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389560

Sigma-Aldrich

Phenylphosphonic dichloride

technical grade, 90%

Synonym(s):

Benzenephosphonic dichloride, Benzenephosphonyl chloride, Phenyldichlorophosphine oxide, Phenylphosphonyl dichloride, Phenylphosphoryl dichloride, P,P-Dichlorophenylphosphine oxide

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About This Item

Linear Formula:
C6H5POCl2
CAS Number:
824-72-6
Molecular Weight:
194.98
Beilstein:
1072240
EC Number:
212-534-3
MDL number:
MFCD00002070
UNSPSC Code:
12352106
PubChem Substance ID:
24864291
NACRES:
NA.22

grade

technical grade

Quality Level

100

Assay

90%

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 1.559 (lit.)

bp

258 °C (lit.)

mp

3 °C (lit.)

density

1.375 g/mL at 25 °C (lit.)

SMILES string

ClP(Cl)(=O)c1ccccc1

InChI

1S/C6H5Cl2OP/c7-10(8,9)6-4-2-1-3-5-6/h1-5H

InChI key

IBDMRHDXAQZJAP-UHFFFAOYSA-N

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Application

Phenylphosphonic dichloride (PPDC) is an organophosphorus compound with flame-retardant properties.
It can be used:
  • In the synthesis of PBPP (3,9-diphenyl-3,9-dioxa-2,4,8,10-tetraoxa-3,9-diphosphaspiro-5,5-undecane), another organo-phosphorus flame retardant.
  • As a reactant in the synthesis of perfluoroalkyl(phenyl)phosphinic acids from perfluoroalkyl Grignard reagents.
  • As a starting material for the synthesis of benzoxazine monomer containing phenylphosphine oxide which can be polymerized via ring-opening polymerization.
  • As a chlorinating agent for the conversion of thienopyrimidinedione into 4,6-dichlorothienopyrimidine.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H314,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Supplementary Hazards

EUH014

WGK

WGK 3

Flash Point(F)

399.2 °F

Flash Point(C)

204 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

危险化学品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Thermal degradation properties of wood reacted with diethylchlorophosphate or phenylphosphonic dichloride as potential flame retardants
Ellis WD, et al.
Wood and Fiber Science, 19(4), 439-445 (2007)
A study of the reaction of perfluoroalkyl Grignard reagents with phosphoryl chloride and phenylphosphonic dichloride
Hosein AI and Caffyn AJM
Dalton Transactions, 41(43), 13504-13508 (2012)
Synthesis and applications of biscyclic phosphorus flame retardants
Hoang D and Kim J
Polymer Degradation and Stability, 93(1), 36-42 (2008)
Thienopyrimidine-based P2Y12 platelet aggregation inhibitors
Kortum SW, et al.
Bioorganic & medicinal chemistry letters, 19(20), 5919-5923 (2009)
Synthesis, characterization and thermal degradation of functional benzoxazine monomers and polymers containing phenylphosphine oxide.
Choi S-W, et al.
Polymer Degradation and Stability, 91(5), 1166-1178 (2006)

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