2117-11-5

Basic information

• Product Name: 4-PENTYN-2-OL
• Synonyms: pent-4-yn-2-ol;(R,S)-4-PENTYN-2-OL;4-PENTYN-2-OL, 98+%;4-Pentyn-2-ol, 97+%;1-Pentyne-4-ol;HC≡CCH2CH(OH)CH3;4-Pentyn-2-ol, 97+% 5GR;(+/-)-4-PENTYN-2-OL
• CAS NO: 2117-11-5
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.12
• EINECS: 218-321-1
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives
• Mol File: 2117-11-5.mol

Chemical Properties

• Melting Point: -24.1°C (estimate)
• Boiling Point: 126-127 °C(lit.)
• Flash Point: 99 °F
• Appearance: Clear colorless to pale yellow/Liquid
• Density: 0.892 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.35mmHg at 25°C
• Refractive Index: n20/D 1.438(lit.)
• Storage Temp.: Flammables area
• Solubility: Miscible with chloroform and ethyl acetate.
• PKA: 14.29±0.20(Predicted)
• BRN: 1734245
• CAS DataBase Reference: 4-PENTYN-2-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-PENTYN-2-OL(2117-11-5)
• EPA Substance Registry System: 4-PENTYN-2-OL(2117-11-5)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37/38
• Safety Statements: 26-36
• RIDADR: UN 1987 3/PG 3
• WGK Germany: 3
• F: 10
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 2117-11-5(Hazardous Substances Data)

Usage

Uses

Used in Environmental Studies:
4-Pentyn-2-ol is used as a reference compound in Quantitative Structure-Activity Relationship (QSAR) studies for assessing the toxicity levels of organic compounds in environmental situations. This application aids in understanding the potential hazards and risks associated with the presence of such compounds in the environment.
Used in Chemical Synthesis:
In the field of chemical synthesis, 4-Pentyn-2-ol serves as a key intermediate in the preparation of various complex molecules. It is used in the synthesis of Fischer-type rhenium(III) benzoyldiazenido-2-oxacyclocarbenes, which are important for studying the properties and reactivity of metal complexes. Additionally, 4-Pentyn-2-ol is utilized in the preparation of C-aryl glycosides through a cycloaddition reaction with an aryl nitrile oxide, which is a valuable method for constructing carbohydrate derivatives with potential applications in pharmaceuticals and materials science.

InChI:InChI=1/C5H8O/c1-3-4-5(2)6/h1,5-6H,4H2,2H3

Upstream product

• 75-07-0 acetaldehyde 
• 106-96-7 propargyl bromide 
• 1066-26-8 sodium acetylide 
• 75-56-9 methyloxirane 
• 53143-80-9 (Z)-1-Brommethylen-2-methylcyclopropan 
• 74-86-2 acetylene 
• 70277-75-7 lithium acetylide 
• 75-89-8 2,2,2-trifluoroethanol 
• 70106-30-8 3-methyl-1-cyclobutenyl nonaflate 
• 22665-30-1 allenylzinc bromide 
• 18295-60-8 allenylmagnesium bromide 
• 27611-32-1 4-(3-nitro-benzenesulfonyloxy)-pent-1-yne 
• 18295-60-8 propargyl magnesium bromide 

Downstream Products

• 18482-37-6 1,1-Diphenyl-2-hexin-1,5-diol 
• 10446-64-7 1-<1-Methyl-butin-(3)-yloxy>-1-phenoxy-aethan 
• 141809-09-8 4-<(tert-butyl)diphenylsilyloxy>pent-1-yne 
• 164801-78-9 (+/-)-pent-4'-yn-2'-yl hydrogen phthalate 
• 111957-98-3 Pent-4-en-2-ol 
• 72806-73-6 5-methyl-3-<(E)-phenylmethylidene>dihydrofuran-2(3H)-one 
• 69065-89-0 methyl N-(2-methoxycarbonylphenyl)oxalamate 
• 62873-16-9 5-methyl-3-(methylidene)dihydrofuran-2(5H)-one 

Relevant articles and documents

Formal metal-free γ-arylation of 1,3-dicarbonyl compounds: Via an isomerisation/1,4-addition/[3,3]-sigmatropic rearrangement sequence

