2-Methoxy-4-nitroaniline
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Basic information
- CAS
97-52-9- Standard SMILES
COc1cc([N+](=O)[O-])ccc1N- InChIKey
GVBHRNIWBGTNQA-UHFFFAOYSA-N- Molecular formula
- C7H8N2O3
- Average molar mass
- 168.15 g/mol
- Monoisotopic mass
- 168.05349212
Overview
used as a dye in the textile and printing industries; structure in first source
Names & identifiers
- Preferred name
- 2-Methoxy-4-nitroaniline
- IUPAC
- 2-methoxy-4-nitroaniline
- English name
- 2-Methoxy-4-nitroaniline
- Molecular formula
- C7H8N2O3
- Molecular weight
- 168.15
Names & synonyms
2-METHOXY-4-NITROANILINE97-52-94-Nitro-o-anisidineBenzenamine, 2-methoxy-4-nitro-Fast Red B Base2-Amino-5-nitroanisoleFast Red Base BKako Red B BaseRed B BaseDaito Red Base BDiazo Fast Red Bp-Nitro-o-anisidine
Show more names
FAST RED BRED B ASEMETHOXY-4-NITROANILINE4-NITRO-ORTHO-ANISIDINEAZOIC DIAZO COMPONENT 54-NITRO-2-METHOXYANILINE2-Methoxy-4-nitrobenzenamine
Azoamine Pink ODiabase Red BFast Red 5NA Base5-Nitro-2-anisidineDevol Red ERed Base Ciba VRed Base Irga VRed Base NB
Database identifiers
- CAS
97-52-9- PubChem CID
- 7337
- DTXSID
DTXSID0038700- ChEMBL
CHEMBL1518220- UNII
- DPU26P1846
- EC Number
- 202-588-6
- Nikkaji
- J96.207D
Properties
Computed structural propertiesFilling in
- XLogP
- 1.5
- Topological polar surface area
- 81.1 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 169
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Physical Description
CBI
Deep yellow solid; [NTP] Powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 140 · 140-142 °C(lit.)
- Boiling point
- 337.07 °C · 337.07°C (rough estimate)
- Density
- 1 · 1,211 g/cm3
- refractive index
- 1.601 · 1.6010 (estimate)
- storage temp.
- 30 °C · Store below +30°C.
- solubility
- 0.2 g/l · 0.2g/l
- pka
- 1.02 · 1.02±0.10(Predicted)
- form
- Crystalline Powder
- color
- Yellow to orange
- PH
- 6.2 · 6.2 (0.2g/l, H2O, 20℃)
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
This chemical does not meet GHS hazard criteria for 0.5% (1 of 211) of reports.
Warning
H302 (99.1%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 211 reports by companies from 15 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Warning
Hazard information
Regulatory Information
Chemical: Benzenamine, 2-methoxy-4-nitro-
Benzenamine, 2-methoxy-4-nitro- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenamine, 2-methoxy-4-nitro- 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)
Status: Active Update: 14-10-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/6899
2-Methoxy-4-nitroaniline: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Benzenamine, 2-methoxy-4-nitro-: Human health tier II assessment
Hazards Summary
Suspected of being able to induce methemoglobinemia; Of 14 dye-stuff employees with positive patch test reactions to dye-stuffs, only 1 showed sensitization to this compound; Not a skin or eye irritant in rabbits; No evidence of skin sensitization in guinea pig maximization test; No formation of methemoglobin or increased Heinz bodies detected in cats following oral administration; [NTP] A 28-day oral study of rats produced changes in hematology, increased absolute and relative liver and spleen weights, myocardial necrosis, extramedullary hematopoiesis in the spleen, and a NOEL of 30 mg/kg/day; [JECDB] An irritant; May induce methemoglobinemia; Harmful by inhalation; Toxic by ingestion and skin absorption; Suspected mutagen; [Alfa Aesar MSDS] See p-Nitroaniline. See 5-Nitro-o-anisidine.
Chemistry & industry
Uses & manufacturing
Uses
Used mainly as an intermediate for Pigment Yellow 74 (azo dye); Also used to dye textiles, as a chromogenic agent in the printing industry, and may have minor applications in histological staining; [NTP] Used to make fine chemicals; [ECHA REACH Registrations]
Textiles (Printing, Dyeing, or Finishing) [Category: Industry]
U.S. Production2023: <50,000 lb
Consumer UsesPigment
Industry UsesPigment
General Manufacturing Information
Synthetic Dye and Pigment Manufacturing
Benzenamine, 2-methoxy-4-nitro-: ACTIVE
Applications
Uses2-Methoxy-4-nitroaniline is an important intermediate for preparing organic pigments and color bases of ice dyeing dyestuff. As a benzene dye intermediate, It is generally employed to prepare not only fast pigments but also as a printing and dyeing developer for cotton fabrics. In particular, 2-methoxy-4-nitroaniline is also important in production of some antineoplastic drugs[2-3].
Uses2-Methoxy-4-nitroaniline is used as a photometric reagent for the determination of ethinylestradiol (ETE), a semi-synthetic estrogen that is widely used in oral contraceptives.
General Description2-Methoxy-4-nitroaniline is an important inducer of CYP1A2 owing to its small molecular size.
Upstream & downstream products
Upstream raw materials
Related reactions
41 records
Compound notes
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