10229-10-4

Basic information

• Product Name: 3-PENTYN-1-OL
• Synonyms: 3-PENTYN-1-OL;pent-3-yn-1-ol;3-PENTYN-1-OL 99%;3-PENTYN-1-OL 99+%;3-Pentyn-1-ol, 99% 5GR
• CAS NO: 10229-10-4
• Molecular Formula: C₅H₈O
• Molecular Weight: 84.12
• EINECS: 233-550-7
• Product Categories: Acetylenes;Acetylenic Alcohols & Their Derivatives;Alkynes;Internal;Organic Building Blocks
• Mol File: 10229-10-4.mol

Chemical Properties

• Melting Point: -24.1°C (estimate)
• Boiling Point: 154-157 °C(lit.)
• Flash Point: 130 °F
• Appearance: clear yellow liquid
• Density: 0.912 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.04mmHg at 25°C
• Refractive Index: n20/D 1.456(lit.)
• Storage Temp.: 2-8°C
• PKA: 14.39±0.10(Predicted)
• BRN: 1735967
• CAS DataBase Reference: 3-PENTYN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-PENTYN-1-OL(10229-10-4)
• EPA Substance Registry System: 3-PENTYN-1-OL(10229-10-4)

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
• TSCA: Yes
• HazardClass: 3.2
• PackingGroup: III
• Hazardous Substances Data: 10229-10-4(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Pentyn-1-ol is utilized as a key intermediate in the synthesis of various organic compounds. One notable example is its use in the synthesis of 4,4-bis(1-methyl-1H-indol-3-yl)pentan-1-ol, a compound that may have potential applications in pharmaceutical or chemical research.
Used in Corrosion Inhibition:
The inhibiting effect of 3-pentyn-1-ol on the corrosion of iron in 1M HCl has been investigated, demonstrating its potential use as a corrosion inhibitor. This application could be particularly valuable in industries where metal corrosion is a significant concern, such as in the manufacturing, construction, and automotive sectors.
Used in Coordination Chemistry:
3-Pentyn-1-ol has been found to react with Fe3(CO)12 in CH3OH/KOH solution, yielding a closed trinuclear hydridic complex (μ-H)Fe3(CO)9(μ3-η3-[H3CCC(CH2)(CH2)CO]). This reaction highlights the compound's potential use in coordination chemistry, where it can be employed to form novel complexes with interesting properties and potential applications in various fields, such as catalysis or materials science.

InChI:InChI=1/C5H8O/c1-2-3-4-5-6/h6H,4-5H2,1H3

Upstream product

• 64-17-5 ethanol 
• 54106-83-1 pent-3-ynyl triflate 
• 50596-94-6 4-chloro-5-methyl-2,3-dihydro-furan 
• 75-21-8 oxirane 
• 74-83-9 methyl bromide 
• 74-86-2 acetylene 
• 39161-19-8 pent-3-en-1-ol 
• 20518-51-8 2-chloropent-2-en-5-ol 
• 10486-71-2 sodium propynide 
• 16466-97-0 1-propynylmagnesium bromide 
• 61362-77-4 5-[tert-butyldimethylsilyloxy]pent-1-yne 
• 5390-04-5 pent-1-yn-5-ol 
• 76782-82-6 tert-Butyldimethyl(prop-2-ynyloxy)silane 
• 75-07-0 acetaldehyde 

