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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.

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  • 22987-21-9 Structure
  • Basic information

    1. Product Name: 2-HYDROXYETHYL PHOSPHONIC ACID
    2. 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
    3. CAS NO:22987-21-9
    4. Molecular Formula: C2H7O4P
    5. Molecular Weight: 126.05
    6. EINECS: 245-370-6
    7. Product Categories: N/A
    8. Mol File: 22987-21-9.mol
    9. Article Data: 13
  • Chemical Properties

    1. Melting Point: N/A
    2. Boiling Point: 398.8°Cat760mmHg
    3. Flash Point: 195°C
    4. Appearance: /
    5. Density: 1.611g/cm3
    6. Vapor Pressure: 5.14E-08mmHg at 25°C
    7. Refractive Index: 1.494
    8. Storage Temp.: 2-8°C
    9. Solubility: DMSO (Sparingly), Methanol (Slightly)
    10. Stability: Hygroscopic
    11. CAS DataBase Reference: 2-HYDROXYETHYL PHOSPHONIC ACID(CAS DataBase Reference)
    12. NIST Chemistry Reference: 2-HYDROXYETHYL PHOSPHONIC ACID(22987-21-9)
    13. EPA Substance Registry System: 2-HYDROXYETHYL PHOSPHONIC ACID(22987-21-9)
  • Safety Data

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 22987-21-9(Hazardous Substances Data)

22987-21-9 Usage

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.

Check Digit Verification of cas no

The CAS Registry Mumber 22987-21-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,9,8 and 7 respectively; the second part has 2 digits, 2 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 22987-21:
(7*2)+(6*2)+(5*9)+(4*8)+(3*7)+(2*2)+(1*1)=129
129 % 10 = 9
So 22987-21-9 is a valid CAS Registry Number.
InChI:InChI=1/C2H7O4P/c3-1-2-7(4,5)6/h3H,1-2H2,(H2,4,5,6)

22987-21-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-hydroxyethylphosphonic acid

1.2 Other means of identification

Product number -
Other names 2-Hydroxyethanphosphonseaure

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:22987-21-9 SDS

22987-21-9Synthetic route

dimethyl 2-hydroxyethylphosphonate
54731-72-5

dimethyl 2-hydroxyethylphosphonate

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
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

(2-benzyloxy-ethyl)-phosphonic acid dibenzyl ester

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol at 20℃;97%
2-acetoxyethanephosphonic acid dimethyl ester
39118-50-8

2-acetoxyethanephosphonic acid dimethyl ester

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
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-bis(trimethylsilylester)

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
With water at 20 - 25℃;72%
diethyl <2-(benzyloxy)ethyl>phosphonate
727-18-4

diethyl <2-(benzyloxy)ethyl>phosphonate

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
With hydrogenchloride; water for 75h; Inert atmosphere; Reflux;63%
oxirane
75-21-8

oxirane

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
With phosphonic Acid at 0℃;30%
With sodium dihydrogen phosphate; water
(2-hydroxyethyl)phosphine
16247-01-1

(2-hydroxyethyl)phosphine

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
With dihydrogen peroxide
2-chloroethylphosphonic acid
16672-87-0

2-chloroethylphosphonic acid

A

ethene
74-85-1

ethene

B

vinylphosphonic acid
1746-03-8

vinylphosphonic acid

C

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
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-acetoxyethanephosphonic acid dimethyl ester

A

2-chloroethylphosphonic acid
16672-87-0

2-chloroethylphosphonic acid

B

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

C

β-Acetoxyethanphosphonsaeure
32541-80-3

β-Acetoxyethanphosphonsaeure

Conditions
ConditionsYield
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

2-Acetoxyethanphosphonseauredichlorid

A

vinylphosphonic acid
1746-03-8

vinylphosphonic acid

B

2-chloroethylphosphonic acid
16672-87-0

2-chloroethylphosphonic acid

C

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

D

β-Acetoxyethanphosphonsaeure
32541-80-3

β-Acetoxyethanphosphonsaeure

E

2-(2-Hydroxyethan-hydrogenphosphonato)-ethanphosphonseaure

2-(2-Hydroxyethan-hydrogenphosphonato)-ethanphosphonseaure

Conditions
ConditionsYield
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-Acetoxyethanphosphonsaeure-bis(trimethylsilylester)

A

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

B

β-Acetoxyethanphosphonsaeure
32541-80-3

β-Acetoxyethanphosphonsaeure

Conditions
ConditionsYield
With water at 10 - 15℃; for 24h; Product distribution; hydrolysis;A 84 % Spectr.
B 15 % Spectr.
2-Methoxyethanphosphoseauredimethylester
26119-43-7

