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D71984

Sigma-Aldrich

P,P-Dichlorophenylphosphine

97%

Synonym(s):

Phenyldichlorophosphine, Phenylphosphine dichloride, PhPCl2, Phenylphosphonous dichloride

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About This Item

Linear Formula:
C6H5PCl2
CAS Number:
644-97-3
Molecular Weight:
178.98
Beilstein:
508189
EC Number:
211-425-8
MDL number:
MFCD00000528
UNSPSC Code:
12352002
PubChem Substance ID:
24894089
NACRES:
NA.22

Quality Level

100

Assay

97%

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
reagent type: ligand

refractive index

n20/D 1.597 (lit.)

bp

222 °C/759 mmHg (lit.)

mp

−51 °C (lit.)

density

1.319 g/mL at 25 °C (lit.)

functional group

phosphine

SMILES string

ClP(Cl)c1ccccc1

InChI

1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H

InChI key

IMDXZWRLUZPMDH-UHFFFAOYSA-N

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General description

P,P-Dichlorophenylphosphine (DCPP) is a key compound in organic synthesis. It is widely used to prepare flame retardants, nylon stabilizers, plasticizers, and organophosphorus compounds. It can be prepared by the Friedel-Craft reaction between phosphorus trichloride and benzene in the presence of anhydrous aluminum chloride as a catalyst.

Application

P,P-Dichlorophenylphosphine is used as a reactant to synthesize racemic [1]ferrocenophanes (mixture of cis and trans isomers)

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H314,H335

Hazard Classifications

Acute Tox. 3 Oral - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

WGK

WGK 3

Flash Point(F)

closed cup

Flash Point(C)

closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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Insight into the Thermal Ring-Opening Polymerization of Phospha [1] ferrocenophanes
Khozeimeh S, et al.
Chemistry?A European Journal , 22(47), 16838-16849 (2016)
Jan Hynek et al.
Organic & biomolecular chemistry, 16(39), 7274-7281 (2018-09-28)
The development of effective photosensitizers is particularly attractive for photodynamic therapy of cancer. Three novel porphyrin photosensitizers functionalized with phosphinic groups were synthesized and their physicochemical, photophysical, and photobiological properties were collected. Phosphinic acid groups (R1R2POOH) attached to the porphyrin
Paul A Gray et al.
Dalton transactions (Cambridge, England : 2003), 45(5), 2124-2129 (2015-10-23)
A series of 2-phosphino-1,3-diphosphonium trifluoromethanesulfonate salts has been prepared and comprehensively characterized. The compounds represent rare examples of salts containing triphosphorus dications and establish important structural and spectroscopic parameters and trends for catenated phosphorus chains.
Preparation of dichlorophenylphosphine via Friedel--Crafts reaction in ionic liquids
Wang ZW,et al.
Green Chemistry, 5(6), 737-739 (2003)
G Bas de Jong et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 26(68), 15944-15952 (2020-07-01)
In this paper, we highlight the synthesis of a variety of primary phosphine-boranes (RPH2 ⋅BH3 ) from the corresponding dichlorophosphines, simply by using Li[BH4 ] as reductant and provider of the BH3 protecting group. The method offers facile access not

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