Downstream Products

• 3329-88-2 pent-3-yn-1-yl 4-methylbenzenesulfonate 
• 62108-18-3 5-methoxypent-2-yne 
• 113490-30-5 3-ethynyl-2-methyl-6-oxacyclohex-2-en-1-one 
• 113490-39-4 25-hydroxy-3-deoxy-2-oxavitamin D₃ 
• 113490-37-2 2-nor-1,3-seco-1,25-dihydroxyvitamin D₃ 
• 208332-05-2 3,4-Dimethoxy-1-[1-(pent-3-ynyloxyl)ethyl]benzene 
• 1403381-43-0 1-methoxy-4-[(pent-3-yn-1-yloxy)methyl]benzene 
• 1403381-44-1 3-{2-[(4-methoxyphenyl)methoxy]ethyl}-2-methyl-4-phenyl-5,6,7,8-tetrahydroquinoline 
• 1403381-45-2 2-(2-methyl-4-phenyl-5,6,7,8-tetrahydroquinolin-3-yl)ethan-1-ol 
• 1403381-46-3 methyl 2-(2-methyl-4-phenyl-5,6,7,8-tetrahydroquinolin-3-yl)acetate 
• 126459-30-1 (4S)-2-oxo-3-(9-phenylfluoren-9-yl)-4-(1'-oxo-4'-hexynyl)oxazolidine 
• 126459-33-4 (4S,4'E)-2-oxo-3-(9-phenylfluoren-9-yl)-4-(1'-oxo-4'-hexenyl)oxazolidine 
• 126459-32-3 (4S)-3-(9-phenylfluoren-9-yl)-4-(1'-oxo-4'-hexynyl)oxazolidine 
• 112292-85-0 (Z)-2-Benzyl-3-oxo-non-7-enoic acid ethyl ester 

Related news

Reactions of Fe3(CO)12 with 2-methyl-3-butyn-1-ol and 3-PENTYN-1-OL (cas 10229-10-4) under basic methanolic conditions: The crystal structures of Fe2(CO)6(μ-CO)(μ-η2-[HCC{C(CH3)2}C(O)(OCH3)]) and of (μ-H)Fe3(CO)9(μ3-η3-[H3CCC(CH2)(CH2)CO])07/25/2019

The reactions of Fe3(CO)12 with 2-methyl-3-butyn-2-ol and 3-pentyn-1-ol in CH3OH/KOH solution lead, respectively, to the binuclear complex Fe2(CO)6(μ-CO)(μ-η2-[HCC{C(CH3)2}C(O)(OCH3)]) (as the main product) and to the closed trinuclear hydridic complex (μ-H)Fe3(CO)9(μ3-η3-[H3CCC(CH2)(CH2)C...detailed

Relevant articles and documents

Platinum-catalyzed multistep reactions of indoles with alkynyl alcohols

PtCl2 effectively catalyzes the multistep reaction of N-methyl indole (1a) with pent-3-yn-1-ol (2a) in THF at room temperature for 2 h to give indole derivative 3a, which contains a five-membered cyclic ether group at C3 in 93 % yield. Under similar reaction conditions, various substituted N-methyl indoles 1b-h and indole (1i) reacted efficiently with 2 a to afford the corresponding indole derivatives 3b-h and 3i in 48-91 and 72 % yields. The results showed that N-methyl indoles with electron-donating substituents were more reactive affording higher product yields than those with electron-withdrawing groups. Likewise, various substituted but-3-yn-1-ols 2b-e and other longer chain alkynyl alcohols 2 f-i also underwent a cyclization-addition reaction with N-methyl indole (1a) to provide the corresponding cyclization-addition products 3j-m and 3a, 3j, and 3n-o in good to excellent yields. The present platinum-catalyzed cyclization-addition reaction can be further extended into N-methyl pyrrole. Mechanistically, the catalytic reaction proceeds by an intramolecular hydroalkoxylation of alkynyl alcohol to afford cyclic enol ether followed by the addition of the C-H bond of indole to the unsaturated moiety of cyclic enol ether providing the final product. Experimental evidence to support this proposed mechanism is provided.

Synthesis of multi-substituted dihydrofurans via palladium-catalysed coupling between 2,3-alkadienols and pronucleophiles

Multi-substituted dihydrofurans were obtained from a palladium-catalysed coupling reaction between 2,3-alkadienols and ketones bearing an electron-withdrawing group at the α-position. Methanol as a solvent was essential for the initial dehydrative substitution to suppress the competitive hydroalkylation of the diene moiety. The substitution would be followed by intramolecular hydroalkoxylation under the same catalysis.

Trimethylaluminum (TMA)-catalyzed reaction of alkynyllithiums with ethylene oxide: Increased yields and purity of homopropargylic alcohols

An efficient protocol was developed to obtain homopropargylic alcohols. Subjecting alkynyllithiums and ethylene oxide to 10-20 mol% of trimethylaluminum provided homopropargylic alcohols in good yields. Georg Thieme Verlag Stuttgart.

