Methyl 4-bromo-3-methoxythiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 4-bromo-3-methoxythiophene-2-carboxylate
• CAS No.: 110545-67-0
• Molecular Formula: C7H7 Br O3 S
• Molecular Weight: 251.09800
• Hs Code.: 2934999090
• European Community (EC) Number: 639-371-4
• DSSTox Substance ID: DTXSID90371630
• Wikidata: Q82159026
• Mol file: 110545-67-0.mol

Synonyms:methyl 4-bromo-3-methoxythiophene-2-carboxylate;110545-67-0;Methyl 4-bromo-3-(methyloxy)-2-thiophenecarboxylate;2-Thiophenecarboxylicacid, 4-bromo-3-methoxy-, methyl ester;Maybridge1_003930;SCHEMBL1529419;HMS552K14;DTXSID90371630;AAUKODCGPDBXCN-UHFFFAOYSA-N;MFCD00173933;AKOS015908738;CCG-242155;SB67089;TS-03421;CS-0211736;FT-0628621;D88141;methyl-3-methoxy4-bromo-2-thiophenecarboxylate;methyl4-bromo-3-methoxythiophene-2-carboxylate;Methyl 4-bromo-3-methoxy-2-thiophenecarboxylate;methyl-3-methoxy-4-bromo-2-thiophenecarboxylate;methyl-4-bromo-3-methoxy-2-thiophenecarboxylate;A802212;methyl 4-bromo-3-methoxy-thiophene-2-carboxylate;J-002444;2-Thiophenecarboxylicacid,4-bromo-3-methoxy-,methyl ester;4-bromo-3-methoxy-thiophene-2-carboxylic acid methyl ester

Chemical Property of Methyl 4-bromo-3-methoxythiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.00115mmHg at 25°C
• Melting Point: 73oC
• Boiling Point: 300oC at 760 mmHg
• Flash Point: 135.2oC
• PSA: 63.77000
• Density: 1.599g/cm3
• LogP: 2.30580
• Storage Temp.: 2-8°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 249.92993
• Heavy Atom Count: 12
• Complexity: 176

Purity/Quality:

98%min ^*data from raw suppliers

Methyl4-bromo-3-methoxythiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(SC=C1Br)C(=O)OC

Technology Process of Methyl 4-bromo-3-methoxythiophene-2-carboxylate

There total 3 articles about Methyl 4-bromo-3-methoxythiophene-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: 100.0%

methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate (95201-93-7) + methyl iodide (74-88-4) → methyl 4-bromo-3-methoxythiophene-2-carboxylate (110545-67-0)

Guidance literature:

With potassium carbonate; In acetone; for 6h; Heating / reflux;

Reference yield: 75.0%

methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate (95201-93-7) + dimethyl sulfate (77-78-1) → methyl 4-bromo-3-methoxythiophene-2-carboxylate (110545-67-0)

Guidance literature:

With potassium carbonate; In butanone; for 6h; Heating;

DOI:10.1016/0223-5234(87)90057-2

Reference yield:

methyl 3-hydroxy-2-thiophenecarboxylate (5118-06-9) → methyl 4-bromo-3-methoxythiophene-2-carboxylate (110545-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1: bromine / acetic acid / 24 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 20 h / 20 °C

With bromine; potassium carbonate; In acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.01.050

upstream raw materials:

methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate

dimethyl sulfate

methyl iodide

methyl 3-hydroxy-2-thiophenecarboxylate

Downstream raw materials:

N-[2-amino-1-(phenylmethyl)ethyl]-3-(methyloxy)-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide hydrochloride

1,1-dimethylethyl [2-({[3-(methyloxy)-4-(1-methyl-1H-pyrazol-5-yl)-2-thienyl]carbonyl}amino)-3-phenylpropyl]carbamate

N-[2-amino-1-(phenylmethyl)ethyl]-3-(methyloxy)-4-(1-methyl-1H-pyrazol-5-yl)-2-thiophenecarboxamide

Refernces

• 1、 Savitha, Gurunathan,Hergué, Noémie,Guilmet, Erwan,Allain, Magali,Frère, Pierre. "3-Alkoxy-4-bromothiophenes: General synthesis of monomers and regio-selective preparation of two dimers". . p. 1288 - 1291. Retrieved 2011.
• 2、 Corral,El-Ashmawy,Lissavetzky,et al.. "Synthesis and central relaxant activity of thiophene analogs of mephenesin and methocarbamol". . p. 251 - 254. Retrieved 1987.
• 3、 -. "Opioid receptor agonists and application thereof". Paragraph 2141; 2144; 2150-2154. . Retrieved 2019/01/24.