136-85-6

Basic information

• Product Name: 5-Methyl-1H-benzotriazole
• Synonyms: 5-Methyl-1H-benzo-1,2,3-triazole;5-methyl-1h-benzotriazol;m-Tolylazoimide;Retrocure G;Vulkalent TM;TIMTEC-BB SBB007732;5MBT;5-METHYL-1H-BENZOTRIAZOLE
• CAS NO: 136-85-6
• Molecular Formula: C₇H₇N₃
• Molecular Weight: 133.15
• EINECS: 205-265-8
• Product Categories: Industrial/Fine Chemicals;Benzotriazoles;Building Blocks;Heterocyclic Building Blocks;Aromatics;Heterocycles;Inhibitors
• Mol File: 136-85-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 80-82 °C(lit.)
• Boiling Point: 210-212 °C12 mm Hg(lit.)
• Flash Point: 210-212°C/12mm
• Appearance: Cream to beige/Crystalline Powder
• Density: 1.1873 (rough estimate)
• Vapor Pressure: 0.001Pa at 25℃
• Refractive Index: 1.5341 (estimate)
• Storage Temp.: Refrigerator
• PKA: 8.74±0.40(Predicted)
• Water Solubility: 6.0 g/L (25 ºC)
• BRN: 116658
• CAS DataBase Reference: 5-Methyl-1H-benzotriazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Methyl-1H-benzotriazole(136-85-6)
• EPA Substance Registry System: 5-Methyl-1H-benzotriazole(136-85-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-37-22
• Safety Statements: 26-36-38
• WGK Germany: 3
• RTECS: DM1400000
• TSCA: Yes
• Hazardous Substances Data: 136-85-6(Hazardous Substances Data)

Usage

Chemical Properties

cream to beige crystalline powder

Uses

Different sources of media describe the Uses of 136-85-6 differently. You can refer to the following data:
1. A potential nitrification inhibitor of urea fertilizer in agricultural soils.
2. 5-Methyl-1H-benzotriazole was used in determination of benzothiazoles and benzotriazoles in waste water samples by GC-MS. It is also used as a potential nitrification inhibitor of urea fertilizer in agricultural soils.

Definition

ChEBI: A member of the class of benzotriazoles that is 1H-benzotriazole substituted by a methyl group at position 5.

General Description

5-Methyl-1H-benzotriazole is an active component of aircraft deicing and anti-icing fluid. It prevents the corrosion of copper and brass in a variety of corrosive environments.

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

Synthetic route

4-methyl-1,2-diaminobenzene (496-72-0) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With K10 Montmorillonite Clay; sodium nitrite In neat (no solvent, solid phase) at 110℃; for 1h; Microwave irradiation; Green chemistry;	98%
With tert.-butylnitrite In acetonitrile at 27 - 29℃; for 0.25h;	93%
With acetic acid In water at 70 - 80℃; for 0.533333h;	80%

1-azido-2-bromo-4- methylbenzene → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -85 - 20℃;	87%

1-azido-2-iodo-4-methyl-benzene (122099-10-9) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane at -85 - 20℃;	82%

5-methyl-1H-benzo[d][1,2,3]triazol-1-ol (26198-27-6) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With 2,3-dimethyl-2,3-butane diol; bis(N,N-dimethylacetamide)dichloridodioxidomolybdenum(VI) In N,N-dimethyl acetamide at 120℃; for 0.25h; Temperature; Microwave irradiation; Sealed tube; Green chemistry;	81%

4-methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate (262373-15-9) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With sodium azide; 18-crown-6 ether; cesium fluoride In acetonitrile at 70℃; for 12h; Inert atmosphere;	51%

6-Methyl-1-acetylbenzotriazole (129354-65-0) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Verseifen;

5-methyl-benzotriazole-1-carboxylic acid anilide (72976-72-8) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Erhitzen;

4-Methyl-benzene-1,2-diamine; hydrochloride (636-24-8) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Diazotization;

Acetic acid 5-methyl-benzotriazol-1-ylmethyl ester (116577-45-8) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With sodium metabisulfite; sodium sulfite In water; acetonitrile at 25℃; Rate constant; absence of sulfites;

4-Oxo-pentanoic acid 5-methyl-benzotriazol-1-ylmethyl ester (96026-15-2) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With sodium metabisulfite; sodium sulfite In water; acetonitrile at 25℃; Rate constant; absence of sulfites;

