Synthesis of hydroxybenzotriazole

Preparation of hydroxybenzotriazole

Alternative Names: 1-Hydroxybenzotriazole; 2592-95-2; N-Hydroxybenzotriazole; HOBt; 1H-Benzotriazole, 1-hydroxy-; 1H-Benzotriazol-1-ol

Preparation of hydroxybenzotriazole

Preparation of hydroxybenzotriazole

A mixture of 31.5 g (0.2 mol) of o-chloronitrobenzene and 32 ml (0.65 mol) of hydrazine hydrate in 100 ml of alcohol is boiled under reflux for 9 hours. After cooling the solution, the alcohol is removed by evaporation yielding the syrup. This product is dissolved in water, extracted with ether; the aqueous phase is separated and acidified with hydrochloric acid until pH 1. The precipitate is filtered off and purified by crystallization from water. Yield 16 g (60%). The hydroxybenzotriazole melts at about 100 °C, then solidifies and melts again at 157 °C.

Chem. Ber. 27, 3381-3384, 1984

Preparation of hydroxybenzotriazole

Preparation of hydroxybenzotriazole

To a suspension of o-nitrophenylhydrazine (15.3 g, 100 mmol) in water (100 ml) concentrated ammonium hydroxide (100 ml) is added and the mixture is heated on a steam bath with occasional swirling. The starting material dissolves and the color of the solution changes from dark red to light brown. Heating to about 70°C is continued for 15 minutes and the solution is concentrated on the steam bath with the help of an air stream to about half of its original volume. After filtration from a small amount of insoluble material the solution is acidified to Congo with 6 N hydrochloric acid. The mixture is cooled in an ice-water bath for about 1/2 hour, the crystals collected on a filter, washed with cold water (30 ml) and dried in air. The product (11 g, 72 %) melts at 154-156 °C. It is sufficiently pure for most practical purposes, but the m.p. can be raised to 157°C by recrystallization from dilute ethanol. 1-Hydroxybenzotriazole is obtained as the monohydrate.

Chem. Ber. 27, 3381 (1894)

IUPAC Name

1-hydroxybenzotriazole

InChI

InChI=1S/C6H5N3O/c10-9-6-4-2-1-3-5(6)7-8-9/h1-4,10H

InChI Key

ASOKPJOREAFHNY-UHFFFAOYSA-N

Canonical SMILES

C1=CC=C2C(=C1)N=NN2O

MeSH Synonyms

1-hydroxybenzotriazole, 1-hydroxybenzotriazole, ammonium salt, 1-hydroxybenzotriazole, sodium salt, HOBt, N-hydroxybenzotriazole

