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2-Chlorophenol

O-Chlorophenol

CAS: 95-57-8

Molecular Formula: C6H5ClO

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2-Chlorophenol - Names and Identifiers

Name O-Chlorophenol
Synonyms septi-kleen
2-Chorophenol
o-chloro-pheno
O-Chlorophenol
2-chloro-pheno
2-Chlorophenol
2-chlorophenol
CHLOROPHENOL2-
2-CHLOROPHENOL
chloro-2phenol
O-CHLORO PHENOL
CHLOROPHENOL(O-)
o-chlorophenicacid
rcrawastenumberu048
2-Hydroxychlorobenzene
2-hydroxychlorobenzene
1-Chloro-2-hydroxybenzene
2-chloro-1-hydroxybenzene
1-chloro-2-hydroxybenzene
2-Chloro-1-hydroxy-benzene
2-chlorophenol(o-chlorophenol)
Chlorophenol, 2-chlorophenolate
CAS 95-57-8
EINECS 202-433-2
InChIKey ISPYQTSUDJAMAB-UHFFFAOYSA-N

2-Chlorophenol - Physico-chemical Properties

Molecular FormulaC6H5ClO
Molar Mass128.56
Density1.241 g/mL at 25 °C (lit.)
Melting Point8 °C (lit.)
Boling Point175-176 °C (lit.)
Flash Point147°F
Water Solubility28.5 g/L (20 ºC)
Solubility alcohol: freely soluble
Vapor Presure13.3 hPa (50 °C)
Appearanceneat
ColorClear Colourless to Pale Orange
Merck14,2154
BRN1905114
pKa8.49(at 25℃)
Storage Conditionunder inert gas (Argon)
StabilityStable. Hygroscopic. Combustible. Incompatible with oxidizing agents, acid anhydrides, acid chlorides.
Refractive Indexn20/D 1.558(lit.)
Physical and Chemical Properties

density

1.26

freezing point

7-8°C

boiling point

175-176°C

UseFor pharmaceuticals, pesticides and dyes and other raw materials for organic synthesis

2-Chlorophenol - Risk and Safety

Risk CodesR20/21/22 - Harmful by inhalation, in contact with skin and if swallowed.
R51/53 - Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
R39/23/24/25 -
R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed.
R11 - Highly Flammable
Safety DescriptionS28 - After contact with skin, wash immediately with plenty of soap-suds.
S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. 
S28A -
S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37 - Wear suitable protective clothing and gloves.
S16 - Keep away from sources of ignition.
S7 - Keep container tightly closed.
UN IDsUN 2021 6.1/PG 3
WGK Germany2
RTECSSK2625000
FLUKA BRAND F CODES9
TSCAYes
HS Code29081000
Hazard Class6.1
Packing GroupIII
ToxicityLD50 orally in rats: 0.67 g/kg (Deichmann)

