3975-77-7

Basic information

• Product Name: 1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE
• Synonyms: Bromobenzene, 2,4,6-tri-tert-butyl-;1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE;1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE 97+%;1-BroMo-2,4,6-tri-tert-butylbenzene 97%;Bromo(1,3,5-tris-tert-butyl)benzene;NSC 133894;2,4,6-Tri-tert-butylphenyl bromide
• CAS NO: 3975-77-7
• Molecular Formula: C₁₈H₂₉Br
• Molecular Weight: 325.33
• Product Categories: Aryl;C13 to C37+;Halogenated Hydrocarbons
• Mol File: 3975-77-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 168-173 °C(lit.)
• Boiling Point: 299.7°Cat760mmHg
• Flash Point: 123.7°C
• Appearance: /
• Density: 1.064g/cm³
• Vapor Pressure: 0.00209mmHg at 25°C
• Refractive Index: 1.494
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1913257
• CAS DataBase Reference: 1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE(3975-77-7)
• EPA Substance Registry System: 1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE(3975-77-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 3975-77-7(Hazardous Substances Data)

Usage

Description

1-Bromo-2,4,6-tri-tert-butylbenzene, also known as 2,4,6-tri-tert-butylbromobenzene, is a hindered aryl bromide with a unique structure that features three tert-butyl groups attached to the 2, 4, and 6 positions of the benzene ring. This structural arrangement provides significant steric hindrance, making it a valuable compound in various chemical reactions and applications.

Uses

Used in Chemical Synthesis:
1-Bromo-2,4,6-tri-tert-butylbenzene is used as a key intermediate in the synthesis of bulky biarylphosphine ligands. These ligands are crucial in the Pd-catalyzed C-O cross-coupling of a wide range of aryl halides and phenols, allowing for the reaction to occur under milder conditions.
Used in Organometallic Chemistry:
In the field of organometallic chemistry, 1-Bromo-2,4,6-tri-tert-butylbenzene is utilized to investigate the effect of increased steric bulk in dimethylindium(III) chalcogenolates. This research contributes to the understanding of the role of steric factors in organometallic compounds and their reactivity.
Used in Pharmaceutical Industry:
1-Bromo-2,4,6-tri-tert-butylbenzene may be used to form α,α-dimethyl-β-phenyl hydrostyrene by reacting with phenylboronic acid. 1-BROMO-2,4,6-TRI-TERT-BUTYLBENZENE has potential applications in the pharmaceutical industry, as it can be further modified and used as a building block for the development of new drugs with specific therapeutic properties.

InChI:InChI=1/C18H29Br/c1-16(2,3)12-10-13(17(4,5)6)15(19)14(11-12)18(7,8)9/h10-11H,1-9H3

Upstream product

• 1460-02-2 1,3,5-Tri-tert-butylbenzene 
• 40782-34-1 tris-(tert-butyl)benzene 
• 83466-54-0 Bis(2,4,6-tri-tert-butylphenyl)diphosphen 
• 7726-95-6 bromine 
• 7697-37-2 nitric acid 
• 64-19-7 acetic acid 
• 35383-91-6 2,4,6-tri-tert-butylphenyllithium 
• 13465-74-2 bromo trichloro silane 
• 71-43-2 benzene 

Downstream Products

• 17799-06-3 (2,4,6-tri-t-butyl)benzyl alcohol 
• 66415-27-8 2,4,6-tri-tert-butylbenzoic acid 
• 20996-29-6 7-<2,4,6-Tri-tert.-butyl-phenyl>-cycloheptatrien-(1,3,5) 
• 961-39-7 2,4,6-tri-tert-butylbenzenethiol 
• 1222-01-1 1,3,5-tris-tert-butyl toluene 
• 123133-03-9 4-(ethoxycarbonyl)phenyl 2,4,6-tri-t-butylphenyl selenide 
• 20333-40-8 dibutyl diselenide 
• 1460-02-2 1,3,5-Tri-tert-butylbenzene 
• 3975-81-3 2,4,6-tri(tert-butyl)benzaldehyde 
• 20875-32-5 bis(2,4,6-tri-tert-butyl)phenyl diselenide 
• 102737-63-3 6,8-di-t-butyl-3,4-dihydro-4,4-dimethyl-1H-2-benzoselenin 
• 102737-67-7 Butyl-[1-(2,4,6-tri-tert-butyl-phenyl)-meth-(E)-ylidene]-amine 
• 102737-64-4 C₃₈H₆₂Se₂ 
• 107396-03-2 1-deutero-2,4,6-tri-tert-butylbenzene 

Relevant articles and documents

Reactivity of phospha-Wittig reagents towards NHCs and NHOs

Phospha-Wittig reagents, RPPMe3(R = Mes* 2,4,6-tBu3-C6H2;MesTer 2,6-(2,4,6-Me3C6H2)-C6H3;DipTer 2,6-(2,6-iPr2C6H

Elevated reaction order of 1,3,5-tri-tert-butylbenzene bromination as evidence of a clustered polybromide transition state: a combined kinetic and computational study

The kinetics and mechanism of concurrent bromo-de-protonation and bromo-de-tert-butylation of 1,3,5-tri-tert-butylbenzene at different bromine concentrations were studied experimentally and theoretically. Both reactions have high order in bromine (experimental kinetic orders ～5 and ～7, respectively). According to quantum chemical DFT calculations, such high reaction orders are caused by participation of clustered polybromide anions Br2n?1- in transition states. Bromo-de-tert-butylation has a higher order due to its bigger reaction center demanding clusters of extended size. A significant primary deuterium kinetic isotope effect (KIE) for bromo-de-protonation is measured indicating proton removal is rate limiting, as confirmed by computed DFT models. The latter predict a larger value for the KIE than measured and possible explanations for this are discussed.

Functionalization of P4 using a Lewis acid stabilized bicyclo[1.1.0]tetraphosphabutane anion

Reacting white phosphorus (P4) with sterically encumbered aryl lithium reagents (aryl=2,6-dimesitylphenyl or 2,4,6-tBu3C6H2) and B(C6F5)3 gives the unique, isolable Lewis acid st