Methyl 3-amino-4-methylthiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 3-amino-4-methylthiophene-2-carboxylate
• CAS No.: 85006-31-1
• Molecular Formula: C7H9NO2S
• Molecular Weight: 171.22
• Hs Code.: 29349990
• European Community (EC) Number: 285-060-8
• UNII: 3LA24473AS
• DSSTox Substance ID: DTXSID50234070
• Nikkaji Number: J309.588F
• Wikidata: Q27257520
• Mol file: 85006-31-1.mol

Synonyms:Methyl 3-amino-4-methylthiophene-2-carboxylate;85006-31-1;Methyl3-amino-4-methylthiophene-2-carboxylate;3-Amino-4-methylthiophene-2-carboxylic Acid Methyl Ester;2-Thiophenecarboxylic acid, 3-amino-4-methyl-, methyl ester;3-Aminoarticaine;3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester;Methyl 3-amino-4-methyl-2-thenoate;MFCD00051822;UNII-3LA24473AS;3LA24473AS;EINECS 285-060-8;Methyl 3-amino-4-methyl-2-thiophenecarboxylate;methyl-3-amino-4-methylthiophene-2-carboxylate;Methyl 3-Amino-4-methylthiophene-2-carboxylate (3-Aminoarticaine);TricyclohexyltiNchloride;SCHEMBL163725;YICRPERKKBDRSP-UHFFFAOYSA-;DTXSID50234070;CHEBI:194924;GEO-01745;AKOS004912331;AC-8360;CCG-243249;CS-W020012;FS-1510;SDCCGMLS-0066226.P001;SY012772;Methyl 3-amino-4-methylthiophenecarboxylate;AM20110219;FT-0614987;M1772;methyl 3-amino-4-methylthiophene-2-carboxlate;EN300-104441;methyl 4-methyl-3-aminothiophene-2-carboxylate;methyl 3-amino-4-methyl-2-thiophene carboxylate;2-METHOXYCARBONYL-3-AMINO-4-METHYLTHIOPHENE;Q-100858;Methyl 3-amino-4-methylthiophene-2-carboxylate, 97%;Q27257520;ARTICAINE HYDROCHLORIDE IMPURITY I [EP IMPURITY];methyl 3-amino-thiophene-2-carboxylic acid methyl ester;3-Amino-4-methyl-2-thiophene carboxylic acid methyl ester;3-amino-4-methyl-thiophene-2-carboxylic acid methyl ester

Chemical Property of Methyl 3-amino-4-methylthiophene-2-carboxylate

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 0.000357mmHg at 25°C
• Melting Point: 85-88 °C(lit.)
• Refractive Index: 1.586
• Boiling Point: 318.6 °C at 760 mmHg
• PKA: 1.71±0.10(Predicted)
• Flash Point: 146.5 °C
• PSA: 80.56000
• Density: 1.264 g/cm³
• LogP: 2.00650
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• Water Solubility.: 1g/L at 35℃
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 171.03539970
• Heavy Atom Count: 11
• Complexity: 163

Purity/Quality:

99% ^*data from raw suppliers

Methyl 3-amino-4-methylthiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CSC(=C1N)C(=O)OC
• Uses: Methyl 3-Amino-4-methylthiophene-2-carboxylate is a versatile reactant used in various syntheses. It is used in the preparation of (oxalylamino)benzoic acids and (carboxyheteroarylamino)oxalic acids as selective and orally bioavailable nonpeptide inhibitors of protein-tyrosine phosphatase 1B.

Technology Process of Methyl 3-amino-4-methylthiophene-2-carboxylate

There total 2 articles about Methyl 3-amino-4-methylthiophene-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: 96.5%

4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester (2689-70-5) → 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester (85006-31-1)

Guidance literature:

4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester; With iron(III) chloride; 1,3,5-trichloro-2,4,6-triazine; hydroxylamine hydrochloride; In N,N-dimethyl-formamide; at 70 - 90 ℃; for 4h;

With ammonium hydroxide; for 0.5h; Reagent/catalyst; Temperature;

Reference yield:

3-amino-2-carbomethoxy-4-methyl-4,5-dihydrothiophene (125089-02-3) → 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester (85006-31-1)

Guidance literature:

With dihydrogen peroxide; In ethyl acetate; isopropyl alcohol;

Reference yield: 92.0%

3-bromo-1-trifluoromethylbenzene (401-78-5) + 3-amino-4-methyl-2-thiophenecarboxylic acid methyl ester (85006-31-1) → methyl 3-amino-4-methyl-5-(3-trifluoromethylphenyl)-thiophene-2-carboxylate (1246226-63-0)

Guidance literature:

With PdCl(C₃H₅)(dppb); potassium acetate; In N,N-dimethyl acetamide; at 120 ℃; for 20h; Inert atmosphere;

DOI:10.1021/ol101758w

upstream raw materials:

4-methyl-3-oxotetrahydro-2-thiophencarboxylic acid methyl ester

3-amino-2-carbomethoxy-4-methyl-4,5-dihydrothiophene

Downstream raw materials:

7-methylthieno<3,2-d>pyrimidine-2,4-dione

3-((benzyloxycarbonyl)glycyl)amino-2-methoxycarbonyl-4-methylthiophene

4-Methyl-3-(2-propoxy-benzoylamino)-thiophene-2-carboxylic acid methyl ester

methyl 3-((4-methoxyphenyl)sulfonamido)-4-methylthiophene-2-carboxylate

Refernces

• 1、 Barker, John M.,Huddleston, Patrick R.,Wood, Michael L.. "A rapid conversion of 3-oxothiolanes into 3-aminothiophenes". . p. 2565 - 2568. Retrieved 2007/10/03.
• 2、 -. "Process for preparing thiophene derivatives". . . Retrieved 2008/06/13.