Product Name

  • Name

    6-Chlorobenzo[c][1,2]benzoxaphosphinine

  • EINECS
  • CAS No. 22749-43-5
  • Article Data25
  • CAS DataBase
  • Density
  • Solubility
  • Melting Point 87ºC
  • Formula C12H8 Cl O P
  • Boiling Point 374.6 °C at 760 mmHg
  • Molecular Weight 234.622
  • Flash Point 180.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 22749-43-5 (6-Chlorobenzo[c][1,2]benzoxaphosphinine)
  • Hazard Symbols
  • Synonyms 6-Chloro-6H-dibenz-[c,e][1,2]-oxaphosphorin;6-Chloro-6H-dibenz[c,e][1,2]oxaphosphorin; 6-Chlorodibenz[c,e][1,2]oxaphosphorin
  • PSA 22.82000
  • LogP 3.92200

Synthetic route

2-Phenylphen-1-oxydichlorphosphan
33771-47-0

2-Phenylphen-1-oxydichlorphosphan

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
With zinc(II) chloride at 150℃; for 2h;100%
With zinc(II) chloride at 194℃; for 1.25h;79%
With aluminium trichloride In n-heptane
With zinc(II) chloride at 250℃; for 2h;
With zinc at 180℃; for 3h; Inert atmosphere;
2-Phenylphenol
90-43-7

2-Phenylphenol

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
With zinc(II) chloride; phosphorus trichloride at 20 - 180℃; for 7h;100%
With anhydrous phosphorus trichloride; phosphorus trichloride; Zinc chloride In 5,5-dimethyl-1,3-cyclohexadiene95%
Stage #1: 2-Phenylphenol With phosphorus trichloride at 140℃; for 5h; Inert atmosphere; Neat (no solvent);
Stage #2: With zinc(II) chloride at 210℃; for 3h; Inert atmosphere; Neat (no solvent);
90%
2-Phenylphenol
90-43-7

2-Phenylphenol

diphenyl ether , 4-oxy-diphenyl

diphenyl ether , 4-oxy-diphenyl

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphorus trichloride / 5 h / 148 °C
2: 79 percent / ZnCl2 / 1.25 h / 194 °C
View Scheme
2-Phenylphenol
90-43-7

2-Phenylphenol

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
Zinc chloride In toluene
9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
35948-25-5

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
With phosphorus trichloride In chloroform for 3h; Inert atmosphere; Reflux;
With phosphorus trichloride In chloroform for 4h; Inert atmosphere; Reflux;
9,10-dihydro-9-oxa-10-phosphaphenanthrene
25072-46-2

9,10-dihydro-9-oxa-10-phosphaphenanthrene

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
With phosphorus trichloride In chloroform for 3h; Inert atmosphere; Reflux;
tris(2-phenylphenyl)phosphite
2752-19-4

tris(2-phenylphenyl)phosphite

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
With zinc(II) chloride; phosphorus trichloride at 200℃; for 4h; Temperature;35 g
2,2'-dihydroxybiphenyl
1806-29-7

2,2'-dihydroxybiphenyl

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
With phosphorus trichloride In toluene at 140℃; for 8h; Cooling with ice;
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

2,4,6-triamino-s-triazine
108-78-1

2,4,6-triamino-s-triazine

2,4,6-tris(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-ylamino)-1,3,5-triazine

2,4,6-tris(9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-ylamino)-1,3,5-triazine

Conditions
ConditionsYield
With 1-methyl-1H-imidazole at 100℃; for 16h; Inert atmosphere;100%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

C20H17O3P

C20H17O3P

6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide
1631149-46-6

6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide

Conditions
ConditionsYield
Stage #1: p-chlorodibenzo[c.e][1,2]oxaphosphorine; C20H17O3P With triethylamine at 10℃; for 2h;
Stage #2: With Methyl benzenesulfonate at 100 - 150℃; for 5h;
99.3%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

recorcinol
108-46-3

recorcinol

6,6'-(1,3-phenylenebis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide)

6,6'-(1,3-phenylenebis(oxy))bis(6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide)

Conditions
ConditionsYield
Stage #1: p-chlorodibenzo[c.e][1,2]oxaphosphorine; recorcinol In toluene at 20 - 120℃; for 6h; Heating / reflux;
Stage #2: With ammonia In toluene at 20℃; for 0.0833333h;
Stage #3: With water; ozone more than 3 stages;
98.9%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
35948-25-5

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide

Conditions
ConditionsYield
With water; hydrogenchloride at 80℃; for 1h; Product distribution / selectivity;98%
With water In toluene for 4h; Heating / reflux;95%
In ethanol
With water
With water10.1 g
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

(-)-menthol
2216-51-5

(-)-menthol

6-(1R,2S,5R)-(-)-menthyl-dibenzo[c.e][5,6]oxaphosphorine

6-(1R,2S,5R)-(-)-menthyl-dibenzo[c.e][5,6]oxaphosphorine

Conditions
ConditionsYield
With triethylamine In toluene at 26℃; for 3h;97%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

