Benzo[b]thiophene-3-acetonitrile

Base Information

• Chemical Name: Benzo[b]thiophene-3-acetonitrile
• CAS No.: 3216-48-6
• Molecular Formula: C10H7NS
• Molecular Weight: 173.238
• Hs Code.: 2934999090
• European Community (EC) Number: 221-733-4
• NSC Number: 332302
• UNII: JYC4JL4XSU
• DSSTox Substance ID: DTXSID40185946
• Nikkaji Number: J262.320J
• Wikidata: Q83057120
• Mol file: 3216-48-6.mol

Synonyms:3216-48-6;Benzo[b]thiophene-3-acetonitrile;2-(Benzo[b]thiophen-3-yl)acetonitrile;2-(1-benzothiophen-3-yl)acetonitrile;Benzo(b)thiophene-3-acetonitrile;Thianaphthene-3-acetonirile;(Benzo[b]thiophen-3-yl)acetonitrile;1-Benzothien-3-ylacetonitrile;Benzo[b]thiophen-3-yl-acetonitrile;2-benzo[b]thiophen-3-ylacetonitrile;EINECS 221-733-4;NSC-332302;3-(Cyanomethyl)-1-benzothiophene;NSC332302;JYC4JL4XSU;3-Benzothienylacetonitrile;3-cyanomethylbenzothiophene;SCHEMBL274426;benzo[b]thiophen-3-acetonitril;(1-benzothien-3-yl)acetonitrile;3-(Cyanomethyl)benzo[b]thiophene;DTXSID40185946;C10-H7-N-S;Acetonitrile, 2-(3-benzothieny)-;2-(benzothiophen-3-yl)acetonitrile;STR04035;2-(Benzo[b]thien-3-yl)acetonitrile;MFCD00027389;AKOS009157683;NSC 332302;CS-0216424;FT-0622692;EN300-42832;A875685;3-Cyanomethylthianaphthene~Thianaphthene-3-acetonitrile;Z431602866

Chemical Property of Benzo[b]thiophene-3-acetonitrile

Chemical Property:

• Vapor Pressure: 8.81E-05mmHg at 25°C
• Melting Point: 65-67 °C
• Refractive Index: 1.668
• Boiling Point: 340.1 °C at 760 mmHg
• Flash Point: 159.5 °C
• PSA: 52.03000
• Density: 1.244 g/cm³
• LogP: 2.96738
• Water Solubility.: Insoluble in water.
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 173.02992040
• Heavy Atom Count: 12
• Complexity: 205

Purity/Quality:

99% ^*data from raw suppliers

2-(1-Benzothiophen-3-yl)acetonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R22:Harmful if swallowed.
• Hazard Codes: R22:Harmful if swallowed.
• Statements: 22
• Safety Statements: 22-36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CS2)CC#N
• Uses: Benzo[b]thiophene-3-acetonitrile is used to produce 2-(5-Bromo-benzo[b]thiophen-3-yl)-ethylamine; hydrochloride. It is also used as pharmaceutical intermediates.

Technology Process of Benzo[b]thiophene-3-acetonitrile

There total 12 articles about Benzo[b]thiophene-3-acetonitrile 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: 85.0%

C16H14N2O2S2 + potassium thioacyanate (333-20-0) → 2-(benzo[b]thiophen-3-yl)acetonitrile (3216-48-6)

Guidance literature:

With copper(l) iodide; oxygen; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; In 1-methyl-pyrrolidin-2-one; acetonitrile; at 80 ℃; for 7h; under 760.051 Torr; Molecular sieve; Green chemistry;

DOI:10.1021/acs.joc.7b00836

Reference yield: 65.0%

3-chloromethylbenzothiophene (3216-47-5) + sodium cyanide (143-33-9,25596-52-5) → 2-(benzo[b]thiophen-3-yl)acetonitrile (3216-48-6)

Guidance literature:

In dimethyl sulfoxide; at 20 ℃; for 18.25h;

Reference yield: 53.0%

benzo[b]thiophene-3-ylacetaldehyde (874338-74-6) → 2-(benzo[b]thiophen-3-yl)acetonitrile (3216-48-6)

Guidance literature:

With ammonia; iodine; at 0 ℃; for 1h;

DOI:10.1002/ejoc.201700277

upstream raw materials:

3-chloromethylbenzothiophene

sodium cyanide

potassium cyanide

Benzo[b]thiophene

Downstream raw materials:

(Z)-2-(benzo[b]thiophen-3-yl)-3-(pyridin-4-yl)acrylonitrile

(Z)-2-benzo[b]thiophen-3-yl-3-pyridin-3-yl-acrylonitrile

methyl 3-benzothienylacetate

2-(3-benzothienyl)-3-(p-tolyl)propenenitrile

Refernces

• 1、 Huang, Yubing,Yu, Yue,Zhu, Zhongzhi,Zhu, Chuanle,Cen, Jinghe,Li, Xianwei,Wu, Wanqing,Jiang, Huanfeng. "Copper-Catalyzed Cyanation of N-Tosylhydrazones with Thiocyanate Salt as the "cN" Source". . p. 7621 - 7627. Retrieved 2017/07/26.
• 2、 -. "FUSED HETEROCYCLIC COMPOUNDS USEFUL AS INHIBITORS OF HISTONE DEACETYLASE". Page/Page column 170-172. . Retrieved 2008/06/13.