Name: 1,2,4-Triazole | s-Triazole; Pyrrodiazole
Brand: Ambeed
SKU: A234123
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Synonyms: s-Triazole; Pyrrodiazole

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Quality Control of 1,2,4-Triazole Purity: 97% SDS Specification

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Product Details of 1,2,4-Triazole

CAS No. :	288-88-0
Formula :	C₂H₃N₃
M.W :	69.07
SMILES Code :	N1N=CN=C1
Synonyms :	s-Triazole; Pyrrodiazole
MDL No. :	MFCD00005228
InChI Key :	NSPMIYGKQJPBQR-UHFFFAOYSA-N
Pubchem ID :	9257

Safety of 1,2,4-Triazole

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H313-H319-H360-H402
Precautionary Statements:	P201-P202-P264-P270-P273-P280-P301+P312+P330-P305+P351+P338-P312-P337+P313-P405-P501

Application In Synthesis of 1,2,4-Triazole

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 288-88-0 ]
Downstream synthetic route of [ 288-88-0 ]

[ 288-88-0 ] Synthesis Path-Upstream 1~6

1
[ 288-88-0 ]
[ 74-88-4 ]
[ 6086-21-1 ]
[ 10570-40-8 ]

References: [1] Bulletin des Societes Chimiques Belges, 1988, vol. 97, # 8-9, p. 573 - 598.
[2] Tetrahedron Letters, 2000, vol. 41, # 8, p. 1297 - 1301.
[3] Acta Chemica Scandinavica, 1990, vol. 44, # 10, p. 1050 - 1057.

2
[ 288-88-0 ]
[ 616-38-6 ]
[ 10570-40-8 ]

Yield	Reaction Conditions	Operation in experiment
4.74 g	at 120℃; for 16 h; Inert atmosphere	Step 1. 250 mmol of dimethyl carbonate was added to a mixture of 50 mmol of 1,2,4-triazole and 12.5 mmol of sodium carbonate, and the resulting suspension was stirred at 120 ° C under a nitrogen atmosphere and refluxed for 16 h. Volatilization in the residual liquid in the vacuumWashing the residue with chloroform, filtering solid impurities, and spinning the filtrate.4.74 g of 4-methyl-1,2,4-triazole was obtained as a colorless liquid.

References: [1] Patent: CN108250227, 2018, A, . Location in patent: Paragraph 0025; 0028.

3
[ 288-88-0 ]
[ 74-88-4 ]
[ 10570-40-8 ]

References: [1] Organic Letters, 2010, vol. 12, # 13, p. 3002 - 3005.

4
[ 288-88-0 ]
[ 77-78-1 ]
[ 6086-21-1 ]
[ 10570-40-8 ]

References: [1] Acta Chemica Scandinavica, 1990, vol. 44, # 10, p. 1050 - 1057.

5
[ 21034-55-9 ]
[ 74-88-4 ]
[ 288-88-0 ]
[ 6086-21-1 ]
[ 10570-40-8 ]

References: [1] Russian Journal of Organic Chemistry, 1995, vol. 31, # 8, p. 1118 - 1121[2] Zhurnal Organicheskoi Khimii, 1995, vol. 31, # 8, p. 1227 - 1230.

6
[ 288-88-0 ]
[ 616-38-6 ]
[ 6086-21-1 ]
[ 10570-40-8 ]

References: [1] Organometallics, 2012, vol. 31, # 12, p. 4565 - 4573.

[ 288-88-0 ] Synthesis Path-Downstream 1~56

1
[ 288-88-0 ]
[ 74-88-4 ]
[ 6086-21-1 ]

