63562-33-4

Basic information

• Product Name: 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide
• Synonyms: 2-[[(6H-Dibenzo[c,e][1,2]oxaphosphorin 6-oxide)-6-yl]methyl]butanedioic acid;6-(2,3-Dicarboxypropyl)-6H-dibenz[c,e][1,2]oxaphosphorin 6-oxide;6-(2,3-Dicarboxypropyl)6H-dibenzo[c,e][1,2]oxaphosphorin 6-oxide;9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide;[(6-Oxido-6H-dibenz[c,e][1,2]oxaphosphorin-6-yl)methyl]butanedioic acid;DDP;(6H-Dibenz[c,e][1,2]oxaphosphorin-6-ylmethyl)-p-oxide-butanedioic acid;(2-[(6-oxobenzo[c][2,1]benzoxaphosphinin-6-yl)methyl]butanedioic acid)
• CAS NO: 63562-33-4
• Molecular Formula: C₁₇H₁₅O₆P
• Molecular Weight: 346.27
• EINECS: 1592732-453-0
• Mol File: 63562-33-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 191-192 °C
• Boiling Point: 578.3 °C at 760 mmHg
• Flash Point: 303.5 °C
• Appearance: Solid
• Density: 1.48 g/cm³
• Vapor Pressure: 3.26E-14mmHg at 25°C
• Refractive Index: 1.641
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 4.13±0.23(Predicted)
• CAS DataBase Reference: 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide(63562-33-4)
• EPA Substance Registry System: 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide(63562-33-4)

Safety Data

• Hazardous Substances Data: 63562-33-4(Hazardous Substances Data)

Usage

General Description

9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide is a chemical compound that contains a phosphorus atom and is classified as an organophosphorus compound. It is used in various industrial applications as a flame retardant and as a component in the production of plastics and polymers. 9,10-Dihydro-10-(2,3-dicarboxypropyl)-9-oxa-10-phosphaphenanthrene 10-oxide is known for its stable and heat-resistant properties, making it a suitable additive for flame-retardant materials. Additionally, it is also used in the production of pharmaceuticals and agrochemicals. However, it is important to note that this compound must be handled and used with caution due to its potential toxicity and environmental impact.

InChI:InChI=1/C17H15O6P/c18-16(19)9-11(17(20)21)10-24(22)15-8-4-2-6-13(15)12-5-1-3-7-14(12)23-24/h1-8,11H,9-10H2,(H,18,19)(H,20,21)

Synthetic route

2-methylenesuccinic acid (97-65-4) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → DDP (63562-33-4)

Conditions	Yield
In 1,3-dioxane at 178℃; for 4h; Solvent; Temperature; Inert atmosphere; Sealed tube;	95%
With dihydrogen hexachloroplatinate In 5,5-dimethyl-1,3-cyclohexadiene; isopropyl alcohol at 120℃; for 20h;	311g

9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (765854-43-1) + 2-methylenesuccinic acid (97-65-4) → DDP (63562-33-4)

Conditions	Yield
With dihydrogen hexachloroplatinate In isopropyl alcohol; toluene at 120℃; for 12h;

DDP (63562-33-4) + allyl bromide (106-95-6) → C23H23O6P (1529772-14-2)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide; acetone for 12h; Reflux;	82.4%
With triethylamine In butanone at 20℃; for 18h;

DDP (63562-33-4) + 1,2-Epoxy-3-bromopropane (3132-64-7) → C23H23O8P (1529772-12-0)

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetone at 25℃; for 3h;	79.3%

DDP (63562-33-4) + 3-chloroprop-1-ene (107-05-1) → C23H23O6P (1529772-14-2)

Conditions	Yield
With potassium carbonate In tetrahydrofuran at 40℃; for 72h;

