| Identification | More | [Name]
4-Chloroaniline | [CAS]
106-47-8 | [Synonyms]
1-AMINO-4-CHLOROBENZENE
4-CHLOROANILINE
4-CHLOROBENZENAMINE
4-CHLORO-PHENYLAMINE
AKOS BBS-00003661
PARA CHLORO ANILINE
P-CHLOROANILINE
1,4-aminochlorobenzene
4-amino-1-chlorobenzene
4-aminochlorobenzene
4-Chloranilin
4-chloranilin(czech)
4-Chloro-1-aminobenzene
4-chloro-anilin
4-Chloroaniline,p-Chloroaniline
4-chlorobenzamine
4-chloro-benzenamin
4-chloro-Benzeneamine
Aniline, 4-chloro-
Aniline, p-chloro- | [EINECS(EC#)]
203-401-0 | [Molecular Formula]
C6H6ClN | [MDL Number]
MFCD00007835 | [Molecular Weight]
127.57 | [MOL File]
106-47-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white or pale yellow solid | [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. ]
2-8°C | [solubility ]
2.2g/l | [form ]
Crystalline Solid | [pka]
4.15(at 25℃) | [color ]
Beige to brown-purple | [Specific Gravity]
1.2417 | [Odor]
Sweetish | [PH]
6.9 (1g/l, H2O, 20℃) | [PH Range]
6.9 at 1.00000 g/l at 20 °C | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, acids, acid chlorides, acid anhydrides, chloroformates, nitrous acid. May be light sensitive. | [Water Solubility ]
0.3 g/100 mL (20 ºC) | [Merck ]
14,2118 | [BRN ]
471359 | [Henry's Law Constant]
1.07 at 25 °C (calculated, Howard, 1989)(x 10-5 atm?m3/mol) | [LogP]
1.83 at 25℃ | [Uses]
Dye intermediate, pharmaceuticals, agricultural
chemicals. | [CAS DataBase Reference]
106-47-8(CAS DataBase Reference) | [IARC]
2B (Vol. 57) 1993 | [NIST Chemistry Reference]
p-Chloroaniline(106-47-8) | [Storage Precautions]
Air sensitive;Light sensitive | [EPA Substance Registry System]
106-47-8(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T,N,F | [Risk Statements ]
R45:May cause cancer.
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed .
R43:May cause sensitization by skin contact.
R50/53:Very Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R52/53:Harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R39/23/24/25:Toxic: danger of very serious irreversible effects through inhalation, in contact with skin and if swallowed .
R11:Highly Flammable. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S60:This material and/or its container must be disposed of as hazardous waste .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S36/37:Wear suitable protective clothing and gloves .
S16:Keep away from sources of ignition-No smoking .
S7:Keep container tightly closed . | [RIDADR ]
UN 2018 6.1/PG 2
| [WGK Germany ]
3
| [RTECS ]
BX0700000
| [F ]
8-10-23 | [Autoignition Temperature]
685 °C | [Hazard Note ]
Toxic/Possible Carcinogen | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
II | [HS Code ]
29214210 | [Safety Profile]
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 | [Hazardous Substances Data]
106-47-8(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 0.31 g/kg (Smyth) |
| Hazard Information | Back Directory | [Description]
p-Chloroaniline, 1-amino-4-
chlorobenzene,is a white to light
amber, crystalline solid at room temperature. It is used as
an intermediate for pesticides, pharmaceuticals,
pigments, and dyes. Production is similar to that
of m-chloroaniline . | [Chemical Properties]
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. | [Physical properties]
Yellowish-white solid with a mild, sweetish odor. Odor threshold concentration is 287 ppm
(quoted, Keith and Walters, 1992). | [Application]
4-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. | [Definition]
ChEBI: 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. | [Preparation]
synthesis 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 Description]
P-chloroaniline appears as a white or pale yellow solid. Melting point 69.5°C. | [Air & Water Reactions]
Insoluble in cold water. Soluble in hot water [Hawley]. | [Reactivity Profile]
4-Chloroaniline(106-47-8) 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. | [Hazard]
Toxic by inhalation and ingestion. Possible
carcinogen. | [Health Hazard]
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. | [Fire Hazard]
Special Hazards of Combustion Products: Irritating and toxic hydrogen chloride and oxides of nitrogen may form in fires. | [Flammability and Explosibility]
Flammable | [Environmental Fate]
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.,
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 Methods]
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.] |
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