1344115-77-0

Basic information

• Product Name: 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 1344115-77-0
• Molecular Weight: 182.071
• Mol File: 1344115-77-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1344115-77-0)
• EPA Substance Registry System: 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(1344115-77-0)

Safety Data

• Hazardous Substances Data: 1344115-77-0(Hazardous Substances Data)

Usage

General Description

2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is a chemical compound that is commonly used in organic synthesis as a reagent for Suzuki-Miyaura cross-coupling reactions. It is a boronic ester, which means it contains a boron atom bonded to two oxygen atoms and a carbon atom. The cyclopropylmethyl group provides stability to the boronic ester, making it a useful building block in the formation of complex organic molecules. Its tetramethyl substituents also contribute to its stability and reactivity. 2-(cyclopropylmethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane is often selected for its selective reactivity and compatibility with a wide range of functional groups, making it a valuable tool in the synthesis of pharmaceuticals and agrochemicals.

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 13826-27-2 2,2'-bis(1,3,2-benzodioxaborole) 
• 7051-34-5 cyclopropylcarbinyl bromide 
• 73183-34-3 bis(pinacol)diborane 
• 778-29-0 but-3-enyl 4-methylbenzenesulfonate 
• 7766-51-0 4-iodobut-1-ene 
• 5162-44-7 1-bromo-4-butene 
• 927-73-1 3-butenyl chloride 
• 75-11-6 diiodomethane 
• 72824-04-5 2-Allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 1344115-91-8 C₁₃H₁₆ 
• 1344115-93-0 C₁₃H₁₇Cl 
• 123186-25-4 1-(2-phenylethyl)-4-penten-1-ol 
• 2516-33-8 Cyclopropylmethanol 

Relevant articles and documents

Manganese(III)-Promoted Double Carbonylation of Anilines Toward α-Ketoamides Synthesis

Employing anilines as nucleophiles in double carbonylation is a longstanding challenge. In this communication, a Mn(III)-promoted double carbonylation of alkylborates or Hantzsch esters with anilines toward the synthesis of α-ketoamides has been developed. By using easily available potassium alkyltrifluoroborates or Hantzsch esters as the starting material, and cheap and non-toxic Mn(OAc)3 ? 2H2O as the promotor, a broad range of alkyl α-ketoamide derivatives were synthesized in moderate to good yields with excellent selectivity. (Figure presented.).

TRANSGLUTAMINASE 2 (TG2) INHIBITORS

Described herein are compounds and pharmaceutical compositions containing such compounds which inhibit transglutaminase 2 (TG2). Also described herein are methods for using such TG2 inhibitors, alone or in combination with other compounds, for treating diseases or conditions that would benefit from TG2 inhibition.

Intermolecular Radical Addition to Ketoacids Enabled by Boron Activation

The intermolecular radical addition to the carbonyl group is difficult due to the facile fragmentation of the resulting alkoxyl radical. To date, the intermolecular radical addition to ketones, a valuable approach to construct quaternary carbon centers, remains a formidable synthetic challenge. Here, we report the first visible-light-induced intermolecular alkyl boronic acid addition to α-ketoacids enabled by the Lewis acid activation. The in situ boron complex formation is confirmed by various spectroscopic measurements and mechanistic probing experiments, which facilitates various alkyl boronic acid addition to the carbonyl group and prevents the cleavage of the newly formed C-C bond. Diversely substituted lactates can be synthesized from readily available alkyl boronic acids and ketoacids at room temperature merely under visible light irradiation, without any additional reagent. This boron activation approach can be extended to alkyl dihydropyridines as radical precursors with external boron reagents for primary, secondary, and tertiary alkyl radical additions. The pharmaceutically useful anticholinergic precursors are easily scaled up in multigrams under metal-free conditions in flow reactors.