2-Hydroxy-5-chloroacetophenone

2-Hydroxy-5-chloroacetophenone - Names and Identifiers

Name	2'-Hydroxy-5'-chloroacetophenone
Synonyms	SALOR-INT L497495-1EA 2-Acetyl-4-chlorophenol 5-Chloro-2-hydroxyacetophenone 2-Hydroxy-5-chloroacetophenone 2'-Hydroxy-5'-chloroacetophenone 2'-Hydorxy-5'-ChloroAcetophenone 5'-Chloro-2'-hydroxyacetophenone Acetophenone,5-chloro-2-hydroxy- Acetophenone, 5'-chloro-2'-hydroxy- 1-(5-chloro-2-hydroxyphenyl)ethanone 1-(5-Chloro-2-hydroxyphenyl)ethan-1-one 5'-Chloro-2'-Hydroxy Acetophenone 2'-Hydorxy-5'-Chloro Acetophenone
CAS	1450-74-4
EINECS	215-916-8
InChI	InChI=1/C8H7ClO2/c1-5(10)7-4-6(9)2-3-8(7)11/h2-4,11H,1H3
InChIKey	XTGCUDZCCIRWHL-UHFFFAOYSA-N

2-Hydroxy-5-chloroacetophenone - Physico-chemical Properties

Molecular Formula	C8H7ClO2
Molar Mass	170.59
Density	1.2315 (rough estimate)
Melting Point	54-56°C(lit.)
Boling Point	126-128°C28mm Hg(lit.)
Flash Point	107-109°C/12mm
Vapor Presure	0.004mmHg at 25°C
Appearance	Crystalline powder
BRN	1365589
pKa	9.72±0.18(Predicted)
Storage Condition	Sealed in dry,Room Temperature
Refractive Index	1.5590 (estimate)
MDL	MFCD00067788
Physical and Chemical Properties	Almost white crystalline powder.

2-Hydroxy-5-chloroacetophenone - Risk and Safety

Hazard Symbols	Xi - Irritant
Risk Codes	36/37/38 - Irritating to eyes, respiratory system and skin.
Safety Description	S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection
WGK Germany	3
HS Code	29147000
Hazard Note	Irritant

2-Hydroxy-5-chloroacetophenone - Reference Information

NIST chemical information	Information provided by: webbook.nist.gov (external link)
Introduction	5'-chloro-2'-hydroxyacetophenone can be nitrated to prepare 5-chloro-2-hydroxy-3-nitroacetophenone. 5-Chloro-2-hydroxy-3-nitroacetophenone is a key drug intermediate for the synthesis of prenilast and has potential application value in new drug research. Prenst is the world's first leukotriene receptor antagonist pioneered by Japan's Ono Pharmaceutical Co., Ltd., which was launched in Japan in 1995. Registered in Europe and the United States in 1996. Clinically, it is mainly used as anti-asthma and anti-allergic drugs, and is an effective drug for the treatment of asthma. It was subsequently listed in Mexico in 2002 and is currently in Phase III clinical practice in the United States and the United Kingdom.
preparation	77.2g(0.6mol) of p-chlorophenol and 73.4g(0.72mol) of acetic anhydride are added to a 500mL three-mouth flask, 5g of concentrated sulfuric acid is added dropwise to the flask, stirred, reacted at 110 ℃ for 1.5h, subjected to vacuum distillation, the former fraction is glacial acetic acid, and 100g of p-chlorophenol acetate is obtained by collecting the fraction at 90 ℃, the purity is 98.2%; 34.2g(0.2mol) of p-chlorophenol acetate is added to a 500mL three-mouth flask, 79.5g (about 0.6mol) of anhydrous aluminum trichloride is slowly added to the flask and stirred for 1h at 130 ℃. After the reaction, 200mL of water is slowly added to the flask, stirred for 0.5h, filtered, the filter cake is heated and dissolved with methanol, activated carbon is decolorized and recrystallized, 30.8g of 5-chloro-2-hydroxyacetophenone was obtained with a purity of 99.68%.

Last Update：2024-04-09 02:00:07

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