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Merck
CN

389560

Phenylphosphonic dichloride

90%, technical grade, liquid

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
NACRES:
NA.22
PubChem Substance ID:
24864291
UNSPSC Code:
12352106
EC Number:
212-534-3
MDL number:
MFCD00002070
Beilstein/REAXYS Number:
1072240

Key Documents

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Product Name

Phenylphosphonic dichloride, technical grade, 90%

InChI key

IBDMRHDXAQZJAP-UHFFFAOYSA-N

InChI

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

SMILES string

ClP(Cl)(=O)c1ccccc1

grade

technical grade

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

Quality Level

100

bp

258 °C (lit.)

mp

3 °C (lit.)

density

1.375 g/mL at 25 °C (lit.)

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

signalword

Danger

Hazard Classifications

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

target_organs

Respiratory system

supp_hazards

EUH014

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

flash_point_f

399.2 °F

flash_point_c

204 °C

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKDB2197
MKCX5907
MKCT8080
MKCS3553
MKCQ2437

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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)
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)
Thienopyrimidine-based P2Y12 platelet aggregation inhibitors
Kortum SW, et al.
Bioorganic & medicinal chemistry letters, 19(20), 5919-5923 (2009)
Synthesis and applications of biscyclic phosphorus flame retardants
Hoang D and Kim J
Polymer Degradation and Stability, 93(1), 36-42 (2008)
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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