First total synthesis of (+/-)-taxifolial a and (+/-)-iso-caulerpenyne.

The first synthesis of (+/-)-taxifolial A and iso-caulerpenyne was accomplished. The key steps in the sequence are (1) the stereoselective assembly of a vinyltin derived from butynediol and a functionalized aldehyde and (2) the construction of the dienyne moiety via a Stille cross-coupling.

Total synthesis of terpenoids isolated from caulerpale algae and their inhibition of tubulin assembly

Total synthesis of four analogue terpenoids isolated from Caulerpa taxifolia was achieved in good yield with a total control of each double bond. Biological tests to compare the activities of in vitro tubulin polymerisation between the natural caulerpenyne and the synthetic caulerpenyne and its derivatives were also performed. Georg Thieme Verlag Stuttgart.

Atom-Economical Cross-Coupling of Internal and Terminal Alkynes to Access 1,3-Enynes

Selective carbon-carbon (C-C) bond formation in chemical synthesis generally requires prefunctionalized building blocks. However, the requisite prefunctionalization steps undermine the overall efficiency of synthetic sequences that rely on such reactions, which is particularly problematic in large-scale applications, such as in the commercial production of pharmaceuticals. Herein, we describe a selective and catalytic method for synthesizing 1,3-enynes without prefunctionalized building blocks. In this transformation several classes of unactivated internal acceptor alkynes can be coupled with terminal donor alkynes to deliver 1,3-enynes in a highly regio- and stereoselective manner. The scope of compatible acceptor alkynes includes propargyl alcohols, (homo)propargyl amine derivatives, and (homo)propargyl carboxamides. This method is facilitated by a tailored P,N-ligand that enables regioselective addition and suppresses secondary E/Z-isomerization of the product. The reaction is scalable and can operate effectively with as low as 0.5 mol % catalyst loading. The products are versatile intermediates that can participate in various downstream transformations. We also present preliminary mechanistic experiments that are consistent with a redox-neutral Pd(II) catalytic cycle.

Migratory Hydrogenation of Terminal Alkynes by Base/Cobalt Relay Catalysis

Migratory functionalization of alkenes has emerged as a powerful strategy to achieve functionalization at a distal position to the original reactive site on a hydrocarbon chain. However, an analogous protocol for alkyne substrates is yet to be developed. Herein, a base and cobalt relay catalytic process for the selective synthesis of (Z)-2-alkenes and conjugated E alkenes by migratory hydrogenation of terminal alkynes is disclosed. Mechanistic studies support a relay catalytic process involving a sequential base-catalyzed isomerization of terminal alkynes and cobalt-catalyzed hydrogenation of either 2-alkynes or conjugated diene intermediates. Notably, this practical non-noble metal catalytic system enables efficient control of the chemo-, regio-, and stereoselectivity of this transformation.

A copper-catalyzed pyrrolidine and preparation of quinoline derivatives method and application (by machine translation)

The invention discloses a pyrrolidine and for preparation of quinoline derivatives, comprises the following steps: the cuprous chloride and aminoalkynes, alkynes are added to a reaction flask, adding the solvent DMF, under microwave irradiation, 150 °C reaction 30 minutes to obtain the target product. The method has high yield, time fast, low cost, for the end of the substrate is not limited to the alkyne, to non-terminalthe alkyne is eventerminal alkyne and has good serviceability, solves the defect of the gold catalytic of this reaction, the method for preparing the compound portion of through the cell active test, with tumor cell proliferation inhibitory activity, indicates this method is in the anti-tumor drug discovery has potential application value. (by machine translation)

Rhodium(III)-catalyzed intramolecular annulation through C-H activation: Total synthesis of (±)-antofine, (±)-septicine, (±)-tylophorine, and rosettacin

Annulation: The efficient synthesis of 3-hydroxyalkyl isoquinolones and 6-hydroxyalkyl 2-pyridones is enabled through the intramolecular annulation of alkyne-tethered hydroxamic esters (see scheme, Cp= pentamethylcyclopentadienyl). The reaction features high regioselectivity, broad substrate scope, and excellent functional-group tolerance, proceeds under mild reaction conditions with low catalyst loading, and obviates the need for an external oxidant.

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.