3-Nitrothiophene

Base Information

• Chemical Name: 3-Nitrothiophene
• CAS No.: 822-84-4
• Molecular Formula: C4H3NO2S
• Molecular Weight: 129.139
• European Community (EC) Number: 212-502-9
• DSSTox Substance ID: DTXSID10231621
• Nikkaji Number: J59.667A
• Wikidata: Q83112558
• Mol file: 822-84-4.mol

Synonyms:3-Nitrothiophene;822-84-4;Thiophene, 3-nitro-;BRN 0110656;EINECS 212-502-9;5-17-01-00313 (Beilstein Handbook Reference);3-nitro-thiophene;SCHEMBL827990;DTXSID10231621;AKOS000282449;LS-153142;CS-0456009;FT-0717967;AI-942/25121011

Chemical Property of 3-Nitrothiophene

Chemical Property:

• Vapor Pressure: 0.125mmHg at 25°C
• Melting Point: 78.5°C
• Refractive Index: 1.5130 (estimate)
• Boiling Point: 226°Cat760mmHg
• Flash Point: 90.5°C
• PSA: 74.06000
• Density: 1.422g/cm³
• LogP: 2.17950
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 128.98844951
• Heavy Atom Count: 8
• Complexity: 101

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CSC=C1[N+](=O)[O-]

Technology Process of 3-Nitrothiophene

There total 16 articles about 3-Nitrothiophene 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: 75.0%

3-nitrothiophene-2-carboxylic acid (89283-80-7) → 3-nitrothiophene (822-84-4)

Guidance literature:

With copper(I) oxide; In quinoline; at 100 - 110 ℃; for 1h;

DOI:10.1080/00397919508011446

Reference yield: 70.0%

3-thienyl lithium (1192-06-9) → 3-nitrothiophene (822-84-4)

Guidance literature:

With dinitrogen tetraoxide; In tetrahydrofuran; -190 deg C -> room temperature;

DOI:10.1021/ja963658e

Reference yield: 62.0%

Thien-3-ylboronic acid (6165-69-1) → 3-nitrothiophene (822-84-4)

Guidance literature:

With 1,1,1,3',3',3'-hexafluoro-propanol; 2-nitrobenzo[d]isothiazol-3(2H)-one 1,1-dioxide; at 60 ℃; for 19h; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.orglett.0c00671

upstream raw materials:

thiophene

2-bromo-4-nitro-thiophene

2-bromo-3-nitrothiophene

4-nitro-2-thiophenecarboxylic acid

Downstream raw materials:

N-(thiophen-3-yl)acetamide

N-Thiophen-3-yl-benzamide

2,5-dibromo-3-nitro-thiophene

2,4-dinitrothiophene

Refernces

• 1、 McNabola, Neasa,O'Connor, Cornelius J.,Roydhouse, Mark D.,Wall, Michael D.,Southern, J. Mike. "A one-pot synthesis of 3-nitrothiophene and 3-nitro-2-substituted thiophenes". . p. 4598 - 4603. Retrieved 2015/06/08.
• 2、 Wu, Xiao-Feng,Schranck, Johannes,Neumann, Helfried,Beller, Matthias. "Convenient and mild synthesis of nitroarenes by metal-free nitration of arylboronic acids". supporting information; experimental part. p. 12462+12463. Retrieved 2012/02/03.