Dexbrompheniramine

Base Information

• Chemical Name: Dexbrompheniramine
• CAS No.: 132-21-8
• Molecular Formula: C₁₆H₁₉BrN₂
• Molecular Weight: 319.244
• European Community (EC) Number: 205-053-5
• UNII: 75T64B71RP
• DSSTox Substance ID: DTXSID8022905
• Wikipedia: Dexbrompheniramine
• Wikidata: Q5268318
• NCI Thesaurus Code: C61705
• RXCUI: 22696
• Pharos Ligand ID: 24AH7CACD7SV
• Metabolomics Workbench ID: 42766
• ChEMBL ID: CHEMBL1201287
• Mol file: 132-21-8.mol

Synonyms:dexbrompheniramine;dexbrompheniramine maleate;Disophrol

Chemical Property of Dexbrompheniramine

Chemical Property:

• Vapor Pressure: 1.05E-06mmHg at 25°C
• Boiling Point: 403°Cat760mmHg
• PKA: pKa 9.3 (Uncertain)
• Flash Point: 197.5°C
• PSA: 16.13000
• Density: 1.265g/cm³
• LogP: 3.92770
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 318.07316
• Heavy Atom Count: 19
• Complexity: 249

Purity/Quality:

98%min ^*data from raw suppliers

DEXBROMPHENIRAMINE 95.00% ^*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)Br)C2=CC=CC=N2
• Isomeric SMILES: CN(C)CC[C@@H](C1=CC=C(C=C1)Br)C2=CC=CC=N2
• Uses: Antihistaminic.
• Therapeutic Function: Antihistaminic

Technology Process of Dexbrompheniramine

There total 11 articles about Dexbrompheniramine 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: 75.0%

2-(4-Bromo-phenyl)-4-dimethylamino-2-pyridin-2-yl-butyronitrile (65676-22-4) → brompheniramine (86-22-6,132-21-8,32188-07-1,32656-44-3)

Guidance literature:

With potassium hydroxide; at 150 ℃; for 4h;

Reference yield: 70.0%

2-(4-Bromo-phenyl)-4-dimethylamino-butyronitrile (172274-26-9) + acetylene (74-86-2,25067-58-7) → brompheniramine (86-22-6,132-21-8,32188-07-1,32656-44-3)

Guidance literature:

(η5-cyclopentadienyl)-η4-cycloocta-1,5-dienecobalt(I); In toluene; at 140 ℃; for 36h; under 10640 Torr;

DOI:10.1021/jo00102a044

Reference yield:

(E)-3-(4-bromophenyl)-N,N-dimethylprop-2-en-1-amine → brompheniramine (86-22-6,132-21-8,32188-07-1,32656-44-3)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / HRh(CO)(PPh₃)3 / benzene / 24 h / 80 °C / 76000 Torr

2: NH₂OH

3: 96 percent / CS₂, n-Bu₄N⁽¹⁺⁾*HSO₄^(1-), 15percent aq. NaOH / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 70 percent / (η⁵-cyclopentadienyl)<(1,5-η)-cyclopentadienyl>cobalt / toluene / 36 h / 140 °C / 10640 Torr

With carbon disulfide; sodium hydroxide; hydrogen; hydroxylamine; tetra(n-butyl)ammonium hydrogensulfate; carbonylhydridetris(triphenylphosphine)rhodium(I); (η5-cyclopentadienyl)-η4-cycloocta-1,5-dienecobalt(I); In dichloromethane; toluene; benzene;

DOI:10.1021/jo00102a044

upstream raw materials:

2-(4-bromobenzyl)pyridine

2-(dimethylamino)ethyl chloride

2-(4-Bromo-phenyl)-4-dimethylamino-2-pyridin-2-yl-butyronitrile

2-(4-Bromo-phenyl)-4-dimethylamino-butyronitrile

Refernces

• 1、 Berkoff, Charles E.,Rivard, Donald E.,Kirkpatrick, David,Ives, Jeffrey L.. "THE REDUCTIVE DECYANATION OF NITRILES BY ALKALI FUSION". . p. 939 - 946. Retrieved 2007/10/02.