13351-73-0

Usage

Uses

Used in Pharmaceutical Industry:
1-Methylbenzotriazole is used as a protease inhibitor for its ability to inhibit the activity of protease enzymes like chymotrypsin, trypsin, and papain. This property makes it valuable in the development of drugs targeting protease-related diseases and conditions.
Used in Biochemical Research:
1-Methylbenzotriazole is used as a research tool in biochemical studies to understand the mechanisms of action and regulation of protease enzymes. Its inhibitory effect on these enzymes aids in the investigation of their roles in various biological processes.
Used in Food Industry:
1-Methylbenzotriazole can be used as a preservative in the food industry to inhibit the activity of protease enzymes that cause spoilage and deterioration of food products. This helps in extending the shelf life and maintaining the quality of the food items.
Used in Cosmetic Industry:
In the cosmetic industry, 1-Methylbenzotriazole may be utilized as an ingredient in skincare products to inhibit protease enzymes that contribute to skin aging and degradation. Its inclusion in cosmetic formulations can potentially offer anti-aging benefits and improve skin health.
Used in Agricultural Industry:
1-Methylbenzotriazole can be employed in the agricultural sector as a protective agent for crops. By inhibiting protease enzymes that cause damage to plants, it can help in reducing crop losses and improving overall agricultural productivity.

InChI:InChI=1/C7H7N3/c1-10-7-5-3-2-4-6(7)8-9-10/h2-5H,1H3

Synthetic route

1,2,3-Benzotriazole (95-14-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
In N,N-dimethyl-formamide at 90℃; for 4h;	87.8%

methyl magnesium iodide (917-64-6) + 1-(chloromethyl)-1H-benzotriazole (54187-96-1) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1-ethylbenzotriazole (16584-05-7)

Conditions	Yield
In diethyl ether for 1h; Ambient temperature;	A 83% B 11%

1,2,3-Benzotriazole (95-14-7) + P-(dichloromethyl) O-methyl chlorophosphonate → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 1h; Alkylation;	80%

1,2,3-Benzotriazole (95-14-7) + methyl iodide (74-88-4) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With sodium hydroxide In water; acetonitrile for 48h;	73%
With potassium tert-butylate; 18-crown-6 ether In diethyl ether for 1h; Ambient temperature;	70%
Stage #1: 1,2,3-Benzotriazole With sodium hydride In tetrahydrofuran; mineral oil for 0.0833333h; Stage #2: With carbon disulfide In tetrahydrofuran; mineral oil at 0 - 5℃; Stage #3: methyl iodide In tetrahydrofuran; mineral oil at 0 - 5℃; for 0.2h;	67%
With sodium hydroxide In water; acetonitrile at 20℃; for 48h;	55%

1H-benzotriazole-1-carboxylic acid methyl ester (86298-22-8) → 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
at 120℃; Title compound not separated from byproducts;	A 29% B 71%
at 160℃;
at 160℃;
at 120℃; Mechanism; other alkoxycarbonylbenzotriazoles;	A 29 % Spectr. B 71 % Spectr.

1-benzyl-3-methylbenzotriazolium iodide (1334478-48-6) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + (E)-1,2-diphenyl-ethene (103-30-0)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 20℃; stereoselective reaction;	A n/a B 68%

N-chlorobenzotriazole (21050-95-3) → 1,2,3-Benzotriazole (95-14-7) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1-iodobenzotriazole (68407-95-4) + 1,3-dimethylbenzotriazolium triiodide

Conditions	Yield
With methyl iodide In dichloromethane at 42℃; for 1h;	A 10% B 6% C 65% D 19%
With methyl iodide In dichloromethane at 42℃; for 3h;	A 18% B 11% C 41% D 30%

1,2,3-Benzotriazole (95-14-7) + dimethyl sulfate (77-78-1) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With sodium hydroxide at 20℃; for 2.5h;	65%
With sodium hydroxide In water at 20 - 80℃; for 0.75h;

