Lot numbers can be found on the outside label of a product:
1,4-Dibromo-2,3,5,6-tetramethylbenzene
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CAS No. 1646-54-4
- Cat. No. CS-0110425
- Purity≥98%
- MDL No.MFCD00017787
*For research and further manufacturing use only, not for direct human use.
Structure of 1646-54-4
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General Information
- CAS No. 1646-54-4
- Cat. No. CS-0110425
- Purity ≥98%
- MDL No. MFCD00017787
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₂Br₂
- Molecular Weight 292.01
- Synonym(s) benzene, 1,4-dibromo-2,3,5,6-tetramethyl-
- SMILES CC1=C(C(C)=C(C(Br)=C1C)C)Br
Description
1,4-Dibromo-2,3,5,6-tetramethylbenzene features a sterically hindered aromatic core with bromine substituents at the para positions, enabling selective cross-coupling reactions. The four methyl groups enhance solubility and stability under standard conditions, while the electron-deficient ring facilitates palladium-catalyzed transformations. This compound serves as a robust building block for functionalized arenes in synthetic organic chemistry.
Application
1,4-Dibromo-2,3,5,6-tetramethylbenzene serves as a versatile dibrominated aromatic building block for the synthesis of functionalized biaryls and heterocycles. Its sterically encumbered structure enhances stability and facilitates selective cross-coupling reactions under standard Pd-catalyzed conditions. The molecule’s defined substitution pattern enables predictable regiochemistry in Suzuki-Miyaura and Stille couplings, while its crystalline form simplifies purification and handling in industrial-scale syntheses.
Synthesis
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Route1
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95-93-2 - ~90%
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In-stock
1646-54-4
References
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Miller, Glen P.; Kaur, Irvinder Patent: US2011/130593 A1, 2011 ; Location in patent: Page/Page column 6 ;
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Route2
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95-93-2
- ~5%
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In-stock
1646-54-4
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In-stock
1646-53-3
References
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Podgorsek, Ajda; Stavber, Stojan; Zupan, Marko; Iskra, Jernej Tetrahedron, 2009 , vol. 65, # 22 p. 4429 - 4439
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Route3
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In-stock
1646-53-3
- ~%
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In-stock
1646-54-4
References
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Smith; Moyle Journal of the American Chemical Society, 1933 , vol. 55, p. 1676,1681
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 0
- LogP 4.44528
- H_Acceptors 0
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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