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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

Assay

95%

form

solid

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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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