N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide (127236-78-6) + benzylmagnesium chloride (6921-34-2) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1-phenethyl-1H-benzo[d][1,2,3]triazole (63777-68-4)

Conditions	Yield
In tetrahydrofuran; diethyl ether at 45℃; for 3h;	A n/a B 64%

N-methyl-1,2-phenylenediamine (4760-34-3) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With tert.-butylhydroperoxide; nitromethane; caesium carbonate; acetic acid; potassium iodide In water at 120℃; for 12h; Schlenk technique; Inert atmosphere; chemoselective reaction;	62%
With hydrogenchloride Diazotization.und Verkochen das entstandende Diazoniumsalz;

1,2,3-Benzotriazole (95-14-7) + methyl iodide (74-88-4) → 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With sodium hydroxide In N,N-dimethyl-formamide for 0.5h;	A 40% B 60%
With potassium hydroxide; tetrabutylammomium bromide at 0℃; Yields of byproduct given;	A 25% B n/a
With sodium hydroxide In N,N-dimethyl-formamide for 0.25h; Ambient temperature; Yield given. Yields of byproduct given;
With potassium hydroxide; tetrabutylammomium bromide Ambient temperature; Irradiation; Yield given. Yields of byproduct given;
With potassium hydroxide; 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 2h;

Dimethyl oxalate (553-90-2) + 1,2,3-Benzotriazole (95-14-7) → 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With potassium tert-butylate In N,N-dimethyl-formamide Heating;	A 35% B 59%
With potassium tert-butylate In N,N-dimethyl-formamide for 3h; Heating;	A 35% B 59%
With potassium tert-butylate In N,N-dimethyl-formamide for 3h; Heating;	A 35% B 59%

N,N-dimethyl-2-nitro-benzenamine (610-17-3) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + N-nitroso N-methyl-N-(2-nitroaniline) (89937-90-6) + N-methyl-N-nitrosoaniline (614-00-6) + 2-nitro-N-methylaniline (612-28-2)

Conditions	Yield
With n-Butyl nitrite; ammonium chloride; water for 2h; Heating; Further byproducts given;	A 7% B 58% C 9% D 5%

N,N-dimethyl-2-nitro-benzenamine (610-17-3) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + N-nitroso N-methyl-N-(2-nitroaniline) (89937-90-6) + 2-nitro-N-methylaniline (612-28-2) + nitrobenzene (98-95-3)

Conditions	Yield
With n-Butyl nitrite; ammonium chloride; water for 2h; Mechanism; Heating;	A 7% B 58% C 5% D 1%

1-benzyl-3-methylbenzotriazolium bromide (37922-13-7) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + (E)-1,2-diphenyl-ethene (103-30-0)

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 20℃; stereoselective reaction;	A n/a B 56%

N-chlorobenzotriazole (21050-95-3) + methyl iodide (74-88-4) → 1,2,3-Benzotriazole (95-14-7) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1-iodobenzotriazole (68407-95-4) + 1,3-dimethylbenzotriazolium triiodide

Conditions	Yield
In dichloromethane at 42℃; for 7h;	A 8% B 21% C 16% D 55%
In dichloromethane at 42℃; for 5h;	A 8% B 28% C 29% D 35%

N-chlorobenzotriazole (21050-95-3) + methyl iodide (74-88-4) → 1,2,3-Benzotriazole (95-14-7) + 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1,3-dimethylbenzotriazolium triiodide

Conditions	Yield
In dichloromethane at 42℃; for 3h; Further byproducts given;	A 8% B 3% C 33% D 49%

(E)-benzotriazole-1-carbaldehyde oxime (147861-10-7) + methyl iodide (74-88-4) → 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + (E)-1-formylbenzotriazole O-methyloxime

Conditions	Yield
With sodium ethanolate In ethanol at 25℃; for 24h;	A 12% B 42% C 26%

tert.-butylhydroperoxide (75-91-2) + 1,2,3-Benzotriazole (95-14-7) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In water; acetonitrile at 100℃; for 8h; Schlenk technique; Inert atmosphere; regioselective reaction;	42%

