4-Chloroaniline

ChemicalBook > CAS DataBase List > 4-Chloroaniline

Product Name: 4-Chloroaniline
CAS No.: 106-47-8
Chemical Name: 4-Chloroaniline
Synonyms: P-CHLOROANILINE;PARA CHLORO ANILINE;PARA-CHLORANILINE;4-CHLOROBENZENAMINE;4-Chloranilin;4-CHLORO-PHENYLAMINE;4-Chloroaniline, 98% 5GR;NSC 36941;NCI-C02039;4-Choraniline
CBNumber: CB8147309
Molecular Formula: C6H6ClN
Formula Weight: 127.57
MOL File: 106-47-8.mol

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4-Chloroaniline Property

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
Flash point:: 120°C
storage temp.: Store below +30°C.
solubility: 2.2g/l
pka: 4.15(at 25℃)
form: Crystalline Solid
Specific Gravity: 1.2417
color: Beige to brown-purple
PH: 6.9 (1g/l, H2O, 20℃)
Odor: Sweetish
PH Range: 6.9 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 Constant: 1.07 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.
LogP: 1.83 at 25℃
CAS DataBase Reference: 106-47-8(CAS DataBase Reference)
NIST Chemistry Reference: p-Chloroaniline(106-47-8)
IARC: 2B (Vol. 57) 1993
EPA Substance Registry System: p-Chloroaniline (106-47-8)

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Safety

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
F: 8-10-23
Autoignition Temperature: 685 °C
Hazard Note: Toxic/Possible Carcinogen
TSCA: Yes
HazardClass: 6.1
PackingGroup: II
HS Code: 29214210
Hazardous Substances Data: 106-47-8(Hazardous Substances Data)
Toxicity: LD50 orally in rats: 0.31 g/kg (Smyth)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H350May cause cancer

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 8.02613
Product name: 4-Chloroaniline
Purity: for synthesis
Packaging: 100g
Price: $30.6
Updated: 2024/03/01

Sigma-Aldrich

Product number: 8.02613
Product name: 4-Chloroaniline
Purity: for synthesis
Packaging: 500g
Price: $73.8
Updated: 2024/03/01

Sigma-Aldrich

Product number: 35823
Product name: 4-Chloroaniline
Purity: PESTANAL , analytical standard
Packaging: 1g
Price: $25.8
Updated: 2024/03/01

Sigma-Aldrich

Product number: 1111908
Product name: 4-Chloroaniline
Purity: United States Pharmacopeia (USP) Reference Standard
Packaging: 200mg
Price: $447
Updated: 2024/03/01

Sigma-Aldrich

Product number: 40305
Product name: 4-Chloroaniline solution
Purity: certified reference material, 5000?μg/mL in methanol
Packaging: 1mL
Price: $55.4
Updated: 2022/05/15

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4-Chloroaniline Chemical Properties,Usage,Production

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).

Uses

4-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.

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.

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.

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 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

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

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.]

4-Chloroaniline Preparation Products And Raw materials

Raw materials

4-Chloronitrobenzene Iron filings Nickel aluMinuM Nickel Iron

Preparation Products

imidazol-2-ylamine sulphate cintofen 2-amino-5-chloro-diphenyl methanol 1-CHLORO-4-ISOCYANOBENZENE 2-Amino-5-chlorobenzophenone 4-Chlorophenylhydrazine polyaniline synthesized by means of condensation polymerization 6-CHLORO-2-(TRIFLUOROMETHYL)QUINOLINE-4-CARBOXYLIC ACID Chlorhexidine Diacetate 2-Amino-5-chloro-2'-fluorobenzophenone Tenidap 2,6-Dichlorobenzothiazole N-(2-[4-(4-CHLOROPHENYL)PIPERAZIN-1-YL]ETHYL)-3-METHOXYBENZAMIDE 5-Chloroorthanilic acid Naphthol AS-E 1-(4-Chlorophenyl)piperazine 4-CHLORO-(N-BOC)ANILINE 97 N-(4-chlorophenyl)-2-hydroxy-9H-carbazole-3-carboxamide FLURAZEPAM Anilofos 4-Chlorophenyl isocyanate Efavirenz 3-Chlorophenol 4-(4-(Chlorophenyl)imino)-1-isopropyl piperidine Diflubenzuron Nitrazepam Chlorhexidine diacetate Lorcainide chlorbenzuron 6-CHLORO-2-METHYLQUINOLINE 5-AMINO-1-(4-CHLOROPHENYL)-1H-PYRAZOLE-4-CARBONITRILE Cloflucarban N-(4-chlorophenyl)-1-isopropylpiperidin-4-amine

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View Lastest Price from 4-Chloroaniline manufacturers

Hebei Fengqiang Trading Co., LTD

Product: 4-Chloroaniline 106-47-8
Price: US $100.00/bag
Min. Order: 1bag
Purity: 99
Supply Ability: 5000
Release date: 2023-08-28

Hebei Guanlang Biotechnology Co., Ltd.

Product: 4-Chloroaniline 106-47-8
Price: US $10.00/Kg/Drum
Min. Order: 1KG
Purity: 99.5%
Supply Ability: 100 TON
Release date: 2020-12-02

Hebei Guanlang Biotechnology Co., Ltd.

Product: 4-Chloroaniline 106-47-8
Price: US $10.00/Kg/Drum
Min. Order: 1KG
Purity: 99%
Supply Ability: 100
Release date: 2020-12-10

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