N,N'-Diacetyl-1,4-phenylenediamine

Base Information

• Chemical Name: N,N'-Diacetyl-1,4-phenylenediamine
• CAS No.: 140-50-1
• Molecular Formula: C10H12N2O2
• Molecular Weight: 192.217
• Hs Code.: 2924299090
• European Community (EC) Number: 205-417-3
• NSC Number: 401116
• UNII: I96A01798W
• DSSTox Substance ID: DTXSID2059695
• Nikkaji Number: J79.459G
• Wikidata: Q27280599
• Mol file: 140-50-1.mol

Synonyms:DAPPD;N,N'-diacetyl-p-phenylenediamine

Chemical Property of N,N'-Diacetyl-1,4-phenylenediamine

Chemical Property:

• Appearance/Colour: Dark yellow crystals
• Melting Point: > 300 °C
• Boiling Point: 483.8 °C at 760 mmHg
• PKA: 14.29±0.70(Predicted)
• Flash Point: 219.6 °C
• PSA: 58.20000
• Density: 1.235 g/cm³
• LogP: 1.74940
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 192.089877630
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

98% ^*data from raw suppliers

N,N'-Diacetyl-1,4-phenylenediamine >98.0%(GC)(N) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=O)NC1=CC=C(C=C1)NC(=O)C

Technology Process of N,N'-Diacetyl-1,4-phenylenediamine

There total 26 articles about N,N'-Diacetyl-1,4-phenylenediamine 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: 96.0%

para-dinitrobenzene (100-25-4) + ethyl acetate (141-78-6) → N,N'-diacetyl-1,4-phenylenediamine (140-50-1)

Guidance literature:

para-dinitrobenzene; With sodium tetrahydroborate; In ethyl acetate;

ethyl acetate; With bis(dimethylglyoximato)copper(II); for 4h; Reflux;

DOI:10.1002/jccs.201800325

Reference yield: 95.0%

1-(4-aminophenyl)ethanone oxime (56072-03-8) → N,N'-diacetyl-1,4-phenylenediamine (140-50-1)

Guidance literature:

With tin(II) chloride dihdyrate; tetra-(n-butyl)ammonium iodide; In acetonitrile; for 2h; Molecular sieve; Reflux;

Reference yield: 94.0%

N-(4-Nitrophenyl)acetamide (104-04-1) + acetic anhydride (108-24-7) → N,N'-diacetyl-1,4-phenylenediamine (140-50-1)

Guidance literature:

N-(4-Nitrophenyl)acetamide; With sodium tetrahydroborate; water; In neat (no solvent); at 20 ℃; for 0.0166667h;

acetic anhydride; In neat (no solvent); at 40 ℃; for 0.0666667h; Reagent/catalyst;

DOI:10.1007/s11164-018-3559-x

upstream raw materials:

1,4-Diacetylbenzene

para-dinitrobenzene

acetic anhydride

p-phenylenediammonium sulfate

Downstream raw materials:

1,4-bis-NN-(dimethylaminomethyleneamino)benzene

N-[2-(phthalimidomethyl)-1,4-diacetyl]phenylenediamine

3-phenyl-[4,7]phenanthroline

3-p-tolyl-4,7-phenanthroline

Refernces

• 1、 Peisino, Lucas E.,Camargo Solorzano, Gloria P.,Budén, María E.,Pierini. "Iterative double cyclization reaction by SRN1 mechanism. A theoretical interpretation of the regiochemical outcome of diazaheterocycles". . p. 36374 - 36384. Retrieved 2015.
• 2、 -. "Compound containing phenanthridine fragment and synthesis method of compound". Paragraph 0014-0015. . Retrieved 2021/04/26.
• 3、 Gurjar, Jitendra,Fokin, Valery V.. "Sulfuryl Fluoride Mediated Synthesis of Amides and Amidines from Ketoximes via Beckmann Rearrangement". supporting information. p. 10402 - 10405. Retrieved 2020/07/25.