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Basic Information
CAS No.: 644-97-3
Name: Dichlorophenylphosphine
Article Data: 94
Molecular Structure:
Molecular Structure of 644-97-3 (Dichlorophenylphosphine)
Formula: C6H5Cl2P
Molecular Weight: 178.985
Synonyms: Phosphonousdichloride, phenyl- (6CI,8CI,9CI);NSC 66478;Phenylphosphorus dichloride;Phenyldichlorophosphine;Phenylphosphine dichloride;Phenylphosphinous dichloride;Phenylphosphonous acid dichloride;Phosphine, dichlorophenyl-;Benzenephosphorus Dichloride;
EINECS: 211-425-8
Density: 1.319g/mLat 25°C(lit.)
Melting Point: -51 °C(lit.)
Boiling Point: 224 °C at 760 mmHg
Flash Point: 89.272 °C
Solubility: Slightly soluble in water, soluble in ethanol, acetone, diethyl ether
Appearance: Colorless to light yellow liquid
Hazard Symbols: FlammableF,ToxicT
Risk Codes: 17-25-34-29
Safety: 26-28-36/37/39-43-45
Transport Information: UN 2845 4.2/PG 1
PSA: 13.59000
LogP: 3.10140
Synthetic route
71-43-2

benzene

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With aluminium trichloride; phosphorus trichloride for 3h; Heating;96%
Stage #1: benzene With aluminum (III) chloride; phosphorus trichloride for 5h; Reflux; Sealed tube;
Stage #2: With trichlorophosphate In Petroleum ether for 1h; Concentration; Reflux; Sealed tube;
95.5%
With phosphorus trichloride for 2h; Time; Reflux;93.6%
108-90-7

chlorobenzene

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With phosphorus; phosphorus trichloride at 70 - 350℃; under 30003 Torr; for 6h; Concentration; Pressure; Temperature;94.35%
With phosphorus; phosphorus trichloride at 390℃;58.9%
With phosphorus; nickel; phosphorus trichloride at 390℃; Product distribution; other catalysts;33.1%
824-72-6

P,P-dichlorophenylphosphine oxide

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With triphenylphosphine91%
603-35-0

triphenylphosphine

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With phosphorus trichloride at 350℃; for 5h;85%

1,1,3,3-Tetrafluoro-4,6-bis-trifluoromethyl-1,3-dihydro-isobenzofuran

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With aluminium trichloride; phosphorus trichloride for 5h; Heating;84%
638-21-1

phenylphosphane

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With phosphorus pentachloride In diethyl ether at 20℃;83%
With phosphorus pentachloride In toluene
4895-65-2

phenyltetrachlorophosphorane

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With tetraethylammonium iodide In benzene for 1h;79%
With phosphorous acid trimethyl ester; triethyl phosphite
55045-25-5

phenyltrichlorophosphonium hexachlorophosphorate

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With diethyl phosphorylchloridite In benzene for 6h; also with EtOPCl2;72%
With difluoro diethylamino phosphine In benzene for 0.5h;
With difluoro diethylamino phosphine In benzene for 0.5h; other substrates;
23588-02-5

ethyl phenylphosphonochloridothioite

108-94-1

cyclohexanone

A

60340-72-9

chloroanhydride of phenyl-α-hydroxycyclohexylphosphinic acid

B

1779-48-2

phenylphosphinic acid

C

67176-71-0

C6H6ClOP

D

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
With acetic acid at 0℃; for 240h;A 50%
B n/a
C n/a
D n/a
75589-83-2

N,N-dimethylamino-P-phenyl-C-methylmethylenephosphine

931-59-9

benzenesulfenyl chloride

A

26990-26-1

S-phenyl-P-phenyldithiophosphonous chloride

B

38476-60-7

S,S-diphenyl-P-phenyldithiophosphonite

C

644-97-3

Dichlorophenylphosphine

Conditions
ConditionsYield
In acetonitrileA n/a
B 20%
C n/a
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Reported in EPA TSCA Inventory.

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DOT Classification:  8; Label: Corrosive

Specification

The Dichlorophenylphosphine, with the CAS registry number 644-97-3, is also known as Phenyldichlorophosphine. It belongs to the product categories of Chlorophosphines; Pharmaceutical Intermediates; Ligand; Organophosphine halide. Its EINECS number is 211-425-8. This chemical's molecular formula is C6H5Cl2P and molecular weight is 178.98. What's more, its systematic name is Phenylphosphonous dichloride. This colourless viscous liquid is commonly used in the synthesis of phosphine ligands. Dichlorophenylphosphine is commercially available. It may be prepared by a electrophilic substitution of benzene by phosphorus trichloride, catalyzed by aluminium chloride. This chemical should be sealed and stored in a cool and dry place. Moreover, it should be protected from oxides, acids, heat and fire.

Physical properties of Dichlorophenylphosphine are: (1)ACD/LogP: 2.421; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.42; (4)ACD/LogD (pH 7.4): 2.42; (5)ACD/BCF (pH 5.5): 40.76; (6)ACD/BCF (pH 7.4): 40.76; (7)ACD/KOC (pH 5.5): 494.52; (8)ACD/KOC (pH 7.4): 494.52; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 13.59 Å2; (13)Flash Point: 89.272 °C; (14)Enthalpy of Vaporization: 44.176 kJ/mol; (15)Boiling Point: 224 °C at 760 mmHg; (16)Vapour Pressure: 0.1 mmHg at 25°C.

Preparation: this chemical can be prepared by benzene by heating. This reaction will need reagents PCl3, AlCl3 with the reaction time of 3 hours. The yield is about 96%.

Dichlorophenylphosphine can be prepared by benzene by heating

Uses of Dichlorophenylphosphine: it can be used to produce phenyl-phosphonous acid diisopropyl ester at the ambient temperature. It will need reagent pyridine and solvent hexane with the reaction time of 3 hours. The yield is about 76%.

Dichlorophenylphosphine can be used to produce phenyl-phosphonous acid diisopropyl ester at the ambient temperature

When you are using this chemical, please be cautious about it as the following:
This chemical can cause buins, and is spontaneously flammable in air. When contact with water, it will liberate toxic gas. It is toxic if swallowed. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. After contact with skin, you must wash immediately with plenty of ... (to be specified by the manufacturer). When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of fire use ... (indicate in the space the precise type of fire-fighting equipment. If water increases the risk add - Never use water). In case of accident or if you feel unwell, you need to seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: ClP(Cl)c1ccccc1
(2)Std. InChI: InChI=1S/C6H5Cl2P/c7-9(8)6-4-2-1-3-5-6/h1-5H
(3)Std. InChIKey: IMDXZWRLUZPMDH-UHFFFAOYSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 100mg/kg (100mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
National Technical Information Service. Vol. 0TS0555341,
mouse LDLo intraperitoneal 100mg/kg (100mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
National Technical Information Service. Vol. 0TS0555341,
rat LD50 oral 200mg/kg (200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
National Technical Information Service. Vol. 0TS0555341,
rat LDLo intraperitoneal 100mg/kg (100mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
National Technical Information Service. Vol. 0TS0555341,