2-Methoxyethanphosphoseauredimethylester

A

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

B

2-Methoxyethanphosphonseaure

2-Methoxyethanphosphonseaure

C

2-(2-Hydroxyethan-hydrogenphosphonato)-ethanphosphonseaure

2-(2-Hydroxyethan-hydrogenphosphonato)-ethanphosphonseaure

D

hydroxyethylenediphosphonic acid
84549-24-6

hydroxyethylenediphosphonic acid

Conditions
ConditionsYield
With water at 160℃; for 60h; Product distribution; hydrolysis;
(2-hydroxyethyl)phosphonic acid-1.5cyclohexylamine
132155-50-1

(2-hydroxyethyl)phosphonic acid-1.5cyclohexylamine

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
With Dowex 50 (H+) In water
(2-hydroxyethyl)phosphine
16247-01-1

(2-hydroxyethyl)phosphine

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

triethyl borate
150-46-9

triethyl borate

phosphorus trichloride
7719-12-2, 52843-90-0

phosphorus trichloride

oxygen

oxygen

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
at 0℃; anschliessend mit Wasser;
ethylphosphonic acid
6779-09-5

ethylphosphonic acid

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

Conditions
ConditionsYield
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

bis(2-chloroethyl) 2-chloroethylphosphonate

A

2-chloroethylphosphonic acid
16672-87-0

2-chloroethylphosphonic acid

B

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

C

1,2-dichloro-ethane
107-06-2

1,2-dichloro-ethane

D

2-chloro-ethanol
107-07-3

2-chloro-ethanol

Conditions
ConditionsYield
With hydrogenchloride at 120℃; under 3800 Torr; for 16h; Product distribution; Further Variations:; Pressures; Temperatures;
2-chloroethylphosphonic acid
16672-87-0

2-chloroethylphosphonic acid

A

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

B

2-oxo-2-hydroxy-1,2-oxaphosphetane

2-oxo-2-hydroxy-1,2-oxaphosphetane

C

2-hydroxyethylphosphonyl phosphate

2-hydroxyethylphosphonyl phosphate

Conditions
ConditionsYield
In aq. buffer pH=7.4; Kinetics; Mechanism;
(Z)-9-octadecenoyl chloride
112-77-6

(Z)-9-octadecenoyl chloride

β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

(Z)-Octadec-9-enoic acid 2-phosphono-ethyl ester

(Z)-Octadec-9-enoic acid 2-phosphono-ethyl ester

Conditions
ConditionsYield
With pyridine at -20℃;56%
β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

dimethyl 2-hydroxyethylphosphonate
54731-72-5

dimethyl 2-hydroxyethylphosphonate

Conditions
ConditionsYield
In methanol; diethyl ether
β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

fosfomycin
23155-02-4

fosfomycin

Conditions
ConditionsYield
In water at 28℃; for 120h; blocked mutant of Streptomyces wedmorensis ATCC 21239, pH 8.0;
β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

A

formic acid
64-18-6

formic acid

B

hydroxymethylphosphonic acid
2617-47-2

hydroxymethylphosphonic acid

Conditions
ConditionsYield
With oxygen pH=7.5; aq. buffer; Enzymatic reaction;
β-Hydroxyethanphosphonsaeure
22987-21-9

β-Hydroxyethanphosphonsaeure

2-hydroxyethylphosphonic acid monomethyl ester
54731-76-9

2-hydroxyethylphosphonic acid monomethyl ester

Conditions
ConditionsYield
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

β-Hydroxyethanphosphonsaeure

methylphosphonic acid
993-13-5

methylphosphonic acid

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

22987-21-9Relevant articles and documents

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

Woodyer, Ryan D.,Li, Gongyong,Zhao, Huimin,Van Der Donk, Wilfred A.

, p. 359 - 361 (2007)

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

A novel biosurfactant, 2-acyloxyethylphosphonate, isolated from waterblooms of Aphanizomenon flos-aquae

Kaya, Kunimitsu,Morrison, Louise F.,Codd, Geoffrey A.,Metcalf, James S.,Sano, Tomoharu,Takagi, Hiroo,Kubo, Takuya

, p. 539 - 548 (2006)

A novel biosurfactant, 2-acyloxyethylphosphonate, was isolated from waterblooms of Aphanizomenon flos-aquae. Its structure was elucidated by chemical degradation and HRFABMS, GC/EI-MS and 1D- and 2D-NMR spectral analyses. The surfactant contained one mole of 2-hydroxyethylphosphonate and one mole of fatty acid, with hexadecanoic acid accounting for 84.1% of the total fatty acid content. The structure was confirmed by synthesis of 2-oleoyloxyethylphosphonate from ethylene oxide, phosphorus acid and oleic acid chloride. Considering the isolated surfactant molecule as hexadecanoyloxyethylphosphonic acid (mw. 364), the critical micelle concentration (CMC) was about 22 mM.

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

Gama, Simanga R.,Stankovic, Toda,Hupp, Kendall,Al Hejami, Ahmed,McClean, Mimi,Evans, Alysa,Beauchemin, Diane,Hammerschmidt, Friedrich,Pallitsch, Katharina,Zechel, David L.

, (2022)

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.

Characterization of the transient oxaphosphetane BChE inhibitor formed from spontaneously activated ethephon

Lantz, Stephen R.,Casida, John E.

