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Diphenyl chlorophosphate

HCID 75654
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
2524-64-3
Standard SMILES
O=P(Cl)(Oc1ccccc1)Oc1ccccc1
InChIKey
BHIIGRBMZRSDRI-UHFFFAOYSA-N
Molecular formula
C12H10ClO3P
Average molar mass
268.63 g/mol
Monoisotopic mass
268.00560849

Overview

Diphenyl chlorophosphate appears as a clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes.

Names & identifiers

Preferred name
Diphenyl chlorophosphate
IUPAC
[chloro(phenoxy)phosphoryl]oxybenzene
English name
Diphenyl chlorophosphate
Molecular formula
C12H10ClO3P
Molecular weight
268.63

Names & synonyms

Diphenyl chlorophosphate2524-64-3Diphenyl phosphorochloridatediphenyl chlorophosphonateDiphenylphosphoryl chlorideChlorodiphenoxyphosphine oxidePhosphorochloridic acid, diphenyl esterDiphenoxychlorophosphine oxideO,O-Diphenyl chlorophosphateDiphenylphosphoric acid monochlorideDiphenyl phosphochloridatePhosphoric acid chloride diphenyl ester
Show more names
DPCPCHLOROPHOSPHORIC ACID DIPHENYL ESTERDPOCDiphenylchlorophosphonateDiphenyl chloridophosphateDCP:DPCP(PhO)2POCIAURORA KA-1636
DiphenylphosphorylchloridateDTXSID2044892Phenyl phosphorochloridate ((PhO)2ClPO)1KEE9757OTNSC-43771DIPHENYL PHOSPHOROCHLORATEDTXCID0024892PHENYL PHOSPHOROCHLORIDITE

Database identifiers

CAS
2524-64-3

Properties

Computed structural propertiesFilling in

XLogP
3.5
Topological polar surface area
35.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
17
Formal charge
0
Complexity
249

Experimental & physicochemical properties

Density1.296 @25 °C
Physical Description · 2 items

Diphenyl chlorophosphate appears as a clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes.

Liquid

Physicochemical properties

Boiling point
314 · 314-316 °C/272 mmHg (lit.)
Density
1.296 g/mL · 1.296 g/mL at 25 °C (lit.)
vapor pressure
10 mm · 10 mm Hg ( 190 °C)
refractive index
20 · n20/D 1.55(lit.)
Flash point
230 °F · >230 °F
storage temp.
2 · Inert atmosphere,2-8°C
solubility
Chloroform (Slightly), DMSO (Slightly)
form
Liquid
color
Clear colorless to light yellow

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (69.9%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P319, P321, P330, P363, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 166 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 4 items

Chemical: Phosphorochloridic acid, diphenyl ester

Phosphorochloridic acid, diphenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorochloridic acid, diphenyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 08-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19780

Diphenyl phosphorochloridate: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive
Fire HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters
Reactivity Profile · 1 item

Chemistry & industry

Uses & manufacturing

U.S. Production2023: 1,000,000 - <5,000,000 lb
Consumer UsesIntermediate
Industry UsesHydraulic fluids
General Manufacturing Information · 2 items

Utilities

Phosphorochloridic acid, diphenyl ester: ACTIVE

Applications · 5 items

DescriptionDiphenyl chlorophosphate is a viscous colorless liquid. It can be prepared in situ by the reaction between diphenyl hydrogen phosphonate and carbon tetrachloride. It is used to prepare aromatic polyesters by polycondensation reaction in pyridine and polyesteramide. Diphenyl chlorophosphate is used as a phosphonating agent, such as to prepare phenylphosphonic acid.

UsesDiphenyl chlorophosphate can be used to synthesize methadone, an opioid used for opioid maintenance therapy and for pain relief. It is used to control seedling grasses in turf. It undergoes anhydrous condensation with ethyl-4-bromo-butyrate and the hydrolysis product in alkaline medium of this condensation reaction is used in the quantitative determination of 3-cyano-3,3-diphenylpropionic acid.

UsesDiphenyl chlorophosphate is used to prepare cyclohexyl-amidophosphoric acid diphenyl ester by reacting with cyclohexylamine. It is also used in the synthesis of alfa-substituted beta-lactams, anhydrides, esters and thioesters. It is also employed in the conversion of aldoximes to nitriles. Further, it is used in the preparation and reaction of enol phosphates, guanosine-adenosine-5',5'-triphosphate, guanosine-cytidine-5',5'-triphosphate, guanosine-uridine-5',5'-triphosphate, diguanosine-5',5'-diphosphate and diguanosine-5',5'-triphosphate. In addition to this, it serves as a phosphorylating agent for the preparation of 2-deoxy-D-galactose-3 and -6 phosphoric acids.

