73953-89-6

Basic information

• Product Name: 1-BENZYL-1,2,3-TRIAZOLE-4,5-DICARBOXYLIC ACID
• Synonyms: TIMTEC-BB SBB008182;1-BENZYL-1,2,3-TRIAZOLE-4,5-DICARBOXYLIC ACID;1-benzyl-v-triazole-5-dicarboxylicacid
• CAS NO: 73953-89-6
• Molecular Formula: C₁₁H₉N₃O₄
• Molecular Weight: 247.21
• Mol File: 73953-89-6.mol
• Article Data: 4

Chemical Properties

• Melting Point: 181-182°C
• Boiling Point: 558.5°C at 760 mmHg
• Flash Point: 291.6°C
• Appearance: /
• Density: 1.52±0.1 g/cm3(Predicted)
• Vapor Pressure: 2.6E-13mmHg at 25°C
• PKA: 2.95±0.50(Predicted)
• BRN: 29417
• CAS DataBase Reference: 1-BENZYL-1,2,3-TRIAZOLE-4,5-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BENZYL-1,2,3-TRIAZOLE-4,5-DICARBOXYLIC ACID(73953-89-6)
• EPA Substance Registry System: 1-BENZYL-1,2,3-TRIAZOLE-4,5-DICARBOXYLIC ACID(73953-89-6)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36
• RTECS: XZ4580000
• Hazardous Substances Data: 73953-89-6(Hazardous Substances Data)

Usage

General Description

1-Benzyl-1,2,3-Triazole-4,5-Dicarboxylic Acid is a synthetic organic compound that consists of a 1,2,3-triazole ring attached to a benzyl group and two carboxylic acid groups. As a derivative of triazole, it falls into a class of five-membered ring compounds that contain three nitrogen atoms and two carbon atoms in the ring. This chemical compound is used as a reactant in organic chemistry, particularly in the synthesis of other complex molecules. Its physical properties, such as solubility and melting point, as well as its reactivity, will vary based on its specific formulation and the presence of any additional functional groups.

InChI:InChI=1/C11H9N3O4/c15-10(16)8-9(11(17)18)14(13-12-8)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,15,16)(H,17,18)/p-2

Upstream product

• 73500-16-0 1-benzyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 
• 622-79-7 benzyl azide 
• 142-45-0 Acetylenedicarboxylic acid 
• 100-44-7 benzyl chloride 
• 501652-87-5 1-benzyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid diamide 

Downstream Products

• 1335130-16-9 1-benzyl-1,2,3-triazole-4,5-dicarboxylic acid diazide 
• 132972-94-2 1-benzyl-4,5-bis(5-phenyl-1,3,4-oxadiazol-2-yl)-1,2,3-triazole 
• 4546-95-6 1H-1,2,3-triazole-4,5-dicarboxylic acid 
• 4368-68-7 1-benzyl-1H-[1,2,3]triazole 
• 73500-16-0 1-benzyl-1H-[1,2,3]triazole-4,5-dicarboxylic acid dimethyl ester 

Relevant articles and documents

Boronic acid catalysis for mild and selective [3+2] dipolar cycloadditions to unsaturated carboxylic acids

Herein, the concept of boronic acid catalysis (BAC) for the activation of unsaturated carboxylic acids is applied in several classic dipolar [3 + 2] cycloadditions involving azides, nitrile oxides, and nitrones as partners. These cycloadditions can be used to produce pharmaceutically interesting, small heterocyclic products, such as triazoles, isoxazoles, and isoxazolidines. These cycloadducts are formed directly and include a free carboxylic acid functionality that can be employed for fur-ther transformations, thereby avoiding prior masking or functionalization. In all cases, BAC provides faster reactions, under milder conditions, with much improved product yields and regioselectivities. In some instances, such as triazole formation from the reaction of azides with 2-alkynoic acids, catalysis with ort/io- nitrophenylboronic acid circumvents the undesirable product decarboxylation observed when using thermal activation. By using NMR spectroscopic studies, the boronic acid catalyst was shown to provide activation by a LUMO-lowering effect in the unsaturated carboxylic acid, likely via a monoacylated hemiboronic ester intermediate.

Photochemical fragmentation of unsubstituted tetrazole, 1,2,3-Triazole, and 1,2,4-triazole: First matrix-spectroscopic identification of nitrilimine HCNNH

Equilibria between the tautomers of heterocyclic azoles like 1, 2, and 4 have been studied many times. We here show that the application of density functional methods in combination with matrix IR spectroscopy is a useful tool for determining which protomer is preferred in rare gas matrices and thus also can be assumed to dominate in the gas phase. Photolysis of tetrazole (4) in cryogenic matrices allows the IR-spectroscopic identification of a new CH2N2 isomer, the long sought-after nitrilimine HCNNH (6). Flash pyrolysis of 4 also yielded nitrilimine. Upon irradiation this species is converted to a second, previously unknown "isomer", an HCN/NH complex 13. Nitrilimine (6) can also be generated by photolyzing 1,2,3- (1) and 1,2,4-triazole (2) in Ar matrices. The complex photochemistry of all three heterocyclic precursor compounds was unveiled. Our findings were supported by isotopic substitution experiments and by high-level ab initio calculations. Moreover, the IR bands of iminocyanide HNCN were tentatively assigned. This radical has up to now not been observed in a matrix. VCH Verlagsgesellschaft mbH, 1996.