254-87-5

Basic information

• Product Name: 1,2,4-Benzotriazene
• Synonyms: 1,2,4-benzotriazine
• CAS NO: 254-87-5
• Molecular Formula: C₇H₅N₃
• Molecular Weight: 131.1347
• EINECS: 205-967-4
• Mol File: 254-87-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 238.4°C at 760 mmHg
• Flash Point: 105.6°C
• Density: 1.27g/cm³
• Vapor Pressure: 0.0656mmHg at 25°C
• Refractive Index: 1.665
• CAS DataBase Reference: 1,2,4-Benzotriazene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2,4-Benzotriazene(254-87-5)
• EPA Substance Registry System: 1,2,4-Benzotriazene(254-87-5)

Safety Data

• Hazardous Substances Data: 254-87-5(Hazardous Substances Data)

Usage

Description

1,2,4-Benzotriazene, with the molecular formula C6H5N3, is a colorless, crystalline solid that serves as a key intermediate in the synthesis of dyes, pigments, and other organic compounds. Despite its utility in chemical production, it is recognized as a potent carcinogen and mutagen, posing significant health risks due to its potential to cause cancer and genetic mutations in living organisms. As a result, its use is strictly regulated and controlled in many countries to mitigate exposure and ensure safety.

Uses

Used in Chemical Production Industry:
1,2,4-Benzotriazene is used as a chemical intermediate for the production of dyes and pigments, contributing to the coloration and enhancement of various materials. Its role in this industry is crucial for the development of a wide range of colorants used in different applications, including textiles, plastics, and printing inks.
However, due to its hazardous nature, the use of 1,2,4-Benzotriazene in chemical production must be carefully managed with stringent safety protocols to prevent exposure and protect the health of workers and the environment. This includes implementing appropriate containment measures, personal protective equipment, and disposal methods to minimize the risk of carcinogenic and mutagenic effects associated with this compound.

Upstream product

• 64241-51-6 benzo[e][1,2,4]triazine-3-carboxylic acid 
• 1885-34-3 N,N'-diphenylformazan 
• 6299-89-4 N-Formyl-N'-(o-aminophenyl)hydrazine 
• 60702-35-4 N-Formyl-N'-(o-nitrophenyl)hydrazine 
• 6165-66-8 1,5-diphenyl-formazan-3-carboxylic acid ethyl ester 
• 75122-01-9 3-methylsulfanyl-1,2,4-benzotriazine 
• 37522-26-2 ethyl [(2-nitrophenyl)hydrazono](chloro)acetate 
• 20954-18-1 2-[(2-Nitro-phenyl)-hydrazono]-3-oxo-butyric acid ethyl ester 
• 91669-21-5 3-chlorobenzo[e][1,2,4]triazine 
• 1493-27-2 ortho-nitrofluorobenzene 
• 59323-44-3 benzo[e][1,2,4]triazine-1-oxide 
• 110181-37-8 bromo-(2-nitro-phenylhydrazono)-acetic acid ethyl ester 
• 114098-35-0 amino-(2-nitro-phenylhydrazono)-acetic acid ethyl ester 
• 99185-60-1 ethyl benzo[e][1,2,4]triazine-3-carboxylate 

Downstream Products

• 95-14-7 1,2,3-Benzotriazole 
• 59323-44-3 benzo[e][1,2,4]triazine-1-oxide 

Relevant articles and documents

3-Substituted Benzo[ e][1,2,4]triazines: Synthesis and Electronic Effects of the C(3) Substituent

A series of 19 structurally diverse C(3)-substituted derivatives of benzo[e][1,2,4]triazine were synthesized from 3-chloro- (1c) and 3-iodobenzo[e][1,2,4]triazine (1d) obtained in three steps from 2-nitroaniline in 37-55% yields. Nucleophilic aromatic substitution and metal-catalyzed (Pd, Cu) reactions led to functional derivatives that include alkyl (C5H11), (het)aryl (Ph, 2-thienyl, ferrocenyl), ArCC, amine (NHPh and morpholine), PO(OEt)2, sulfanyl (SBu-t), alkoxide (OEt, OMe), and CN. The synthesis of C(3)-CF3 derivative 1g via the Ruppert reaction with 1d and its 1-oxide analogue 2d led to the substitution followed by formal addition of HCF3 to the C?N bond. Pd-catalyzed carbonylation reactions of 1d and 2d did not give the corresponding C(3)-carboxylic acids. Therefore, acid 1f was obtained through hydrolysis of the CN. The substituent effect on the electronic structure of the benzo[e][1,2,4]triazine ring was investigated by spectroscopic methods (UV-vis and NMR) augmented with density functional theory calculations. Results show significant effect of the C(3) substituent on the (1) transition energy and good correlation of the 1H NMR chemical shift with the substituent constant σp. Molecular and crystal structures of six derivatives were established with the single-crystal X-ray diffraction method, and the substituent impact on the molecular geometry was investigated.

Complete 1H, 13C and 15N NMR assignment of tirapazamine and related 1,2,4-benzotriazine N-oxides

1H, 13C and 15N NMR measurements (1D and 2D including 1H-15N gs-HMBC) have been carried out on 3-amino-1, 2,4-benzotriazine and a series of N-oxides and complete assignments established. N-Oxidation at any position resulted in large upfield shifts of the corresponding N-1 and N-2 resonances and downfield shifts for N-4 with the exception of the 3-amino-1,2,4-benzotriazine 1-oxide in which a small upfield shift of N-4 was observed. Density functional GIAO calculations of the 15N and 13C chemical shifts [B3LYP/6-31G(d)//B3LYP/6- 311+G(2d,p)] gave good agreement with experimental values confirming the assignments. The combination of 13C and 15N NMR provides an unambiguous method for assigning the 1H and 13C resonances of N-oxides of 1,2,4-benzotriazines. Copyright

Process for preparing 1,2,4-benzotriazine oxides

A method of using 1,2,4-benzotriazine oxides, some of which are novel compounds, as radiosensitizers and selective cytotoxic agents is disclosed. These compounds are shown to specifically radiosensitize hypoxic tumor cells. Some are additionally disclosed to be useful as specific cytotoxic agents for these cells. They also show an unexpected ability to radiosensitize aerobic cells following or preceding a hypoxic incubation of the cells with the drug. This provides a basis for selective radiosensitization of tumors compared to normal cells. A novel method for preparing the 1,2,4-benzotriazine oxides is also disclosed.