22471-02-9

Basic information

• Product Name: Benzenemethanol, 3-chloro-2-hydroxy-
• Synonyms: Benzenemethanol, 3-chloro-2-hydroxy-
• CAS NO: 22471-02-9
• Molecular Formula: C₇H₇ClO₂
• Molecular Weight: 158.58
• Mol File: 22471-02-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Benzenemethanol, 3-chloro-2-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenemethanol, 3-chloro-2-hydroxy-(22471-02-9)
• EPA Substance Registry System: Benzenemethanol, 3-chloro-2-hydroxy-(22471-02-9)

Safety Data

• Hazardous Substances Data: 22471-02-9(Hazardous Substances Data)

Usage

General Description

3-Chloro-2-hydroxybenzenemethanol, also known as chlorzoxazone, is a chemical compound used as a muscle relaxant and mild analgesic. It works by inhibiting the release of certain neurotransmitters in the brain and spinal cord, leading to muscle relaxation. Chlorzoxazone is commonly prescribed for the treatment of musculoskeletal pain and discomfort caused by injuries or other conditions. It is usually taken orally and has a relatively low risk of addiction or abuse compared to other muscle relaxants. However, it may cause drowsiness and dizziness, so caution should be exercised when operating heavy machinery or driving while taking this medication.

Upstream product

• 50-00-0 formaldehyd 
• 95-57-8 2-monochlorophenol 
• 1927-94-2 3-chlorosalicylaldehyde 
• 412304-64-4 2-chloro-6-hydroxymethyl-benzenesulfonyl chloride 

Downstream Products

• 173173-55-2 3',3-dichloro-4',4-dihydroxy-5',5-bis(hydroxymethyl)-1,1-diphenylmethane 
• 1927-94-2 3-chlorosalicylaldehyde 
• 65685-40-7 3-chlorosalicylaldoximine 
• 67810-64-4 3-chloro-2-hydroxy-benzaldehyde-semicarbazone 

Relevant articles and documents

A new biological prospective for the 2-phenylbenzofurans as inhibitors of α-glucosidase and of the islet amyloid polypeptide formation

In this study, we have investigated a series of hydroxylated 2-phenylbenzofurans compounds for their inhibitory activity against α-amylase and α-glucosidase activity. Inhibitors of carbohydrate degrading enzymes seem to have an important role as antidiabetic drugs. Diabetes mellitus is a wide-spread metabolic disease characterized by elevated levels of blood glucose. The most common is type 2 diabetes, which can lead to severe complications. Since the aggregates of islet amyloid polypeptide (IAPP) are common in diabetic patients, the effect of compounds to inhibit amyloid fibril formation was also determined. All the compounds assayed showed to be more active against α-glucosidase. Compound 16 showed the lowest IC50 value of the series, and it is found to be 167 times more active than acarbose, the reference compound. The enzymatic activity assays showed that compound 16 acts as a mixed-type inhibitor of α-glucosidase. Furthermore, compound 16 displayed effective inhibition of IAPP aggregation and it manifested no significant cytotoxicity. To predict the binding of compound 16 to IAPP and α-glucosidase protein complexes, molecular docking studies were performed. Altogether, our results support that the 2-phenylbenzofuran derivatives could represent a promising candidate for developing molecules able to modulate multiple targets involved in diabetes mellitus disorder.

Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol-Derived Chlorohydrosilane

A newly developed stable chlorohydrosilane derived from pinacol is herein described. This was successfully used in the reduction of salicylaldehydes in reasonable to excellent yields (51–97 %). The ability of the hydrosilane to react as a reducing agent is increased upon the in situ formation of a trialkoxyhydrosilane and activation with a Lewis base, as further indicated by density functional theory studies. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) was identified to be a suitable catalyst for this metal-free reduction, promoting the regio- and chemoselective reduction of aldehydes in ortho-position to phenols, despite the presence of vicinal ketones. The performance of pinacol-derived chlorohydrosilane in the reduction of salicylaldehydes was further observed to be superior to that of well-established commercially available chlorohydrosilanes.