2-Chlorophenol - Reference Information

use p-chlorophenol is mainly used in pesticide, medicine, dye, plastic and other industries, as well as denatured agent of alcohol and selective solvent of refined mineral oil. It can also be used for microscopic analysis and plant growth promoters. Used to synthesize dyes, react with dilute nitric acid to form 1. dinitroliates are dye intermediates; a variety of dyes can be further synthesized, such as neutral brilliant green BL and so on. It is used to make dyes and drugs, as a denaturant of alcohol and a selective solvent for refined mineral oil.
In the pesticide industry, it is mainly used for the synthesis of tripiconine, midacone, wool fungicide, anti-shrein (multifunctional plant growth regulator), propionate phosphorus (systemic insecticide), poisonous mouse phosphorus, Insecticide, mite egg ester (non-systemic acaricide), acaricide ester, acaricide ether; used in the pharmaceutical industry to carboxylate sodium 5-chloro-2-hydroxybenzoate, synthesis of antamine, p-chlorophenoxyisobutyric acid and other drugs; it is also used to synthesize the antioxidant BHA (butyl hydroxyanisole) and so on.
o-chlorophenol is an intermediate of the insecticide profenofos.
Used in organic synthesis. O-chlorophenol is obtained by phosgenation to obtain o-chlorophenyl chloroformate, which is an intermediate of carbamate insecticides.
used in medicine, pesticides and dyes and other organic synthesis raw materials
used in medicine, pesticides and dyes and other organic synthesis raw materials
production method p-chlorophenol has various preparation methods, which can be divided into the following types according to different raw materials:
(1) phenol direct chlorination method: phenol is directly chlorinated to generate p (o, m) chlorine (benzene) phenol three isomers, which are separated to obtain p-chlorophenol. According to the difference of chlorinating agent and solvent used, it is divided into the following three methods: (a) thioyl chloride method: after heating and melting phenol, cooling to 40 ℃, slowly adding thioyl chloride, adding about 40-45min, stirring for 4h, heating to 30-40 ℃ for 4h, heating to 40-45 ℃ for 4h, absorbing the reaction tail gas with alkali solution, cooling to room temperature after reaction, washing with water, 10% sodium carbonate solution and water in turn, and distilled under reduced pressure, the 110-115 ℃(2.67kPa) fraction was collected to obtain p-chlorophenol. The method also produces 25-30% by-product o-chlorophenol. (B) Benzene solvent method: benzene is used as solvent, chlorine is used as chlorinating agent, and phenol is directly chlorinated to prepare this product. (C) Solvent-free chlorination method: using iron, bromine, etc. as catalysts, chlorine gas is passed into molten phenol, and chlorinated directly to prepare monochlorophenol. After the reaction solution is washed, it is distilled under reduced pressure to collect the fraction with p-chlorophenol content ≥ 95%.
(2) p-dichlorobenzene hydrolysis method: using p-dichlorobenzene as raw material and benzene as solvent by hydrolysis with water or alcohol.
(3) Chlorination solution mixed with o-chlorophenol and 2, 4-dichlorophenol is obtained by chlorination of sodium phenol. Decompression fractionation, collect 85-132 ℃(2.0kPa) high boiling point fraction, cool it to below 10 ℃, then p-chlorophenol is precipitated and separated.
(4) It is obtained by diazotization and copper chloride replacement of p-aminophenol.
(1) It is obtained by chlorination and acidification of sodium phenol. Stir the mixture of sodium phenol, water and ice, slowly add sodium hypochlorite solution below 20 ℃, control the temperature below 20 ℃, leave it overnight at room temperature, add concentrated hydrochloric acid under stirring to acidify to pH 2, wash once, then wash with 5% sodium carbonate solution until the pH of the washing solution is 4-5, after cooling, separate out the oil layer, carry out atmospheric fractionation, and then distill under reduced pressure to obtain the finished product. (2) Chlorination of phenol with chlorine. The molten phenol is added to benzene under stirring, and chlorine is introduced at 26±2 ℃ until the relative density of the chlorinated liquid phase reaches 0.954(23-25 ℃). After removing hydrogen chloride, the benzene is steamed out for recovery, steamed to 125 ℃(21.3kPa), cooled to 60 ℃, fractionated under reduced pressure, and collected at 75 ℃(2.67-3.33kPa) to obtain o-chlorophenol. The chlorination reaction also produces p-chlorophenol and 2, 4-dichlorophenol, which are collected as high boiling substances during vacuum fractionation and can be used as by-products after separation. The yield of o-chlorophenol (above 95%) is nearly 50%, and the yield of p-chlorophenol (above 95%) is about 25.5%.
o-chlorophenol is a co-product for the production of p-chlorophenol. chlorinated phenol is obtained by chlorination of phenol, and p-chlorophenol and o-chlorophenol can be obtained by separation.
chemical properties o-chlorophenol is a colorless to yellow-brown liquid, m.p.8.7 ℃, B. p.175 ℃,n25D 1.5565, relative density 1.265, the product is slightly soluble in water, soluble in ethanol, ether and alkali solution.
category pesticide
toxicity classification highly toxic
acute toxicity oral-rat LD50: 670 mg/kg; Oral-mouse LD50: 345 mg/kg
flammability hazard characteristics open flame combustible; high heat emits toxic chloride gas
storage and transportation characteristics warehouse ventilation and low temperature drying; Separate storage with oxidant and food additives
fire extinguishing agent mist water, foam, carbon dioxide, sand
NIST chemical substance information The information is: webbook.nist.gov provides (external link)
EPA chemical information The information is: ofmpub.epa.gov provides (external link)
spontaneous combustion temperature 550°C
toxic substance data information provided by: pubchem.ncbi.nlm.nih.gov provided (external link)
Last Update:2024-04-09 21:11:58
2-Chlorophenol
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View History
2-Chlorophenol
2-[(5-METHYL-1,3,4-THIADIAZOL-2-YL)SULFANYL]PROPANAMIDE
1-(THIEN-2-YL)BUT-1-EN-3-ONE MIXTURE OF ISOMERS
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1-Methyl-3-[(2,4,6-trinitrophenyl)azanidyl]pyridin-1-ium
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