Lot numbers can be found on the outside label of a product:
2,7-Dibromo-9-hexyl-9H-carbazole
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CAS No. 654676-12-7
- Cat. No. CS-0152140
- Purity≥97%
- MDL No.MFCD29089359
*For research and further manufacturing use only, not for direct human use.
Structure of 654676-12-7
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General Information
- CAS No. 654676-12-7
- Cat. No. CS-0152140
- Purity ≥97%
- MDL No. MFCD29089359
- Storage Store at room temperature
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₈H₁₉Br₂N
- Molecular Weight 409.16
- Synonym(s) 2,7-Dibromo-9-hexylcarbazole
- SMILES CCCCCCN1C2=C(C=CC(=C2)Br)C3=C1C=C(C=C3)Br
Description
2,7-Dibromo-9-hexyl-9H-carbazole features a sterically hindered carbazole core with brominated positions at the 2 and 7 sites, enabling efficient cross-coupling reactions. The hexyl side chain enhances solubility in organic media while maintaining electronic integrity. This derivative serves as a key building block for conjugated polymers and optoelectronic materials, offering high stability under standard processing conditions.
Application
2,7-Dibromo-9-hexyl-9H-carbazole serves as a versatile building block for the synthesis of conjugated materials and functionalized heterocycles. The dibromo substitution at the 2 and 7 positions enables efficient Pd-catalyzed cross-coupling reactions, while the hexyl chain enhances solubility in organic media. This compound functions reliably in standard Suzuki, Stille, or Negishi coupling protocols, facilitating the construction of complex π-conjugated architectures with predictable regiochemistry. Its bench-stable nature and ease of purification support scalable synthesis and integration into advanced material development workflows.
Synthesis
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Route1
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111-25-1 -
In-stock
136630-39-2 - ~87%
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In-stock
654676-12-7
References
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Rong, Lingling; Liu, Qiancai; Tang, Jie; Chi, Zhenguo Heterocycles, 2010 , vol. 81, # 4 p. 977 - 984
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Route2
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In-stock
92-86-4 - ~%
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In-stock
654676-12-7
References
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Ryan, Aoife; Tuffy, Brian; Horn, Sabine; Blau, Werner J.; Senge, Mathias O. Tetrahedron, 2011 , vol. 67, # 43 p. 8248 - 8254
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Route3
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439797-69-0 - ~%
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In-stock
654676-12-7
References
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Kawabata, Kohsuke; Goto, Hiromasa Chemistry - A European Journal, 2012 , vol. 18, # 47 p. 15065 - 15072
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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-P330-P362+P364-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 4.93
- LogP 6.8998
- H_Acceptors 1
- H_Donors 0
- Rotatable_Bonds 5
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Key Words
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