1,2,3-Benzotriazole (95-14-7) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
In toluene for 0.5h; Heating;	A 38% B 10%

N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide (127236-78-6) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1-[(1H-benzotriazol-1-yl)methyl]-1H-benzotriazole (88064-00-0)

Conditions	Yield
In diphenylether at 200℃; for 2h;	A 15% B 38%

N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide (127236-78-6) + N,N-diethylaniline (91-66-7) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1-ethylbenzotriazole (16584-05-7) + 1-[(1H-benzotriazol-1-yl)methyl]-1H-benzotriazole (88064-00-0)

Conditions	Yield
at 200℃; for 4h;	A 8% B 37% C 28%

N-bromobenzotriazole (65763-68-0) + methyl iodide (74-88-4) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1,3-dimethylbenzotriazolium triiodide

Conditions	Yield
In dichloromethane at 42℃; for 3h;	A 26% B 35%

6-chloro-1-methyl-4-nitrobenzotriazole → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With hydrazine hydrate In ethanol at 70℃; for 90h;	32%

1-amino-3-methylbenzimidazolium chloride → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + N-methyl-N-phenylformamide (93-61-8)

Conditions	Yield
With lead(IV) acetate In methanol for 0.5h; Ambient temperature;	A 20.2% B 17.2%

2-Chloronitrobenzene (88-73-3) + methylhydrazine (60-34-4) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 3-methyl-3H-1,2,3-benzotriazole 1-oxide (22713-36-6) + 2-nitro-N-methylaniline (612-28-2) + 2-Chloroaniline (95-51-2)

Conditions	Yield
In ethanol at 150℃; for 5h;	A 12% B n/a C n/a D 20%

1-iodobenzotriazole (68407-95-4) + methyl iodide (74-88-4) → 1,2,3-Benzotriazole (95-14-7) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1,3-dimethylbenzotriazolium triiodide

Conditions	Yield
In dichloromethane at 42℃; for 3h;	A 10% B 10% C 12%

1-iodobenzotriazole (68407-95-4) → 1,2,3-Benzotriazole (95-14-7) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 1,3-dimethylbenzotriazolium triiodide

Conditions	Yield
With methyl iodide In dichloromethane at 42℃; for 3h;	A 10% B 10% C 12%

diazomethane (186581-53-3, 908094-01-9) + 1,2,3-Benzotriazole (95-14-7) → 2-methylbenzotriazole (16584-00-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With ethanol

1-(chloromethyl)-1H-benzotriazole (54187-96-1) → 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0)

Conditions	Yield
With lithium aluminium tetrahydride
Multi-step reaction with 2 steps 1: 40 percent / methanol / 1 h / Heating 2: toluene; diethyl ether / Heating View Scheme
Multi-step reaction with 2 steps 1: 87 percent / toluene; methanol / 2 h / Heating 2: benzene; diethyl ether / Heating View Scheme

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + borane-THF (14044-65-6) → N-1-methyl-benzotriazole-N-3-borane (1201669-53-5)

Conditions	Yield
In not given (C6H4N3)Me (1.1 equiv.), 1.0 M BH3*THF (1.0 equiv.), room temp.;	99%
In tetrahydrofuran for 2h; Cooling with ice;	84%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) → N-1-methyl-benzotriazole-N-3-borane (1201669-53-5)

Conditions	Yield
With borane-THF In tetrahydrofuran at 20℃; Inert atmosphere;	99%

gold(III) chloride + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + silver trifluoromethanesulfonate (2923-28-6) → C34H43AuN5(1+)*CF3O3S(1-)

Conditions	Yield
In methanol at 20℃; for 6h;	97%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + nickel(II) chloride hexahydrate → Ni(2+)*2Cl(1-)*C6N3H4CH3=NiCl2(C6N3H4CH3)

Conditions	Yield
With triethyl orthoformate In ethanol to a soln. of NiCl2*6H2O in abs. ethanol was added CH(OEt)3, refluxed for 30 min, addn. of the triazole (molar ratio 1:1); filtered, washed with ethanol and Et2O, dried in vac. over silica gel; elem. anal.;	96%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + cobalt(II) bromide → (Br2)(1-methylbenzotriazolyl)2cobalt(II) (146262-41-1)

