6710-62-9

Basic information

• Product Name: 1-Phenyl-2-butyn-1-one
• Synonyms: 1-Phenyl-2-butyn-1-one;Tetrolophenone;1-phenylbut-2-yn-1-one;2-Butynophenone;Butynophenone;NSC 138596
• CAS NO: 6710-62-9
• Molecular Formula: C₁₀H₈O
• Molecular Weight: 144.17
• Mol File: 6710-62-9.mol

Chemical Properties

• Boiling Point: 236.7°C at 760 mmHg
• Flash Point: 86.4°C
• Appearance: /
• Density: 1.05g/cm³
• Vapor Pressure: 0.0468mmHg at 25°C
• Refractive Index: 1.547
• CAS DataBase Reference: 1-Phenyl-2-butyn-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Phenyl-2-butyn-1-one(6710-62-9)
• EPA Substance Registry System: 1-Phenyl-2-butyn-1-one(6710-62-9)

Safety Data

• Hazardous Substances Data: 6710-62-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Chemistry Research:
1-Phenyl-2-butyn-1-one is used as a research compound for studying organic chemistry, particularly in the synthesis and reactions of various organic compounds.
Used in Pharmaceutical Synthesis:
1-Phenyl-2-butyn-1-one is used as a building block in the synthesis of pharmaceuticals, contributing to the development of new drugs and medicinal compounds.
Used in Agrochemical Synthesis:
1-Phenyl-2-butyn-1-one is used as a building block in the synthesis of agrochemicals, aiding in the development of new agricultural chemicals and pesticides.
Used as a Reagent in Organic Synthesis:
1-Phenyl-2-butyn-1-one is used as a valuable reagent in organic synthesis due to its ability to react with various nucleophiles, facilitating the creation of diverse chemical structures and compounds.

InChI:InChI=1/C10H8O/c1-2-6-10(11)9-7-4-3-5-8-9/h3-5,7-8H,1H3

Upstream product

• 590-14-7 1-bromo-1-propene 
• 32398-66-6 1-phenylbut-2-yn-1-ol 
• 546-67-8 lead(IV) tetraacetate 
• 355116-18-6 phenyl 1-(tetrazol-5-yl)ethyl ketone 
• 100-52-7 benzaldehyde 
• 14949-99-6 sodium triethyl-1-propinylborate 
• 98-88-4 benzoyl chloride 
• 22548-20-5 Kalium- 
• 22548-32-9 Natrium- 
• 22548-15-8 Lithium- 
• 67538-43-6 dipropynyltrimethylantimony(V) 
• 78-75-1 1,2-Dibromopropane 
• 6919-61-5 N-methoxy-N-methylbenzamide 
• 6224-91-5 trimethyl(prop-1-ynyl)silane 

Downstream Products

• 17335-06-7 ethyl 4-benzoyl-5-methylisoxazole-3-carboxylate 
• 18052-64-7 1-Phenyl-1-trimethylsilyloxy-butin-⁽²⁾ 
• 39159-65-4 1-benzoyl-2-(N-phenylamino)-1-propene 
• 107057-99-8 5-phenacyl-dihydro-furan-2-one 
• 1234155-82-8 (E)-3,4-dimethyl-1-phenyl-2-penten-1-one 
• 145089-91-4 (Z)-3-(2-hydroxyphenylamino)-1-phenylbut-2-en-1-one 
• 10250-60-9 1,5-dimethyl-3-phenyl-1H-pyrazole 

Relevant articles and documents

Rhodium-Catalyzed C?H Activation/Annulation Cascade of Aryl Oximes and Propargyl Alcohols to Isoquinoline N-Oxides

A β-hydroxy elimination instead of common oxidization to carbonyl group in secondary propargyl alcohols was successfully developed to form 2-benzyl substituted isoquinoline N-oxides by a Rhodium-catalyzed C?H activation and annulation cascade, in which moderate to excellent yields (up to 92%) could be obtained under mild reaction conditions, along with good regioselectivity, broad generality and applicability. (Figure presented.).

Highly Chemo- And Enantioselective Rh-Catalyzed Hydrogenation of β-Sulfonyl-α,β-unsaturated Ketones: Access to Chiral γ-Ketosulfones

Rh-catalyzed highly chemo- and enantioselective hydrogenation of β-sulfonyl-α,β-unsaturated ketones was first successfully developed. Remarkably, a variety of enantioenriched γ-ketosulfones were generated in good to high yields with excellent chemo/enantioselectivities (82-99% yields, >99:1 chemoselectivity, 88 to >99% ee). Moreover, the gram-scale asymmetric hydrogenation was carried out smoothly in 97% yield and 97% ee. Preliminary DFT computations furnished a reasonable explanation for the high chemoselectivity and enantioselectivity.

