74731-63-8

Basic information

• Product Name: 1H-1,2,3 TRIAZOLE-1-ETHANOL
• Synonyms: 1H-1,2,3 TRIAZOLE-1-ETHANOL;2-(1H-1,2,3-triazol-1-yl)ethanol
• CAS NO: 74731-63-8
• Molecular Formula: C4H7N3O
• Molecular Weight: 113.12
• Mol File: 74731-63-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 270.981 °C at 760 mmHg
• Flash Point: 117.685 °C
• Appearance: /
• Density: 1.322 g/cm³
• Vapor Pressure: 0.003mmHg at 25°C
• Refractive Index: 1.602
• PKA: 13.77±0.10(Predicted)
• CAS DataBase Reference: 1H-1,2,3 TRIAZOLE-1-ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-1,2,3 TRIAZOLE-1-ETHANOL(74731-63-8)
• EPA Substance Registry System: 1H-1,2,3 TRIAZOLE-1-ETHANOL(74731-63-8)

Safety Data

• Hazardous Substances Data: 74731-63-8(Hazardous Substances Data)

Usage

Uses

1H-1,2,3 Triazole-1-ethanol is used as a corrosion inhibitor; abrasive material for flatting metal layers,

InChI:InChI=1/C4H7N3O/c8-4-3-7-2-1-5-6-7/h1-2,8H,3-4H2

Synthetic route

2-azidoethanol (1517-05-1) + acetylene (74-86-2) → 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8)

Conditions	Yield
at 110 - 120℃; under 9120 - 10640 Torr;	95%

1-(β-hydroxyethyl)-1,2,3-triazole-4-carboxylic acid (74731-49-0) → 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8)

Conditions	Yield
under 5 - 10 Torr; Heating;	64.2%

1,2,3-triazole (288-36-8) + 1-bromoethanol (141072-57-3) → 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8)

Conditions	Yield
In ethanol

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + 7-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (193002-25-4) → 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (220896-22-0)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 2h;	97%
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 1h; Etherification;

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + 7-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (193002-25-4) + diethylazodicarboxylate (1972-28-7) → 6-methoxy-3-((pivaloyloxy)methyl)-7-(2-(1,2,3-triazol-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (220896-22-0)

Conditions	Yield
With triphenylphosphine In dichloromethane	97%

2-chloro-5-nitropyridine (4548-45-2) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 2-(2-(1H-1,2,3-triazol-1-yl)ethoxy)-5-nitropyridine

Conditions	Yield
Stage #1: 2-chloro-5-nitropyridine With sodium hydride In tetrahydrofuran at 0℃; for 0.166667h; Stage #2: 2-(1,2,3-triazol-1-yl)-ethan-1-ol In tetrahydrofuran at 0℃; for 2h;	90%

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + p-toluenesulfonyl chloride (98-59-9) → 2-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate (263400-92-6)

Conditions	Yield
With dmap; triethylamine In dichloromethane at -10 - -4℃;	86%
With dmap; triethylamine In dichloromethane at -4℃;	86%
With dmap; triethylamine In dichloromethane at -10 - -4℃;	86%
Stage #1: 2-(1,2,3-triazol-1-yl)-ethan-1-ol; p-toluenesulfonyl chloride With dmap; triethylamine In dichloromethane; water at -10 - -4℃; for 0.166667h; Stage #2: With hydrogenchloride In dichloromethane; water Stage #3: With sodium hydrogencarbonate In dichloromethane; water	86%
With triethylamine; dmap In dichloromethane at -10 - -4℃;	86%

allyl-(4-chloromethyl-2-methyl-phenyl)-ether (58013-41-5) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 1-[2-(4-allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole (865350-63-6)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 5h;	86%

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + acrylonitrile (107-13-1) → 2-(4'-cyano-2'-oxa-1'-butyl)-1,2,3-triazole + 2-(5'-cyano-3'-oxa-1-pentyl)-1,2,3-triazole (84440-24-4)

Conditions	Yield
With potassium hydroxide In water at 25 - 35℃; for 7h;	A 25% B 78%

