1,3,5-Tribromobenzene

Last updated
1,3,5-Tribromobenzene [1] [2]
1,3,5-tribromobenzene.svg
1,3,5-tribromobenzene vdw.png
1,3,5-Tribromobenzene sample.jpg
Names
IUPAC name
1,3,5-Tribromobenzene
Other names
sym-Tribromobenzene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.009.953 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 210-947-3
PubChem CID
UNII
  • InChI=1S/C6H3Br3/c7-4-1-5(8)3-6(9)2-4/h1-3H
    Key: YWDUZLFWHVQCHY-UHFFFAOYSA-N
  • C1=C(C=C(C=C1Br)Br)Br
Properties
C6H3Br3
Molar mass 314.802 g·mol−1
Appearancecolorless solid
Melting point 122 °C (252 °F; 395 K)
Boiling point 271 °C (520 °F; 544 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3,5-Tribromobenzene is an aryl bromide and isomer of tribromobenzene, also known as sym-tribromobenzene. [2]

Contents

Preparation

Brominating aniline with elemental bromine gives 2,4,6-tribromoaniline. This is then diazotized, then reacted with ethanol to replace the diazonium group with hydrogen, forming 1,3,5-tribromobenzene. [3]

It has also been prepared by these methods: [3]

Reactions and uses

1,3,5-tris(4-formylphenyl)benzene (TFPB) 1,3,5-tris(4-formylphenyl)benzene.svg
1,3,5-tris(4-formylphenyl)benzene (TFPB)

1,3,5-Tribromobenzene is a precursor to C3-symmetric molecules. It undergoes a Suzuki reaction with three equivalents of 4-formylphenylboronic acid to form 1,3,5-tris(4-formylphenyl)benzene (TFPB), a monomer for covalent organic frameworks. [4]

Related Research Articles

Mesitylene or 1,3,5-trimethylbenzene is a derivative of benzene with three methyl substituents positioned symmetrically around the ring. The other two isomeric trimethylbenzenes are 1,2,4-trimethylbenzene (pseudocumene) and 1,2,3-trimethylbenzene (hemimellitene). All three compounds have the formula C6H3(CH3)3, which is commonly abbreviated C6H3Me3. Mesitylene is a colorless liquid with sweet aromatic odor. It is a component of coal tar, which is its traditional source. It is a precursor to diverse fine chemicals. The mesityl group (Mes) is a substituent with the formula C6H2Me3 and is found in various other compounds.

<span class="mw-page-title-main">Charge-transfer complex</span> Association of molecules in which a fraction of electronic charge is transferred between them

In chemistry, a charge-transfer (CT) complex or electron-donor-acceptor complex describes a type of supramolecular assembly of two or more molecules or ions. The assembly consists of two molecules that self-attract through electrostatic forces, i.e., one has at least partial negative charge and the partner has partial positive charge, referred to respectively as the electron acceptor and electron donor. In some cases, the degree of charge transfer is "complete", such that the CT complex can be classified as a salt. In other cases, the charge-transfer association is weak, and the interaction can be disrupted easily by polar solvents.

<span class="mw-page-title-main">Triazine</span> Aromatic, heterocyclic compound

Triazines are a class of nitrogen-containing heterocycles. The parent molecules' molecular formula is C3H3N3. They exist in three isomeric forms, 1,3,5-triazines being common.

<span class="mw-page-title-main">Phloroglucinol</span> Chemical compound

Phloroglucinol is an organic compound with the formula C6H3(OH)3. It is a colorless solid. It is used in the synthesis of pharmaceuticals and explosives. Phloroglucinol is one of three isomeric benzenetriols. The other two isomers are hydroxyquinol (1,2,4-benzenetriol) and pyrogallol (1,2,3-benzenetriol). Phloroglucinol, and its benzenetriol isomers, are still defined as "phenols" according to the IUPAC official nomenclature rules of chemical compounds. Many such monophenolics are often termed polyphenols.

The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered by and named after Hermann Staudinger. The reaction follows this stoichiometry:

<span class="mw-page-title-main">Acetaldehyde ammonia trimer</span> Chemical compound

Acetaldehyde ammonia trimer is a chemical compound described by the formula (CH3CHNH)3. The pure material is colourless but samples often appear light yellow or slightly beige due to the degradation by oxidation. It is hygroscopic, and can be found in a trihydrate form.

1,3,5-Triazine, also called s-triazine, is an organic chemical compound with the formula (HCN)3. It is a six-membered heterocyclic aromatic ring, one of several isomeric triazines. S-triazine—the "symmetric" isomer—and its derivatives are useful in a variety of applications.

The tropylium ion or cycloheptatrienyl cation is an aromatic species with a formula of [C7H7]+. Its name derives from the molecule tropine from which cycloheptatriene (tropylidene) was first synthesized in 1881. Salts of the tropylium cation can be stable, even with nucleophiles of moderate strength e.g., tropylium tetrafluoroborate and tropylium bromide (see below). Its bromide and chloride salts can be made from cycloheptatriene and bromine or phosphorus pentachloride, respectively.

<span class="mw-page-title-main">Thial</span> Chemical group (–CH=S)

In organic chemistry, a thial or thioaldehyde is a functional group which is similar to an aldehyde, RC(O)H, in which a sulfur (S) atom replaces the oxygen (O) atom of the aldehyde. Thioaldehydes are even more reactive than thioketones. Unhindered thioaldehydes are generally too reactive to be isolated — for example, thioformaldehyde, H2C=S, condenses to the cyclic trimer 1,3,5-trithiane. Thioacrolein, H2C=CHCH=S, formed by decomposition of allicin from garlic, undergoes a self Diels-Alder reaction giving isomeric vinyldithiins. While thioformaldehyde is highly reactive, it is found in interstellar space along with its mono- and di-deuterated isotopologues. With sufficient steric bulk, however, stable thioaldehydes can be isolated.