Depositor-Supplied Synonyms

1-Hydroxybenzotriazole, 2592-95-2, N-Hydroxybenzotriazole, HOBt, 1H-Benzotriazole, 1-hydroxy-, 1H-Benzotriazol-1-ol, Benzazimidol, 1H-1,2,3-Benzotriazol-1-ol, 1H-Benzo[d][1,2,3]triazol-1-ol, 1-Hydroxy-1H-benzotriazole, Benzazimidol hydrate, 1-hydroxybenzotriazol, N-Hydroxybenzotriazol, 1-Hydroxy-benzotriazol, 1-hydroxy benzotriazole, 1-Hydroxy-1H-benzotriazol, 1-hydroxyl-1H-benzotriazole, 1,2,3-Benzotriazol-1-ol, 1-Hydroxybenzotriazole(HOBt), 1-HYDROXY-BENZOTRIAZOLE, CCRIS 2605, 1-Hydroxy-1,2,3-benzotriazole, ASOKPJOREAFHNY-UHFFFAOYSA-N, 1-Hydroxy-1H-benzotriazole hydrate, EINECS 219-989-7, N-Hydroxybenzotriazole hydrate, SBB056385, 1H-Benzotriazole, 1-hydroxy-, hydrate, BRN 0004515, benzotriazolol, 1-Benzotriazolol, HOBt(anhydrous), benztriazol-1-ol, benzotriazol-1-ol, HOBt (anhydrous), 1-hydroxybenztriazol, N-hydroxybenztriazole, 1-hydroxybenztriazole, 1-hyroxybenzotriazole, l-hydroxybenzotriazole, 1hydroxy-benzotriazole, 3-hydroxybenzotriazole, PubChem9767, N-hydroxy-benzotriazol, 1-hydroxy benzotriazol, 1-hydroxy benztriazole, 1-hydroxybenztria zole, 1-hydroxylbenzotriazole, N-hydroxy benzotriazole, N-hydroxy-benzotriazole, 1 -hydroxybenzotriazole, 1- hydroxybenzotriazole, 1-hydroxybenzo-triazole, 1-hydroxybenzotri-azole, N-hydroxyl-benzotriazole, 1-N-Hydroxybenzotriazole, 1-hydroxy-benzo-triazole, AC1L2PHD, AC1Q4XIJ, AC1Q7DHT, N(1)-hydroxybenzotriazole, SCHEMBL184, 1-hydroxy-1H-benztriazole, DSSTox_CID_24627, DSSTox_RID_80362, UNII-A2T929DMG4, DSSTox_GSID_44627, 1,2,3-benzotriazole-1-ol, KSC201S4N, MLS001006716, 1-hydroxy-(1H)-benzotriazole, 1-Hydroxybenzotriazole (HOBT), A2T929DMG4, SCHEMBL2845655, SCHEMBL3295216, SCHEMBL3672275, Jsp005110, CHEMBL1389920, CTK1A1946, MolPort-002-317-330, 1-H-1,2,3-benzotriazol-1-ol, 1-hydroxy-benzo-1,2,3-triazole, HMS1724G04, HMS2742F11, 63307-62-0 (ammonium salt), ACT09417, CS-B0704, 1-HYDROXY-1-H-BENZOTRIAZOLE, Tox21_302480, 1-hydroxy-1H-1,2,3-benzotriazole, ANW-25850, AR-1C3329, 1H-benzo[d][1,2,3]triazole-1-ol, 40150-21-8 (hydrochloride salt), AKOS000120715, AC-2558, AM84845, RP20189, RTR-011763, NCGC00246157-01, NCGC00256701-01, AJ-09861, AK-89521, AN-13855, BC675286, BP-12840, KB-12614, KB-58314, LS-41548, SC-00635, SC-11263, SMR000349651, CAS-2592-95-2, KB-159798, ST2408893, TL8002087, TR-011763, FT-0601979, FT-0602216, FT-0652486, ST24038268, 2554-EP2269990A1, 2554-EP2269992A1, 2554-EP2270004A1, 2554-EP2272517A1, 2554-EP2272822A1, 2554-EP2272825A2, 2554-EP2272838A1, 2554-EP2272841A1, 2554-EP2275105A1, 2554-EP2275404A1, 2554-EP2275410A1, 2554-EP2277858A1, 2554-EP2280008A2, 2554-EP2281818A1, 2554-EP2281823A2, 2554-EP2284159A1, 2554-EP2284169A1, 2554-EP2284171A1, 2554-EP2286811A1, 2554-EP2287153A1, 2554-EP2287155A1, 2554-EP2287161A1, 2554-EP2287162A1, 2554-EP2287166A2, 2554-EP2289887A2, 2554-EP2289888A2, 2554-EP2289894A2, 2554-EP2292228A1, 2554-EP2292589A1, 2554-EP2292596A2, 2554-EP2292613A1, 2554-EP2292619A1, 2554-EP2292620A2, 2554-EP2292621A1, 2554-EP2292628A2, 2554-EP2295402A2, 2554-EP2295410A1, 2554-EP2295411A1, 2554-EP2295414A1, 2554-EP2295426A1, 2554-EP2295427A1, 2554-EP2298731A1, 2554-EP2298743A1, 2554-EP2298744A2, 2554-EP2298746A1, 2554-EP2298747A1, 2554-EP2298751A2, 2554-EP2298761A1, 2554-EP2298767A1, 2554-EP2298778A1, 2554-EP2301922A1, 2554-EP2301934A1, 2554-EP2301939A1, 2554-EP2302382A2, 2554-EP2302383A2, 2554-EP2305250A1, 2554-EP2305633A1, 2554-EP2305643A1, 2554-EP2305648A1, 2554-EP2305667A2, 2554-EP2305671A1, 2554-EP2305682A1, 2554-EP2305688A1, 2554-EP2308828A2, 2554-EP2308838A1, 