Conditions	Yield
In ethanol dropwise addn. of CoBr2 in absolute EtOH to a stirred solution of ligand in absolute EtOH (under aerobic conditions), forming ppt., further stirring for 30 min; filtn., washing with EtOH and diethyl ether, drying in vacuo over silica gel, elem. anal.;	95%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + phenanthridine (229-87-8) + propynoic acid methyl ester (922-67-8) → (E)-methyl 3-(6-(1H-benzo[d][1,2,3]triazol-1-yl)phenanthridin-5(6H)-yl)acrylate

Conditions	Yield
In dichloromethane at -10 - 20℃;	91%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) → 3-methyl-3H-1,2,3-benzotriazole 1-oxide (22713-36-6)

Conditions	Yield
With 3,3-dimethyldioxirane In dichloromethane at 20℃; for 24h;	90%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + phenanthridine (229-87-8) + propynoic acid ethyl ester (623-47-2) → (E)-ethyl 3-(6-(1H-benzo[d][1,2,3]triazol-1-yl)phenanthridin-5(6H)-yl)acrylate

Conditions	Yield
In dichloromethane at -10 - 20℃;	90%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) → 1,3,5-triphenylhexahydro-1,3,5-triazine (91-78-1)

Conditions	Yield
at 700℃; under 0.01 Torr; Elimination; Cyclotrimerization;	89%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + cobalt(II) chloride hexahydrate → (MebtaH)((chloro)3(1-methylbenzotriazolyl)cobaltate(II)) (146262-39-7)

Conditions	Yield
With concd. HCl In ethanol addn. of CoCl2*6H2O in concd. HCl-EtOH to a stirred soln. of ligand in concd. HCl-EtOH (under aerobic conditions), formation of ppt.; filtn., washing with EtOH and diethyl ether, drying in vacuo over silica gel, elem. anal.;	89%

4-methyl-benzoic acid methyl ester (99-75-2) + 1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) → 2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)-1-ethanone (189343-47-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	88%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + Methyl decanoate (110-42-9) → 1-Benzotriazol-1-yl-undecan-2-one (189343-46-2)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	88%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + copper(ll) bromide (7789-45-9) → CuBr2(C6H4N3CH3) (88177-45-1)

Conditions	Yield
In acetone room temp. (overnight); filtering, washing (Me2CO, Et2O), drying (vac., over SiO2); elem. anal.;	88%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + 2-methylmercaptobenzothiazole (615-22-5) → 1-(1,3-Benzothiazol-2-ylmethyl)-1H-1,2,3-benzotriazole (156272-74-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 24h;	85%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + nickel(II) chloride hexahydrate → Ni(2+)*2Cl(1-)*2C6N3H4CH3=NiCl2(C6N3H4CH3)2

Conditions	Yield
With triethyl orthoformate In ethanol to a soln. of NiCl2*6H2O in abs. ethanol was added CH(OEt)3, refluxed for 30 min, addn. of the triazole (molar ratio 1:2); filtered, washed with ethanol and Et2O, dried in vac. over silica gel; elem. anal.;	85%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + cobalt(II) thiocyanate (3017-60-5) → (cobalt(isothiocyanate)2(1-methylbenzotriazole)2) (146262-43-3)

Conditions	Yield
In acetone addn. of solid ligand to a stirred soln. of Co(NCS)2 in acetone (under aerobic conditions), stirring for 10 min at room temp.; filtn., addn. of n-hexane to the filtrate to yield dark blue oil, solidification on overnight storage in a freezer, collection by filtn., washing with n-hexane, drying in vacuo over silica gel, elem. anal.;	84%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + ethyl pelargonate (123-29-5) → 1-Benzotriazol-1-yl-decan-2-one (189343-45-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	83%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + cobalt(II) chloride (7646-79-9) → (chloro)2(1-methylbenzotriazolyl)2cobalt(II) (146262-37-5)

