Benzo[b]thiophen-3-amine

Base Information

• Chemical Name: Benzo[b]thiophen-3-amine
• CAS No.: 17402-82-3
• Molecular Formula: C8H7NS
• Molecular Weight: 149.21300
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID10458250
• Mol file: 17402-82-3.mol

Synonyms:Benzo[b]thiophen-3-amine;17402-82-3;1-benzothiophen-3-amine;3-Aminobenzothiophene;Benzo[b]thiophen-3-ylamine;MFCD11052626;3-Aminobenzo[b]thiophene;SCHEMBL1308770;DTXSID10458250;SPGRIJRGBVPWLZ-UHFFFAOYSA-N;AKOS006307879;ETHYL3,5,5-TRIMETHYLHEXANOATE;SY151802;CS-0448395;FT-0717973;EN300-128149;A881719;J-519700

Chemical Property of Benzo[b]thiophen-3-amine

Chemical Property:

• Vapor Pressure: 0.000506mmHg at 25°C
• Boiling Point: 313.1oC at 760 mmHg
• Flash Point: 143.2oC
• PSA: 54.26000
• Density: 1.294g/cm3
• LogP: 3.06470
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 149.02992040
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

97% ^*data from raw suppliers

Benzo[b]thiophen-3-amine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CS2)N

Technology Process of Benzo[b]thiophen-3-amine

There total 19 articles about Benzo[b]thiophen-3-amine 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: 82.0%

acetophenone (98-86-2) → 3-aminobenzo[b]thiophene (17402-82-3) + 4-phenyl-5H-1,2,3-dithiazole-5-thione (1116585-89-7) + 2-phenylbenzo[4,5]thieno[3,2-d]thiazole + benzo[4,5]thieno[3,2-d]thiazol-2-yl(phenyl)methanone + C16H11NOS

Guidance literature:

acetophenone; With urea; In dimethyl sulfoxide; at 80 ℃; for 0.5h;

With 1,4-diaza-bicyclo[2.2.2]octane; sulfur; In water; dimethyl sulfoxide; at 120 ℃; for 6h;

DOI:10.1021/acs.orglett.9b03414

Reference yield: 75.0%

3-Azidobenzothiophene (66768-65-8) → 3-aminobenzo[b]thiophene (17402-82-3) + 3-(diethylamino)-2-aminobenzothiophene

Guidance literature:

With diethylamine; at 90 ℃; for 5h;

Reference yield: 45.0%

3-Bromothianaphthene (7342-82-7) + 4-hexylaniline (33228-45-4) → 3-aminobenzo[b]thiophene (17402-82-3) + 3-(3-benzothienyl)benzothiophen (40306-93-2) + N-(p-hexylphenyl)-N-(2'-benzo[b]thienyl)-3-aminobenzo[b]thiophene (1174151-90-6)

Guidance literature:

With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 5h; Inert atmosphere; Reflux;

DOI:10.1021/ol901133m

upstream raw materials:

3-hydroxybenzothiophene

3-Azidobenzothiophene

dimethyl amine

diethylamine

Downstream raw materials:

3-hydroxybenzothiophene

3-Acetoamidobenzothiophene

Refernces

Copper(I)-catalyzed Cyclization Reactions of Ethyl (E)-α-Ethynyl-β-Aryl-α,β-Unsaturated Esters with N-Sulfonyl Azides: Synthesis of 1-Aminonaphthalene, 3-Aminobenzofuran, and 3-Aminothiobenzofuran Derivatives

10.1002/bkcs.11755

The study presents a synthetic method for the preparation of ethyl 4-(alkyl or arylsulfonamido)-2-naphthoates, which are derivatives of 1-aminonaphthalene, 3-aminobenzofuran, and 3-aminobenzothiophene. These compounds are significant due to their presence in biologically active molecules used in cancer treatment and as inhibitors for various enzymes. The synthesis involves a copper(I)-catalyzed cyclization reaction of ethyl (E)-α-ethynyl-β-aryl-α,β-unsaturated esters with N-sulfonyl azides in the presence of 2,6-lutidine in THF at 60°C for 3 hours. This method efficiently produces a wide range of the aforementioned derivatives with the release of molecular nitrogen. The chemicals used in the study include ethyl (E)-α-ethynyl-β-aryl-α,β-unsaturated esters as starting materials, N-sulfonyl azides as reactants, 2,6-lutidine as a base, and copper(I) as a catalyst, all serving specific roles in the cyclization reaction to form the desired aminonaphthalene and related derivatives.