56707-26-7

Basic information

• Product Name: mabuterol
• Synonyms: Benzenemethanol, 4-amino-3-chloro-α-[[(1,1-dimethylethyl)amino]methyl]-5-(trifluoromethyl)-, (αR)-
• CAS NO: 56707-26-7
• Molecular Formula: C13H18ClF3N2O
• Molecular Weight: 310.7430296
• Mol File: 56707-26-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: mabuterol(CAS DataBase Reference)
• NIST Chemistry Reference: mabuterol(56707-26-7)
• EPA Substance Registry System: mabuterol(56707-26-7)

Safety Data

• Hazardous Substances Data: 56707-26-7(Hazardous Substances Data)

Upstream product

• 56341-08-3 mabuterol 
• 97760-87-7 1-[4-Amino-3-chloro-5-(trifluoromethyl)phenyl]-2-bromoethanone 
• 97760-76-4 4'-amino-3'-chloro-5'-trifluoromethyl-acetophenone 
• 97760-88-8 4'-amino-3'-chloro-5'-trifluoromethyl-2-tert.-butylamino-acetophenone 
• 67-56-1 methanol 

Downstream Products

• 56707-24-5 d-1-(4-amino-3-chloro-5-trifluoromethyl-phenyl)-2-tert.-butylamino-ethanol 
• 56707-24-5 (S)-mabuterol 
• 56707-24-5 (R)-mabuterol 

Relevant articles and documents

Effect of basic and acidic additives on the separation of some basic drug enantiomers on polysaccharide-based chiral columns with acetonitrile as mobile phase

The separation of enantiomers of 16 basic drugs was studied using polysaccharide-based chiral selectors and acetonitrile as mobile phase with emphasis on the role of basic and acidic additives on the separation and elution order of enantiomers. Out of the studied chiral selectors, amylose phenylcarbamate-based ones more often showed a chiral recognition ability compared to cellulose phenylcarbamate derivatives. An interesting effect was observed with formic acid as additive on enantiomer resolution and enantiomer elution order for some basic drugs. Thus, for instance, the enantioseparation of several β-blockers (atenolol, sotalol, toliprolol) improved not only by the addition of a more conventional basic additive to the mobile phase, but also by the addition of an acidic additive. Moreover, an opposite elution order of enantiomers was observed depending on the nature of the additive (basic or acidic) in the mobile phase.

Synthesis of further amino-halogen-substituted phenyl-aminoethanols

Starting from clenbuterol as a lead structure, new 4-amino-phenyl-aminoethanol analogues have been synthesized by different approaches. In these compounds one or both of the chlorine atoms of clenbuterol are replaced by other residues. This has led to compounds with high intrinsic β2-mimetic and/or β1-blocking activities. 1-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-2-tert.-butylamino-ethanol hydrochloride (mabuterol) has been selected for clinical development. A detailed description is also given of the syntheses of new intermediate acetophenone derivatives as well as of the resolution of mabuterol into its enantiomers.

BRONCHOSPASMOLYTIC 1-(P-AMINO-PHENYL)-2-AMINO-ETHANOLS-(1) AND SALTS

Racemic and optically active compounds of the formula wherein R1 is hydrogen, fluorine, chlorine, bromine, iodine or cyano, R2 is fluorine, trifluoromethyl, nitro or cyano, and R3 is alkyl of 3 to 5 carbon atoms, hydroxy(alkyl of 3 to 5 carbon atoms), cycloalkyl of 3 to 5 carbon atoms, 1-(3,4-methylenedioxy-phenyl)-2-propyl or 1-(p-hydroxy-phenyl)-2-propyl, and non-toxic, pharmacologically acceptable acid addition salts thereof; the compounds as well as their salts are useful as analgesics, uterospasmolytics, bronchospasmolytics and antispastics for the skeletal musculature, and especially as beta 2-receptor mimetics and beta 1-receptor blockers