Yield	Reaction Conditions	Operation in experiment
10.5 g (58%)	With sodium methylate; sodium; In methanol; dichloromethane; chloroform;	(a) To a stirred solution of sodium methoxide (from 5 g of sodium, 0.218 mol) in 120 ml of methanol under argon was added 1,2,4-triazole (15 g, 0.217 mol) at 0° C. and then 30.9 g (0.217 mol) of methyl iodide, and the mixture was stirred at room temperature for 24 h. The solvent was concencentrated in vacuo, the residue was extracted with 80 ml of hot benzene and then with chloroform (3*80 ml). Upon removal of the solvent in vacuo, 25.4 g of a white gum was isolated and the gum was dissolved in methylene chloride, filtered, and the filtrate was concentrated to yield an oil. The oil was distilled (80°-90° C./10-15 mm) to afford 10.5 g (58percent) of 1-methyl-1,2,4-triazole.
	With sodium methylate; In methanol; benzene;	Preparation 20-1) To a solution of 1,2,4-triazole (100 g) in methanol (200 ml) was added 28percent sodium methoxide in methanol solution (278.3 ml), followed by iodomethane (205.5 g) and the solution was warmed to 40° C. for 18 hours. The solution was concentrated in vacuo to remove methanol then treated with benzene (150 ml), warmed to 70° C. and decanted. This was repeated with 3*150 ml portions of chloroform. The combined organic layer was concentrated in vacuo to ca. 100 ml and the white precipitate was removed by filtration. After evaporation of the filtrate the resulting red liquid residue was distilled at atmospheric pressure to give 1-methyl-1,2,4-triazole (71.45 g) as a colorless liquid that solidified in the refrigerator. bp: 175°-180° C. IR (Neat): 3100, 2950 cm-1NMR (CDCl3, delta): 3.95 (3H, s), 7.94 (1H, s), 8.05 (1H, s)EI-Mass (m/z): 83 (M+)
	In tetrahydrofuran; methanol;	REFERENCE EXAMPLE 31 (S)2-Amino-4-methyl-(S)1-(1-methyl-1H-1,2,4-triazol-5-yl)-pentan-1-ol and (S)2-Amino-4-methyl-(R)1-(1-methyl-1H-1,2,4-triazol-5-yl)-pentan-1-ol To a suspension of 15.2 g of sodium hydride (60percent in oil) (washed with hexane) in 100 ml of tetrahydrofuran under argon was added slowly at 0° to 10° C. a solution of 25 g of 1,2,4-triazol in 100 ml of methanol. To this solution was added dropwise 25 ml of methyl iodide over 0.5 hour. The mixture was stirred at 0° C. for 1 hour and then refluxed for 15 minutes. The solution was concentrated under reduced pressure until sodium iodide began to precipitate. The mixture was diluted with 100 ml each of ether and dichloromethane, filtered and the filtrate concentrated to dryness. The residual solid was triturated with dichloromethane (100 ml) and filtered. The filtrate was dried over molecular sieves (3A) and passed through a thin pad of hydrous magnesium silicate. The solvent was removed under vacuum and the residue sublimed to give 7.72 g of 1-methyl-1,2,4-triazole, mp 18°-20° C.

	In tetrahydrofuran; methanol;	Reference Example 60 (S)-2-Amino-4-methyl-(R)-1-(1-methyl-1H-1,2,4-triazol-5-yl)pentan-1-ol To a suspension of 15.2 g of sodium hydride (60percent in oil)(washed with hexane) in 100 ml of tetrahydrofuran under argon was added slowly at 0° to 10°C a solution of 25 g of 1,2,4-triazole in 100 ml of methanol. To this solution was added dropwise 25 ml of methyl iodide over 0.5 hour. The mixture was stirred at 0°C for one hour and then refluxed for 15 minutes. The solution was concentrated under reduced pressure until sodium iodide began to precipitate. The mixture was diluted with 100 ml each of ether and dichloromethane, filtered and the filtrate concentrated to dryness. The residual solid was triturated with dichloromethane (100 ml) and filtered. The filtrate was dried over molecular sieves (3A) and passed through a thin pad of hydrous magnesium silicate. The solvent was removed under vacuum and the residue sublimed to give 7.72 g of 1-methyl-1,2,4-triazole, mp 18-20°C.
	With sodium; In methanol; chloroform; benzene;	1-Methyl-1,2,4-triazole Sodium (1.9 g, 83 mmol) was dissolved in MeOH (35 mL), allowed to cool to RT, then 1,2,4-triazole (5.7 g, 83 mmol) was added. The solution was cooled in an ice-water bath, then iodomethane (5.1 mL, 11.6 g, 82 mmol) was added dropwise. The reaction was allowed to warm to RT, stoppered, then heated at 38° C. overnight. The reaction was concentrated, then treated with hot benzene (25 mL) which resulted in the formation of white solids. Those solids were slurried in hot CHCl3 (25 ML) and filtered off. The CHCl3 slurry was repeated twice, the three filtrates combined, concentrated, and distlled (37-40° C./8 mm). Recovered 2.6 g (38percent). 1H NMR (CDCl3) delta8.05 (s, 1H), 7.93 (s, 1H), 3.96 (s, 3H).
		Intermediate 281 -Methyl-1 H-1 ,2,4-triazole <n="101"/> In a microwave vial sodium methoxide (2.34g) was dissolved in methanol (10ml), 1 H- 1 ,2,4-triazole (3g) was added and the mixture was cooled to 5-1O0C. Methyl iodide (3.26ml) was added and the mixture was heated under microwave irradiation at 800C for 45min. The solvent was removed in vacuo. The oil was allowed to stand for 2h at RT until a solid was formed. To the solid, DCM was added, the DCM was decanted and the solvent was removed in vacuo. The residue was purified by flash chromatography on silica gel (100g silica) eluting with a gradient of 0-25percent methanol in DCM over 40min to give the title compound (1.19g) as a yellow oil. 1H NMR: (400MHz, DMSO) delta 8.45 (1 H, s), 7.95 (1 H, s), 3.85 (3H, s)

