Carbinoxamine

Base Information

• Chemical Name: Carbinoxamine
• CAS No.: 486-16-8
• Deprecated CAS: 59811-38-0
• Molecular Formula: C16H19 Cl N2 O
• Molecular Weight: 290.793
• Hs Code.: 2933399090
• European Community (EC) Number: 207-628-6
• UNII: 982A7M02H5
• DSSTox Substance ID: DTXSID4022737
• Nikkaji Number: J6.006B,J7.994D
• Wikipedia: Carbinoxamine
• Wikidata: Q3728177
• NCI Thesaurus Code: C65286
• RXCUI: 20220
• Pharos Ligand ID: A1ZB7PB8KK7U
• Metabolomics Workbench ID: 145482
• ChEMBL ID: CHEMBL864
• Mol file: 486-16-8.mol

Synonyms:carbinoxamine;carbinoxamine maleate;Histex CT;Histex I-E;Histex PD

Chemical Property of Carbinoxamine

Chemical Property:

• Boiling Point: 381.1°Cat760mmHg
• PKA: pKa 8.1 (Uncertain)
• Flash Point: 184.3°C
• PSA: 25.36000
• Density: 1.143g/cm³
• LogP: 3.40260
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 290.1185909
• Heavy Atom Count: 20
• Complexity: 267

Purity/Quality:

99% ^*data from raw suppliers

2-((4-Chlorophenyl)(pyridin-2-yl)methoxy)-N,N-dimethylethanamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antihistamines
• Canonical SMILES: CN(C)CCOC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
• Uses: Antihistaminic.

Technology Process of Carbinoxamine

There total 6 articles about Carbinoxamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.0%

carbinoxamine N-oxide (1256285-70-7) → 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine (486-16-8)

Guidance literature:

With sodium tetrahydroborate; In water; at 50 - 60 ℃; chemoselective reaction;

DOI:10.1016/j.tetlet.2010.08.045

Reference yield: 80.0%

(4-chlorophenyl)-2-pyridylmethanol (27652-89-7) + 2-(dimethylamino)ethyl chloride (107-99-3) → 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine (486-16-8)

Guidance literature:

With sodium t-butanolate; In toluene; for 6h; Reflux;

DOI:10.1021/acs.orglett.0c03108

Reference yield: 72.0%

pyridine (110-86-1) + (2-chloroethyl)dimethylamine hydrochloride (4584-46-7) + 4-chlorobenzaldehyde (104-88-1) → 2-[(4-chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine (486-16-8)

Guidance literature:

pyridine; With 2,2,6,6-tetramethylpiperidinylmagnesium chloride lithium chloride complex; boron trifluoride diethyl etherate; In tetrahydrofuran; at -40 ℃; Inert atmosphere;

4-chlorobenzaldehyde; In tetrahydrofuran; at -40 - 25 ℃; Inert atmosphere;

(2-chloroethyl)dimethylamine hydrochloride; With sodium hydride; sodium iodide; In tetrahydrofuran; mineral oil; at 25 - 50 ℃; regioselective reaction; Neat (no solvent); Inert atmosphere;

DOI:10.1002/anie.201002031

upstream raw materials:

2-(dimethylamino)ethyl chloride

(4-chlorophenyl)-2-pyridylmethanol

(2-chloroethyl)dimethylamine hydrochloride

pyridine

Downstream raw materials:

carbinoxamine N-oxide

(S)-carbinoxamine

2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]-N,N-dimethylethanamine

Refernces

• 1、 Harikrishnan, Adhikesavan,Sanjeevi, Jayakumar,Ramanathan, Chinnasamy Ramaraj. "The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: A simple and effective route for the synthesis of (±)-carbinoxamine". . p. 3633 - 3647. Retrieved 2015/03/30.
• 2、 Gowda, Narendra B.,Rao, Gopal Krishna,Ramakrishna, Ramesha A.. "A chemoselective deoxygenation of N-oxides by sodium borohydride-Raney nickel in water". experimental part. p. 5690 - 5693. Retrieved 2010/11/05.