alpha-(Methoxyimino)furan-2-acetic acid

Base Information

• Chemical Name: alpha-(Methoxyimino)furan-2-acetic acid
• CAS No.: 39684-61-2
• Molecular Formula: C7H7NO4
• Molecular Weight: 169.137
• European Community (EC) Number: 254-591-7,265-956-5
• UNII: P8VRH11AHT
• DSSTox Substance ID: DTXSID701274431
• Mol file: 39684-61-2.mol

Synonyms:39684-61-2;(2Z)-furan-2-yl(methoxyimino)ethanoic acid;(Z)-alpha-(Methoxyimino)furan-2-acetic acid;P8VRH11AHT;(Z)-2-(furan-2-yl)-2-(methoxyimino)acetic acid;(S)-2-Methoxyimino-2-furylacetic acid;Methoxyiminofuranyl acetic acid;EINECS 254-591-7;EINECS 265-956-5;alpha-(Methoxyimino)furan-2-acetic acid;(2Z)-2-(furan-2-yl)-2-(methoxyimino)acetic acid;65866-86-6;2-(furan-2-yl)-2-(methoxyimino)acetic acid;UNII-P8VRH11AHT;SCHEMBL4609969;2-furyl-2-methoxyiminoacetic acid;DTXSID701274431;BBL007871;STK802361;AKOS005622654;VS-01744;(2Z)-2-(2-Furyl)-2-methoxyiminoacetic acid;EN300-92111;(2Z)-2-(furan-2-yl)-2-methoxyiminoacetic acid;(Z)-2-(furan-2-yl)-2-(methoxyimino)aceticacid;EN300-7809195;(alphaZ)-alpha-(Methoxyimino)-2-furanacetic acid;CEFUROXIME SODIUM IMPURITY I [EP IMPURITY];(Z)-2-(2-FURYL)-2-METHOXYIMINOACETIC ACID;W-106411;METHOXYIMINOFURANYL ACETIC ACID [USP IMPURITY];(.ALPHA.Z)-.ALPHA.-(METHOXYIMINO)-2-FURANACETIC ACID;2-FURANACETIC ACID, .ALPHA.-(METHOXYIMINO)-, (.ALPHA.Z)-

Chemical Property of alpha-(Methoxyimino)furan-2-acetic acid

Chemical Property:

• Boiling Point: 284.694 °C at 760 mmHg
• PKA: 2.79±0.41(Predicted)
• Flash Point: 125.979 °C
• PSA: 72.03000
• Density: 1.32 g/cm³
• LogP: 0.71470
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 169.03750770
• Heavy Atom Count: 12
• Complexity: 202

Purity/Quality:

99% ^*data from raw suppliers

(2Z)-FURAN-2-YL(METHOXYIMINO)ETHANOIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CON=C(C1=CC=CO1)C(=O)O
• Isomeric SMILES: CO/N=C(/C1=CC=CO1)\C(=O)O
• Uses: (Z)-2-(Furan-2-yl)-2-(methoxyimino)acetic Acid (cas# 39684-61-2) is a useful reagent for the industrialization of Cefuroxime Sodium.

Technology Process of alpha-(Methoxyimino)furan-2-acetic acid

There total 2 articles about alpha-(Methoxyimino)furan-2-acetic 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: 36.0%

furan-2-yl-oxo-acetic acid (1467-70-5) + N-methoxylamine hydrochloride (593-56-6) → (2E)-2-(furan-2-yl)-2-(methoxyimino)acetic acid (69384-96-9,65866-86-6) + 2-(furan-2-yl)-2-(syn-methoxyimino)acetic acid (39684-61-2,65866-86-6)

Guidance literature:

With sodium carbonate; In methanol; for 1.5h; optical yield given as %de; Reflux;

DOI:10.1021/tx100446g

Reference yield:

O-Methylhydroxylamin (67-62-9) + furan-2-yl-oxo-acetic acid (1467-70-5) → (2E)-2-(furan-2-yl)-2-(methoxyimino)acetic acid (69384-96-9,65866-86-6) + 2-(furan-2-yl)-2-(syn-methoxyimino)acetic acid (39684-61-2,65866-86-6)

Guidance literature:

O-Methylhydroxylamin; furan-2-yl-oxo-acetic acid; With copper(ll) sulfate pentahydrate; sulfuric acid; In water; at 0 ℃; pH=3.5;

In water; at 8 ℃; for 4.5h; Reagent/catalyst; pH-value; Temperature;

Reference yield: 83.0%

2-(furan-2-yl)-2-(syn-methoxyimino)acetic acid (39684-61-2,65866-86-6) + para-methoxybenzyl (6R,7R)-7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride → 4-methoxybenzyl (6R,7R)-3-(chloromethyl)-7-((Z)-2-(furan-2-yl)-2-(methoxyimino) acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/acsinfecdis.0c00070

upstream raw materials:

furan-2-yl-oxo-acetic acid

N-methoxylamine hydrochloride

O-Methylhydroxylamin

Downstream raw materials:

(6R,7S)-7-{2-Furan-2-yl-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Refernces

• 1、 Montanez, Maria Isabel,Mayorga, Cristobalina,Torres, Maria Jose,Ariza, Adriana,Blanca, Miguel,Perez-Inestrosa, Ezequiel. "Synthetic approach to gain insight into antigenic determinants of cephalosporins: In vitro studies of chemical structure-IgE molecular recognition relationships". experimental part. p. 706 - 717. Retrieved 2012/03/11.