35948-25-5

Basic information

• Product Name: 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide
• Synonyms: DOP;10H-9-Oxa-10-phosphaphenanthrene 10-oxide;9H,10H-9-Oxa-10-phosphaphenanthrene-10-oxide;9-Oxa-10-phospha-9,10-dihydrophenanthrene 10-oxide;PD-3710;9,10-Dihydro-9-oxa-10-phosphapheanthrene-10-Oxid;C6H4P(O)(H)OC6H4;10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide
• CAS NO: 35948-25-5
• Molecular Formula: C₁₂H₉O₂P
• Molecular Weight: 216.17
• EINECS: 252-813-7
• Product Categories: fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis;fine chemicals, specialty chemicals, intermediates, electronic chemical, organic synthesis, functional materials;flame retardant;Piperazines ,Oxazolines/Oxazolidines;Industrial/Fine Chemicals
• Mol File: 35948-25-5.mol
• Article Data: 9

Chemical Properties

• Melting Point: 119°C
• Boiling Point: 399.658 °C at 760 mmHg
• Flash Point: 206.441 °C
• Appearance: /
• Vapor Pressure: 0mmHg at 25°C
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility: 3.574g/L at 25℃
• CAS DataBase Reference: 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide(35948-25-5)
• EPA Substance Registry System: 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-oxide(35948-25-5)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 35948-25-5(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 35948-25-5 differently. You can refer to the following data:
1. 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide
2. 9,10-Dihydro-9-oxa-10-phosphaphenanthrene 10-Oxide is an high effective componant of flame retardant epoxy resins.

Flammability and Explosibility

Nonflammable

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

Synthetic route

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
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 water	10.1 g

2-(2-hydroxyphenyl)-phenylphosphonous acid (35948-24-4) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
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) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: AlCl3 / heptane 2: aq. ethanol View Scheme

p-chlorodibenzo[c.e][1,2]oxaphosphorine (22749-43-5) + 2-Phenylphenol (90-43-7) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
In toluene

1-propylammonium (2-hydroxy-biphenyl-2-yl)-phosphinate (1208129-37-6) → propylamine (107-10-8) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
at 165℃; under 3.75038 Torr; for 2.25h;

2-Phenylphenol (90-43-7) → 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5)

Conditions	Yield
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) → 6-Chloro-6H-dibenz<1,2>oxaphosphorin (32186-92-8)

Conditions	Yield
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 + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C90H84N3O24P9

Conditions	Yield
at 160℃; for 5h; Temperature; Time;	99.8%

dimethylvinylphosphonate (4645-32-3) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 2-(9,10-dihydro-9-oxo-10-phosphaphenanthrene-10-oxide-10-yl)dimethyl ethylphosphonate

Conditions	Yield
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) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 3-(6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)-N,N-bis{2-[(trimethylsilyl)oxy]ethyl}propanamide (1367371-14-9)

Conditions	Yield
With triethylamine In toluene Michael addition; Inert atmosphere; Reflux;	99%

2,2-bis(3-allyl-4-hydroxyphenyl)propane (1745-89-7) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → DDBA

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

formaldehyd (50-00-0) + diethylamine (109-89-7) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C17H22NO3P (1133910-18-5)

Conditions	Yield
In ethanol at 80℃; for 1.5h; Mannich condensation;	98%

salicylaldehyde (90-02-8) + 4-amino-benzoic acid (150-13-0) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C26H20NO5P (1160307-73-2)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 12h;	98%

formaldehyd (50-00-0) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)methanol (35948-26-6)

Conditions	Yield
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) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → E-10-(styr-2-yl)-9,10-dihydro-9-oxa-10-phosphaphenantrene-10-oxide (1586744-35-5)

Conditions	Yield
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 + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C90H79N6O24P5

Conditions	Yield
at 160℃; for 3h;	98%

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

Conditions	Yield
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) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 6H-dibenz[c,e][1,2]oxaphosphorin-6-propanenitrile 6-oxide

Conditions	Yield
	97%
at 130℃; for 1h; microwave irradiation;	89%

2-Isocyanatoethyl methacrylate (30674-80-7) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → C19H18NO5P

