Methyl 5-aminofuran-2-carboxylate

Base Information

• Chemical Name: Methyl 5-aminofuran-2-carboxylate
• CAS No.: 22600-30-2
• Molecular Formula: C6H7NO3
• Molecular Weight: 141.126
• Hs Code.: 2932190090
• European Community (EC) Number: 681-821-7
• DSSTox Substance ID: DTXSID90408031
• Nikkaji Number: J725.599C
• Wikidata: Q82213390
• Mol file: 22600-30-2.mol

Synonyms:methyl 5-aminofuran-2-carboxylate;22600-30-2;methyl 5-amino-2-furoate;5-aminofuran-2-carboxylic acid methyl ester;MFCD00051661;methyl5-amino-2-furoate;5-amino-2-furoic acid methyl ester;2-Furancarboxylic acid, 5-amino-, methyl ester;methyl 5-amino-2-furancarboxylate;methyl 5-amino-2-furate;methyl-2-amino-5-furoate;SCHEMBL223113;2-amino-5-methoxycarbonylfuran;DTXSID90408031;Methyl-5-aminofuran-2-carboxylate;XAA60030;AKOS000139506;AM10007;SB13379;AS-10222;SY036521;CS-0049008;FT-0628325;FT-0628847;EN300-27139;Z235345373

Chemical Property of Methyl 5-aminofuran-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00439mmHg at 25°C
• Melting Point: 132-134 °C
• Refractive Index: 1.527
• Boiling Point: 277.9 °C at 760 mmHg
• PKA: -0.67±0.10(Predicted)
• Flash Point: 121.9 °C
• PSA: 65.46000
• Density: 1.255 g/cm³
• LogP: 1.22960
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 141.042593085
• Heavy Atom Count: 10
• Complexity: 137

Purity/Quality:

98%,99%, ^*data from raw suppliers

Methyl5-Aminofuran-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 22-24/25-36/37-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC=C(O1)N

Technology Process of Methyl 5-aminofuran-2-carboxylate

There total 4 articles about Methyl 5-aminofuran-2-carboxylate 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: 89.0%

methyl 5-nitrofuran-2-carboxylate (1874-23-3) → methyl 5-amino-2-furoate (22600-30-2)

Guidance literature:

With potassium fluoride; polymethylhydrosiloxane; palladium diacetate; In tetrahydrofuran; water; at 20 ℃; for 0.5h;

DOI:10.1021/ol052120n

Reference yield:

2-furoic acid methyl ester (611-13-2) → methyl 5-amino-2-furoate (22600-30-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Ac₂O, nitric acid, 2.) N,N-diisopropylethylamine / 1) -5 deg C, 4 h; 2) CH₂Cl₂, rt, 15 h

2: 63 percent / H₂ / Pd/CaCO₃ / methanol / 20 h / 2068.6 Torr

With hydrogen; nitric acid; acetic anhydride; N-ethyl-N,N-diisopropylamine; Lindlar's catalyst; In methanol;

DOI:10.1021/jo9702599

Reference yield:

methyl 5-nitrofuran-2-carboxylate (1874-23-3) → methyl 5-amino-2-furoate (22600-30-2) + methyl 5-hydroxylamino-2-furoate (83329-44-6)

Guidance literature:

at 37 ℃; for 0.5h; hypoxanthine, milk xanthine oxidase, 33 mM Na-K-phosphate buffer (pH 7.4) containing acetone;

DOI:10.1248/cpb.30.2647

upstream raw materials:

methyl 5-nitrofuran-2-carboxylate

2-furoic acid methyl ester

Downstream raw materials:

5-[3-(3,4-Dimethoxy-phenyl)-propionylamino]-furan-2-carboxylic acid methyl ester

5-(2-Bromo-4,5-dimethoxy-benzoylamino)-furan-2-carboxylic acid methyl ester

5-acetylaminofuran-2-carboxylic acid

5-acetylamino-2-furancarboxylic acid methyl ester

Refernces

• 1、 Russell, M. Grace,Veryser, Cedrick,Hunter, James F.,Beingessner, Rachel L.,Jamison, Timothy F.. "Monolithic Silica Support for Immobilized Catalysis in Continuous Flow". supporting information. p. 314 - 319. Retrieved 2019/12/24.
• 2、 -. "IMIDAZOTHIADIAZOLE DERIVATIVES AS PROTEASE ACTIVATED RECEPTOR 4 (PAR4) INHIBITORS FOR TREATING PLATELET AGGREGATION". Paragraph 00260. . Retrieved 2013/11/18.