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770-12-7

Basic Information
CAS No.: 770-12-7
Name: Phenyl dichlorophosphate
Molecular Structure:
Molecular Structure of 770-12-7 (Phenyl dichlorophosphate)
Formula: C6H5Cl2O2P
Molecular Weight: 210.98
Synonyms: Phenylphosphorodichloridate (6CI);Dichlorophenoxyphosphineoxide;NSC 44412;Phenoxydichlorophosphine oxide;Phenoxyphosphoryl dichloride;Phosphorodichloridic acid, phenyl ester;Phenylphosphoricdichloride;
EINECS: 212-220-6
Density: 1.466 g/cm3
Melting Point: -1 °C
Boiling Point: 242 °C at 760 mmHg
Flash Point: 99.1 °C
Solubility: Decomposes
Appearance: colorless transparent liquid
Hazard Symbols: CorrosiveC
Risk Codes: 34
Safety: 26-36/37/39-45
Transport Information: UN 3265 8/PG 2
PSA: 36.11000
LogP: 3.65110
Synthetic route
3426-89-9

phenyl phosphorodichloridite

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With ozone In dichloromethane at 0℃;99%
108-95-2

phenol

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With triethylamine; trichlorophosphate In tert-butyl methyl ether at -55 - 20℃; for 4h;98%
With magnesium chloride; trichlorophosphate at 80 - 95℃; for 5h; Large scale;91.5%
With triethylamine; trichlorophosphate In diethyl ether at -78 - 20℃; Inert atmosphere;85%
139-02-6

sodium phenoxide

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With tetrabutylammomium bromide; trichlorophosphate In toluene for 1h;90%
19579-04-5

tetrachlorophenoxyphosphorane

109-92-2

ethyl vinyl ether

A

770-12-7

O-phenyl phosphorodichloridate

B

phenyl (2-ethoxyvinyl)-phosphonochloridate

Conditions
ConditionsYield
With sulfur dioxide In benzene at 0 - 5℃;A 32.5%
B 67.1%
108-95-2

phenol

A

115-86-6

phosphoric acid triphenyl ester

B

770-12-7

O-phenyl phosphorodichloridate

C

2524-64-3

chlorophosphoric acid diphenyl ester

Conditions
ConditionsYield
With magnesium chloride; trichlorophosphate In xylene at 90 - 110℃; Kinetics; Product distribution; Rate constant;
With trichlorophosphate at 102 - 240℃;
phenyl sulfate potassium

phenyl sulfate potassium

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With phosphorus pentachloride
phosphoric acid phenyl ester tetrachloride

phosphoric acid phenyl ester tetrachloride

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With sulfur dioxide
108-95-2

phenol

phosphorous oxychloride

phosphorous oxychloride

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With triethylamine In diethyl ether at 0℃; for 0.5h; Yield given;
108-95-2

phenol

A

770-12-7

O-phenyl phosphorodichloridate

B

phosphoric acid diphenyl ester chloride , triphenyl phosphate

phosphoric acid diphenyl ester chloride , triphenyl phosphate

Conditions
ConditionsYield
With trichlorophosphate
7719-12-2, 52843-90-0

phosphorus trichloride

108-95-2

phenol

A

770-12-7

O-phenyl phosphorodichloridate

B

2524-64-3

chlorophosphoric acid diphenyl ester

Conditions
ConditionsYield
at 140℃;
660-68-4

diethyl amine hydrochloride

108-95-2

phenol

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With trichlorophosphate
108-95-2

phenol

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
In not given react. of POCl3 with C6H5OH;;
In not given react. of POCl3 with C6H5OH;;
108-95-2

phenol

A

61274-57-5

Phenylchlorophosphonic Acid Phenyl Ester

B

770-12-7

O-phenyl phosphorodichloridate

Conditions
ConditionsYield
With titanium tetrachloride; trichlorophosphate at 70 - 90℃; Reagent/catalyst; Temperature; Overall yield = 95 %;
770-12-7

O-phenyl phosphorodichloridate

701-64-4

phosphoric acid monophenyl ester

Conditions
ConditionsYield
With silver nitrate In acetonitrile at 0 - 5℃; for 1h; Hydrolysis;100%
With water at 20℃;
With diethyl ether; water
5557-81-3, 5557-83-5, 34404-37-0

