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748196

Sigma-Aldrich

(1R,2R)-2-Amino-1-phenylpropyldiphenylphosphine

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About This Item

Empirical Formula (Hill Notation):
C21H22NP
CAS Number:
799297-44-2
Molecular Weight:
319.38
MDL number:
MFCD17018768
UNSPSC Code:
12352116
PubChem Substance ID:
329765875
NACRES:
NA.22

form

solid

optical activity

[α]/D -138.0°, c = 0.5% in chloroform

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction
reaction type: Heck Reaction
reaction type: Hiyama Coupling
reaction type: Negishi Coupling
reaction type: Sonogashira Coupling
reaction type: Stille Coupling
reaction type: Suzuki-Miyaura Coupling
reagent type: ligand

mp

105-109 °C

functional group

phosphine

storage temp.

20-25°C

SMILES string

C[C@@H](N)[C@H](P(c1ccccc1)c2ccccc2)c3ccccc3

InChI

1S/C21H22NP/c1-17(22)21(18-11-5-2-6-12-18)23(19-13-7-3-8-14-19)20-15-9-4-10-16-20/h2-17,21H,22H2,1H3/t17-,21+/m1/s1

InChI key

JWZAIGGNEGTDMG-UTKZUKDTSA-N

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Lot/Batch Number
MKBK2424V

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A Saitoh et al.
The Journal of organic chemistry, 65(14), 4227-4240 (2000-07-13)
A new class of chiral amidine-phosphine hybrid ligands 7a,b, which are readily accessible from the corresponding alpha-amino acids, were developed. A versatility for construction of new ligands is desirable, by which a variety of reactions and substrates become applicable. Indeed
Chemoselective hydrogenation of imides catalyzed by Cp*Ru(PN) complexes and its application to the asymmetric synthesis of paroxetine.
Masato Ito et al.
Journal of the American Chemical Society, 129(2), 290-291 (2007-01-11)
T. Hayashi, M. Konishi et al.
The Journal of Organic Chemistry, 48, 2195-2195 (1983)
D. Amoroso, T.W. Graham et al.
Aldrichimica Acta, 41, 1-1 (2008)
Isaac J Krauss et al.
Organic letters, 5(18), 3201-3203 (2003-08-29)
[reaction: see text] A new ligand for Cu-catalyzed enantioselective additions of dialkylzincs to cyclic enones has been developed. In addition to providing good to excellent enantioselectivities with a range of cyclic enones and dialkylzincs, the ligand has several notworthy features:
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