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Sigma-Aldrich

Diphenylphosphinic chloride

98%

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:
1499-21-4
Molecular Weight:
236.63
Beilstein:
975191
EC Number:
216-107-2
MDL number:
MFCD00002077
UNSPSC Code:
12352002
PubChem Substance ID:
24853787
NACRES:
NA.22

Quality Level

100

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

SMILES string

ClP(=O)(c1ccccc1)c2ccccc2

InChI

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

InChI key

QPQGTZMAQRXCJW-UHFFFAOYSA-N

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Application

Diphenylphosphinic chloride (Ph2POCl) is widely used as a precursor to synthesize various chiral phosphine bidentate ligands for asymmetric synthesis, in addition to several peptide coupling agents.

Signal Word

Danger

Hazard Statements

H226,H314,H317

Hazard Classifications

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

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

78.8 °F - closed cup

Flash Point(C)

26 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
STBL4192
SDBB0853
STBK9309
STBK3049
STBJ9694

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Aboujaoude, E. E.; Lietje, S. et al.
Tetrahedron Letters, 26, 4435-4435 (1985)
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)
The development of highly efficient onium?type peptide coupling reagents based upon rational molecular design.
Li P and Xu JC
The Journal of Peptide Research, 58(2), 129-139 (2001)
Indium?Mediated Asymmetric Allylation of Acylhydrazones Using a Chiral Urea Catalyst.
Tan K L and Jacobsen E N
Angewandte Chemie (International Edition in English), 46(8), 1315-1317 (2007)
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)
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