L-alanine benzyl ester hydrochloride

770-12-7

O-phenyl phosphorodichloridate

183370-70-9

phenyl(benzyloxy-L-alaninyl)phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78℃; for 1h; Inert atmosphere;100%
With triethylamine In dichloromethane at -80 - 20℃;98%
With triethylamine In dichloromethane at -78 - 20℃; for 2.5h; Inert atmosphere;95%
770-12-7

O-phenyl phosphorodichloridate

39613-92-8, 62062-56-0, 62062-65-1

alanine isopropyl ester hydrochloride

261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In tert-butyl methyl ether at -65 - -50℃; for 2h; Inert atmosphere; Cooling with acetone-dry ice;100%
With triethylamine In tert-butyl methyl ether at -55℃; for 2h;100%
With triethylamine In dichloromethane at -78 - 20℃; for 2.5h; Inert atmosphere;93%

3-((4-cyclobutylbutyl)sulfonyl)propan-1-ol

770-12-7

O-phenyl phosphorodichloridate

3-((4-cyclobutylbutyl)sulfonyl)propyl phenyl (S)-phosphorochloridate

Conditions
ConditionsYield
With 2,6-dimethylpyridine In tetrahydrofuran at 0 - 20℃; for 18h;100%
612-14-6

phthalyl alcohol

770-12-7

O-phenyl phosphorodichloridate

49785-03-7

2-phenoxy-2-oxo-5,6-benzo-1,3,2-dioxaphosphepane

Conditions
ConditionsYield
With triethylamine In ethyl acetate for 48h;99.5%
770-12-7

O-phenyl phosphorodichloridate

(S)-1-isopropylallylamine hydrochloride

345898-62-6

(NHC6H11)2PO2C6H5

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 3.5h;99%
With dmap; triethylamine In dichloromethane Heating;
3182-93-2

(L)-phenylalanine ethyl ester hydrochloride

770-12-7

O-phenyl phosphorodichloridate

287478-21-1

(2S)-ethyl 2-(((RS)-chloro(phenoxy)phosphoryl)amino)-3-phenylpropanoate

Conditions
ConditionsYield
Stage #1: (L)-phenylalanine ethyl ester hydrochloride; O-phenyl phosphorodichloridate In dichloromethane at -78℃; Inert atmosphere;
Stage #2: With triethylamine In dichloromethane at -78 - 20℃;
99%
With triethylamine In dichloromethane at -78 - 20℃;72%
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h;
16652-75-8

L-isoleucine benzyl ester tosylate

770-12-7

O-phenyl phosphorodichloridate

1184942-63-9

phenyl-(benzoxy-L-isoleucinyl)-phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere;99%
39825-33-7

isopropyl L-alanine

770-12-7

O-phenyl phosphorodichloridate

261909-49-3

phenyl(isopropoxy-L-alaninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;99%
With triethylamine In dichloromethane78%
With N-ethyl-N,N-diisopropylamine In dichloromethane at -80℃; for 2h;
18531-99-2

(S)-[1,1']-binaphthalenyl-2,2'-diol

770-12-7

O-phenyl phosphorodichloridate

C26H17O4P

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; Sealed tube;99%
With triethylamine In dichloromethane at 23℃; for 18h;63%
3081-24-1

H-Phe-OEt

770-12-7

O-phenyl phosphorodichloridate

287478-21-1

(2S)-ethyl 2-(((RS)-chloro(phenoxy)phosphoryl)amino)-3-phenylpropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;99%
1738-69-8

L-Leucine benzyl ester

770-12-7

O-phenyl phosphorodichloridate

840506-65-2

phenyl-(benzoxy-L-leucinyl)-phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;99%
2491-20-5

L-alanine methyl ester hydrochloride

770-12-7

O-phenyl phosphorodichloridate

142629-80-9

phenyl methoxyalaninyl phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -80 - 20℃;98%
With triethylamine In dichloromethane at -78 - 20℃; for 1h;92%
With triethylamine In dichloromethane at -78 - 20℃; for 2.5h; Inert atmosphere;91%
2743-60-4

L-Leucine ethyl ester

770-12-7

O-phenyl phosphorodichloridate

926308-86-3

phenyl (ethyloxy-L-leucinyl)phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;98%
921-74-4

