Basic information
- CAS
2508-20-5- Standard SMILES
O=Nc1ccc2c(c1)Cc1ccccc1-2- InChIKey
XZWGJDANCSXBDW-UHFFFAOYSA-N- Molecular formula
- C13H9NO
- Average molar mass
- 195.22 g/mol
- Monoisotopic mass
- 195.06841391
Names & identifiers
- Preferred name
- 2-Nitroso-9H-fluorene
- IUPAC
- 2-nitroso-9H-fluorene
- English name
- 2-nitrosofluorene
- Molecular formula
- C13H9NO
- Molecular weight
- 195.22
Names & synonyms
2-NITROSOFLUORENE2-nitroso-9H-fluoreneNitrosofluorene2508-20-5Fluorene, 2-nitroso-34E9V9B29KRefChem:4772409H-Fluorene, 2-nitroso-CCRIS 1212HSDB 2112BRN 1910954UNII-34E9V9B29K
Show more names
DTXSID2075211NITROSOFLUORENE, 2-SCHEMBL62414652-NITROSOFLUORENE [HSDB]AKOS006273447Q27256359
Database identifiers
- CAS
2508-20-5- PubChem CID
- 17271
- DTXSID
DTXSID2075211- UNII
- 34E9V9B29K
- Nikkaji
- J892C
Properties
Computed structural properties
- XLogP
- 3.2
- Topological polar surface area
- 29.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 253
Experimental & physicochemical properties
PolymersOther Classes -> Polycyclic Aromatic Hydrocarbons
DecompositionWhen heated to decomp it emits oxides of nitrogen.
Physicochemical properties
- Melting point
- 76 · 76-77 °C
- Boiling point
- 331.88 °C · 331.88°C (rough estimate)
- Density
- 1.1266 · 1.1266 (rough estimate)
- refractive index
- 1.606 · 1.6060 (estimate)
- FDA UNII
- 34 E9V9B29K · 34E9V9B29K
- EPA Substance Registry System
- 9 H-Fluorene, · 9H-Fluorene, 2-nitroso- (2508-20-5)
- Hazardous Substances Data
- 2508 · 2508-20-5(Hazardous Substances Data)
- Toxicity
- 50 ng/plate · mmo-sat 50 ng/plate CBINA8 54,71,85
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Hazards SummaryEvidence of mutagenicity; [HSDB] See POLYCYCLIC AROMATIC HYDROCARBONS.
Toxic Combustion ProductsWhen heated to decomp it emits oxides of nitrogen.
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Non-Human Toxicity Excerpts
[MUTATION RESEARCH 87: 211 (1981)] DNA REPAIR DEFICIENT BACTERIAL TESTS: POSITIVE.
... NITROSOFLUORENE ... IS A POWERFUL FRAME SHIFT MUTAGEN IN SALMONELLA TYPHIMURIUM. THERE IS ... THOUGHT TO BE A CORRELATION BETWEEN CMPD THAT ARE MUTAGENIC FOR BACTERIA & THOSE WHICH ARE DIRECTLY CARCINOGENIC FOR ANIMALS. ... 2-NITROSOFLUORENE IS ONLY WEAKLY CARCINOGENIC. ITS MUTAGENICITY COULD BE CAUSED BY ABILITY OF BACTERIA TO REDUCE THE CMPD TO N-HYDROXY FLUORENAMINE ... THE INCREASED MUTAGENIC ACTIVITY OF THE NITROSO CMPD OVER THE N-HYDROXY DERIVATIVE MAY BE CAUSED BY INCR LIPID SOLUBILITY.