1-benzohydroximoyl-5-methylbenzotriazole (86255-39-2) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With hydrogenchloride for 2h; Heating; Yield given;

1-acetyl-5-methyl-benztriazole → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With sulfuric acid
With hydrogenchloride

1-acetyl-6-methyl-benztriazole → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Verseifen;

1-oxy-6-methyl-benztriazole → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
With phosphorus; hydrogen iodide at 140 - 150℃;

hydrogenchloride (7647-01-0) + 5-Methyl-1-acetylbenzotriazole (129354-64-9) + water (7732-18-5) → 5(6)-methylbenzotriazole (136-85-6)

5-Methyl-1-acetylbenzotriazole (129354-64-9) + sulfuric acid (7664-93-9) + water (7732-18-5) → 5(6)-methylbenzotriazole (136-85-6)

5(?)-methyl-benztriazole-carboxylic acid-(1)-anilide → 5(6)-methylbenzotriazole (136-85-6)

5-methyl-benzotriazole-1-carboxylic acid anilide (72976-72-8) + alkaline solution → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Erhitzen;

6-methyl-3H-benzotriazole-1-oxide + hydrogen iodide (10034-85-2) + red phosphorus → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
at 140 - 150℃;

hydrogenchloride (7647-01-0) + 4-methyl-1,2-diaminobenzene (496-72-0) + sodium nitrite → 5(6)-methylbenzotriazole (136-85-6)

sulfuric acid (7664-93-9) + 4-methyl-1,2-diaminobenzene (496-72-0) + sodium nitrite → 5(6)-methylbenzotriazole (136-85-6)

N-(2-amino-4-methylphenyl)benzamide oxime (86255-34-7) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: conc. HCl, NaNO2 / H2O / 1 h / Ambient temperature 2: conc. HCl / 2 h / Heating View Scheme

2-chloro-4-methyl-1-nitrobenzene (38939-88-7) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrazine hydrate / ethanol / 36 h / Reflux 2: 2,3-dimethyl-2,3-butane diol; bis(N,N-dimethylacetamide)dichloridodioxidomolybdenum(VI) / N,N-dimethyl acetamide / 0.25 h / 120 °C / Microwave irradiation; Sealed tube; Green chemistry View Scheme

2-iodo-4-methylaniline (29289-13-2) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / water / Heating 1.2: 1 h / 0 - 5 °C 1.3: 4 h / 10 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -85 - 20 °C View Scheme

2-bromo-p-toluidine (583-68-6) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sulfuric acid / water / Heating 1.2: 1 h / 0 - 5 °C 1.3: 4 h / 10 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / -85 - 20 °C View Scheme

p-toluidine (106-49-0) → 5(6)-methylbenzotriazole (136-85-6)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: N-Bromosuccinimide / dichloromethane / 0 - 5 °C / Schlenk technique; Inert atmosphere 2.1: sulfuric acid / water / Heating 2.2: 1 h / 0 - 5 °C 2.3: 4 h / 10 - 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / -85 - 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: sodium hydrogencarbonate; iodine / dichloromethane; water / 72 h / Schlenk technique; Inert atmosphere 2.1: sulfuric acid / water / Heating 2.2: 1 h / 0 - 5 °C 2.3: 4 h / 10 - 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / -85 - 20 °C View Scheme

5(6)-methylbenzotriazole (136-85-6) → 5-methyl-4-nitrobenzotriazole (31995-60-5)

Conditions	Yield
With nitric acid In conc. sulphuric acid	94%
With sulfuric acid; nitric acid	90%

5(6)-methylbenzotriazole (136-85-6) + Methyl phenyldiazoacetate (22979-35-7) → methyl 2-(5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)-2-phenylacetate

Conditions	Yield
With Rh2(PTA)4 In dichloromethane at 20℃; for 4h; Schlenk technique; Inert atmosphere; regioselective reaction;	92%

5(6)-methylbenzotriazole (136-85-6) + 4-tert-Butylstyrene (1746-23-2) → 2-(1-(4-tert-butylphenyl)vinyl)-5-methyl-2H-benzo[d][1,2,3]triazole

