2-Nitronaphthalene

Base Information

• Chemical Name: 2-Nitronaphthalene
• CAS No.: 581-89-5
• Molecular Formula: C10H7 N O2
• Molecular Weight: 173.171
• Hs Code.: 2904209090
• European Community (EC) Number: 209-474-5
• ICSC Number: 1504
• UN Number: 2538
• UNII: V5NB52B64Q
• DSSTox Substance ID: DTXSID2073198
• Nikkaji Number: J47.056B
• Wikipedia: 2-Nitronaphthalene
• Wikidata: Q2617910
• Metabolomics Workbench ID: 57481
• ChEMBL ID: CHEMBL353064
• Mol file: 581-89-5.mol

Synonyms:2-nitronaphthalene

Chemical Property of 2-Nitronaphthalene

Chemical Property:

• Appearance/Colour: yellow to brown solid.
• Vapor Pressure: 0.000628mmHg at 25°C
• Melting Point: 65-73 °C
• Refractive Index: 1.5200 (estimate)
• Boiling Point: 319.6 ºC at 760 mmHg
• Flash Point: 158.7 ºC
• PSA: 45.82000
• Density: 1.279 g/cm³
• LogP: 3.27120
• Storage Temp.: 2-8°C
• XLogP3: 3.3
• 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

2-Nitronaphthalene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): TN
• Hazard Codes: T:Toxic;;
• Statements: R45:May cause cancer.; R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
• Safety Statements: S45:In case of accident of if you feel unwell, seek medical advice immediately (show the label where possible).; S53:Avoi

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC=C2C=C(C=CC2=C1)[N+](=O)[O-]
• Inhalation Risk: Evaporation at 20 °C is negligible; a harmful concentration of airborne particles can, however, be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Medical observation is indicated. The effects may be delayed.

Technology Process of 2-Nitronaphthalene

There total 62 articles about 2-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%

2-naphthyl triflate (3857-83-8) → 2-nitronaphthalene (581-89-5)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; t-BuBrettPhos; tris(3,5-dioxaheptyl)amine; sodium nitrite; In tert-butyl alcohol; at 130 ℃; Schlenk technique; Inert atmosphere;

DOI:10.1002/anie.201304039

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: 88.0%

naphthalene-2-boronic acid (32316-92-0) → 2-nitronaphthalene (581-89-5)

Guidance literature:

With copper(I) oxide; tetrabutylammonium nitrite; In acetonitrile; at 20 ℃;

DOI:10.2174/157017812800221717

upstream raw materials:

naphthalene

nitromethane

2-methylisoquinolinium iodide

6-nitrotetralin

Downstream raw materials:

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

phthalic anhydride

4-nitrophthalic anhydride

1-bromo-6-nitro-naphthalene

Refernces

• 1、 Ross, David S.,Moran, Kelly D.,Malhotra, Ripudaman. "Catalysis of Nitration of Naphthalene by Lower Oxides of Nitrogen". . p. 2118 - 2120. Retrieved 1983.
• 2、 Shi, Chunjie,Peng, Xinhua,Tai, Yanfang,Dong, Xiongzi,Wang, Haocai. "Zeolite-assisted regioselective mononitration of naphthalene with nitrogen dioxide/molecular oxygen". . p. 3151 - 3156. Retrieved 2013.
• 3、 Fichter,Pluess. "-". . p. 236,243. Retrieved 1932.
• 4、 Fierz-David,Sponagel. "-". . p. 98,105. Retrieved 1943.
• 5、 Capperucci, Antonella,Dalia, Camilla,Tanini, Damiano. "The polyhedral nature of selenium-catalysed reactions: Se(iv) species instead of Se(vi) species make the difference in the on water selenium-mediated oxidation of arylamines". supporting information. p. 5680 - 5686. Retrieved 2021/08/16.
• 6、 Budinská, Alena,Katayev, Dmitry,Passera, Alessandro,Zhang, Kun. "N-Nitroheterocycles: Bench-Stable Organic Reagents for Catalytic Ipso-Nitration of Aryl- And Heteroarylboronic Acids". supporting information. . Retrieved 2020/03/30.