Benzothiazole

Base Information

• Chemical Name: Benzothiazole
• CAS No.: 95-16-9
• Deprecated CAS: 128366-28-9
• Molecular Formula: C7H5NS
• Molecular Weight: 135.189
• Hs Code.: 29342080
• European Community (EC) Number: 202-396-2
• NSC Number: 8040
• UNII: G5BW2593EP
• DSSTox Substance ID: DTXSID7024586
• Nikkaji Number: J40.177C
• Wikipedia: Benzothiazole
• Wikidata: Q419096
• Metabolomics Workbench ID: 45792
• ChEMBL ID: CHEMBL510309
• Mol file: 95-16-9.mol

Synonyms:benzothiazole

Chemical Property of Benzothiazole

Chemical Property:

• Appearance/Colour: yellow liquid with an unpleasant odour
• Vapor Pressure: 34 mm Hg ( 131 °C)
• Melting Point: 2 °C(lit.)
• Refractive Index: n20/D 1.642(lit.)
• Boiling Point: 227 °C at 760 mmHg
• PKA: 0.85±0.10(Predicted)
• Flash Point: 96.6 °C
• PSA: 41.13000
• Density: 1.272 g/cm³
• LogP: 2.29630
• Storage Temp.: Refrigerator
• Solubility.: 3g/l
• Water Solubility.: slightly soluble
• XLogP3: 2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 135.01427034
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

99%min ^*data from raw suppliers

Benzothiazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,Xi
• Statements: 22-20/21/22-36-25-24-20
• Safety Statements: 23-26-36-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Thiazoles
• Canonical SMILES: C1=CC=C2C(=C1)N=CS2
• Recent ClinicalTrials: Botulinum Toxin Injection to Prevent VT Storm
• Description: Benzothiazole and its derivative are recognized as the most important heterocyclic compounds. This series of compounds is of particular interests. It has various kinds of pharmacological properties and has been included in many kinds of natural products and pharmaceutical agents. The broad spectrum of pharmacological activity in individual benzothiazole derivative enables it to serve as unique and valuable scaffolds for experimental drug design. It is already known that benzothiazole and its derivative has various biological applications including anticancer, antimicrobial, anticonvulsant, antiviral, antidiabetic, antipsychotic, antiinflammatory, analgesic, fungicidal and diuretic. Its derivatives also have many applications in polymer chemistry, dyes, drugs, and silver photography as well as rubber industry.
• Uses: It is an interesting carbonyl equivalent and reacts with aldehydes or ketones to generate α-hydroxy carbonyl compounds. Benzothiazole is used as a chemical intermediate in organic synthesis. It is a precursor of rubber accelerators and a component of cyanine dyes. It is also used as a flavoring substance. It is also used as a flavor, antimicrobial agent, and component of cyanine dyes. Its derivatives are used as rubber accelerators. Various benzothiazole-benzamides synthesized were evaluated for their analgesic and antidepressant activities.

Technology Process of Benzothiazole

There total 223 articles about Benzothiazole 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: 80.0%

Benzothiazol-2-yl-triphenyl-phosphonium; chloride (79462-52-5) → 1,3-Benzothiazole (95-16-9) + Triphenylphosphine oxide (791-28-6)

Guidance literature:

With water; In acetonitrile;

Reference yield: 77.0%

5-(2-Amino-phenylsulfanylmethylene)-2,2-dimethyl-[1,3]dioxane-4,6-dione (188601-34-5) → 1,3-Benzothiazole (95-16-9) + Ketene (463-51-4)

Guidance literature:

at 550 ℃;

DOI:10.1080/00397919708006050

Reference yield: 75.0%

1-Benzothiazol-2-yl-1,2-diphenyl-ethanol → phenyl benzyl ketone (451-40-1) + 1,3-Benzothiazole (95-16-9)

Guidance literature:

With potassium cyanide; In N,N-dimethyl-formamide; at 120 ℃; for 2h;

DOI:10.1248/cpb.46.199

upstream raw materials:

1,3,5-Triazine

2-amino-benzenethiol

2-chlorobenzo[d][1,3]thiazole

2-thioxo-3H-1,3-benzothiazole

Downstream raw materials:

4-Benzothiazolyl-(2)-pyrimidin

2,3-dihydro-2-(1,1-dimethylethyl)benzothiazole

2-(tert-butyl)benzo[d]thiazole

bis(1,3-benzothiazol-2-yl)methanone

Refernces

• 1、 Kollenz, Gert,Seidler, Peter. "Mechanistic Investigations with the Aid of Isotopic Labeling, IX. Mechanism of the Ring Contraction Reaction of 1,4-Benzthiazin-2,3-4H-dione". . p. 623 - 628. Retrieved 1984.
• 2、 Capaldo, Luca,Quadri, Lorenzo L.,Merli, Daniele,Ravelli, Davide. "Photoelectrochemical cross-dehydrogenative coupling of benzothiazoles with strong aliphatic C-H bonds". supporting information. p. 4424 - 4427. Retrieved 2021/05/10.
• 3、 Zále?ák, Franti?ek,Ková?, Ond?ej,Lachetová, Eli?ka,?t'astná, Nikola,Pospí?il, Ji?í. "Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides". . p. 11291 - 11309. Retrieved 2021/09/07.