Bromantane

Base Information

• Chemical Name: Bromantane
• CAS No.: 87913-26-6
• Deprecated CAS: 138308-72-2
• Molecular Formula: C16H20BrN
• Molecular Weight: 306.245
• European Community (EC) Number: 687-739-8
• UNII: N1ILS53XWK
• ChEMBL ID: CHEMBL4303520
• DSSTox Substance ID: DTXSID40405333
• Nikkaji Number: J1.013.532J
• Wikidata: Q385533
• Wikipedia: Bromantane
• Mol file: 87913-26-6.mol

Synonyms:2-bromophenyl-1-amino adamantane;bromantane;bromontan

Chemical Property of Bromantane

Chemical Property:

• Boiling Point: 404.8 °C at 760 mmHg
• PKA: 3.97±0.20(Predicted)
• Flash Point: 198.6 °C
• PSA: 12.03000
• Density: 1.388 g/cm³
• LogP: 4.75870
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 2
• Exact Mass: 305.07791
• Heavy Atom Count: 18
• Complexity: 280

Purity/Quality:

99%, ^*data from raw suppliers

Bromantane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)C3NC4=CC=C(C=C4)Br
• Description: Bromantane is an adamantine derivate that has a bromaniline side chain. It has been used therapeutically in Russia as a psychostimulant and anxiolytic. It have serotonergic, dopaminergic and limited noradrenergic actions，similar tomesocarb. Bromantane was first detected in 1996(Ayotte and Goudreault 1999), but due to juridical problems nine doping cases at the Atlanta Olympic Games were classified without consequences for the athletes. It was included in the IOC list of prohibited substances in September 1996，shortly after the Olympic Games.
• Uses: N-(2-ADAMANTYL)-N-(4-BROMOPHENYL)AMINE is an adamantane derivative used as an anxiolytic agent.

Technology Process of Bromantane

There total 2 articles about Bromantane 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: 90.0%

2-Adamantanone (700-58-3) + 4-bromo-aniline (106-40-1) → N-(4-bromophenyl)adamantan-2-amine (87913-26-6)

Guidance literature:

With rhodium(III) chloride hydrate; carbon monoxide; In acetonitrile; at 140 ℃; for 11h; Autoclave; Molecular sieve;

DOI:10.1021/ol503595m

Reference yield: 57.0%

1.4-dibromobenzene (106-37-6) + N-(2-adamantyl)amine (13074-39-0) → N-(4-bromophenyl)adamantan-2-amine (87913-26-6)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; bis(dibenzylideneacetone)-palladium⁽⁰⁾; sodium t-butanolate; In 1,4-dioxane; for 7h; Reflux; Under argon;

DOI:10.1134/S1070428010010069

Reference yield: 94.0%

2-(2-methylphenyl)pyridine (10273-89-9) + N-(4-bromophenyl)adamantan-2-amine (87913-26-6) → C28H30N2

Guidance literature:

With C₁₇H₂₄N₅Ru⁽¹⁺⁾*F₆P^(1-); potassium acetate; potassium carbonate; In 1-methyl-pyrrolidin-2-one; at 35 ℃; for 24h; Inert atmosphere;

DOI:10.1038/s41557-018-0062-3

upstream raw materials:

1.4-dibromobenzene

N-(2-adamantyl)amine

2-Adamantanone

4-bromo-aniline

Refernces

• 1、 Kolesnikov, Pavel N.,Yagafarov, Niyaz Z.,Usanov, Dmitry L.,Maleev, Victor I.,Chusov, Denis. "Ruthenium-catalyzed reductive amination without an external hydrogen source". supporting information. p. 173 - 175. Retrieved 2015/01/30.