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

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

Used in Pharmaceutical Industry:
Carbinoxamine is used as an antihistaminic agent for treating allergic symptoms such as hay fever. It works by blocking the action of histamine, a substance released during an allergic reaction, which helps alleviate symptoms like itching, sneezing, and runny nose.
Additionally, carbinoxamine is used as a treatment for mild cases of Parkinson's disease. It is believed to provide relief from some of the symptoms associated with the condition, although the exact mechanism of action in this context is not as well understood as its antihistamine properties.

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

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

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.

The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine

An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents are excellent nucleophilic counterparts in this reaction, generating carbinols in excellent yields (61-94%). The formation of triarylmethanes is also witnessed in the case of certain reactive aldehydes and aromatic π-nucleophiles through reactive carbocation formation. The formation of triarylmethane is reduced to a greater extent via retardation of the second π-nucleophile addition through a Lewis base, for example, pyridine, coordination with an aluminium alkoxide intermediate. Various aliphatic aldehydes also underwent Friedel-Crafts type hydroxyalkylation and generated the expected carbinols in moderate yields (41-53%) in the presence of AlBr3. This protocol has been successfully applied to the synthesize of the (±)-carbinoxamine, a therapeutically important histamine H1 antagonist, in a one-pot manner.

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.

Highly selective metalations of pyridines and related heterocycles using new frustrated lewis pairs or tmp-zinc and tmp-magnesium bases with bf 3·oet2

(Figure Presented) Efficient and selective: Frustrated Lewis pairs based on BF3·OEt2 and LiCl-com-plexed tmpMg or tmpZn amides (tmp = 2,2,6,6-tetramethylpiperidyl) allow the efficient and regioselective metalation of various functionalized N heterocycles (see scheme for examples). Moreover, such metalations carried out in the presence or absence of BF 3·OEt2 enable a complete switch of regioselectivity, thus allowing complementary fuctionalization.

[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.