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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
Pricing and availability is not currently available.

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.[1]
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.[2]
  • As a reactant in the synthesis of perfluoroalkyl(phenyl)phosphinic acids from perfluoroalkyl Grignard reagents.[3]
  • As a starting material for the synthesis of benzoxazine monomer containing phenylphosphine oxide which can be polymerized via ring-opening polymerization.[4]
  • As a chlorinating agent for the conversion of thienopyrimidinedione into 4,6-dichlorothienopyrimidine.[5]

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

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

399.2 °F

Flash Point(C)

204 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT8080
MKCS3553
MKCQ2437
MKCM6960
SHBK9270

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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)
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)

Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    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.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-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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