99208-50-1

Basic information

• Product Name: 10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phospha-phenantbrene-10-oxide
• Synonyms: 10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phosphaphenantbrene-10-oxide;9,10-dihydroxy-9-oxa-10-[2,3-di(2-hydroxyethoxycarbonyl)propyl]-phosphaphenanthrene-10-oxide;10-(2,5-Dihydroxyphenyl)-10H-9-0xa-10-Phospha-phenanthrene-10-Oxide;2-(10H-9-Oxa-10-phospha-1-phenanthryl)hydroquinone phosphorus oxide;HCA-HQ;ODOPB;10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phosphaphenanthrene 10-oxide;10-(2,5-Dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide
• CAS NO: 99208-50-1
• Molecular Formula: C₁₈H₁₃O₄P
• Molecular Weight: 324.27
• EINECS: 1592732-453-0
• Product Categories: Industrial/Fine Chemicals
• Mol File: 99208-50-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 245-255 °C
• Boiling Point: 592.882 °C at 760 mmHg
• Flash Point: 312.364 °C
• Appearance: /
• Density: 1.498 g/cm³
• Storage Temp.: 2-8°C
• PKA: 9.29±0.48(Predicted)
• Water Solubility: 1.15mg/L at 20℃
• CAS DataBase Reference: 10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phospha-phenantbrene-10-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phospha-phenantbrene-10-oxide(99208-50-1)
• EPA Substance Registry System: 10-(2,5-Dihydroxyphenyl)-10H-9-oxa-10-phospha-phenantbrene-10-oxide(99208-50-1)

Safety Data

• Hazardous Substances Data: 99208-50-1(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

Synthetic route

p-benzoquinone (106-51-4) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1)

Conditions	Yield
In 2-ethoxy-ethanol at 125℃; for 4h; Inert atmosphere;	93%
In toluene at 110℃; for 3.5h; Temperature; Inert atmosphere;	92%
In toluene at 120℃; for 5h; Inert atmosphere;	91.2%

2,5-dihydroxy-1-iodobenzene (23030-43-5) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium acetate In 1,4-dioxane at 100℃; for 12h; Inert atmosphere;	65%

2-bromobenzene-1,4-diol (583-69-7) + 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (35948-25-5) → 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium acetate In 1,4-dioxane at 100℃; for 24h; Inert atmosphere;	25%

Diisopropyl chlorophosphate (2574-25-6) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)-1,4-benzenedi(diisopropyl phosphate)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Reflux;	93%

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) + dibutyl chlorophosphate (819-43-2) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)-1,4-benzenedi(di(n-butyl) phosphate)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Reflux;	89.2%

diethyl chlorophosphate (814-49-3) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)-1,4-benzenedi(diethyl phosphate)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Reflux;	82.6%

dipropyl chlorophosphate (2510-89-6) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)-1,4-benzenedi(di(n-propyl) phosphate)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Reflux;	80.5%

Dimethyl chlorophosphate (813-77-4) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)-1,4-benzenedi(dimethyl phosphate)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Reflux;	78%

di(sec-butyl) phosphoryl chloride (54757-38-9) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 2-(6-oxido-6H-dibenz(c,e)(1,2)oxaphosphorin-6-yl)-1,4-benzenedi(di(sec-butyl) phosphate)

Conditions	Yield
With potassium carbonate In acetonitrile at 20℃; for 8h; Reflux;	76.2%

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) + cyanogen chloride (506-77-4) → C20H11N2O4P (1018986-69-0)

Conditions	Yield
With triethylamine In acetone at -9 - -6℃; for 2.75h;	75%

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 2-(6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinine-6-yl)cyclohexa-2,5-diene-1,4-dione (1384457-22-0)

Conditions	Yield
With manganese(IV) oxide In acetone at 20℃; for 1h;	68.8%

4-Fluoronitrobenzene (350-46-9) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → C30H19N2O8P

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 160℃; for 12h; Inert atmosphere;	67%
With cesium fluoride In N,N-dimethyl acetamide at 160℃; for 10h;	55.55%

4-Vinylbenzyl chloride (1592-20-7) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → C36H29O4P

Conditions	Yield
Stage #1: 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide With sodium hydroxide In toluene at 70℃; for 0.5h; Stage #2: 4-Vinylbenzyl chloride With tetrabutylammomium bromide In toluene at 70℃; for 10h;	65%
Stage #1: 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide With sodium hydroxide In toluene at 70℃; for 0.5h; Stage #2: 4-Vinylbenzyl chloride With tetrabutylammomium bromide In toluene for 10h;	65%

