Phenylphosphonic dichloride supplier

Name
Phenylphosphonic dichloride
EINECS 212-534-3
CAS No. 824-72-6
Article Data65
CAS DataBase
Density 1.402 g/cm³
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
Hazard Symbols C
Synonyms Phosphonic dichloride, phenyl- (6CI,8CI,9CI);Phenylphosphonyl dichloride;Benzenephosphonic dichloride;Dichlorophenylphosphine oxide;Benzenephosphonyl chloride;Phenylphosphonic acid dichloride;Phenylphosphonic dichloride;Phenyldichlorophosphine oxide;NSC 66477;
PSA 26.88000
LogP 2.98260

Synthetic route

: 4895-65-2
phenyltetrachlorophosphorane

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
	84%

: 644-97-3
Dichlorophenylphosphine

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
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

Conditions	Yield
In chlorobenzene	75%
With pyridine In chlorobenzene

: 75-44-5
phosgene

: 1754-49-0
diethyl phenylphosphonate

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
	71%

: 25331-57-1
phenyl-phosphonothioic acid

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

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

: 6231-03-4
diethyl phenylphosphonothioate

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With pyridine; thionyl chloride for 4h; Heating;	50%

: 603-35-0
triphenylphosphine

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With trichlorophosphate at 325℃; for 2h;	31%

: 96-31-1
N,N'-Dimethylurea

: 131561-32-5
2,2-Dichlor-1,3-dimethyl-2-phenyl-2λ5-phosphetidin-4-on

A: 824-72-6
P,P-dichlorophenylphosphine oxide

B: 126695-50-9
1,3 Dimethyl-2-phenyl-1,3,2-diazaphosphetidin-4-on-2-oxid

C: 74411-89-5
1,3,5,7-Tetramethyl-4-phenyl-1,3,5,7-tetraaza-4λ5-phosphaspiro<3.3>heptan-2,6-dion

Conditions

Conditions	Yield
With triethylamine In dichloromethane; toluene at 0℃; for 4h;	A 38 % Spectr. B 26 % Spectr. C 6%

...Expand

: 1571-33-1
phenylphosphonate

: 4895-65-2
phenyltetrachlorophosphorane

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 1779-48-2
phenylphosphinic acid

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With phosphorus pentachloride unter Kuehlung;

: 4895-65-2
phenyltetrachlorophosphorane

: 64-19-7
acetic acid

A: 824-72-6
P,P-dichlorophenylphosphine oxide

B: 75-36-5
acetyl chloride

...Expand

: 71-43-2
benzene

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With phosphorus pentoxide at 275℃; beim Erwaermen des Reaktionsprodukts mit PCl5 und POCl3;

: 96-31-1
N,N'-Dimethylurea

: 4895-65-2
phenyltetrachlorophosphorane

A: 824-72-6
P,P-dichlorophenylphosphine oxide

B: 131561-32-5
2,2-Dichlor-1,3-dimethyl-2-phenyl-2λ5-phosphetidin-4-on

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 40℃; for 13h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 90876-60-1
trichloro(2-ethoxyvinyl)phenylphosphorane

A: 824-72-6
P,P-dichlorophenylphosphine oxide

B: 90876-11-2
phenyl-β-ethoxyvinylphosphinic chloride

C: (1-chloro-2-ethoxyvinyl)phenylphosphinic chloride

D: (1,1,2-trichloro-2-ethoxyethyl)phenylphosphinic chloride

Conditions

Conditions	Yield
With sulfuryl dichloride In benzene at -3 - 0℃;

...Expand

: 4895-65-2
phenyltetrachlorophosphorane

A: 824-72-6
P,P-dichlorophenylphosphine oxide

B: 644-97-3
Dichlorophenylphosphine

Conditions

Conditions	Yield
With Diethyl phosphate In benzene for 1h; Product distribution; (C2H5O)2PONa;

: 135289-86-0
C8H8Cl4NOP

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With sulfur dioxide In toluene at 0 - 5℃;	14.2 g

: 135289-88-2
C10H12Cl4NOP

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With sulfur dioxide In toluene at 0 - 5℃;	15.9 g

: 135289-87-1
C10H12Cl4NOP

: 824-72-6
P,P-dichlorophenylphosphine oxide

Conditions

Conditions	Yield
With sulfur dioxide In toluene at 0 - 5℃;	9.9 g

: 644-97-3
Dichlorophenylphosphine

oxygen: oxygen

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 4895-65-2
phenyltetrachlorophosphorane

sulfur dioxide: sulfur dioxide

A: 824-72-6
P,P-dichlorophenylphosphine oxide

B: 7719-09-7
thionyl chloride

...Expand

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 29841-69-8
(S,S)-1,2-diphenyl-1,2-diaminoethane

