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452823

Sigma-Aldrich

(+)-Bis[(R)-1-phenylethyl]amine

99%

Synonym(s):

(+)-Bis[(R)-α-methylbenzyl]amine, [R-(R*,R*)]-(+)-Bis(α-methylbenzyl)amine

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About This Item

Linear Formula:
[C6H5CH(CH3)]2NH
CAS Number:
23294-41-9
Molecular Weight:
225.33
Beilstein:
3590931
MDL number:
MFCD00243088
UNSPSC Code:
12352116
PubChem Substance ID:
24868728
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D +199.0°, neat

optical purity

ee: ≥99% (GLC)

refractive index

n20/D 1.5523 (lit.)

bp

86 °C/0.05 mmHg (lit.)

density

0.985 g/mL at 25 °C (lit.)

SMILES string

C[C@@H](N[C@H](C)c1ccccc1)c2ccccc2

InChI

1S/C16H19N/c1-13(15-9-5-3-6-10-15)17-14(2)16-11-7-4-8-12-16/h3-14,17H,1-2H3/t13-,14-/m1/s1

InChI key

NXLACVVNHYIYJN-ZIAGYGMSSA-N

Application

(+)-Bis[(R)-1-phenylethyl]amine can be used:
  • In the synthesis of β-amino acids.
  • In the preparation of chiral C(19)-C(26) and C(27)-C(32) moieties of scytophycin C.
  • To induce enantioselectivity in the deprotonation of prochiral ketones.
  • As a starting material for the synthesis of chiral phenolate ligands through Mannich condensation reaction.
  • In the synthesis of chiral phosphoramidite ligands.
  • To prepare chiral cyclic isoimidium salts, which are further used to synthesize chiral lactones through Diels-Alder reaction.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

>235.4 °F - closed cup

Flash Point(C)

> 113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis and Characterization of New Chiral Monoanionic [ON] Ancillary Phenolate Ligands
Binda P, et al.
International Journal of Organic Chemistry, 4(03), 182-182 (2014)
Javier Francos et al.
Dalton transactions (Cambridge, England : 2003), 43(3), 1408-1412 (2013-11-10)
A study has been conducted to determine whether lithium magnesiates are feasible candidates for the enantioselective deprotonation of 4-alkylcyclohexanones. The commercially available chiral amine (+)-bis[(R)-1-phenylethyl]amine (2-H) was utilised to induce enantioselection. When transformed to its lithium salt and combined with
Robert K Boeckman et al.
Organic letters, 12(20), 4524-4527 (2010-09-17)
Diels-Alder reactions of cyclic isoimidium salts are described. The corresponding cycloadducts are obtained with high regio- and stereoselectivity. The use of homochiral cyclic isoimidium salts delivers cycloadducts with excellent diastereoselectivity (>99:1) that can be efficiently converted to enantiomerically pure lactones.
Asymmetric synthesis of R-beta-amino butanoic acid and S-beta-tyrosine: Homochiral lithium amide equivalents for Michael additions to alpha, beta-unsaturated esters.
Davies SG and Ichihara O
Tetrahedron Asymmetry, 2(3), 183-186 (1991)
Davies, S.G. Ichihara, O.
Tetrahedron Asymmetry, 2, 183-183 (1991)
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