Bromantane belongs to the adamantane derivatives — a family built around a rigid, cage-shaped hydrocarbon core whose fragment appears in a wide range of laboratory reagents. In this particular molecule the cage is joined through a single nitrogen atom to a brominated aromatic ring. CAS number 87913-26-6, molecular formula C16H20BrN, molar mass 306.25 g/mol.
Molecular skeleton and functional groups
The core is adamantane, a tricyclic assembly of ten carbon atoms whose geometry reproduces a fragment of the diamond lattice. Substitution occurs at a bridge position rather than a bridgehead, which carries two consequences. The molecule keeps a mirror plane despite its bulky three-dimensional shape, so no stereogenic centre is present. At the same time, that carbon forms an unusually stable cation, and this single fact shapes the practical routes to the compound.
The second module is a phenyl ring carrying bromine in the para position. Bromine withdraws electron density, is highly polarisable, and leaves an unmistakable isotopic fingerprint in mass spectra. The two modules are bridged by a secondary aromatic amine that retains one proton on nitrogen — the only polar group in the whole structure, the only basic site, and simultaneously the most vulnerable point of the molecule. With hydrocarbon bulk dominating over the polar fragment, the material behaves as a distinctly lipophilic solid.
Chemical class and related compounds
- adamantane — the parent cage hydrocarbon of the whole family,
- 1-aminoadamantane — the simplest aminoadamantane, substituted at a bridgehead position,
- memantine and rimantadine — further adamantane amines differing in side-chain branching,
- 2-adamantanol and the corresponding cage ketone — functionalised building blocks,
- 4-bromoaniline — the second substrate and a residual impurity worth monitoring,
- Ladasten — a trade name covering the very same chemical entity, sharing the CAS number,
- ring analogues bearing chlorine or fluorine instead of bromine.
Synthetic approaches described in the literature
- Obtaining an adamantane derivative functionalised at a bridge position; oxidation of the parent hydrocarbon yields the cage ketone, which is also a catalogue reagent.
- Condensation of that ketone with the brominated aniline, proceeding through nitrogen addition to the carbonyl group followed by loss of water, to give a Schiff base.
- Reduction of the resulting carbon–nitrogen double bond to the secondary amine, using hydride reagents or catalytic hydrogenation.
- An ionic alternative: acid-mediated solvolysis of an adamantyl precursor and capture of the resulting cation by the aromatic nitrogen — a shorter route, but more prone to double substitution.
- Purification exploiting the basic nitrogen: conversion to a salt, washing of the aqueous phase, liberation of the free base and final crystallisation. Residual aniline deserves particular attention and is readily detected chromatographically.
The account is deliberately qualitative. Reaction parameters differ between publications and are not reproduced here.
Stability, degradation and influencing factors
| Factor | Observed influence | Laboratory recommendation |
|---|---|---|
| Light, ultraviolet in particular | weakening of the carbon–bromine bond, gradual darkening of the powder | amber glassware or opaque packaging |
| Atmospheric oxygen | oxidation of the aromatic amine towards coloured secondary products | tight closure, inert gas blanket after opening |
| Strong oxidisers | degradation of the aniline ring | separate storage away from peroxides and nitrates |
| Acidic media | protonation of nitrogen and conversion to a salt — reversible, but altering solubility | used deliberately during extraction, undesirable during direct measurement |
| Elevated drying temperature | material loss and, on prolonged heating, skeletal decomposition | gentle drying, preferably under reduced pressure |
| Humidity | limited impact given the lipophilic character, caking possible | desiccator with silica gel |
Solubility and preparation of working solutions
The hydrocarbon skeleton combined with bromine renders the compound practically insoluble in water while readily soluble in organic solvents of low and medium polarity: dichloromethane, chloroform, ethanol or dimethyl sulfoxide. Stock solutions are normally prepared in an aprotic solvent, and aqueous dilutions require a co-solvent, since rapid introduction into water makes the substance drop out of solution.
Dissolution benefits from stirring supported by an ultrasonic bath, and clarity is best judged in side lighting against a dark background. Solutions destined for chromatography should be filtered so that fine particles do not foul the column. When working with a salt form, remember that its affinity for water differs markedly from that of the free base — a frequent source of confusion when comparing procedures from different sources. See also our laboratory reagent listing: L-Tyrosine / L-Tyrosyna /Tyrozyna Czystość ≥ 99% 100.
Spectral characteristics
The proton spectrum splits into two readable regions. The aliphatic range shows a dense, overlapping envelope of cage signals with the proton adjacent to nitrogen clearly displaced from the rest. The aromatic range is occupied by the four-spin pattern typical of para substitution, seen as two apparent doublets. The proton on nitrogen appears as a broad signal that disappears after shaking with deuterated water. The carbon spectrum is markedly simplified by cage symmetry, and the carbon bearing bromine is recognised by its characteristic shift. See also our reagent grade material: IDRA-21, czystość ≥ 99% 1000mg.
The most convincing proof of identity, however, comes from mass spectrometry: the two natural bromine isotopes of comparable abundance turn the molecular ion into a pair of signals of nearly equal intensity separated by two mass units, accompanied by a persistent adamantyl fragment. Infrared spectra show the secondary amine N–H stretch alongside aromatic ring bands, while the aniline chromophore permits ultraviolet detection in chromatographic work.
Product classification. The material is not intended for human use. It is not a veterinary product either. Intended use: laboratory work and analytical determination by HPLC and GC-MS. Not a medicine, medical device or food product.
Related reagents
- IDRA-21, czystość ≥ 99% 1000mg
- L-Tyrosine / L-Tyrosyna /Tyrozyna Czystość ≥ 99% 1000mg
- Bleu de méthylène / BLEU DE MÉTHYLÈNE. Pureté ≥ 99,99% 1000mg.
- CBD / Cannabidiol / Cannabidiol, Krishals ≥ 99.85% 1000mg!
Selected references
Records indexed in PubMed for this substance; each entry is identified by its PMID.
- Bugaeva LI, Eksperimental'naia i klinicheskaia farmakologiia, 2000 — PMID 10763112
- Morozov IS, Eksperimental'naia i klinicheskaia farmakologiia, 1998 — PMID 9929819
- Iëzhitsa IN, Eksperimental'naia i klinicheskaia farmakologiia, 2000 — PMID 11109517
- Seredenin SB, Biulleten' eksperimental'noi biologii i meditsiny, 1999 — PMID 10640239
