Mesityl bromide

Last updated
Mesityl bromide
Mesitylbromide.svg
Names
Other names
2-bromomesitylene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.008.552 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 209-405-9
PubChem CID
UNII
  • InChI=1S/C9H11Br/c1-6-4-7(2)9(10)8(3)5-6/h4-5H,1-3H3
    Key: RRTLQRYOJOSPEA-UHFFFAOYSA-N
  • CC1=CC(=C(C(=C1)C)Br)C
Properties
C9H11Br
Molar mass 199.091 g·mol−1
Appearancecolorless liquid
Density 1.3220 g/cm3
Melting point −1 °C (30 °F; 272 K)
Boiling point 225 °C (437 °F; 498 K)
Hazards
GHS labelling: [1]
GHS-pictogram-exclam.svg
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Mesityl bromide is an organic compound with the formula (CH3)3C6H2Br. It is a derivative of mesitylene (1,3,5-trimethylbenzene) with one ring H replaced by Br. The compound is a colorless oil. It is a standard electron-rich aryl halide substrate for cross coupling reactions. [2] With magnesium it reacts to give the Grignard reagent, [3] which is used in the preparation of tetramesityldiiron.

It is prepared by the direct reaction of bromine with mesitylene: [4]

(CH3)3C6H3 + Br2 → (CH3)3C6H2Br + HBr

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.

The Friedel–Crafts reactions are a set of reactions developed by Charles Friedel and James Crafts in 1877 to attach substituents to an aromatic ring. Friedel–Crafts reactions are of two main types: alkylation reactions and acylation reactions. Both proceed by electrophilic aromatic substitution.

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

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<span class="mw-page-title-main">Tebbe's reagent</span> Chemical compound

Tebbe's reagent is the organometallic compound with the formula (C5H5)2TiCH2ClAl(CH3)2. It is used in the methylidenation of carbonyl compounds, that is it converts organic compounds containing the R2C=O group into the related R2C=CH2 derivative. It is a red solid that is pyrophoric in the air, and thus is typically handled with air-free techniques. It was originally synthesized by Fred Tebbe at DuPont Central Research.

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

Diphenylacetylene is the chemical compound C6H5C≡CC6H5. The molecule consists of two phenyl groups attached to a C2 unit. A colorless solid, it is used as a building block in organic synthesis and as a ligand in organometallic chemistry.

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

In organic chemistry, 1-propenyl (or simply propenyl) has the formula CH=CHCH3 and 2-propenyl (isopropenyl) has the formula CH2=C-CH3. These groups are found in many compounds. Propenyl compounds are isomeric with allyl compounds, which have the formula CH2-CH=CH2.

The Béchamp reduction is a chemical reaction that converts aromatic nitro compounds to their corresponding anilines using iron as the reductant:

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

Dimethylbenzylamine is the organic compound with the formula C6H5CH2N(CH3)2. The molecule consists of a benzyl group, C6H5CH2, attached to a dimethylamino functional group. It is a colorless liquid. It is used as a catalyst for the formation of polyurethane foams and epoxy resins.

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

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

Cyclohexanone oxime is an organic compound containing the functional group oxime. This colorless solid is an important intermediate in the production of nylon 6, a widely used polymer.

<span class="mw-page-title-main">Isodurene</span> Organic compound

Isodurene or 1,2,3,5-tetramethylbenzene is an organic compound with the formula C6H2(CH3)4, classified as an aromatic hydrocarbon. It is a flammable colorless liquid which is nearly insoluble in water but soluble in organic solvents. It occurs naturally in coal tar. Isodurene is one of three isomers of tetramethylbenzene, the other two being prehnitene (1,2,3,4-tetramethylbenzene) and durene (1,2,4,5-tetramethylbenzene).

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

Aminomethyl propanol is an organic compound with the formula H2NC(CH3)2CH2OH. It is colorless liquid that is classified as an alkanolamine. It is a useful buffer and a precursor to numerous other organic compounds.

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

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

<span class="mw-page-title-main">2-Aminobenzaldehyde</span> Chemical compound

2-Aminobenzaldehyde is an organic compound with the formula C6H4(NH2)CHO. It is one of three isomers of aminobenzaldehyde. It is a low-melting yellow solid that is soluble in water.

<i>meso</i>-Stilbene dibromide Organic molecule

meso-Stilbene dibromide is an organic compound with a formula of (C6H5CH(Br))2. It is one of three isomeric stilbene dibromides, the others being the pair of enantiomers. All are white solids.

In organic chemistry, vinylation is the process of attaching a vinyl group to a substrate. Many organic compounds contain vinyl groups, so the process has attracted significant interest, especially since the reaction scope includes substituted vinyl groups. The reactions can be classified according to the source of the vinyl group.

<i>tert</i>-Butyl hypochlorite Chemical compound

tert-Butyl hypochlorite is the organic compound with the formula (CH3)3COCl. A yellow liquid, it is a rare example of an organic hypochlorite, i.e. a compound with an O-Cl bond. It is a reactive material that is useful for chlorinations. It can be viewed as a lipophilic version of sodium hypochlorite (bleach).

<span class="mw-page-title-main">Bis(dimethylamino)methane</span> Chemical compound

Bis(dimethylamino)methane is the organic compound with the formula [(CH3)2N]2CH2. It is classified as an aminal as well as a ditertiary amine, in fact the simplest. It is a colorless liquid that is widely available. It is prepared by the reaction of dimethylamine and formaldehyde:

References

  1. "2-Bromomesitylene". pubchem.ncbi.nlm.nih.gov.
  2. Farina, Vittorio; Krishnamurthy, Venkat; Scott, William J. (1997). "The Stille Reaction". Organic Reactions. pp. 1–652. doi:10.1002/0471264180.or050.01. ISBN   0471264180.
  3. Lee Irvin Smith (1931). "Isoodurene". Org. Synth. 11: 66. doi:10.15227/orgsyn.011.0066.
  4. Lee Irvin Smith (1931). "Bromomesitylene". Org. Synth. 11: 24. doi:10.15227/orgsyn.011.0024.