Skip to Content
Merck
All Photos(1)

Documents

452823

Sigma-Aldrich

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

99%

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(1)

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

Quality Level

100

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Scalable Route to Chiral Phosphoramidites
Krasutsky SG and Jacobo SH
International Journal of Chemistry (Canadian Center of Science and Education), 8(2) (2016)
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)
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.
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service