101974-69-0

Basic information

• Product Name: 3-cyclopropylprop-2-yn-1-ol
• Synonyms: 3-cyclopropylprop-2-yn-1-ol;3-Cyclopropyl-2-propyn-1-ol;2-Propyn-1-ol, 3-cyclopropyl-
• CAS NO: 101974-69-0
• Molecular Formula: C₆H₈O
• Molecular Weight: 96.12712
• Mol File: 101974-69-0.mol

Chemical Properties

• Boiling Point: 78-79 °C(Press: 10 Torr)
• Appearance: /
• Density: 1.06±0.1 g/cm3(Predicted)
• PKA: 12.91±0.10(Predicted)
• CAS DataBase Reference: 3-cyclopropylprop-2-yn-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-cyclopropylprop-2-yn-1-ol(101974-69-0)
• EPA Substance Registry System: 3-cyclopropylprop-2-yn-1-ol(101974-69-0)

Safety Data

• Hazardous Substances Data: 101974-69-0(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
3-cyclopropylprop-2-yn-1-ol is utilized as a building block in organic synthesis, serving as a key component in the creation of various pharmaceuticals and agrochemicals. Its unique structure allows for versatile chemical reactions, making it a valuable intermediate in the synthesis of complex organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-cyclopropylprop-2-yn-1-ol is used as a precursor for the development of new drugs. Its unique structural features enable the design of novel therapeutic agents with potential applications in treating various diseases and conditions.
Used in Agrochemical Industry:
3-cyclopropylprop-2-yn-1-ol also finds applications in the agrochemical industry, where it is used as a starting material for the synthesis of new pesticides and other agrochemicals. Its unique properties can contribute to the development of more effective and environmentally friendly products.
Used in Fine Chemicals Production:
3-cyclopropylprop-2-yn-1-ol is employed in the production of fine chemicals, which are high-purity chemicals used in various applications, including research, pharmaceuticals, and specialty industries. Its role as a precursor allows for the synthesis of high-value compounds with specific properties.
Used in Material Science Research:
In the field of material science, 3-cyclopropylprop-2-yn-1-ol has potential uses in the development of new materials. Its unique structural features can be leveraged to create novel materials with specific properties, such as improved stability or reactivity.
Used in Academic and Industrial Research:
3-cyclopropylprop-2-yn-1-ol is a valuable compound in research settings, both academic and industrial. Its unique structure and properties make it an interesting subject for studies aimed at understanding its reactivity, potential applications, and the development of new synthetic methods.

Upstream product

• 50-00-0 formaldehyd 
• 6746-94-7 Cyclopropylacetylene 
• 110-88-3 1,3,5-Trioxan 
• 122244-78-4 1,1-dibromo-2-cyclopropylehylene 
• 14267-92-6 1-chloro-4-pentyne 

Downstream Products

• 158956-34-4 (E)-3-cyclopropyl-2-propen-1-ol 
• 1151920-05-6 1‐benzyl‐4‐cyclopropyl‐1H‐1,2,3‐triazole 
• 7358-93-2 3‐cyclopropyl‐2‐propynoic acid 
• 1428676-48-5 tert-butyl (3-cyclopropylprop-2-yn-1-yl)(tosyl)carbamate 
• 1401797-88-3 N-(3-cyclopropylprop-2-yn-1-yl)-4-methylbenzenesulfonamide 
• 1324010-91-4 (1-cyclopropylpropa-1,2-dien-1-yl)dimethylphenylsilane 

Relevant articles and documents

[2+2+2]-Cyclotrimerization of 1-Cyclopropyl-1,6-diynes with Alkynes: Formation of Cyclopropylarenes.

Cyclotrimerization of 1-cyclopropyl-1,6-diynes with various terminal alkynes was tested under catalytic conditions using rhodium and ruthenium catalysts. We observed that the regioselectivity of the reaction, that is, formation of 1,2- or 1,3-regioisomers, was opposite for the two metals. For the ruthenium complex [Cp Ru(cod)Cl]-catalyzed reactions the yields were in many cases high with a strong preference for the formation of 1,3-substituted regioisomers. In the case of catalysis by the rhodium complex [RhCl(PPh3)3], 1,2-substituted products were generally preferred, albeit the selectivity was often modest. However, by changing the ligand environment around the central rhodium atom the regioselectivity as well as yields of the products were significantly improved. For example, by using a combination of the rhodium complex [Rh(cod)2BF4] and 1,4-bis(diphenylphosphino)butane the regioselectivity was changed from 1:1 to 1:12 in favor of the 1,2-regioisomer. This catalytic system was also applied for synthesis of a substituted 4-cyclopropyl-3-hydroisobenzofuran-1-one that could serve as a potential intermediate for preparation of antihypertensive agents.

