17356-19-3

Basic information

• Product Name: 1-ETHYNYLCYCLOPENTANOL
• Synonyms: 1-ethynyl-cyclopentano;Cyclopentanol, 1-ethynyl-;1-(1-ETHYNYL)-1-CYCLOPENTANOL;1-ETHYNYL-1-CYCLOPENTANOL;1-ETHYNYLCYCLOPENTANOL;Cyclopentanol, 1-ethynyl- (6CI, 7CI, 8CI, 9CI);1-ETHYNYL-1-CYCLOPENTANOL, 98+%;cyclopentyl ethynyl carbinol
• CAS NO: 17356-19-3
• Molecular Formula: C₇H₁₀O
• Molecular Weight: 110.15
• EINECS: 241-385-7
• Product Categories: Alkynes;Organic Building Blocks;Terminal;Building Blocks;Chemical Synthesis;Organic Building Blocks
• Mol File: 17356-19-3.mol

Chemical Properties

• Melting Point: 27 °C
• Boiling Point: 156-159 °C(lit.)
• Flash Point: 120 °F
• Appearance: clear colorless to yellow liquid after melting
• Density: 0.962 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.1mmHg at 25°C
• Refractive Index: n20/D 1.474(lit.)
• Storage Temp.: Flammables area
• PKA: 13.34±0.20(Predicted)
• Water Solubility: Insoluble in water.
• BRN: 1924167
• CAS DataBase Reference: 1-ETHYNYLCYCLOPENTANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 1-ETHYNYLCYCLOPENTANOL(17356-19-3)
• EPA Substance Registry System: 1-ETHYNYLCYCLOPENTANOL(17356-19-3)

Safety Data

• Hazard Codes: Xi
• Statements: 10-36/37
• Safety Statements: 16-26-27-36/37/39
• RIDADR: UN 1986 3/PG 3
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 17356-19-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-Ethynylcyclopentanol is used as a building block for the synthesis of various organic compounds. Its unique structure allows it to be a versatile intermediate in the preparation of pharmaceuticals, agrochemicals, and other specialty chemicals. The ethynyl group can be further functionalized through reactions such as hydrolysis, reduction, or coupling, enabling the creation of a wide range of molecules with diverse properties and applications.
Used in Pharmaceutical Industry:
1-Ethynylcyclopentanol is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with improved efficacy and selectivity. The ethynyl group can be modified to introduce various functional groups, which can enhance the drug's pharmacokinetic and pharmacodynamic properties.
Used in Agrochemical Industry:
1-Ethynylcyclopentanol is used as a starting material for the synthesis of agrochemicals, such as pesticides and herbicides. Its unique structure can be tailored to create molecules with specific modes of action, leading to the development of more effective and environmentally friendly agrochemicals.
Used in Specialty Chemicals:
1-Ethynylcyclopentanol is used in the production of specialty chemicals, such as fragrances, dyes, and polymers. Its unique structure allows for the creation of novel compounds with specific properties, making it a valuable resource in the development of new materials and products.

Synthesis Reference(s)

Synthetic Communications, 18, p. 131, 1988 DOI: 10.1080/00397918808077336

InChI:InChI=1/C7H10O/c1-2-7(8)5-3-4-6-7/h1,8H,3-6H2

Upstream product

• 120-92-3 cyclopentanone 
• 74-86-2 acetylene 
• 65032-27-1 ethynylmagnesium chloride 
• 1066-54-2 trimethylsilylacetylene 
• 75-20-7 calcium carbide 
• 71321-24-9 1-<2-(Trimethylsilyl)ethynyl>cyclopentan-1-ol 
• 62785-89-1 (1-ethynylcyclopentyloxy)trimethylsilane 
• 4301-14-8 acetylenemagnesium bromide 
• 70277-75-7 lithium acetylide 
• 1216963-74-4 lithium acetylide-ethylenediamine complex 
• 1066-26-8 sodium acetylide 
• 4301-15-9 ethynyldimagnesium dibromide 
• 60-29-7 diethyl ether 