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) + 4-[4-(2-methylbutoxy)phenyl] benzoic acid → C54H49O8P

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran	58%

4'-octyloxy(1,1'-biphenyl)-4-carboxylic acid (59748-18-4) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → C60H61O8P

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran for 6h;	28%

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) + 4-{4-[2-(2-methoxyethoxy)ethoxy]phenyl} benzoic acid (823222-06-6) → C54H49O12P

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran	27%

epichlorohydrin (106-89-8) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 9,10-dihydro-10-(2',5'-diglycidyloxyphenyl)-9-oxa-10-phosphaphenanthrene-10-oxide

Conditions	Yield
With sodium methylate Etherification;
With N-benzyl-N,N,N-triethylammonium chloride at 95℃; for 4h; Reagent/catalyst; Temperature; Inert atmosphere;

4'-n-hexyloxybiphenyl-4-carboxylic acid (59748-16-2) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → C56H53O8P

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In tetrahydrofuran

Reaxys ID: 11458169 + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → Reaxys ID: 13061976

formaldehyd (50-00-0) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) + 3,4-difluoroaniline (3863-11-4) → C34H23F4N2O4P (1151509-52-2)

Conditions	Yield
at 90℃;

formaldehyd (50-00-0) + Reaxys ID: 19448680 + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → Reaxys ID: 19448679

Conditions	Yield
Heating;

4-Fluoronitrobenzene (350-46-9) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → C30H19N2O8P + 1,4'-bis(4-nitrophenoxy)benzene (20638-32-8) + C30H20N2O9P(1-)*K(1+)

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 160℃; for 12h; Inert atmosphere;

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 6-(2-(diphenylphosphoryl)-3,6-dihydroxyphenyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide (1384457-24-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: manganese(IV) oxide / acetone / 1 h / 20 °C 2: toluene / 3 h / Inert atmosphere; Reflux View Scheme

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 6-(2-(5,5-dimethyl-2-oxido-1,3,2-dioxaphosphinan-2-yl)-3,6-dihydroxyphenyl)-6H-dibenzo[c,e][1,2]oxaphosphinine 6-oxide (1384457-25-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: manganese(IV) oxide / acetone / 1 h / 20 °C 2: toluene / 3 h / Inert atmosphere; Reflux View Scheme

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 6-(4-hydroxy-3-(6-oxido-6H-dibenzo[c,e][1,2]-oxaphosphinine-6-yl)phenoxy)-6H-dibenzo[c,e][1,2]-oxaphosphinine 6-oxide (1384457-27-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: manganese(IV) oxide / acetone / 1 h / 20 °C 2: toluene / 3 h / Inert atmosphere; Reflux 3: triethylamine / toluene / 120 h / Reflux View Scheme

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 6,6'-(3,6-dihydroxy-1,2-phenylene)bis(6H-dibenzo[c,e][1,2]oxaphosphinine-6-oxide)

Conditions	Yield
Multi-step reaction with 2 steps 1: manganese(IV) oxide / acetone / 1 h / 20 °C 2: toluene / 3 h / Inert atmosphere; Reflux View Scheme

10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → diphenyl (3,6-dihydroxy-2-(6-oxido-6H-dibenzo[c,e][1,2]oxaphosphinin-6-yl)phenyl)phosphonate

Conditions	Yield
Multi-step reaction with 2 steps 1: manganese(IV) oxide / acetone / 1 h / 20 °C 2: toluene / 3 h / Inert atmosphere; Reflux View Scheme

teroxirone (2451-62-9) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → C42H43N6O16P

Conditions	Yield
at 150℃; for 5h;

Allyl ether (557-40-4) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → 9,10-dihydro-10-(2',5'-diglycidyloxyphenyl)-9-oxa-10-phosphaphenanthrene-10-oxide

Conditions	Yield
With magnesium sulfate; 3-chloro-benzenecarboperoxoic acid In chloroform at 25℃; for 8h; Inert atmosphere;

α-Naphthol Orange (523-44-4) + 1,4-bis[4-(carbonochloridoyl)phenyl] benzene-1,4-dicarboxylate (82684-68-2) + 10‑(2,5‑dihydroxyphenyl)‑10H-9‑oxa‑10‑phosphaphenanthrene‑10‑oxide (99208-50-1) → Reaxys ID: 30918465

Upstream product

• 23030-43-5 2,5-dihydroxy-1-iodobenzene 
• 35948-25-5 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide 
• 583-69-7 2-bromobenzene-1,4-diol 
• 106-51-4 p-benzoquinone 

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