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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

signalword

Danger

hcodes

H314

Hazard Classifications

Skin Corr. 1B

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKBK2424V

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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:
Masato Ito et al.
Angewandte Chemie (International ed. in English), 48(7), 1324-1327 (2009-01-09)
Awakening of the Cp one: The bifunctional complex 1 facilitates the interaction with substrates bearing less electrophilic carbon atoms than ketones, epoxides, and imides. The title reaction was applicable to the reduction of Evans' asymmetric alkylation products to the chiral
T. Hayashi, M. Konishi et al.
The Journal of Organic Chemistry, 48, 2195-2195 (1983)
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)
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