105-31-7

Usage

Uses

Used in Chemical Synthesis:
1-Hexyn-3-ol is utilized as a key intermediate in the synthesis of racemic 3-hydroxy-2-hexanone, a compound that finds applications in various chemical processes and industries.
Used in Pharmaceutical and Chemical Research:
1-Hexyn-3-ol is also employed in the preparation of 1,2,3-triazoles, which are significant in pharmaceutical and chemical research due to their unique properties and potential applications in medicinal chemistry.
Used in Corrosion Inhibition:
1-Hexyn-3-ol serves as an effective corrosion inhibitor, particularly against mineral acids. Its ability to protect materials from corrosive effects makes it valuable in various industrial applications.
Used in Oil and Gas Industry:
In the oil and gas sector, 1-Hexyn-3-ol is used as a high-temperature oil-well-acidizing inhibitor. This application is crucial for maintaining the integrity and efficiency of oil wells, especially in harsh conditions.

Hazard

Toxic by ingestion and inhalation, absorbed by skin. Probably flammable.

InChI:InChI=1/C6H10O/c1-3-5-6(7)4-2/h2,6-7H,3,5H2,1H3/t6-/m0/s1

Upstream product

• 624-67-9 Propargylic aldehyde 
• 927-77-5 n-propylmagnesium bromide 
• 4301-15-9 ethynyldimagnesium dibromide 
• 123-72-8 butyraldehyde 
• 100312-92-3 C₆H₉⁽³⁾HO 
• 7446-08-4 selenium(IV) oxide 
• 64-17-5 ethanol 
• 693-02-7 hex-1-yne 
• 689-00-9 hex-1-yn-3-one 
• 4301-14-8 acetylenemagnesium bromide 
• 65032-27-1 ethynylmagnesium chloride 
• 70095-35-1 (R)-hex-1-yn-3-yl acetate 
• 108-22-5 Isopropenyl acetate 
• 122-79-2 Phenyl acetate 

Downstream Products

• 623-37-0 n-hexan-3-ol 
• 689-00-9 hex-1-yn-3-one 
• 15352-99-5 (+/-)-hex-1-yn-3-yl acetate 
• 54123-75-0 3-hydroxy-2-hexanone 
• 52385-32-7 1,3,5-Tris(1-hydroxybutyl)benzol 
• 56438-75-6 3-benzoyloxy-1-hexyne 
• 13336-83-9 <3-Propyl-allenyl-(1)>-phenyl-phosphinsaeure--ester 
• 83074-76-4 (1,2-Hexadienyl)(p-tolyl)sulfoxid 
• 113831-75-7 1-(3-Hydroxy-1-hexinyl)-2,6,6-trimethyl-2-cyclohexen-1-ol 
• 75918-67-1 2-(1-Ethynyl-butyl)-1-methyl-1-phenyl-isourea 
• 65518-46-9 (2E,4E)-hepta-2,4-dienoic acid 
• 95851-15-3 2-Ethyl-1-(3-hydroxy-1-hexinyl)-2,6-dimethylcyclohexanol 
• 4798-44-1 1-hexene-3-ol 
• 15986-94-4 2-n-Propyl-3-methyl-5,6-dihydro-pyrazin 

Relevant academic research and scientific papers

Regioselective Annulation of Aryl Sulfonamides with Allenes through Cobalt-Promoted C-H Functionalization

The development of an efficient method for the construction of biologically relevant sultams is described, which represents the first case of cobalt-promoted C-H/N-H functionalization of sulfonamides with allenes. This newly developed annulation reaction demonstrated good functional group tolerance and excellent regioselectivity. Both terminal monosubstituted allenes and internal disubstituted allenes can be employed to give the desired sultams in good yields. This strategy can be successfully used to build a unique sultam library with novel structural diversity.

Rates of Base-Catalyzed Hydrogen Exchange of Terminal Acetylenes in Aqueous Solution. Absence of Resonance Interaction

Rates of detritiation of 13 monosubstituted acetylenes labeled at the acetylenic hydrogen position were measured in aqueous amine buffer solution at 25 deg C, and hydroxide ion catalytic coefficients were evaluated.These rate constants, plus a few additional values from the literature, give a good correlation against inductive or field substituent constants: log(kHO-/M-1s-1) = 1.46+/-0.12 + (8.00+/-0.50)?I.This correlation is not improved by addition of resonance substituted constants, and the coefficients of the resonance term in two different dual parameter (resonance plus field) treatments of the data are in fact zero.

