22987-21-9

Basic information

• Product Name: 2-HYDROXYETHYL PHOSPHONIC ACID
• Synonyms: 2-HYDROXYETHYL PHOSPHONIC ACID;(2-hydroxyethyl)-phosphonicaci;BRN 1751212;2-Hydroxyethyl phosphonic acid, 97 %;2-Hydroxyethanephosphonic acid;Einecs 245-370-6;Phosphonic acid, (2-hydroxyethyl)-;P-(2-Hydroxyethyl)-phosphonic Acid
• CAS NO: 22987-21-9
• Molecular Formula: C₂H₇O₄P
• Molecular Weight: 126.05
• EINECS: 245-370-6
• Mol File: 22987-21-9.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 398.8°Cat760mmHg
• Flash Point: 195°C
• Appearance: /
• Density: 1.611g/cm³
• Vapor Pressure: 5.14E-08mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: 2-8°C
• Solubility: DMSO (Sparingly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 2-HYDROXYETHYL PHOSPHONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-HYDROXYETHYL PHOSPHONIC ACID(22987-21-9)
• EPA Substance Registry System: 2-HYDROXYETHYL PHOSPHONIC ACID(22987-21-9)

Safety Data

• Hazardous Substances Data: 22987-21-9(Hazardous Substances Data)

Usage

Description

2-Hydroxyethyl Phosphonic Acid is a phosphonic acid derivative, characterized by the presence of a phospho group at the 2-position of an ethanol molecule. It is a significant compound in the field of biochemistry and pharmaceuticals due to its unique structural properties and versatile applications.

Uses

Used in Biochemical Research:
2-Hydroxyethyl Phosphonic Acid is used as a substrate for studying the 2-hydroxyethylphosphonate dioxygenase reaction mechanism. This application is crucial for understanding the enzymatic processes and reactions involving phosphonic acid derivatives.
Used in Pharmaceutical Industry:
2-Hydroxyethyl Phosphonic Acid is used as a required intermediate in the biosynthesis of labelled Fosfomycin (F727502). Fosfomycin is an important antibiotic used for treating various bacterial infections, and the role of 2-Hydroxyethyl Phosphonic Acid in its production highlights its significance in the development of pharmaceutical compounds.

InChI:InChI=1/C2H7O4P/c3-1-2-7(4,5)6/h3H,1-2H2,(H2,4,5,6)

Synthetic route

dimethyl 2-hydroxyethylphosphonate (54731-72-5) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
Stage #1: dimethyl 2-hydroxyethylphosphonate With trimethylsilyl bromide In dichloromethane at 0 - 20℃; for 13h; Stage #2: In methanol at 20℃; for 12h;	100%

(2-benzyloxy-ethyl)-phosphonic acid dibenzyl ester → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃;	97%

2-acetoxyethanephosphonic acid dimethyl ester (39118-50-8) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With water at 100℃; for 15h;	89%
With hydrogenchloride In water at 100 - 115℃; for 14h;	97 % Spectr.

β-Hydroxyethanphosphonsaeure-bis(trimethylsilylester) (75502-78-2) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With water at 20 - 25℃;	72%

diethyl <2-(benzyloxy)ethyl>phosphonate (727-18-4) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With hydrogenchloride; water for 75h; Inert atmosphere; Reflux;	63%

oxirane (75-21-8) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With phosphonic Acid at 0℃;	30%
With sodium dihydrogen phosphate; water

(2-hydroxyethyl)phosphine (16247-01-1) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With dihydrogen peroxide

2-chloroethylphosphonic acid (16672-87-0) → ethene (74-85-1) + vinylphosphonic acid (1746-03-8) + β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With sodium hydroxide Mechanism; Product distribution; other 2-haloethylphosphonic acids or esters; var. aqueous and non-aqueous solvents, var. times, var. temp., var. pH; isotopic effect;

2-acetoxyethanephosphonic acid dimethyl ester (39118-50-8) → 2-chloroethylphosphonic acid (16672-87-0) + β-Hydroxyethanphosphonsaeure (22987-21-9) + β-Acetoxyethanphosphonsaeure (32541-80-3)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 11h;	A 3 % Spectr. B 77 % Spectr. C 18 % Spectr.
With water at 160℃; for 6.5h; Product distribution; hydrolysis, reagent, temperature;	A 3 % Spectr. B 77 % Spectr. C 18 % Spectr.

