2-Nitrodiphenylamine

Base Information

• Chemical Name: 2-Nitrodiphenylamine
• CAS No.: 119-75-5
• Molecular Formula: C12H10N2O2
• Molecular Weight: 214.224
• Hs Code.: 29214400
• European Community (EC) Number: 204-348-6
• NSC Number: 629274,105613,4754
• UN Number: 1661
• UNII: DT9NA7ZDD8
• DSSTox Substance ID: DTXSID4025749
• Nikkaji Number: J37.804F
• Wikipedia: 2-Nitrodiphenylamine
• Wikidata: Q209448
• Metabolomics Workbench ID: 143642
• ChEMBL ID: CHEMBL1450018
• Mol file: 119-75-5.mol

Synonyms:2-Nitrodiphenylamine;119-75-5;2-Nitro-N-phenylaniline;o-Nitrodiphenylamine;Sudan Yellow 1339;Benzenamine, 2-nitro-N-phenyl-;N-Phenyl-o-nitroaniline;o-Nitro-N-phenylaniline;Diphenylamine, 2-nitro-;Nitrodiphenylamine;(2-nitrophenyl)phenylamine;C.I. 10335;NSC 105613;CCRIS 6075;Nitrodiphenylamine, 2-;EINECS 204-348-6;DT9NA7ZDD8;o-(Phenylamino)nitrobenzene;N-Phenyl-2-nitrobenzenamine;AI3-08882;DTXSID4025749;(2-NITRO-PHENYL)-ANILINE;NSC-4754;NSC629274;NSC-105613;NSC-629274;CI 10335;SMR000348018;2-nitro-N-phenyl-aniline;2-Nitro-phenyl)-phenyl-amine;NSC4754;ST044502;UNII-DT9NA7ZDD8;2-Nitrodiphenylamine, 98%;Color Index No. 10335;Color Index Number 10335;Colour Index No. 10335;MLS001004443;MLS002152876;Colour Index Number 10335;SCHEMBL230292;(2-nitro-phenyl)-phenyl-amine;DTXCID705749;2-(N-phenylamino) nitrobenzene;N-PHENYL-2-NITROANILINE;CHEMBL1450018;SCHEMBL11121128;N-(2-NITROPHENYL)ANILINE;N-(2-Nitrophenyl)-N-phenylamine;HMS2702H15;Tox21_200720;LS-621;MFCD00007089;N-(2-Nitrophenyl)-N-phenylamine #;NSC105613;(2-Anilinophenyl)(hydroxy)azane oxide;AKOS001044887;AKOS015965866;AM86377;CS-W014937;NCGC00091169-01;NCGC00091169-02;NCGC00258274-01;AC-20804;CAS-119-75-5;DS-13298;EU-0000259;FT-0613194;N0196;Q209448;SR-01000390730;Q-200312;SR-01000390730-1

Chemical Property of 2-Nitrodiphenylamine

Chemical Property:

• Appearance/Colour: red crystalline solid
• Vapor Pressure: 4.83E-06mmHg at 25°C
• Melting Point: 74-76 °C(lit.)
• Refractive Index: 1.65
• Boiling Point: 353.7 °C at 760 mmHg
• PKA: -3.39±0.20(Predicted)
• Flash Point: 167.7 °C
• PSA: 57.85000
• Density: 1.36 g/cm³
• LogP: 3.93460
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility.: Chloroform (Slightly), , DMSO (Slightly), Methanol (Slightly, Sonicated)
• Water Solubility.: negligible
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 214.074227566
• Heavy Atom Count: 16
• Complexity: 234
• Transport DOT Label: Poison

