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431737

Sigma-Aldrich

(R)-(+)-N-Benzyl-α-methylbenzylamine

98%

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Synonym(s):
(R)-(+)-N-(1-Phenylethyl)benzylamine, (R)-(+)-N-Benzyl-1-phenylethylamine
Linear Formula:
C6H5CH(CH3)NHCH2C6H5
CAS Number:
38235-77-7
Molecular Weight:
211.30
Beilstein:
3589990
MDL number:
MFCD00015010
UNSPSC Code:
12352116
PubChem Substance ID:
24867044

Assay

98%

optical activity

[α]20/D +38°, neat

optical purity

ee: ≥97% (HPLC)

refractive index

n20/D 1.564 (lit.)

bp

171 °C/15 mmHg (lit.)

density

1.01 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](NCc1ccccc1)c2ccccc2

InChI

1S/C15H17N/c1-13(15-10-6-3-7-11-15)16-12-14-8-4-2-5-9-14/h2-11,13,16H,12H2,1H3/t13-/m1/s1

InChI key

ZYZHMSJNPCYUTB-CYBMUJFWSA-N

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Application

(R)-(+)-N-Benzyl-α-methylbenzylamine may be used to prepare:
  • tert-Butyl (3S)-3-{benzyl[(1R)-1-phenylethyl]amino}-3-(6-methoxypyridin-3-yl)propanoate, an intermediate for the synthesis of the Merck & Co. Inc., Kenilworth, NJ, U.S. αvβ3 integrin antagonist.
  • A conformationally restricted piperidine-based analog of deoxynegamycin.
  • 5- and 6-[2,3]-dihydrobenzofuran β-amino acids, which can act as aspartic acid mimetics.
Chiral amine used for enantioselective deprotonations.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H315,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Certificates of Analysis (COA)

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An Efficient Synthesis of an av?3 Antagonist.
Yasuda N, et al.
The Journal of Organic Chemistry, 69(6), 1959-1966 (2004)
Syntheses of 5-and 6-[2,3]-dihydrobenzofuran ?-amino acids.
Coleman PJ, et al.
Tetrahedron Letters, 41(31), 5803-5806 (2000)
Price, D. Simpkins, N.S.
Tetrahedron Letters, 36, 6135-6135 (1995)
Bunn, B.J. Simpkins, N.S.
The Journal of Organic Chemistry, 58, 533-533 (1993)
Conformationally restricted analogs of deoxynegamycin.
Raju B, et al.
Bioorganic & Medicinal Chemistry Letters, 14(12), 3103-3107 (2004)
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