3,5-Diethynylpyridine

Name: 3,5-Diethynylpyridine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 67227-90-1
Cat. No. CS-0322669
Molecule weight127.14
Purity≥98%
MDL No.None

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
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Structure of 67227-90-1

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General Information

CAS No. 67227-90-1
Cat. No. CS-0322669
Purity ≥98%
MDL No. None
Storage 4°C, stored under nitrogen
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₉H₅N
Molecular Weight 127.14
Synonym(s) Pyridine, 3,5-diethynyl- (9CI)
SMILES C#CC1=CC(=CN=C1)C#C

Description

3,5-Diethynylpyridine features a pyridine core flanked by two ethynyl groups at the 3 and 5 positions, creating a rigid, electron-deficient scaffold ideal for conjugated systems. This geometry enables efficient integration into π-conjugated architectures, facilitating applications in organic electronics and transition-metal-catalyzed coupling reactions. The molecule exhibits excellent stability under standard conditions, allowing straightforward handling and incorporation into complex molecular designs.

Application

3,5-Diethynylpyridine serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling the construction of conjugated heteroaromatic systems. Its two terminal alkyne groups exhibit high reactivity in Sonogashira and Glaser-type couplings, facilitating the assembly of extended π-conjugated scaffolds. The pyridine core provides orthogonal functionality for further derivatization, while the compound demonstrates excellent bench stability and ease of purification, making it well-suited for applications in materials chemistry and medicinal chemistry synthesis.

Synthesis

Route1
- In-stock
  
  625-92-3
- ~%
- In-stock
  
  67227-90-1
References
- Kijima, Masashi; Oda, Takayuki; Yamazaki, Takahisa; Tazaki, Yasunori; Nakamura, Junji Chemistry Letters, 2006 , vol. 35, # 8 p. 844 - 845
Route2
- 66912-21-8
- ~%
- In-stock
  
  67227-90-1
References
- Ng, Siu Choon; Novak, Igor; You, Xiaomei; Huang, Wei Journal of Physical Chemistry A, 1998 , vol. 102, # 6 p. 904 - 908

Safety Information

Download SDS

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+P364

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Computational Chemistry Data

TPSA 12.89
LogP 1.0442
H_Acceptors 1
H_Donors 0
Rotatable_Bonds 0

Other Classifications

Building Blocks Skeleton Aromatic heterocycle compounds Pyridine compounds

Life Science Click Chemistry Reagents Alkyne

Chemical Biology Pharmaceutical Development and Drug Discovery Research Conjugation Chemistry/Click Chemistry Terminal Alkynes

Chemical Biology Conjugation Chemistry/Click Chemistry Terminal Alkynes

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3,5-Diethynylpyridine

CAS No. 67227-90-1

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