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452823

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

Name: (+)-Bis[(<I>R</I>)-1-phenylethyl]amine
Brand: ALDRICH

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

UNSPSC Code:

12352116

NACRES:

NA.22

PubChem Substance ID:

24868728

MDL number:

MFCD00243088

Beilstein/REAXYS Number:

3590931

Assay:

99%

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Properties

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.)

functional group

amine, phenyl

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

flash_point_f

>235.4 °F - closed cup

flash_point_c

> 113 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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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)

Diels-Alder reactions of cyclic isoimidium salts.

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.

Optimisation of a lithium magnesiate for use in the non-cryogenic asymmetric deprotonation of prochiral ketones.

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

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Global Trade Item Number

SKU	GTIN
452823-10G	04061837394683
452823-1G	04061837394690