111477-47-5

Basic information

• Product Name: 7-chloro-6-fluoro-4-hydroxy-2-methylchroman-4-acetic acid
• Synonyms: 7-chloro-6-fluoro-4-hydroxy-2-methylchroman-4-acetic acid
• CAS NO: 111477-47-5
• Molecular Formula: C12H12 Cl F O4
• Molecular Weight: 274.67
• Mol File: 111477-47-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 374.1°Cat760mmHg
• Flash Point: 180°C
• Appearance: /
• Density: 1.359g/cm³
• Vapor Pressure: 2.93E-06mmHg at 25°C
• Refractive Index: 1.528
• CAS DataBase Reference: 7-chloro-6-fluoro-4-hydroxy-2-methylchroman-4-acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-6-fluoro-4-hydroxy-2-methylchroman-4-acetic acid(111477-47-5)
• EPA Substance Registry System: 7-chloro-6-fluoro-4-hydroxy-2-methylchroman-4-acetic acid(111477-47-5)

Safety Data

• Hazardous Substances Data: 111477-47-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C12H12ClFO4/c1-6-2-7(3-12(15)18-16)8-4-10(14)9(13)5-11(8)17-6/h4-7,16H,2-3H2,1H3/t6-,7-/m1/s1

Upstream product

• 2613-23-2 3-chloro-4-fluorophenol 
• 111477-46-4 ethyl 7-chloro-6-fluoro-c-4-hydroxy-2(R)-methylchroman-4-acetate 
• 112711-08-7 ((2R,4R)-7-Chloro-6-fluoro-4-hydroxy-2-methyl-chroman-4-yl)-acetic acid 
• 111478-28-5 3-(3-chloro-4-fluorophenoxy)butyric acid 
• 111503-55-0 ethyl (R)-2-(3-chloro-4-fluorophenoxy)propionate 
• 111503-60-7 7-chloro-6-fluoro-2(R)-methylchroman-4-one 
• 111478-29-6 7-chloro-6-fluoro-2-methylchroman-4-one 
• 111503-57-2 (R)-2-(3-chloro-4-fluorophenoxy)propyl bromide 
• 140226-50-2 (R)-2-(3-chloro-4-fluorophenoxy)propanol 
• 111532-20-8 4-(benzoylamino)-7-chloro-6-fluoro-2(R)-methylchroman-4-carboxylic acid 
• 111503-24-3 2-(benzoylamino)-2-<2-<(1R)-2-bromo-1-methylethoxy>-4-chloro-5-fluorophenyl>acetic acid 
• 140226-51-3 N-(7-chloro-6-fluoro-2(R)-methylchroman-4-yl)benzamide 
• 111477-46-4 ((2R,4R)-7-Chloro-6-fluoro-4-hydroxy-2-methyl-chroman-4-yl)-acetic acid ethyl ester 

Relevant articles and documents

Hydantoin Bioisosteres. In Vivo Active Hydroxy Acetic Acid Aldose Reductase Inhibitors

The hypothesis that clinical side effects of the aldose reductase inhibitor (ARI) sorbinil were related to its hydantoin ring led to a bioisosteric analysis and replacement of the hydantoin by a spiro hydroxy acetic acid moiety as in 40.These hydroxy acids, compared to hydantoins, showed a similar potency increase on chroman 2-methyl substitution, a similar orthogonal relationship of acidic to aromatic moieties, and similar ARI enantioselectivity.In this series the six-membered spiro hydroxy acetic acid anion array is a bioisostere for a spiro hydantoin anion and leads to ARIs with excellent in vivo activity.In vitro and in vivo activity was improved over 40 by chroman cis 2-methylation as in 4 and by aromatic 6,7-halogen substitution.Compounds with the best acute in vivo activity in rats were compared for chronic in vivo activity.The highest tissue levels and best chronic in vivo activities were found in the racemic 6,7-dichloro and 6-fluoro-7-chloro analogues 18 and 23.ARI activity was enantioselective for 58 and 60, the 2R,4R-enantiomers of 18 and 23. 7-Chloro-6-fluoro-cis-4-hydroxy-2(R)-methyl-chroman-4-acetic acid (60) was selected for phase 1 clinical trials and did not exhibit sorbinil-like hypersensitivity side effects.

Hydroxyacetic acid derivatives for the treatment of diabetic complications

Racemic and chiral (2R,4R)-4-c-hydroxy-2-4-(substituted)chroman(and thiochroman)-4-acetic acids and their pharmaceutically acceptable salts, their use in the treatment of diabetic complications and intermediates therefor.