A metal-free redox arylation of alkynes with sulfoxides has been developed to provide unconventional access to diverse γ-arylated 1,3-dicarbonyl compounds in an atom-economical manner. Mechanistic studies suggest that a conjugated allenone intermediate was generated in situ, which solves the problem of reactivity and regioselectivity of unsymmetrical dialkyl-substituted internal alkynes and enables the functionalisation of a broad range of substrates bearing electron-withdrawing functional groups. The resulting arylated 1,3-dicarbonyl compounds are versatile and useful building blocks for further functionalisation. This journal is

Regio-Divergent C—H Alkynylation with Janus Directing Strategy via Ir(III) Catalysis

Directing strategy has been extensively exploited to maintain activity and selectivity for the rapid access to functionalized molecules and pharmaceutical targets. However, ‘one-to-one’ activation model was usually achieved through traditional directing strategy. Herein, we achieved ‘one-to-two’ activation model by slight modification of simple and practical ketoxime and amide functionality. With judicious choice of directing groups, Csp3—H and Csp2—H bond alkynylation reaction, and more significantly, dehydrogenative Csp3—H alkynylation, were realized, enabling the regio-divergent late-stage modifications of pharmaceuticals.

Alkyne derivative containing nitrogen-oxygen bond and preparation method and application thereof

The invention belongs to the technical field of organic synthesis, and in particular relates to an alkyne derivative containing a nitrogen-oxygen bond and a preparation method and application thereof.The provided alkyne derivative containing the nitrogen-oxygen bond has a structural formula as shown in a formula (I), wherein R1 and R2 are independently selected from hydrogen, a C1-C20 hydrocarbongroup, a C5-C30 aryl, a C5-C30 substituted aryl, or a C5-C30 aromatic heterocyclic group, and R3 is a substituted silicon group. The alkyne derivative containing the nitrogen-oxygen bond contains aneasily convertible nitrogen-oxygen bond, a primary amine and an alkynyl-containing polysubstituted alcohol compound with high added value can be obtained by reduction, and the derivative has a good application prospect in the field of organic synthesis. Moreover, the alkyne derivative containing the nitrogen-oxygen bond contains a silicon group which is directly linked to an alkyne and can be easily removed, and a terminal alkyne compound can be further obtained.

Synthesis of substituted α-methylene-γ-butyrolactones from chloroformates via palladium catalysed cyclisation-anion capture

Cyclisation of chloroformates onto proximate alkyne functionality in the presence of a Pd(0) catalyst followed by anion capture affords α-methylene-γ-butyrolactone derivatives in moderate to good yields.

A new, highly stereoselective approach to pyrrolidines via overall 5-endo-trig cyclisations of homoallylic tosylamides

Iodocyclisations of E-homoallylic tosylamides 7 lead to excellent yields of either 2,5-trans- or 2,5-cis-3-iodopyrrolidines (10 or 11), depending upon the reaction conditions.

Cumulated Ylides XX. Syntheses of (E)-α,β-Unsaturated Macrocyclic Lactones by Intramolecular Wittig-Olefination via Triphenylphosphoranylideneketene

Two methods for closure of macrocyclic lactone rings by intramolecular Wittig reaction of (ω-oxoalkoxy)carbonylmethylenetriphenylphosphoranes are described.The latter are easily accessible by addition of the appropriate (free or protected) ω-hydroxyalkanals to the cumulated ylide triphenylphosphoranylideneketene.Examples are then given for the use of these methods in natural product synthesis.

NEW STRATEGY IN THE STEREOCONTROLLED SYNTHESIS OF THE SPIRO KETAL SUBUNIT OF MILBEMYCINS

A double Baeyer-Villiger oxidation of bicyclo heptane-2,5-dione and a stereocontrolled alkylation of the dianion derived from 4-pentyn-2-ol are the salient features of a new strategy in the stereocontrolled synthesis of the spiroketal moiety of milbemycins.

Vinyl Cations, 38. Synthesis and Solvolysis of 3-Substituted 1-Cyclobutenyl Nonaflates

3-Methyl- (8a) and 3-cyclopropyl-1-cyclobutenyl nonaflate (8b) as well as 2-cyclopropyl-1-cyclobutenyl nonaflate (12) and the parent 1-cyclobutenyl nonaflate (3) were synthesized from the corresponding cyclobutanones and nonafluorobutanesulfonic anhydride (10).The solvolysis rates and the product compositions of the solvolyses in trifluoroethanol and trifluoroethanol/water mixtures were determined.All 1-cyclobutenyl nonaflates solvolyze via a SN1 mechanism involving the intermediate nonclassical 1-cyclobutenyl cation, which is additionally stabilized by the substituents in the 3-position.