Basic information
- CAS
602-38-0- Standard SMILES
O=[N+]([O-])c1cccc2cccc([N+](=O)[O-])c12- InChIKey
AVCSMMMOCOTIHF-UHFFFAOYSA-N- Molecular formula
- C10H6N2O4
- Average molar mass
- 218.17 g/mol
- Monoisotopic mass
- 218.03275667
Overview
1,8-dinitronaphthalene appears as yellow crystals. (NTP, 1992)
Names & identifiers
- Preferred name
- 1,8-Dinitronaphthalene
- IUPAC
- 1,8-dinitronaphthalene
- English name
- 1,8-Dinitronaphthalene
- Molecular formula
- C10H6N2O4
- Molecular weight
- 218.17
Names & synonyms
1,8-DINITRONAPHTHALENE602-38-0Naphthalene, 1,8-dinitro-DTXSID9025166H6D9Q0K9E6NSC-6323J3.306ECCRIS-2840DTXCID905166CHEBI:50642RefChem:737621,8-diNN
Show more names
1,8-Dinitronaphthale1,8-Dinitrophthalene1,8-DinitronapthaleneLABOTEST-BB LT004369381,8-Dinitronaphthalene,85%1,8-Dinitronaphthalene, NSC 63231,8-Dinitronaphthalene,97%,contains variableamounts of water
210-016-11,8-dinitro-naphthalenMFCD000039181,8-Dinitronaphthalene (>85%)CCRIS 2840NSC 6323EINECS 210-016-1BRN 1881846
Database identifiers
- CAS
602-38-0- PubChem CID
- 11764
- DTXSID
DTXSID9025166- ChEMBL
CHEMBL167529- ChEBI
CHEBI:50642- UNII
- H6D9Q0K9E6
- EC Number
- 210-016-1
- Nikkaji
- J3.306E
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 91.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 268
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Nitros, Aromatic
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP2.52
Solubilityless than 1 mg/mL at 66 °F (NTP, 1992)
Melting Point340 to 342 °F (NTP, 1992)
Vapor Density7.51 (NTP, 1992) - Heavier than air; will sink (Relative to Air)
Vapor Pressure0.00000428 [mmHg]
Physical Description
1,8-dinitronaphthalene appears as yellow crystals. (NTP, 1992)
Yellow solid; [CAMEO] Yellow crystalline powder; [MSDSonline]
Physicochemical properties
- Melting point
- 161 °C · 161 °C
- Boiling point
- 358.84 °C · 358.84°C (rough estimate)
- Density
- 1.433 · 1.4330 (rough estimate)
- refractive index
- 1.704 · 1.7040 (estimate)
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Pale Yellow to Light Yellow
- Water Solubility
- 34 mg/L · 34mg/L(15 ºC)
- Henry's Law Constant
- 5.2 · 5.2×103 mol/(m3Pa) at 25℃, Parnis et al. (2015)
- Stability
- Stability Shock and heat sensitive - may react violently if heated or ground. Combustible. Incompatible with strong oxidizing agents.