Conditions	Yield
Stage #1: 5(6)-methylbenzotriazole; 4-tert-Butylstyrene With N-iodo-succinimide In chloroform at 30℃; for 0.0833333h; Stage #2: With potassium carbonate In methanol for 12h; Reflux; regioselective reaction;	88%

5(6)-methylbenzotriazole (136-85-6) + 3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione (67082-95-5) → 1-(2-methyl-5-((5-methyl-2H-benzo[d][1,2,3]triazol-2-yl)(phenyl)methyl)furan-3-yl)ethan-1-one

Conditions	Yield
With bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]} In 1,2-dichloro-ethane at 20℃; for 2h; Inert atmosphere; Schlenk technique; regioselective reaction;	87%

5(6)-methylbenzotriazole (136-85-6) + dimethyl acetylenedicarboxylate (762-42-5) + triphenylphosphine (603-35-0) → dimethyl 2-(5-methylbenzotriazol-1-yl)-3-(triphenylphosphanylidene)butanedioate

Conditions	Yield
With polyacrylamide In water at 20℃;	86%

5(6)-methylbenzotriazole (136-85-6) + 1-Bromooctadecane (112-89-0) → 1-octadecyl-5-methyl-1H-benzo[1,2,3]triazol-1-ium bromide

Conditions	Yield
In acetone for 36h; Reflux;	85%

5(6)-methylbenzotriazole (136-85-6) + 1-Bromooctadecane (112-89-0) → 1-octadecyl-5-methyl-1H-benzo[d][1,2,3]triazole-1- ium bromide

Conditions	Yield
In acetone at 70 - 80℃; for 36h;	85%

5(6)-methylbenzotriazole (136-85-6) + cyclohexanone (108-94-1) → C19H25N3O

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In toluene at 20℃; for 24h;	84%

5(6)-methylbenzotriazole (136-85-6) + 4-methyl-7-(oxiran-2-ylmethoxy)-2H-1-benzopyran-2-one (24689-27-8) → 7-(2-hydroxy-3-(5-methyl-1H-benzo[d][1,2,3]triazol-1-yl)propoxy)-4-methyl-2H-chromen-2-one

Conditions	Yield
Stage #1: 5(6)-methylbenzotriazole With potassium carbonate In ethanol at 60℃; for 1h; Stage #2: 4-methyl-7-(oxiran-2-ylmethoxy)-2H-1-benzopyran-2-one In ethanol at 20 - 70℃;	83.6%

5(6)-methylbenzotriazole (136-85-6) → 5-methyl-1-nitrobenzotriazole

Conditions	Yield
With Iron(III) nitrate nonahydrate; tetrabutylammonium tetrafluoroborate In acetonitrile at 70℃; Inert atmosphere; Electrolysis; Green chemistry;	83%

5(6)-methylbenzotriazole (136-85-6) + 1-dodecylbromide (143-15-7) → 1-dodecyl-5-methyl-1H-benzo[d][1,2,3]triazole-1- ium bromide

Conditions	Yield
In acetone for 36h; Reflux;	82%
In acetone at 70 - 80℃; for 36h;	82%

5(6)-methylbenzotriazole (136-85-6) + N-ethyl-N-phenyl carbamoyl chloride (33758-39-3) → 1-(N-Ethyl-N-phenylcarbamoyl)-5-methylbenzotriazole

Conditions	Yield
In water; triethylamine	78%

5(6)-methylbenzotriazole (136-85-6) + Methyl phenyldiazoacetate (22979-35-7) → methyl 2-(5-methyl-1H-benzo[d][1,2,3]triazol-1-yl)-2-phenylacetate

Conditions	Yield
With tert.-butylnitrite; p-benzoquinone In dichloromethane at 20℃; for 48h; Irradiation;	78%

5(6)-methylbenzotriazole (136-85-6) + NAD (53-84-9) → adenosine 5′-diphosphate ribose (47774-99-2, 47775-00-8, 88495-30-1) + 5-methyl-1H-benzotriazole adenine dinucleotide ammonium salt

Conditions	Yield
With sodium hydroxide; NAD nucleosidase; tris hydrochloride In water at 37℃; for 20h; pH: 7.2;	A n/a B 76%

5(6)-methylbenzotriazole (136-85-6) + NAD (53-84-9) → C22H28N8O13P2 (112926-09-7)

