Phosphorodichloridic acid, phenyl ester

HCID 13038

Basic information

CAS
770-12-7
Standard SMILES
O=P(Cl)(Cl)Oc1ccccc1
InChIKey
TXFOLHZMICYNRM-UHFFFAOYSA-N
Molecular formula
C6H5Cl2O2P
Average molar mass
210.98 g/mol
Monoisotopic mass
209.94042139

Overview

Monophenyl dichlorophosphate appears as a liquid. May severely irritate skin, eyes and mucous membranes.

Names & identifiers

Preferred name
Phosphorodichloridic acid, phenyl ester
IUPAC
dichlorophosphoryloxybenzene
English name
Phenyl dichlorophosphate
Molecular formula
C6H5Cl2O2P
Molecular weight
210.98

Names & synonyms

PHENYL DICHLOROPHOSPHATE770-12-7Phenyl phosphorodichloridatePhosphorodichloridic acid, phenyl esterDichlorophenoxyphosphine oxidePhenylphosphoric dichloridePhenoxydichlorophosphine oxidePhenyl phosphorodichlorodatePhenoxyphosphoryl dichloridePhosphoroyl dichloride phenyl esterPCDPAE85WW9S5Z
Show more names
O-phenyl phosphorodichloridateMPCPorophosphatePhenyl dichlorophospPicaridin Impurity 7Phenyl dichlorophosphatDichlorophenylphosphate
Phosphorodichloridic acid phenyl esterDichlorophenoxyphosphineNSC-44412DTXSID6044987RefChem:861583DTXCID4024987212-220-6dichlorophosphoryloxybenzene

Database identifiers

CAS
770-12-7
PubChem CID
13038
DTXSID
DTXSID6044987
UNII
AE85WW9S5Z
EC Number
212-220-6
Nikkaji
J32.905C

Properties

Computed structural properties

XLogP
2.8
Topological polar surface area
26.3 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organophosphates, Other
SpringerMaterials PropertiesBoiling point
Physical Description · 2 items

Monophenyl dichlorophosphate appears as a liquid. May severely irritate skin, eyes and mucous membranes.

Liquid; [Merck Index] Colorless liquid; [Alfa Aesar MSDS]

Physicochemical properties

Melting point
-1 °C · -1 °C
Boiling point
241 · 241-243 °C (lit.)
Density
1.412 g/mL · 1.412 g/mL at 25 °C (lit.)
vapor pressure
2.33 Pa · 2.33Pa at 25℃
refractive index
20 · n20/D 1.523(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (15.3%): Harmful if swallowed [Warning Acute toxicity, oral]

P260, P264, P264+P265, P270, P273, P280, P301+P317, P301+P330+P331, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P330, P363, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 85 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Phosphorodichloridic acid, phenyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phosphorodichloridic acid, phenyl 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: 27-10-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/20440

Phenyl dichlorophosphate: Does not have an individual approval but may be used under an appropriate group standard

DOT LabelCorrosive
Fire HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Health HazardsExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Hazards Summary · 1 item

May cause severe skin, eye, and mucous membrane irritation; [CAMEO] Reacts violently with water; Causes burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Toxic by ingestion; Highly toxic by skin absorption; Dermal LD50 (guinea pig) = 14-400 mg/kg; [Alfa Aesar MSDS] See Dimethyl phosphorochloridothioate, Diethylthiophosphoryl chloride, and Diethyl chlorophosphate.

Reactive GroupEsters, Sulfate Esters, Phosphate Esters, Thiophosphate Esters, and Borate Esters

Safety & protection

Fire FightingExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
First AidExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Nonfire Spill ResponseExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Isolation and EvacuationExcerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Toxicology

Adverse EffectsDermatotoxin - Skin burns.

Safety data

F
10
PPE
Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
TD4393000
ridadr
UN 3265 8/PG 2

Chemistry & industry

Uses & manufacturing

UsesUsed in studies of decarbamylation of carbamylated acetylcholinesterase. [ChemIDplus] Used in organic syntheses; [Merck Index]
U.S. Production2023: <50,000 lb
General Manufacturing InformationPhosphorodichloridic acid, phenyl ester: ACTIVE
Applications · 4 items

UsesReagent for the preparation of phosphate diesters.

UsesReagent for preparation of phosphate diesters. Phenyl dichlorophosphate is used in the preparation of symmetrical phosphate diesters. It is used as a phosphorylating agent for alcohols and amines. It is also involved in the preparation of phenylphosphoro di-(1-imidazolidate) and 2-phenyl-bis-triazoloylphosphate, which is used in peptide synthesis. It plays a vital role in the Pfitzner-Moffatt oxidation which involves oxidation of alcohols to the corresponding aldehydes and ketones. Furthermore, it is utilized in Beckmann rearrangement for the preparation of N-phenylacetamide from acetophenone oxime.

UsesIn organic synthesis for preparation of lactams, phosphate diesters and for oxidation reactions.

General DescriptionA liquid. May severely irritate skin, eyes and mucous membranes.

Preparation methods · 1 item

PreparationThe preparation of Phenyl dichlorophosphate is as follows:160 g (1 mol) of phosphorus oxychloride and 1 g of titanium tetrachloride were respectively added to a four-necked flask to carry out the reaction, and the temperature was raised to 70-80° C., and phenol (94 g, 1 mol) was slowly added dropwise. The phenol addition time was about 2- 3 hours,After completion of the dropwise addition, the reaction is maintained at 80-90° C. for 3-5 hours. After no hydrogen chloride is evolved, the reaction is completed. After the reaction, the phosphorus oxychloride is distilled under reduced pressure, the vacuum degree is 30-100 KPa, and the distillation temperature is 30-100° C. Distillation under reduced pressure to obtain the intermediate of the mixture, a mono-substituted and di-substituted mixture of phosphorus oxychloride, the ratio of the mixture is 5:5, gas phase analysis to obtain the intermediate of the mixture, the yield of the intermediate is 95%, phosphorus oxychloride The recovery rate is 95% (calculated as phosphorus oxychloride).

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南京一化生物科技有限公司13429882898; 13429882898

Related reactions

81 records

Compound notes

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