Lot numbers can be found on the outside label of a product:
2,9-Dichloro-1,10-phenanthroline
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CAS No. 29176-55-4
- Cat. No. CS-W004583
- Purity≥97%
- MDL No.MFCD02084186
*For research and further manufacturing use only, not for direct human use.
Structure of 29176-55-4
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General Information
- CAS No. 29176-55-4
- Cat. No. CS-W004583
- Purity ≥97%
- MDL No. MFCD02084186
- Storage RT, protect from light, stored under nitrogen
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₂H₆Cl₂N₂
- Molecular Weight 249.09
- Synonym(s) 2,9-Dichloro-1,10-phenthroline
- SMILES ClC=1N=C2C(=CC1)C=CC=3C=CC(Cl)=NC32
Description
2,9-Dichloro-1,10-phenanthroline features two chlorine substituents at the 2 and 9 positions of the phenanthroline scaffold, enhancing electron-withdrawing character and improving metal-chelation stability. This bench-stable ligand integrates readily into coordination complexes for catalytic applications and redox studies.
Application
2,9-Dichloro-1,10-phenanthroline serves as a versatile ligand in transition metal catalysis, particularly in palladium-catalyzed cross-coupling reactions. Its electron-withdrawing dichloro substituents enhance oxidative stability and modulate redox potential, enabling efficient catalytic cycles. The rigid aromatic scaffold provides strong chelation to metal centers, facilitating catalyst formation and improving selectivity in C–C and C–heteroatom bond constructions. This compound exhibits excellent bench stability and is compatible with diverse functional groups, making it a practical choice for synthetic applications requiring robust ligand performance.
Synthesis
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Route1
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29176-54-3 - ~92%
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In-stock
29176-55-4
References
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B.R.A.H.M.S GmbH; HOSHINO, Mikio; YANO, Toshisada; YAMANAKA, Yasukazu Patent: WO2012/124310 A1, 2012 ; Location in patent: Page/Page column 35 ;
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Route2
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39588-59-5 - ~86%
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In-stock
29176-55-4
References
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Annibale, Vincent T.; Batcup, Rhys; Bai, Tao; Hughes, Sarah J.; Song, Datong Organometallics, 2013 , vol. 32, # 21 p. 6511 - 6521
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Route3
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In-stock
7089-68-1 - ~%
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In-stock
29176-55-4
References
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Eggers, Friederike; Luening, Ulrich European Journal of Organic Chemistry, 2009 , # 14 p. 2328 - 2341
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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 25.78
- LogP 4.0898
- H_Acceptors 2
- H_Donors 0
- Rotatable_Bonds 0
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Key Words
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