Methyl 3-bromothiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 3-bromothiophene-2-carboxylate
• CAS No.: 26137-08-6
• Molecular Formula: C6H5BrO2S
• Molecular Weight: 221.075
• Hs Code.: 29349990
• European Community (EC) Number: 862-002-5
• DSSTox Substance ID: DTXSID60372351
• Nikkaji Number: J1.360.599H
• Wikidata: Q72488876
• Mol file: 26137-08-6.mol

Synonyms:methyl 3-bromothiophene-2-carboxylate;26137-08-6;3-Bromothiophene-2-carboxylic acid methyl ester;2-THIOPHENECARBOXYLIC ACID, 3-BROMO-, METHYL ESTER;MFCD00173839;3-Bromo-thiophene-2-carboxylic acid methyl ester;Maybridge3_006386;SCHEMBL318317;DTXSID60372351;PEGSJNCGPSIJOX-UHFFFAOYSA-N;2-methoxycarbonyl-3-bromothiophene;HMS1449C06;Methyl-3-bromothiophene carboxylate;methyl 3-bromo-2-thiophenecarboxylate;AKOS005260321;CCG-248284;CS-W002470;FS-2684;PB25989;IDI1_017773;AC-24319;SY011458;AM20090321;FT-0628543;M2590;3-bromo-2-thiophenecarboxylic acid methyl ester;EN300-111456;3-bromo-2-thiophenecarboxylic acid, methyl ester;A818207;AN-584/43414011;J-512148;3-Bromo-2-(methoxycarbonyl)thiophene, Methyl 3-bromo-2-thenoate

Chemical Property of Methyl 3-bromothiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.0201mmHg at 25°C
• Melting Point: 50 °C
• Refractive Index: 1.577
• Boiling Point: 251.7 °C at 760 mmHg
• Flash Point: 106 °C
• PSA: 54.54000
• Density: 1.662 g/cm³
• LogP: 2.29720
• Storage Temp.: Keep in dark place,Sealed in dry,Store in freezer, under -20°C
• Water Solubility.: Slightly soluble in water.
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 219.91936
• Heavy Atom Count: 10
• Complexity: 140

Purity/Quality:

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

Methyl 3-Bromothiophene-2-carboxylate >98.0%(GC) ^*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: COC(=O)C1=C(C=CS1)Br
• Uses: Methyl 3-bromothiophene-2-carboxylate is employed as a intermediate for pharmaceutical and chemical research.

Technology Process of Methyl 3-bromothiophene-2-carboxylate

There total 6 articles about Methyl 3-bromothiophene-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%

methanol (67-56-1) + 3-bromothiophene-2-carboxylic acid (7311-64-0) → methyl 3-bromothiophene-2-carboxylate (26137-08-6)

Guidance literature:

With hydrogenchloride; sulfuric acid; In 1,4-dioxane; for 24h; Reflux;

Reference yield: 91.6%

Methyl 3-aminothiophene-2-carboxylate (22288-78-4) → methyl 3-bromothiophene-2-carboxylate (26137-08-6)

Guidance literature:

Methyl 3-aminothiophene-2-carboxylate; With hydrogen bromide; at 20 ℃; for 0.25h;

With sodium nitrite; In water; at 0 - 5 ℃; for 1h;

With hydrogen bromide; copper(I) bromide; In water; at 60 - 65 ℃; for 2h;

Reference yield:

3-Bromothiophene (872-31-1) + carbon dioxide (124-38-9,18923-20-1) + methyl iodide (74-88-4) → 4-bromothiophene-2-carboxylic acid methyl ester (62224-16-2) + methyl 3-bromothiophene-2-carboxylate (26137-08-6) + dimethyl 3-bromothiophene-2,5-carboxylate (7311-79-7)

Guidance literature:

3-Bromothiophene; carbon dioxide; With silver carbonate; lithium tert-butoxide; In N,N-dimethyl-formamide; at 90 ℃; for 15h; under 1500.15 Torr; Inert atmosphere; Glovebox; Autoclave;

methyl iodide; In N,N-dimethyl-formamide; at 90 ℃; for 2h; Overall yield = 72 percent; Overall yield = 159 mg;

DOI:10.1021/acs.organomet.1c00372

upstream raw materials:

Methyl 3-aminothiophene-2-carboxylate

methanol

3-bromo-thiophene-2-carbonyl chloride

3-bromothiophene-2-carboxylic acid

Downstream raw materials:

methyl 3-(phenylamino)-2-thiophenecarboxylate

3-bromo-2-hydroxymethyl-thiophene

3-bromothiophene-2-carboxylic acid

13-cyclohexyl-3-methoxy-6-[2-(methoxycarbonyl)-3-thienyl]-7H-indolo[2,1-a][2]benzazepine-10-carboxylic acid 1,1-dimethylethyl ester

Refernces

• 1、 Lee, Mijung,Hwang, Young Kyu,Kwak, Jaesung. "Ag(I)-Catalyzed C-H Carboxylation of Thiophene Derivatives". supporting information. p. 3136 - 3144. Retrieved 2021/09/30.
• 2、 Giofrè, Salvatore V.,Mancuso, Raffaella,Araniti, Fabrizio,Romeo, Roberto,Iannazzo, Daniela,Abenavoli, Maria Rosa,Gabriele, Bartolo. "Microwave-Assisted Synthesis of Sulfurated Heterocycles with Herbicidal Activity: Reaction of 2-Alkynylbenzoic Acids with Lawesson's Reagent". . p. 942 - 950. Retrieved 2019/07/31.