Hexakis(bromomethyl)benzene

• CAS: 3095-73-6
• Catalog Number: ACM3095736
• Category: Main Products
• Molecular Weight: 635.65
• Molecular Formula: C6(CH2Br)6

Case Study

Hexakis(bromomethyl)benzene for Gabriel synthesis

Masuda, Junya, et al. ChemistrySelect 3.22 (2018): 6112-6115.

Hexakis(aminomethyl)benzene is a key precursor for various hexasubstituted functional molecules. Nucleophilic substitution of hexakis(bromomethyl)benzene with potassium phthalimide afforded hexakis(bromomethyl)benzene in excellent yields. Hydrazide decomposition of the phthalimide moiety of hexakis(bromomethyl)benzene afforded a mixture of hexakis(aminomethyl)benzene and 2,3-dihydrophthaloyl-1,4-dione. Pure hexakis(aminomethyl)benzene was isolated as its hexahydrochloride salt after treatment of the mixture with HCl. Alkyl-substituted hexakis(aminomethyl)benzene exhibits extremely high solubility in nonpolar organic solvents. Density functional theory calculations of the hexakis(bromomethyl)benzene structure showed that all substituents are directed to the same side via intramolecular hydrogen bonds.
Hexamethyl(bromomethyl)benzene underwent nucleophilic substitution with potassium phthalimide in DMF at 70 °C to afford hexamethyl(phthalimidomethyl)benzene in 92% yield. The phthalimide moiety of hexamethyl(phthalimidomethyl)benzene 4 was hydrogenated in EtOH to afford hexamethyl(aminomethyl)benzene. Pure hexamethyl(aminomethyl)benzene was isolated as its hexahydrochloride salt by treating the crude mixture with HCl.

The synthesized product of hexakis(bromomethyl)benzene used for molecular structural studies

Gavette, Jesse V., Andrew L. Sargent, and William E. Allen. The Journal of Organic Chemistry 73.9 (2008): 3582-3584.

Hexamines were obtained in high yield by treating hexakis(bromomethyl)benzene with excess NaN3 followed by hydrogenation of the resulting polyazides. Coupling with six equivalents of nonanoic acid afforded the hexamide without chromatographic purification. The NH resonance peak of the hexamide appears very low field in CDCl3 and is not affected by concentration changes or the addition of chloride or triflate ions. DFT calculations predict that the hexamide exists as a bowl-shaped structure with all six substituents attached to one side of the plane defined by the anchoring aromatics via intramolecular hydrogen bonds.
A round-bottom flask was charged with 50 mL of DMF and 10.19 g of hexakis(bromomethyl)benzene. Sodium azide was added in portions over several minutes with stirring. After 24 h at room temperature, the contents of the flask were poured into 500 mL of water. The precipitated product was collected by filtration, washed with water, and dried in vacuo to give 5.35 g (82%) of light tan hexakis(azidomethyl)benzene.

Hexakis(bromomethyl)benzene for the synthesis and conformational analysis of organic molecules

Alexander, Daniel, et al. Collection of Czechoslovak Chemical Communications 65.5 (2000): 673-694.

The selective sixfold monoalkylation of carbanions CH(COOR) 2- (R = Me, Et, t-Bu, Bn) with hexakis(bromomethyl)benzene afforded compounds in high yields. Upon subsequent replacement of the acidic α-hydrogen with bulky substituents, a variety of α-X-per-substituted homologues and derivatives were provided (X = Me, Et, Bu, Oc, Bn, Br, N). The effect of variable X substituents on the conformation was investigated by single crystal X-ray diffraction and compared with the results obtained by theoretical calculations.
Dimethyl malonate (23.78 g, 180 mmol), sodium hydride/oil suspension (5.69 g, 140 mmol) and hexakis(bromomethyl)benzene (12.71 g, 20 mmol) were prepared in dimethyl sulfoxide (200 ml). The crude product was crystallized from methanol and recrystallized from ethyl acetate, melting point 167-168 °C, yield 15.3 g (65%).

Hexakis(bromomethyl)benzene for the synthesis of selective ionophores

Singh, Jai Deo, et al. Tetrahedron Letters 49.1 (2008): 117-121.

Hexakis(bromomethyl)benzene for the synthesis and conformational analysis of organic molecules A new class of hexaalkyl(alkylseleno)benzenes [(RSeCH2)6C6] was demonstrated by the reaction of hexaalkyl(bromomethyl)benzenes with RSe ions. Preliminary data on ion sensing properties suggest that these species may act as selective ionophores for Hg ions.
The reaction of hexaalkyl(bromomethyl)benzenes with a sixfold excess of aliphatic selenate anions (generated in situ by the reaction of sodium borohydride and RSe in aqueous THF) proceeded cleanly. Column chromatography followed by recrystallization afforded hexaalkyl(alkylseleno)benzenes 1-9 in good yields. Only hexasubstituted positions were observed in each case. The purity, stability, and solubility of these molecules compared to aromatic analogs suggest their potential applications.

Custom Q&A

What is the molecular formula of Hexakis(bromomethyl)benzene?

The molecular formula of Hexakis(bromomethyl)benzene is C12H12Br6.

When was Hexakis(bromomethyl)benzene created in PubChem?

Hexakis(bromomethyl)benzene was created in PubChem on 2005-03-26.

What is the IUPAC name of Hexakis(bromomethyl)benzene?

The IUPAC name of Hexakis(bromomethyl)benzene is 1,2,3,4,5,6-hexakis(bromomethyl)benzene.

What is the molecular weight of Hexakis(bromomethyl)benzene?

The molecular weight of Hexakis(bromomethyl)benzene is 635.6 g/mol.

What is the Canonical SMILES representation of Hexakis(bromomethyl)benzene?

The Canonical SMILES representation of Hexakis(bromomethyl)benzene is C(C1=C(C(=C(C(=C1CBr)CBr)CBr)CBr)CBr)Br.

What is the InChIKey of Hexakis(bromomethyl)benzene?

The InChIKey of Hexakis(bromomethyl)benzene is XJOUCILNLRXRTF-UHFFFAOYSA-N.

How many rotatable bond counts are there in Hexakis(bromomethyl)benzene?

There are 6 rotatable bond counts in Hexakis(bromomethyl)benzene.

What is the topological polar surface area of Hexakis(bromomethyl)benzene?

The topological polar surface area of Hexakis(bromomethyl)benzene is 0Ų.

How many defined atom stereocenter counts are there in Hexakis(bromomethyl)benzene?

There are 0 defined atom stereocenter counts in Hexakis(bromomethyl)benzene.

What is the formal charge of Hexakis(bromomethyl)benzene?

The formal charge of Hexakis(bromomethyl)benzene is 0.