697761

Sigma-Aldrich

(R,R)-DIPAMP

95%

Synonym(s):
(R,R)-Ethylenebis[(2-methoxyphenyl)phenylphosphine], (R,R)-1,2-Bis[(2-methoxyphenyl)(phenylphosphino)]ethane, (R,R)-1,2-Ethanediylbis[(2-methoxyphenyl)phenylphosphine], [(1R,2R)-(−)-Bis[(2-methoxyphenyl)phenylphosphino]ethane]
Linear Formula:
[CH3OC6H4P(C6H5)CH2-]2
CAS Number:
Molecular Weight:
458.47
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

assay

95%

optical activity

[α]22/D −81°, c = 1 in chloroform

mp

102-106 °C (lit.)

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.

Packaging

100, 500 mg in amber glass bottle

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Target Organs

Respiratory system

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
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)
Development of an Asymmetric Hydrogenation Route to (S)-N-Boc-2, 6-Dimethyltyrosine
Praquin C, et al.
Organic Process Research & Development, 15(5), 1124-1129 (2011)
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)
Highly enantio-, regio-and diastereo-selective one-pot [2+ 3]-cycloaddition reaction via isomerization of 3-butynoates to allenoates
Sampath M and Loh T
Chemical Science, 1(6), 739-742 (2010)

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