6-chloro-6H-dibenzo[c,e]-[1,2]oxaphosphinine 6-sulfide
30343-12-5

6-chloro-6H-dibenzo[c,e]-[1,2]oxaphosphinine 6-sulfide

Conditions
ConditionsYield
With sulfur at 130 - 160℃; for 5h; Inert atmosphere;95%
With sulfur
Multi-step reaction with 2 steps
1: hydrogen sulfide; sodium hydroxide / water; toluene / 20 °C
2: chloroform; triethylamine / tetrachloromethane / 0 °C
View Scheme
Multi-step reaction with 3 steps
1: water
2: tetraphosphorus decasulfide / toluene / 17 h / 40 - 55 °C / Inert atmosphere
3: chloroform; triethylamine / tetrachloromethane / 0 °C
View Scheme
With sulfur; triethylamine In toluene at 20℃; for 6h; Inert atmosphere; Reflux;
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

(S)-1-phenyl-ethylamine
2627-86-3

(S)-1-phenyl-ethylamine

6-(S)-(-)-α-methyl-benzylamino-dibenzo[c.e][5,6]oxaphosphorine

6-(S)-(-)-α-methyl-benzylamino-dibenzo[c.e][5,6]oxaphosphorine

Conditions
ConditionsYield
With triethylamine In toluene at 26℃; for 3h;95%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

chloro-trimethyl-silane
75-77-4

chloro-trimethyl-silane

2-bromoanisole
578-57-4

2-bromoanisole

2'-[di-o-anisylphosphanyl]-2-(trimethylsilyloxy)-1,1'-biphenyl
1268251-51-9

2'-[di-o-anisylphosphanyl]-2-(trimethylsilyloxy)-1,1'-biphenyl

Conditions
ConditionsYield
Stage #1: 2-bromoanisole With tert.-butyl lithium In diethyl ether; pentane at 20℃; for 2h; Inert atmosphere;
Stage #2: p-chlorodibenzo[c.e][1,2]oxaphosphorine In tetrahydrofuran; diethyl ether; pentane at -90 - 20℃; Inert atmosphere;
Stage #3: chloro-trimethyl-silane In tetrahydrofuran; diethyl ether; pentane at 20℃; for 2h; Inert atmosphere;
95%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

phenol
108-95-2

phenol

6-phenoxy-6H-dibenz<1,2>oxaphosphorin

6-phenoxy-6H-dibenz<1,2>oxaphosphorin

Conditions
ConditionsYield
With triethylamine at 210℃; for 4h;94%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

diethylamine
109-89-7

diethylamine

2-diethlylaminodibenzo[c.e][1,2]oxaphosphorine

2-diethlylaminodibenzo[c.e][1,2]oxaphosphorine

Conditions
ConditionsYield
In toluene at 26℃; for 3h;94%
In toluene at 26℃; for 3h;
In toluene at 26℃; for 4h; Inert atmosphere;
In toluene at 20℃; for 3h; Inert atmosphere;
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

1-(6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)ethan-1-aminium chloride

1-(6-oxidodibenzo[c,e][1,2]oxaphosphinin-6-yl)ethan-1-aminium chloride

6-(1-(bis(6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)amino)ethyl)dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(1-(bis(6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)amino)ethyl)dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
at 40℃; for 18h; Inert atmosphere;94%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

methanol
67-56-1

methanol

10-methoxy-10H-9-oxa-10-phosphaphenanthrene
37632-28-3

10-methoxy-10H-9-oxa-10-phosphaphenanthrene

Conditions
ConditionsYield
With triethylamine In toluene at 50℃; for 2h;92%
With pyridine In diethyl ether; benzene
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

2-methyl-but-3-yn-2-ol
115-19-5

2-methyl-but-3-yn-2-ol

6-(3-methylbuta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(3-methylbuta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃; for 8h;92%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

1-Ethynyl-1-cyclohexanol
78-27-3

1-Ethynyl-1-cyclohexanol

6-(2-cyclohexylidenevinyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(2-cyclohexylidenevinyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃;91%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

phenylmagnesium bromide

phenylmagnesium bromide

2'-hydroxy-2-diphenylphosphinobiphenyl
155566-51-1

2'-hydroxy-2-diphenylphosphinobiphenyl

Conditions
ConditionsYield
In tetrahydrofuran at 26℃; for 20h;90%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

acetophenone
98-86-2

acetophenone

6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide
1631149-46-6

6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide

Conditions
ConditionsYield
With phosphoric acid In 5,5-dimethyl-1,3-cyclohexadiene; water at 160℃; for 4.5h; Concentration; Temperature; Reagent/catalyst; Inert atmosphere;90%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-sulfide
1259405-60-1