<span class="mw-page-title-main">Picryl chloride</span> Chemical compound

Picryl chloride is an organic compound with the formula ClC6H2(NO2)3. It is a bright yellow solid that is highly explosive, as is typical for polynitro aromatics such as picric acid. Its detonation velocity is 7,200 m/s.

<span class="mw-page-title-main">Tropone</span> Chemical compound

Tropone or 2,4,6-cycloheptatrien-1-one is an organic compound with some importance in organic chemistry as a non-benzenoid aromatic. The compound consists of a ring of seven carbon atoms with three conjugated alkene groups and a ketone group. The related compound tropolone (2-hydroxy-2,4,6-cycloheptatrien-1-one) has an additional alcohol group next to the ketone. Tropones are uncommon in natural products, with the notable exception of the 2-hydroxyl derivatives, which are called tropolones.

<span class="mw-page-title-main">Group 2 organometallic chemistry</span>

Group 2 organometallic chemistry refers to the chemistry of compounds containing carbon bonded to any group 2 element. By far the most common group 2 organometallic compounds are the magnesium-containing Grignard reagents which are widely used in organic chemistry. Other organometallic group 2 compounds are rare and are typically limited to academic interests.

<span class="mw-page-title-main">1,3,5-Trithiane</span> Chemical compound

1,3,5-Trithiane is the chemical compound with the formula (CH2S)3. This heterocycle is the cyclic trimer of the otherwise unstable species thioformaldehyde. It consists of a six-membered ring with alternating methylene bridges and thioether groups. It is prepared by treatment of formaldehyde with hydrogen sulfide.

Covalent organic frameworks (COFs) are a class of porous polymers that form two- or three-dimensional structures through reactions between organic precursors resulting in strong, covalent bonds to afford porous, stable, and crystalline materials. COFs emerged as a field from the overarching domain of organic materials as researchers optimized both synthetic control and precursor selection. These improvements to coordination chemistry enabled non-porous and amorphous organic materials such as organic polymers to advance into the construction of porous, crystalline materials with rigid structures that granted exceptional material stability in a wide range of solvents and conditions. Through the development of reticular chemistry, precise synthetic control was achieved and resulted in ordered, nano-porous structures with highly preferential structural orientation and properties which could be synergistically enhanced and amplified. With judicious selection of COF secondary building units (SBUs), or precursors, the final structure could be predetermined, and modified with exceptional control enabling fine-tuning of emergent properties. This level of control facilitates the COF material to be designed, synthesized, and utilized in various applications, many times with metrics on scale or surpassing that of the current state-of-the-art approaches.

<span class="mw-page-title-main">Two-dimensional polymer</span>

A two-dimensional polymer (2DP) is a sheet-like monomolecular macromolecule consisting of laterally connected repeat units with end groups along all edges. This recent definition of 2DP is based on Hermann Staudinger's polymer concept from the 1920s. According to this, covalent long chain molecules ("Makromoleküle") do exist and are composed of a sequence of linearly connected repeat units and end groups at both termini.

<span class="mw-page-title-main">2,4,6-Tribromoaniline</span> Chemical compound

2,4,6-Tribromoaniline is a brominated derivative of aniline with the formula C6H4Br3N. It is used in organic synthesis of pharmaceuticals, agrochemicals and fire-extinguishing agents.

<span class="mw-page-title-main">Trithioacetone</span> Chemical compound

Trithioacetone (2,2,4,4,6,6-hexamethyl-1,3,5-trithiane) is an organic chemical with formula C
9
H
18
S
3
. Its covalent structure is [–C(CH
3
)
2
–S–]
3
, that is, a six-membered ring of alternating carbon and sulfur atoms, with two methyl groups attached to each carbon. It can be viewed as a derivative of 1,3,5-trithiane, with methyl-group substituents for all of the hydrogen atoms in that parent structure.

<span class="mw-page-title-main">2,4,6-Trinitrobenzoic acid</span> Impact-resistant high explosive

2,4,6-Trinitrobenzoic acid (TNBA) is an organic compound with the formula (O2N)3C6H2CO2H. It is a high explosive nitrated derivative of benzoic acid.

<span class="mw-page-title-main">4-Bromobenzaldehyde</span> Chemical compound

4-Bromobenzaldehyde, or p-bromobenzaldehyde, is an isomer of bromobenzaldehyde.

<span class="mw-page-title-main">Tribromobenzene</span>

Tribromobenzenes are a group of bromobenzenes with the formula C6H3Br3, consisting of three bromine atoms bonded to a central benzene ring.

References

  1. "1,3,5-Tribromobenzene". ChemSpider . Retrieved 25 December 2023.
  2. 1 2 "1,3,5-Tribromobenzene". PubChem . Retrieved 25 December 2023.
  3. 1 2 Coleman, G. H.; Talbot, William F. (1933). "sym.-Tribromobenzene". Organic Syntheses . 13: 96. doi:10.15227/orgsyn.013.0096.
  4. Bunck, David N.; Dichtel, William R. (2013). "Bulk Synthesis of Exfoliated Two-Dimensional Polymers Using Hydrazone-Linked Covalent Organic Frameworks". Journal of the American Chemical Society . 135 (40): 14952–14955. doi:10.1021/ja408243n. PMID   24053107.