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697761

Sigma-Aldrich

(R,R)-DIPAMP

95%

Synonym(s):

(R,R)-1,2-Bis[(2-methoxyphenyl)(phenylphosphino)]ethane, (R,R)-1,2-Ethanediylbis[(2-methoxyphenyl)phenylphosphine], (R,R)-Ethylenebis[(2-methoxyphenyl)phenylphosphine], [(1R,2R)-(−)-Bis[(2-methoxyphenyl)phenylphosphino]ethane]

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About This Item

Linear Formula:
[CH3OC6H4P(C6H5)CH2-]2
CAS Number:
55739-58-7
Molecular Weight:
458.47
MDL number:
MFCD05863546
UNSPSC Code:
12352112
PubChem Substance ID:
329761951
NACRES:
NA.22

Quality Level

100

Assay

95%

form

solid

optical activity

[α]22/D −81°, c = 1 in chloroform

mp

102-106 °C (lit.)

functional group

phosphine

SMILES string

COc1ccccc1P(CCP(c2ccccc2)c3ccccc3OC)c4ccccc4

InChI

1S/C28H28O2P2/c1-29-25-17-9-11-19-27(25)31(23-13-5-3-6-14-23)21-22-32(24-15-7-4-8-16-24)28-20-12-10-18-26(28)30-2/h3-20H,21-22H2,1-2H3/t31-,32-/m1/s1

InChI key

QKZWXPLBVCKXNQ-ROJLCIKYSA-N

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Application

(R, R)-DIPAMP can be used:
  • As a catalyst in the enantioselective [3+2] cycloaddition of γ-substituted allenoates with β-perfluoroalkyl enones and 3-butynoates with electron-deficient olefins to yield substituted cyclopentenes.
  • To prepare its rhodium metal complexes, which are used as catalysts in asymmetric hydrogenation reactions.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335,H413

Hazard Classifications

Aquatic Chronic 4 - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCK1758
MKBN8626V
09314EJ
07327BJ

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Effect of gas-liquid mass transfer on enantioselectivity in asymmetric hydrogenations
Pestre N, et al.
J. Mol. Catal. A: Chem., 252(1-2), 85-89 (2006)
Phosphine-catalyzed enantioselective [3+2] cycloadditions of γ-substituted allenoates with β-perfluoroalkyl enones
Zhou W, et al.
Chemical Science, 8(6), 4660-4665 (2017)

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