(Hydroxymethyl)phosphonic acid

Base Information

• Chemical Name: (Hydroxymethyl)phosphonic acid
• CAS No.: 2617-47-2
• Molecular Formula: CH5 O4 P
• Molecular Weight: 112.022
• European Community (EC) Number: 220-047-2
• NSC Number: 63035,41905
• UNII: DO34G523HF
• DSSTox Substance ID: DTXSID5062554
• Nikkaji Number: J21.059E
• Wikidata: Q27106896
• Metabolomics Workbench ID: 53221
• Mol file: 2617-47-2.mol

Synonyms:hydroxymethylphosphonate

Chemical Property of (Hydroxymethyl)phosphonic acid

Chemical Property:

• Vapor Pressure: 1.52E-08mmHg at 25°C
• Melting Point: 95-97℃
• Refractive Index: 1.4970
• Boiling Point: 413°Cat760mmHg
• PKA: 2.58±0.10(Predicted)
• Flash Point: 203.6°C
• PSA: 87.57000
• Density: 1.815g/cm³
• LogP: -0.88610
• XLogP3: -2.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 111.99254563
• Heavy Atom Count: 6
• Complexity: 71.6

Purity/Quality:

99.9% ^*data from raw suppliers

Phosphonomethanol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(O)P(=O)(O)O
• Uses: Phosphonomethanol has been used in the investigation on the stereochemistry of 2-Hydroxyethylphosphonate Dioxygenase.

Technology Process of (Hydroxymethyl)phosphonic acid

There total 30 articles about (Hydroxymethyl)phosphonic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 34.9%

2,2'-oxybis-acetic acid (110-99-6) → hydroxymethylphosphonic acid (2617-47-2) + (oxybis(methylene))diphosphonic acid (44991-95-9)

Guidance literature:

2,2'-oxybis-acetic acid; With methanesulfonic acid; phosphorus trichloride; at 50 - 80 ℃; for 3h; Inert atmosphere;

With water; at 120 ℃; for 2h; Inert atmosphere;

With sodium hydroxide; at 140 ℃; for 2h; Inert atmosphere;

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + (phenylmethoxy)methylphosphonic acid diethyl ester (89268-01-9) → chloroethane (75-00-3) + hydroxymethylphosphonic acid (2617-47-2) + benzyl alcohol (100-51-6,185532-71-2)

Guidance literature:

at 100 - 150 ℃;

Reference yield:

N-<(dimethoxyphosphinyl)methyl>glycine (65886-96-6) → hydroxymethylphosphonic acid (2617-47-2) + <<(carboxymethyl)imino>dimethylene>bisphosphonic acid (2439-99-8) + N-methyl N-phosphonomethylglycine (24569-83-3) + N-(phosphonemethyl)glycine (1071-83-6)

Guidance literature:

With hydrogenchloride; Yield given. Yields of byproduct given;

upstream raw materials:

formaldehyd

Trimethyl borate

chloromethylphosphonic acid

(phenylmethoxy)methylphosphonic acid diethyl ester

Downstream raw materials:

(Methyl-diphenyl-silyloxy)-methylphosphonsaeure-bis-(methyl-diphenyl-silylester)

-methanol

(Triphenylsilyloxy-methyl)-phosphonsaeure-bis-triphenylsilylester

chloromethylphosphonic dichloride

Refernces

• 1、 Gauvry,Mortier. "Dealkylation of dialkyl phosphonates with boron tribromide". . p. 553 - 554. Retrieved 2001.
• 2、 -. "METHOD FOR THE MANUFACTURE OF COMPOUNDS CONTAINING AN ALPHA-OXYPHOSPHORUS GROUP BY USING AN ACTIVATOR". Page/Page column 41; 42. . Retrieved 2013/03/26.
• 3、 Troev,Todorov,Naydenova,Mitova,Vassilev. "A study of the reaction of phosphorus trichloride with paraformaldehyde in the presence of carboxylic acids". . p. 1147 - 1155. Retrieved 2013/09/23.