L-isoleucine ethyl ester

770-12-7

O-phenyl phosphorodichloridate

926309-00-4

ethyl (chloro(phenoxy)phosphoryl)-L-isoleucinate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;98%
16879-02-0

6-chloro-2-hydroxypyridine

39825-33-7

isopropyl L-alanine

770-12-7

O-phenyl phosphorodichloridate

C17H20ClN2O5P

Conditions
ConditionsYield
Stage #1: isopropyl L-alanine; O-phenyl phosphorodichloridate With N-ethyl-N,N-diisopropylamine In dichloromethane at -50 - -5℃; Inert atmosphere;
Stage #2: 6-chloro-2-hydroxypyridine With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 0℃; Inert atmosphere;
97.5%
74115-13-2

5-bromopyridine-3-ol

39825-33-7

isopropyl L-alanine

770-12-7

O-phenyl phosphorodichloridate

C17H20BrN2O5P

Conditions
ConditionsYield
Stage #1: isopropyl L-alanine; O-phenyl phosphorodichloridate With triethylamine In dichloromethane at -50 - -5℃; Inert atmosphere;
Stage #2: 5-bromopyridine-3-ol With triethylamine In dichloromethane at -10 - 0℃; Inert atmosphere;
97.3%
355-28-2

2,2,3,3,4,4,5,5,5-nonafluoropentanol

770-12-7

O-phenyl phosphorodichloridate

70508-50-8

Phosphoric acid bis-(2,2,3,3,4,4,5,5,5-nonafluoro-pentyl) ester phenyl ester

Conditions
ConditionsYield
With lithium chloride for 4h; bath temperature 180 deg C;97%
With calcium chloride at 120℃;
17368-12-6

2-chloropyridin-4-ol

39825-33-7

isopropyl L-alanine

770-12-7

O-phenyl phosphorodichloridate

C17H20ClN2O5P

Conditions
ConditionsYield
Stage #1: isopropyl L-alanine; O-phenyl phosphorodichloridate With N-ethyl-N,N-diisopropylamine In dichloromethane at -50 - -5℃; Inert atmosphere;
Stage #2: 2-chloropyridin-4-ol With N-ethyl-N,N-diisopropylamine In dichloromethane at -10 - 0℃; Inert atmosphere;
97%
7524-50-7

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

770-12-7

O-phenyl phosphorodichloridate

147907-42-4

phenyl methoxyphenylalaninyl phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -70 - 20℃;96.7%
With triethylamine In dichloromethane at -78 - 20℃;
With triethylamine In dichloromethane at -78 - 20℃;
With triethylamine In dichloromethane at -78 - 20℃;
770-12-7

O-phenyl phosphorodichloridate

39648-74-3, 65355-00-2, 65355-14-8

(S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol

C26H25O4P

Conditions
ConditionsYield
Stage #1: (S)-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Inert atmosphere; Sealed tube;
Stage #2: O-phenyl phosphorodichloridate In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Sealed tube;
96%
71989-43-0

methyl O-(1,1-dimethylethyl)-L-threoninate hydrochloride

770-12-7

O-phenyl phosphorodichloridate

phenyl-(methoxy-O-tert-butyl-L-threoninyl) phosphorochloridate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.5h;96%
55456-40-1

benzyl 2-aminoisobutyrate

770-12-7

O-phenyl phosphorodichloridate

840506-42-5

benzyl 2-((chloro(phenoxy)phosphoryl)amino)-2-methylpropanoate

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78 - 20℃; for 1.25h; Inert atmosphere;96%
74115-12-1

5-chloropyridin-3-ol

39825-33-7

isopropyl L-alanine

770-12-7

O-phenyl phosphorodichloridate

C17H20ClN2O5P

Conditions
ConditionsYield
Stage #1: isopropyl L-alanine; O-phenyl phosphorodichloridate With triethylamine In dichloromethane at -50 - -5℃; Inert atmosphere;
Stage #2: 5-chloropyridin-3-ol With triethylamine In dichloromethane at -10 - 0℃; Inert atmosphere;
95.7%
7300-91-6