Conditions	Yield
In ethanol dropwise addn. of CoCl2 in absolute EtOH to a stirred solution of ligand in absolute EtOH (under aerobic conditions), forming ppt., further stirring for 30 min; filtn., washing with EtOH and diethyl ether, drying in vacuo over silica gel, elem. anal.;	83%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + α-bromoacetophenone (70-11-1) → 3-methyl-1-phenacylbenzotriazolium bromide (132416-78-5)

Conditions	Yield
In toluene for 5h; Heating;	80%
In ethyl acetate for 3h; Heating;	72%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + nickel(II) thiocyanate (13689-92-4) → Ni(NCS)2(CH3OH)2(C6N3H4CH3)2 (157037-34-8)

Conditions	Yield
With methanol In methanol the triazole was dissolved with stirring in a soln. of Ni(SCN)2 in refluxing methanol, left undisturbed at ambient temp.; filtered, washed with Et2O, dried in air; elem. anal.;	80%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + copper dichloride → [Cu2Cl4(1-methylbenzotriazole)2]n

Conditions	Yield
With HC(OEt)3 In ethanol dissoln. of equimolar amts. of CuCl2 and ligand in EtOH contg. HC(COEt)3; crystn. (2 d, room temp.), filtration, washing (Et2O), drying (vac.); elem. anal.;	80%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + Ethyl hexanoate (123-66-0) → 1-(1H-1,2,3-benzotriazol-1-yl)-2-heptanone (189343-44-0)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	78%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + nickel(II) nitrate hexahydrate → Ni(NO3)2(C6N3H4CH3)4 (157037-29-1)

Conditions	Yield
With triethyl orthoformate In ethanol to a soln. of the triazole in abs. ethanol was added a soln. of Ni(NO3)2*6H2O in the same solvent, addn. of CH(OEt)3, refluxed for 30 min; addn. of Et2O to the cooled soln., filtered, washed with Et2O, dried in vac. over silica gel; elem. anal.;	78%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + methyl trifluoromethanesulfonate → 1,3-Dimethylbenzotriazolium trifluoromethanesulphonate

Conditions	Yield
In dichloromethane for 144h; Ambient temperature;	77%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + (triphenylphosphine)gold(I) chloride + silver trifluoromethanesulfonate (2923-28-6) → triazole (1186016-23-8)

Conditions	Yield
Stage #1: (triphenylphosphine)gold(I) chloride; silver trifluoromethanesulfonate In methanol for 0.0833333h; Inert atmosphere; Stage #2: 1-methyl-1H-benzo[d][1,2,3]triazole In methanol at 20℃; for 12h; Inert atmosphere;	76%
byproducts: AgCl;

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + acetonitrile (75-05-8) + copper(ll) bromide (7789-45-9) → CuBr2(C6H4N3CH3)2(CH3CN) (255913-57-6)

Conditions	Yield
In acetonitrile room temp. (24 h); filtering, washing (Et2O), drying; elem. anal.;	75%

1-methyl-1H-benzo[d][1,2,3]triazole (13351-73-0) + nickel(II) bromide trihydrate → NiBr2(CH3OH)2(C6N3H4CH3)2 (157037-39-3)

Conditions	Yield
With triethyl orthoformate In methanol to a stirred soln. of NiBr2*3H2O in abs. methanol were added CH(OEt)3 and a soln. of the triazole in abs. methanol, refluxed for 30 min; layered with Et2O at 4°C, slow mixing, filtered, washed with Et2O, dried in air; elem. anal.;	74%

Upstream product

• 186581-53-3 diazomethane 
• 95-14-7 1,2,3-Benzotriazole 
• 86298-22-8 1H-benzotriazole-1-carboxylic acid methyl ester 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 553-90-2 Dimethyl oxalate 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 917-64-6 methyl magnesium iodide 
• 127236-78-6 N-(benzotriazol-1-ylmethyl)-N-methylpyrrolidinium iodide 
• 10467-10-4 ethylmagnesium iodide 
• 111198-02-8 1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole 
• 88-73-3 2-Chloronitrobenzene 
• 60-34-4 methylhydrazine 