: (S3,S4)-1-phenyl-(3,4-diphenyl)diazaphospholidine 1-oxide

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 53354-75-9
meso-1,2-bis(1-hydroxyethyl)benzene

: 679430-35-4
meso-1,5-dimethyl-3-phenyl-1,5-dihydro-benzo[e][1,3,2]dioxa-phosphepine-3-oxide

Conditions

Conditions	Yield
With pyridine In dichloromethane at 0℃; for 1h;	100%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 2216-51-5
(-)-menthol

A: 31352-60-0, 31352-61-1, 54353-18-3
(1R,2S,5R)-5-methyl-2-(propan-2-yl)cyclohexyl phenylphosphinate

B: (-)-menthyl chloride

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 12h;	A 99.6% B n/a

...Expand

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 64-17-5
ethanol

: 1754-49-0
diethyl phenylphosphonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 1h; Substitution;	99%
With triethylamine In diethyl ether at 0 - 20℃; Inert atmosphere; Schlenk technique;	97%
With pyridine In diethyl ether for 6h; Ambient temperature;	92%
With pyridine

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 107-18-6
allyl alcohol

: 2948-89-2
phenylphosphonic acid diallyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In dichloromethane at 0 - 20℃; Substitution;	98%
With pyridine at 2 - 5℃; for 6h;	97.7%
With pyridine In benzene Ambient temperature;	65%
With pyridine

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 75-64-9
tert-butylamine

: 15916-99-1
N,N'-Di-tert-butyl-P-phenylphosphonyldiamid

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.166667h; Sonication; Green chemistry;	98%
In acetonitrile for 3h; Heating;	64%
In acetonitrile Cooling with ice;	64%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 107-10-8
propylamine

: 14360-80-6
bis(propylamino)phenylphosphine oxide

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0833333h; Sonication; Green chemistry;	98%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: trimethyl ammonium 8,8'-dihydroxy-bis(1,2-dicarbollido)-3-cobalt(1-)ate

: potassium hydroxide

: [8,8'-μ-PhP(O)(O)2<(1,2-C2B9H10)2-3,3'-Co]K

Conditions

Conditions	Yield
With triethylamine In chloroform to soln. Et3N in CHCl3 PhPOCl2 was added followed by suspn. cobaltcarborane in CHCl3 and stirred for 1 h at 80°C., soln. was cooled , water was added and stirred for 4 h at room temp., chloroform layer was separated and evapd.,; residue was dissolved in soln. KOH in aq. EtOH, organics were evapd., EtOH was added and heated to 80°C followed by cooling;	97.5%

...Expand

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 109-73-9
N-butylamine

: 14360-81-7
P-phenyl-N,N'-di-n-butylphosphonic diamide

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0833333h; Sonication; Green chemistry;	97%
In diethyl ether for 0.5h; Ambient temperature;	41%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 108-91-8
cyclohexylamine

: 14612-96-5
Bis(cyclohexylamino)phenylphosphine oxide

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0833333h; Sonication; Green chemistry;	97%
In acetonitrile at 0℃; for 24h;	60%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 219928-13-9
1-(3-bromophenyl)-pyrrolidine

: phenylbis(3-(pyrrolidin-1-yl)phenyl)phosphine oxide

Conditions

Conditions	Yield
Stage #1: 1-(3-bromophenyl)-pyrrolidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: P,P-dichlorophenylphosphine oxide In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;	97%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 122-39-4
diphenylamine

: 107822-55-9
bis(diphenylamino)phenylphosphine oxide

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.25h; Sonication; Green chemistry;	97%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 95-54-5
1,2-diamino-benzene

: 7597-43-5
1,3-dihydro-2-phenyl-1,3,2-benzodiazaphosphole-2-oxide

Conditions

Conditions	Yield
In various solvent(s) at 135℃;	96.8%
In various solvent(s) at 135℃; other diamines, other phophonates;	96.8%
With bromobenzene Heating;

: 110-85-0
piperazine

: 824-72-6
P,P-dichlorophenylphosphine oxide

: phenylbis(1-piperazinyl)phosphine oxide

Conditions

Conditions	Yield
With triethylamine In chloroform at -5 - 25℃; for 2.5h; Inert atmosphere;	96.5%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 1-methyl-1-sila-2,6,7-trioxa-4-hydroxymethylbicyclo[2,2,2]octyl

