Methyl 4-bromo-3-hydroxythiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 4-bromo-3-hydroxythiophene-2-carboxylate
• CAS No.: 95201-93-7
• Molecular Formula: C6H5 Br O3 S
• Molecular Weight: 237.074
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID30380589
• Nikkaji Number: J284.778G
• Wikidata: Q72457051
• Mol file: 95201-93-7.mol

Synonyms:methyl 4-bromo-3-hydroxythiophene-2-carboxylate;95201-93-7;2-Thiophenecarboxylic acid, 4-bromo-3-hydroxy-, methyl ester;MFCD00052081;Maybridge1_004012;SCHEMBL1760863;HMS552O08;AMY7511;DTXSID30380589;UFTXASQYKJFRKI-UHFFFAOYSA-N;BCP06815;VDA20193;AKOS005067760;CCG-240049;BP-10143;SY025712;TS-03322;CS-0150885;FT-0628620;4-Bromo-3-hydroxy-2-(methoxycarbonyl)thiophene;methyl4-bromo-3-hydroxythiophene-2-carboxylate;Methyl 4-bromo-3-hydroxy-2-thiophenecarboxylate;Methyl-3-hydroxy-4-bromo-2-thiophenecarboxylate;Methyl-4-bromo-3-hydroxy-2-thiophenecarboxylate;A845231;(4-bromo-3-oxo-2-thienylidene)-methoxy-methanolate;2-Thiophenecarboxylicacid,4-bromo-3-hydroxy-,methyl ester;3-Hydroxy-4-bromothiophene-2-carboxylic acid methyl ester;4-bromo-3-hydroxythiophene-2-carboxylic acid methyl ester

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

Chemical Property:

• Vapor Pressure: 0.016mmHg at 25°C
• Melting Point: 79-80°C
• Boiling Point: 298.1°Cat760mmHg
• PKA: 7.93±0.15(Predicted)
• Flash Point: 134.1°C
• PSA: 74.77000
• Density: 1.982g/cm³
• LogP: 2.00280
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Water Solubility.: Sparingly Soluble in water 0.95 g/L @ 25°C.
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 235.91428
• Heavy Atom Count: 11
• Complexity: 164

Purity/Quality:

97% ^*data from raw suppliers

Methyl4-Bromo-3-hydroxythiophene-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:Irritating to eyes, respiratory system and skin.
• Hazard Codes: Xi:Irritant
• 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)O
• Uses: The synthesis of the thienopyranone scaffold began with the alkylation of methyl 4-bromo-3-hydroxythiophene-2-carboxylate with N-acetylmorpholine.

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

There total 3 articles about Methyl 4-bromo-3-hydroxythiophene-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: 80.0%

methyl 3-hydroxy-2-thiophenecarboxylate (5118-06-9) → methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate (95201-93-7)

Guidance literature:

With bromine; In acetic acid; at 20 ℃;

DOI:10.1016/j.tetlet.2009.06.085

Reference yield:

ethyl [(3,6-dimethoxypyridin-2-yl)amino]carbono-thioylcarbamate → 2-Amino-5,8-dimethoxy[1,2,4]-triazolo[1,5-a]pyridine + methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate (95201-93-7)

Guidance literature:

With hydroxylamine hydrochloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; ethanol; water;

Reference yield:

methyl 2-chloro-3-oxo-2,3-dihydrothiophen-2-yl-carboxylate (95201-94-8) → methyl 3-hydroxy-4-bromo-2-thiophenecarboxylate (95201-93-7)

Guidance literature:

With hydrogen bromide; acetic acid;

DOI:10.1016/j.tetlet.2017.05.025

upstream raw materials:

methyl 3-hydroxy-2-thiophenecarboxylate

methyl 2-chloro-3-oxo-2,3-dihydrothiophen-2-yl-carboxylate

Downstream raw materials:

methyl 4-bromo-3-methoxythiophene-2-carboxylate

C₁₄H₁₀O₃S