14657-64-8

Basic information

• Product Name: 3-Hydroxyphenylphosphinyl-propanoic acid
• Synonyms: 3-hydroxyphenylphosphinyl-propanoic acid;2-CARBOXYETHYL(PHENYL)PHOSPHINIC ACID;ceppa;3-HPP;3-Hydroxyphenylphosphinyl-Prop;3-hydroxy phenyl phosphinyl propanoic acid(CEPPA);3-(Hydroxyphenylphosphinyl)propionsure;2-carboxyl ethyl(phenyl)phosphinic Acid(CEPPA)
• CAS NO: 14657-64-8
• Molecular Formula: C9H11O4P
• Molecular Weight: 214.15
• EINECS: 411-200-6
• Product Categories: Flame retardant
• Mol File: 14657-64-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 158.0 to 162.0 °C
• Boiling Point: 526.605 °C at 760 mmHg
• Flash Point: 272.281 °C
• Appearance: white powder
• Density: 1.358 g/cm³
• Vapor Pressure: 6.43E-12mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: 2-8°C
• Solubility: soluble in Methanol
• PKA: 2.21±0.50(Predicted)
• Water Solubility: 31.183g/L at 20℃
• CAS DataBase Reference: 3-Hydroxyphenylphosphinyl-propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxyphenylphosphinyl-propanoic acid(14657-64-8)
• EPA Substance Registry System: 3-Hydroxyphenylphosphinyl-propanoic acid(14657-64-8)

Safety Data

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39
• Hazardous Substances Data: 14657-64-8(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C9H11O4P/c10-9(11)6-7-14(12,13)8-4-2-1-3-5-8/h1-5H,6-7H2,(H,10,11)(H,12,13)

Synthetic route

Dichlorophenylphosphine (644-97-3) + acrylic acid (79-10-7) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
Stage #1: Dichlorophenylphosphine; acrylic acid at 80 - 110℃; for 3h; Stage #2: With water at 90℃; for 3h; Temperature; Concentration;	98%
With acetic anhydride	96.8%
	94.2%

butyl 3-[butoxy(phenyl)phosphinyl]propionate (14576-56-8) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
With sulfuric acid In water	97.2%

3-(chlorophenylphosphinyl)-propionyl chloride (2071-68-3) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
With water In acetone for 0.5h; Heating;	92.6%
With water

(2-cyano-ethyl)-phenyl-phosphinic acid butyl ester (857470-46-3) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
With hydrogenchloride

3-(butoxy-phenyl-phosphinoyl)-propionic acid methyl ester (202477-16-5) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
With hydrogenchloride

Dichlorophenylphosphine (644-97-3) + μ.μ-bis-diphenylacetylene-bis-Fe-Fe) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 95.6 percent / 1.) -10 deg C, 2 h, 2.) 0 deg C, 1 h 2: 92.6 percent / water / acetone / 0.5 h / Heating View Scheme

butyl phenylphosphinate (6172-81-2) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium 2: aqueous HCl View Scheme
Multi-step reaction with 2 steps 1: sodium 2: aqueous HCl View Scheme
Multi-step reaction with 2 steps 1: sodium; benzene 2: aqueous HCl View Scheme

Dichlorophenylphosphine (644-97-3) → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

Conditions	Yield
Multi-step reaction with 3 steps 2: sodium 3: aqueous HCl View Scheme
Multi-step reaction with 3 steps 2: sodium 3: aqueous HCl View Scheme
Multi-step reaction with 3 steps 2: sodium; benzene 3: aqueous HCl View Scheme
Multi-step reaction with 2 steps 2: H2O View Scheme

hydroxyethyl 3-[hydroxy(phenyl)phosphinyl]propionate → 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8)

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + oxiranyl-methanol (556-52-5) → C15H23O8P

Conditions	Yield
In ethanol at 50℃; for 8.5h;	98%

1,6-Hexanediamine (124-09-4) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → (3-((6-aminohexyl)amino)-3-oxopropyl)(phenyl)phosphinic acid

Conditions	Yield
In ethanol at 0 - 70℃; for 4h;	96.78%

2,4,6-triamino-s-triazine (108-78-1) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → C12H15N6O3P

Conditions	Yield
In water at 20 - 70℃;	93%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → ethyl(phenyl)phosphinic acid (13317-44-7)

Conditions	Yield
With sodium hydroxide In water at 50℃; for 40h; pH=3 - 4; Temperature; pH-value; Concentration;	92.8%

aqueous cadmium chloride + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) → 2C9H9O4P(2-)*2HO(1-)*3Cd(2+)

Conditions	Yield
With triethylamine at 160℃; for 72h; pH=5; Autoclave; High pressure;	87%

manganese(II) sulfate + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → 2C9H10O4P(1-)*Mn(2+)

