Methyl 5-bromo-4-nitrothiophene-2-carboxylate

Base Information

• Chemical Name: Methyl 5-bromo-4-nitrothiophene-2-carboxylate
• CAS No.: 38239-32-6
• Molecular Formula: C6H4 Br N O4 S
• Molecular Weight: 266.072
• Hs Code.: 2934999090
• NSC Number: 157845
• DSSTox Substance ID: DTXSID00303321
• Nikkaji Number: J270.081F
• Wikidata: Q82048522
• Mol file: 38239-32-6.mol

Synonyms:methyl 5-bromo-4-nitrothiophene-2-carboxylate;38239-32-6;5-BROMO-4-NITROTHIOPHENE-2-CARBOXYLIC ACID METHYL ESTER;2-Thiophenecarboxylic acid, 5-broMo-4-nitro-, Methyl ester (7CI,9CI);MFCD01567069;5-Bromo-4-nitro-thiophene-2-carboxylic acid methyl ester;2-bromo-5-methoxycarbonyl-3-nitrothiophene;NSC157845;SCHEMBL3880847;AMY1919;DTXSID00303321;CS-B0141;AKOS016001505;NSC-157845;DS-12316;SY284515;Methyl 5-bromo-4-nitro-2-thiophenecarboxylate #;A873897;2-Thiophenecarboxylic acid,5-bromo-4-nitro-,methyl ester;2-Thiophenecarboxylic acid,5-broMo-4-nitro-,Methyl ester (7CI,9CI)

Chemical Property of Methyl 5-bromo-4-nitrothiophene-2-carboxylate

Chemical Property:

• Vapor Pressure: 0.000251mmHg at 25°C
• Boiling Point: 324.1°Cat760mmHg
• Flash Point: 149.8°C
• PSA: 100.36000
• Density: 1.837g/cm³
• LogP: 2.72860
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 264.90444
• Heavy Atom Count: 13
• Complexity: 231

Purity/Quality:

99% ^*data from raw suppliers

Methyl 5-bromo-4-nitrothiophene-2-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1=CC(=C(S1)Br)[N+](=O)[O-]

Technology Process of Methyl 5-bromo-4-nitrothiophene-2-carboxylate

There total 2 articles about Methyl 5-bromo-4-nitrothiophene-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: 60.0%

5-bromo-2-thiophenecarboxylic acid methyl ester (62224-19-5) → methyl 5-bromo-4-nitrothiophene-2-carboxylate (38239-32-6)

Guidance literature:

With sulfuric acid; nitric acid;

DOI:10.1016/S0040-4039(01)01951-7

Reference yield:

5-bromothiophene-2-carboxylic acid (7311-63-9) → methyl 5-bromo-4-nitrothiophene-2-carboxylate (38239-32-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / H₂SO₄

2: 60 percent / HNO₃; H₂SO₄

With sulfuric acid; nitric acid;

DOI:10.1016/S0040-4039(01)01951-7

Reference yield:

methyl 5-bromo-4-nitrothiophene-2-carboxylate (38239-32-6) + aniline (62-53-3) → 5-anilino-4-nitro-thiophene-2-carboxylic acid methyl ester (78399-05-0) + aniline hydrobromide (542-11-0)

Guidance literature:

In methanol; at 20 ℃; Rate constant; Thermodynamic data; ΔH(excit.), ΔS(excit.);

DOI:10.1039/P29940002187

upstream raw materials:

5-bromo-2-thiophenecarboxylic acid methyl ester

5-bromothiophene-2-carboxylic acid

Downstream raw materials:

5-bromo-4-nitro-thiophene-2-carboxylic acid

4-Nitro-5-p-tolylamino-thiophene-2-carboxylic acid methyl ester

5-(4-Methoxy-phenylamino)-4-nitro-thiophene-2-carboxylic acid methyl ester

5-anilino-4-nitro-thiophene-2-carboxylic acid methyl ester

Refernces

• 1、 Kiryanov, Andre A.,Seed, Alexander J.,Sampson, Paul. "Ring fluorinated thiophenes: Applications to liquid crystal synthesis". . p. 8797 - 8800. Retrieved 2007/10/03.