4-allyloxybenzyl chloride (32078-38-9) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 1-[2-(4-allyloxy-benzyloxy)-ethyl]-1H-[1,2,3]-triazole (864156-90-1)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at -50 - 20℃;	78%
With sodium hydride In DMF (N,N-dimethyl-formamide) at -50 - 20℃;	78%
With sodium hydride In N,N-dimethyl-formamide at -50 - 20℃;	78%
With sodium hydride In N,N-dimethyl-formamide at -50 - 20℃;	78%
With sodium hydride In N,N-dimethyl-formamide at -50 - 20℃;	78%

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → N-vinyl-1,2,3-triazole (41917-22-0) + 1-(3-oxa-4-pentenyl)-1,2,3-triazole (59282-97-2)

Conditions	Yield
With potassium hydroxide; acetylene In 1,4-dioxane at 175 - 180℃; under 7600 - 9120 Torr; for 1.5h;	A 5.5% B 33.5%

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + acetylene (74-86-2) → N-vinyl-1,2,3-triazole (41917-22-0) + 1-(3-oxa-4-pentenyl)-1,2,3-triazole (59282-97-2)

Conditions	Yield
With potassium hydroxide In 1,4-dioxane at 175 - 180℃; under 7600 - 9120 Torr; for 1.5h;	A 5.5% B 33.5%

4-chloro-6-cyano-7-hydroxyquinoline (352205-91-5) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + diethylazodicarboxylate (1972-28-7) → 4-chloro-6-cyano-7-(2-(1,2,3-triazol-1-yl)ethoxy)quinoline (398487-34-8)

Conditions	Yield
With triphenylphosphine In dichloromethane	32%

4-nitrobenzyl iodide (3145-86-6) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 1-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole (791629-24-8)

Conditions	Yield
Stage #1: 2-(1,2,3-triazol-1-yl)-ethan-1-ol With sodium hydride In tetrahydrofuran at -50℃; for 0.75h; Stage #2: 4-nitrobenzyl iodide In tetrahydrofuran for 2h; Heating / reflux;	27%

-butyl vinyl ether (111-34-2) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 1-(3-oxa-4-pentenyl)-1,2,3-triazole (59282-97-2)

Conditions	Yield
With mercury(II) diacetate at 95 - 100℃; for 2h;	6.35%

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + 4-(4-bromo-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline (196603-96-0) → N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[2-(1H-1,2,3-triazol-1-yl)ethoxy]quinazoline-4-amine

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 2h; Etherification;

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + 4-(4-chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline (193001-59-1) → (4-chloro-2-fluoro-phenyl)-[6-methoxy-7-(2-[1,2,3]triazol-1-yl-ethoxy)-quinazolin-4-yl]-amine

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 3h; Etherification;

2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) + N-(4-bromo-2,6-difluorophenyl)-7-hydroxy-6-methoxy-4-quinazolinylamine (257938-40-2) → (4-bromo-2,6-difluoro-phenyl)-[6-methoxy-7-(2-[1,2,3]triazol-1-yl-ethoxy)-quinazolin-4-yl]-amine

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In dichloromethane at 20℃; for 2h; Etherification;

5-(6-(azidocarbonyl)-5-isopropylpyrrolo[2,1-f][1,2,4]triazin-4-ylamino)-2,4-difluoro-N-methoxybenzamide (658085-52-0) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → [4-(2,4-difluoro-5-methoxycarbamoyl-phenylamino)-5-isopropyl-pyrrolo[2,1-f][1,2,4]triazin-6-yl]-carbamic acid 2-[1,2,3]triazol-1-yl-ethyl ester

Conditions	Yield
In N,N-dimethyl-formamide at 85℃; for 2h; Curtius rearrangement;

6-hydroxyquinoline (580-16-5) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 6-[2-(1H-1,2,3-triazol-1-yl)ethoxy]quinoline (476660-01-2)

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran

1-allyloxy-3-fluoro-4-chloromethyl-benzene (865350-66-9) + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → 1-[2-(4-allyloxy-2-fluoro-benzyloxy)-ethyl]-1H-[1,2,3]triazole (865350-67-0)