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

Upstream product

• 90-43-7 2-Phenylphenol 
• 1208129-37-6 1-propylammonium (2-hydroxy-biphenyl-2-yl)-phosphinate 
• 22749-43-5 p-chlorodibenzo[c.e][1,2]oxaphosphorine 
• 35948-24-4 2-(2-hydroxyphenyl)-phenylphosphonous acid 
• 33771-47-0 2-Phenylphen-1-oxydichlorphosphan 

Downstream Products

• 1205686-60-7 C₃₁H₂₃O₄P 
• 1205686-58-3 1,1-bis(4-hydroxyphenyl)-1-(6-oxido-6H-dibenz[c,e][1,2]oxaphosphorin-6-yl)ethane 
• 1253521-98-0 C₅₀H₃₈N₂O₇P₂ 
• 63562-42-5 6H-dibenz[c,e][1,2]oxaphosphorin-6-propanoic acid methyl ester 6-oxide 
• 130444-44-9 6-<1-Hydroxy-1-(p-hydroxyphenyl)methyl>-6H-dibenz<1,2>oxaphosphorin 6-oxide 
• 130444-41-6 (10-Oxo-10H-9-oxa-10λ⁵-phospha-phenanthren-10-yl)-phenyl-methanol 
• 1631149-46-6 6H-dibenz[c,e][1,2]oxaphosphorin,6'6-(1,2-phenethyl)bis-,6'6-dioxide 

Relevant articles and documents

Thermogravimetric analysis study of a cyclic organo-phosphorus compound

Four methods were used to study the thermal cyclisation of 2-(2-hydroxyphenyl)-phenylphosphonous acid 3, and the results were compared with the thermal decomposition of 9,10-Dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO). The decomposition of DOPO was found to be a simple process composed of at least one stage for which apparent activation energies can be calculated. These investigated methods were those of van Krevelen, Horowitz-Metzger, Coats-Redfern, and MacCallum-Tanner. These methodologies evaluated the similar apparent activation energies Ea for cyclisation of 3 and for decomposition of DOPO. Moreover, these apparent activation energies for decomposition of DOPO were compared with that calculated by the isothermal method.

Method for synthesizing 9, 10-dihydro-9-oxygen-10-phosphaphenanthrene-10-oxide

The invention discloses a method for synthesizing 9, 10-dihydro-9-oxygen-10-phosphaphenanthrene-10-oxide. The method includes adding phosphorus trichloride into excessive o-phenylphenol drop by drop and carrying out esterification reaction to obtain phosphorous acid tri-orthophthalic phenyl ester; adding ZnCl2 catalysts into the phosphorous acid tri-orthophthalic phenyl ester, adding phosphorus trichloride into the phosphorous acid tri-orthophthalic phenyl ester drop by drop and carrying out acylation reaction to obtain 6-chlorine-(6 hydrogen)-dibenzo-(c, e)-oxygen phosphorus heterocyclic hexa-rings; sequentially carrying out hydrolysis reaction and cyclization reaction on the 6-chlorine-(6 hydrogen)-dibenzo-(c, e)-oxygen phosphorus heterocyclic hexa-rings to obtain the 9, 10-dihydro-9-oxygen-10-phosphaphenanthrene-10-oxide. The method has the advantages that the o-phenylphenol can be prevented from being volatilized or oxidized at high temperatures, the method is high in reaction speed and suitable for industrial production, and target products are high in yield and purity.

METHOD FOR SYNTHESIZING 9,10-DIHYDRO-9-OXA-10-PHOSPHAPHENANTHRENE-10-OXIDE AND DERIVATIVES THEREOF

A method for synthesizing 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide or its derivatives has a step of introducing 6-chloro-6H-dibenz[c,e][1,2]oxaphosphorin or its derivative, an acid compound and water into a reacting chamber to form an organic layer having 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide or its derivative and an aqueous layer. Because the acid compound is from an external source and has a catalyzing effect, employing the method can prevent side reaction from occurring and increase yield of 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide or its derivative. Furthermore, the method is a one-pot operation of hydrolysis, dehydration and cyclization, so the method does not require purification of intermediates. Therefore, the method is time-and cost-saving and requires less organic solvent, resulting in less pollution to the environment.