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Phenylphosphonic dichloride

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Name

Phenylphosphonic dichloride

EINECS 212-534-3
CAS No. 824-72-6 Density 1.402 g/cm3
PSA 26.88000 LogP 2.98260
Solubility Soluble in benzene, chloroform, carbon tetrachloride Melting Point 3 °C(lit.)
Formula C6H5Cl2OP Boiling Point 258 °C at 760 mmHg
Molecular Weight 194.985 Flash Point 109.835 °C
Transport Information UN 3265 8/PG 2 Appearance Colorless to light yellow liquid
Safety 26-45-8-36/37/39 Risk Codes 14-34-37
Molecular Structure Molecular Structure of 824-72-6 (Phenylphosphonic dichloride) Hazard Symbols CorrosiveC
Synonyms

Phosphonic dichloride, phenyl- (6CI,8CI,9CI);Phenylphosphonyl dichloride;Benzenephosphonic dichloride;Dichlorophenylphosphine oxide;Benzenephosphonyl chloride;Phenylphosphonic acid dichloride;Phenylphosphonic dichloride;Phenyldichlorophosphine oxide;NSC 66477;

Article Data 65

Phenylphosphonic dichloride Synthetic route

4895-65-2

phenyltetrachlorophosphorane

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With sodium dithionite In tetrachloromethane at 20℃; Substitution;96%
With water
With sulfur dioxide
Multi-step reaction with 2 steps
1: NEt3 / CH2Cl2 / 13 h / 40 °C
2: 38 percent Spectr. / NEt3 / toluene; CH2Cl2 / 4 h / 0 °C
View Scheme
With amino acid at 20 - 25℃;
701-64-4

phosphoric acid monophenyl ester

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20 - 45℃; for 5h;96%
1571-33-1

phenylphosphonate

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide Heating;93%
With phosphorus pentachloride for 2h; Heating;91%
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20 - 40℃; for 1h;
1754-49-0

diethyl phenylphosphonate

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With thionyl chloride; N-Formylpiperidine for 20h; Heating;91.3%
Multi-step reaction with 2 steps
1: hydrogenchloride / 12 h / 100 °C
2: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 5 h / 20 - 45 °C
View Scheme
2240-41-7

dimethyl phenylphosphonate

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With thionyl chloride In N,N-dimethyl-formamide at 120℃; for 4h;88.2%
79-37-8

oxalyl dichloride

2240-41-7

dimethyl phenylphosphonate

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
84%
644-97-3

Dichlorophenylphosphine

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With chlorine; iodine; iron(III) chloride In tetrachloromethane at 60 - 70℃; for 5h;82.5%
With air
With oxygen
75-44-5

phosgene

1571-33-1

phenylphosphonate

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
In chlorobenzene75%
With pyridine In chlorobenzene
75-44-5

phosgene

1754-49-0

diethyl phenylphosphonate

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
71%
25331-57-1

phenyl-phosphonothioic acid

824-72-6

P,P-dichlorophenylphosphine oxide

Conditions
ConditionsYield
With pyridine; thionyl chloride for 4h; Heating;70%

Phenylphosphonic dichloride Specification

The Phenylphosphonic dichloride, with the CAS registry number 824-72-6, is also known as Dichlorophenylphosphine oxide. It belongs to the product categories of Ligand; Organophosphorus compound. Its EINECS number is 212-534-3. This chemical's molecular formula is C6H5Cl2OP and molecular weight is 194.98. What's more, its systematic name is Phenylphosphonic dichloride. This chemical is stable at common pressure and temperature, and it should be sealed and stored in containers with dry inert gas which are placed in a cool and dry place. Moreover, it should be protected from oxides, heat and fire.

Physical properties of Phenylphosphonic dichloride are: (1)ACD/LogP: 1.537; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.54; (4)ACD/LogD (pH 7.4): 1.54; (5)ACD/BCF (pH 5.5): 8.68; (6)ACD/BCF (pH 7.4): 8.68; (7)ACD/KOC (pH 5.5): 163.39; (8)ACD/KOC (pH 7.4): 163.39; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.88 Å2; (13)Index of Refraction: 1.533; (14)Molar Refractivity: 43.155 cm3; (15)Molar Volume: 139.108 cm3; (16)Polarizability: 17.108×10-24cm3; (17)Surface Tension: 41.4 dyne/cm; (18)Density: 1.402 g/cm3; (19)Flash Point: 109.835 °C; (20)Enthalpy of Vaporization: 47.557 kJ/mol; (21)Boiling Point: 258 °C at 760 mmHg; (22)Vapour Pressure: 0.02 mmHg at 25°C.

Preparation: this chemical can be prepared by phenylphosphonous acid dichloride at the temperature of 60 - 70 °C. This reaction will need reagent Cl2 and solvent CCl4 with the reaction time of 5 hours. This reaction will also need catalysts FeCl3, I2. The yield is about 82.5%.

Phenylphosphonic dichloride can be prepared by phenylphosphonous acid dichloride at the temperature of 60 - 70 °C

Uses of Phenylphosphonic dichloride: it can be used to produce 2-phenyl-[1,3,2]dioxaphosphepane-2-oxide by heating. It will need reagent pyridine and solvent tetrahydrofuran with the reaction time of 12 hours. The yield is about 58%.

Phenylphosphonic dichloride can be used to produce 2-phenyl-[1,3,2]dioxaphosphepane-2-oxide by heating

When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. It will react violently with water, and you must keep the container dry. It is irritating to respiratory system. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective gloves and eye/face protection. In case of accident or if you feel unwell, you should seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: ClP(=O)(Cl)c1ccccc1
(2)Std. InChI: InChI=1S/C6H5Cl2OP/c7-10(8,9)6-4-2-1-3-5-6/h1-5H
(3)Std. InChIKey: IBDMRHDXAQZJAP-UHFFFAOYSA-N

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