5-Methylbenzo[b]thiophene

Base Information

• Chemical Name: 5-Methylbenzo[b]thiophene
• CAS No.: 14315-14-1
• Molecular Formula: C9H8S
• Molecular Weight: 148.229
• Hs Code.: 29309090
• European Community (EC) Number: 238-256-2
• DSSTox Substance ID: DTXSID3074523
• Nikkaji Number: J130.652I
• Wikidata: Q72491145
• ChEMBL ID: CHEMBL235508
• Mol file: 14315-14-1.mol

Synonyms:5-Methylbenzo[b]thiophene;14315-14-1;5-Methyl-1-benzothiophene;5-Methylbenzo(b)thiophene;Benzo[b]thiophene, 5-methyl-;5-methylbenzothiophene;5-methyl-benzo[b]thiophene;Benzo(b)thiophene, 5-methyl-;EINECS 238-256-2;5-Methylthianaphthene;5-methyl-benzothiophene;Benzothiophene, 5-mehyl;5-Methyl-benzo[d]thiophene;SCHEMBL155613;CHEMBL235508;DTXSID3074523;MFCD00052509;AKOS006220490;PS-4433;CS-0095170;FT-0620644;M2974;F11127;A808027;W-205588

Chemical Property of 5-Methylbenzo[b]thiophene

Chemical Property:

• Appearance/Colour: white low melting mass
• Vapor Pressure: 0.0514mmHg at 25°C
• Melting Point: 35-36 °C
• Refractive Index: 1.652
• Boiling Point: 242.951 °C at 760 mmHg
• Flash Point: 72.395 °C
• PSA: 28.24000
• Density: 1.146 g/cm³
• LogP: 3.20970
• Storage Temp.: 2-8°C
• Water Solubility.: Insoluble in water.
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 148.03467143
• Heavy Atom Count: 10
• Complexity: 122

Purity/Quality:

99% ^*data from raw suppliers

5-Methylbenzo[b]thiophene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26-22

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)SC=C2
• Uses: 5-Methylbenzo[b]thiophene is useful in substituted thiophene for proteomics research.

Technology Process of 5-Methylbenzo[b]thiophene

There total 17 articles about 5-Methylbenzo[b]thiophene 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: 95.0%

5-bromobenzo[b]thiophene (4923-87-9) + dihydroxy-methyl-borane (13061-96-6) → 5-methylthianaphthene (14315-14-1)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate monohydrate; palladium diacetate; In 1,4-dioxane; at 100 ℃; for 3h; Sealed tube;

DOI:10.1021/acs.orglett.0c04114

Reference yield: 85.0%

→ 5-methylthianaphthene (14315-14-1)

Guidance literature:

With polyphosphoric acid; In chlorobenzene; at 130 ℃; for 4h; Inert atmosphere;

Reference yield: 84.0%

1-(fur-3-yl)-2-(thiophen-2-yl)ethene → 5-methylthianaphthene (14315-14-1) + 5-(2-hydroxyethyl)benzo[b]thiophene (96803-30-4)

Guidance literature:

With lithium borohydride; potassium hydroxide; In methanol; water; at 40 ℃; for 3h; Overall yield = 89 %; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1016/j.tet.2014.01.035

upstream raw materials:

5-methyl-benzo[b]thiophen-3-ol

5-methyl-benzo[b]thiophene-2-carboxylic acid

p-tolylsulfanyl-acetaldehyde dimethylacetal

5-methylbenzothiophen-3(2H)-one

Downstream raw materials:

5-bromomethyl-benzo[b]thiophene

5-methyl-benzo[b]thiophene-2-carboxylic acid

5-methyl-3-phenylbenzo[b]thiophene

5-methylbenzothiophene-2-carboxylic acid methyl ester

Refernces

• 1、 Hu, Fangdong,Jia, Jie,Li, Ximing,Xia, Ying. "Enantioselective hydroarylation or hydroalkenylation of benzo[b]thiophene 1,1-dioxides with organoboranes". supporting information. p. 896 - 901. Retrieved 2021/02/01.
• 2、 Lee, Shao-Chi,Liao, Hsuan-Hung,Chatupheeraphat, Adisak,Rueping, Magnus. "Nickel-Catalyzed C?S Bond Formation via Decarbonylative Thioetherification of Esters, Amides and Intramolecular Recombination Fragment Coupling of Thioesters". supporting information. p. 3608 - 3612. Retrieved 2018/03/13.