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-sulfide

Conditions
ConditionsYield
With hydrogen sulfide; sodium hydroxide In water; toluene at 20℃;89%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

3-ethyl-1-pentyn-3-ol
6285-06-9

3-ethyl-1-pentyn-3-ol

6-(3-ethylpenta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(3-ethylpenta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃;89%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

triethylamine
121-44-8

triethylamine

triethylammonium 6H-dibenzo[c,e][1,2]oxaphosphinine-6-thiolate 6-sulfide
1259405-65-6

triethylammonium 6H-dibenzo[c,e][1,2]oxaphosphinine-6-thiolate 6-sulfide

Conditions
ConditionsYield
With sulfur In toluene at 20℃; for 8h; Inert atmosphere; Reflux;87%
1,4-dihydroxybut-2-yne
110-65-6

1,4-dihydroxybut-2-yne

p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

C28H20O4P2

C28H20O4P2

Conditions
ConditionsYield
With N-ethylmorpholine; In dichloromethane at 0 - 20℃;86%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

meparfynol
77-75-8

meparfynol

6-(3-methylpenta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(3-methylpenta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃; diastereoselective reaction;86%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

2-Phenyl-3-butyn-2-ol
127-66-2

2-Phenyl-3-butyn-2-ol

6-(3-phenylbuta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(3-phenylbuta-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃;86%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

1-ethynylcyclopentanol
17356-19-3

1-ethynylcyclopentanol

6-(2-cyclopentylidenevinyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(2-cyclopentylidenevinyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃;85%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

3,5-dimethyl-1-hexyn-3-ol
107-54-0

3,5-dimethyl-1-hexyn-3-ol

6-(3,5-dimethylhexa-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-(3,5-dimethylhexa-1,2-dien-1-yl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
With pyridine In diethyl ether at 0 - 28℃; diastereoselective reaction;84%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

C36H24N3O3P3

C36H24N3O3P3

Conditions
ConditionsYield
With trimethylsilylazide In toluene at 50℃; for 24h; Inert atmosphere;83.4%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

(2,4,6-triisopropylphenyl)magnesium bromide
108894-99-1

(2,4,6-triisopropylphenyl)magnesium bromide

10-(2,4,6-triisopropyl-phenyl)-10H-9-oxa-10-phospha-phenanthrene
843615-07-6

10-(2,4,6-triisopropyl-phenyl)-10H-9-oxa-10-phospha-phenanthrene

Conditions
ConditionsYield
In tetrahydrofuran at 26℃;82%
In tetrahydrofuran at 0 - 26℃;
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

ethylmagnesium bromide
925-90-6

ethylmagnesium bromide

(2'-hydroxy-biphenyl-2-yl)-diethylphosphane
1093348-90-3

(2'-hydroxy-biphenyl-2-yl)-diethylphosphane

Conditions
ConditionsYield
In tetrahydrofuran at 20 - 65℃; Inert atmosphere;82%
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

p-chlorodibenzo[c.e][1,2]oxaphosphorine

2-(pyridine-2-yl)propan-2-ol
37988-38-8

2-(pyridine-2-yl)propan-2-ol

2-ethyl(1'-methyl-1'-hydroxy)pyridine-6H-dibenz[c,e][1,2]oxaphosphorin
605666-57-7

2-ethyl(1'-methyl-1'-hydroxy)pyridine-6H-dibenz[c,e][1,2]oxaphosphorin

Conditions
ConditionsYield
Stage #1: 2-(pyridine-2-yl)propan-2-ol With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h;
Stage #2: p-chlorodibenzo[c.e][1,2]oxaphosphorine In tetrahydrofuran; hexane at 20℃; for 12h; Further stages.;
80%

6-Chlorobenzo[c][1,2]benzoxaphosphinine Chemical Properties

Molecular Formula: C12H8ClOP
Molecular Weight: 234.62
Flash Point: 180.3 °C
Melting Point: 87°C
CAS Registry Number: 22749-43-5
Enthalpy of Vaporization: 59.76 kJ/mol 
Vapour Pressure: 1.78E-05 mmHg at 25°C 
IUPAC Name: 6-chlorobenzo[c][1,2]benzoxaphosphinine
Boiling Point of 6-Chloro-6H-dibenzo[c,e][1,2]oxaphosphinine (CAS NO.22749-43-5): 374.6 °C at 760 mmHg 
Synonyms: 6-Chlorodibenz[c,e][1,2]oxaphosphorin (CAS NO.22749-43-5) ; 6-Chloro-6H-dibenzo[c,e][1,2]oxaphosphinine ; 6-chlorobenzo[C][1,2]benzoxaphosphinine ; 10-Chloro-9,10-Dihydro-9-oxa-10-phosphaphenanthrene ; 6-Chloro-6H-dibenz[c,e][1,2]oxaphosphorin
Following is the molecular structure of 6-Chloro-6H-dibenzo[c,e][1,2]oxaphosphinine (CAS NO.22749-43-5):

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