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

Chemical Properties

Colorless liquid

Uses

Different sources of media describe the Uses of 21524-34-5 differently. You can refer to the following data:
1. suzuki reaction
2. 1-Bromo-2,4,6-triisopropylbenzene can be used in the synthesis of 1-fluoro-2,4,6-triisopropylbenzene, a fluorine-substituted aromatic building block for agrochemical synthesis and pharmaceutical production. It can also be used in the synthesis of di-2,4,6-triisopropylphenyl diselenide via reaction with metallic selenium in the presence of tertiary-butyl lithium.

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

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

Downstream Products

• 49623-71-4 2,4,6-triisopropylbenzoic acid 
• 592507-77-2 (R)-(+)-2,4,6-triisopropylphenylsulfinamide 
• 717-74-8 1,3,5-triisopropyl benzene 
• 443295-47-4 5'-bromo-2,4,6,2'',4'',6''-hexaisopropyl-1,1:3',1''-terphenyl 
• 114070-56-3 2,4,6-tri-isopropylphenylphosphonic dichloride 
• 114070-60-9 C₁₉H₃₃ClNP 
• 114070-82-5 N,N-dimethyl-P-(2,4,6-tri-isopropylphenyl)phosphonamidic chloride 
• 114964-68-0 2,4,6-tri-isopropylbenzeneselenol 
• 857356-94-6 2-di-tertbutylphosphino-3,4,5,6-tetramethyl-2',4',6'-triisopropyl-1,1'-biphenyl 
• 815617-49-3 3-methyl-1-(2,4,6-triisopropyl-phenyl)-phosphinane 

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.