2-Acetoxyethanphosphonseauredichlorid (50655-62-4) → vinylphosphonic acid (1746-03-8) + 2-chloroethylphosphonic acid (16672-87-0) + β-Hydroxyethanphosphonsaeure (22987-21-9) + β-Acetoxyethanphosphonsaeure (32541-80-3) + 2-(2-Hydroxyethan-hydrogenphosphonato)-ethanphosphonseaure

Conditions	Yield
With water at 30 - 35℃; for 24h; Product distribution; hydrolysis, temperature;	A 0.4 % Spectr. B 3.4 % Spectr. C 60 % Spectr. D 30 % Spectr. E 4.4 % Spectr.

β-Acetoxyethanphosphonsaeure-bis(trimethylsilylester) (72563-41-8) → β-Hydroxyethanphosphonsaeure (22987-21-9) + β-Acetoxyethanphosphonsaeure (32541-80-3)

Conditions	Yield
With water at 10 - 15℃; for 24h; Product distribution; hydrolysis;	A 84 % Spectr. B 15 % Spectr.

2-Methoxyethanphosphoseauredimethylester (26119-43-7) → β-Hydroxyethanphosphonsaeure (22987-21-9) + 2-Methoxyethanphosphonseaure + 2-(2-Hydroxyethan-hydrogenphosphonato)-ethanphosphonseaure + hydroxyethylenediphosphonic acid (84549-24-6)

Conditions	Yield
With water at 160℃; for 60h; Product distribution; hydrolysis;

(2-hydroxyethyl)phosphonic acid-1.5cyclohexylamine (132155-50-1) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With Dowex 50 (H+) In water

(2-hydroxyethyl)phosphine (16247-01-1) + dihydrogen peroxide (7722-84-1) → β-Hydroxyethanphosphonsaeure (22987-21-9)

triethyl borate (150-46-9) + phosphorus trichloride (7719-12-2, 52843-90-0) + oxygen → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
at 0℃; anschliessend mit Wasser;

ethylphosphonic acid (6779-09-5) → β-Hydroxyethanphosphonsaeure (22987-21-9)

Conditions	Yield
With carbon monoxide; oxygen; trifluoroacetic acid; palladium on activated charcoal; copper dichloride at 75℃; under 56887.8 Torr; for 18h; Hydroxylation;	7 % Spectr.

bis(2-chloroethyl) 2-chloroethylphosphonate (6294-34-4) → 2-chloroethylphosphonic acid (16672-87-0) + β-Hydroxyethanphosphonsaeure (22987-21-9) + 1,2-dichloro-ethane (107-06-2) + 2-chloro-ethanol (107-07-3)

Conditions	Yield
With hydrogenchloride at 120℃; under 3800 Torr; for 16h; Product distribution; Further Variations:; Pressures; Temperatures;

2-chloroethylphosphonic acid (16672-87-0) → β-Hydroxyethanphosphonsaeure (22987-21-9) + 2-oxo-2-hydroxy-1,2-oxaphosphetane + 2-hydroxyethylphosphonyl phosphate

Conditions	Yield
In aq. buffer pH=7.4; Kinetics; Mechanism;

(Z)-9-octadecenoyl chloride (112-77-6) + β-Hydroxyethanphosphonsaeure (22987-21-9) → (Z)-Octadec-9-enoic acid 2-phosphono-ethyl ester

Conditions	Yield
With pyridine at -20℃;	56%

diazomethane (186581-53-3, 908094-01-9) + β-Hydroxyethanphosphonsaeure (22987-21-9) → dimethyl 2-hydroxyethylphosphonate (54731-72-5)

Conditions	Yield
In methanol; diethyl ether

β-Hydroxyethanphosphonsaeure (22987-21-9) → fosfomycin (23155-02-4)

Conditions	Yield
In water at 28℃; for 120h; blocked mutant of Streptomyces wedmorensis ATCC 21239, pH 8.0;

β-Hydroxyethanphosphonsaeure (22987-21-9) → formic acid (64-18-6) + hydroxymethylphosphonic acid (2617-47-2)

Conditions	Yield
With oxygen pH=7.5; aq. buffer; Enzymatic reaction;

β-Hydroxyethanphosphonsaeure (22987-21-9) + S-Adenosyl-L-methionine (14031-35-7, 17176-17-9, 29908-03-0, 75044-81-4, 78548-84-2, 79647-17-9, 91279-78-6) → 2-hydroxyethylphosphonic acid monomethyl ester (54731-76-9)

Conditions	Yield
With Escherichia coli AdoHcy nucleosidase; N-terminal hexahistidine tagged DhpI proteine; tris hydrochloride at 30℃; pH=7.8; Kinetics; Enzymatic reaction;