Conditions	Yield
In water at 120℃; for 48h; Autoclave; High pressure;	82%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + lead(II) chloride → [Pb(2-carboxyethyl(phenyl)phosphinate)2]

Conditions	Yield
In water High Pressure; mixt. PbCl2 and 2-carboxyethyl(phenyl)phosphinic acid in water in Parr Teflon-lined autoclave was heated at 150°C for 3 days; elem. anal.;	81%

1,10-Phenanthroline (66-71-7) + cadmium(II) nitrate tetrhydrate + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → C9H9O4P(2-)*Cd(2+)*C12H8N2 (1428102-03-7)

Conditions	Yield
With urea In water at 150℃; for 72h; pH=7; Autoclave;	81%

1,10-Phenanthroline (66-71-7) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) + copper(II) acetate monohydrate (6046-93-1) → C9H9O4P(2-)*Cu(2+)*4H2O*C12H8N2

Conditions	Yield
at 80 - 90℃; pH=4;	78%

1,10-Phenanthroline (66-71-7) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) + cadmium(II) acetate dihydrate (5743-04-4) → 3C9H9O4P(2-)*3Cd(2+)*3C12H8N2*6.5H2O

Conditions	Yield
at 80 - 90℃; pH=5;	72%

2,4,6-triamino-s-triazine (108-78-1) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → melaminium (2-carboxyethyl)(phenyl)phosphinate monohydrate

Conditions	Yield
With water at 20℃; Heating;	70%

1,10-Phenanthroline (66-71-7) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) + manganese (II) acetate tetrahydrate (6156-78-1) → C9H9O4P(2-)*Mn(2+)*H2O*C12H8N2 (1428102-00-4)

Conditions	Yield
With urea at 110℃; for 72h; pH=6; Autoclave;	70%

1,1'-(1,4-butanediyl)bis(imidazole) (69506-86-1) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + zinc(II) acetate dihydrate (5970-45-6) → [Zn(1,4-bis(1H-imidazol-1-yl)butane)0.5(2-carboxyethyl(phenyl)phosphinate)]n

Conditions	Yield
Stage #1: 1,1'-(1,4-butanediyl)bis(imidazole); 3-[hydroxy(phenyl)phosphinyl]propionic acid; zinc(II) acetate dihydrate With air In water at 20℃; for 0.5h; Stage #2: In water at 150℃; for 96h; Concentration; High pressure;	70%

aqueous cadmium chloride + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → 2C9H9O4P(2-)*2H(1+)*Cd(2+)

Conditions	Yield
In water at 160℃; for 72h; Autoclave; High pressure;	68%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → {NaH(Ph-PO2-C2H4-COOH)2}∞

Conditions	Yield
With sodium hydroxide In water at 20℃; for 0.166667h;	66%

4,4'-bipyridine (553-26-4) + zinc(II) nitrate hexahydrate + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → 0.5C10H8N2*C9H9O4P(2-)*Zn(2+)

Conditions	Yield
With sodium hydroxide In ethanol; water at 140℃; for 48h; pH=Ca. 6; Autoclave; High pressure;	65%

1,10-Phenanthroline (66-71-7) + cadmium(II) nitrate tetrhydrate + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) → C9H9O4P(2-)*Cd(2+)*C12H8N2*3H2O

Conditions	Yield
at 150℃; for 72h; pH=4; Autoclave;	61%

1H-imidazole (288-32-4) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) + uranyl(VI) acetate dihydrate → Co(imidazole)2(UO2)3((2-carboxyethyl)(phenyl)phosphinic acid(-2H))4

Conditions	Yield
In water at 160℃; for 72h; pH=4 - 5; Autoclave; High pressure;	61%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) + nickel diacetate (373-02-4, 14998-37-9, 33025-09-1, 94044-50-5, 98268-31-6) + uranyl(VI) acetate dihydrate + 1,4-bis-(1H-imidazol-1-yl)benzene (25372-07-0) → [Ni(1,4-di(1H-imidazol-1-yl)benzene)2(H2O)2][(UO2)3((2-carboxyethyl)(phenyl)phosphinic acid(-2H))4]·2H2O

Conditions	Yield
With ammonium hydroxide at 160℃; for 72h; pH=3.5 - 4.5; Autoclave; High pressure;	61%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → {[KH(Ph-PO2-C2H4-COOH)2]·H2O}∞

Conditions	Yield
With potassium hydroxide In water at 20℃; for 0.166667h;	60%

1,10-Phenanthroline (66-71-7) + zinc(II) nitrate hexahydrate + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → Zn(2-carboxyethyl(phenyl)phosphinate)(1,10-phenanthroline)*5H2O