: C18H27O9PSi2

Conditions

Conditions	Yield
In 1,1,2,2-tetrachloroethane at 35 - 120℃; for 7h; Temperature; Inert atmosphere;	96.1%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 16047-86-2
2,2-dimethyl-3-(methylamino)propan-1-ol

: 3,5,5-Trimethyl-2-phenyl-[1,3,2]oxazaphosphinane 2-oxide

Conditions

Conditions	Yield
With triethylamine In benzene for 20h; Ambient temperature;	96%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 71-36-3
butan-1-ol

: 2062-48-8
Phenylphosphonsaeure-n-butylesterfluorid

Conditions

Conditions	Yield
With sodium fluoride In acetonitrile for 1h; Heating;	96%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 98-54-4
para-tert-butylphenol

: 89410-43-5
bis(4-tert-butylphenyl) phenylphosphonate

Conditions

Conditions	Yield
With pyridine at 140℃; for 20h;	96%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 527-60-6
Mesitol

: 1160309-46-5
bis(2,4,6-trimethylphenyl) phenylphosphonate

Conditions

Conditions	Yield
With pyridine at 140℃; for 20h;	96%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 1,1-dimethyl-1-sila-2,6-dioxa-4-oxy-4-phospha-4-hydroxymethylcyclohexane

: C16H29O9P3Si2

Conditions

Conditions	Yield
With pyridine In diethylene glycol dimethyl ether at 30 - 140℃; for 11h; Temperature; Solvent; Reagent/catalyst;	95.6%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 118-79-6
2,4,6-tribromophenol

: C18H9Br6O3P

Conditions

Conditions	Yield
With ammonia In chloroform at 55℃; for 2h; Temperature; Concentration; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube;	95.3%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 1067-12-5
tri(hydroxymethyl)phosphine oxide

: C9H12O5P2

Conditions

Conditions	Yield
In 5,5-dimethyl-1,3-cyclohexadiene at 20 - 140℃; for 6h; Solvent; Temperature;	95.3%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 78-92-2, 15892-23-6
iso-butanol

: 2783-48-4
di-sec-butyl phenylphosphonate

Conditions

Conditions	Yield
With pyridine In benzene Ambient temperature;	95%
With pyridine

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 4128-31-8
rac-octan-2-ol

: 107465-90-7
di-2-octyl phenylphosphonate

Conditions

Conditions	Yield
With pyridine In benzene Ambient temperature;	95%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 100-46-9
benzylamine

: 53721-41-8
bis(benzylamino)phenylphosphine oxide

Conditions

Conditions	Yield
In neat (no solvent) at 20℃; for 0.0833333h; Sonication; Green chemistry;	95%
In tetrahydrofuran for 4h; Ambient temperature;	83%
With pyridine at 70℃; for 4.5h;	82%
In diethyl ether at 0 - 20℃; for 2h;	59%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 68737-65-5
(R,R)-N,N'-dimethyl-1,2-diaminocyclohexane

: 184535-50-0
(R3a,R7a)-(1,3-dimethyl)-2-phenyl-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3,2-benzodiazaphosphole 2-oxide

Conditions

Conditions	Yield
With triethylamine In benzene for 1.5h; Ambient temperature;	95%

: 824-72-6
P,P-dichlorophenylphosphine oxide

: 86318-61-8
(tert-butyldimethylsilyl)acetylene

: bis(2-(tert-butyldimethylsilyl)-1-ethynyl)(phenyl)phosphine oxide

Conditions

Conditions	Yield
Stage #1: (tert-butyldimethylsilyl)acetylene With n-butyllithium In tetrahydrofuran; hexane at -75 - -55℃; for 0.416667h; Inert atmosphere; Stage #2: P,P-dichlorophenylphosphine oxide In tetrahydrofuran; hexane at -70 - 20℃; for 1.95h; Inert atmosphere;	95%

: 448905-30-4
2-bromo-N-(furan-2-ylmethyl)prop-2-en-1-amine

: 824-72-6
P,P-dichlorophenylphosphine oxide

: N-(2-bromoallyl)-N-(furan-2-ylmethyl)-P-phenyl phosphonamidic chloride

Conditions

Conditions	Yield
With dmap In dichloromethane at 0 - 20℃; for 2h;	95%

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

Product Name

Phenylphosphonic dichloride

Synthetic route

Phenylphosphonic dichloride Specification

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