2554-EP2308844A2, 2554-EP2308845A2, 2554-EP2308846A2, 2554-EP2308851A1, 2554-EP2308857A1, 2554-EP2308869A1, 2554-EP2308877A1, 2554-EP2308879A1, 2554-EP2311806A2, 2554-EP2311811A1, 2554-EP2311822A1, 2554-EP2311825A1, 2554-EP2311830A1, 2554-EP2311840A1, 2554-EP2311842A2, 2554-EP2314295A1, 2554-EP2314585A1, 2554-EP2314586A1, 2554-EP2316452A1, 2554-EP2316470A2, 2554-EP2371811A2, 2555-EP2269977A2, 2555-EP2269990A1, 2555-EP2270004A1, 2555-EP2270005A1, 2555-EP2270009A1, 2555-EP2272509A1, 2555-EP2272517A1, 2555-EP2272822A1, 2555-EP2272825A2, 2555-EP2272830A1, 2555-EP2272838A1, 2555-EP2272841A1, 2555-EP2272972A1, 2555-EP2272973A1, 2555-EP2275102A1, 2555-EP2275105A1, 2555-EP2275404A1, 2555-EP2275410A1, 2555-EP2275413A1, 2555-EP2277858A1, 2555-EP2277867A2, 2555-EP2277872A1, 2555-EP2280000A1, 2555-EP2280001A1, 2555-EP2280003A2, 2555-EP2280006A1, 2555-EP2280012A2, 2555-EP2281818A1, 2555-EP2281823A2, 2555-EP2284157A1, 2555-EP2284159A1, 2555-EP2284166A1, 2555-EP2284171A1, 2555-EP2286811A1, 2555-EP2287153A1, 2555-EP2287155A1, 2555-EP2287156A1, 2555-EP2287165A2, 2555-EP2287166A2, 2555-EP2289882A1, 2555-EP2289890A1, 2555-EP2289891A2, 2555-EP2289893A1, 2555-EP2289894A2, 2555-EP2292228A1, 2555-EP2292589A1, 2555-EP2292620A2, 2555-EP2292625A1, 2555-EP2292628A2, 2555-EP2295401A2, 2555-EP2295402A2, 2555-EP2295406A1, 2555-EP2295410A1, 2555-EP2295412A1, 2555-EP2295413A1, 2555-EP2295414A1, 2555-EP2295426A1, 2555-EP2295427A1, 2555-EP2295439A1, 2555-EP2298731A1, 2555-EP2298743A1, 2555-EP2298744A2, 2555-EP2298747A1, 2555-EP2298767A1, 2555-EP2298770A1, 2555-EP2298776A1, 2555-EP2298779A1, 2555-EP2301536A1, 2555-EP2301538A1, 2555-EP2301922A1, 2555-EP2301939A1, 2555-EP2305250A1, 2555-EP2305643A1, 2555-EP2305652A2, 2555-EP2305660A1, 2555-EP2305667A2, 2555-EP2305671A1, 2555-EP2305675A1, 2555-EP2305682A1, 2555-EP2305687A1, 2555-EP2305688A1, 2555-EP2305808A1, 2555-EP2308812A2, 2555-EP2308838A1, 2555-EP2308840A1, 2555-EP2308844A2, 2555-EP2308845A2, 2555-EP2308846A2, 2555-EP2308851A1, 2555-EP2308869A1, 2555-EP2308879A1, 2555-EP2308960A1, 2555-EP2311455A1, 2555-EP2311808A1, 2555-EP2311811A1, 2555-EP2311825A1, 2555-EP2311829A1, 2555-EP2311830A1, 2555-EP2311840A1, 2555-EP2311842A2, 2555-EP2314295A1, 2555-EP2314586A1, 2555-EP2316470A2, 2555-EP2316835A1, 2555-EP2371811A2, 2555-EP2374791A1, C-4569, 14972-EP2269610A2, 14972-EP2289510A1, 14972-EP2316457A1, 14972-EP2316458A1, 17260-EP2270006A1, 17260-EP2272827A1, 17260-EP2275414A1, 17260-EP2277861A1, 17260-EP2295401A2, 17260-EP2298750A1, 17260-EP2298772A1, 17260-EP2305660A1, 17260-EP2305668A1, 17260-EP2308839A1, 17260-EP2314586A1, 17260-EP2374790A1, 57276-EP2298769A1, 57276-EP2308878A2, 66972-EP2269990A1, 66972-EP2298731A1, 66972-EP2298772A1, 66972-EP2308839A1, 67162-EP2272848A1, 67162-EP2298772A1, 67162-EP2308839A1, 68140-EP2281818A1, 68140-EP2284166A1, 68140-EP2284178A2, 68140-EP2284179A2, 68140-EP2292625A1, 68140-EP2308874A1, 68140-EP2374791A1, 77893-EP2272846A1, 77893-EP2277868A1, 77893-EP2277869A1, 77893-EP2277870A1, 77893-EP2308866A1, 101142-EP2298779A1, 101142-EP2302382A2, 101142-EP2302383A2, 107607-EP2272830A1, 107607-EP2289880A1, 107607-EP2298746A1, 107607-EP2298761A1, 111041-EP2374791A1, AB-131/40192094, I01-0151, I14-7622, T0515-4929

Removed Synonyms

hydroxybenzotriazole, 1-Hydroxybenzotriazole hydrate, CID75771, 1h-1,2,3-benzotriazol-1-ol hydrate, 1H-Benzo[d][1,2,3]triazol-1-ol xhydrate, A7025, H0468, 4-26-00-00095 (Beilstein Handbook Reference), 123333-53-9, 40150-21-8, 80029-43-2, 84249-60-5

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