2-[(4-Nitrophenyl)hydrazinylidene]propanedinitrile

Base Information

• Chemical Name: 2-[(4-Nitrophenyl)hydrazinylidene]propanedinitrile
• CAS No.: 3722-12-1
• Molecular Formula: C9H5N5O2
• Molecular Weight: 215.171
• DSSTox Substance ID: DTXSID80190711
• Nikkaji Number: J41.629K,J502.709H
• ChEMBL ID: CHEMBL1544901
• Mol file: 3722-12-1.mol

Synonyms:3722-12-1;2-[(4-nitrophenyl)hydrazinylidene]propanedinitrile;MLS000779896;Mesoxalonitrile, (P-nitrophenyl)hydrazone;SMR000420077;MALONONITRILE, (p-NITROPHENYL)HYDRAZONE;p-Nitrophenylhydrazonomalononitrile;BRN 1842828;1-CYANO-N-(4-NITROPHENYL)METHANECARBOHYDRAZONOYL CYANIDE;2-[(4-Nitro-phenyl)-hydrazono]-malononitrile;Propanedinitrile, ((4-nitrophenyl)hydrazono)-;Propanedinitrile, 2-[2-(4-nitrophenyl)hydrazinylidene]-;cid_19495;CHEMBL1544901;BDBM58179;DTXSID80190711;HMS2779N07;4-nitrophenyl-hydrazonomalononitrile;STK535116;AKOS003581666;2-(4-Nitrophenyl)hydrazonomalononitrile;NCGC00246375-01;LS-88983;2-[(4-nitrophenyl)hydrazono]malononitrile;[2-(4-nitrophenyl)hydrazinylidene]propanedinitrile;1-(4-Nitrophenyl)-2-(dicyanomethylene)hydrazinide;4-15-00-00368 (Beilstein Handbook Reference);SR-01000773377;SR-01000773377-2

Chemical Property of 2-[(4-Nitrophenyl)hydrazinylidene]propanedinitrile

Chemical Property:

• Vapor Pressure: 4.7E-06mmHg at 25°C
• Boiling Point: 382.5°C at 760 mmHg
• Flash Point: 185.1°C
• Density: 1.36g/cm³
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 215.04432442
• Heavy Atom Count: 16
• Complexity: 367

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1NN=C(C#N)C#N)[N+](=O)[O-]

Technology Process of 2-[(4-Nitrophenyl)hydrazinylidene]propanedinitrile

There total 12 articles about 2-[(4-Nitrophenyl)hydrazinylidene]propanedinitrile 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: 98.0%

4-nitro-aniline (100-01-6,104810-17-5) + malononitrile (109-77-3) → 4-nitrophenylhydrazonopropanedinitrile (3722-12-1)

Guidance literature:

4-nitro-aniline; With hydrogenchloride; sodium nitrite; In water; at 0 ℃; for 0.5h;

malononitrile; With sodium acetate; In water; at 0 ℃; for 2h;

DOI:10.1039/c4ob01951b

Reference yield: 96.0%

4-nitrobenzenediazonium tetrafluoroborate (456-27-9) + malononitrile (109-77-3) → 4-nitrophenylhydrazonopropanedinitrile (3722-12-1)

Guidance literature:

With sodium acetate; silica gel; In neat (no solvent); at 20 ℃; for 0.5h; Milling;

DOI:10.2174/1570178611999140404111411

Reference yield: 95.0%

(p-nitrophenyl)azo-tert-cumylmalonitrile (101225-70-1) → 4-nitrophenylhydrazonopropanedinitrile (3722-12-1) + isopropenylbenzene (98-83-9,6144-04-3,25014-31-7,42612-14-6)

Guidance literature:

In dimethyl sulfoxide; at 60 ℃; Rate constant; decomposition, other solvent, other temperature;

DOI:10.1021/ja00269a042

upstream raw materials:

methanol

(p-nitrophenyl)azo-tert-cumylmalonitrile

(2-(4-nitrophenylhydrazono)-3-iminopropanedinitrile)-S-thioacetic acid

5-(4-Nitro-phenylazo)-cyclopenta-1,3-diene-1,2,3,4,5-pentacarboxylic acid pentamethyl ester

Downstream raw materials:

2-(p-nitrophenylhydrazono)-2-cyan-N,N-(3-oxopentamethylen)-acetamidin

N-methyl-hydrazone

4-nitrophenylhydrazono-1H-tetrazol-5-yl-acetonitrile

Refernces

• 1、 Demir?al?, Aykut. "Novel heterocyclic disazo dyes containing pyrazole and phenylpyrazole. part 1: Synthesis, characterization, solvent polarity and acid-base sensitive characteristics". . . Retrieved 2021/02/02.
• 2、 Alvarez, Karine,Busca, Patricia,Calvez, Vincent,Delelis, Olivier,Fichez, Jeanne,Gizzi, Patrick,Gravier-Pelletier, Christine,Le Corre, Laurent,Prestat, Guillaume,Sayon, Sophie,Soulie, Cathia,Marcelin, Anne-Geneviève,Priet, Stéphane. "Discovery, SAR study and ADME properties of methyl 4-amino-3-cyano-1-(2-benzyloxyphenyl)-1H-pyrazole-5-carboxylate as an HIV-1 replication inhibitor". . p. 577 - 582. Retrieved 2020/06/04.