(-)-Chlorpheniramine

Base Information

• Chemical Name: (-)-Chlorpheniramine
• CAS No.: 32188-09-3
• Molecular Formula: C16H19ClN2
• Molecular Weight: 274.793
• European Community (EC) Number: 926-835-9,636-521-0
• UNII: EY9131E63D
• DSSTox Substance ID: DTXSID00904610
• Wikidata: Q27075977
• Metabolomics Workbench ID: 58031
• ChEMBL ID: CHEMBL1554789
• Mol file: 32188-09-3.mol

Synonyms:(-)-chlorpheniramine;(-)-Chloropheniramine;Chlorphenamine, (R)-;Chlorpheniramine, (R)-;Chlorpheniramine, (-)-;l-chlorpheniramine;levochlorpheniramine;32188-09-3;UNII-EY9131E63D;CHEBI:52013;(3R)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine;EY9131E63D;[(3R)-3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine;(gammaR)-gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamine;2-Pyridinepropanamine, gamma-(4-chlorophenyl)-N,N-dimethyl-, (R)-;Pyridine, 2-(p-chloro-alpha-(2-(dimethylamino)ethyl)benzyl)-, (-)-;2-Pyridinepropanamine, gamma-(4-chlorophenyl)-N,N-dimethyl-, (gammaR)-;Spectrum_000140;Spectrum2_000156;Spectrum3_000345;Spectrum4_000282;Spectrum5_001442;Lopac-C-3025;Lopac-C-4915;CAS-113-92-8;SCHEMBL4220;BSPBio_002009;KBioGR_000804;KBioSS_000600;SPBio_000292;GTPL1213;dexchlorpheniramine, (R)-isomer;CHEMBL1554789;KBio2_000600;KBio2_003168;KBio2_005736;KBio3_001229;DTXSID00904610;NCGC00015227-01;NCGC00015227-02;NCGC00016364-01;NCGC00016364-02;NCGC00016364-03;SBI-0051311.P003;LS-174369;BRD-K89595132-050-02-2;BRD-K89595132-050-03-0;Q27075977;(.GAMMA.R)-.GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-2-PYRIDINEPROPANAMINE;2-PYRIDINEPROPANAMINE, .GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-, (.GAMMA.R)-;2-PYRIDINEPROPANAMINE, .GAMMA.-(4-CHLOROPHENYL)-N,N-DIMETHYL-, (R)-;PYRIDINE, 2-(P-CHLORO-.ALPHA.-(2-(DIMETHYLAMINO)ETHYL)BENZYL)-, (-)-

Chemical Property of (-)-Chlorpheniramine

Chemical Property:

• PSA: 16.13000
• LogP: 3.81860
• XLogP3: 3.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 274.1236763
• Heavy Atom Count: 19
• Complexity: 249

Purity/Quality:

(R)-Chloropheniramine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
• Isomeric SMILES: CN(C)CC[C@H](C1=CC=C(C=C1)Cl)C2=CC=CC=N2
• Uses: (R)-Chloropheniramine is an intermediate used in the synthesis of (R)-(-)-Chlorpheniramine Maleate (C424306), which is the R-enantiomer of Chlorpheniramine (C424300). Antihistaminic.

Technology Process of (-)-Chlorpheniramine

There total 2 articles about (-)-Chlorpheniramine 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:

Chlorpheniramine (132-22-9) → dexchlorpheniramine (25523-97-1) + L-chlorpheniramine (32188-09-3)

Guidance literature:

With chiral stationary phase derived from aminated silica gel, L-2-(p-toluenesulfonamido)-3-phenylpropionyl chloride and dendrimer; In water; acetonitrile; at 25 ℃; Resolution of racemate;

DOI:10.1002/chir.20708

Reference yield:

Chlorpheniramine (132-22-9) → L-chlorpheniramine (32188-09-3)

Guidance literature:

With C₁₈H₁₈O₆;

DOI:10.1038/183734a0

upstream raw materials:

Chlorpheniramine

Refernces

• 1、 He, Bao-Jiang,Yin, Chuan-Qi,Li, Shi-Rong,Bai, Zheng-Wu. "Synthesis of dendrimer-type chiral stationary phases based on the selector of (1S,2R)-(+)-2-amino-1,2-diphenylethanol derivate and their enantioseparation evaluation by HPLC". experimental part. p. 69 - 76. Retrieved 2010/09/09.