1,5-Naphthalenediamine

Base Information

• Chemical Name: 1,5-Naphthalenediamine
• CAS No.: 2243-62-1
• Molecular Formula: C10H10N2
• Molecular Weight: 158.203
• Hs Code.: 29215990
• European Community (EC) Number: 218-817-8
• ICSC Number: 0668
• NSC Number: 401110
• UN Number: 3077
• UNII: 13PD3J52LK
• DSSTox Substance ID: DTXSID3020916
• Nikkaji Number: J40.472A
• Wikipedia: 1,5-Diaminonaphthalene
• Wikidata: Q2191535
• Metabolomics Workbench ID: 58504
• ChEMBL ID: CHEMBL538965
• Mol file: 2243-62-1.mol

Synonyms:1,5-naphthalenediamine

Chemical Property of 1,5-Naphthalenediamine

Chemical Property:

• Appearance/Colour: Grey to dark brown powder
• Vapor Pressure: 5.09E-06mmHg at 25°C
• Melting Point: 185-187 °C(lit.)
• Refractive Index: 1.757
• Boiling Point: 381.4 °C at 760 mmHg
• PKA: 4.59±0.10(Predicted)
• Flash Point: 220.2 °C
• PSA: 52.04000
• Density: 1.234 g/cm³
• LogP: 3.16660
• Storage Temp.: Store below +30°C.
• Solubility.: 0.04g/l
• Water Solubility.: <0.1 g/100 mL at 20.5℃
• XLogP3: 2.1
• 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:

99% ^*data from raw suppliers

1,5-Diaminonaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: Xn,N
• Statements: 40-50/53
• Safety Statements: 36/37-60-61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Naphthalenes
• Canonical SMILES: C1=CC2=C(C=CC=C2N)C(=C1)N
• Inhalation Risk: No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization.
• Uses: Aromatic amines likely to have high carcinogenic potency. QSARs of aromatic amines. 1,5-naphthalenediamine be used as intermediates for the synthesis of materials. 1,5-Naphthalenediamineis an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuffs. The reducing properties of 1,5-diaminonaphthalene (1,5-DAN) as a MALDI matrix ( matrix-assisted laser desorption ionization) to amino acid sequencing and disulfide bond mapping of human urotensin II possessing one disulfide bond, and human guanylin possessing two disulfide bonds.

Technology Process of 1,5-Naphthalenediamine

There total 38 articles about 1,5-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%

1,4,5-trinitronaphthalene (2243-95-0) → 1,5-naphthalenediamine (2243-62-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 10h;

DOI:10.1023/A:1019615206870

Reference yield: 97.5%

5-nitro-[1]naphthylamine (3272-91-1) → 1,5-naphthalenediamine (2243-62-1)

Guidance literature:

With hydrogen; In palladium; toluene;

Reference yield: 93.6%

5-amino-1-naphthol (83-55-6) → 1,5-naphthalenediamine (2243-62-1)

Guidance literature:

With ammonium hydrogen sulfite; ammonia; In water; at 150 ℃; for 6h;

upstream raw materials:

naphthalene

α-naphthol

1,5-dihydroxynaphthalene

5-nitro-[1]naphthylamine

Downstream raw materials:

N,N'-naphthalene-1,5-diyl-bis-valeramide

N,N'-naphthalene-1,5-diyl-bis-butyramide

N,N'-bis-(2-nitro-benzylidene)-naphthalene-1,5-diyldiamine

5-amino-1-naphthol

Refernces

• 1、 Rodriguez, J. Gonzalo,Tejedor, J. Luis. "Carbon networks based on 1,5-naphthalene units. Synthesis of 1,5-naphthalene nanostructures with extended π-conjugation". . p. 7631 - 7640. Retrieved 2002.
• 2、 Lu,Wei,Zhou,Jiang,Sun,Xia. "Synthesis, structure and catalytic activity of the supported Ni catalysts for highly efficient one-step hydrogenation of 1,5-dinitronaphthalene to 1,5-diaminodecahydronaphthalene". . p. 196 - 206. Retrieved 2015.
• 3、 Dai, Xingchao,He, Dongcheng,Li, Teng,Shi, Feng,Wang, Hongli,Wang, Tao,Wang, Xinzhi. "Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper". . p. 397 - 406. Retrieved 2021/07/21.