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697761

(R,R)-DIPAMP

Name: (<I>R,R</I>)-DIPAMP
Brand: ALDRICH

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

NACRES:

NA.22

PubChem Substance ID:

329761951

UNSPSC Code:

12352112

MDL number:

MFCD05863546

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Properties

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

Description

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

GHS07

signalword

Warning

hcodes

H315,H319,H335,H413

pcodes

P273 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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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)

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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Global Trade Item Number

SKU	GTIN
697761-100MG	04061832625430
697761-500MG	04061832625447