DDP (63562-33-4) → C23H23O8P (1529772-12-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: potassium carbonate / tetrahydrofuran / 72 h / 40 °C 2: dihydrogen peroxide; formic acid / 1,4-dioxane / 60 h / 60 °C View Scheme
Multi-step reaction with 2 steps 1: triethylamine / butanone / 18 h / 20 °C 2: dihydrogen peroxide; formic acid / 1,4-dioxane / 60 h / 60 °C View Scheme

Pentaerythritol (115-77-5) + DDP (63562-33-4) + C7H15NO3S → C101H116N4O32P4S4

Conditions	Yield
Stage #1: Pentaerythritol; DDP at 188℃; for 1h; Inert atmosphere; Stage #2: C7H15NO3S for 2h; Temperature; Inert atmosphere;

Pentaerythritol (115-77-5) + DDP (63562-33-4) + L-cysteine-(2-hydroxyethyl)ester → C93H100N4O32P4S4

Conditions	Yield
Stage #1: Pentaerythritol; DDP at 180℃; for 1h; Inert atmosphere; Stage #2: L-cysteine-(2-hydroxyethyl)ester for 1h; Temperature; Inert atmosphere;

Pentaerythritol (115-77-5) + DDP (63562-33-4) → C73H64O24P4

Conditions	Yield
at 180℃; for 1h; Temperature; Inert atmosphere;

DDP (63562-33-4) + C73H64O24P4 + ethylene glycol (107-21-1) → C149H132O48P8

Conditions	Yield
Stage #1: DDP; ethylene glycol With toluene-4-sulfonic acid at 186℃; for 2h; Inert atmosphere; Stage #2: C73H64O24P4 for 4h; Inert atmosphere;

Upstream product

• 765854-43-1 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 
• 97-65-4 2-methylenesuccinic acid 
• 35948-25-5 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 

Relevant articles and documents

Synthesis and properties of phosphorus-containing bio-based epoxy resin from itaconic acid

A phosphorus-containing bio-based epoxy resin (EADI) was synthesized from itaconic acid (IA) and 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide (DOPO). As a matrix, its cured epoxy network with methyl hexahydrophthalic anhydride (MHHPA) as the curing agent showed comparable glass-transition temperature and mechanical properties to diglycidyl ether in a bisphenol A (DGEBA) system as well as good flame retardancy with UL94 V-0 grade during a vertical burning test. As a reactive flame retardant, its flame-resistant effect on DGEBA/MHHPA system as well as its influence on the curing behavior and the thermal and mechanical properties of the modified epoxy resin were investigated. Results showed that after the introduction of EADI, not only were the flame retardancy determined by vertical burning test, LOI measurement, and thermogravimetric analysis significantly improved, but also the curing reactivity, glass transition temperature (T g), initial degradation temperature for 5% weight loss (T d(5%)), and flexural modulus of the cured system improved as well. EADI has great potential to be used as a green flame retardant in epoxy resin systems.

A phosphorus-containing bio-based acid diene diethyl and its preparation method and application

The invention discloses a diallyl phosphorus-containing bio-based diacid ester and its preparation method and use. The diallyl phosphorus-containing bio-based diacid ester has a structure shown in the formula I, and in the formula I, n is equal to 0 or 1. The diallyl phosphorus-containing bio-based diacid ester can be used as a fire retardant and can be used for preparation of a nonsaturated polyester. The invention also discloses a preparation method of the diallyl phosphorus-containing bio-based diacid ester. The preparation method utilizes itaconic acid, fumaric acid or maleic acid having abundant biological sources as a raw material to realize modification of DOPO. The preparation method has dual effects of saving resources and protecting environment. The invention also discloses a use of a diglycidyl phosphorus-containing bio-based diacid ester. Based on a diglycidyl phosphorus-containing bio-based diacid ester, through introduction of an epoxy group, the diglycidyl phosphorus-containing bio-based diacid ester is obtained and has a structure shown in the formula III, and in the formula III, n is equal to 0 or 1. The diglycidyl phosphorus-containing bio-based diacid ester can be used as a fire retardant and can be used for preparation of epoxy resin.