91-06-5

Basic information

• Product Name: 1-BROMO-2,4,6-TRIETHYLBENZENE
• Synonyms: 1-BROMO-2,4,6-TRIETHYLBENZENE;2-bromo-1,3,5-triethylbenzene;2,4,6-Triethylphenyl bromide
• CAS NO: 91-06-5
• Molecular Formula: C12H17Br
• Molecular Weight: 241.17
• EINECS: 202-038-5
• Mol File: 91-06-5.mol

Chemical Properties

• Boiling Point: 276.4±9.0℃ (760 Torr)
• Flash Point: 117.9±13.1℃
• Appearance: /
• Density: 1.181±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.00809mmHg at 25°C
• Refractive Index: 1.5366 (589.3 nm 20℃)
• CAS DataBase Reference: 1-BROMO-2,4,6-TRIETHYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,4,6-TRIETHYLBENZENE(91-06-5)
• EPA Substance Registry System: 1-BROMO-2,4,6-TRIETHYLBENZENE(91-06-5)

Safety Data

• Hazardous Substances Data: 91-06-5(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
1-Bromo-2,4,6-triethylbenzene is used as a building block for the synthesis of more complex organic molecules, serving as a key intermediate in the production of various industrial chemicals and pharmaceuticals. Its unique structure and reactivity make it a versatile component in organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 1-Bromo-2,4,6-triethylbenzene is used as a starting material for the development of new drugs. Its properties allow for the creation of novel compounds with potential therapeutic applications.
Used in Chemical Research:
1-Bromo-2,4,6-triethylbenzene is employed as a reagent in chemical research, where its unique structure and reactivity are studied to understand and develop new chemical reactions and processes.

InChI:InChI=1/C12H17Br/c1-4-9-7-10(5-2)12(13)11(6-3)8-9/h7-8H,4-6H2,1-3H3

Upstream product

• 71-43-2 benzene 
• 102-25-0 1,3,5-triethylbenzene 

Downstream Products

• 58443-78-0 1-(2,4,6-Triaethylphenyl)-2-propanon 
• 200354-88-7 N,N-diisopropyl-2,4,6-triethylbenzamide 
• 123372-73-6 2,4,6-triethyl-benzonitrile 
• 860537-61-7 1-(2,4,6-triethyl-3-bromo-phenyl)-ethanone 
• 351074-02-7 2,4,6-triethylphenyllithium 
• 108593-75-5 dihydroxy(2,4,6-triethylphenyl)borane 
• 1542166-83-5 platinum(II) 5,10,15,20-tetrakis[2,4,6-triethylphenyl]-21H,23H-porphyrin 
• 16688-89-4 2,4,6-triethylbenzaldehyde 
• 1363568-75-5 C₁₇H₂₆Si 
• 1363568-70-0 C₂₆H₃₄ 
• 1363568-71-1 C₂₉H₄₀ 
• 1363568-65-3 1,3,5-triethyl-2-[(2,4,6-trimethylphenyl)ethynyl]benzene 
• 1363568-60-8 C₂₂H₂₆ 
• 133745-00-3 C₃₁H₄₉PSi 

Relevant articles and documents

Highly Chemo-, Regio- and E/Z-Selective Intermolecular Heck-Type Dearomative [2 + 2 + 1] Spiroannulation of Alkyl Bromoarenes with Internal Alkynes

Described herein is a palladium-catalyzed dearomative annulation of alkyl bromoarenes with internal alkynes. Challenges in this spiroannulation include the chemoselectivity among [2 + 2 + 1], [2 + 2 + 2], and [3 + 2] annulations and the E/Z-selectivity associated with the generated exocyclic double bond. In the presence of Pd(OAc)2 and a phosphine ligand, a variety of highly functionalized spirocyclopentadienes with an exocyclic carbon-carbon double bond are provided in good to excellent yields with high chemo-, regio-, and E/Z-selectivity via a Heck-type pathway.

Carbocation Catalyzed Bromination of Alkyl Arenes, a Chemoselective sp3 vs. sp2 C?H functionalization.

The versatility of the trityl cation (TrBF4) as a highly efficient Lewis acid organocatalyst is demonstrated in a light induced benzylic brominaion of alkyl-arenes under mild conditions. The reaction was conducted at ambient temperature under common hood light (55 W fluorescent light) with catalyst loadings down to 2.0 mol% using N-bromosuccinimide (NBS) as the brominating agent. The protocol is applicable to an extensive number of substrates to give benzyl bromides in good to excellent yields. In contrast to most previously reported strategies, this protocol does not require any radical initiator or extensive heating. For electron-rich alkyl-arenes, the trityl ion catalyzed bromination could be easily switched between benzylic sp3 C?H functionalization and arene sp2 C?H functionalization by simply alternating the solvent. This chemoselective switch allows for high substrate control and easy preparation of benzyl bromides and bromoarenes, respectively. The chemoselective switch was also applied in a one-pot reaction of 1-methylnaphthalene for direct introduction of both sp3 C?Br and sp2 C?Br functionality. (Figure presented.).

Protecting the triplet excited state in sterically congested platinum porphyrin

Platinum tetrakis(2,4,6-triethylphenyl)porphyrin (Pt-1) was synthesized and its structural (X-ray), electrochemical and photophysical properties were fully characterized. Comparative studies of Pt-1 and its unsubstituted analog PtTPP show the effect of sterically congesting ortho-substituents on the dynamics of the triplet excited states. Lowered quenching rates by 3-4 times were observed for Pt-1vs. PtTPP in the presence of oxygen and perylene, and in concentration (self)-quenching experiments.

Atroposelectivity in the electrophilic substitution reactions of laterally lithiated and silylated tertiary amides

Lateral lithiation-electrophilic quench of 2-alkyl-1-naphthamides and 2,6-dialkylbenzamides yields products containing an atropisomeric Ar-CO axis and a new stereogenic centre with high (generally >95:5) diastereo-selectivity. With imines as electrophiles, single diastereoisomers containing an atropisomeric axis and two new stereogenic centres are formed. 2,6-Dialkylbenzamides may be functionalised stereoselectively at both the 2- and 6-positions, leading (with imines) to symmetrical compounds bearing 1,7-related stereogenic centres. 2-Alkylbenzamides with only one ortho alkyl group are not atropisomeric at ambient temperature but are functionalised diastereoselectively by lateral lithiation-electrophilic quench at - 78°C. Stabilisation of the atropisomeric products by further lithiation and alkylation proves their diastereoselective formation. The lack of stereospecificity in the fluoride-promoted reaction of a laterally silylated 1-naphthamide with an aldehyde suggests that reported reactions of laterally silylated benzamides may also be controlled by the rotationally restricted amide group.

Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.

The First Reversible Thermal Dissociation of Distannanes, R3Sn-SnR3, Giving Stannyl Radicals, R3Sn.

Thermal and reversible dissociation of organic distannanes, R3Sn-SnR3 (1) * 2 R3Sn. (2), have been found for the first time when a sufficient strain in 1 was generated by bulky substituents.For this, the residues R = phenyl, cyclohexyl, 1-adamantyl are not sufficient up to 230 deg C, but with R = 2,4,6-trialkylphenyl the dissociation temperature (ESR) is lowered to 20 deg C in the series alkyl = Me, Et, iPr.The ESR spectra of stannyl radicals 2 as well as $vSn-Sn(sym.) , δHDiss., and EA values for 1 are reported.New distannanes 1 and corresponding compounds R3SnBr and R3SnH are described.