Brompheniramine

Base Information

• Chemical Name: Brompheniramine
• CAS No.: 86-22-6
• Deprecated CAS: 156428-33-0,32188-07-1,32188-07-1
• Molecular Formula: C₁₆H₁₉BrN₂
• Molecular Weight: 319.244
• European Community (EC) Number: 201-657-8
• UNII: H57G17P2FN
• DSSTox Substance ID: DTXSID5022691
• Nikkaji Number: J4.936K,J5.569G,J554.571D
• Wikipedia: Brompheniramine
• Wikidata: Q2606497
• NCI Thesaurus Code: C61655
• RXCUI: 1767
• Pharos Ligand ID: 24ARYZW668CL
• Metabolomics Workbench ID: 143505
• ChEMBL ID: CHEMBL811
• Mol file: 86-22-6.mol

Synonyms:Brompheniramine;Brompheniramine Maleate;Brompheniramine Maleate (1:1);Chlorphed;Dimetane;Dimetane Ten;Dimetane-Ten;Dimetapp Allergy;Maleate, Brompheniramine;Oraminic 2;Oraminic-2;p Bromdylamine;p-Bromdylamine;para Bromdylamine;para-Bromdylamine

Chemical Property of Brompheniramine

Chemical Property:

• Appearance/Colour: Oily liquid with slightly yellow color. Characteristic amine-like.
• Vapor Pressure: 1.05E-06mmHg at 25°C
• Melting Point: 25°C
• Refractive Index: 1.5770 (estimate)
• Boiling Point: 403 °C at 760 mmHg
• PKA: pKa 3.59 (Uncertain)
• Flash Point: 197.5 °C
• PSA: 16.13000
• Density: 1.265 g/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:

99% ^*data from raw suppliers

Brompheniramine ^*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
• Recent ClinicalTrials: Efficacy and Safety of Combination of Brompheniramine and Phenylephrine for the Symptoms Relief of Rhinitis
• Uses: antidepressant Brompheniramine is also used for allergy symptoms, rhinitis, and dermatitis. Its activity is approximately the same as that of chlorpheniramine. Synonyms of this drug are dimetane, brombey, spentan, veltane, and others.

Technology Process of Brompheniramine

There total 11 articles about Brompheniramine 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.