21524-34-5

Basic information

• Product Name: 1-BROMO-2,4,6-TRIISOPROPYLBENZENE
• Synonyms: 1-Bromo-2,4,6-triisopropylbenzene~2,4,6-Triisopropylbromobenzene;1-Bromo-2,4,6-triisopropylbenzene, 98+%;2,4,6-Triisopropylbromobenzene;2,4,6-Triisopropylbromobenzene, 2-Bromo-1,3,5-triisopropylbenzene;1,3,5-Triisopropyl-2-bromobenzene;2,4,6-Triisopropylphenyl bromide;2-bromo-1,3,5-tri(propan-2-yl)benzene;1-BroMo-2,4,6-tri-i-propylbenzene
• CAS NO: 21524-34-5
• Molecular Formula: C₁₅H₂₃Br
• Molecular Weight: 283.25
• EINECS: 1312995-182-4
• Product Categories: Indolines ,Indoles ,Indazoles
• Mol File: 21524-34-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 96-97 °C0.1 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.118 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00252mmHg at 25°C
• Refractive Index: n20/D 1.523(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Slightly miscible with water.
• BRN: 1953440
• CAS DataBase Reference: 1-BROMO-2,4,6-TRIISOPROPYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,4,6-TRIISOPROPYLBENZENE(21524-34-5)
• EPA Substance Registry System: 1-BROMO-2,4,6-TRIISOPROPYLBENZENE(21524-34-5)

Safety Data

• Safety Statements: 23-24/25
• WGK Germany: 3
• Hazardous Substances Data: 21524-34-5(Hazardous Substances Data)

Usage

Description

1-BROMO-2,4,6-TRIISOPROPYLBENZENE is a colorless liquid that is a bromine-substituted aromatic compound with three isopropyl groups attached to the 2nd, 4th, and 6th carbon positions on the benzene ring. It is a versatile intermediate in organic synthesis and has various applications in different industries.

Uses

Used in Suzuki Reaction:
1-BROMO-2,4,6-TRIISOPROPYLBENZENE is used as a reactant in the Suzuki reaction, a widely employed cross-coupling reaction in organic chemistry. This reaction allows for the formation of carbon-carbon bonds, which are crucial in the synthesis of complex organic molecules, including pharmaceuticals and agrochemicals.
Used in Pharmaceutical Production:
1-BROMO-2,4,6-TRIISOPROPYLBENZENE is used as a building block for the synthesis of 1-fluoro-2,4,6-triisopropylbenzene, a fluorine-substituted aromatic compound. 1-BROMO-2,4,6-TRIISOPROPYLBENZENE serves as an important intermediate in the production of various pharmaceuticals, as the presence of fluorine can significantly alter the properties and biological activity of the resulting molecules.
Used in Agrochemical Synthesis:
1-BROMO-2,4,6-TRIISOPROPYLBENZENE is also used as a starting material for the synthesis of agrochemicals, specifically in the production of 1-fluoro-2,4,6-triisopropylbenzene. The fluorinated aromatic compounds derived from this intermediate can be used to develop new pesticides, herbicides, and other agrochemicals with improved efficacy and selectivity.
Used in Synthesis of Di-2,4,6-triisopropylphenyl Diselenide:
1-BROMO-2,4,6-TRIISOPROPYLBENZENE can be used in the synthesis of di-2,4,6-triisopropylphenyl diselenide, a compound with potential applications in various fields, including materials science and medicinal chemistry. The reaction involves the use of metallic selenium and tertiary-butyl lithium to form the diselenide compound.

