2-Methoxy-4-nitroaniline

HCID 7337CAS 97-52-9

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

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 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

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Physical Description · 2 items

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

Safety & regulation

GHS classification

GHS Classification · 6 items

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 · 4 items

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 · 1 item

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 · 4 items

Acute Tox. 4 (99.1%)

Acute toxicity - category 4

Acute toxicity (Oral) - Category 4

Acute toxicity (Oral) - Category 4

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect

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

Chemistry & industry

Uses & manufacturing

Uses · 2 items

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 · 2 items

Synthetic Dye and Pigment Manufacturing

Benzenamine, 2-methoxy-4-nitro-: ACTIVE

Applications · 3 items

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.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
常州帝通化工有限公司+86-0519-88298848 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
武汉欣扬瑞和化学科技有限公司153-07155313 15307155313 · [email protected]

Related reactions

41 records

Linked notes

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