Product Name

  • Name

    9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide

  • EINECS 252-813-7
  • CAS No. 35948-25-5
  • Article Data10
  • CAS DataBase
  • Density
  • Solubility 3.574g/L at 25℃
  • Melting Point 119 °C
  • Formula C12H9O2P
  • Boiling Point 399.658 °C at 760 mmHg
  • Molecular Weight 216.176
  • Flash Point 206.441 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 35948-25-5 (9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide)
  • Hazard Symbols
  • Synonyms 3,4:5,6-Dibenzo-2H-1,2-oxaphosphorin-2-oxide;9,10-Dihydro-9-oxa-10-phosphaphenanthren-10-oxide;9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide;9,10-Dihydro-9-oxa-10-phosphorylphenanthrene-10-oxide;
  • PSA 49.77000
  • LogP 2.84600

Synthetic route

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
2-(2-hydroxyphenyl)-phenylphosphonous acid
35948-24-4

2-(2-hydroxyphenyl)-phenylphosphonous acid

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

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

Conditions
ConditionsYield
With toluene-4-sulfonic acid In water; toluene for 4h; Reflux;97.5%
at 160℃; under 30 Torr; for 2h; Activation energy; Cyclization;
at 160℃; under 30 Torr; for 2h; Dehydration;
at 180℃; under 3.75038 Torr; for 6h; Pressure; Temperature;
2-Phenylphen-1-oxydichlorphosphan
33771-47-0

2-Phenylphen-1-oxydichlorphosphan

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AlCl3 / heptane
2: aq. ethanol
View Scheme
p-chlorodibenzo[c.e][1,2]oxaphosphorine
22749-43-5

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

2-Phenylphenol
90-43-7

2-Phenylphenol

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

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

Conditions
ConditionsYield
In toluene
1-propylammonium (2-hydroxy-biphenyl-2-yl)-phosphinate
1208129-37-6

1-propylammonium (2-hydroxy-biphenyl-2-yl)-phosphinate

A

propylamine
107-10-8

propylamine

B

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

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

Conditions
ConditionsYield
at 165℃; under 3.75038 Torr; for 2.25h;
2-Phenylphenol
90-43-7

2-Phenylphenol

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

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

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluorormethanesulfonic acid; phosphorus trichloride / 4.5 h / 150 °C
2: water
View Scheme
Multi-step reaction with 3 steps
1.1: phosphorus trichloride; zinc(II) chloride / 4 h / 80 - 180 °C
2.1: diatomaceous earth / toluene / 0.5 h / 20 °C
2.2: 4 h / Reflux
3.1: 6 h / 180 °C / 3.75 Torr
View Scheme
9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
35948-25-5

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

6-Chloro-6H-dibenz<1,2>oxaphosphorin
32186-92-8

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

Conditions
ConditionsYield
With chlorine; sodium hydroxide In dichloromethane at 20℃; for 12.6h; Inert atmosphere; Large scale;100%
With chlorine In dichloromethane at 40℃; for 5h; Appel Halogenation;100%
With tetrachloromethane; triethylamine In chloroform at 5℃;
hexaepoxypropanoxycyclotriphosphazene

hexaepoxypropanoxycyclotriphosphazene

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

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

C90H84N3O24P9

C90H84N3O24P9

Conditions
ConditionsYield
at 160℃; for 5h; Temperature; Time;99.8%
dimethylvinylphosphonate
4645-32-3

dimethylvinylphosphonate

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

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

2-(9,10-dihydro-9-oxo-10-phosphaphenanthrene-10-oxide-10-yl)dimethyl ethylphosphonate

2-(9,10-dihydro-9-oxo-10-phosphaphenanthrene-10-oxide-10-yl)dimethyl ethylphosphonate

Conditions
ConditionsYield
at 130℃; for 8h; Inert atmosphere;99.38%
With trimethylphosphane In tetrahydrofuran at 0 - 25℃; for 20.5h; Schlenk technique;90%
N,N-bis(2-((trimethylsilyl)oxy)ethyl)acrylamide
1367371-13-8

N,N-bis(2-((trimethylsilyl)oxy)ethyl)acrylamide

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

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

3-(6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)-N,N-bis{2-[(trimethylsilyl)oxy]ethyl}propanamide
1367371-14-9

3-(6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)-N,N-bis{2-[(trimethylsilyl)oxy]ethyl}propanamide

Conditions
ConditionsYield
With triethylamine In toluene Michael addition; Inert atmosphere; Reflux;99%
2,2-bis(3-allyl-4-hydroxyphenyl)propane
1745-89-7