Synthesis Reference(s)

Synthesis, p. 621, 1976 DOI: 10.1055/s-1976-24146

InChI:InChI=1/C15H23Br/c1-9(2)12-7-13(10(3)4)15(16)14(8-12)11(5)6/h7-11H,1-6H3

Upstream product

• 717-74-8 1,3,5-triisopropyl benzene 
• 56-23-5 tetrachloromethane 
• 7726-95-6 bromine 
• 148163-04-6 (2,4,6-triisopropylphenyl)dihexylborane 
• 71-43-2 benzene 

Downstream Products

• 49623-71-4 2,4,6-triisopropylbenzoic acid 
• 137144-19-5 2,4,6-triisopropylphenyl 9-xanthenyl ketone 
• 53356-73-3 dichloro(2,4,6-tri-isopropylphenyl)phosphane 
• 182227-72-1 bis(2,4,6-tri-isopropylphenyl)phosphinous chloride 
• 71518-96-2 bis(2,4,6-triisopropylphenyl)diselenide 
• 147050-16-6 bis(2,4,6-triisopropylphenyl)phosphinic chloride 
• 99686-15-4 C₂₂H₂₈N^(1-)*Br^(1-)*Mg⁽²⁺⁾ 
• 63846-76-4 ethyl 2,4,6-tri-isopropylbenzoate 
• 24249-82-9 2,4,6-triisopropylbenzaldehyde 
• 177552-71-5 2,4,6,2',4',6'-hexaisopropylbenzhydrol 
• 177552-70-4 Formic acid bis-(2,4,6-triisopropyl-phenyl)-methyl ester 
• 108894-99-1 (2,4,6-triisopropylphenyl)magnesium bromide 
• 196085-28-6 PCl(CH₂Cl)(C₆H₂(C₃H₇)3) 
• 717-74-8 1,3,5-triisopropyl benzene 

Relevant articles and documents

Stepwise mechanism for the bromination of arenes by a hypervalent iodine reagent

A mild, metal-free bromination method of arenes has been developed using the combination of bis(trifluoroacetoxy)iodobencene and trimethylsilyl bromide. In situ-formed dibromo(phenyl)-λ3-iodane (PhIBr2) is proposed as the reactive intermediate. This methodology using PIFA/TMSBr has been applied with success to a great number of substrates (25 examples). The treatment of mono-substituted activated arenes led to para-brominated products (2u-z) in excellent 83-96% yields. Density functional theory calculations indicate a stepwise mechanism involving a double bromine addition followed by a type II dyotropic reaction with concomitant re-aromatization of the six-membered ring.

Reactivity and synthetic utility of 1-(arenesulfonyloxy) benziodoxolones

The reactivity and synthetic use of 1-(arenesulfonyloxy)benziodoxolones were studied. In the presence of iodine, 1-(arenesulfonyloxy)benziodoxolones iodinated various aromatics to give iodoarenes in moderate to good yields. In particular, 1-(p-chlorobenzenesulfonyloxy)benziodoxolone showed the best reactivity. Using a halide salt such as lithium bromide or lithium chloride instead of iodine, the corresponding aryl bromides and chlorides were also obtained in good yields. In the absence of aromatics, 1- (arenesulfonyloxy)benziodoxolones gave rise to desulfonyloxyiodination reactions to give the corresponding aryl iodides via electrophilic ipso substitution on the aromatic rings. Furthermore, the l-(p- toluenesulfonyloxy)benziodoxolone/iodine system iodotosyloxylated alkynes in good yields. These reactions proceeded via the formation of arenesulfonyl hypoiodites.

Phospholes with reduced pyramidal character from steric crowding III NMR and X-ray diffraction studies on 1-( 2,4,6-tri-isopropylphenyl)-3-methylphosphole

The 2,4,6-tri-isopropylphenyl substituent was placed on the phosphorus of a phosphole to reduce the pyramidal character. That this was accomplished was revealed by single crystal X-ray diffraction analysis; with respect to the plane of C2-P-C5 in the phosphole ring, the ipso carbon of the benzene ring was deflected by only 58.0°, whereas the deflection is 66.9° in the uncrowded 1-benzylphosphole. This proves that the concept of reducing the pyramidal character (with the goal of increasing the electron delocalization) through steric crowding can be realized. In the crystal the two rings are in orthogonal planes, but this relation is not retained in solution; NMR studies show that the two edges of the benzene ring, as well as the 2,6-isopropyl groups, are identical.