1-Nitronaphthalene

Base Information

• Chemical Name: 1-Nitronaphthalene
• CAS No.: 86-57-7
• Molecular Formula: C10H7 N O2
• Molecular Weight: 173.171
• Hs Code.: 29042000
• European Community (EC) Number: 201-684-5
• NSC Number: 9584
• UN Number: 2538
• UNII: A51NP1DL2T
• DSSTox Substance ID: DTXSID7020978
• Nikkaji Number: J3.536J
• Wikipedia: 1-Nitronaphthalene
• Wikidata: Q14848739
• Metabolomics Workbench ID: 54920
• ChEMBL ID: CHEMBL165373
• Mol file: 86-57-7.mol

Synonyms:1-nitronaphthalene

Chemical Property of 1-Nitronaphthalene

Chemical Property:

• Appearance/Colour: yellow to green crystalline powder
• Melting Point: 58 - 60 C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 304 C
• Flash Point: 164 ºC
• PSA: 45.82000
• Density: 1.22
• LogP: 3.27120
• Storage Temp.: 2-8°C
• Solubility.: H2O: insoluble
• Water Solubility.: 0.022 g/L
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 173.047678466
• Heavy Atom Count: 13
• Complexity: 200
• Transport DOT Label: Flammable Solid

Purity/Quality:

98%min ^*data from raw suppliers

1-Nitronaphthalene ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,T,N
• Statements: 11-25-51/53-40-36/37/38-23/24/25
• Safety Statements: 16-45-60-61-28A-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC=C2C(=C1)C=CC=C2[N+](=O)[O-]
• Uses: Usually used to study excited state dynamics of 1-nitropthalene in nonpolar, aprotic and protic solvents. 1-Nitronaphthalene as a nitroaromatic compound is studied for mutagenicity, as nitroaromatics are used in everyday products from polmers, dyes to drugs.

Technology Process of 1-Nitronaphthalene

There total 88 articles about 1-Nitronaphthalene 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: 92.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 1-Nitronaphthalene (86-57-7) + 2-nitronaphthalene (581-89-5)

Guidance literature:

With nitric acid; In acetic anhydride; at 0 ℃; for 1h; Title compound not separated from byproducts;

Reference yield: 20.0%

naphthalene (91-20-3,71998-51-1,72931-45-4) + tetranitromethane (509-14-8) → 1-Nitronaphthalene (86-57-7) + 2-nitronaphthalene (581-89-5) + cis-1,4-dihydro-1-nitro-4-trinitromethylnaphthalene (141738-87-6,144918-65-0,146850-06-8)

Guidance literature:

In dichloromethane; at 20 ℃; for 113h; Yields of byproduct given; Irradiation;

DOI:10.1039/c39920000566

Reference yield:

naphthalene (91-20-3,71998-51-1,72931-45-4) + dinitrogen trioxide (10544-73-7,96607-26-0) → 1-Nitronaphthalene (86-57-7) + 2-nitronaphthalene (581-89-5) + nitrogen(II) oxide (10102-43-9) + cis-nitrous acid (7782-77-6)

Guidance literature:

In sulfolane; Electrochem. Process; anhydrous deoxygenated sulfolane, room temp.; gas chromatography, electroanalysis, Raman spectroscopy;

DOI:10.1016/0013-4686(88)80070-7

upstream raw materials:

naphthalene

ethanol

5-nitro-1,2,3,4-tetrahydronaphthalene

5-nitro-[1]naphthylamine

Downstream raw materials:

1-N-ethylnaphthylamine

1,2-di(naphthalen-1-yl)diazene

N-phenyl-1-naphthylamine

4-ethoxy-[1]naphthylamine

Refernces

INTRAMOLECULAR ELECTRON TRANSFER AND DEHALOGENATION OF NITROAROMATIC ANION RADICALS.

10.1021/ja00341a003

The study investigates the intramolecular electron transfer and dehalogenation processes in a series of nitroaromatic compounds containing halogens (Cl, Br) or tosyl groups at various positions. These compounds undergo one-electron reduction to form anion radicals, which then transfer an electron intramolecularly and release halide or tosylate ions. The rates of dehalogenation are influenced by factors such as the C-X bond dissociation energies, the size and nature of the bridging group, and the relative positions of these groups. The study demonstrates that a-substitution with methyl or chlorine groups increases the rate of dehalogenation by stabilizing the resulting radical and decreasing the C-X bond dissociation energy. Additionally, the study explores the effect of the distance between the halogen and the aromatic ring, as well as the importance of direct electron transfer through space rather than through the aromatic p system. The compounds synthesized and studied include p-nitrobenzyl halides, p-nitrobenzyl tosylate, p-nitrophenylethyl bromide, p-nitrophenylvinyl and -allyl bromides, and nitronaphthalenes with various substituents. The results provide insights into the mechanisms of intramolecular electron transfer and dehalogenation in these systems.