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

(2-Nitrophenyl)phenylamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitroanilines
• Canonical SMILES: C1=CC=C(C=C1)NC2=CC=CC=C2[N+](=O)[O-]
• Description: 2-Nitrodiphenylamine is a double-base (DB) rocket propellant stabilizer and its microencapsulation potentially improves the shelf life of DB rocket propellants.
• Uses: (2-Nitrophenyl)phenylamine (cas# 119-75-5) is a compound useful in organic synthesis. 2-Nitrodiphenylamine is used to control the combustion of propylene glycol dinitrate in Otto fuel II (US navy propellant for torpedoes and other weapons systems); Also used as a solvent dye; Used as stabilizer for nitroglycerin and as a chemical intermediate

Technology Process of 2-Nitrodiphenylamine

There total 48 articles about 2-Nitrodiphenylamine 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: 99.0%

aniline (62-53-3) + 2-nitrophenyl nonaflate (342589-38-2) → 2-nitro-N-phenylaniline (119-75-5)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; 1-methyl-2,3,4,6,7,8-hexahydro-1H-pyrimido[1,2-a]pyrimidine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In toluene; at 115 ℃; for 0.75h; microwave irradiation;

DOI:10.1021/jo052131u

Reference yield: 98.0%

2-nitrophenyl bromide (577-19-5) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In toluene; at 110 ℃;

DOI:10.1016/j.tetlet.2007.09.045

Reference yield: 98.0%

2-nitrophenylboronic acid (5570-19-4) + aniline (62-53-3) → 2-nitro-N-phenylaniline (119-75-5)

Guidance literature:

With potassium fluoride; In dimethyl sulfoxide; at 130 ℃; for 2h; Inert atmosphere;

DOI:10.1007/s11164-019-03760-0

upstream raw materials:

bromobenzene

o-nitroacetanilide

N-nitroso(2-nitrophenyl)phenylamine

2-nitrodiphenylamine-4-sulfonic acid

Downstream raw materials:

2-nitro-N-methyl-N-phenylaniline

N-carbethoxy acetyl 2-nitro diphenylamine

2-(dimethylamino)-N-methyl-diphenylamine

N-(2-nitrophenyl)-N-(2-methylprop-2-enyl)aniline

Refernces

• 1、 Zhang, Tengfei,Zhang, Ran,Zhao, Yun,Ni, Zhonghai. "A new series of N-substituted tetraphenylethene-based benzimidazoles: Aggregation-induced emission, fast-reversible mechanochromism and blue electroluminescence". . p. 276 - 285. Retrieved 2018.
• 2、 Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen. "Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2- phosphonate as the new ligand". . p. 8107 - 8109. Retrieved 2005.
• 3、 Zhang, Zhaohang,Jiang, Wei,Ban, Xinxin,Yang, Min,Ye, Shanghui,Huang, Bin,Sun, Yueming. "Solution-processed efficient deep-blue fluorescent organic light-emitting diodes based on novel 9,10-diphenyl-anthracene derivatives". . p. 29708 - 29717. Retrieved 2015.
• 4、 Liu, Xu-Guang,Sun, Wenfang. "Synthesis, photophysics, and reverse saturable absorption of bipyridyl platinum(II) bis(acetylide) complexes bearing aromatic electron-withdrawing substituents on the acetylide ligands". . p. 10318 - 10325. Retrieved 2014.
• 5、 Perin,Hok,Be?,Persoons,Vanstreels,Daelemans,Vianello,Hranjec. "N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis". . . Retrieved 2021.
• 6、 Shi, Ji-cheng,Zhang, Lixue,Zhou, Fabin. "A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines". . p. 238 - 243. Retrieved 2021/09/07.
• 7、 Absalan, Yahya,Ghandi, Khashayar,Gholizadeh, Mostafa,Kovalchukova, Olga,Mahmoudi, Ghodrat,Sarvestani, Hossein Sabet,Shad, Nazanin Noroozi,Strashnov, Pavel. "Schiff bases-titanium (III) & (IV) complex compounds: Novel photocatalysts in Buchwald-Hartwig C–N cross-coupling reaction". . . Retrieved 2021/05/21.