- InChI
- 1S/C10H6N2O4/c13-11(14)8-5-1-3-7-4-2-6-9(10(7)8)12(15)16/h1-6H
- InChIKey
- AVCSMMMOCOTIHF-UHFFFAOYSA-N
- SMILES
- [O-][N+](=O)c1cccc2cccc([N+]([O-])=O)c12
- CAS DataBase Reference
- 602 · 602-38-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 6 D9Q0K9E6 · H6D9Q0K9E6
- NIST Chemistry Reference
- 1 · Naphthalene, 1,8-dinitro-(602-38-0)
- EPA Substance Registry System
- 1 · 1,8-Dinitronaphthalene (602-38-0)
- UNSPSC Code
- 12352103 · 12352103
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Warning
- Hazard statements
- 228 · H228-H315-H319-H335
- Precautionary statements
- 210 · P210-P240-P241-P261-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36/37/38
- Safety Statements
- 16 · 16-26-36
- RIDADR
- 2811 · 2811
- WGK Germany
- 3 · 3
- RTECS
- 4552000 · QJ4552000
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- Storage Class
- 4.1 B · 4.1B - Flammable solid hazardous materials
- Hazard Classifications
- 2 Flam · Eye Irrit. 2Flam. Sol. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Danger
H228 (97.5%): Flammable solid [Danger Flammable solids]
P210, P240, P241, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Not Classified
Hazard information
Regulatory InformationNaphthalene, 1,8-dinitro-: Does not have an individual approval but may be used under an appropriate group standard
Fire HazardsFlash point data for this chemical is not available, however it is probably combustible. (NTP, 1992)
Health Hazards
SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes; skin pigmentation, headache, dizziness, cyanosis, nausea, vomiting, anemia, insomnia, fatigue, weight loss, central nervous system depression, liver damage, toxic hepatitis, and kidney damage.
Hazards Summary
Potentially explosive; [Ullmann] Explosive; A strong oxidizing agent; A skin, eye, and mucous membrane irritant; Symptoms of exposure to this compound may include skin pigmentation, headache, dizziness, cyanosis, nausea, vomiting, anemia, insomnia, fatigue, weight loss, central nervous system depression, liver damage, toxic hepatitis, and kidney damage. [CAMEO] An irritant; May induce methemoglobinemia; [MSDSonline] See 2-Nitronaphthalene.
Reactive GroupNitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Reactivity AlertsExplosive
Reactivity Profile1,8-DINITRONAPHTHALENE is sensitive to heat and shock. (NTP, 1992)
Air and Water ReactionsInsoluble in water.
Hazard Classes and CategoriesFlam. Sol. 2 (97.5%)
Safety & protection
Fire FightingFires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: You should dampen the solid spill material with acetone, then transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the adsorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.
Personal Protective Equipment (PPE)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)
Toxicology
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Safety data
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- QJ4552000
- ridadr
- 2811
- risk_code
- 11-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 16-26-36
- hazard_class
- 6.1(b)
- Storage Class
- 4.1B - Flammable solid hazardous materials
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H228-H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Flam. Sol. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P210-P240-P241-P261-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesUsed as a intermediate in the production of naphthperinones; [Ullmann]
General Manufacturing InformationNaphthalene, 1,8-dinitro-: INACTIVE
Applications
Uses1,8-Dinitronaphthalene (cas# 602-38-0) is a compound useful in organic synthesis.
General Description1,8-dinitronaphthalene appears as yellow crystals. (NTP, 1992)
Preparation methods
PreparationSeparation of dinitronaphthalene: Crude mixtures of dinitronaphthalene (5 g, from Table-3 run 8) was placed together with 50 mL acetone in a 100 mL flask, stirred and heated to reflux. The suspension was refluxing for 2 h and then cooled to 30 oC by stirred and filtered quickly. The precipitate was recrystallized by acetone and 1,5-dinitronaphthalene as light yellow crystals (1.725 g) was got. Then the filter liquor was concentrated to one-thirds of original volume, filtered, the precipitate was recrystallized by toluene and 1,8- dinitronaphthalene as light yellow crystals (1.987 g) was got. 1, 5-Dinitronaphthalene: m.p. 215-216 oC, 1H NMR (400 MHz, CDCl3): δ = 7.84 (t, 2H), 8.33 (d, 2H), 8.81 (d, 2H). 1, 8-Dinitronaphthalene: m.p. 172-173 oC, 1H NMR (400 MHz, CDCl3): δ = 7.98 (t, 2H), 8.51 (dd, 4H). Zeolite-Assisted Regioselective Synthesis of Dinitronaphthalene
Upstream & downstream products
Downstream products
Additional notes
DefinitionChEBI: 1,8-dinitronaphthalene is a dinitronaphthalene carrying nitro groups at positions 1 and 8.
Related reactions
2 records
Compound notes
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