Downstream Products

• 98959-72-9 methyl-carbamic acid-(1-ethynyl-cyclopentyl ester) 
• 146998-47-2 1-{3-[Bis-(2-chloro-ethyl)-amino]-prop-1-ynyl}-cyclopentanol 
• 54526-80-6 methyl (E)-3-(1-cyclopenten-1-yl)-2-propenoate 
• 144776-80-7 2-cyclopentylidene-3-(dimethylphenylsilyl)propanal 
• 3859-35-6 1-vinyl-1-cyclopentanol 
• 301699-17-2 1-[3-hydroxy-3-(4-methylthiophenyl)-prop-1-ynyl]-cyclopentanol 
• 32584-63-7 (C₆H₅)2SbCC-c-C₅H₈-1-OH 
• 1067324-18-8 3,3-tetramethylenepropa-1,2-dien-1-yl diphenyl phosphine oxide 
• 1033042-00-0 2,3-dihydro-3-methyl-6-(1'-p-nitrophenoxy-cyclopentyl)-thiopyran-4-one 
• 1174028-63-7 4-hydroxy-3-(2-{[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-4-methoxyphenyl)-5,6,7-trimethoxy-chromen-2-one 
• 1174028-66-0 4-(2-{[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-4-methoxyphenyl)chromen-2-one 
• 1174028-69-3 4-(2-{[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-4-methoxyphenyl)-5,7-dimethoxychromen-2-one 
• 1174028-71-7 4-(2-{[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-4-methoxyphenyl)-5,6,7-trimethoxychromen-2-one 
• 1174028-60-4 4-hydroxy-3-(2-{[4-(1-hydroxycyclopentyl)-1H-1,2,3-triazol-1-yl]methyl}-4-methoxyphenyl)-5,7-dimethoxychromen-2-one 

Relevant articles and documents

Halogen-Substituted Allenyl Ketones through Ring Opening of Nonstrained Cycloalkanols

An efficient synthesis of halogen-substituted allenyl ketones via Ag-catalyzed oxidative ring opening of allenyl cyclic alcohols under mild reaction conditions has been achieved. The reaction features a wide substrate scope and excellent regioselectivity. The synthetic potential of the products has been demonstrated by their conversion to stereodefined alkenes and heterocyclic compounds.

Enantio- And Diastereodivergent Construction of 1,3-Nonadjacent Stereocenters Bearing Axial and Central Chirality through Synergistic Pd/Cu Catalysis

In contrast to the widely explored methods for the asymmetric synthesis of molecules bearing a single stereocenter or adjacent stereocenters, the concurrent construction of 1,3-stereogenic centers in an enantio- and diastereoselective manner remains a challenge, especially in acyclic systems. Herein, we report an enantio- and diastereodivergent construction of 1,3-nonadjacent stereocenters bearing allenyl axial and central chirality through synergistic Pd/Cu-catalyzed dynamic kinetic asymmetric allenylation with racemic allenylic esters. The protocol is suitable for a wide range of substrates including the challenging allenylic esters with less sterically bulky substituents and provided chiral allenylic products bearing 1,3-nonadjacent stereocenters with high levels of enantio- and diastereoselectivities (up to >20:1 dr and >99% ee). Furthermore, several representative transformations involving axial-to-central chirality transfer were conducted, affording useful structural motifs containing nonadjacent stereocenters in a diastereodivergent manner.

ETHERS AND ESTERS OF 1-SUBSTITUTED CYCLOALKANOLS FOR USE AS AROMA CHEMICALS

The present invention relates to the use of an ether or an ester of a 1 -substituted cycloalkanol or of mixtures of two or more ethers or esters of 1 -substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof as aroma chemicals; to the use thereof for modifying the scent character of a fragranced composition; to an aroma chemical composition containing an ether or an ester of a 1 -substituted cycloalkanol or of mixtures of two or more ethers or esters of 1 -substituted cycloalkanols or of a stereoisomer thereof or of a mixture of two or more stereoisomers thereof; and to a method of preparing a fragranced composition or for modifying the scent character of a fragranced composition. The invention further relates to specific ethers or esters of 1 -substituted cycloalkanols.