New elements in the reactivity of α-cyclopropyl vinyl radicals

The reactivity of the α-cyclopropyl vinyl radical has been examined through the use of propargylic bromomethyldimethylsilyl ethers bearing a cyclopropyl group on the acetylenic moiety. With unsubstituted precursors, allenes can be obtained. With appropriate trapping possibilities (5-exo cyclization or hydrogen transfer), the cyclopropyl moiety on the vinyl radical is retained.

Gold(I)-catalyzed intramolecular cycloisomerization of propargylic esters with furan rings

A gold-catalyzed intramolecular cycloisomerization of a-yne-furans 1 is described in this contribution. A variety of cyclic α,β-unsaturated aldehyde or ketone derivatives and nitrogen-containing tricyclic adducts were obtained selectively in moderate to excellent yields under mild conditions by varying the substituents on the standard substrates.

Copper(i) iodide catalyzed synthesis of primary propargylic alcohols from terminal alkyne

A highly efficient and practical method for the synthesis of primary propargylic alcohols has been developed using CuI as catalyst and paraformaldehyde as the formaldehyde source. The reaction was performed under mild reaction conditions offering the desired products in good to excellent yields with a variety of terminal alkynes.

Metal-Free Catalyzed Cyclization of N-Methoxybenzamides to Construct Quaternary Carbon-Containing Isoindolinones

Through the intramolecular cyclization of N-methoxybenzamides, a simple and efficient method for constructing valuable isoindolinones under metal-free conditions was developed. The reaction was featured by employing low-cost catalyst, simple operation, 100% atomic economy and excellent regioselectivity. Moreover, a detailed computational study on the reaction system has been performed to clarify the mechanism. This protocol tolerated a variety of functional groups and provided a metal-free protocol for the synthesis of chromane- or tetrahydroquinoline-fused isoindolinones in good yields.

CFTR-MODULATING ARYLAMIDES

The present disclosure relates to heterocyclic compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditions mediated by deficient CFTR activity, in particular cystic fibrosis.

ARYLAMIDES AND METHODS OF USE THEREOF

The present disclosure relates to heterocyclic compounds, pharmaceutically acceptable salts thereof, and pharmaceutical preparations thereof. Also described herein are compositions and the use of such compounds in methods of treating diseases and conditio

Gold(III)-Catalyzed Regioselective Oxidation/Cycloisomerization of Diynes: An Approach to Fused Furan Derivatives

The first gold(III)-catalyzed regioselective oxidation/cycloisomerization of diynes 1 with pyridine N-oxide as the oxidant was developed, providing a range of synthetically valuable and useful fused furan derivatives 3 in moderate to good yields. Control experiments and the confirmation structure of minor products 5 suggest that this chemistry was a concerted gold(III)-catalyzed oxidation/SN2′-type addition/cyclization process via a β-gold vinyloxypyridinium intermediate and a putative vinyl cation intermediate.

Redox-Neutral Arylations of Vinyl Cation Intermediates

Herein we present a new unified concept for C?C bond formation under redox-neutral conditions. Our strategy hinges upon interception of a vinyl cation with a sulfoxide resulting in simultaneous C–C and C?O bond formation and arylation. A range of structurally diverse vinyl cations are generated in situ in the presence of a sulfoxide, resulting in hydrative arylation, direct arylation of enol triflates and interrupted Meyer–Schuster rearrangement. Mechanistic investigations showcase the crucial role played by the fleeting vinyl cation intermediate and structural features that lead to its stabilization. Applications of the reaction products to synthesis are also presented. (Figure presented.).

Olefin-Migrative Cleavage of Cyclopropane Rings through the Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes

A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes. (Figure presented.).