1,8-Dinitronaphthalene

Base Information

• Chemical Name: 1,8-Dinitronaphthalene
• CAS No.: 602-38-0
• Molecular Formula: C10H6 N2 O4
• Molecular Weight: 218.169
• Hs Code.: 2904.20
• European Community (EC) Number: 210-016-1
• NSC Number: 6323
• UNII: H6D9Q0K9E6
• DSSTox Substance ID: DTXSID9025166
• Nikkaji Number: J3.306E
• Wikidata: Q27122164
• ChEMBL ID: CHEMBL167529
• Mol file: 602-38-0.mol

Synonyms:1,8-Dinitronaphthalene;NSC 6323

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Chemical Property of 1,8-Dinitronaphthalene

Chemical Property:

• Appearance/Colour: Yellow Crystalline Powder
• Vapor Pressure: 6.22E-06mmHg at 25°C
• Melting Point: 171 - 172 C (97 %)
• Refractive Index: 1.7040 (estimate)
• Boiling Point: 389.8°C at 760 mmHg
• Flash Point: 200.3°C
• PSA: 91.64000
• Density: 1.481g/cm³
• LogP: 3.70260
• Water Solubility.: 34mg/L(15 oC)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 218.03275668
• Heavy Atom Count: 16
• Complexity: 268

Purity/Quality:

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC2=C(C(=C1)[N+](=O)[O-])C(=CC=C2)[N+](=O)[O-]
• General Description: 1,8-Dinitronaphthalene (also known as NSC 6323) is a dinitrated derivative of naphthalene, typically formed through regioselective nitration processes. It is one of the isomers produced alongside 1,5-dinitronaphthalene in catalytic nitration reactions, such as those involving HZSM-5-supported phosphotungstic acid, where it can achieve yields of up to 49.2%. Additionally, it can be synthesized photochemically via reactions between excited 1-nitronaphthalene and NO₂, particularly under acidic conditions (optimal around pH 3.5). Alternative methods, such as nitration of 1-nitronaphthalene using NO₂ with Ni(CH₃COO)₂·4H₂O as a catalyst, also yield 1,8-dinitronaphthalene, though with lower selectivity (3.56%) compared to other isomers. These methods highlight its formation under varying conditions, including catalytic, photochemical, and mild nitration pathways.

Technology Process of 1,8-Dinitronaphthalene

There total 29 articles about 1,8-Dinitronaphthalene 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: 81.0%

Naphthalene-1,8-dicarboxylic acid (518-05-8) → 1,8-dinitronaphthalene (602-38-0)

Guidance literature:

With nitronium tetrafluoborate; silver carbonate; In N,N-dimethyl acetamide; at 90 ℃; for 12h; regioselective reaction; Inert atmosphere; Schlenk technique;

DOI:10.1021/acs.joc.5b02133

Reference yield: 78.5%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 1-Nitronaphthalene (86-57-7) + 1,8-dinitronaphthalene (602-38-0) + 1,5-dinitronaphthalene (605-71-0)

Guidance literature:

With nitric acid; at 64.84 ℃; for 3h; Reagent/catalyst; Catalytic behavior;

DOI:10.1007/s11164-014-1549-1

Reference yield: 49.2%

naphthalene (91-20-3,71998-51-1,72931-45-4) → 1,8-dinitronaphthalene (602-38-0) + 1,5-dinitronaphthalene (605-71-0)

Guidance literature:

With nitric acid; at 64.84 ℃; for 3h; Reagent/catalyst; Catalytic behavior;

DOI:10.1007/s11164-014-1549-1

upstream raw materials:

naphthalene

1-Nitronaphthalene

1-amino-4,5-dinitronaphthalene

4,5-dinitro-[1]naphthoic acid

Downstream raw materials:

1,8-dinitro-[2]naphthol

4,5-dinitro-[1]naphthol

1-benzyloxy-4,5-dinitronaphthalin

1,8-dichloronaphthalene