N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

Base Information

• Chemical Name: N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester
• CAS No.: 226065-32-3
• Molecular Formula: C12H15N3O2
• Molecular Weight: 233.27
• DSSTox Substance ID: DTXSID10459469
• Nikkaji Number: J1.109.147D
• Wikidata: Q82283244
• Mol file: 226065-32-3.mol

Synonyms:N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester;226065-32-3;SCHEMBL3868314;DTXSID10459469;RYBYYDFXTZLPJJ-UHFFFAOYSA-N;N-(4-Cyanophenyl)carbazic acid tert-butyl ester;tert-butyl 1-(4-cyanophenyl)hydrazinecarboxylate

Chemical Property of N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

Chemical Property:

• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 233.116426730
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N(C1=CC=C(C=C1)C#N)N

Technology Process of N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester

There total 4 articles about N-(4-Cyano-phenyl)-hydrazinecarboxylic Acid tert-butyl Ester 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: 81.0%

t-butoxycarbonylhydrazine (870-46-2) + 4-bromobenzenecarbonitrile (623-00-7) → tert-butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate (226065-32-3)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; caesium carbonate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 100 ℃; for 16h;

DOI:10.1016/S0040-4039(99)00561-4

Reference yield: 78.0%

t-butoxycarbonylhydrazine (870-46-2) + 4-iodobenzonitrile (3058-39-7) → tert-butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate (226065-32-3)

Guidance literature:

With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 4h;

DOI:10.1021/ol0168216

Reference yield:

4-Cyanochlorobenzene (623-03-0) + t-butoxycarbonylhydrazine (870-46-2) → N'-(4-cyanophenyl)hydrazinecarboxylic acid tert-butyl ester (848153-28-6) + tert-butyl 1-(4-cyanophenyl)hydrazine-1-carboxylate (226065-32-3)

Guidance literature:

With nickel(II) bromide trihydrate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dimethyl sulfoxide; at 120 ℃; for 0.166667h; Irradiation; Flow reactor;

DOI:10.1039/d0cc06787c

upstream raw materials:

t-butoxycarbonylhydrazine

4-bromobenzenecarbonitrile

4-iodobenzonitrile

4-Cyanochlorobenzene

Downstream raw materials:

tert-butyl N-(4-cyanophenyl)carbamate

Refernces

• 1、 Mata, Alejandro,Tran, Duc N.,Weigl, Ulrich,Williams, Jason D.,Kappe, C. Oliver. "Continuous flow synthesis of arylhydrazines: via nickel/photoredox coupling of tert -butyl carbazate with aryl halides". supporting information. p. 14621 - 14624. Retrieved 2020/12/02.
• 2、 Wang, Zhongren,Skerlj, Renato T.,Bridger, Gary J.. "Regioselective synthesis of aryl hydrazides by palladium-catalyzed coupling of t-butylcarbazate with substituted aryl bromides". . p. 3543 - 3546. Retrieved 2007/10/03.