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
Show more names
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
- Formal charge
- 0
- Complexity
- 162
Experimental & physicochemical properties
Physical Description
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
- storage temp.
- 2 · 2-8°C
- solubility
- soluble in Chloroform
- form
- Liquid
- color
- Clear colorless to very slightly brown
- Water Solubility
- Decomposes
- Sensitive
- Moisture Sensitive
- Merck
- 14 · 14,7282
- BRN
- 511863 · 511863
- Stability
- Moisture Sensitive
- InChI
- 1S/C6H5Cl2O2P/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H
- InChIKey
- TXFOLHZMICYNRM-UHFFFAOYSA-N
- SMILES
- ClP(Cl)(=O)Oc1ccccc1
- CAS DataBase Reference
- 770 · 770-12-7(CAS DataBase Reference)
- FDA UNII
- 85 WW9S5Z · AE85WW9S5Z
- NIST Chemistry Reference
- Phosphorodichloridic acid, phenyl ester(770-12-7)
- EPA Substance Registry System
- Phosphorodichloridic acid, phenyl ester (770-12-7)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 5 · GHS05
- Signal word
- Danger
- Hazard statements
- 314 · H314
- Precautionary statements
- 280 · P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
- 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
- RIDADR
- 3265 · UN 3265 8/PG 2
- WGK Germany
- 3 · 3
- RTECS
- 4393000 · TD4393000
- F
- 10 · 10
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- II
- HS Code
- 29209085 · 29209085
- Storage Class
- 8 A · 8A - Combustible corrosive hazardous materials
- Hazard Classifications
- 1 B · Skin 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)
Safety & regulation
GHS classification
GHS Classification
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
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
Hazards Summary
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.
Reactivity Profile
An hologenated organophosphate. Organophosphates are susceptible to formation of 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.
Safety & protection
Toxicology
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
- hs_code
- 29209085
- risk_code
- 34-37
- Signal word
- Danger
- Symbol(GHS)
- GHS05
- hazard_code
- C
- safety_code
- 26-36/37/39-45
- hazard_class
- 8
- Storage Class
- 8A - Combustible corrosive hazardous materials
- packing_group
- II
- Hazard statements
- 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
- Skin Corr. 1B
- Precautionary statements
- P280-P303+P361+P353-P304+P340+P310-P305+P351+P338-P363-P405
Chemistry & industry
Uses & manufacturing
Applications
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
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).
Upstream & downstream products
Downstream products
Suppliers100 total
Related reactions
Compound notes
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