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726842

Sigma-Aldrich

(R)-(+)-4-Methoxy-α-methylbenzylamine

ChiPros®, produced by BASF, 99%

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Synonym(s):
(R)-(+)-1-(4-Methoxyphenyl)ethylamine
Empirical Formula (Hill Notation):
C9H13NO
CAS Number:
22038-86-4
Molecular Weight:
151.21
Beilstein:
2413029
MDL number:
MFCD00671659
UNSPSC Code:
12352112
PubChem Substance ID:
329764270
NACRES:
NA.22

grade

produced by BASF

Quality Level

100

Assay

≥98.5% (GC)
99%

form

liquid

optical purity

enantiomeric excess: ≥98.5%

density

1.024 g/mL at 20 °C (lit.)

SMILES string

COc1ccc(cc1)[C@@H](C)N

InChI

1S/C9H13NO/c1-7(10)8-3-5-9(11-2)6-4-8/h3-7H,10H2,1-2H3/t7-/m1/s1

InChI key

JTDGKQNNPKXKII-SSDOTTSWSA-N

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Application

(R)-(+)-4-Methoxy-α-methylbenzylamine can be used as a reactant to prepare:
  • Enantiopure stereoisomers of hemicryptophanes, which are used for the recognition of glucopyranosides.
  • Bicyclic Geissman-Waiss lactone via intramolecular ring-closure reaction of the diastereomeric mixture of sulfonium salts.
  • N-[(1R)-1-(4-Methoxyphenyl)ethyl]-N′-methylthiourea by reacting with methyl isothiocyanate.

Legal Information

ChiPros is a registered trademark of BASF SE

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H317,H412

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1A

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Improved hemicryptophane hosts for the stereoselective recognition of glucopyranosides
Schmitt A, et al.
Organic & Biomolecular Chemistry, 12(24), 4211-4217 (2014)
Synthesis of (+)-and (-)-Geissman-Waiss lactone from chiral sulfonium salts
Lopez-Gonzalez R, et al.
Tetrahedron Letters, 12(24), 151697-151697 (2020)
Yohan Park et al.
Archives of pharmacal research, 35(8), 1393-1401 (2012-09-04)
Thirty two thiourea derivatives were prepared and their agonistic activities on the retinoic acid receptor-related orphan receptor α (RORα) were evaluated. The replacement of the 3-allyl-2-imino-thiazolidin-4-one moiety of the lead compound CGP52608 (1) with various functional group substituted aromatic rings

Articles

ChiPros Chiral Amines

Chiral amines play an important role in stereoselective organic synthesis. They are used directly as resolving agents, building blocks, or chiral auxiliaries.

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