2-Chloro-4-hydroxybenzonitrile

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2-Chloro-4-hydroxybenzonitrile Basic information
Uses
Product Name:2-Chloro-4-hydroxybenzonitrile
Synonyms:Chloro-4-hydroxybenzonitrile;Benzonitrile,2-chloro-4-hydroxy-;2-Chloro-4-hydroxybenzonitrile 98+%;3-Chloro-4-cyanophenol;2-Chloro-4-hydroxybenzonitrile 98%;2-Chloro-4-hydroxybenzonitrile
CAS:3336-16-1
MF:C7H4ClNO
MW:153.57
EINECS:
Product Categories:Aromatic Nitriles;C6 to C7;Cyanides/Nitriles;Nitrogen Compounds
Mol File:3336-16-1.mol
2-Chloro-4-hydroxybenzonitrile Structure
2-Chloro-4-hydroxybenzonitrile Chemical Properties
Melting point 160 °C (dec.)(lit.)
Boiling point 323.2±27.0 °C(Predicted)
density 1.41±0.1 g/cm3(Predicted)
storage temp. Inert atmosphere,Room Temperature
pka6.88±0.18(Predicted)
form powder
color White
InChI1S/C7H4ClNO/c8-7-3-6(10)2-1-5(7)4-9/h1-3,10H
InChIKeyBDDVAWDNVWLHDQ-UHFFFAOYSA-N
SMILESOc1ccc(C#N)c(Cl)c1
CAS DataBase Reference3336-16-1
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-37/39
WGK Germany 3
HS Code 2926907090
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
MSDS Information
ProviderLanguage
SigmaAldrich English
2-Chloro-4-hydroxybenzonitrile Usage And Synthesis
Uses2-Chloro-4-hydroxybenzonitrile is used for preparation of arylthioamides.
Chemical Propertieswhite to light yellow crystal powder
Uses2-Chloro-4-hydroxybenzonitrile may be used in the synthesis of 6-aminophenanthridines via Suzuki-Miyaura coupling reaction. It may be used in the preparation of 5-bromo-2-chloro-4-hydroxybenzonitrile.
Synthesis
4-Amino-2-chlorobenzonitrile

20925-27-3

2-CHLORO-4-HYDROXYBENZONITRILE

3336-16-1

Step 5: 2-Chloro-4-aminobenzonitrile (25 g, 0.187 mol) was added to a stirred mixture of concentrated sulfuric acid (58 g) and water (570 mL) and heated between 49 °C and 61 °C for about 30 minutes. The suspension was cooled to about 0°C and a cold solution of sodium nitrite (13.2 g, 0.187 mol) dissolved in water (125 mL) was slowly added dropwise over a temperature range of 0°C to 6°C. After the dropwise addition was completed, stirring of the reaction mixture was continued for about 3 hours. Subsequently, urea (1.5 g) was added to the mixture to quench the excess sodium nitrite. Insoluble impurities were removed by filtration. To the filtrate was added a 50% aqueous sulfuric acid solution (600 mL) while the reaction mixture was heated to between 74 °C and 81 °C with continuous stirring until the nitrogen stopped escaping. Upon completion of the reaction, the product was separated by filtration and purified with recrystallized water to give 2-chloro-4-hydroxybenzonitrile (17.9 g, 62.5% yield, melting point 160 °C).

References[1] Patent: US4424371, 1984, A
2-Chloro-4-hydroxybenzonitrile Preparation Products And Raw materials
Raw materials4-Amino-2-chlorobenzonitrile-->Urea-->Water-->Sodium nitrite-->Sulfuric acid
Preparation Products2-Chloro-4-hydroxy-benzoic acid methyl ester-->4-Benzyloxy-3-chloro-benzonitrile-->Ethyl 2-chloro-4-hydroxybenzoate
Tag:2-Chloro-4-hydroxybenzonitrile(3336-16-1) Related Product Information
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