Basic information
- CAS
104-91-6- Standard SMILES
O=Nc1ccc(O)cc1- InChIKey
JSTCPNFNKICNNO-UHFFFAOYSA-N- Molecular formula
- C6H5NO2
- Average molar mass
- 123.11 g/mol
- Monoisotopic mass
- 123.0320284
Overview
P-benzoquinone monoxime is a black solid. (NTP, 1992)
Names & identifiers
- Preferred name
- 4-Nitrosophenol
- IUPAC
- 4-nitrosophenol
- English name
- 4-Nitrosophenol
- Molecular formula
- C6H5NO2
- Molecular weight
- 123.11
Names & synonyms
4-NITROSOPHENOL104-91-6p-NitrosophenolPhenol, 4-nitroso-Quinone monoximeNitrosophenolQuinone oximePhenol, p-nitroso-1,4-Benzoquinone monoximepara-NitrosophenolDTXSID002599155EB58H2UP
Show more names
NSC 239647p-quinone monooximeBenzoquinone monoxime1,4-Benzoquinone 4-OxiMep-benzoquinone, monooximeN-Hydroxy-p-benzoquinone imine2,5-Cyclohexadiene-1,4-dione 1-OxiMe4-hydroxyimino-5-cyclohexadien-1-one
NSC-3124DTXCID405991RefChem:526027203-251-64-Benzoquinone Monoxime637-62-7p-Quinone monoximeQuinone monooxime
Database identifiers
- CAS
104-91-6、637-62-7- PubChem CID
- 7729
- DTXSID
DTXSID0025991- ChEMBL
CHEMBL104353、CHEMBL3276923- UNII
- 55EB58H2UP
- EC Number
- 203-251-6
- Nikkaji
- J60.142J、J9.451J
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 49.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 0
- Heavy atoms
- 9
- Formal charge
- 0
- Complexity
- 97.2
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
SpringerMaterials PropertiesCrystal structure
LogP1.29
Color/Form
PALE YELLOW ORTHORHOMBIC NEEDLES, BROWNS @ 126 °C
CRYSTALLIZES IN LIGHT BROWN LEAFLETS
Solubility
less than 1 mg/mL at 70 °F (NTP, 1992)
MODERATELY SOL IN WATER; SOL IN DILUTE ALKALIES GIVING GREEN TO BROWNISH GREEN SOLUTIONS; SOL IN ALC, ETHER, ACETONE
SOL IN HOT BENZENE
Melting Point270 to 291 °F (decomposes) (NTP, 1992)
Vapor Pressure0.15 [mmHg]
Physical Description
P-benzoquinone monoxime is a black solid. (NTP, 1992)
Wet Solid
Pale yellow or light-brown solid; [HSDB] Black solid; [CAMEO] Yellow-brown powder; [MSDSonline]
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302: Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P264+P265, P270, P273, P280, P301+P317, P305+P354+P338, P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)
Danger
H242 (20.7%): Heating may cause a fire [Danger Self-reactive substances and mixtures; Organic peroxides]
P203, P210, P234, P235, P240, P261, P264, P264+P265, P270, P272, P273, P280, P301+P316, P301+P317, P302+P352, P305+P354+P338, P317, P318, P321, P330, P332+P317, P333+P317, P362+P364, P370+P378, P391, P403, P405, P410, P411, P420, and P501 (click each P-code to see the statement)
Hazard information
Regulatory Information
Chemical: Phenol, 4-nitroso-
Phenol, 4-nitroso- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Phenol, 4-nitroso- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)
SP - indicates a substance that is identified in a proposed Significant New Use Rule.
REACH registered substance: 4-nitrosophenol (EC: 203-251-6)
Phenol, 4-nitroso-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - CMR chemicals not registered under REACH: Human health tier II assessment
DOT LabelFlammable Solid
Fire HazardsLiterature sources indicate that this chemical is flammable. (NTP, 1992)
Fire Potential
Chemistry & industry
Pharmacology
Metabolism/Metabolites
PHENYLHYDROXYLAMINE IS DEGRADED IN AQUEOUS PHOSPHATE BUFFERS AT PHYSIOLOGICAL PH VALUES (6.8-7.4) TO GIVE NITROSOBENZENE, NITROBENZENE, & AZOXYBENZENE. THE REACTION IS OXYGEN-DEPENDENT & SUBJECT TO GENERAL ACID & GENERAL BASE CATALYSIS. AT PH OF APPROX 5.8 IN CACODYLATE BUFFER, IT IS CONVERTED TO P-NITROSOPHENOL IN ADDN TO NITROSOBENZENE, NITROBENZENE, & AZOXYBENZENE.
PARTIALLY PURIFIED, UNTREATED RAT LIVER CYTOSOL CONTAINS AT LEAST 2 ENZYMES WHICH RAPIDLY REDUCE THE C-NITROSO CARCINOGENS, P-NITROSO-N,N-DIMETHYLANILINE, P-NITROSOPHENOL, & 2-NITROSO-1-NAPHTHOL, IN THE PRESENCE OF NADPH OR NADH AT PH 6-7.
Uses & manufacturing
Uses
Used as a chemical intermediate for dyes; metal complexes for camouflage dyes, and hydroquinone; [HSDB]
MFR OF DYES
CHEM INT FOR DYES
CHEM INT FOR METAL COMPLEX USED AS DYE FOR CAMOUFLAGES
CHEM INT, EG, FOR HYDROQUINONE
U.S. Exports
(1979) No Data
(1981) No Data
U.S. Imports
(1979) No Data
(1981) No Data
U.S. Production
2023: 1,000,000 - <8,500,000 lb
(1979) PROBABLY GREATER THAN 4.54X10+6 GRAMS
(1981) PROBABLY GREATER THAN 6.81X10+6 GRAMS
Industry UsesIntermediate
Methods of Manufacturing
FROM PHENOL BY ACTION OF NITROUS ACID IN THE COLD.
PROBABLY BY REACTION OF PHENOL WITH NITROUS ACID
General Manufacturing Information
All Other Basic Organic Chemical Manufacturing
Related reactions
4 records
Compound notes
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