Key Documents

(R,R)-DIPAMP

Name: (<I>R,R</I>)-DIPAMP
Brand: ALDRICH
Price: 190 USD

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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Pack Size	SKU	Availability	Price
100 mg		0 left in stock	$190.00
500 mg		1 left in stock	$673.00

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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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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Catalysts

Chiral Catalysts & Ligands

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1 of 1

This Item	697753	295817	693065
Sigma-Aldrich 697761 (R,R)-DIPAMP	Sigma-Aldrich 697753 (S,S)-DIPAMP	Sigma-Aldrich 295817 (R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene	Sigma-Aldrich 693065 (R)-BINAP
assay 95%	assay 95%	assay 97%	assay -
form solid	form solid	form solid	form crystals
functional group phosphine	functional group phosphine	functional group phosphine	functional group phosphine
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
mp 102-106 °C (lit.)	mp 101-105 °C (lit.)	mp 239-241 °C (lit.)	mp 239-241 °C (lit.)
optical activity [α]22/D −81°, c = 1 in chloroform	optical activity [α]22/D +82, c = 1 in chloroform	optical activity [α]19/D +233°, c = 0.3 in toluene	optical activity [α]20/D +222°, c = 0.5% in benzene

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

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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)

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)

Global Trade Item Number

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

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