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Diphenylphosphinyl chloride

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Name

Diphenylphosphinyl chloride

EINECS 216-107-2
CAS No. 1499-21-4 Density 1.25 g/cm3
PSA 26.88000 LogP 3.15430
Solubility Decomposes in water Melting Point 20 °C
Formula C12H10ClOP Boiling Point 369.2 °C at 760 mmHg
Molecular Weight 236.638 Flash Point 177.1 °C
Transport Information UN 2920 8/PG 2 Appearance clear colorless to yellow liquid
Safety 16-26-36/37/39-45 Risk Codes 10-34
Molecular Structure Molecular Structure of 1499-21-4 (Diphenylphosphinyl chloride) Hazard Symbols CorrosiveC,FlammableF
Synonyms

Phosphinicchloride, diphenyl- (6CI,7CI,8CI,9CI);Chlorodiphenylphosphine oxide;Diphenylphosphorus oxychloride;NSC175848;

Article Data 72

Diphenylphosphinyl chloride Synthetic route

1707-03-5

diphenyl-phosphinic acid

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
With thionyl chloride In toluene for 2h; Heating;100%
With phosphorus pentachloride
With thionyl chloride for 2h; Heating;
1079-66-9

chloro-diphenylphosphine

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
With ozone In dichloromethane at -80℃;99%
With sulfur dioxide; chlorine88%
80.3%
644-97-3

Dichlorophenylphosphine

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
With oxygen In toluene for 4h;93%
1041751-59-0

methyl (2R)-2-[(diphenylphosphoryl)(methyl)amino]-2-phenylethanoate

A

methyl (2R)-(methylamino)(phenyl)acetate

B

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
Stage #1: methyl (2R)-2-[(diphenylphosphoryl)(methyl)amino]-2-phenylethanoate With hydrogenchloride; water In methanol for 0.5h;
Stage #2: With sodium hydrogencarbonate In methanol; water
A 90%
B n/a
100-59-4

phenylmagnesium chloride

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
With dibutyl hydrogen phosphite65%
1079-66-9

chloro-diphenylphosphine

67-64-1

acetone

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
for 50h; Ambient temperature;42%
128-09-6

N-chloro-succinimide

4559-70-0

Diphenylphosphine oxide

1499-21-4

Diphenylphosphinic chloride

14278-72-9

diphenylthiophosphinic acid

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
With chlorine
644-97-3

Dichlorophenylphosphine

587-85-9

diphenylmercury(II)

A

1079-66-9

chloro-diphenylphosphine

B

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
at 230 - 240℃;
at 230 - 240℃;
4559-70-0

Diphenylphosphine oxide

1499-21-4

Diphenylphosphinic chloride

Conditions
ConditionsYield
With thionyl chloride
With tetrachloromethane; triethylamine In chloroform at 5℃;
Multi-step reaction with 2 steps
1: dihydrogen peroxide; sodium hydroxide / water / 1 h / 90 - 100 °C
2: thionyl chloride / toluene / 3 h / 80 °C
View Scheme

Diphenylphosphinyl chloride Specification

The IUPAC name of Diphenylphosphinic chloride is [chloro(phenyl)phosphoryl]benzene. With the CAS registry number 1499-21-4 and EINECS 216-107-2, it is also named as Phosphinic chloride, P,P-diphenyl-. The product's categories are Pharmaceutical Intermediates; Phosphorus Compounds; Biochemistry; Coupling Reactions (Peptide Synthesis); Peptide Synthesis; Protection & Derivatization Reagents (for Synthesis); Reagents for Oligosaccharide Synthesis; Synthetic Organic Chemistry. It is clear colorless to yellow liquid which is used in pesticide synthesis and as fire retardant. Additionally, this chemical should be stored at the temperature of 2-8 °C.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 2.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.75; (4)ACD/LogD (pH 7.4): 2.75; (5)ACD/BCF (pH 5.5): 72.67; (6)ACD/BCF (pH 7.4): 72.67; (7)ACD/KOC (pH 5.5): 748.09; (8)ACD/KOC (pH 7.4): 748.09; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 26.88 Å2; (13)Index of Refraction: 1.585; (14)Molar Refractivity: 63.03 cm3; (15)Molar Volume: 187.9 cm3; (16)Polarizability: 24.98×10-24 cm3; (17)Surface Tension: 45.2 dyne/cm; (18)Density: 1.25 g/cm3; (19)Flash Point: 177.1 °C; (20)Enthalpy of Vaporization: 59.17 kJ/mol; (21)Boiling Point: 369.2 °C at 760 mmHg; (22)Vapour Pressure: 2.57E-05 mmHg at 25°C.

Preparation of Diphenylphosphinic chloride: It can be obtained by diphenylphosphinous acid chloride and propan-2-one. This reaction reacts at ambient temperature for 50 hours. The yield is 42%.

Diphenylphosphinic chloride can be obtained by diphenylphosphinous acid chloride and propan-2-one

Uses of Diphenylphosphinic chloride: It can react with 1-methyl-piperazine to get N-(diphenylphosphinyl)-N'-methylpiperazine. This reaction needs solvent CH2Cl2 at temperature of 0 °C. The reaction time is 10 min. The yield is 95%.

Diphenylphosphinic chloride can react with 1-methyl-piperazine to get N-(diphenylphosphinyl)-N'-methylpiperazine

When you are using this chemical, please be cautious about it as the following:
It is flammable and can cause burns, so people should keep away from sources of ignition. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)

People can use the following data to convert to the molecule structure. 
1. SMILES:ClP(=O)(c1ccccc1)c2ccccc2
2. InChI:InChI=1/C12H10ClOP/c13-15(14,11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H
3. InChIKey:QPQGTZMAQRXCJW-UHFFFAOYAH

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