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Nitrosobenzene information


Nitrosobenzene
Skeletal formula
Ball-and-stick model
Names
Preferred IUPAC name
Nitrosobenzene
Identifiers
CAS Number
  • 586-96-9 checkY
3D model (JSmol)
  • monomer: Interactive image
  • dimer: Interactive image
ChEBI
  • CHEBI:27986 checkY
ChEMBL
  • ChEMBL98797 checkY
ChemSpider
  • 10989 checkY
ECHA InfoCard 100.008.721 Edit this at Wikidata
KEGG
  • C06876 checkY
PubChem CID
  • 11473
RTECS number
  • DA6497525
UNII
  • ZI9W9E8G2Z checkY
CompTox Dashboard (EPA)
  • DTXSID7060417 Edit this at Wikidata
InChI
  • InChI=1S/C6H5NO/c8-7-6-4-2-1-3-5-6/h1-5H checkY
    Key: NLRKCXQQSUWLCH-UHFFFAOYSA-N checkY
  • InChI=1/C6H5NO/c8-7-6-4-2-1-3-5-6/h1-5H
    Key: NLRKCXQQSUWLCH-UHFFFAOYAR
SMILES
  • monomer: O=Nc1ccccc1
  • dimer: c1ccccc1[N+](=O)N([O-])c1ccccc1
Properties
Chemical formula
C6H5NO
Molar mass 107.112 g·mol−1
Appearance Dark green solid (freshly sublimed monomer); pale yellow solid (dimeric form); bright green solution (light sensitive)
Melting point 65 to 69 °C (149 to 156 °F; 338 to 342 K)
Boiling point 59 °C (138 °F; 332 K) (at 18 mmHg)
Solubility in water
Low
Solubility in other solvents Sol. in organic solvents
Magnetic susceptibility (χ)
-59.1·10−6 cm3/mol
Structure
Molecular shape
N is sp2
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
toxic
GHS labelling:
Pictograms
GHS06: Toxic
Signal word
Danger
Hazard statements
H301, H312, H332
Precautionary statements
P261, P264, P270, P271, P280, P301+P310, P302+P352, P304+P312, P304+P340, P312, P321, P322, P330, P363, P405, P501
Related compounds
Related compounds
Nitrobenzene
Aniline
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Nitrosobenzene is the organic compound with the formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional group, it is a dark green species that exists in equilibrium with its pale yellow dimer. Both monomer and dimer are diamagnetic.

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Nitrosobenzene

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Nitrosobenzene is the organic compound with the formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional...

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Nitrobenzene

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nitrobenzene can be selectively reduced to azoxybenzene, azobenzene, nitrosobenzene, hydrazobenzene, and phenylhydroxylamine. It has been used as a mild...

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Azobenzene dioxide

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colorless. When dissolved, azobenzene dioxide converts to deeply blue nitrosobenzene: (C6H5N(O))2 → 2 C6H5NO Azobenzene dioxide is a weak base, forming coordination...

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Nitroso

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amine, such as R2N–NO Nitrosobenzene Nitric oxide Nitroxyl G. H. Coleman; C. M. McCloskey; F. A. Stuart (1945). "Nitrosobenzene". Org. Synth. 25: 80....

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Phenylhydroxylamine

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rearrangement. Oxidation of phenylhydroxylamine with dichromate gives nitrosobenzene. Like other hydroxylamines it will react with aldehydes to form nitrones...

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Functional group

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  Nitromethane Nitroso compound Nitroso RNO nitroso- (Nitrosyl-)   Nitrosobenzene Oxime Oxime RCH=NOH   Oxime Acetone oxime (2-Propanone oxime) Pyridine...

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Aniline

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amines 1-Naphthylamine 2-Naphthylamine Related compounds Phenylhydrazine Nitrosobenzene Nitrobenzene Supplementary data page Aniline (data page) Except where...

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Metal nitrosyl complex

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Prototypes for such compounds are the organic nitroso compounds, such as nitrosobenzene. A complex with a bent NO ligand is trans-[Co(en)2(NO)Cl]+. The NO−...

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Adolf von Baeyer

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at the age of 81. Antimanic drugs Barbituric acid Hydantoin Indole Nitrosobenzene Phenolphthalein Picoline Resorcinarene "Johann Friedrich Wilhelm Adolf...

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Nitrosation

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compounds containing the R-NO functionality. C-Nitroso compounds, such as nitrosobenzene, are typically prepared by oxidation of hydroxylamines: RNHOH + [O]...

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Transition metal nitroso complexes

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derivatives cause this disorder, which is attributed to their conversion to nitrosobenzene (and derivatives), which inactivate hemoglobin by forming a complex...

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Phenyl azide

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explosive Related compounds Related compounds Aniline Nitrobenzene Nitrosobenzene Phenylhydrazine Phenylhydroxylamine Diazonium cation Except where otherwise...

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Azobenzene

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Flash point 476 °C (889 °F; 749 K) Related compounds Related compounds Nitrosobenzene aniline Except where otherwise noted, data are given for materials in...

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Azoxybenzene

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proposed to proceed via the intermediacy of phenylhydroxylamine and nitrosobenzene: PhNHOH + PhNO → PhN(O)NPh + H2O Another option is the oxidation of...

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C6H5NO

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0371 u) may refer to: 2-Formyl pyridine, or pyridine-2-carboxaldehyde Nitrosobenzene This set index page lists chemical structure articles associated with...

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Diazald

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Diazald Names Preferred IUPAC name N,4-Dimethyl-N-nitrosobenzene-1-sulfonamide Other names N-Methyl-N-nitroso-4-methylbenzenesulfonamide;...

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Azoxy compounds

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nitroso compounds and hydroxylamines, e.g. phenylhydroxylamine and nitrosobenzene (Ph = phenyl, C6H5):: 445  PhNHOH + PhNO ⟶ PhN ( O ) NPh + H 2 O {\displaystyle...

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Petr Zuman

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strongly acidic media, additions of nucleophiles, such as glutathione, to nitrosobenzene, etc. Most of these studies involve biologically important compounds...

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Homochirality

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concerns the proline catalyzed aminoxylation of propionaldehyde by nitrosobenzene. In this system, a small enantiomeric excess of catalyst leads to a...

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Cecily Littleton

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Together they worked on the structure of biomolecules, including nitrosobenzenes. Littleton moved to Philadelphia and worked alongside Arthur Lindo...

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List of compounds with carbon number 12

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azoxybenzene 495-48-7 C12H10N2O phenacyl pyrazine 40061-45-8 C12H10N2O2 nitrosobenzene dimer 35506-28-6 C12H10N3O3P diphenylphosphoryl azide 26386-88-9 C12H10O...

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Glycoazodyes

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detoxification method produces low concentrations of nitrobenzene, aniline, and nitrosobenzene. http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200600686/abstract...

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Zinin reaction

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studies have implicated a role for disulfide that is generated in situ. Nitrosobenzenes (ArNO) and phenylhydroxylamine (ArNHOH) are probable intermediates...

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