Conditions	Yield
With sodium hydride In DMF (N,N-dimethyl-formamide) at -50 - 20℃;

C33H46N8O7PPol + 2-(1,2,3-triazol-1-yl)-ethan-1-ol (74731-63-8) → C31H38N10O8PPol

Conditions	Yield
With benzotriazol-1-ol In N,N-dimethyl-formamide; acetonitrile at 20℃; for 65h; polystyrene resin;

Upstream product

• 1517-05-1 2-azidoethanol 
• 74-86-2 acetylene 
• 141-43-5 ethanolamine 
• 74731-49-0 1-(β-hydroxyethyl)-1,2,3-triazole-4-carboxylic acid 
• 288-36-8 1,2,3-triazole 
• 141072-57-3 1-bromoethanol 

Downstream Products

• 263400-92-6 2-(1H-1,2,3-triazol-1-yl)ethyl 4-methyl-1-benzenesulfonate 
• 865350-63-6 1-[2-(4-allyloxy-2-methyl-benzyloxy)-ethyl]-1H-[1,2,3]triazole 
• 865350-67-0 1-[2-(4-allyloxy-2-fluoro-benzyloxy)-ethyl]-1H-[1,2,3]triazole 
• 791629-24-8 1-[2-(4-nitro-benzyloxy)-ethyl]-1H-[1,2,3]triazole 
• 864156-90-1 1-[2-(4-allyloxy-benzyloxy)-ethyl]-1H-[1,2,3]-triazole 
• 413599-62-9 N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[2-(1H-1,2,3-triazol-1-yl)ethoxy]quinazoline-4-amine 

Relevant articles and documents

[4 + 1] Annulation of in situ generated azoalkenes with amines: A powerful approach to access 1-substituted 1,2,3-triazoles

1-Substituted 1,2,3-triazoles represents ‘privileged’ structural scaffolds of many clinical pharmaceuticals. However, the traditional methods for their preparation mainly rely on thermal [3 + 2] cycloaddition of potentially dangerous acetylene and azides. Here we report a base-mediated [4 + 1] annulation of azoalkenes generated in situ from readily available difluoroacetaldehyde N-tosylhydrazones (DFHZ-Ts) with amines under relatively mild conditions. This azide- and acetylene-free strategy provides facile access to diverse 1-substituted 1,2,3-triazole derivatives in high yield in a regiospecific manner. This transformation has great functional group tolerance and can suit a broad substrate scope. Furthermore, the application of this novel methodology in the gram-scale synthesis of an antibiotic drug PH-027 and in the late-stage derivatization of several bioactive small molecules and clinical drugs demonstrated its generality, practicability and applicability.

Substituted anilino-quinazoline (or quinoline) compounds and use thereof

The invention concerns amide derivatives of Formula (I), wherein: G is N or CH; R1is a group such as hydroxy, halo, trifluoromethyl, C1-6alkyl and C1-6alkoxy; each of R2and R3is hydrogen, halo, C1-6alkyl, C2-6alkenyl or C2-6alkynyl; R4is a group such as hydrogen, hydroxy, C1-6alkyl, C1-6alkoxy and C3-7cycloalkyl, or R4is of the Formula (IC): —K—J, wherein J is aryl, heteroaryl or heterocyclyl and K is a bond or a group such as oxy and imino, R5is a group such as hydrogen, halo and trifluoromethyl: m is 1-3 and q is 0-4; or pharmaceutically acceptable salts or in vivo cleavable esters thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.

UNSATURATED CARBONYL-CONTAINING COMPOUNDS. XXVIII. CYCLOADDITION OF ORGANIC AZIDES TO α-ACETYLENIC KETONES AND ACIDS

The reaction of α-acetylenic ketones and acids with organic azides leads to the formation of 1-alkyl(aryl)-4-acyl(carboxy)-1,2,3-triazoles or to a mixture of the 1,4- and 1,5-disubstituted isomers.The effect of the structure of the initial compound and of the solvent on the direction of cycloaddition was investigated.