UsesDiphenyl chlorophosphate may be used:in the preparation of guanosine-adenosine-5′,5′-triphosphate, guanosine-cytidine-5′,5′-triphosphate, guanosine-uridine-5′,5′-triphosphate, diguanosine-5′,5′-diphosphate and diguanosine-5′,5′-triphosphateas phosphorylating agent for the synthesis of 2-deoxy-D-galactose-3 and -6 phosphoric acidsin the synthesis of diaryl phosphoryl derivatives of alkylene dithiophosphates

Related reactions

507 records
New reaction record
HRID 3669 reaction equation
HRID 3669As reactantuspto-grants-1998_03
HRID 3670 reaction equation
HRID 3670As reactantuspto-grants-1998_03
HRID 11169 reaction equation
HRID 11169As reactantuspto-grants-2006_08
HRID 36497 reaction equation
HRID 36497As reactantuspto-grants-1995_05
HRID 43240 reaction equation
HRID 43240As reactantuspto-grants-2013_09
HRID 45283 reaction equation
HRID 45283As reactantuspto-grants-2013_09
HRID 70725 reaction equation
HRID 70725As reactantuspto-grants-2014_09
HRID 82424 reaction equation
HRID 82424As reactantuspto-grants-2014_09
Page 1 of 64

Compound notes

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PubChem CID
75654
DTXSID
DTXSID2044892
ChEMBL
CHEMBL3188224
UNII
1KEE9757OT
EC Number
219-759-6
Nikkaji
J7.599J
Water Solubility
MAY DECOMPOSE
Sensitive
Moisture Sensitive
BRN
654130 · 654130
Henry's Law Constant
3.7 · 3.7×10-2 mol/(m3Pa) at 25℃, Bartelt-Hunt et al. (2008)
Stability
Stable under recommended storage conditions., Stable Under Recommended Storage C
InChI
1S/C12H10ClO3P/c13-17(14,15-11-7-3-1-4-8-11)16-12-9-5-2-6-10-12/h1-10H
InChIKey
BHIIGRBMZRSDRI-UHFFFAOYSA-N
SMILES
ClP(=O)(Oc1ccccc1)Oc2ccccc2
CAS DataBase Reference
2524 · 2524-64-3(CAS DataBase Reference)
FDA UNII
1 KEE9757OT · 1KEE9757OT
NIST Chemistry Reference
Diphenyl chlorophosphate(2524-64-3)
EPA Substance Registry System
Phosphorochloridic acid, diphenyl ester (2524-64-3)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
5 · GHS05,GHS07
Signal word
Danger
Hazard statements
302 · H302-H314
Precautionary statements
270 · P270-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes
C
Risk Statements
34 · 34-37
Safety Statements
26 · 26-36/37/39-45-7-24/25-23
RIDADR
3265 · UN 3265 8/PG 2
WGK Germany
3 · 3
TSCA
TSCA listed
HazardClass
8 · 8
PackingGroup
III
HS Code
29209085 · 29209085
Storage Class
8 A · 8A - Combustible corrosive hazardous materials
Hazard Classifications
4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B
REACH Registrations
Active
Limited Quantities
1 L · 1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

DIPHENYL CHLOROPHOSPHATE is incompatible with bases (including amines) strong oxidizing agents, and alcohols. May react vigorously or explosively if mixed with diisopropyl ether or other ethers in the presence of trace amounts of metal salts [J. Haz. Mat., 1981, 4, 291]. May form highly toxic and flammable phosphine gas in the presence of strong reducing agents such as hydrides. Partial oxidation by oxidizing agents may result in the release of toxic phosphorus oxides.

Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesAcute Tox. 4 (69.9%)

Safety & protection

Fire FightingExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
First AidExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 items

7.9 [mg/m3]

87 [mg/m3]

520 [mg/m3]

Personal Protective Equipment (PPE)Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:

Safety data

PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
ridadr
UN 3265 8/PG 2
hs_code
29209085
risk_code
34-37
Signal word
Danger
Symbol(GHS)
GHS05,GHS07
hazard_code
C
safety_code
26-36/37/39-45-7-24/25-23
hazard_class
8
Storage Class
8A - Combustible corrosive hazardous materials
packing_group
III
Hazard statements
H302-H314
Limited Quantities
1.0 L (0.3 gallons) (liquid) or 1 Kg (2.2 lbs) (solid)
Excepted Quantities
Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations
Active
Hazard Classifications
Acute Tox. 4 OralEye Dam. 1Skin Corr. 1B
Precautionary statements
P270-P280-P301+P312-P303+P361+P353-P304+P340+P310-P305+P351+P338

General DescriptionA clear colorless to light yellow liquid with a pungent odor. Insoluble in water and denser than water. Hence sinks in water. Contact may severely irritate skin, eyes and mucous membranes. Flash point above 235°F.

Preparation methods · 1 item

PreparationThe preparation of Diphenyl chlorophosphate is as follows:With a thermometer,Reflux condenser and mechanical agitation120 g of dichloromethane was placed in a 500 ml four-neck reaction flask.7.3 g of N,N-dimethylformamide,Stirring temperature control below 10 °C,Put 28g of bis(trichloromethyl) carbonate,A solution of 50 g of diphenyl phosphate and 120 g of dichloromethane was added.After the addition, the reaction was carried out for 3 hours. After the end of the reaction, the temperature was controlled below 10 ° C, 20 g of water was slowly added, and the mixture was stirred and the organic phase was dried over anhydrous sodium sulfate. The desiccant was removed by filtration, and the filtrate was evaporated under normal pressure. The temperature was lowered to 0 ° C, and the insoluble matter was removed by filtration to obtain 48.9 g of diphenyl chlorophosphate. The purity of GC was 99.2%, and the yield was 90.3%.

Upstream & downstream products

Upstream raw materials

Phenol

Downstream products

N-ACRYLOXYSUCCINIMIDE(Trimethylsilyl)diazomethaneDiphenyl phosphoramidate4,4'-Dipyridyl sulfidePhenyl phosphorodichloriditeTriphenyl phosphateGB-1Diphenyl cyanophosphonatePhosphoric acid, diphenyl tetradecyl esterPhosphoric acid, ethenyl diphenyl ester1,2,3,4-Tetra-O-acetyl-6-diphenylphosphoryl-beta-D-mannopyranose