13351-73-0

Basic information

• Product Name: 1-METHYLBENZOTRIAZOLE
• Synonyms: 1H-Benzotriazole, 1-methyl-;1H-Benzotriazole,1-methyl-;1-Methyl-1,2,3-benzotriazole;1-Methyl-1H-1,2,3-benzotriazole;1-methyl-1h-benzotriazol;1-METHYL-1H-BENZOTRIAZOLE;1-METHYLBENZOTRIAZOLE;METHYLBENZOTRIAZOLE
• CAS NO: 13351-73-0
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• EINECS: 236-401-4
• Mol File: 13351-73-0.mol
• Article Data: 36

Chemical Properties

• Melting Point: 64-65°C
• Boiling Point: 155°C/17mmHg(lit.)
• Flash Point: 117.4 °C
• Appearance: /
• Density: 1.1873 (rough estimate)
• Vapor Pressure: 0.0113mmHg at 25°C
• Refractive Index: 1.5341 (estimate)
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility: Chloroform, Methanol (Sparingly)
• PKA: 1.40±0.30(Predicted)
• BRN: 118900
• CAS DataBase Reference: 1-METHYLBENZOTRIAZOLE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-METHYLBENZOTRIAZOLE(13351-73-0)
• EPA Substance Registry System: 1-METHYLBENZOTRIAZOLE(13351-73-0)

Safety Data

• Safety Statements: 22-24/25
• RTECS: DM1330000
• HazardClass: IRRITANT
• Hazardous Substances Data: 13351-73-0(Hazardous Substances Data)

Usage

Uses

A benzotriazole derivative with potential inhibitory effect on protease enzymes chymotrypsin, trypsin and papain.

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 
• 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 
• 10467-10-4 ethylmagnesium iodide 
• 111198-02-8 1-(phenoxymethyl)-1H-benzo[d][1,2,3]triazole 
• 67-56-1 methanol 
• 68985-05-7 1,1′-carbonylbis-benzotriazole 
• 37922-13-7 1-benzyl-3-methylbenzotriazolium bromide 
• 1334478-48-6 1-benzyl-3-methylbenzotriazolium iodide 
• 86298-22-8 1H-benzotriazole-1-carboxylic acid methyl ester 

Downstream Products

• 4144-64-3 2-(1H-1,2,3-benzotriazol-1-yl)acetic acid 
• 127876-36-2 2-(benzotriazol-1-yl)acetophenone 
• 63777-68-4 1-phenethyl-1H-benzo[d][1,2,3]triazole 
• 132416-78-5 3-methyl-1-phenacylbenzotriazolium bromide 
• 16584-05-7 1-ethylbenzotriazole 
• 100-61-8 N-methylaniline 
• 189343-47-3 2-(1H-1,2,3-benzotriazol-1-yl)-1-(4-methylphenyl)-1-ethanone 
• 4760-34-3 N-methyl-1,2-phenylenediamine 
• 91-78-1 1,3,5-triphenylhexahydro-1,3,5-triazine 
• 189343-56-4 1-(benzotriazol-1-yl)-2-heptanone p-tosylhydrazone 
• 189343-59-7 1-(benzotriazol-1-yl)-2-(p-tolyl)ethan-2-one p-tosylhydrazone 
• 189343-57-5 1-(benzotriazol-1-yl)-2-decanone p-tosylhydrazone 
• 189343-58-6 1-(benzotriazol-1-yl)-2-undecanone p-tosylhydrazone 
• 38182-45-5 N-methyl-N,N'-o-phenylene-bis-benzamide 

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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

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