Downstream Products

• 22713-35-5 1,3-dimethylbenzotriazolium iodide 
• 27799-86-6 1-methyl-4-nitro-1H-benzotriazole 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 189343-47-3 2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)-1-ethanone 
• 1186016-23-8 triazole 
• 19611-73-5 2-(1-methyl-2-oxoindolin-3-ylidene)-N-phenylacetamide 
• 18450-24-3 ethyl N-methylindole-2-carboxylate 
• 38182-45-5 N-methyl-N,N'-o-phenylene-bis-benzamide 
• 69218-29-7 1-isopropyl-1H-benzotriazole 
• 189343-58-6 1-(benzotriazol-1-yl)-2-undecanone p-tosylhydrazone 
• 189343-57-5 1-(benzotriazol-1-yl)-2-decanone p-tosylhydrazone 
• 189343-59-7 1-(benzotriazol-1-yl)-2-(p-tolyl)ethan-2-one p-tosylhydrazone 
• 189343-56-4 1-(benzotriazol-1-yl)-2-heptanone p-tosylhydrazone 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 

Relevant academic research and scientific papers

Ammonium Arylspiroborate Compounds: Synthesis, Crystal Structure, Fluorescence Properties, and Antibacterial Activity

A series of R-substituted ammonium arylspiroborate compounds (R = CH3, H, F, Cl, Br) have been synthesized via a facile one-pot method. The structures of these new kinds of boron compounds were characterized by IR, NMR spectra, elemental analys

Azole-carbodithioate hybrids as vaginal anti-Candida contraceptive agents: Design, synthesis and docking studies

Azole and carbodithioate hybrids were synthesized as alkyl 1H-azole-1-carbodithioates (7-27) and evaluated for spermicidal/microbicidal activities against human sperm, Trichomonas vaginalis and Candida species. Seventeen compounds (7-14, 16-18 and 20-25)

The Mitsunobu reaction: An alternative synthesis of 1-(primary alkyl)benzotriazoles

1-(Primary alkyl)benzotriazoles are obtained in convenient yields by treating the corresponding alcohol with triphenylphosphine, N-bromosuccinimide and benzotriazole. Under these conditions, the alcohols gave exclusively the corresponding 1-alkyl-benzotriazoles. Allyl and propargyl alcohols also reacted regiospecifically in a typical S(N)2 manner, and no products derived from prototropic rearrangement were found.

1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) derived from chloronitrobenzotriazoles and hydrazine

Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4-nitrobenzotriazole (6) and 6-chloro-1-methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4-nitrobenzotriazole (8) or 5-chloro-2-methyl-4,6-dinitrobenzotriazole (9). Introduction of the nitro group activated chlorine atom that underwent nucleophilic displacement by hydrazine to give rise to a new tricyclic system 1H,6H-triazolo[4,5-e]benzotriazole-3-oxide compounds (10 and 11) in the case of 5 and 6. From 9 no linear or angular tricyclic triazolobenzotriazole was obtained but instead the 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).{A figure is presented}.

Reaction of N-vinylindazolium and N-vinylbenzotriazolium salts with nucleophiles

Reaction of N-vinylindazolium tetrafluoroborates with aqueous potassium carbonate or sodium borohydride affords 2,3-dihydroquinazolines which evolve to 1,2,3,4-tetrahydroquinazolines by intra or intermolecular nucleophilic attack. The X-ray structure of o

A NEW SIMPLE PROCEDURE FOR ALKYLATION OF NITROGEN HETEROCYCLES USING DIALKYL OXALATES AND ALKOXIDES.

A variety of nitrogen heterocycles are N-alkylated in high yields with dialkyl oxalates and potassium alkoxides in refluxing dimethylformamide.

