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401358

Sigma-Aldrich

(S)-(−)-N,α-Dimethylbenzylamine

98%

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Synonym(s):
(S)-DMBA, (S)-(−)-N-Methyl-1-phenylethylamine
Linear Formula:
C6H5CH(CH3)NHCH3
CAS Number:
19131-99-8
Molecular Weight:
135.21
Beilstein:
1446867
MDL number:
MFCD00067113
UNSPSC Code:
12352116
PubChem Substance ID:
24865006
NACRES:
NA.22

Assay

98%

form

liquid

optical activity

[α]20/D −73±5°, c = 2 in chloroform

refractive index

n20/D 1.512 (lit.)

bp

74-76 °C/11 mmHg (lit.)

density

0.928 g/mL at 20 °C (lit.)

SMILES string

CN[C@@H](C)c1ccccc1

InChI

1S/C9H13N/c1-8(10-2)9-6-4-3-5-7-9/h3-8,10H,1-2H3/t8-/m0/s1

InChI key

RCSSHZGQHHEHPZ-QMMMGPOBSA-N

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General description

(S)-(-)-N,a-Dimethylbenzylamine may be used along with benzaldehyde in the Mannich-type aminoalkylation of 2-naphthol to form 1-((S)-phenyl(((1′S)-1′-phenylethyl)methylamino)methyl)-2-naphthol. This optically active tertiary aminonaphthol can catalyze the enantioselective alkenylation of various aldehyde to generate chiral (E)- allyl alcohols.

Application

Used to make asymmetric organometallic catalysts (e.g., for conjugate additions to enones).

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302 + H312 + H332,H314

Hazard Classifications

Acute Tox. 4 Oral - Skin Corr. 1B

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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A convenient, one-step synthesis of optically active tertiary aminonaphthol and its applications in the highly enantioselective alkenylations of aldehydes
J JX, et al.
The Journal of Organic Chemistry, 68(4), 1589-1590 (2003)
Tetrahedron Letters, 31, 965-965 (1990)

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