2-nitroaniline

C6H6N2O2

CAS88-74-4
GHS06 Gefahrensymbol: Giftig – Totenkopf mit Knochen
GHS08 Gefahrensymbol: Gesundheitsgefahr – Gesundheitsgefahr
Danger

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Identification

CAS Number
88-74-4
EC Number
201-855-4
UN Number
1661
Index Number
612-012-00-9
PubChem CID
6946

Physical-chemical properties

Molecular Formula
C6H6N2O2
Molar Mass
138.12 g/mol
IUPAC Name
2-nitroaniline

Chemical Identifiers

InChI
InChI=1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2
InChI Key
DPJCXCZTLWNFOH-UHFFFAOYSA-N

Overview

2-nitroaniline (CAS 88-74-4) is an aromatic amine compound with nitro substituent exhibiting significant toxicological properties and industrial utility. This yellow to orange crystalline organic compound represents a fundamental building block in chemical synthesis, characterized by its dual functional groups - an amino group and a nitro group positioned ortho to each other on a benzene ring. With the molecular formula C6H6N2O2 and molecular weight of 138.12 g/mol, 2-nitroaniline belongs to the nitroaniline family of compounds that serve as crucial intermediates in various industrial processes. The substance presents notable safety considerations, classified under multiple hazard categories including acute toxicity (Acute Tox. 3) through oral, dermal, and inhalation routes, specific target organ toxicity with repeated exposure (STOT RE 2), and chronic aquatic toxicity. The GHS06 and GHS08 pictograms emphasize its toxic and health hazard properties, requiring careful handling protocols and appropriate personal protective equipment during use. 2-nitroaniline finds primary applications in dye manufacturing as an intermediate for producing various colorants and pigments, pharmaceutical synthesis for developing active pharmaceutical ingredients, and chemical manufacturing processes. The compound shares structural similarities with related aromatic amines such as N-methylaniline, though each exhibits distinct reactivity patterns based on their specific substituents. Industrial users appreciate 2-nitroaniline's reliability in synthetic transformations, particularly reduction reactions to form corresponding diamines and coupling reactions in dye chemistry. Its ortho-substitution pattern provides unique reactivity compared to meta and para isomers, making it valuable for specific synthetic pathways. OYSI maintains reliable supply chains for 2-nitroaniline, ensuring consistent availability for European industrial customers requiring this essential chemical intermediate.

Safety & Classification

Danger
Classification:

Acute Tox. 3 *; Acute Tox. 3 *; Acute Tox. 3 *; STOT RE 2 *; Aquatic Chronic 3

HHazard Statements (H-Statements)

Describe the nature and severity of the hazard

H331

Toxic if inhaled.

H311

Toxic in contact with skin.

H301

Toxic if swallowed.

H373

May cause damage to organs through prolonged or repeated exposure.

H412

Harmful to aquatic life with long lasting effects.

Classification according to CLP Regulation (EC) No 1272/2008. The complete list of hazard and precautionary statements can be found in the Safety Data Sheet (SDS).

First Aid Measures

Inhalation

Toxic

Measures if vapours or dust are inhaled

First Aid Actions

  • +P304IF INHALED:
  • +P340Remove person to fresh air and keep comfortable for breathing.
  • +P311Call a POISON CENTER/doctor.

Related hazard statements:

Skin Contact

Toxic

Measures if substance contacts the skin

First Aid Actions

  • +P302IF ON SKIN:
  • +P352Wash with plenty of water.
  • +P361Take off immediately all contaminated clothing.
  • +P313Get medical advice/attention.

Related hazard statements:

Ingestion

Toxic

Measures if substance is accidentally swallowed

First Aid Actions

  • +P301IF SWALLOWED:
  • +P330Rinse mouth.
  • +P331Do NOT induce vomiting.
  • +P310Immediately call a POISON CENTER/doctor.

Related hazard statements:

General Measures

Emergency 112 | Poison Control: +49 30 19240 (DE), +33 1 45 42 59 59 (FR), +31 30 274 88 88 (NL)

First aid measures are based on CLP classification and associated P-statements. They do not replace the Safety Data Sheet (SDS). In case of emergency, always consult the full SDS and a physician.

Transport (ADR)

UN Number1661
ADR Class6.1
Packing GroupII
Tunnel CodeD/E
Proper Shipping Name2-Nitroanilin, geschmolzen
Marine PollutantNo

Frequently Asked Questions

What is 2-nitroaniline?

