Basic information
- 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
Show more names
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 properties
- 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
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℃)
- Water Solubility
- slightly soluble
- BRN
- 879619 · 879619
- InChI
- 1S/C7H8N2O3/c1-12-7-4-5(9(10)11)2-3-6(7)8/h2-4H,8H2,1H3
- InChIKey
- GVBHRNIWBGTNQA-UHFFFAOYSA-N
- SMILES
- COc1cc(ccc1N)[N+]([O-])=O
- CAS DataBase Reference
- 97 · 97-52-9(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 26 P1846 · DPU26P1846
- NIST Chemistry Reference
- 2 · Benzenamine, 2-methoxy-4-nitro-(97-52-9)
- EPA Substance Registry System
- 2 · 2-Methoxy-4-nitroaniline (97-52-9)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07,GHS08,GHS09
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H371-H373-H341-H351-H411
- Precautionary statements
- 501 · P501-P273-P260-P270-P202-P201-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P405
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-20/21/22
- Safety Statements
- 26 · 26-37/39-36/37
- RIDADR
- 3077 · UN 3077 9 / PGIII
- WGK Germany
- 2 · 2
- RTECS
- 7170000 · BZ7170000
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HS Code
- 29222900 · 29222900
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralAquatic · Acute Tox. 4 OralAquatic Chronic 2Carc. 2
- REACH Registrations
- Active
Safety & regulation
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
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.
Hazard Classes and Categories
Acute Tox. 4 (99.1%)
Acute toxicity - category 4
Acute toxicity (Oral) - Category 4
Acute toxicity (Oral) - Category 4
Toxicology
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 2
- tsca
- TSCA listed
- rtecs
- BZ7170000
- ridadr
- UN 3077 9 / PGIII
- hs_code
- 29222900
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07,GHS08,GHS09
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-37/39-36/37
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H371-H373-H341-H351-H411
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralAquatic Chronic 2Carc. 2
- Precautionary statements
- P501-P273-P260-P270-P202-P201-P264-P280-P302+P352-P391-P337+P313-P305+P351+P338-P308+P311-P362+P364-P332+P313-P301+P312+P330-P405
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]
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
Downstream products
Suppliers50 total
Related reactions
Linked notes
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