References: [1]Chemical Communications,2013,vol. 49,p. 5316 - 5318.
[2]Synthetic Communications,2008,vol. 38,p. 738 - 745.
[3]Chemical Communications,2013,vol. 49,p. 6513 - 6515.
[4]Chemical Communications,2013,vol. 49,p. 6510 - 6512.
[5]Tetrahedron,1990,vol. 46,p. 3211 - 3232.
[6]Gazzetta Chimica Italiana,1905,vol. 35 I,p. 375.
[7]Journal of Organic Chemistry,2002,vol. 67,p. 9340 - 9345.
[8]Patent: US5569655,1996,A .
[9]Patent: US5608056,1997,A .
[10]Patent: US5106835,1992,A .
[11]Patent: EP376040,1990,A3 .
[12]Patent: US6204293,2001,B1 .
[13]Dalton Transactions,2010,vol. 39,p. 4295 - 4301.
[14]Patent: WO2009/147188,2009,A1 .Location in patent: Page/Page column 98-99.

2
[ 628-36-4 ]
[ 288-88-0 ]

References: [1]Journal of the American Chemical Society,1955,vol. 77,p. 621,623.

3
[ 288-88-0 ]
[ 50-00-0 ]
[ 74205-82-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	In tetrahydrofuran; water; at 20℃;	No.88 Triazole (1.00 g, 14.4 mmol) was placed in 100 mL flask. No.42 THF (40 mL) was added at 20C. to give a clear solution. To this, No.89 formaldehyde (1.31 g, 37% aqueous solution) was added and stirred for 4 h to give a homogeneous solution. The solvent was removed under reduced pressure with a rotary evaporator, and the residue was dried in vacuo to afford No.90 (1H-1,2,4-triazol-1-yl)methanol in 96% yield (1.38 g, 13.9 mmol) as a white solid.
89%	With triethylamine; at 140℃; for 0.5h;	Step 1. Preparation of (1H-1,2,4-triazol-1-yl)methanol A mixture of 1H-1,2,4-triazole (7.04 g, 102 mmol), paraformaldehyde (3.06 g, 102 mmol) and catalytic amount of triethylamine was heated to molten condition and stirred at the same temperature (140 C.) for 0.5 hour. Reaction mixture was then cooled to 30 C. to obtain the product (9.0 g, 89%) as white solid.
79%	In ethanol; water; at 20℃; for 13h;Reflux;	The compound was synthesized with some modifications compared to Ref. [14]: (1,2,4)-triazole [98 %(Aldrich), 1,73 g, 25 mmol] in 20 ml of ethanol (absolute ethanol, ≥99.8 %, Sigma-Aldrich) and 3.5 ml of formaldehyde solution (≥36,5 %, Sigma-Aldrich) were stirred, refluxed for 1 h, and mixing was continued at room temperature for 12 h. After the elimination of the solvent under reduced pressure, the obtained residue was treated with cold water. A white solid appeared, which was collected by filtration, washed with diethyl ether (99 %, Sigma-Aldrich) and dried under vacuum to yield the pure product (79 %).

References: [1]Heterocyclic Communications,2001,vol. 7,p. 577 - 582.
[2]Phosphorus and Sulfur and the Related Elements,1987,vol. 33,p. 41 - 52.
[3]Patent: US2020/399196,2020,A1 .Location in patent: Paragraph 0152.
[4]Tetrahedron,2010,vol. 66,p. 9145 - 9150.
[5]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 189 - 194.
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 251 - 256.
[6]Patent: US2016/83380,2016,A1 .Location in patent: Paragraph 0240; 0241.
[7]Structural Chemistry,2016,vol. 27,p. 697 - 704.
[8]Research on Chemical Intermediates,2020,vol. 46,p. 1453 - 1467.

4
[ 288-88-0 ]
[ 530-46-1 ]
p-Tolyl-(4-[1,2,4]triazol-4-yl-phenyl)-methanone [ No CAS ]
p-Tolyl-(4-[1,2,4]triazol-1-yl-phenyl)-methanone [ No CAS ]

References: [1]Archiv der Pharmazie,1990,vol. 323,p. 273 - 280.