β-Hydroxyethanphosphonsaeure (22987-21-9) → methylphosphonic acid (993-13-5)

Conditions	Yield
With methylphosphonic acid synthase In aq. buffer at 20℃; for 2h; pH=7.5; Kinetics; Inert atmosphere; Enzymatic reaction;

Upstream product

• 75-21-8 oxirane 
• 16672-87-0 2-chloroethylphosphonic acid 
• 50655-62-4 2-Acetoxyethanphosphonseauredichlorid 
• 6779-09-5 ethylphosphonic acid 
• 727-18-4 diethyl <2-(benzyloxy)ethyl>phosphonate 
• 16051-76-6 phosphonoacetalhdehyde 
• 54731-72-5 dimethyl 2-hydroxyethylphosphonate 
• 6294-34-4 bis(2-chloroethyl) 2-chloroethylphosphonate 
• 150-46-9 triethyl borate 
• 7719-12-2 phosphorus trichloride 
• 16247-01-1 (2-hydroxyethyl)phosphine 
• 7722-84-1 dihydrogen peroxide 
• 75502-78-2 β-Hydroxyethanphosphonsaeure-bis(trimethylsilylester) 
• 132155-50-1 (2-hydroxyethyl)phosphonic acid-1.5cyclohexylamine 

Downstream Products

• 23155-02-4 fosfomycin 
• 64-18-6 formic acid 
• 2617-47-2 hydroxymethylphosphonic acid 
• 993-13-5 methylphosphonic acid 
• 54731-72-5 dimethyl 2-hydroxyethylphosphonate 

Relevant articles and documents

New insight into the mechanism of methyl transfer during the biosynthesis of fosfomycin

Hydroxyethylphosphonate is a required intermediate in fosfomycin biosynthesis. The Royal Society of Chemistry.

Biosynthesis of the Fungal Organophosphonate Fosfonochlorin Involves an Iron(II) and 2-(Oxo)glutarate Dependent Oxacyclase

The fungal metabolite Fosfonochlorin features a chloroacetyl moiety that is unusual within known phosphonate natural product biochemistry. Putative biosynthetic genes encoding Fosfonochlorin in Fusarium and Talaromyces spp. were investigated through reactions of encoded enzymes with synthetic substrates and isotope labelling studies. We show that the early biosynthetic steps for Fosfonochlorin involve the reduction of phosphonoacetaldehyde to form 2-hydroxyethylphosphonic acid, followed by oxidative intramolecular cyclization of the resulting alcohol to form (S)-epoxyethylphosphonic acid. The latter reaction is catalyzed by FfnD, a rare example of a non-heme iron/2-(oxo)glutarate dependent oxacyclase. In contrast, FfnD behaves as a more typical oxygenase with ethylphosphonic acid, producing (S)-1-hydroxyethylphosphonic acid. FfnD thus represents a new example of a ferryl generating enzyme that can suppress the typical oxygen rebound reaction that follows abstraction of a substrate hydrogen by a ferryl oxygen, thereby directing the substrate radical towards a fate other than hydroxylation.

Double-Layered Plasmonic–Magnetic Vesicles by Self-Assembly of Janus Amphiphilic Gold–Iron(II,III) Oxide Nanoparticles

Janus nanoparticles (JNPs) offer unique features, including the precisely controlled distribution of compositions, surface charges, dipole moments, modular and combined functionalities, which enable excellent applications that are unavailable to their symmetrical counterparts. Assemblies of NPs exhibit coupled optical, electronic and magnetic properties that are different from single NPs. Herein, we report a new class of double-layered plasmonic–magnetic vesicle assembled from Janus amphiphilic Au-Fe3O4 NPs grafted with polymer brushes of different hydrophilicity on Au and Fe3O4 surfaces separately. Like liposomes, the vesicle shell is composed of two layers of Au-Fe3O4 NPs in opposite direction, and the orientation of Au or Fe3O4 in the shell can be well controlled by exploiting the amphiphilic property of the two types of polymers.

PREPARATION OF A HYDROXYALKYL PHOSPHONIC ACID

The present invention is a process for converting a phosphonate to a hydroxyalkyl phosphonic acid comprising the step of contacting together water, the phosphonate, and a sulfonated or phosphonated heterogeneous catalyst under conditions sufficient to convert at least 50% of the phosphonate to the hydroxyalkyl phosphonic acid. The process of the present invention provides a way of preparing hydroxyalkyl phosphonic acids safely and economically, without corrosive effects.