Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-lambda5-phosphane

Name: Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-lambda5-phosphane
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CAS No. 1169942-85-1
Cat. No. CS-0174591
Molecule weight559.28
Purity≥98%
MDL No.MFCD16294536

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Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-lambda5-phosphane|CS-0174591

Structure of 1169942-85-1

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General Information

CAS No. 1169942-85-1
Cat. No. CS-0174591
Purity ≥98%
MDL No. MFCD16294536
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₁H₃₃BBrO₂P
Molecular Weight 559.28
Synonym(s) Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)phosphorane
SMILES CC1(C)C(C)(C)OB(C2=CC=C(C[P+](C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5)C=C2)O1.[Br-]

Description

Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-λ⁵-phosphane is a sterically shielded phosphine reagent featuring a boronate ester handle for Suzuki-Miyaura coupling. This bench-stable compound integrates readily into cross-coupling workflows, enabling efficient C–C bond formation under mild conditions. The para-boronate group facilitates selective reaction with aryl halides, while the triphenylphosphine scaffold provides robust coordination and enhanced solubility in organic media.

Application

Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-λ⁵-phosphane serves as a versatile boron-containing building block for Suzuki-Miyaura cross-coupling reactions. The tetramethylborolane moiety enables stable storage and efficient coupling with aryl halides under mild conditions. Its triphenylphosphine-borane architecture offers excellent functional group tolerance and facilitates the construction of biaryl scaffolds common in medicinal chemistry and materials science.

Synthesis

Route1
- 603-35-0
- 138500-85-3
- ~97%
- In-stock
  
  1169942-85-1
References
- Morrison, Daniel E.; Issa, Fatiah; Bhadbhade, Mohan; Groebler, Ludwig; Witting, Paul K.; Kassiou, Michael; Rutledge, Peter J.; Rendina, Louis M. Journal of Biological Inorganic Chemistry, 2010 , vol. 15, # 8 p. 1305 - 1318
Route2
- 138500-85-3
- ~91%
- In-stock
  
  1169942-85-1
References
- Das, Bhaskar C.; Zhao, Xiaoping; Tang, Xiang-Ying; Yang, Fajun Bioorganic and Medicinal Chemistry Letters, 2011 , vol. 21, # 18 p. 5638 - 5641

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H315-H319-H335
Precautionary Statements : P261-P264-P271-P280-P302+P352-P304+P340-P362+P364-P405-P501

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Computational Chemistry Data

TPSA 18.46
LogP 6.3255
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 6

Other Classifications

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Key Words

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Bromotriphenyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-lambda5-phosphane

CAS No. 1169942-85-1

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