natural products[2][3] and pheromones.[4]

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_germany

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
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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Questions

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  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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