Trialkylborane-Mediated Propargylation of Aldehydes Using γ-Stannylated Propargyl Acetates

A transition-metal-free three-component process that combines aldehydes, 3-(tributylstannyl)propargyl acetates formed in situ from readily available propargyl acetates, and trialkylboranes provides access to a range of 1,2,4-trisubstituted homopropargylic alcohols. The addition of diisopropylamine plays a crucial role in the selective formation of homopropargylic alcohols. Importantly, this methodology can be extended to a single-flask reaction sequence starting from propargyl acetates.

Opioid receptor agonists and application thereof

The invention discloses compounds and salts thereof that can be used as opioid receptor ligands, a preparation method of the compounds, compositions containing the compounds, and a use of the compounds as [mu] opioid receptor agonists; the compounds are used for treatment of [mu] opioid receptor-mediated related diseases, such as pains and pain-related disorders.

Synthesis of Imidazo[1,2-a]pyridines and Imidazo[2,1-b]thiazoles Attached to a Cycloalkyl or Saturated Heterocycle Containing a Tertiary Hydroxy Substitution

A new method has been developed for the synthesis of imidazo[1,2-a]pyridines, imidazo[2,1-b]thiazoles, and benzo[d]imidazo[2,1-b]thiazoles attached to a cycloalkyl or saturated heterocycle containing a tertiary hydroxy substitution. Readily available substituted 2-aminopyridines, 2-aminothiazoles, and 2-aminobenzothiazoles were treated with bromohydroxycycloalkyl ethanones to afford the desired products in good yields.

Synthesis of Vinyl-, Allyl-, and 2-Boryl Allylboronates via a Highly Selective Copper-Catalyzed Borylation of Propargylic Alcohols

An efficient methodology for the synthesis of vinyl-, allyl-, and (E)-2-boryl allylboronates from propargylic alcohols via Cu-catalyzed borylation under mild conditions is reported. In the presence of commercially available Cu(OAc)2 or Cu(acac)2 and Xantphos, the reaction affords the desired products in up to 92% yield with a broad substrate scope (43 examples). Isolation of an allenyl boronate as the reaction intermediate suggests that an insertion-elimination-type reaction, followed by borylcupration, is involved in the borylation of propargylic alcohols.

Fluoride-assisted activation of calcium carbide: A simple method for the ethynylation of aldehydes and ketones

The fluoride-assisted ethynylation of ketones and aldehydes is described using commercially available calcium carbide with typically 5 mol % of TBAF·3H2O as the catalyst in DMSO. Activation of calcium carbide by fluoride is thought to generate an acetylide "ate"-complex that readily adds to carbonyl groups. Aliphatic aldehydes and ketones generally provide high yields, whereas aromatic carbonyls afford propargylic alcohols with moderate to good yields. The use of calcium carbide as a safe acetylide ion source along with economic amounts of TBAF·3H2O make this procedure a cheap and operationally simple method for the preparation of propargylic alcohols.

Facile synthesis of halogenated spiroketals via a tandem iodocyclization

A strategy for the synthesis of spiroketal compounds through a tandem iodocyclization of 1-(2-ethynylphenyl)-4-hydroxybut-2-yn-1-one derivatives is presented. This reaction could proceed under very mild conditions in a short time and avoid the use of expensive and toxic metal catalysts. Moreover, the resulting halides can be further exploited by subsequent palladium-catalyzed coupling reactions, which act as the important intermediates for building other valuable compounds.

Au-catalyzed formation of functionalized quinolines from 2-alkynyl arylazide derivatives

A new method for converting 2-alkynyl arylazide derivatives into functionalized polysubstituted quinolines following a gold-catalyzed 1,3-acetoxy shift/cyclization/1,2-group shift sequence has been developed. This transformation proceeds under mild reaction conditions, is efficient, and tolerates a large variety of functional groups.