5560-77-0

Basic information

• Product Name: Rotoxamine
• Synonyms: Rotoxamine;Levocarbinoxamine;McN-R-73-Z;2-[(S)-(4-chlorophenyl)-(2-pyridyl)methoxy]ethyl-dimethyl-amine;2-[(S)-(4-chlorophenyl)-pyridin-2-yl-methoxy]-N,N-dimethyl-ethanamine;2-[(S)-(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine;(S)-carbinoxamine
• CAS NO: 5560-77-0
• Molecular Formula: C₁₆H₁₉ClN₂O
• Molecular Weight: 290.792
• Mol File: 5560-77-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 381.1°Cat760mmHg
• Flash Point: 184.3°C
• Appearance: /
• Density: 1.143g/cm³
• Vapor Pressure: 5.21E-06mmHg at 25°C
• Refractive Index: 1.562
• PKA: 8.65±0.28(Predicted)
• CAS DataBase Reference: Rotoxamine(CAS DataBase Reference)
• NIST Chemistry Reference: Rotoxamine(5560-77-0)
• EPA Substance Registry System: Rotoxamine(5560-77-0)

Safety Data

• Hazardous Substances Data: 5560-77-0(Hazardous Substances Data)

Usage

Uses

Antihistaminic.

Definition

ChEBI: The (S)- (active) enantiomer of carbinoxamine.

Brand name

Twiston (Ortho-McNeil); Twiston RA (Ortho-McNeil).

InChI:InChI=1/C16H19ClN2O/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13/h3-10,16H,11-12H2,1-2H3/t16-/m0/s1

Upstream product

• 486-16-8 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine 
• 1563017-46-8 (4-chlorophenyl)(1-oxido-2-pyridinyl)methanone 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 176022-47-2 (S)-(+)-(4-chlorophenyl)-(2-pyridyl)methanol 
• 873-77-8 (4-chlorphenyl)magnesium bromide 
• 6318-51-0 2-(4-chlorobenzoyl)pyridine 
• 100-70-9 2-Cyanopyridine 
• 182009-51-4 2-[(S)-(4-Chloro-phenyl)-pyridin-2-yl-methoxy]-N,N-dimethyl-acetamide 

Relevant articles and documents

Evaluation of the Edman degradation product of vancomycin bonded to core-shell particles as a new HPLC chiral stationary phase

A modified macrocyclic glycopeptide-based chiral stationary phase (CSP), prepared via Edman degradation of vancomycin, was evaluated as a chiral selector for the first time. Its applicability was compared with other macrocyclic glycopeptide-based CSPs: TeicoShell and VancoShell. In addition, another modified macrocyclic glycopeptide-based CSP, NicoShell, was further examined. Initial evaluation was focused on the complementary behavior with these glycopeptides. A screening procedure was used based on previous work for the enantiomeric separation of 50 chiral compounds including amino acids, pesticides, stimulants, and a variety of pharmaceuticals. Fast and efficient chiral separations resulted by using superficially porous (core-shell) particle supports. Overall, the vancomycin Edman degradation product (EDP) resembled TeicoShell with high enantioselectivity for acidic compounds in the polar ionic mode. The simultaneous enantiomeric separation of 5 racemic profens using liquid chromatography-mass spectrometry with EDP was performed in approximately 3?minutes. Other highlights include simultaneous liquid chromatography separations of rac-amphetamine and rac-methamphetamine with VancoShell, rac-pseudoephedrine and rac-ephedrine with NicoShell, and rac-dichlorprop and rac-haloxyfop with TeicoShell.

Asymmetric synthesis of (S)-carbinoxamine. New aspects of oxazaborolidine-catalyzed enantioselective carbonyl reduction

A new process has been developed for the highly enantioselective catalytic reduction of 2-aroylpyridines and successfully applied to the synthesis of (S)-carbinoxamine (1), a therapeutically important histamine H1 antagonist. Related enantioselective reductions of 4-aroylpyridines and ortho-substituted benzophenones are also described.