Conditions	Yield
porcine brain NADase	76%

5(6)-methylbenzotriazole (136-85-6) → 5-methyl-4,6,7-tribromo-1H-benzotriazole (1240784-76-2)

Conditions	Yield
With bromine; nitric acid In water at 130℃; for 24h;	76%

5(6)-methylbenzotriazole (136-85-6) + cyclohexylallene (5664-17-5) → 2-(1-cyclohexylallyl)-5-methyl-2H-benzo[d][1,2,3]triazole (1643833-48-0)

Conditions	Yield
With chloro(1,5-cyclooctadiene)rhodium(I) dimer; bis[2-(diphenylphosphino)phenyl] ether In 1,2-dichloro-ethane at 80℃; for 18h; Schlenk technique; Inert atmosphere; regioselective reaction;	72%

5(6)-methylbenzotriazole (136-85-6) + 1,3-chlorobromopropane (109-70-6) → 1-(3-chloropropyl)-5-methyl-1H-benzo[d]-[1,2,3]triazole

Conditions	Yield
With potassium carbonate In MeCN at 20℃; for 96h;	72%

5(6)-methylbenzotriazole (136-85-6) + triphenylphosphine (603-35-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 2-(5-methylbenzotriazol-1-yl)-3-(triphenylphosphanylidene)butanedioate

Conditions	Yield
With polyacrylamide In water at 20℃;	71%

5(6)-methylbenzotriazole (136-85-6) + 1-bromo-hexane (111-25-1) → 1-hexyl-5-methyl-1H-benzo[d][1,2,3]triazole-1- ium bromide

Conditions	Yield
In acetone for 36h; Reflux;	71%
In acetone at 70 - 80℃; for 36h;	71%

styrene (292638-84-7) + 5(6)-methylbenzotriazole (136-85-6) → 5-methyl-2-(1-phenylvinyl)-2H-benzo[d][1,2,3]triazole

Conditions	Yield
With dipotassium peroxodisulfate; trimethylsilan; diphenyl diselenide In 1,4-dioxane at 120℃;	70%

5(6)-methylbenzotriazole (136-85-6) + thioxanthene (261-31-4) → 5-Methyl-1-(9H-thioxanthen-9-yl)-1H-benzotriazole

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene for 4h; Heating;	66%

5(6)-methylbenzotriazole (136-85-6) → 1-(5-methylbenzatriazolyl) phosphoric acid

Conditions	Yield
With phosphorus pentoxide In chloroform for 3h; Heating;	64%
With pyrophosphoric acid In tetrachloromethane

5(6)-methylbenzotriazole (136-85-6) + 6-indolyl-(4-methoxyphenyl)methanol → (R)-2-((1H-indol-6-yl)(4-methoxyphenyl)methyl)-5-methyl-2H-benzo[d][1,2,3]triazole

Conditions	Yield
With chiral phosphoric acid (CPA) In 1,2-dichloro-ethane at 25℃; for 144h;	64%

5(6)-methylbenzotriazole (136-85-6) + ethanol (64-17-5) → 1-(1-ethoxyethyl)-5-methyl-1H-benzo[d][1,2,3]triazole

Conditions	Yield
With tert.-butylhydroperoxide In decane at 120℃; for 12h; Schlenk technique; Sealed tube;	62%

5(6)-methylbenzotriazole (136-85-6) + xanthene (92-83-1) → 5-methyl-1-(9H-xanthen-9-yl)-1H-benzo[d][1,2,3]triazole

Conditions	Yield
With methanesulfonic acid; tetrabutylammonium tetrafluoroborate In acetonitrile at 20℃; for 2h; Electrochemical reaction;	60%

Upstream product

• 262373-15-9 4-methyl-2-(trimethylsilyl)phenyl trifluoromethanesulfonate 
• 106-49-0 p-toluidine 
• 583-68-6 2-bromo-p-toluidine 
• 122099-10-9 1-azido-2-iodo-4-methyl-benzene 
• 29289-13-2 2-iodo-4-methylaniline 
• 26198-27-6 5-methyl-1H-benzo[d][1,2,3]triazol-1-ol 
• 38939-88-7 2-chloro-4-methyl-1-nitrobenzene 
• 86255-34-7 N-(2-amino-4-methylphenyl)benzamide oxime 
• 7664-93-9 sulfuric acid 
• 496-72-0 4-methyl-1,2-diaminobenzene 
• 7647-01-0 hydrogenchloride 
• 10034-85-2 hydrogen iodide 
• 72976-72-8 5-methyl-benzotriazole-1-carboxylic acid anilide 
• 129354-64-9 5-Methyl-1-acetylbenzotriazole 

