4-Chloroaniline

4-Chloroaniline Chemical Properties
Melting point 67-70 °C (lit.)
Boiling point 232 °C (lit.)
density 1,43 g/cm3
vapor density 4.4 (vs air)
vapor pressure 0.15 mm Hg ( 25 °C)
refractive index 1.5546
Fp 120°C
storage temp. Store below +30°C.
solubility 2.2g/l
form Crystalline Solid
pka4.15(at 25℃)
color Beige to brown-purple
Specific Gravity1.2417
OdorSweetish
PH6.9 (1g/l, H2O, 20℃)
PH Range6.9 at 1.00000 g/l at 20 °C
Water Solubility 0.3 g/100 mL (20 ºC)
Merck 14,2118
BRN 471359
Henry's Law Constant1.07 at 25 °C (calculated, Howard, 1989)(x 10-5 atm?m3/mol)
Stability:Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, nitrous acid. May be light sensitive.
LogP1.83 at 25℃
CAS DataBase Reference106-47-8(CAS DataBase Reference)
IARC2B (Vol. 57) 1993
NIST Chemistry Referencep-Chloroaniline(106-47-8)
EPA Substance Registry Systemp-Chloroaniline (106-47-8)
Safety Information
Hazard Codes T,N,F
Risk Statements 45-23/24/25-43-50/53-52/53-39/23/24/25-11-51/53
Safety Statements 53-45-60-61-36/37-16-7
RIDADR UN 2018 6.1/PG 2
WGK Germany 3
RTECS BX0700000
8-10-23
Autoignition Temperature685 °C
Hazard Note Toxic/Possible Carcinogen
TSCA Yes
HazardClass 6.1
PackingGroup II
HS Code 29214210
Hazardous Substances Data106-47-8(Hazardous Substances Data)
ToxicityLD50 orally in rats: 0.31 g/kg (Smyth)
MSDS Information
ProviderLanguage
4-Chlorobenzenamine English
ACROS English
SigmaAldrich English
ALFA English
4-Chloroaniline Usage And Synthesis
Chemical Properties4-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.
Physical propertiesYellowish-white solid with a mild, sweetish odor. Odor threshold concentration is 287 ppm (quoted, Keith and Walters, 1992).
Uses4-Chloroaniline is an important raw material in production of agricultural chemicals, azo dyes and pigments, cosmetics, and pharmaceutical products. It is used as an intermediate in the manufacture of chromophore AS-LB, as well as in pharmaceutical intermediates such as chlordiazepoxide and phena tincture. It is also an intermediate for the herbicide Anilofos, the insecticide chlorbenzuron and the plant growth regulator Inabenfide.
DefinitionChEBI: 4-chloroaniline is a chloroaniline in which the chloro atom is para to the aniline amino group. It is a chloroaniline and a member of monochlorobenzenes.
Application4-Chloroaniline is an important building block used in the chemical industry for the production of drugs and dyestuffs. Some benzodiazepine drugs use 4-chloroaniline in their manufacture.
Preparationsynthesis of 4-Chloroaniline: p-chloronitrobenzene is used as raw material, Raney nickel is used as catalyst, ethanol is used as solvent, reaction temperature is 50~70°C , hydrogenation pressure is 3.04~3.55MPa, and medium pH=5~6 conditions, carry out Catalytic hydrogenation reaction to obtain 4-Chloroaniline.
Synthesis Reference(s)Journal of the American Chemical Society, 99, p. 98, 1977 DOI: 10.1021/ja00443a018
Synthesis, p. 48, 1987 DOI: 10.1055/s-1987-27838
General DescriptionP-chloroaniline appears as a white or pale yellow solid. Melting point 69.5°C.
Air & Water ReactionsInsoluble in cold water. Soluble in hot water [Hawley].
Reactivity Profile4-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.
HazardToxic by inhalation and ingestion. Possible carcinogen.
Health HazardInhalation 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.
Fire HazardSpecial Hazards of Combustion Products: Irritating and toxic hydrogen chloride and oxides of nitrogen may form in fires.
Flammability and ExplosibilityFlammable
Safety ProfileConfirmed 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
Environmental fateBiological. 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., 1984).
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.
Purification MethodsCrystallise 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.]
ACID YELLOW 40 1-(3,4-DICHLOROPHENYL)-2-THIOUREA Chloroaniline 2,3,4-TRICHLORONITROBENZENE 4-CHLOROPHENYL ISOTHIOCYANATE Chlorpropham N-Acetyl-4-chloroaniline,N-Acetyl-p-chloroaniline DICHLORPHENAMIDE BULK POWDER 4-Chloro-7-nitrobenzofurazan 3,4-Dichloroaniline 4-Chlorobenzenamine hydrochloride 4-Chlorophenyl isocyanate 2,4-Dichloroaniline 4-Chloroaniline 2-Chloroaniline 2,5-Dichloroaniline 3-Chloroaniline 2,6-Dichloroaniline

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