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[ CAS No. 15294-81-2 ]

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Chemical Structure| 15294-81-2
Chemical Structure| 15294-81-2
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CAS No. :15294-81-2 MDL No. :MFCD08062401
Formula : C2HBr2N3 Boiling Point : 347.5°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :226.86 g/mol Pubchem ID :312397
Synonyms :

Safety of [ 15294-81-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 15294-81-2 ]

  • Upstream synthesis route of [ 15294-81-2 ]
  • Downstream synthetic route of [ 15294-81-2 ]

[ 15294-81-2 ] Synthesis Path-Upstream   1~7

  • 1
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YieldReaction ConditionsOperation in experiment
93% With bromine In water at 50℃; for 41.5 h; Example 120: Preparation of 4,5-dibromo-lH-π,2,31triazoleRr Br. BrN^ NH *" ' \\V NVNH <n="69"/>To a solution of IH-[1, 2,3]triazole (1.26 ml, 21.7 mmol) in water (10 ml) at 5tfC, was added bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at 5CPC for 1.5 hours. The white solid (2.375 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (1.83 g) was isolated via filtration and washed with water (5 ml). To the combined filtrates was added more bromine (1.5 ml, 29 mmol). The reaction mixture was stirred at room temperature for 20 hours. More white solid (375 mg) was isolated via filtration and washed with water (5ml). The white solids were combined and dried to give 4,5-dibromo- IH-[1, 2,3]- triazole (4.92 g, 93percent yield). M.p. 194.7C.
90.39% With bromine In water at 25 - 45℃; for 17 h; Intermediate 14f (0556) 4,5-Dibromo-lH-triazole (0557) Br2 (930 g, 5.82 mol) was added dropwise to a stirred solution of lH-triazole (300.00 g, 4.34 mol, 252.10 mL) in H20 (2 L) at 40 to 45 °C. The resulting solution was stirred for a further 1 hour. The precipitate was filtered off and further Br2 (617.28 g, 3.86 mol) was added to the filtrate, then it was kept at 25 °C for 16 hours. A second precipitate was filtered off. The combined filtered off solids were washed with water (1 L x 3), dried under vacuum and re-crystallized from MeOH (-400 mL) to give 4,5-dibromo-lH-triazole (Intermediate 14f; 890 g, 90.39percent yield) as an off-white solid, m/z (ES+) [M+H]+ (0558) 226/228/230.
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 12, p. 1341 - 1347
[2] Patent: WO2007/96576, 2007, A1, . Location in patent: Example I20
[3] Patent: WO2017/80980, 2017, A1, . Location in patent: Page/Page column 68-69
[4] Justus Liebigs Annalen der Chemie, 1947, vol. 558, p. 34,41
[5] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1535 - 1543
[6] Patent: WO2007/71900, 2007, A1, . Location in patent: Page/Page column 111-112
[7] Patent: WO2012/138648, 2012, A1, . Location in patent: Page/Page column 82-83
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  • [ 16681-70-2 ]
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Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 12, p. 1341 - 1347
[2] Patent: US4596596, 1986, A,
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Reference: [1] Justus Liebigs Annalen der Chemie, 1955, vol. 593, p. 200 - 207
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YieldReaction ConditionsOperation in experiment
26% With triethylamine In dichloromethane at 20℃; for 27 h; Example 160: Preparation of 4,5-dibromo-l-methyl-lH-[1.2.31triazole and 4,5-dibromo- 2-methyl-2H-r 1 ,231triazole(A) (B)To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 159) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 μl, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 μl, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched with aqueous ammonium chloride (saturated, 15 ml). The organic extract was dried over magnesium sulfate and concentrated and the residue was purified by column chromatography on silica gel (eluent 10-30percent ethyl acetate in hexane) to give 4,5-dibromo-2- methyl-2H-[l ,2,3]triazole (isomer B) (625 mg, 26percent yield) and 4,5-dibromo- 1-methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34percent yield). Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.
34% With triethylamine In dichloromethane at 20℃; for 27 h; Example 121: Preparation of 4,5-dibromo-l-methyl-lH-[l,2,3"|triazole and 4,5-dibromo- 2-methyl-2H-[l .2.31triazole(A) (B) To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 120) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 μl, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 μl, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched by addition of aqueous ammonium chloride (saturated) (15 ml). The phases were separated and the organic phase was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 10-30percent ethyl acetate in hexane) to give 4,5-dibromo-2-methyl-2H-[l,2,3]triazole (isomer B) (625 mg, 26percent yield) and 4,5-dibromo- 1 -methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34percent yield).Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1535 - 1543
[2] Patent: WO2007/71900, 2007, A1, . Location in patent: Page/Page column 112