Conditions	Yield
With sodium hydroxide In water at 150℃; for 73h; pH=5; Autoclave;	60%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) + cobalt(II) acetate (71-48-7, 917-69-1, 5931-89-5, 55881-15-7, 68931-68-0, 68931-69-1, 93029-27-7) + uranyl(VI) acetate dihydrate + 1,4-bis-(1H-imidazol-1-yl)benzene (25372-07-0) → [Co(1,4-di(1H-imidazol-1-yl)benzene)2(H2O)2][(UO2)3((2-carboxyethyl)(phenyl)phosphinic acid(-2H))4]·2H2O

Conditions	Yield
With ammonium hydroxide at 160℃; for 72h; pH=3.5 - 5; Autoclave; High pressure;	59%

1,10-Phenanthroline (66-71-7) + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) + manganese (II) acetate tetrahydrate (6156-78-1) → C9H9O4P(2-)*Mn(2+)*3H2O*C12H8N2

Conditions	Yield
at 20℃; for 24h; pH=5;	56%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + manganese(II) acetate (638-38-0, 993-02-2, 2180-18-9, 15411-95-7, 22981-23-3, 27004-39-3) + uranyl(VI) acetate dihydrate + 1,4-bis-(1H-imidazol-1-yl)benzene (25372-07-0) → Mn(1,4-di(1H-imidazol-1-yl)benzene)(UO2)2((2-carboxyethyl)(phenyl)phosphinic acid(-2H))3

Conditions	Yield
With ammonium hydroxide In water at 160℃; for 72h; pH=4 - 6; Autoclave; High pressure;	51%

3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) → C9H9O4P(2-)*Li(1+)*H(1+)

Conditions	Yield
With lithium hydroxide In water at 50℃;	45%

1,10-Phenanthroline (66-71-7) + cadmium(II) acetate monohydrate + 3-[hydroxy(phenyl)phosphinyl]propionic acid (14657-64-8) + water (7732-18-5) → C42H38Cd2N4O10P2*2H2O

Conditions	Yield
at 20℃; for 48h;	45%

Upstream product

• 2071-68-3 3-(chlorophenylphosphinyl)-propionyl chloride 
• 644-97-3 Dichlorophenylphosphine 
• 79-10-7 acrylic acid 
• 14795-21-2 galactose-α-1-phosphate barium salt 
• 1476-50-2 uridine 5'-triphosphate trisodium salt 
• 14576-56-8 butyl 3-[butoxy(phenyl)phosphinyl]propionate 
• 6172-81-2 butyl phenylphosphinate 
• 202477-16-5 3-(butoxy-phenyl-phosphinoyl)-propionic acid methyl ester 
• 857470-46-3 (2-cyano-ethyl)-phenyl-phosphinic acid butyl ester 

Downstream Products

• 13317-44-7 ethyl(phenyl)phosphinic acid 

Relevant articles and documents

Method for producing 2-carboxethyl phenylphosphinic acid without wastewater

The invention relates to a method for producing 2-carboxethyl phenylphosphinic acid without wastewater. According to the technical solution, dichlorophenylphosphine, acyclic acid and water are taken as raw materials, dichloropropane is taken as a solvent, and the method comprises the following steps of fully reacting the dichlorophenylphosphine and the acyclic acid to generate an acyl chloride intermediate; dropwise adding water into mixed liquor of the acyl chloride intermediate and dichloropropane according to a reaction mole ratio, and performing hydrolysis to generate the 2-carboxethyl phenylphosphinic acid. A required amount of water is added dropwise in reaction, so that production of a large amount of acidic wastewater is avoided, and moreover, a high-quality byproduct hydrochloric acid is recycled; the dichloropropane is taken as the solvent, so that the problem that conventional process wastewater contains 2-carboxethyl phenylphosphinic acid is solved, and yield is increased; the dichloropropane can be distilled for continuous use after being recycled for many times, so that the production cost is reduced, and the problem of existence of a large amount of wastewater in a conventional production process is solved.

Method for preparation of 3-(hydroxyphenyl phosphinyl)-propanoic acid

The present application relates to a method for the preparation of 3- (hydroxyphenylphosphinyl) -propanoic acid by the condensation of phenylphosphonous dichloride and acrylic acid and the hydrolysis of the condensate, in which, under a pressure of greater than 1 atm, acrylic acid is added at 65～110 °C at an amount more by 10～25 mole% than that of phenylphosphonous dichloride and the condensation is carried out at a temperature of 70～100 °C under at greater than 1 atm.

Production of 2-carboxyalkyl (phenyl)phosphinic acid

Processes for producing 2-carboxyalkyl(phenyl)phosphinic acid comprising hydrolyzing the reaction mixture produced from the reaction of dichloro(phenyl)phosphine with a carboxylic acid in the presence of water, wherein the hydrolysis is conducted with reduced levels of water.