159087-40-8

Basic information

• Product Name: 2-(Hex-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• Synonyms: 2-(Hex-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS NO: 159087-40-8
• Molecular Formula: C₁₂H₂₁BO₂
• Molecular Weight: 208.10494
• Mol File: 159087-40-8.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: 2-(Hex-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Hex-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(159087-40-8)
• EPA Substance Registry System: 2-(Hex-1-yn-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane(159087-40-8)

Safety Data

• Hazardous Substances Data: 159087-40-8(Hazardous Substances Data)

Usage

Structure

硼原子与两个氧原子和具有三键的碳链结合。 该化合物的结构包括一个与两个氧原子和具有三键的碳链结合的硼原子。

用途

作为有机合成反应中的试剂，特别是用于形成碳-碳键。 该化合物通常用作有机合成反应中的试剂，特别是用于形成碳-碳键。

稳定性

该化合物以其稳定性和惰性而闻名，这使得它成为创建复杂有机分子的有价值工具。 该化合物以其稳定性和惰性而闻名，这使得它成为创建复杂有机分子的有价值工具。

应用

该化合物在制药、农药和材料科学等广泛应用中都很有用。 该化合物在制药、农药和材料科学等广泛应用中都很有用。

合成方法

该化合物通常用于开发有机化学中的新合成方法和策略。 该化合物通常用于开发有机化学中的新合成方法和策略。

Upstream product

• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 1086138-68-2 C₁₀H₇BO₃ 
• 693-02-7 hex-1-yne 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 

Downstream Products

• 99107-70-7 2-butyl-4-methoxynaphthalen-1-ol 
• 252863-65-3 2-butyl-4-methoxy-3-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)naphthalen-1-ol 
• 1016546-85-2 (E)-1-phenyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-hept-2-en-1-ol 
• 1002334-09-9 4-butyl-1-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 1002334-08-8 3-butyl-1-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole 
• 910875-13-7 methyl 4-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 910875-10-4 methyl 3-butyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 
• 509152-29-8 5-butyl-3-methoxy-4-phenyl-isoxazole 
• 509152-22-1 3-bromo-5-butyl-4-phenyl-isoxazole 
• 509152-27-6 5-butyl-3-chloro-4-phenyl-isoxazole 

Relevant articles and documents

Ag(I)-catalyzed C-H borylation of terminal alkynes

An efficient Ag(I)-catalyzed borylation method of terminal alkynes is reported. The obtained borylated alkynes are shown to engage in C-Br, C-CN, C-N, and C-C bond formation with various reaction partners. Meanwhile the Ag(I) catalyst could be regenerated in the presence of PPh3 and BF3.

Method for removing hydroboration of aluminum chloride catalytic terminal group alkyne

The invention discloses a hydroboration method of an aluminum chloride catalytic terminal group alkyne, and belongs to the technical field of boronation of terminal alkynes. To the method, the terminal group alkyne is added into the aluminum chloride with

Ru-Catalyzed Geminal Hydroboration of Silyl Alkynes via a New gem-Addition Mechanism

While 1,2-addition represents the most common mode of alkyne hydroboration, herein we describe a new 1,1-hydroboration mode. It is the first demonstration of gem-(H,B) addition to an alkyne triple bond. With the superior [CpRu(MeCN)3]PF6 catalyst, a range of silyl alkynes reacted efficiently with HBpin under mild conditions to form various synthetically useful silyl vinyl boronates with complete stereoselectivity and broad functional group compatibility. An extension to germanyl alkynes and the hydrosilylation of alkynyl boronates toward the same type of products were also achieved. Mechanistically, this process features a new pathway featuring gem-(H,B) addition to form the key α-boryl-α-silyl Ru-carbene intermediate followed by silyl migration. It is believed that the orbital interaction between boron and Cβ in the coplanar relationship between the boron atom and the ruthenacyclopropene ring preceding boron migration is responsible for the new reactivity. Control experiments and DFT (including molecular dynamics) calculations provided important insights into the mechanism, which excluded the involvement of a metal vinylidene intermediate. This study represents a new step forward not only for alkyne hydroboration but also for other geminal additions of alkynes.