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344109

Sigma-Aldrich

(R)-(−)-N,N-Dimethyl-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethylamine

95%

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About This Item

Empirical Formula (Hill Notation):
C26H28FeNP
CAS Number:
Molecular Weight:
441.33
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:

assay

95%

optical activity

[α]20/D −355°, c = 0.6 in ethanol

reaction suitability

reaction type: Asymmetric synthesis
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
reaction type: Cross Couplings

mp

141-143 °C (lit.)

functional group

phosphine

SMILES string

[Fe].[CH]1[CH][CH][CH][CH]1.C[C@H]([C]2[CH][CH][CH][C]2P(c3ccccc3)c4ccccc4)N(C)C

InChI

1S/C21H23NP.C5H5.Fe/c1-17(22(2)3)20-15-10-16-21(20)23(18-11-6-4-7-12-18)19-13-8-5-9-14-19;1-2-4-5-3-1;/h4-17H,1-3H3;1-5H;/t17-;;/m1../s1

InChI key

RCAFPSZHKFOLEE-ZEECNFPPSA-N

Application

Ligand used in the enantioselective vinylation of aldehydes.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Iio, H. et al.
Journal of the Chemical Society. Chemical Communications, 1390-1390 (1991)

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