6089-09-4

Basic information

• Product Name: 4-PENTYNOIC ACID
• Synonyms: Pent-4-yn-1-oic acid;pent-4-yn-1-oicacid;4-PENTYNOIC ACID;PROPARGYLACETIC ACID;TIMTEC-BB SBB009121;4-Pentynoicacid,98%;Pentane-4-ynoic acid;4-Pentynoic acid ,95%
• CAS NO: 6089-09-4
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.1
• EINECS: 228-028-0
• Product Categories: Aliphatics;Intermediates & Fine Chemicals;Pharmaceuticals;Building Blocks;C1 to C5;Carbonyl Compounds;Carboxylic Acids;Chemical Synthesis;Organic Building Blocks
• Mol File: 6089-09-4.mol
• Article Data: 34

Chemical Properties

• Melting Point: 54-57 °C(lit.)
• Boiling Point: 110 °C30 mm Hg(lit.)
• Flash Point: 75 °C
• Appearance: White to beige/Crystalline Powder or Flakes
• Density: 1.1133 (rough estimate)
• Vapor Pressure: 0.146mmHg at 25°C
• Refractive Index: 1.3930 (estimate)
• Storage Temp.: 2-8°C
• PKA: 4.30±0.10(Predicted)
• Water Solubility: Soluble in low polarity organic solvents. Soluble in water.
• Sensitive: Light & Air Sensitive & Hygrosco
• BRN: 1742047
• CAS DataBase Reference: 4-PENTYNOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PENTYNOIC ACID(6089-09-4)
• EPA Substance Registry System: 4-PENTYNOIC ACID(6089-09-4)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• RTECS: SC4751000
• F: 8-10-23
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 6089-09-4(Hazardous Substances Data)

Usage

Description

4-Pentynoic acid, also known as but-4-yn-1-oic acid, is a versatile organic compound characterized by its unique structure that features a butynyl group and a carboxylic acid functional group. It is a white to beige crystalline powder or flakes, which undergoes copper-catalyzed intramolecular cyclizations to form enol lactones. Additionally, it reacts with 1-bromo-1-alkynes in the presence of a Pd catalyst to yield biologically active ynenol lactones.

Uses

4-Pentynoic acid is used as a hypoglycemic agent for its ability to increase liver tyrosine aminotransferase and plasma corticosterone while decreasing blood sugar in rats.
Used in Pharmaceutical Industry:
4-Pentynoic acid is used as a building block for the synthesis of a library of eight sequence-defined model oligomers, which are essential in the development of novel pharmaceutical compounds.
Used in Chemical Synthesis:
4-Pentynoic acid is used as a key component in the one-pot synthesis of complex polycyclic heterocycles, such as benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazolinone derivatives, which have potential applications in various fields, including pharmaceuticals and materials science.
Used in Organic Chemistry:
4-Pentynoic acid is utilized in the synthesis of various allenenols lactones, such as [5(E)-(2-allenylidene)-tetrahydro-2-furanones], which are valuable intermediates in organic chemistry and can be used to create a wide range of chemical compounds.
Used in Cancer Research:
4-Pentynoic acid is employed in the synthesis of a cytotoxic macrolide through ring-closing metathesis of a bis acetylene, which has potential applications in cancer research and the development of novel anticancer drugs.

InChI:InChI=1/C5H6O2/c1-2-3-4-5(6)7/h1H,3-4H2,(H,6,7)/p-1

Synthetic route

pent-1-yn-5-ol (5390-04-5) → 4-pentynoic acid (6089-09-4)

Conditions	Yield
With Jones reagent In acetone at 20℃; for 1h;	99%
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%
With Jones reagent In acetone at 0 - 20℃; for 1h;	82%

