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65361

Supelco

(R)-(+)-α-Methoxy-α-trifluoromethylphenylacetic acid

for chiral derivatization, LiChropur, ≥99.0%

Synonym(s):

(+)-MTPA, Mosher’s acid

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About This Item

Linear Formula:
C6H5C(OCH3)(CF3)CO2H
CAS Number:
Molecular Weight:
234.17
Beilstein:
3591560
EC Number:
MDL number:
UNSPSC Code:
12000000
PubChem Substance ID:
NACRES:
NA.22

grade

for chiral derivatization

Quality Level

Assay

≥99.0% (T)
≥99.0%

form

solid

optical activity

[α]20/D +73±1°, c = 2% in methanol

optical purity

enantiomeric ratio: ≥99.5:0.5 (GC)

quality

LiChropur

technique(s)

HPLC: suitable

refractive index

n20/D 1.473 (lit.)

bp

105-107 °C/1 mmHg (lit.)

mp

46-49 °C (lit.)

density

1.344 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C10H9F3O3/c1-16-9(8(14)15,10(11,12)13)7-5-3-2-4-6-7/h2-6H,1H3,(H,14,15)/t9-/m1/s1

InChI key

JJYKJUXBWFATTE-SECBINFHSA-N

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General description

Mosher′s acid chloride is generally used as a chiral derivatizing agent. It is easily available in enantiomerically pure form. It can form diastereomers with both alcohols and amines.

Application

Mosher′s acid chloride is used as a dervatization agent for β-arylethylamines, enantiomeric alcohols, and enantiomeric amines. It is also a reagent used for the determination of enantiomeric purity and absolute configuration of alcohols and amines by NMR.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

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Legal Information

LiChropur is a trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Michael North
Principles and Applications of Stereochemistry, 112-112 (1998)
J Gal
Journal of pharmaceutical sciences, 66(2), 169-172 (1977-02-01)
Amphetamine and eight related compounds were reacted with the chiral acylating reagent (-)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetyl chloride to obtain, in each case, two diastereomeric amide derivatives. GLC conditions were found for the separation of the diastereomers in seven of the nine cases studied.
J.A. Dale et al.
The Journal of Organic Chemistry, 34, 2543-2543 (1969)
S. Yamagichi et al.
Asymmetric Synthesis, 1, 128-128 (1983)
N. Kalyanam et al.
Tetrahedron Letters, 415-415 (1979)

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