(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

Name: (R)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile
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CAS No. 1146629-84-6
Cat. No. CS-0003923
Purity≥95%
MDL No.MFCD16038968

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(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile|CS-0003923

Structure of 1146629-84-6

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General Information

CAS No. 1146629-84-6
Cat. No. CS-0003923
Purity ≥95%
MDL No. MFCD16038968
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₇H₂₆BN₃O₂
Molecular Weight 315.22
Synonym(s) 3-cyclopentyl-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propanenitrile
SMILES N#CC[C@H](C1CCCC1)N(N=C2)C=C2B(OC(C)3C)OC3(C)C

Description

(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile features a chiral nitrile-bearing scaffold paired with a boronate ester handle, enabling efficient Suzuki-Miyaura cross-coupling. The cyclopentyl group imparts steric bulk and enhanced metabolic stability, while the tetramethyl-substituted dioxaborolane ensures excellent shelf life and moisture tolerance under standard conditions. This compound serves as a key building block for bioactive heterocycles in medicinal chemistry.

Application

(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile serves as a versatile boronate building block for Suzuki-Miyaura cross-coupling reactions. The pyrazole-boronate moiety enables efficient C–C bond formation under mild conditions, while the chiral nitrile-bearing cyclopentyl group provides structural rigidity and functional handle diversity. Bench-stable and compatible with diverse reaction conditions, it facilitates the construction of complex heterocyclic scaffolds in medicinal chemistry and process development workflows.

Synthesis

Route1
- In-stock
  
  1146629-83-5
- In-stock
  
  73183-34-3
- ~%
- In-stock
  
  1146629-84-6
References
- Organic Letters, , vol. 11, # 9 p. 1999 - 2002
Route2
- In-stock
  
  1153949-38-2
- ~%
- In-stock
  
  1146629-84-6
- 1236033-24-1
References
- US2010/190981 A1, ; Page/Page column 91-92 ; US 20100190981 A1

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
Precautionary Statements : P264-P280-P302+P352-P362

Quality Control

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Computational Chemistry Data

TPSA 60.07
LogP 2.82728
H_Acceptors 5
H_Donors 0
Rotatable_Bonds 4

Other Classifications

Building Blocks Functional Group Cyanide/Nitrile

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic heterocycle compounds Pyrazole compounds

Building Blocks Skeleton Fatty ring compounds Cyclopentane compounds

Key Words

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(R)-3-cyclopentyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propanenitrile

CAS No. 1146629-84-6

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