2-NITROSOFLUORENE SC INJECTED INTO RATS SHOWED LOCAL & EAR DUCT TUMORS. /FROM TABLE/
THE GROWTH TEMPERATURE OF SALMONELLA TYPHIMURIUM INFLUENCES THE EXTENT OF BINDING OF 2-NITROSOFLUORENE (NOF) TO THIS BACTERIUM AS WELL AS THE MUTAGENICITY OF THIS CARCINOGEN. (14)C-LABELED NOF UPTAKE IN BACTERIA GROWN AT DIFFERENT TEMPERATURES SHOWED GOOD CORRELATION WITH MUTAGENICITY DATA. THE AMOUNT OF NITROXYL FREE RADICAL ADDUCT FORMED DID NOT CORRELATE WITH UNSATURATED FATTY-ACID CONTENT.
Safety data
Chemistry & industry
Pharmacology
Mechanism of Action
2-NITROSOFLUORENE INDUCES FRAMESHIFT MUTATION & BASE-PAIR SUBSTITUTIONS IN SALMONELLA TYPHIMURIUM STRAINS TA98, TA100, TA1537 & TA1538. A COMPARISON OF THE MUTAGENIC POTENCY OF SEVERAL DERIVATIVES OF FLUORENE FOR SEVERAL STRAINS OF SALMONELLA TYPHIMURIUM SUGGEST THE IMPORTANCE OF A CARBONYL GROUP SUBSTITUTED AT THE CARBON-9 POSITION OF THE MUTAGENIC DERIVATIVE WITH RESPECT TO MUTAGENIC POTENCY. A FEASIBLE MECHANISM FOR THE INTERACTION OF MUTAGENIC FLUORENE DERIVATIVE WITH DNA IS PRESENTED. THIS MECHANISM REQUIRES THE INTERACTION OF THE MUTAGENIC MOLECULE WITH CARBON-8 OF QUANINE & A 2ND CONCURRENT INTERACTION WITH THE CARBON-4 AMINO GROUP OF AN ADJACENT CYTOSINE RESIDUE.
Metabolism/Metabolites
N-HYDROXY DERIVATIVES /OF AROMATIC AMINES/ CAN BE FORMED BY REDUCTION. WITHIN TISSUES ... ARE ... REDUCTASES ... WHICH REDUCE ... NITROSO ... GROUPS TO N-HYDROXY DERIVATIVES. ... 2-NITROSOFLUORENE, AN OXIDN PRODUCT OF N-HYDROXY-2-FLUORENAMINE, CAN BE CONVERTED BACK TO PARENT CMPD ENZYMATICALLY. HAMSTER & RABBIT LIVER SOL ENZYMES HAD CONSIDERABLY MORE ACTIVITY IN CARRYING OUT THIS REDUCTION THAN THOSE FROM THE RAT.
STUDIES OF NONENZYMIC REACTIONS OF TRANS-4-NITROSOSTILBENE, 4-NITROSOBIBENZYL, 2-NITROSOFLUORENE & P-NITROSOTOLUENE WITH GLUTATHIONE REVEALED THE CORRESPONDING HYDROXYLAMINE, AMINE & WATER-SOL ADDUCT, WHICH HYDROLYZED UNDER ACIDIC OR ALKALINE CONDITIONS TO AMINE & GLUTATHIONE SULFINIC ACID. REDUCTION TO THE AMINE IS EXPLAINED BY FORMATION OF ADDUCTS WHICH ARE REDUCED BY GLUTATHIONE WITH THE PRODUCTION OF OXIDIZED GLUTATHIONE.
THE CARCINOGEN 2-NITROSOFLUORENE REACTED WITH LIPID MOLECULES CONTAINING CARBON-CARBON DOUBLE BONDS TO YIELD FREE RADICALS (NITROXYL FREE RADICAL OF 2-NITROSOFLUORENE COVALENTLY BOUND TO THE LIPID).
MeSH Pharmacological ClassificationSubstances that increase the risk of NEOPLASMS in humans or animals. Both genotoxic chemicals, which affect DNA directly, and nongenotoxic chemicals, which induce neoplasms by other mechanism, are included.
Uses & manufacturing
U.S. Production
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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