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230235

Diphenylphosphinic chloride

98%, liquid

Synonym(s):

Diphenylchlorophosphine oxide, Diphenylphosphinic acid chloride, Diphenylphosphinoyl chloride, Diphenylphosphinyl chloride, Diphenylphosphorus oxychloride, Ph2POCl, Chlorodiphenylphosphine oxide

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About This Item

Linear Formula:
(C6H5)2P(O)Cl
CAS Number:
Molecular Weight:
236.63
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352002
EC Number:
216-107-2
MDL number:
Beilstein/REAXYS Number:
975191

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Product Name

Diphenylphosphinic chloride, 98%

InChI key

QPQGTZMAQRXCJW-UHFFFAOYSA-N

InChI

1S/C12H10ClOP/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H

SMILES string

ClP(=O)(c1ccccc1)c2ccccc2

assay

98%

form

liquid

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling

refractive index

n20/D 1.609 (lit.)

bp

222 °C/16 mmHg (lit.)

density

1.24 g/mL at 25 °C (lit.)

storage temp.

2-8°C

Quality Level

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assay

98%

assay

96%

assay

90%

assay

99%

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Hiyama Coupling, reaction type: Sonogashira Coupling, reaction type: Suzuki-Miyaura Coupling, reaction type: Heck Reaction, reaction type: Stille Coupling, reaction type: Negishi Coupling

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Cross Couplings, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand

reaction suitability

reaction type: Buchwald-Hartwig Cross Coupling Reaction, reaction type: Heck Reaction, reaction type: Hiyama Coupling, reaction type: Negishi Coupling, reaction type: Sonogashira Coupling, reaction type: Stille Coupling, reaction type: Suzuki-Miyaura Coupling, reagent type: ligand

form

liquid

form

liquid

form

liquid

form

liquid

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

-

bp

222 °C/16 mmHg (lit.)

bp

320 °C (lit.)

bp

258 °C (lit.)

bp

320 °C (lit.)

Application

Diphenylphosphinic chloride (Ph2POCl) is widely used as a precursor to synthesize various chiral phosphine bidentate ligands[1][2][3][4][5] for asymmetric synthesis, in addition to several peptide coupling agents.[6][7][8]

signalword

Danger

Hazard Classifications

Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - Skin Sens. 1A

Storage Class

3 - Flammable liquids

wgk

WGK 3

flash_point_f

78.8 °F - closed cup

flash_point_c

26 °C - closed cup

ppe

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter


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Meifang Wang
Inorganic Chemistry, 33, 6, 1184-1187 (1994)
Difluorphos, an Electron?Poor Diphosphane: A Good Match Between Electronic and Steric Features.
Jeulin S, et al.
Angewandte Chemie (Weinheim an der Bergstrasse, Germany), 116(3), 324-329 (2004)
Efficient syntheses of korupensamines A, B and michellamine B by asymmetric Suzuki-Miyaura coupling reactions.
Xu G, et al.
Journal of the American Chemical Society, 136(2), 570-573 (2013)
Organophosphorus and nitro-substituted sulfonate esters of 1-hydroxy-7-azabenzotriazole as highly efficient fast-acting peptide coupling reagents.
Carpino L A, et al.
The Journal of Organic Chemistry, 69(1), 62-71 (2004)
Aboujaoude, E. E.; Lietje, S. et al.
Tetrahedron Letters, 26, 4435-4435 (1985)

Related Content

Phosphine Ligand Application Guide

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    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
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      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/418/501/product-dating-information-06-25-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer
    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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