1-(Isocyanomethyl)-1H-benzotriazole

Base Information

• Chemical Name: 1-(Isocyanomethyl)-1H-benzotriazole
• CAS No.: 87022-42-2
• Molecular Formula: C8H6N4
• Molecular Weight: 158.162
• Hs Code.: 2933990090
• European Community (EC) Number: 623-419-6
• DSSTox Substance ID: DTXSID20397045
• Nikkaji Number: J534.110H
• Wikidata: Q82198066
• Mol file: 87022-42-2.mol

Synonyms:1-(Isocyanomethyl)-1H-benzotriazole;87022-42-2;1-(isocyanomethyl)benzotriazole;1-(Isocyanidomethyl)-1H-benzotriazole;1H-Benzotriazol-1-ylmethyl isocyanide;1-(isocyanomethyl)-1H-benzo[d][1,2,3]triazole;SCHEMBL386919;DTXSID20397045;benzotriazol-1-yl methylisocyanide;MFCD00961633;AKOS015889196;AKOS024365012;(1H-Benzotriazol-1-yl)methyl Isocyanide;1H-Benzotriazol-1-ylmethyl isocyanide, 94%;FT-0642060;I0455;N10047

Chemical Property of 1-(Isocyanomethyl)-1H-benzotriazole

Chemical Property:

• Melting Point: 80-84 °C(lit.)
• PSA: 30.71000
• LogP: 0.53880
• Storage Temp.: 2-8°C
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 158.059246208
• Heavy Atom Count: 12
• Complexity: 206

Purity/Quality:

98%,99%, ^*data from raw suppliers

1-(Isocyanomethyl)-1H-benzotriazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 14-26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: [C-]#[N+]CN1C2=CC=CC=C2N=N1
• Uses: Reactant for:Passerini condensationUgi type reactionsHeterocyclization with iminesPreparation of silver (isocyanomethyl)benzotriazole polymeric complex

Technology Process of 1-(Isocyanomethyl)-1H-benzotriazole

There total 3 articles about 1-(Isocyanomethyl)-1H-benzotriazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 76.0%

1-(formylaminoethyl)benzotriazole (87022-36-4) → 1-(isocyanomethyl)-1H-benzo[d][1,2,3]triazole (87022-42-2)

Guidance literature:

With tetrachloromethane; triethylamine; triphenylphosphine; In dichloromethane; for 1h; Heating;

Reference yield:

1,2,3-Benzotriazole (95-14-7,27556-51-0) → 1-(isocyanomethyl)-1H-benzo[d][1,2,3]triazole (87022-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 93 percent / potassium hydroxide / methanol / 8 h / Heating

2: 76 percent / Ph₃P, CCl₄, triethylamine / CH₂Cl₂ / 1 h / Heating

With tetrachloromethane; potassium hydroxide; triethylamine; triphenylphosphine; In methanol; dichloromethane;

Reference yield:

1,2,3-Benzotriazole (95-14-7,27556-51-0) → 1-(isocyanomethyl)-1H-benzo[d][1,2,3]triazole (87022-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 63 percent / toluene / Heating

2: 66 percent / (i-Pr)2NH, POCl₃ / CH₂Cl₂ / 1 h / 0 °C

With diisopropylamine; trichlorophosphate; In dichloromethane; toluene;

upstream raw materials:

1-(formylaminoethyl)benzotriazole

1,2,3-Benzotriazole

Refernces

• 1、 Katritzky,Chen,Yannakopoulou,Lue. "Benzotriazol-1-ylmethyl isocyanide, a new synthon for CH-N=C transfer. Syntheses of α-hydroxyaldehydes, 4-ethoxy-2-oxazolines and oxazoles". . p. 6657 - 6660. Retrieved 2007/10/02.