p-Anisidine Chemical Properties
- Melting point:
- 56-59 °C(lit.)
- Boiling point:
- 240-243 °C(lit.)
- vapor density
- vapor pressure
- 0.02 hPa (20 °C)
- refractive index
- Flash point:
- 122 °C
- storage temp.
- 5.34(at 25℃)
- Specific Gravity
- dark gray to brown
- 7.7 (1g/l, H2O, 20℃)
- Water Solubility
- 21 g/L (20 ºC)
- Henry's Law Constant
- (x 10-8 atm?m3/mol): 6.62 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
- Exposure limits
- NIOSH REL: TWA 0.5 mg/m3, IDLH 50 mg/m3; OSHA PEL: TWA 0.5 mg/m3; ACGIH TLV: TWA 0.1 ppm (adopted).
- CAS DataBase Reference
- 104-94-9(CAS DataBase Reference)
- 3 (Vol. 27, Sup 7) 1987
- NIST Chemistry Reference
- Benzenamine, 4-methoxy-(104-94-9)
- EPA Substance Registry System
- p-Anisidine (104-94-9)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 2811 6.1/PG 3
- WGK Germany
- Autoignition Temperature
- 959 °F
- HS Code
- Hazardous Substances Data
- 104-94-9(Hazardous Substances Data)
- Acute oral LD50 for rats 1,400 mg/kg, mice 810 mg/kg, rabbits 2,900 mg/kg (quoted, RTECS, 1985).
p-Anisidine Usage And Synthesis
Anisidine exists as ortho-, meta-, and paraisomers. They have characteristic amine (fishy) odors.
grey to brown crystalline powder, granules
Yellow to light brown powder, leaflets, solid or crystals with a characteristic amine or ammonialike odor
p-Anisidine is used mostly for producing dyes, and some smaller quantities are employed in making pharmaceuticals and liquid crystals.
p-Anisidine is used as a reagent to indicate the secondary stage of the oxidation, it is one of the three possible isomers of the Anisidine or methoxyaniline. The other two isomers are o-Anisidine (2-methoxyaniline) and m-Anisidine (3-methoxyaniline).
The p-anisidine is widely used as an intermediate in the production of numerous azo and triphenylmethane dyes, and pigments. It is also used in the production of pharmaceuticals including the guaiacol expectorant, as an antioxidant for polymercaptan resins, and as a corrosion inhibitor for steel. Apart from the beneficial use of p-anisidine, it is toxic for human beings. The acute exposure may cause skin irritation, whereas the chronic exposure may cause headaches, vertigo, and blood complications like sulfhemoglobin, and methemoglobin. The oral exposure to anisidine hydrochloride resulted in cancer of the urinary bladder in male and female rats.
In the preparation of azo dyes; corrosion inhibitor; chemical intermediate
Journal of the American Chemical Society, 99, p. 98, 1977 DOI: 10.1021/ja00443a018
The Journal of Organic Chemistry, 49, p. 1434, 1984
Tetrahedron Letters, 21, p. 2603, 1980
Brown crystals or dark brown solid. Characteristic amine odor.
Air & Water Reactions
Insoluble in water.
p-Anisidine may be sensitive to heat, light and moisture. Reacts with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. Incompatible with alkaline materials. Incompatible with aldehydes, ketones and nitrates.
Strong irritant. Toxic when absorbed through the skin. Questionable carcinogen.
p-Anisidine is flammable.
Moderately toxic by several routes. A mild sensitizer. May cause a contact dermatitis. Mutation data reported. Questionable carcinogen. See also ANILINE. When heated to decomposition it emits toxic fumes of Nox
Anisidines are used in the manufacture of azo dyes; pharmaceuticals; textile-processing chemicals Incompatibilities: Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine,bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Attacks some coatings and some forms of plastic and rubber.
Available data were inadequate to evaluate the carcinogenicity of p-anisidine.
Chemical/Physical. Releases toxic nitrogen oxides when heated to decomposition (Sax and Lewis, 1987).
UN2431 Anisidines, Hazard Class: 6.1; Labels: 6.1-Poisonous materials
Crystallise p-anisidine from H2O or aqueous EtOH. Dry it in a vacuum oven at 35o for 6hours and store it in a dry box. [More et al. J Am Chem Soc 108 2257 1986.] Purify it also by vacuum sublimation [Guarr et al. J Am Chem Soc 107 5104 1985]. [Beilstein 13 IV 1015.]
Dissolve in combustible solvent (alcohols, benzene, etc.) and spray solution into furnace equipped with afterburner and scrubber, or burn spill residue on sand and soda ash absorbent in a furnace.
p-Anisidine Preparation Products And Raw materials
- 4-Aminobenzoic acid
- Azoic Diazo Component 1
- 2,4-DIMETHOXYPHENYL ISOCYANATE
- 4-Methoxyphenyl isocyanate
- Anise oil
- 4-Amino-benzenesulfonic acid monosodium salt
- 4-Methoxyphenylacetic acid
- 4-Aminophenylacetic acid
- Anisic acid
- Sulfanilic acid
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