Laccase-mediated Oxidations of Propargylic Alcohols. Application in the Deracemization of 1-arylprop-2-yn-1-ols in Combination with Alcohol Dehydrogenases

The catalytic system composed by the laccase from Trametes versicolor and the oxy-radical TEMPO has been successfully applied in the sustainable oxidation of fourteen propargylic alcohols. The corresponding propargylic ketones were obtained in most cases in quantitative conversions (87–>99 % yield), demonstrating the efficiency of the chemoenzymatic methodology in comparison with traditional chemical oxidants, which usually lead to problems associated with the formation of by-products. Also, the stereoselective reduction of propargylic ketones was studied using alcohol dehydrogenases such as the one from Ralstonia species overexpressed in E. coli or the commercially available evo-1.1.200, allowing the access to both alcohol enantiomers mostly with complete conversions and variable selectivities depending on the aromatic pattern substitution (97–>99 % ee). To demonstrate the compatibility of the laccase-mediated oxidation and the alcohol dehydrogenase-catalyzed bioreduction, a deracemization strategy starting from the racemic compounds was developed through a sequential one-pot two-step process, obtaining a selection of (S)- or (R)-1-arylprop-2-yn-1-ols with excellent yields (>98 %) and selectivities (>98 % ee) depending on the alcohol dehydrogenase employed.

Gold(iii)-catalyzed azide-yne cyclization/O-H insertion cascade reaction for the expeditious construction of 3-alkoxy-4-quinolinone frameworks

A gold-catalyzed 6-endo-digazide-yne cyclization/O-H insertion cascade reaction of azide-tethered alkynes with alcohols has been developed, and it provides an expeditious access to 3-alkoxy-4-quinoline derivatives in good to high yields under mild and neutral reaction conditions with broad substrate generality. The utility of this method is emphasized by a scalable experiment and concise total synthesis of a bioactive natural product Leiokinine A, and other bioactive quinoline analogs.

Covalent Adaptable Networks with Tunable Exchange Rates Based on Reversible Thiol–yne Cross-Linking

The design of covalent adaptable networks (CANs) relies on the ability to trigger the rearrangement of bonds within a polymer network. Simple activated alkynes are now used as versatile reversible cross-linkers for thiols. The click-like thiol–yne cross-linking reaction readily enables network synthesis from polythiols through a double Michael addition with a reversible and tunable second addition step. The resulting thioacetal cross-linking moieties are robust but dynamic linkages. A series of different activated alkynes have been synthesized and systematically probed for their ability to produce dynamic thioacetal linkages, both in kinetic studies of small molecule models, as well as in stress relaxation and creep measurements on thiol–yne-based CANs. The results are further rationalized by DFT calculations, showing that the bond exchange rates can be significantly influenced by the choice of the activated alkyne cross-linker.

Transition-Metal-Free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds

A novel ring expansion reaction of indene-1,3-dione with alkynyl ketones under transition-metal-free conditions has been developed. This process offers an efficient and direct way to synthesize benzoannulated seven-membered rings or fused-ring compounds t

A general two-step one-pot synthesis process of ynones from α-keto acids and 1-iodoalkynes

A general two-step one-pot synthesis process of ynones was developed by cycloaddition of α-keto acids and 1-iodoalkynes followed by a ring-opening reaction. Its easy conditions and novel mechanism endowed it with two distinctive advantages: iodine-atom bonded to C(sp2) remained intact and α-keto acids became a part of the triple bonds in ynones.

Functionalization of the "bay Region" of Perylene in Reaction with 1-Arylalk-2-yn-1-ones Catalyzed by Trifluoromethanesulfonic Acid: One-Step Approach to 1-Acyl-2-alkylbenzo[ ghi]perylenes

We describe a convenient method of the synthesis of 1-acyl-2-alkylbenzo[ghi]perylenes via functionalization of the "bay region" of perylene in the reaction with 1-arylalk-2-yn-1-ones catalyzed by trifluoromethanesulfonic acid. We showed that the formation

PROCESS FOR PRODUCING ALKYNYLKETONE DERIVATIVE

The present invention relates to a Sonogashira-Carbonylation reaction using two types of gas, as well as novel crystals which can control a heat of the said reaction and the process of producing the same. In addition, the present invention relates to a li

Oxyboration with and without a Catalyst: Borylated Isoxazoles via B-O-Bond Addition

Herein we report an oxyboration reaction with activated substrates that employs B-O σ bond additions to C-C π bonds to form borylated isoxazoles, which are potential building blocks for drug discovery. Although this reaction can be effectively catalyzed by gold, it is the first example of uncatalyzed oxyboration of C-C π bonds by B-O σ bonds-and only the second example that is catalyzed. This oxyboration reaction is tolerant of groups incompatible with alternative lithiation/borylation and palladium-catalyzed C-H activation/borylation technologies for the synthesis of borylated isoxazoles.