Synthesis of polysubstituted stereodefined olefins via the reactivity of sp2 organo-gem-bismetallics

We describe a new synthetically useful procedure for the stereoselective synthesis of polysubstituted olefins via the reaction of sp2 organometallics with different electrophiles.

Rhodium-Catalyzed Cyclization of Terminal and Internal Allenols: An Atom Economic and Highly Stereoselective Access Towards Tetrahydropyrans

A comprehensive study of a diastereoselective Rh-catalyzed cyclization of terminal and internal allenols is reported. The methodology allows the atom economic and highly syn-selective access to synthetically important 2,4-disubstituted and 2,4,6-trisubstituted tetrahydropyrans (THP). Furthermore, its utility and versatility are demonstrated by a great functional-group compatibility and the enantioselective total synthesis of (?)-centrolobine.

A Convergent, Stereoselective Route to Trisubstituted Alkenyl Boronates

A modular, stereoselective route to trisubstituted (Z)-alkenyl (MIDA)boronates is described, consisting of the radical addition-fragmentation of dithiocarbonates to 2-(MIDA)boronyl-3-(2′-fluoro-pyridyl-6′-oxy)-alkenes. The bulky (MIDA)boronate ensures a highly stereoselective fragmentation that is enhanced by the poor stabilization of the radical adjacent to the tetravalent boron atom. The vinyl boronate precursors are prepared from propargyl alcohols by copper-catalyzed regioselective protoboration of their fluoropyridoxy derivatives, with the fluoropyridine acting as an internal directing group.

Ester Synthesis in Water: Mycobacterium smegmatis Acyl Transferase for Kinetic Resolutions

The acyl transferase from Mycobacterium smegmatis (MsAcT) catalyses transesterification reactions in aqueous media because of its hydrophobic active site. Aliphatic cyanohydrin and alkyne esters can be synthesised in water with excellent and strikingly opposite enantioselectivity [(R);E>37 and (S);E>100, respectively]. When using this enzyme, the undesired hydrolysis of the acyl donor is an important factor to take into account. Finally, the choice of acyl donor can significantly influence the obtained enantiomeric excesses. (Figure presented.).

Some special features of hydroalumination-iodination of alkyne-1,4-diols

Hydroalumination-iodination of alkyne-1,4-diols of different structure showed that with increasing number of substituents at the C-OH group the amount of β-iodo-substituted products with respect to this group increased. In the case of symmetric secondary 1,4-diols the reaction results in a 1: 1 mixture of stereoisomeric iodoalkenediols, and in the case of phenyl substituents the reaction proceeds regio- and stereoselectively to give an alkenediol iodine atom in the β-position to phenyl group.

A novel Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates with acyclic dienophiles

A novel DABCO-catalyzed Ireland-Claisen rearrangement/Diels-Alder tandem reaction of propargylic acrylates 3 with dienophiles 4 was developed in the presence of an excess TMSCl and DBU with 1% hydroquinone as polymerization inhibitor in acetonitrile at refluxing temperature under air. This protocol gave cyclic α,β-unsaturated carboxylic acids 5 with complete regioselectivity.

New and efficient synthesis of 1,3-dienylphosphonates by palladium-catalyzed substitution of propargylic esters to diethyl phosphite

An efficient route to the synthesis of 1,3-dienylphosphonates (1) has been developed for the first time by the substitution of propargylic esters (2) to the diethyl phosphite (3) nucleophile in the presence of Pd2 (dba) 3 · CHCl3 (2 mol %) and 2,2′- bis(diphenylphosphino)-1,1′-binaphthyl (4 mol%). Both the alkyl and aryl 1,3-dienylphosphonates can be prepared from this transformation. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

The substrate spectrum of the inverting sec-alkylsulfatase Pisa1

The substrate spectrum of the inverting alkylsulfatase Pisa1 was investigated using a range of sec-alkyl sulfate esters bearing aromatic, olefinic and acetylenic moieties. Perfect enantioselectivities were obtained for substrates bearing groups of different size adjacent to the sulfate ester moiety. Insufficient selectivities could be doubled by using dimethyl sulfoxide (DMSO) as co-solvent. Hydrolytically unstable benzylic sulfate esters could be sufficiently stabilised by introduction of electron-withdrawing substituents. Overall, Pisa1 appears to be a very useful inverting alkylsulfatase for the deracemisation of rac-sec-alcohols via enzymatic hydrolysis of their corresponding sulfate esters, which furnishes homochiral products possessing the 'anti-Kazlauskas' configuration. Copyright