2-nitroaniline is an organic chemical compound with the molecular formula C6H6N2O2 and CAS number 88-74-4. This aromatic amine features both an amino group and a nitro group attached to a benzene ring in ortho position. With a molecular weight of 138.12 g/mol, it appears as yellow to orange crystalline solid. It is classified as a hazardous substance with acute toxicity and potential health effects, requiring careful handling in industrial applications.

What are the physicochemical properties of 2-nitroaniline?

2-nitroaniline is a yellow to orange crystalline solid at room temperature with a characteristic aromatic odor. It has limited solubility in water but dissolves well in organic solvents like ethanol and acetone. The compound has a melting point around 71-73°C and exhibits stability under normal conditions. Its aromatic structure gives it UV-absorbing properties, and it can undergo various chemical reactions typical of both anilines and nitro compounds.

What is 2-nitroaniline used for?

2-nitroaniline serves primarily as an intermediate in the synthesis of dyes, pigments, and pharmaceuticals. It is widely used in the production of azo dyes, particularly yellow and orange colorants for textiles and printing inks. The compound also functions as a precursor for various chemical syntheses, including the manufacture of antioxidants, rubber chemicals, and specialty organic compounds. Its dual functional groups make it valuable in organic synthesis reactions.

How to handle 2-nitroaniline safely?

2-nitroaniline requires strict safety measures due to its acute toxicity classification. Always wear appropriate personal protective equipment including chemical-resistant gloves, safety goggles, and protective clothing. Work in well-ventilated areas or under fume hoods to avoid inhalation. Prevent skin and eye contact, and avoid ingestion. Use non-sparking tools and equipment. Ensure emergency eyewash stations and safety showers are readily accessible when handling this substance.

How to store 2-nitroaniline correctly?

2-nitroaniline should be stored in tightly sealed containers in a cool, dry, well-ventilated area away from heat sources and direct sunlight. Keep containers in secondary containment to prevent spills. Store away from incompatible materials such as strong oxidizers, acids, and alkalis. Maintain storage temperatures below 25°C and ensure proper labeling according to GHS requirements. Access should be restricted to trained personnel only.

What to do in case of contact with 2-nitroaniline?

In case of skin contact with 2-nitroaniline, immediately remove contaminated clothing and wash the affected area thoroughly with soap and water for at least 15 minutes. For eye contact, flush eyes with clean water for 15-20 minutes. If inhaled, move the person to fresh air immediately. If ingested, do not induce vomiting and seek immediate medical attention. In all cases of exposure, contact emergency medical services promptly and provide the safety data sheet.

How to dispose of 2-nitroaniline appropriately?

2-nitroaniline disposal must comply with local and national hazardous waste regulations due to its toxicity classification. The substance should be collected in appropriate containers and labeled clearly for hazardous waste disposal. Contact licensed waste disposal companies for proper treatment, which typically involves high-temperature incineration at specialized facilities. Never dispose of this chemical in regular waste streams, sewers, or the environment. Maintain disposal records as required by regulations.

How to transport 2-nitroaniline?

2-nitroaniline is classified under ADR as Class 6.1 (toxic substances), Packing Group II, requiring specific transport protocols. Packages must be properly labeled with appropriate hazard symbols and shipping names. Use UN-approved packaging designed for toxic solids, and ensure vehicles are properly placarded. Transport documentation must include safety data sheets and emergency response information. Only trained personnel should handle transportation, following ADR regulations for dangerous goods.

Is 2-nitroaniline subject to specific regulations?

2-nitroaniline is regulated under various European frameworks including REACH regulation for registration and evaluation. It falls under CLP regulation for classification, labeling, and packaging requirements, indicated by its GHS pictograms (GHS06, GHS08) and 'Danger' signal word. The substance is not currently listed as an SVHC (Substance of Very High Concern). Industrial users must comply with occupational exposure limits and safety requirements established by national authorities.

Where to buy 2-nitroaniline in Europe?

2-nitroaniline is available through OYSI, a trusted European distributor of chemical products. OYSI provides high-quality 2-nitroaniline with proper documentation including safety data sheets and certificates of analysis. As a specialized chemical distributor, OYSI ensures compliance with European regulations and offers technical support for industrial applications. Contact OYSI directly for availability, specifications, and delivery options to your location within Europe.

Data Sources

Classification per CLP Regulation (EC) No 1272/2008. Data from ECHA and PubChem.