46493-66-7

Basic information

• Product Name: 2(3H)-Benzothiazolimine, 3-phenyl-
• CAS NO: 46493-66-7
• Molecular Formula: C13H10N2S
• Molecular Weight: 226.302
• Mol File: 46493-66-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2(3H)-Benzothiazolimine, 3-phenyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 2(3H)-Benzothiazolimine, 3-phenyl-(46493-66-7)
• EPA Substance Registry System: 2(3H)-Benzothiazolimine, 3-phenyl-(46493-66-7)

Safety Data

• Hazardous Substances Data: 46493-66-7(Hazardous Substances Data)

Upstream product

• 4921-82-8 1-benzoyl-3-phenylthiourea 
• 34835-57-9 2-bromo benzene diazonium chloride 
• 3898-08-6 1,1-diphenylthiourea 
• 537-67-7 diphenylamine hydrochloride 

Downstream Products

• 54286-55-4 1,1'-diphenyl-3,3'-bis-(3-phenyl-3H-benzothiazol-2-ylidene)-1,1'-(2,2'-disulfanediyl-diphenyl)-bis-urea 
• 66179-90-6 bis-(3-phenyl-3H-benzothiazol-2-ylidene)-urea 
• 78072-96-5 2-methylimino-3-phenylbenzothiazoline 
• 41631-62-3 3-Phenyl-2(3H)-benzothiazolon 
• 66179-89-3 (3-phenyl-3H-benzothiazol-2-ylidene)-cyanamide 
• 38650-47-4 bromo-(3-phenyl-3H-benzothiazol-2-ylidene)-amine 
• 66221-73-6 tris-(3-phenyl-3H-benzothiazol-2-ylidene)-guanidinium; chloride 
• 66179-81-5 bis-(3-phenyl-benzothiazol-2-yl)-azamethinium; chloride 
• 16078-95-8 2-(phenylamino)-benzenethiol 
• 32954-79-3 (4-phenyl-benzo[f]quinolin-3-yl)-(3-phenyl-benzothiazol-2-yl)-methinium ; iodide 
• 52886-85-8 1,3-bis-(3-phenyl-benzothiazol-2-yl)-trimethinium ; iodide 

Relevant articles and documents

Theoretical investigations on the HOMO–LUMO gap and global reactivity descriptor studies, natural bond orbital, and nucleus-independent chemical shifts analyses of 3-phenylbenzo[d]thiazole-2(3H)-imine and its para-substituted derivatives: Solvent and subs

Natural bond orbital analysis, salvation, and substituent effects of electron-releasing (–CH3, –OH) and electron-withdrawing (–Cl, –NO2, –CF3) groups at para positions on the molecular structure of synthesized 3-phenylbenz

Experimental and theoretical studies on the thermal decomposition of heterocyclic nitrosimines

A series of substituted 2-nitrosiminobenzothiazolines (2) were synthesized by the nitrosation of the corresponding 2-iminobenzothiazolines (6). Thermal decomposition of 2a-f and of the seleno analogue 7 in methanol and of 3-methyl-2-nitrosobenzothiazoline (2a) in acetonitrile, 1,4-dioxane, and cyclohexane followed first-order kinetics. The activation parameters for thermal deazetization of 2a were measured in cyclohexane (ΔH? = 25.3 ± 0.5 kcal/mol, ΔS? = 1.3 ± 1.5 eu) and in methanol (ΔH? = 22.5 ± 0.7 kcal/mol, ΔS? = -12.9 ± 2.1 eu). These results indicate a unimolecular decomposition and are consistent with a proposed stepwise mechanism involving cyclization of the nitrosimine followed by loss of N2. The ground-state conformations of the parent nitrosiminothiazoline (9a) and transition states for rotation around the exocyclic C=N bond, electrocyclic ring closure, and loss of N2 were calculated using ab initio molecular orbital theory at the MP2/6-31G* level. The calculated gas-phase barrier height for the loss of N2 from 9a (25.2 kcal/mol, MP4(SDQ, FC)/6-31G*//MP2/6-31G* + ZPE) compares favorably with the experimental barrier for 2a of 25.3 kcal/mol in cyclohexane. The potential energy surface is unusual; the rotational transition state 9a-rot-ts connects directly to the orthogonal transition state for ring-closure 9aTS. The decoupling of rotational and pseudopericyclic bond-forming transition states is contrasted with the single pericyclic transition state (15TS) for the electrocyclic ring-opening of oxetene (15) to acrolein (16). For comparison, the calculated homolytic strength of the N-NO bond is 40.0 kcal/mol (MP4(SDQ, FC)/6-31G* + ZPE).