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287644

Sigma-Aldrich

(1R,2R)-(−)-Pseudoephedrine

98%

Synonym(s):

α-(1-Methylaminoethyl)benzyl alcohol, (−)-ψ-Ephedrine, (−)-Pseudoephedrine, (1R,2R)-(−)-2-(Methylamino)-1-phenylpropanol, l-Pseudoephedrine

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About This Item

Linear Formula:
C6H5CH[CH(NHCH3)CH3]OH
CAS Number:
321-97-1
Molecular Weight:
165.23
Beilstein:
2803417
EC Number:
206-292-8
MDL number:
MFCD00002203
UNSPSC Code:
12352116
PubChem Substance ID:
24857283
NACRES:
NA.22

Assay

98%

form

solid

optical activity

[α]20/D −51°, c = 0.6 in ethanol

mp

118-120 °C (lit.)

functional group

amine
hydroxyl
phenyl

SMILES string

CN[C@H](C)[C@H](O)c1ccccc1

InChI

1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m1/s1

InChI key

KWGRBVOPPLSCSI-SCZZXKLOSA-N

General description

(1R,2R)-(-)-Pseudoephedrine is an enantiomer of ephedrine mainly used as a chiral auxiliary for asymmetric synthesis.

Application

(1R,2R)-(-)-Pseudoephedrine may be used in the preparation of chiral relay ligands, which can catalyze the addition of diethylzinc to aldehydes leading to the corresponding secondary alcohol. The immobilization of pseudoephedrine on Merrifield resin forms a chiral linker, which may be used for the asymmetric alkylation of amides via solid-phase approach.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317,H336

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0001451678
1451678V
1451678
1342934
1331220

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Evaluation of a pseudoephedrine linker for asymmetric alkylations on solid phase.
Hutchison PC, et al.
Organic Letters, 4(26), 4583-4585 (2002)
Pseudoephedrine as a practical chiral auxiliary for the synthesis of highly enantiomerically enriched carboxylic acids, alcohols, aldehydes, and ketones.
Myers AG, et al.
Journal of the American Chemical Society, 119(28), 6496-6511 (1997)
Enantioselective diethylzinc additions to aldehydes catalyzed by chiral relay ligands.
Sibi MP and Levi M. Stanley.
Tetrahedron Asymmetry, 15(21), 3353-3356 (2004)

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