10602-03-6

Basic information

• Product Name: Ethyl 4-Ethynylbenzoate
• Synonyms: Ethyl 4-Ethynylbenzoate;4-Ethynyl-benzoic acid ethyl ester;(p-Ethoxycarbonylphenyl)acetylene;4-(Ethoxycarbonyl)phenylacetylene;Ethyl 4-Ethynylbenzoate(WX686207)
• CAS NO: 10602-03-6
• Molecular Formula: C₁₁H₁₀O₂
• Molecular Weight: 174.1959
• Mol File: 10602-03-6.mol
• Article Data: 36

Chemical Properties

• Melting Point: 28 °C
• Boiling Point: 257.092 °C at 760 mmHg
• Flash Point: 100.987 °C
• Appearance: /
• Density: 1.088 g/cm³
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Ethyl 4-Ethynylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 4-Ethynylbenzoate(10602-03-6)
• EPA Substance Registry System: Ethyl 4-Ethynylbenzoate(10602-03-6)

Safety Data

• Hazardous Substances Data: 10602-03-6(Hazardous Substances Data)

Usage

General Description

Ethyl 4-Ethynylbenzoate, also known as ethyl 4-ethynylbenzoate, is a chemical compound with the molecular formula C11H10O2. It is a colorless liquid with a fruity odor, commonly used as an intermediate in organic synthesis for the production of pharmaceuticals, dyes, and perfumes. Ethyl 4-Ethynylbenzoate is also used as a building block in the production of liquid crystals and is a potential building block for the synthesis of new organic materials. It is important to handle this chemical with care as it is a flammable liquid and can cause skin and eye irritation upon contact. Overall, Ethyl 4-Ethynylbenzoate is a versatile chemical compound with various industrial applications.

Upstream product

• 6929-96-0 2-ethynyl-1,3-butadiene 
• 623-47-2 propynoic acid ethyl ester 
• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 7681-65-4 copper(I) iodide 
• 1066-54-2 trimethylsilylacetylene 
• 94-09-7 p-aminoethylbenzoate 
• 994-89-8 tributylethynyltin 
• 348-06-1 p-carboethoxybenzenediazonium tetrafluoroborate 
• 1829-28-3 ethyl 2-iodobenzoate 
• 110166-76-2 ethyl 2-((trimethylsilyl)ethynyl)benzoate 
• 64-17-5 ethanol 
• 10602-00-3 4-Ethynyl-benzoic acid 
• 75867-41-3 4-trimethylsilanylethynyl-benzoic acid methyl ester 
• 619-44-3 methyl 4-iodobenzoate 

Downstream Products

• 10602-00-3 4-Ethynyl-benzoic acid 
• 10602-04-7 (4-ethynylphenyl)methanol 
• 174665-68-0 ethyl 4-[2-(2-aminopyridin-6-yl)ethynyl]benzoate 
• 107099-30-9 (E)-4-(2-trimethylsilanylvinyl)benzoic acid ethyl ester 
• 801240-15-3 4-(6-methylamino-pyridin-2-ylethynyl)-benzoic acid ethyl ester 
• 801240-17-5 4-[6-(3-{2-[2-(3-tert-butoxycarbonylamino-propoxy)-ethoxy]-ethoxy}-propylamino)-pyridin-2-ylethynyl]-benzoic acid ethyl ester 
• 1198362-01-4 1,3,6,8-tetrakis[(4-ethoxycarbonylphenyl)ethynyl]pyrene 
• 1214264-94-4 (E)-ethyl 4-(2-(1H-naphtho[1,8-de][1,3,2]diazaborinin-2(3H)-yl)-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)vinyl)benzoate 
• 1208365-08-5 ethyl 4-(2-(perfluorophenyl)ethynyl)benzoate 
• 1240327-33-6 (Z)-1-bromo-2-(4-ethoxycarbonylphenyl)-1,4-pentadiene 
• 1240327-19-8 (E)-1-bromo-2-(4-ethoxycarbonylphenyl)-1,4-pentadiene 
• 1352821-32-9 C₅₇H₄₂O₆ 
• 1378514-05-6 ethyl 4-(3-(diethoxyphosphoryl)-3,3-difluoroprop-1-ynyl)benzoate 
• 1383380-47-9 ethyl 4-(1-benzyl-1H-1,2,3-triazol-4-yl)benzoate 

Relevant articles and documents

Discotic material hexakis(4-carboxyphenylethynyl)benzene inhibits Escherichia coli growth via the glycolysis pathway

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Tunable electron acceptors based on cyclopenta[hi]aceanthrylenes

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From Propargylic Alcohols to Substituted Thiochromenes: Gem-Disubstituent Effect in Intramolecular Alkyne Iodo/hydroarylation

This work describes the 6-endo-dig cyclization of S-aryl propargyl sulfides to afford 2H-thiochromenes. The substitution at the propargylic position plays a crucial role in allowing intramolecular silver-catalyzed alkyne hydroarylation and N-iodosuccinimide-promoted iodoarylation. Additionally, a PTSA-catalyzed thiolation reaction of propargylic alcohols was developed to synthesize the required tertiary S-aryl propargyl ethers. The applicability of merging these two methods is demonstrated by synthesizing the retinoic acid receptor antagonist AGN194310.

Preparation and Reactions of Mono- and Bis-Pivaloyloxyzinc Acetylides

Mono-pivaloyloxyzinc acetylide and bis-pivaloyloxyzinc acetylide were selectively prepared from ethynylmagnesium bromide in quantitative yields. These zinc reagents readily underwent Negishi cross-couplings with (hetero)aryl iodides or bromides as well as subsequent Sonogashira cross-couplings. 1,3-Dipolar cycloadditions of these zinc acetylides with benzylic azides produced zincated and bis-zincated triazoles which were trapped with several electrophiles. An opposite regioselectivity compared to the Cu-catalyzed click-reactions was observed.

Iodonium Cation-Pool Electrolysis for the Three-Component Synthesis of 1,3-Oxazoles

The synthesis of 1,3-oxazoles from symmetrical and unsymmetrical alkynes was realized by an iodonium cation-pool electrolysis of I2 in acetonitrile with a well-defined water content. Mechanistic investigations suggest that the alkyne reacts with the acetonitrile-stabilized I+ ions, followed by a Ritter-type reaction of the solvent to a nitrilium ion, which is then attacked by water. The ring closure to the 1,3-oxazoles released molecular iodine, which was visible by the naked eye. Also, some unsymmetrical internal alkynes were tested and a regioselective formation of a single isomer was determined by two-dimensional NMR experiments.