42953-11-7

Basic information

• Product Name: ethyl N-(5-chloro-2-hydroxy-phenyl)carbamate
• Synonyms: ethyl N-(5-chloro-2-hydroxy-phenyl)carbamate
• CAS NO: 42953-11-7
• Molecular Formula: C₉H₁₀ClNO₃
• Molecular Weight: 215.63
• Mol File: 42953-11-7.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 271°Cat760mmHg
• Flash Point: 117.7°C
• Appearance: /
• Density: 1.384g/cm³
• Vapor Pressure: 0.00397mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: ethyl N-(5-chloro-2-hydroxy-phenyl)carbamate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl N-(5-chloro-2-hydroxy-phenyl)carbamate(42953-11-7)
• EPA Substance Registry System: ethyl N-(5-chloro-2-hydroxy-phenyl)carbamate(42953-11-7)

Safety Data

• Hazardous Substances Data: 42953-11-7(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H10ClNO3/c1-2-14-9(13)11-7-5-6(10)3-4-8(7)12/h3-5,12H,2H2,1H3,(H,11,13)

Upstream product

• 42953-10-6 carbonic acid ethyl ester-(2-amino-4-chloro-phenyl ester) 
• 541-41-3 chloroformic acid ethyl ester 
• 95-85-2 2-hydroxy-5-chloro-aniline 

Downstream Products

• 95-25-0 5-chloro-2-benzoxazolinone 
• 64-17-5 ethanol 
• 139930-43-1 [5-Chloro-2-(2-hydroxy-3-isopropylamino-propoxy)-phenyl]-carbamic acid ethyl ester 

Relevant articles and documents

Cyclization-Activated Prodrugs: N-(Substituted 2-hydroxyphenyl and 2-hydroxypropyl)carbamates Based on Ring-Opened Derivatives of Active Benzoxazolones and Oxazolidinones as Mutual Prodrugs of Acetaminophen

N-(Substituted 2-hydroxyphenyl)- and N-(substituted 2-hydroxypropyl)carbamates based on masked active benzoxazolones (model A) and oxazolidinones (model B), respectively, were synthesized and evaluated as potential drug delivery systems.A series of alkyl and aryl N-(5-chloro-2-hydroxyphenyl)carbamates 1 related to model A was prepared.These are open drugs of the skeletal muscle relaxant chlorzoxazone.The corresponding 4-acetamidophenyl ester named chloracetamol is a mutual prodrug of chloroxazone and acetaminophen.Chlorzacetamol and two other mutual prodrugs of active bezoxazolones and acetaminophen were obtained in a two-step process via condensation of 4-acetamidophenyl 1,2,2,2-tetrachloroethyl carbonate with the appropiate anilines.Based on model B, two mutual prodrugs of acetaminophen and active oxazolidinones (metaxalone and mephenoxalone) were similarly obtained using the appropiate amines.All the carbamate prodrugs prepared were found to release the parent drugs in aqueous (pH 6-11) and plasma (pH 7.4) media.The detailed mechanistic study of prodrugs 1 carried out in aqueous medium at 37 deg C shows a change in the Broensted-type relationship log t1/2 vs pKa of the leaving groups ROH: log t1/2 = 0.46pKa - 3.55 for aryl and trihalogenoethyl esters and log t1/2 = 1.46pKa - 16.03 for alkyl esters.This change is consistent with a cyclization mechanism involving a change in the rate-limiting step from formation of a cyclic tetrahedral intermediate (step k1) to departure of the leaving group ROH (step k2) when the leaving group ability decreases.This mechanism occurs for all the prodrugs related to model A.Regeneration of the parent drugs from mutual prodrugs related to model B takes place by means of a rate-limiting elimination-addition reaction (E1cB mechanism).This affords acetaminophen and the corresponding 2-hydroxypropyl isocyanate intermediates which cyclize at any pH to the corresponding oxazolidinone drugs.As opposed to model A, the rates of hydrolysis of mutual prodrugs of model B clearly exhibit a catalytic role of the plasma.It is concluded from the plasma studies that the carbamate substrates can be enzymatically transformed into potent electrophiles, i.e., isocyanates.In the case of the present study, the prodrugs are 2-hydroxycarbamates for which the propinquity of the hydroxyl residue and the isocyanate group enforces a cyclization reaction.This mechanistic particularity precludes their potential toxicity in terms of potent electrophiles capable of modifying critical macromolecules.