95-16-9 Usage
Chemical Description
Different sources of media describe the Chemical Description of 95-16-9 differently. You can refer to the following data:
1. Benzothiazole is a heterocyclic compound containing a sulfur atom and a nitrogen atom in its ring structure.
2. Benzothiazole is a heterocyclic compound containing a benzene ring fused to a thiophene ring and a nitrogen atom.
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.
Chemical Properties
Different sources of media describe the Chemical Properties of 95-16-9 differently. You can refer to the following data:
1. yellow liquid with an unpleasant odour
2. Benzothiazole has a delicate, persistent, rose-like odor similar to that of quinoline.
Occurrence
Reported found in apricot, cooked asparagus, mozzarella cheese, skim milk powder, roasted beef, beer, malt
whiskey, coconut meat, fresh mango, cooked broccoli and kelp.
Uses
Different sources of media describe the Uses of 95-16-9 differently. You can refer to the following data:
1. 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.
2. Various benzothiazole-benzamides synthesized were evaluated for their analgesic and antidepressant activities.
Definition
ChEBI: An organic heterobicyclic compound that is a fusion product between benzene and thiazole. The parent of the class of benzothiazoles.
Preparation
By refluxing a mixture of zinc o-aminophenylsulfide and formic acid, followed by steam distillation of the alkalized reaction
mixture; by heating formanilid or dimethylaniline with sulfur; by oxidation of 2-mercaptobenzothiazole or of the corresponding
disulfide.
Aroma threshold values
Detection: 80 to 450 ppb
Taste threshold values
Taste characteristics at 3 ppm: meaty, vegetative, brown, cooked, beefy and coffee-like.
Synthesis Reference(s)
Journal of the American Chemical Society, 77, p. 6559, 1955 DOI: 10.1021/ja01629a041
General Description
Benzothiazole, a volatile sulfur-containing heterocyclic compound, is one of the key odorants of heated milk. It is also reported to occur as a flavor component of miso, coconut meat and cooked-beef.
Safety Profile
Poison by ingestion,intraperitoneal, intravenous, and possibly other routes.When heated to decomposition it emits very toxic fumesof SOx, CN??, and NOx.
References
Gupta, Akhilesh, and S. Rawat. "Synthesis and cyclization of benzothiazole." J. of Current Pharmaceutical Research 3.1 (2010): 13-25.
Keri, Rangappa S., et al. "A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry." European journal of medicinal chemistry 89 (2015): 207-251.
Khokra, Sukhbir L., et al. "Common methods to synthesize benzothiazole derivatives and their medicinal significance: a review." International Journal of Pharmaceutical Sciences and Research 2.6 (2011): 1356.
Check Digit Verification of cas no
The CAS Registry Mumber 95-16-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 5 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 95-16:
(4*9)+(3*5)+(2*1)+(1*6)=59
59 % 10 = 9
So 95-16-9 is a valid CAS Registry Number.
InChI:InChI=1/C7H5NS/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
95-16-9Relevant articles and documents
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Davis et al.
, p. 1919 (1962)
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Unified Approach to Benzo[ d]thiazol-2-yl-Sulfonamides
Zále?ák, Franti?ek,Ková?, Ond?ej,Lachetová, Eli?ka,?t'astná, Nikola,Pospí?il, Ji?í
supporting information, p. 11291 - 11309 (2021/09/07)
In this paper, we report a unified approach to N-substituted and N,N-disubstituted benzothiazole (BT) sulfonamides. Our approach to BT-sulfonamides starts from simple commercially available building blocks (benzo[d]thiazole-2-thiol and primary and secondary amines) that are connected via (a) a S oxidation/S-N coupling approach, (b) a S-N coupling/S-oxidation sequence, or via (c) a S-oxidation/S-F bond formation/SuFEx approach. The labile N-H bond in N-monoalkylated BT-sulfonamides (pKa (BTSO2N(H)Bn) = 3.34 ± 0.05) further allowed us to develop a simple weak base-promoted N-alkylation method and a stereoselective microwave-promoted Fukuyama-Mitsunobu reaction. N-Alkyl-N-aryl BT-sulfonamides were accessed with the help of the Chan-Lam coupling reaction. Developed methods were further used in stereo and chemoselective transformations of podophyllotoxin and several amino alcohols.
Synthetic Applications of a New Magnetic Mesoporous Nanocomposite Catalyst Fe3O4@MCM-41@NH-SO3H
Pourhasan-Kisomi, Reyhaneh,Shirini, Farhad,Golshekan, Mostafa
, p. 166 - 175 (2021/04/09)
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Reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to synthesize 1H-benzoimidazole derivatives
Han, Limin,Hong, Hailong,Li, Xiao,Yang, Yue,Zhang, Junhua,Zhu, Ning
supporting information, (2021/09/28)
A simple and green protocol was developed for the reductive cyclization of o-phenylenediamine with CO2 and BH3NH3 to yield 1H-benzimidazole. The desired 1H-benzimidazole derivatives were produced under mild conditions. Mechanism investigation indicated that the coordination of o-phenylenediamine with the boron atom of BH3NH3 promoted the transfer of the formyl group to form a stable intermediate, which facilitated the intramolecular nucleophilic addition-elimination for the formation of target product. In this process, BH3NH3 served multifunctional roles, acting as a reducing agent and a formylation catalyst.