5
[ 288-88-0 ]
[ 1798-83-0 ]
[ 81234-31-3 ]

Yield	Reaction Conditions	Operation in experiment
11 g	With sodium acetate; In ethanol; for 12h;Reflux;	15 g of N, N-dimethyl-3-oxo-3,4-chlorophenyl-propyl-1-ammonium chloride are addedInto 270 ml of ethanol,Then add 40g of anhydrous sodium acetate and 19g1,2,3-triazole,Heated to reflux for 12 hours,Concentrate, add water and ethyl acetate,Extract the liquid, collect the organic phase,Dry, concentrate,11 g of 1, 4-chlorophenyl-3- (1H-1,2,4-triazol-1-yl) propan-1-one was obtained.

References: [1]Journal of Medicinal Chemistry,1987,vol. 30,p. 1497 - 1502.
[2]Patent: CN107176928,2017,A .Location in patent: Paragraph 0023; 0024.

6
[ 288-88-0 ]
[ 350-46-9 ]
[ 6219-55-2 ]

Yield	Reaction Conditions	Operation in experiment
91%		At 0 C., to a solution of 1,2,4-triazole (2.7 g, 39.01 mmol) in DMF (50 mL) was added sodium hydride (1.6 g, 39.01 mmol). The mixture was stirred for 30 minutes and 1-flouro-4-nitrobenzene (5.0 g, 35.46 mmol) was added, and the resultant mixture was stirred for further 2 hours. Water (150 mL) was added slowly to the mixture, there was solid precipitated. After filtration, the filter cake was washed with water (50 mL×3), and the solid was dried in vacuum for 8 hours to give yellow solid 10-b (6.2 g, yield: 91%), which was used for the next step without further purification. LC-MS (ESI): m/z=191 [M+H]+
		45A 1-(4-Nitro-phenyl)-1H-[1,2,4]triazole 15 g of 1,2,4 triazole were dissolved in DMF and 8.8 g of NaH (60% in oil) were added. The mixture was stirred at RT for 6 hours and 28.2 g of 1 fluoro-4-nitrobenzene were added. After 6 hours at RT, water was added and the resulting precipitate was washed by ethanol to give 36 g of a product melting at 198 C. used as such in the next step.
		[0004981 To a stirred solution of compound 1 (3 g, 1 eq) in DMF (40 mL), K2C03 (8.8 g, 3 eq) was added and stirred for 15 mm followed by the addition of compound 2 (3.6 g, 1 eq). The reaction mixture was stirred at room temperature for 12 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with ice cold water. The precipitated solid was collected by filtration, washed with water and dried under reduced pressure to afford the title compound 3. LCMS (mlz): 191.00 (M + 1).

120 mg

With potassium carbonate; In dimethyl sulfoxide; at 20 - 80℃; for 16.25h;

1(200 mg, 1.41 mmol), DMSO (3 mL), 1,2,4-triazole (1.1 eq), K2C03 (3.0 eq), RT for5 mm; gradually heated to 80C for 10 mm and stirred for 16 h. Work up and column purification afforded 120 mg of 2.

References: [1]Patent: US2015/336982,2015,A1 .Location in patent: Paragraph 0160; 0161.
[2]Australian Journal of Chemistry,1993,vol. 46,p. 417 - 425.
[3]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 1935 - 1946.
[4]Journal of Medicinal Chemistry,1999,vol. 42,p. 4981 - 5001.
[5]Patent: US2005/143384,2005,A1 .Location in patent: Page/Page column 23.
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2012,vol. 51,p. 731 - 738.
[7]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000498.
[8]Patent: WO2016/73652,2016,A1 .Location in patent: Page/Page column 61.

7
[ 288-88-0 ]
[ 350-46-9 ]
[ 6219-55-2 ]
[ 16759-47-0 ]

References: [1]Synthetic Communications,1993,vol. 23,p. 1947 - 1952.

8
[ 288-88-0 ]
[ 77-78-1 ]
[ 6086-21-1 ]
[ 10570-40-8 ]

References: [1]Acta Chemica Scandinavica,1990,vol. 44,p. 1050 - 1057.

9
[ 288-88-0 ]
[ 74-88-4 ]
[ 6086-21-1 ]
[ 10570-40-8 ]

References: [1]Bulletin des Societes Chimiques Belges,1988,vol. 97,p. 573 - 598.
[2]Tetrahedron Letters,2000,vol. 41,p. 1297 - 1301.
[3]Acta Chemica Scandinavica,1990,vol. 44,p. 1050 - 1057.

10
[ 74205-82-6 ]
[ 288-88-0 ]

References: [1]Chemistry of Heterocyclic Compounds,1980,vol. 16,p. 189 - 194.
Khimiya Geterotsiklicheskikh Soedinenii,1980,vol. 16,p. 251 - 256.

11
[ 288-88-0 ]
[ 108649-59-8 ]
1-<2-(2,4-dichlorophenyl)ethyl>-1,2,4-triazole [ No CAS ]