2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

Name: 2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine
Brand: ChemScene
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CAS No. 1003845-08-6
Cat. No. CS-W006099
Purity≥97%
MDL No.MFCD11856048

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2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine|CS-W006099

Structure of 1003845-08-6

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General Information

CAS No. 1003845-08-6
Cat. No. CS-W006099
Purity ≥97%
MDL No. MFCD11856048
Storage -20°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₀H₁₄BClN₂O₂
Molecular Weight 240.49
Synonym(s) 2-Chloropyrimidine-5-boronic Acid Pinacol Ester
SMILES CC1(C)OB(OC1(C)C)C1=CN=C(Cl)N=C1

Description

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine delivers a boronate handle at the pyrimidine C5 position, enabling efficient Suzuki-Miyaura coupling under standard conditions. The tetramethyl-substituted dioxaborolane moiety enhances stability and moisture tolerance, while the chloropyrimidine electrophile supports selective cross-coupling in complex molecular architectures.

Application

2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine serves as a versatile boron-containing building block for palladium-catalyzed cross-coupling reactions. The pyrimidine core provides a stable heterocyclic scaffold with predictable reactivity, while the pinacol boronate group enables efficient coupling with aryl, vinyl, and heteroaryl halides under mild conditions. Bench-stable and readily purified by flash chromatography, it facilitates the construction of complex pharmaceutical intermediates and functionalized heterocycles in high yield.

Synthesis

Route1
- In-stock
  
  76-09-5
- In-stock
  
  1003845-06-4
- ~99%
- In-stock
  
  1003845-08-6
References
- Mogi, Muneto; Yamada, Ken; Yasoshima, Kayo; Kawanami, Toshio; Umemura, Ichiro; Iwaki, Yuki; Qin, Hongbo; Imase, Hidetomo Patent: US2009/118287 A1, 2009 ; Location in patent: Page/Page column 67-68 ;

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
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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Computational Chemistry Data

TPSA 44.24
LogP 1.4292
H_Acceptors 4
H_Donors 0
Rotatable_Bonds 1

Other Classifications

Building Blocks Functional Group Boronic Acid And Its Ester

Building Blocks Skeleton Aromatic heterocycle compounds Pyrimidine compounds

Chemical Biology Pharmaceutical Development and Drug Discovery Research Reagents Building Blocks for Pharmaceutical Ingredients

Chemical Synthesis Organometallic Reagents Organoboron Boronic Acids and Derivatives

Key Words

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2-Chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

CAS No. 1003845-08-6

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