2,2-bis(3-allyl-4-hydroxyphenyl)propane

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

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

DDBA

DDBA

Conditions
ConditionsYield
With 2,2'-azobis(isobutyronitrile) In propan-1-ol at 75℃; for 24h; Temperature; Solvent;98.8%
formaldehyd
50-00-0

formaldehyd

diethylamine
109-89-7

diethylamine

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

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

C17H22NO3P
1133910-18-5

C17H22NO3P

Conditions
ConditionsYield
In ethanol at 80℃; for 1.5h; Mannich condensation;98%
salicylaldehyde
90-02-8

salicylaldehyde

4-amino-benzoic acid
150-13-0

4-amino-benzoic acid

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

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

C26H20NO5P
1160307-73-2

C26H20NO5P

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 12h;98%
formaldehyd
50-00-0

formaldehyd

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

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

2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)methanol
35948-26-6

2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)methanol

Conditions
ConditionsYield
In benzene at 70℃; for 12h; Solvent; Temperature; Inert atmosphere;98%
With sulfuric acid In diethylene glycol dimethyl ether at 50 - 120℃; for 6.5h; Temperature; Reagent/catalyst; Solvent; Inert atmosphere;97%
at 100℃; for 4h;
phenylacetylene
536-74-3

phenylacetylene

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

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

E-10-(styr-2-yl)-9,10-dihydro-9-oxa-10-phosphaphenantrene-10-oxide
1586744-35-5

E-10-(styr-2-yl)-9,10-dihydro-9-oxa-10-phosphaphenantrene-10-oxide

Conditions
ConditionsYield
Stage #1: 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide With copper acetylacetonate In tetrahydrofuran; N,N-dimethyl-formamide Inert atmosphere;
Stage #2: phenylacetylene In tetrahydrofuran; N,N-dimethyl-formamide at 70℃; for 16h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; diastereoselective reaction;
98%
C42H43N6O16P

C42H43N6O16P

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

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

C90H79N6O24P5

C90H79N6O24P5

Conditions
ConditionsYield
at 160℃; for 3h;98%
1-p-toluenesulfonyl-4-ethynyl-1,4-dihydro-2H-benzo[d][1,3]-azahexan-2-one

1-p-toluenesulfonyl-4-ethynyl-1,4-dihydro-2H-benzo[d][1,3]-azahexan-2-one

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

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

6-((1-tosyl-1H-indol-2-yl)methyl)dibenzo[c,e][1,2]oxaphosphinine 6-oxide

6-((1-tosyl-1H-indol-2-yl)methyl)dibenzo[c,e][1,2]oxaphosphinine 6-oxide

Conditions
ConditionsYield
Stage #1: 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide With copper(l) iodide; N-ethyl-N,N-diisopropylamine; 2,6-bis(4,5-dihydrooxazol-2-yl)pyridine In 1,2-dichloro-ethane at 20℃; for 0.166667h; Inert atmosphere; Schlenk technique;
Stage #2: 1-p-toluenesulfonyl-4-ethynyl-1,4-dihydro-2H-benzo[d][1,3]-azahexan-2-one In 1,2-dichloro-ethane at 20℃; for 1h; Inert atmosphere; Schlenk technique;
98%
acrylonitrile
107-13-1

acrylonitrile

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

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

6H-dibenz[c,e][1,2]oxaphosphorin-6-propanenitrile 6-oxide

6H-dibenz[c,e][1,2]oxaphosphorin-6-propanenitrile 6-oxide

Conditions
ConditionsYield
97%
at 130℃; for 1h; microwave irradiation;89%
2-Isocyanatoethyl methacrylate
30674-80-7

2-Isocyanatoethyl methacrylate

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

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

C19H18NO5P

C19H18NO5P

Conditions
ConditionsYield
With triethylamine In dichloromethane at 30℃; for 10h;97%

6H-Dibenz[c,e][1,2]oxaphosphorin 6-oxide Chemical Properties


IUPAC Name: Benzo[c][1,2]benzoxaphosphinin-6-ium 6-oxide
Molecular Formula: C12H9O2P
Molecular Weight: 216.17 g/mol
Canonical SMILES: c12c3c([P@@](=O)Oc1cccc2)cccc3
InChI: InChI=1/C12H9O2P/c13-15-12-8-4-2-6-10(12)9-5-1-3-7-11(9)14-15/h1-8,15H
EINECS: 252-813-7
Product Categories: Industrial/Fine Chemicals
Flash Point: 206.441 °C
Enthalpy of Vaporization: 62.506 kJ/mol
Boiling Point: 399.658 °C at 760 mmHg
Melting Point: 119 °C
Vapour Pressure of 6H-Dibenz[c,e][1,2]oxaphosphorin 6-oxide (CAS NO.35948-25-5): 0 mmHg at 25 °C

6H-Dibenz[c,e][1,2]oxaphosphorin 6-oxide Safety Profile

Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements of 6H-Dibenz[c,e][1,2]oxaphosphorin 6-oxide (CAS NO.35948-25-5): 26-36/37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.

6H-Dibenz[c,e][1,2]oxaphosphorin 6-oxide Specification

  6H-Dibenz[c,e][1,2]oxaphosphorin 6-oxide (CAS NO.35948-25-5), its Synonyms are 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide ; 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide ; 3,4:5,6-dibenzo-1,2-oxaphosphane-2-oxide ; 9,10-dihydro-9-oxa-10-phospaphenanthrene- .

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