15647-75-3

Basic information

• Product Name: 2-(heptylsulfanyl)-1,3-benzothiazole
• Synonyms: 2-(Heptylsulfanyl)-1,3-benzothiazole; benzothiazole, 2-(heptylthio)-
• CAS NO: 15647-75-3
• Molecular Formula: C₁₄H₁₉NS₂
• Molecular Weight: 265.4374
• Mol File: 15647-75-3.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 381.9°C at 760 mmHg
• Flash Point: 184.8°C
• Density: 1.12g/cm³
• Vapor Pressure: 1.08E-05mmHg at 25°C
• Refractive Index: 1.599
• CAS DataBase Reference: 2-(heptylsulfanyl)-1,3-benzothiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(heptylsulfanyl)-1,3-benzothiazole(15647-75-3)
• EPA Substance Registry System: 2-(heptylsulfanyl)-1,3-benzothiazole(15647-75-3)

Safety Data

• Hazardous Substances Data: 15647-75-3(Hazardous Substances Data)

Usage

Chemical Class

2-(heptylsulfanyl)-1,3-benzothiazole belongs to the class of benzothiazole derivatives.

Usage

It is used as a corrosion inhibitor and as an intermediate in the production of pharmaceuticals and agrochemicals.

Synthesis

It is used in the synthesis of rubber accelerators, dyes, and optical brighteners.

Molecular Structure

It has a seven-carbon heptyl chain attached to a sulfur atom, which gives it its unique properties and reactivity.

Industrial and Commercial Applications

2-(heptylsulfanyl)-1,3-benzothiazole has potential industrial and commercial applications due to its versatile and valuable properties.

Upstream product

• 629-04-9 1-Bromoheptane 
• 149-30-4 2-Mercaptobenzothiazole 
• 615-22-5 2-methylmercaptobenzothiazole 
• 638-45-9 1-Iodohexane 

Downstream Products

• 54798-95-7 2-butyl-benzothiazole 
• 1639-09-4 heptanethiol 
• 1271300-81-2 2-(benzo[d]thiazol-2-ylsulfonyl)-1-cyclohexyloctan-1-one 
• 1271300-83-4 2-(benzo[d]thiazol-2-ylsulfonyl)-1-mesityloctan-1-one 
• 1271300-85-6 3-(benzo[d]thiazol-2-ylsulfonyl)-1-phenoxynonan-2-one 

Relevant articles and documents

Identification of novel ROS inducers: Quinone derivatives tethered to long hydrocarbon chains

We performed the first synthesis of the 17-carbon chain-tethered quinone moiety 22 (SAN5201) of irisferin A, a natural product exhibiting anticancer activity, and its derivatives. We found that 22 is a potent ROS inducer and cytotoxic agent. Compound 25 (SAN7401), the hydroquinone form of 22, induced a significant release of intracellular ROS and apoptosis (EC50 = 1.3-2.6 μM) in cancer cell lines, including A549 and HCT-116. Compared with the activity of a well-known ROS inducer, piperlongumine, 22 and 25 showed stronger cytotoxicity and higher selectivity over noncancerous cells. Another hydroquinone tethering 12-carbon chain, 26 (SAN4601), generated reduced levels of ROS but showed more potent cytotoxicity (EC50 = 0.8-1.6 μM) in cancer cells, although it lacked selectivity over noncancerous cells, implying that the naturally occurring 17-carbon chain is also crucial for ROS production and a selective anticancer effect. Both 25 and 26 displayed strong, equipotent activities against vemurafenib-resistant SK-Mel2 melanoma cells and p53-deficient H1299 lung cancer cells as well, demonstrating their broad therapeutic potential as anticancer agents.

Practical synthesis of β-acyl and β-alkoxycarbonyl heterocyclic sulfones

A short and efficient synthesis for β-acyl and β-alkoxycarbonyl heterocyclic sulfones containing benzothiazol (BT) and phenyltetrazol (PT) heterocyclic core is presented here. The method seems to be general and provides the desired C-nucleophiles in very good to excellent yields from readily available starting materials.