[3] Patent: WO2007/96576, 2007, A1, . Location in patent: Example I21
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  • [ 28938-17-2 ]
  • [ 25537-64-8 ]
YieldReaction ConditionsOperation in experiment
26% With triethylamine In dichloromethane at 20℃; for 27 h; Example 160: Preparation of 4,5-dibromo-l-methyl-lH-[1.2.31triazole and 4,5-dibromo- 2-methyl-2H-r 1 ,231triazole(A) (B)To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 159) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 μl, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 μl, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched with aqueous ammonium chloride (saturated, 15 ml). The organic extract was dried over magnesium sulfate and concentrated and the residue was purified by column chromatography on silica gel (eluent 10-30percent ethyl acetate in hexane) to give 4,5-dibromo-2- methyl-2H-[l ,2,3]triazole (isomer B) (625 mg, 26percent yield) and 4,5-dibromo- 1-methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34percent yield). Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.
34% With triethylamine In dichloromethane at 20℃; for 27 h; Example 121: Preparation of 4,5-dibromo-l-methyl-lH-[l,2,3"|triazole and 4,5-dibromo- 2-methyl-2H-[l .2.31triazole(A) (B) To a solution of 4,5-dibromo- IH-[1, 2,3]triazole (2.26 g, 10 mmol) (Example 120) and triethyl amine (1.5 ml, 10 mmol) in dichloromethane (50 ml), was added methyl iodide (625 μl, 10 mmol). The reaction mixture was stirred at room temperature for 24 hours. More triethyl amine (0.75 ml, 5 mmol) and more methyl iodide (312 μl, 5 mmol) were added and the mixture was stirred for 3 hours. The reaction mixture was quenched by addition of aqueous ammonium chloride (saturated) (15 ml). The phases were separated and the organic phase was dried over magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: 10-30percent ethyl acetate in hexane) to give 4,5-dibromo-2-methyl-2H-[l,2,3]triazole (isomer B) (625 mg, 26percent yield) and 4,5-dibromo- 1 -methyl- IH-[1, 2,3]triazole (isomer A) (825 mg, 34percent yield).Isomer A 1H-NMR (400 MHz, CDCl3): 4.09 (s, 3H, Me) ppm. Isomer B 1H-NMR (400 MHz, CDCl3): 4.18 (s, 3H, Me) ppm.
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 13, p. 1535 - 1543
[2] Patent: WO2007/71900, 2007, A1, . Location in patent: Page/Page column 112
[3] Patent: WO2007/96576, 2007, A1, . Location in patent: Example I21
  • 6
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  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
23.5% With potassium carbonate In N,N-dimethyl-formamide at -10 - 25℃; for 16 h; Inert atmosphere Intermediate 14e (0554) 4,5-Dibromo-2-methyl-2H-l,2,3-triazole Batch 1 : To a solution of 4,5-dibromo-lH-triazole (Intermediate 14f; 490.00 g, 2.16 mol) in DMF (3.2 L) was added potassium carbonate (358.23 g, 2.59 mol). The mixture was cooled to -10°C under a nitrogen atmosphere and iodomethane (147.91 mL, 2.38 mol) was added dropwise. The reaction was then stirred at 25°C for 16 hours. Batch 2: To a solution of 4,5-dibromo-lH-triazole (Intermediate 14f; 400 g, 1.76 mol, 1.00 eq) in DMF (2.8 L) was added potassium carbonate (291.9 g, 2.11 mol). The mixture was cooled to - 10°C under a nitrogen atmosphere and iodomethane (131.48 mL, 2.11 mol) was added dropwise. The reaction was then stirred at 25°C for 16 hours. Batches 1 and 2 were then combined and the reaction was quenched by the addition of water (4.2 L) and the aqueous phase extracted with MTBE (7 L x 3). The organic extract was concentrated under vacuum to approximately 700 mL and isopropanol (2 L) was added dropwise. This mixture was then stirred at 25 °C for 2 hours and the resulting precipitate filtered and dried under vacuum to afford undesired 4,5-dibromo-l-methyltriazole (220 g, 23.5percent) as a solid which showed the following NMR spectral data: FontWeight="Bold" FontSize="10" H NMR (400MHz, CDCb) δ 4.09 (s, 3H). 13CNMR (400MHz, CDCb) δ 123.03, 113.09, 37.00. The filtrate was concentrated under vacuum to afford an oil, isopropanol (1 L) was added and resulting solution was warmed to 50 °C and then water (3 L) was added dropwise. The mixture was cooled to 25°C and stirred for 5 hours and the resulting precipitate was collected by filtration, washed with water (300 mL x 2) and, dried under vacuum at 50°C for 16 hours to afford 4,5-dibromo-2- methyl-2H-l,2,3-triazole (Intermediate 14e; 570 g, 60.8percent yield) as a solid. FontWeight="Bold" FontSize="10" H NMR (400MHz, CDCb) δ 4.18 (s, 3H). 13C NMR (400MHz, CDCb) δ 124.25, 43.07.
Reference: [1] Patent: WO2017/80980, 2017, A1, . Location in patent: Page/Page column 67-68
[2] Patent: WO2012/138648, 2012, A1, . Location in patent: Page/Page column 82-83
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  • [ 421-85-2 ]
  • [ 77287-34-4 ]
  • [ 1353744-13-4 ]
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Reference: [1] Russian Journal of Organic Chemistry, 2011, vol. 47, # 12, p. 1914 - 1916
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