, p. 1320 - 1322 (2013)

The major plant growth regulator ethephon degrades to ethylene and phosphate in aqueous solutions and plants and is spontaneously activated to a butyrylcholinesterase (BChE) inhibitor in alkaline solutions and animal tissues. In the present 31P NMR kinetic study of the reactions of ethephon in pH 7.4 carbonate buffer, we observed a transient peak at 28.11 ppm. The time course for the appearance and disappearance of this peak matches the activation/degradation kinetic profile of the BChE inhibitor, and the chemical shift supports the proposed 2-oxo-2-hydroxy-1,2-oxaphosphetane structure.

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

Song, Jibin,Wu, Binghui,Zhou, Zijian,Zhu, Guizhi,Liu, Yijing,Yang, Zhen,Lin, Lisen,Yu, Guocan,Zhang, Fuwu,Zhang, Guofeng,Duan, Hongwei,Stucky, Galen D.,Chen, Xiaoyuan

, p. 8110 - 8114 (2017)

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.

Pharmacophore elucidation of phosphoiodyn A - Potent and selective peroxisome proliferator-activated receptor β/δ agonists with neuroprotective activity

Kinarivala, Nihar,Suh, Ji Ho,Botros, Mina,Webb, Paul,Trippier, Paul C.

supporting information, p. 1889 - 1893 (2016/04/05)

We report the pharmacophore of the peroxisome proliferator-activated receptor δ (PPARδ) agonist natural product phosphoiodyn A is the phosphonate core. Synthesis of simplified phosphonate esters 13 and 15 provide structurally novel, highly selective and potent PPARδ agonists (EC50 = 78 and 112 nM, respectively). Further, both compounds demonstrate significant neuroprotective activity in an in vitro cellular model indicating that phosphonates may be an effective novel scaffold for the design of therapeutics for the treatment of neurodegenerative disorders.

PREPARATION OF A HYDROXYALKYL PHOSPHONIC ACID

-

Paragraph 0009, (2016/01/01)

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.

Comparative study on hydrolysis of 2-chloroethylphosphonic acid dialkylesters

Ilia, Gheorghe,Cǎprita, Adrian,Iliescu, Smaranda,Popa, Adriana,Pascariu, Aurelia,Bora, Alina,Dehelean, Gheorghe

, p. 501 - 506 (2007/10/03)

2-Chloroethylphosphonic acid dialkylesters (bis-(2-chloroethyl), dimethyl, diethyl, dipropyl, dibutyl and dipentylesters) were hydrolyzed in order to obtain 2-chloroethylphosphonic acid, used as a plant growth regulator. Experiments were made in neutral or acid conditions, in order to find optimal conditions for esters hydrolysis. The obtained 2-chloroethylphosphonic acid was tested, regarding its biological activity, on melon, cucumber, blackcurrant and bilberry.

A bimetallic system for the catalytic hydroxylation of remote primary C- H bonds in functionalized organics using dioxygen

Shen, Chengyu,Garcia-Zayas, Eduardo A.,Sen, Ayusman

, p. 4029 - 4031 (2007/10/03)

In a mixture of trifluoroacetic acid and water, the combination of metallic palladium and copper chloride catalyzes the hydroxylation of remote primary C-H bonds of a variety of acids, alcohols, and aliphatic halides, in the presence of carbon monoxide and dioxygen. Experiments suggest that the principal role of metallic palladium is to generate hydrogen peroxide in situ and that the species responsible for the remote hydroxylation of the substrate by hydrogen peroxide is copper chloride. The unusual preference for the catalytic hydroxylation of primary C-H bonds was also found in an experiment involving competition between ethane and either cumene or p- isopropylbenzoic acid: even though the solution concentration of ethane was significantly lower than the competing substrate, the vast majority of the oxidation product (ethanol) was derived from ethane. In the reactions studied, acetic acid and formic acid were formed through C-C cleavage steps. An examination of the site of C-C cleavage in propionic acid indicated that both C-C bonds were being broken.

MECHANISM OF THE PHOSPHORYLATION REACTION OF 2-HALOALKYLPHOSPHONIC ACIDS

Segall, Yoffi,Toia, Robert F.,Casida, John E.

, p. 191 - 194 (2007/10/02)

2-Haloalkylphosphonic acids require aqueous solutions of suitable pH to react as phosphorylating agents.Reaction rates are slow at pH1, moderate at pK12 (monoanion) and fast at pH>pK2 (dianion).The end products in water are phosphoric acid (major) and 2-hydroxyalkyl- and vinylphosphonic acids (minor).The dianinon is stable in non-aqueous solutions.The order of reactivity is bromo>chloro>>fluoro.Dehydrohalogenation is the major patway with mono- and diesters.In contrast, 2-chloroethylphosphonothioic acid dianion is stable even at pH 13.These findings are consistent with a mechanism involving a bimolecular process rather than an SN1 pathway via a metaphosphate intermediate.

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