4-Chloroaniline Chemical Properties
- Melting point:
- 67-70 °C(lit.)
- Boiling point:
- 232 °C(lit.)
- 1,43 g/cm3
- vapor density
- 4.4 (vs air)
- vapor pressure
- 0.15 mm Hg ( 25 °C)
- refractive index
- Flash point:
- storage temp.
- Crystalline Solid
- 4.15(at 25℃)
- Beige to brown-purple
- Specific Gravity
- 6.9 (1g/l, H2O, 20℃)
- PH Range
- 6.9 at 1.00000 g/l at 20 °C
- Water Solubility
- 0.3 g/100 mL (20 ºC)
- Henry's Law Constant
- 1.07 at 25 °C (calculated, Howard, 1989)(x 10-5 atm?m3/mol)
- Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, nitrous acid. May be light sensitive.
- CAS DataBase Reference
- 106-47-8(CAS DataBase Reference)
- NIST Chemistry Reference
- EPA Substance Registry System
- p-Chloroaniline (106-47-8)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 2018 6.1/PG 2
- WGK Germany
- Autoignition Temperature
- 685 °C
- Hazard Note
- Toxic/Possible Carcinogen
- HS Code
- Hazardous Substances Data
- 106-47-8(Hazardous Substances Data)
- LD50 orally in rats: 0.31 g/kg (Smyth)
4-Chloroaniline Usage And Synthesis
4-Chloroaniline is a colourless to slightly amber-coloured crystalline solid with a mild aromatic odour. It is Soluble in hot water and organic solvents. 4-Chloroaniline has a moderate vapour pressure and n-octanol/ water partition coefficient. It decomposes in the presence of light and air and at elevated temperatures.
Yellowish-white solid with a mild, sweetish odor. Odor threshold concentration is 287 ppm (quoted, Keith and Walters, 1992).
4-Chloroaniline(is also called PCA) is used as an intermediate in the production of a number of products, including agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products.
ChEBI: A chloroaniline in which the chloro atom is para to the aniline amino group.
A white or pale yellow solid. Melting point 69.5°C.
Air & Water Reactions
Insoluble in cold water. Soluble in hot water [Hawley].
4-Chloroaniline is incompatible with oxidizing agents. Also incompatible with acids, acid chlorides, acid anhydrides and chloroformates. Subject to exothermic decomposition during high-temperature distillation. Incompatible with nitrous acid.
Toxic by inhalation and ingestion. Possible carcinogen.
Inhalation or ingestion causes bluish tint to fingernails, lips, and ears indicative of cyanosis; headache, drowsiness, and nausea, followed by unconsciousness. Liquid can be absorbed through skin and cause similar symptoms. Contact with eyes causes irritation.
Special Hazards of Combustion Products: Irritating and toxic hydrogen chloride and oxides of nitrogen may form in fires.
Confirmed carcinogen with experimental neoplastigenic and tumorigenic data. Poison by ingestion, inhalation, sh contact, subcutaneous, and intravenous routes. A skin and severe eye irritant. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx. See also ANILINE DYES
Biological. In an anaerobic medium, the bacteria of the Paracoccus sp. converted 4-
chloroaniline to 1,3-bis(p-chlorophenyl)triazene and 4-chloroacetanilide with product yields of 80
and 5%, respectively (Minard et al., 1977). In a field experiment, [14C]4-chloroaniline was applied
to a soil at a depth of 10 cm. After 20 wk, 32.4% of the applied amount was recovered in soil.
Metabolites identified include 4-chloroformanilide, 4-chloroacetanilide, 4-chloronitrobenzene, 4-
chloronitrosobenzene, 4,4′-dichloroazoxybenzene, and 4,4′-dichloroazobenzene (Freitag et al.,
Soil. 4-Chloroaniline covalently bonds with humates in soils to form quinoidal structures followed by oxidation to yield a nitrogen-substituted quinoid ring. A reaction half-life of 13 min was determined with one humic compound (Parris, 1980). Catechol, a humic acid monomer, reacted with 4-chloroaniline yielding 4,5-bis(4-chlorophenylamino)-3,5-cyclohexadiene-1,2-dione (Adrian et al., 1989).
Photolytic. Under artificial sunlight, river water containing 2–5 ppm 4-chloroaniline photodegraded to 4-aminophenol and unidentified polymers (Mansour et al., 1989). Photooxidation of 4-chloroaniline (100 μM) in air-saturated water using UV light (λ >290 nm) produced 4-chloronitrobenzene and 4-chloronitrosobenzene. About 6 h later, 4-chloroaniline completely reacted leaving dark purple condensation products (Miller and Crosby, 1983). In a similar study, irradiation of an aqueous solution in the range of 290–350 nm resulted in the formation of the intermediate 4-iminocyclohexa-2,5-dienylidene (Othmen et al., 2000). A carbon dioxide yield of 27.7% was achieved when 4-chloroaniline adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
A rate constant of 8.3 x 10-11 cm3/molecule?sec was reported for the gas-phase reaction of 4- chloroaniline and OH radicals in air (Wahner and Zetzsch, 1983).
Chemical/Physical. 4-Chloroaniline will not hydrolyze to any reasonable extent (Kollig, 1993).
Pizzigallo et al. (1998) investigated the reaction of 4-chloroaniline with ferric oxide and two forms of manganese dioxide [birnessite (δ-MnO2) and pyrolusite (MnO2)] within the pH range of 4–8 at 25 °C. The reaction rate of 4-chloroaniline was in the order birnessite > pyrolusite > ferric oxide. At pH 4.0, the reaction with birnessite was so rapid that the reaction could not be determined. Half-lives for the reaction of 4-chloroaniline with pyrolusite and ferric oxide were 383 and 746 min, respectively. The reaction rate decreased as the pH was increased. The only oxidation compounds identified by GC/MS were 4,4′-dichloroazobenzene and 4-chloro-4′- hydroxydiphenylamine.
Crystallise the aniline from MeOH, pet ether (b 30-60o), or 50% aqueous EtOH, then *benzene/pet ether (b 60-70o), and then dry it in a vacuum desiccator. It can be distilled under vacuum (b 75-77o/3mm). It sublimes in a very high vacuum. The acetate crystallises from aqueous MeOH (m 178o, 180o) or EtOH or AcOH (m 173-174o) and has b 331.3o/760mm. [Beilstein 12 III 1325, 12 IV 1116.]
4-Chloroaniline Preparation Products And Raw materials
- 4-CHLOROPHENYL ISOTHIOCYANATE
- ACID YELLOW 40
- 4-Chlorophenyl isocyanate
- 4-Chlorobenzenamine hydrochloride
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