Upstream product

• 98198-39-1 prop-2-yn-1-ylpropanedioic acid 
• 5390-04-5 pent-1-yn-5-ol 
• 17920-23-9 diethyl propargylmalonate 
• 106-96-7 propargyl bromide 
• 105-53-3 diethyl malonate 
• 15719-64-9 methylammonium carbonate 
• 1007476-32-5 sodium ethyl acetylacetate enolate 
• 1431618-30-2 2-oxohex-5-ynal 
• 18498-59-4 4-pentyn-1-al 
• 21565-82-2 methyl pent-4-ynoate 
• 24342-04-9 methyl pent-2-ynoate 
• 128545-15-3 5-trimethylsilyl-pent-5-yn-1-oic acid 
• 591-80-0 pent-4-enoic acid 
• 78181-02-9 4,5-dibromopentanoic acid 

Downstream Products

• 21565-82-2 methyl pent-4-ynoate 
• 91909-52-3 7-cyclohex-1-enyl-hepta-4,6-diynoic acid 
• 591-12-8 5-methyl-2-furanone 
• 21651-12-7 (E)-2,4-pentadienoic acid 
• 92379-01-6 7-phenylheptane-4,6-diynoic acid 
• 10008-73-8 5-methylenedihydrofuran-2-one 
• 1487-57-6 4,5-Dihydro-5-methoxy-5-methylfuran-2(3H)-one 
• 16900-59-7 4-decynoic acid 
• 137742-28-0 5(E)-<(4-Acetylphenyl)methylidene>tetrahydrofuran-2-one 
• 103437-70-3 5(E)-(3-phenylprop-2-ynylidene)tetrahydro-2-furanone 
• 41143-12-8 hex-4-ynoic acid 
• 591-80-0 pent-4-enoic acid 
• 128545-15-3 5-trimethylsilyl-pent-5-yn-1-oic acid 
• 264619-96-7 N¹-benzyl-N¹⁰-(pent-4-ynoyl)tryptamine 

Relevant articles and documents

Iron(III) Nitrate/TEMPO-Catalyzed Aerobic Alcohol Oxidation: Distinguishing between Serial versus Integrated Redox Cooperativity

Aerobic alcohol oxidations catalyzed by transition metal salts and aminoxyls are prominent examples of cooperative catalysis. Cu/aminoxyl catalysts have been studied previously and feature "integrated cooperativity", in which CuII and the aminoxyl participate together to mediate alcohol oxidation. Here we investigate a complementary Fe/aminoxyl catalyst system and provide evidence for "serial cooperativity", involving a redox cascade wherein the alcohol is oxidized by an in situ-generated oxoammonium species, which is directly detected in the catalytic reaction mixture by cyclic step chronoamperometry. The mechanistic difference between the Cu- and Fe-based catalysts arises from the use iron(III) nitrate, which initiates a NOx-based redox cycle for oxidation of aminoxyl/hydroxylamine to oxoammonium. The different mechanisms for the Cu- and Fe-based catalyst systems are manifested in different alcohol oxidation chemoselectivity and functional group compatibility.

Synthesis of Two Stereoisomers of Potentially Bioactive 13,19,20-Trihydroxy Derivative of Docosahexaenoic Acid

The C16-C22 fragment with the acetylene terminus was constructed through the asymmetric dihydroxylation of the corresponding olefin, while the 15-iodo-olefin corresponding to the C11-C15 part was prepared via the asymmetric transfer hydrogenation of the corresponding acetylene ketone followed by hydrozirconation/iodination. Both pieces were joined by a Sonogashira coupling, and the product was further converted into the title compound via a Wittig reaction with the remaining C1-C10 segment and Boland reduction using Zn with TMSCl.

An Efficient Aerobic Oxidation Protocol of Aldehydes to Carboxylic Acids in Water Catalyzed by an Inorganic-Ligand-Supported Copper Catalyst

A method for the aerobic oxidation of aldehydes to carboxylic acids in water by using an inorganic-ligand-supported copper catalyst was developed. This method was performed with the use of atmospheric oxygen as the sole oxidant under extremely mild aqueous conditions, and furthermore, a wide range of aldehydes with various functional groups were tolerated. The copper catalyst could be recycled and used in successive reactions at least six times without any appreciable degradation in performance. This method is operationally simple and avoids the use of high-costing, toxic, air/moisture-sensitive, and commercially unavailable organic ligands. The generality of this method gives it potential to be used on the industrial scale.