Ethyl 4-ethynylbenzoate

Name: Ethyl 4-ethynylbenzoate
Brand: ChemScene
Availability: InStock
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CAS No. 10602-03-6
Cat. No. CS-D0535
Purity≥98%
MDL No.MFCD00168821

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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+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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Structure of 10602-03-6

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General Information

CAS No. 10602-03-6
Cat. No. CS-D0535
Purity ≥98%
MDL No. MFCD00168821
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₁₁H₁₀O₂
Molecular Weight 174.20
Synonym(s) Ethyl 4-Ethynylbenzoate(WX686207)
SMILES CCOC(C1=CC=C(C#C)C=C1)=O

Description

Ethyl 4-ethynylbenzoate features a terminal alkyne group conjugated to an ester-functionalized aromatic ring, enabling efficient copper-catalyzed azide-alkyne cycloaddition (CuAAC) for bioconjugation and materials synthesis. This bench-stable reagent integrates readily into click chemistry workflows, offering high functional group tolerance and predictable regioselectivity.

Application

Ethyl 4-ethynylbenzoate serves as a versatile building block in transition-metal-catalyzed coupling reactions, enabling efficient access to conjugated enynes and functionalized aryl alkynes. The terminal alkyne group exhibits high reactivity in Sonogashira, Glaser, and Cadiot-Chodkiewicz couplings, while the ester functionality provides compatibility with standard synthetic manipulations. Bench-stable and readily purified by column chromatography, it functions effectively in both small-molecule synthesis and heterocycle construction workflows.

Synthesis

Route1
- 150969-54-3
- ~92%
- In-stock
  
  10602-03-6
References
- Schaate, Andreas; Roy, Pascal; Preusse, Thomas; Lohmeier, Sven Jare; Godt, Adelheid; Behrens, Peter Chemistry - A European Journal, 2011 , vol. 17, # 34 p. 9320 - 9325
Route2
- In-stock
  
  51934-41-9
- ~%
- In-stock
  
  10602-03-6
References
- Tetrahedron Letters, , vol. 45, # 8 p. 1693 - 1697
Route3
- In-stock
  
  51934-41-9
- In-stock
  
  7681-65-4
- 1066-54-2
- ~%
- In-stock
  
  10602-03-6
References
- US2002/120006 A1, ; US 20020120006 A1

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

Quality Control

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Computational Chemistry Data

TPSA 26.3
LogP 1.8446
H_Acceptors 2
H_Donors 0
Rotatable_Bonds 2

Other Classifications

Building Blocks Functional Group Alkyne

Building Blocks Functional Group Ester

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Conjugation Chemistry/Click Chemistry Terminal Alkynes

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

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Ethyl 4-ethynylbenzoate

CAS No. 10602-03-6

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