486-16-8

Basic information

• Product Name: carbinoxamine
• Synonyms: 2-[(4-CHLOROPHENYL)-2-PYRIDINYLMETHOXY]-N,N-DIMETHYLETHANAMINE;2-[p-chloro-a-(2-dimethylaminoethoxy)benzyl]pyridine;paracarbinoxamine;Carbinoxamine (base and/or unspecified salts);2-[p-Chloro-α-(2-dimethylaminoethoxy)benzyl]pyridine;2-[p-Chloro-α-[2-(dimethylamino)ethoxy]benzyl]pyridine;2-{[(4-Chlorophenyl)(pyridin-2-yl)methyl]oxy}-N,N-dimethylethanamine;C06871
• CAS NO: 486-16-8
• Molecular Formula: C₁₆H₁₉ClN₂O
• Molecular Weight: 290.78786
• EINECS: 207-628-6
• Mol File: 486-16-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: bp0.1 158-162°
• Flash Point: 184.3°C
• Appearance: /
• Density: 1.143g/cm³
• PKA: pKa 8.1 (Uncertain)
• CAS DataBase Reference: carbinoxamine(CAS DataBase Reference)
• NIST Chemistry Reference: carbinoxamine(486-16-8)
• EPA Substance Registry System: carbinoxamine(486-16-8)

Safety Data

• Hazardous Substances Data: 486-16-8(Hazardous Substances Data)

Usage

Uses

Antihistaminic.

Definition

ChEBI: An organochlorine compound that is 2-(4-chlorobenzyl)pyridine in which one of the benzylic hydrogens is substituted by 2-(dimethylamino)ethoxy group. It is an ethanolamine-type antihistamine, used as its maleate salt for treating hay fever, as well as mild cases of Parkinson's disease.

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

Upstream product

• 110-86-1 pyridine 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 104-88-1 4-chlorobenzaldehyde 
• 27652-89-7 (4-chlorophenyl)-2-pyridylmethanol 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 1121-60-4 pyridine-2-carbaldehyde 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 108-90-7 chlorobenzene 
• 1256285-70-7 carbinoxamine N-oxide 

Downstream Products

• 1256285-70-7 carbinoxamine N-oxide 
• 5560-77-0 (S)-carbinoxamine 
• 59811-40-4 2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]-N,N-dimethylethanamine 

Relevant articles and documents

Transition-Metal Free Chemoselective Hydroxylation and Hydroxylation-Deuteration of Heterobenzylic Methylenes

We developed an approach for direct selective hydroxylation of heterobenzylic methylenes to secondary alcohols avoiding overoxidation to ketones by using a KOBu-t/DMSO/air system. Most reactions could reach completion in several minutes to give hydroxylated products in 41-76% yields. Using DMSO-d6, this protocol resulted in difunctionalization of heterobenzylic methylenes to afford α-deuterated secondary alcohols (>93% incorporation). By employing this method, active pharmaceutical ingredients carbinoxamine and doxylamine were synthesized in two steps in moderate yields.

A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water

A simple and convenient protocol for deoxygenation of aliphatic and aromatic N-oxides to the corresponding amines in good to excellent yield using sodium borohydride-Raney nickel in water is reported. Other functional moieties such as alkenes, halides, ethers, and amides are unaffected under the present reaction condition.

[1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers

(Chemical Equation Presented) An anionic rearrangement of 2-benzyloxypyridine is described. Pyridine-directed metalation of the benzylic carbon leads to 1,2-migration of pyridine via a postulated associative mechanism (addition/elimination). Several aryl pyridyl carbinols were obtained in high yields. A formal synthesis of carbinoxamine, an antihistamine drug used for the treatment of seasonal allergies and hay fever, emerges from this methodology.