Mechanistic study of nucleophilic fluorination for the synthesis of fluorine-18 labeled fluoroform with high molar activity fromN-difluoromethyltriazolium triflate

The synthesis of fluorine-18 labeled fluoroform with high molar activity has grown in importance for the development of fluorine-18 labeled aryl-CF3radiopharmaceuticals that are useful as diagnostic radiotracers for the powerful technique of positron emission tomography (PET). We designed a strategy of synthesizing fluorine-18 labeled fluoroform fromN1-difluoromethyl-N3-methyltriazolium triflate (1)viaSN2 fluorination without stable fluorine isotope scrambling. Fluoroform was generated at rt in 10 min by fluorination of the triazolium precursor with TBAF (6 equiv.). We propose three routes (a), (b), and (c) for this fluorination. Quantum chemical calculations have been carried out to elucidate the mechanism of experimentally observed nucleophilic attack of fluoride at difluoromethyl groupviaroute (a), notN3-methylviaroute (b).1H and19F NMR studies using deuterium source have been performed to examine the competition between SN2 fluorination (route (a)) and the formation of difluorocarbene (route (c)). The observed superiority of SN2 pathway to formation of difluorocarbene in the reaction of the precursor using CsF in (CD3CN/(CD3)3COD (17.8?:?1)) gives the possibility of preparing the fluorine-18 labeled fluoroform in high molar activity.

Bu4NI-Catalyzed, Radical-Induced Regioselective N-Alkylations and Arylations of Tetrazoles Using Organic Peroxides/Peresters

Bu4NI-catalyzed regioselective N2-methylation, N2-Alkylation, and N2-Arylation of tetrazoles have been achieved using tert-butyl hydroperoxide (TBHP) as the methyl source, alkyl diacyl peroxides as the primary alkyl source, alkyl peresters as the secondary and tertiary alkyl sources, and aryl diacyl peroxides as the arylating source. These reactions proceed without pre-functionalization of tetrazole and in the absence of any metal catalysts. Here, peroxides serve the dual role of oxidants as well as alkylating or arylating agents. Based on DFT calculations, it was found that spin density, transition-state barriers (kinetic control), and thermodynamic stability of the products (thermodynamic control) play essential roles in the observed regioselectivity during N-Alkylation. This radical-mediated process is amenable to a broad range of substrates and provides products in moderate to good yields.

Alkylation method for nitrogen-hydrogen containing compounds and application thereof

The invention discloses an alkylation method for nitrogen-hydrogen containing compounds and an application thereof, belonging to the technical field of synthesis of organic compounds. The invention provides a series of methods for a nitrogen alkylation reaction of N-H containing heterocyclic compounds (II) with N,N-dimethylformamide dialkyl acetal as an alkyl source under the condition of no participation of metals, and a product with a hydrogen atom on a nitrogen atom substituted by R1 is obtained. The method provided by the invention has the advantages of highly-efficient reaction, high yield, simple treatment after the reaction, simple and convenient operation, mild reaction conditions, no participation of the metals, high tolerance of functional groups of a reaction substrate, wide range and easy preparation of the substrate, high reaction efficiency after amplification of the reaction, and applicability to large-scale industrial production.

Derisking the Cu-Mediated 18F-Fluorination of Heterocyclic Positron Emission Tomography Radioligands

Molecules labeled with fluorine-18 (18F) are used in positron emission tomography to visualize, characterize and measure biological processes in the body. Despite recent advances in the incorporation of 18F onto arenes, the development of general and efficient approaches to label radioligands necessary for drug discovery programs remains a significant task. This full account describes a derisking approach toward the radiosynthesis of heterocyclic positron emission tomography (PET) radioligands using the copper-mediated 18F-fluorination of aryl boron reagents with 18F-fluoride as a model reaction. This approach is based on a study examining how the presence of heterocycles commonly used in drug development affects the efficiency of 18F-fluorination for a representative aryl boron reagent, and on the labeling of more than 50 (hetero)aryl boronic esters. This set of data allows for the application of this derisking strategy to the successful radiosynthesis of seven structurally complex pharmaceutically relevant heterocycle-containing molecules.