1,4-Naphthalenediamine

Base Information

• Chemical Name: 1,4-Naphthalenediamine
• CAS No.: 2243-61-0
• Molecular Formula: C10H10N2
• Molecular Weight: 158.203
• Hs Code.: 2921590090
• European Community (EC) Number: 218-816-2
• UN Number: 3077
• DSSTox Substance ID: DTXSID6025696
• Nikkaji Number: J80.433I
• Wikidata: Q81983926
• ChEMBL ID: CHEMBL3183071
• Mol file: 2243-61-0.mol

Synonyms:1,4-naphthylenediamine

Chemical Property of 1,4-Naphthalenediamine

Chemical Property:

• Vapor Pressure: 1.17E-05mmHg at 25°C
• Melting Point: 114-116 °C
• Refractive Index: 1.757
• Boiling Point: 369.6 °C at 760 mmHg
• PKA: 5.72±0.10(Predicted)
• Flash Point: 211.5 °C
• PSA: 52.04000
• Density: 1.234 g/cm³
• LogP: 3.16660
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 158.084398327
• Heavy Atom Count: 12
• Complexity: 140
• Transport DOT Label: Class 9

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=CC=C2N)N

Technology Process of 1,4-Naphthalenediamine

There total 33 articles about 1,4-Naphthalenediamine 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%

1-amino-4-nitronaphthalene (776-34-1) → 1,4-diaminonaphthalene (2243-61-0)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/acs.jmedchem.0c02094

Reference yield: 83.0%

α-naphthyl red hydrochloride (83833-14-1) → 1,4-diaminonaphthalene (2243-61-0)

Guidance literature:

With hydrogenchloride; zinc; In methanol;

DOI:10.1021/jm060566j

Reference yield: 56.0%

1,4-dibromonaphthalene (83-53-4) → 1,4-diaminonaphthalene (2243-61-0)

Guidance literature:

With dichlorobis(tri-O-tolylphosphine)palladium; nicotinamide; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; at 150 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.033

upstream raw materials:

4-(4-amino-naphthalen-1-ylazo)-benzenesulfonic acid

1-amino-4-nitronaphthalene

4-o-tolylazo-[1]naphthylamine

4-phenylazo-1-naphthylamine

Downstream raw materials:

[1,4]naphthoquinone

diethyl 2,2′-(naphthalene-1,4-diylbis(((4-methoxyphenyl)sulfonyl)azanediyl))diacetate

2,2′-(naphthalene-1,4-diylbis(((4-methoxyphenyl)sulfonyl)azanediyl))diacetic acid

N,N′-(naphthalene-1,4-diyl)bis(4-methylbenzenesulfonamide)

Refernces

• 1、 Lu, Meng-Chen,Tan, Shi-Jie,Ji, Jian-Ai,Chen, Zhi-Yun,Yuan, Zhen-Wei,You, Qi-Dong,Jiang, Zheng-Yu. "Polar Recognition Group Study of Keap1-Nrf2 Protein-Protein Interaction Inhibitors". . p. 835 - 840. Retrieved 2016.
• 2、 Yasuda, Daisuke,Nakajima, Mao,Yuasa, Akihiro,Obata, Rika,Takahashi, Kyoko,Ohe, Tomoyuki,Ichimura, Yoshinobu,Komatsu, Masaaki,Yamamoto, Masayuki,Imamura, Riyo,Kojima, Hirotatsu,Okabe, Takayoshi,Nagano, Tetsuo,Mashino, Tadahiko. "Synthesis of Keap1-phosphorylated p62 and Keap1-Nrf2 protein-protein interaction inhibitors and their inhibitory activity". . p. 5956 - 5959. Retrieved 2016.
• 3、 Abed, Dhulfiqar Ali,Lee, Sumi,Wen, Xia,Ali, Ahmed R.,Mangipudy, Vaibhav,Aleksunes, Lauren M.,Hu, Longqin. "Optimization of 1,4-bis(arylsulfonamido)naphthalene-N,N'-diacetic acids as inhibitors of Keap1-Nrf2 protein-protein interaction to suppress neuroinflammation". supporting information. . Retrieved 2021/07/19.
• 4、 -. "SMALL MOLECULE DIRECT INHIBITORS OF KEAP1-NRF2 PROTEIN-PROTEIN INTERACTION". Paragraph 0206-0207; 0210-0211. . Retrieved 2020/07/31.