N-(4-hydroxyphenyl)maleimide

770-12-7

O-phenyl phosphorodichloridate

C26H17N2O8P

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 5 - 7℃; Temperature;95.3%
75-89-8

2,2,2-trifluoroethanol

770-12-7

O-phenyl phosphorodichloridate

Phosphoric acid phenyl ester bis-(2,2,2-trifluoro-ethyl) ester

Conditions
ConditionsYield
With lithium chloride for 8h; bath temperature 160 - 170 deg C;95.2%
for 24h; Alkaline conditions;
770-12-7

O-phenyl phosphorodichloridate

108-93-0

cyclohexanol

dicyclohexyl phenyl phosphate

Conditions
ConditionsYield
With molybdenum(VI) tetrachloride oxide; triethylamine In dichloromethane at 20℃;95%
at 70 - 80℃;
4383-22-6

Allylbenzylamine

770-12-7

O-phenyl phosphorodichloridate

920526-13-2

C16H17ClNO2P

Conditions
ConditionsYield
Stage #1: O-phenyl phosphorodichloridate With dmap; triethylamine In dichloromethane at 20℃; for 0.25h;
Stage #2: Allylbenzylamine In dichloromethane at 20℃; for 3h;
95%
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    Phenyl dichlorophosphate

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  • Phenyl dichlorophosphate   CAS: 770-12-7

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    Phenyl dichlorophosphate CAS: 770-12-7

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    Phenyl dichlorophosphate

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

The Phosphorodichloridic acid, phenyl ester, with its CAS registry number 770-12-7, has the IUPAC name of dichlorophosphoryloxybenzene. For being a kind of clear colourless to very slightly brown liquid, it is sensitive to moisture.

The physical properties of this chemical are as below: (1)ACD/LogP: 2.46; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.46; (4)ACD/LogD (pH 7.4): 2.46; (5)ACD/BCF (pH 5.5): 43.54; (6)ACD/BCF (pH 7.4): 43.54; (7)ACD/KOC (pH 5.5): 518.47; (8)ACD/KOC (pH 7.4): 518.47; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 36.11; (13)Index of Refraction: 1.536; (14)Molar Refractivity: 44.87 cm3; (15)Molar Volume: 143.8 cm3; (16)Polarizability: 17.78×10-24 cm3; (17)Surface Tension: 45.2 dyne/cm; (18)Density: 1.466 g/cm3; (19)Flash Point: 99.1 °C; (20)Enthalpy of Vaporization: 45.96 kJ/mol; (21)Boiling Point: 242 °C at 760 mmHg; (22)Vapour Pressure: 0.0541 mmHg at 25°C; (23)Exact Mass: 209.940421; (24)MonoIsotopic Mass: 209.940421; (25)Topological Polar Surface Area: 26.3; (26)Heavy Atom Count: 11; (27)Complexity: 162.

Use of this chemical: Phosphorodichloridic acid could react with 4-methyl-aniline to produce phosphoric acid-chloride phenyl ester-p-toluidide. This reaction happens in the presence of the reagent of diethyl ether.

Production method of this chemical: phenol could react to produce phosphorodichloridic acid. This reaction happens in the presence of POCl3, with its yield of 70.1 %.


 
As to its usage, it is widely applied in many ways. It could be used as the catalytic agent in the synthesis of Emamectin benzoate; It could also be used to prepare phosphodiesterase and then it is usually applied as the coupling agent of sulfinic acid, alcohol, ammonia and triol. 

When you are dealing with this chemical, you should be very careful. For being a kind of corrosive chemical, it is irritating to respiratory system and may destroy living tissue on contact. And it could causes burns. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. If in case of contact with eyes, rinse immediately with plenty of water and seek medical advice and if in case of accident or if you feel unwell seek medical advice immediately (show the label where possible). 

In addition, you could convert the following datas into the molecular structure:
(1)Canonical SMILES: C1=CC=C(C=C1)OP(=O)(Cl)Cl
(2)InChI: InChI=1S/C6H5Cl2O2P/c7-11(8,9)10-6-4-2-1-3-5-6/h1-5H
(3)InChIKey: TXFOLHZMICYNRM-UHFFFAOYSA-N 

Below are the toxicity information of this chemical:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral 850mg/kg (850mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 39(4), Pg. 86, 1974.