16681-82-6

Basic information

• Product Name: 1H-1,2,3-Triazole, 5-bromo-1-methyl-
• Synonyms: 5-bromo-1-methyl-1H-[1,2,3]triazole;5-Brom-1-methyl-1H-[1,2,3]triazol
• CAS NO: 16681-82-6
• Molecular Formula: C3H4BrN3
• Molecular Weight: 161.989
• Mol File: 16681-82-6.mol

Chemical Properties

• CAS DataBase Reference: 1H-1,2,3-Triazole, 5-bromo-1-methyl-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3-Triazole, 5-bromo-1-methyl-(16681-82-6)
• EPA Substance Registry System: 1H-1,2,3-Triazole, 5-bromo-1-methyl-(16681-82-6)

Safety Data

• Hazardous Substances Data: 16681-82-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1H-1,2,3-Triazole, 5-bromo-1-methylis used as a key intermediate in the synthesis of pharmaceutical compounds for its unique structure and properties. It contributes to the development of new drugs with potential therapeutic applications.
Used in Agrochemical Industry:
1H-1,2,3-Triazole, 5-bromo-1-methylis utilized as a building block in the synthesis of agrochemicals, such as pesticides and herbicides, due to its ability to enhance the effectiveness and selectivity of these chemicals.
Used in Materials Science:
1H-1,2,3-Triazole, 5-bromo-1-methylis employed in the development of advanced materials with specific properties, such as conductivity, magnetism, or catalytic activity, owing to its versatile chemical structure.
Used in Organic Synthesis:
As a brominated derivative of 1-methyl-1H-1,2,3-triazole, 1H-1,2,3-Triazole, 5-bromo-1-methyl- serves as a valuable synthetic building block in organic synthesis, enabling the creation of a wide range of organic compounds with diverse applications.
Overall, 1H-1,2,3-Triazole, 5-bromo-1-methylis a promising compound with potential applications across various industries, including pharmaceuticals, agrochemicals, materials science, and organic synthesis, due to its unique structure and properties.

Synthetic route

Toluene-4-sulfonate5-bromo-3-(3-bromo-4-methoxy-benzyl)-1-methyl-3H-[1,2,3]triazol-1-ium; → 5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6)

Conditions	Yield
With sulfuric acid at 120℃; for 1h;	57%

diazomethane (186581-53-3, 908094-01-9) + diethyl ether (60-29-7) + bromocyane (506-68-3) → 4-bromo-1-methyl-1H-1,2,3-triazole (13273-53-5) + 4-bromo-2-methyl-2H-1,2,3-triazole (16681-67-7) + 5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) + cyanomethyl bromide (590-17-0)

1-methyl-1,2,3-triazole (16681-65-5) → 5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6)

Conditions	Yield
With n-butyllithium; bromine 1.) hexane, THF, -40 deg C, 1 h, 2.) hexane, THF, RT, 2 h; Yield given. Multistep reaction;

diazomethane (186581-53-3, 908094-01-9) + bromocyane (506-68-3) → 5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) + 4-bromo-2-methyl-2H-<1,2,3>triazole and 4-bromo-1-methyl-1H-<1,2,3>triazole

Conditions	Yield
With diethyl ether

5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) + methyl 4-ethyl-3-(N-(2-(piperidin-1-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)sulfamoyl)benzoate → methyl 4-ethyl-3-(N-(5-(1-methyl-1,2,3-triazol-5-yl)-2-(piperidin-1-yl)phenyl)sulfamoyl)benzoate

Conditions	Yield
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere;	85%

5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) + (S)-(7-(methylsulfonyl)-5-(phenyl(tetrahydro-2H-pyran-4-yl)methyl)-5H-pyrido[3,2-b]indol-3-yl)boronic acid → 5-{7-methanesulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2-b]indol-3-yl}-1-methyl-1H-1,2,3-triazole

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sonication; Sealed tube;	18%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 100℃; for 1h; Suzuki Coupling; Inert atmosphere; Sonication;

5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) + aniline (62-53-3) → (3-methyl-3H-[1,2,3]triazol-4-yl)-phenyl-amine (103262-65-3)

5-bromo-1-methyl-1H-1,2,3-triazole (16681-82-6) → 3-methyl-3H-[1,2,3]triazol-4-ylamine (24660-67-1)

Conditions	Yield
With ethanol; ammonia

Upstream product

• 186581-53-3 diazomethane 
• 506-68-3 bromocyane 
• 16681-65-5 1-methyl-1,2,3-triazole 
• 60-29-7 diethyl ether 

Downstream Products

• 24660-67-1 3-methyl-3H-[1,2,3]triazol-4-ylamine 
• 103262-65-3 (3-methyl-3H-[1,2,3]triazol-4-yl)-phenyl-amine 

Relevant articles and documents

Alkylation and acylation of the 1,2,3,triazole ring

Trimethylsilylation of 1,2,3-triazole regioselectively proceeded to give 2-trimethylsilyl-2H-1,2,3-triazole, which was treated with primary alkyl halides in the presence of tetrabutylammonium fluoride to give 1-alkyl-1H- 1,2,3-triazoles as a Sole product 1-Methyl-5-substituted 1H-1,2,3-triazoles were prepared by alkylation of 5-lithio-1-methyl-1H-1,2,3-triazole, and 1- methyl-4-substituted 1H-1,2,3-triazoles were obtained by alkylation of 4- lithio-1-methyl-5-phenylthio-1H-1,2,3-triazole followed by reductive desulfurization.

INTRODUCTION OF SUBSTITUENTS INTO 5-MEMBERED AZA-HETEROAROMATICS

With emphasis on mono- and regio-selectively, methods for introduction of substituents at nitrogen and carbon atoms of 5-membered aza-heteroaromatics have been developed.The methods involve application of activation and of assistant groups for direction and protection.Activation has been achieved by the use of quaternary azolium ions and azol-N-oxides as reactive intermediates.If necessary, the N-oxides were further activated by alkylation or acylation.