6789-99-7

Basic information

• Product Name: 4,5,6,7-tetrahydro-1H-benzotriazole
• Synonyms: 4,5,6,7-tetrahydro-1H-benzotriazole;1H-Benzotriazole, 4,5,6,7-tetrahydro-;TETRAHYDROBENZOTRIAZOLE;Einecs 229-858-6
• CAS NO: 6789-99-7
• Molecular Formula: C₆H₉N₃
• Molecular Weight: 123.15576
• EINECS: 229-858-6
• Mol File: 6789-99-7.mol

Chemical Properties

• Boiling Point: 298.6°C at 760 mmHg
• Flash Point: 145.2°C
• Appearance: /
• Density: 1.219g/cm³
• Vapor Pressure: 0.00223mmHg at 25°C
• Refractive Index: 1.58
• PKA: 9.7[at 20 ℃]
• Water Solubility: 18.4g/L at 20℃
• CAS DataBase Reference: 4,5,6,7-tetrahydro-1H-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 4,5,6,7-tetrahydro-1H-benzotriazole(6789-99-7)
• EPA Substance Registry System: 4,5,6,7-tetrahydro-1H-benzotriazole(6789-99-7)

Safety Data

• Hazardous Substances Data: 6789-99-7(Hazardous Substances Data)

Usage

Flammability and Explosibility

Notclassified

InChI:InChI=1/C6H9N3/c1-2-4-6-5(3-1)7-9-8-6/h1-4H2,(H,7,8,9)

Upstream product

• 108-94-1 cyclohexanone 
• 13273-33-1 2-(triphenylphosphoranylidene)cyclohexanone 
• 74581-96-7 (2-Methoxy-1-cyclohexen-1-yl)triphenylphosphonium-bromid 
• 1728-36-5 3-Brom-2-methoxy-1-cyclohexen 
• 74581-99-0 1-Acetyl-4,5,6,7-tetrahydro-1H-benzotriazol 

Relevant articles and documents

A Scalable Metal-, Azide-, and Halogen-Free Method for the Preparation of Triazoles

A scalable metal-, azide-, and halogen-free method for the synthesis of substituted 1,2,3-triazoles has been developed. The reaction proceeds through a 3-component coupling of α-ketoacetals, tosyl hydrazide, and a primary amine. The reaction shows outstanding functional-group tolerance with respect to both the α-ketoacetal and amine coupling partners, providing access to 4-, 1,4-, 1,5-, and 1,4,5-substituted triazoles in excellent yield. This robust method results in densely functionalised 1,2,3-triazoles that remain challenging to prepare by azide–alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can be scaled in either batch or flow reactors. Methods for the chemoselective reaction of either aliphatic amines or anilines are also described, revealing some of the potential of this novel and highly versatile transformation.

A single-step acid catalyzed reaction for rapid assembly of: NH -1,2,3-triazoles

NH-1,2,3-Triazole moieties are a part of the design of various biologically active compounds, pharmaceutical agents and functional materials. Unfortunately, the applications of this heterocycle are still underexplored due to the lack of a general synthetic protocol. Here we outline a novel, general and facile metal-free pathway that enables the direct synthesis of these heterocycles by combining readily accessible and abundant precursors such as enolizable ketones and NH4OAc with high levels of regioselectivity via an organocascade process. The developed chemistry has been successfully applied to the synthesis of several structurally diverse products, pharmaceutical agents and supramolecular receptors.

Reactions with Organophosphorus Compounds, XLV. A New Synthesis of (2-Oxocycloalkylidene)triphenylphosphoranes

The bromoenolethers 1, upon treatment with triphenylphosphorane in nitromethane, yield the cycloalkenylphosphonium salts 4, which on subsequent reaction with hydrochloric acid and sodium carbonate afford the (2-oxocycloalkylidene)phosphoranes 3.With methyl bromide the O-methyl derivatives 4 are reformed from compounds 3; with acetyl azide the condensed acyltriazoles 5 are obtained, which lead to the unsubstituted triazoles 6, when treated with KOH.Reaction of 3b with (SCN)2 yields the cycloheptene derivative 7b, which can be cyclized to the thiazole 8b.