N,N'-Diacetylbenzidine

Base Information

• Chemical Name: N,N'-Diacetylbenzidine
• CAS No.: 613-35-4
• Molecular Formula: C16H16 N2 O2
• Molecular Weight: 268.315
• Hs Code.: 2924299090
• European Community (EC) Number: 210-338-2
• ICSC Number: 1678
• NSC Number: 12409,4717
• UNII: 2EE5599GQS
• DSSTox Substance ID: DTXSID9036854
• Nikkaji Number: J36.102J
• Wikidata: Q26840865
• ChEMBL ID: CHEMBL1567221
• Mol file: 613-35-4.mol

Synonyms:N,N'-diacetylbenzidine

Chemical Property of N,N'-Diacetylbenzidine

Chemical Property:

• Melting Point: 317°C
• Refractive Index: 1.6240 (estimate)
• Boiling Point: 411.48°C (rough estimate)
• PKA: 14.60±0.70(Predicted)
• Flash Point: 251.9oC
• PSA: 58.20000
• Density: 1.1028 (rough estimate)
• LogP: 3.41640
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly)
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 268.121177757
• Heavy Atom Count: 20
• Complexity: 306

Purity/Quality:

99.5% ^*data from raw suppliers

Diacetylbenzidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Benzidine and Derivatives
• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)C2=CC=C(C=C2)NC(=O)C
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed.
• Effects of Short Term Exposure: May cause mechanical irritation to the eyes and respiratory tract.
• Effects of Long Term Exposure: The substance may have effects on the blood and kidneys. This may result in the formation of methaemoglobin, anaemia and kidney impairment. This substance is possibly carcinogenic to humans.
• Uses: Diacetylbenzidine (cas# 613-35-4) is a compound useful in organic synthesis.

Technology Process of N,N'-Diacetylbenzidine

There total 15 articles about N,N'-Diacetylbenzidine 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: 100.0%

acetic anhydride (108-24-7) + p,p'-diaminobiphenyl (92-87-5) → N,N'-Diacetylbenzidin (613-35-4)

Guidance literature:

DOI:10.1016/0165-1218(93)90027-B

Reference yield: 85.0%

4-Acetamido-1-iodobenzene (622-50-4) → N,N'-Diacetylbenzidin (613-35-4)

Guidance literature:

With dipotassium hydrogenphosphate; digold(I)bis(diphenylphosphinomethane)dichloride; triethylamine; In methanol; acetonitrile; for 16h; Inert atmosphere; UV-irradiation;

DOI:10.1021/acs.orglett.6b02021

Reference yield: 50.0%

p-acetylaminobenzenesulfonyl chloride (121-60-8) → N,N'-Diacetylbenzidin (613-35-4)

Guidance literature:

With copper(l) iodide; palladium diacetate; sodium hydrogencarbonate; triphenylphosphine; silver carbonate; In 1,4-dioxane; for 4h; Reflux; Schlenk technique;

DOI:10.1002/cjoc.201400868

upstream raw materials:

acetic anhydride

acetic acid

p,p'-diaminobiphenyl

diphenyl hydrazine

Downstream raw materials:

3-nitro-benzidine

N4,N4’-di([1,1‘-biphenyl]-4-yl)-[1,1‘-biphenyl]-4,4’-diamine

N₄,N₄'-di(naphthalen-1-yl)-[1,1'-biphenyl]-4,4'-diamine

N,N’-bis(2-naphthyl)benzidine

Refernces

• 1、 Vergura, Stefania,Scafato, Patrizia,Belviso, Sandra,Superchi, Stefano. "Absolute Configuration Assignment from Optical Rotation Data by Means of Biphenyl Chiroptical Probes". supporting information. p. 5682 - 5690. Retrieved 2019/03/17.
• 2、 Tran, Huy,McCallum, Terry,Morin, Mathieu,Barriault, Louis. "Homocoupling of iodoarenes and bromoalkanes using photoredox gold catalysis: A light enabled Au(III) reductive elimination". supporting information. p. 4308 - 4311. Retrieved 2016/09/09.