Downstream Products

• 31995-60-5 5-methyl-4-nitrobenzotriazole 
• 130385-00-1 5-methyl-1-benzotriazolecarbonyl chloride 
• 23814-12-2 1h-benzotriazole-5-carboxylic acid 
• 4546-95-6 1H-1,2,3-triazole-4,5-dicarboxylic acid 
• 72976-72-8 5-methyl-benzotriazole-1-carboxylic acid anilide 
• 106429-67-8 (1H-benzo[d][1,2,3]triazol-5-yl)methanol 

Related news

The influence of chloride ions on the anti-corrosion ability of binary inhibitor system of 5-Methyl-1H-benzotriazole (cas 136-85-6) and potassium sorbate in sulfuric acid solution09/30/2019

In this work, the effect of chloride ions on copper corrosion behavior in an acidic sulfate solution, in the presence of binary inhibitor system of azoles and potassium sorbate was studied. Electrochemical measurements, weight loss measurements and surface analysis (SEM/EDS) were used in this in...detailed

Identification of ozonation by-products of 4- and 5-Methyl-1H-benzotriazole (cas 136-85-6) during the treatment of surface water to drinking water09/29/2019

During the treatment of surface water to drinking water, ozonation is often used for disinfection and to remove organic trace substances, whereby oxidation by-products can be formed. Here we use the example of tolyltriazole to describe an approach for identifying relevant oxidation by-products i...detailed

The influence of synergistic effects of 5-Methyl-1H-benzotriazole (cas 136-85-6) and potassium sorbate as well as 5-Methyl-1H-benzotriazole (cas 136-85-6) and gelatin on the copper corrosion in sulphuric acid solution10/01/2019

The synergistic inhibition effect of the 5-methyl-1H-benzotriazole (MBTAH)/1H-benzotriazole (BTAH) with potassium sorbate and gelatin on the copper corrosion in an acidic sulphate solution was investigated by electrochemical methods and weight loss measurements. According to the obtained results...detailed

Relevant articles and documents

Microwave-assisted solid phase diazotation: A method for the environmentally benign synthesis of benzotriazoles

A novel environmentally benign approach based on microwave-assisted solid phase diazotation to convert o-phenylendiamines to substituted benzotriazoles is described. Excellent yields were obtained for a phenylenediamines proving the efficacy of the method. The reaction was carried out in the solid phase under microwave irradiation taking advantage of the strong microwave absorption capability of K-10 montmorillonite that acted as a catalyst and medium in one. The catalyst is recyclable, and the reaction occurs with high efficiency and does not produce any harmful waste.

Making endo-cyclizations favorable again: A conceptually new synthetic approach to benzotriazoles via azide group directed lithiation/cyclization of 2-azidoaryl bromides

Although benzotriazoles are important and ubiquitous, currently there is only one conceptual approach to their synthesis: bridging the two ortho-amino groups with an electrophilic nitrogen atom. Herein, we disclose a new practical alternative-the endo-cyclization of 2-azidoaryl lithiums obtained in situ from 2-azido-aryl bromides. The scope of the reaction is illustrated using twenty-four examples with a variety of alkyl, alkoxy, perfluoroalkyl, and halogen substituents. We found that the directing effect of the azide group allows selective metal-halogen exchange in aryl azides containing several bromine atoms. Furthermore, (2-bromophenyl)diazomethane undergoes similar cyclization to give an indazole. Thus, cyclizations of aryl lithiums containing an ortho-X = Y = Z group emerge as a new general approach for the synthesis of aromatic heterocycles. DFT computations suggested that the observed endo-selectivity applies to the anionic cyclizations of other functionalities that undergo "1,1-additions" (i.e., azides, diazo compounds, and isonitriles). In contrast, cyclizations with the heteroatomic functionalities that follow the "1,2-addition" pattern (cyanates, thiocyanates, isocyanates, isothiocyanates, and nitriles) prefer the exo-cyclization path. Hence, such reactions expand the current understanding of stereoelectronic factors in anionic cyclizations.

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