63164-99-8

Basic information

• Product Name: Benzoic acid, 4-(3-hydroxy-1-butynyl)-, ethyl ester
• CAS NO: 63164-99-8
• Molecular Formula: C13H14O3
• Molecular Weight: 218.252
• Mol File: 63164-99-8.mol

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 4-(3-hydroxy-1-butynyl)-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 4-(3-hydroxy-1-butynyl)-, ethyl ester(63164-99-8)
• EPA Substance Registry System: Benzoic acid, 4-(3-hydroxy-1-butynyl)-, ethyl ester(63164-99-8)

Safety Data

• Hazardous Substances Data: 63164-99-8(Hazardous Substances Data)

Upstream product

• 51934-41-9 4-iodobenzoic acid ethyl ester 
• 2028-63-9 but-3-yn-2-ol 
• 5798-75-4 Ethyl 4-bromobenzoate 
• 1386903-40-7 ethyl 4-(3-oxobut-1-yn-1-yl)benzoate 

Downstream Products

• 1386903-40-7 ethyl 4-(3-oxobut-1-yn-1-yl)benzoate 
• 726202-41-1 4-[3-(2-Chloro-acetoxy)-but-1-ynyl]-benzoic acid ethyl ester 

Relevant articles and documents

Aromatic Aza-Claisen Rearrangement of Arylpropargylammonium Salts Generated in situ from Arynes and Tertiary Propargylamines

The charge-accelerated aza-Claisen rearrangement of ammonium salts serves as a key step in the construction of complex nitrogen-containing molecules. However, much less attention has been paid to the aromatic aza-Claisen rearrangement than to the aliphatic one. Herein, we report an unprecedented aromatic aza-Claisen rearrangement of arylpropargylammonium salts, generated in situ from arynes and tertiary propargylamines, delivering structurally diverse 2-propargylanilines in moderate to good yields with high regioselectivity. This rearrangement proceeds in the absence of strong bases or transition metals, is compatible with moisture and air, tolerates a wide variety of functional groups, and is amenable to forming 11- to 13-membered heterocycles with a triple bond. The 2-propargylaniline products were treated with aluminum chloride in ethanol to afford multisubstituted indoles in moderate to excellent yields. Finally, a series of deuterium-labeling experiments was performed to elucidate the reaction mechanism.

Nickel-Catalyzed Asymmetric Friedel-Crafts Propargylation of 3-Substituted Indoles with Propargylic Carbonates Bearing an Internal Alkyne Group

The nickel-catalyzed highly enantioselective Friedel-Crafts propargylation of 3-substituted indoles with propargylic carbonates bearing an internal alkyne group was developed. A wide array of the propargylic carbonates as well as 3-substituted indoles can be applicable to the asymmetric nickel catalysis, providing the corresponding chiral C-3 propargylated indolenine derivatives bearing two vicinal chiral centers in up to 89% yield with up to >99% ee and 94:6 dr (24 examples).

Nickel-Catalyzed Asymmetric Propargylic Amination of Propargylic Carbonates Bearing an Internal Alkyne Group

We have achieved the nickel-catalyzed asymmetric propargylic amination of propargylic carbonates bearing an internal alkyne group. A wide variety of propargylic carbonates and N-methylaniline derivatives were tolerated under the reaction conditions, providing the corresponding chiral propargylic amines in up to 97% yield with up to 97% ee.

Lewis-base-catalysed selective reductions of ynones with a mild hydride donor

Ynones are efficiently reduced with a mild hydride donor in the presence of a catalytic amount of nucleophilic phosphines. The reactions are selective 1,2-reductions that give propargyl alcohols in yields of up to 96%. It is proposed that success in these reactions depends on the activation of ynones by a Lewis base catalyst. A protic additive plays a key role in suppressing the undesired reaction pathways and accelerating the 1,2-reductions.

Trans -Hydroboration vs. 1,2-reduction: Divergent reactivity of ynones and ynoates in Lewis-base-catalyzed reactions with pinacolborane

Ynones and ynoates react with pinacolborane in a divergent manner in the presence of nucleophilic phosphine catalysts. Ynones are transformed to the corresponding propargyl alcohols in good yields with high regio- and chemoselectivity. Ynoates undergo highly regio- and stereoselective trans-hydroboration to produce E-vinylboronates. Impressive divergence in reactivity of ynones and ynoates can be traced back to the mechanistic aspects of 1,2-reduction and trans-hydroboration. A comparative analysis of the two pathways paints a complex picture in which different reaction rates control selectivity in these seemingly unrelated processes and explains how sufficiently acidic protons in the reaction mixtures can be used to steer the selectivity in different directions.

B(C6F5)3-catalyzed allylation of propargyl acetates with allylsilanes.

[reaction: see text] An efficient method for the B(C(6)F(5))(3)-catalyzed allylation of secondary propargylic alcohol derivatives with allylsilanes has been developed. This method allows for the facile synthesis of a variety of 1,5-enynes in good to high yields with a number of functionalities, such as nitro, chloro, ester, and boronic ester, being tolerated under the reaction conditions.