355408-55-8

Basic information

• Product Name: 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane
• Synonyms: 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane;Thiophene-2-boronic acid, neopentyl glycol ester
• CAS NO: 355408-55-8
• Molecular Formula: C₉H₁₃BO₂S
• Molecular Weight: 196.07
• Mol File: 355408-55-8.mol
• Article Data: 14

Chemical Properties

• Melting Point: 97-98 °C
• Boiling Point: 294.5±13.0 °C(Predicted)
• Appearance: /
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane(355408-55-8)
• EPA Substance Registry System: 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane(355408-55-8)

Safety Data

• Hazardous Substances Data: 355408-55-8(Hazardous Substances Data)

Usage

General Description

5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane is a chemical compound with the molecular formula C8H11BO2S. It is a boronic acid derivative that contains a boron atom, two methyl groups, a thiophene ring, and a dioxaborinane ring. 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane is commonly used as a reagent in organic synthesis, particularly in the Suzuki-Miyaura coupling reaction to form carbon-carbon bonds. It has also been employed in the development of pharmaceuticals and materials chemistry. 5,5-Dimethyl-2-(thiophen-2-yl)-1,3,2-dioxaborinane is considered to be a versatile and valuable building block in the field of organic chemistry.

Upstream product

• 201733-56-4 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane 
• 668987-38-0 5,5-dimethyl-1,3,2-dioxaborinane 
• 1003-09-4 2-bromothiophene 
• 126-30-7 2,2-Dimethyl-1,3-propanediol 
• 3141-27-3 2,5-dibromothiophen 
• 96-43-5 2-thienyl chloride 
• 6165-68-0 thiophene boronic acid 
• 188290-36-0 thiophene 

Downstream Products

• 17595-86-7 methyl 4-(2-thienyl)benzoate 
• 35294-37-2 1-(4-(thiophen-2-yl)phenyl)ethanone 
• 5380-42-7 thiophene-2-carboxylic acid methyl ester 
• 115933-15-8 2-(4-(trifluoromethyl)phenyl)thiophene 
• 3319-99-1 2'-(2-thienyl)pyridine 
• 1259553-77-9 (S)-3-(2-phenylbut-3-en-2-yl)thiophene 
• 1380226-49-2 N,N-dibenzylthienyl-2-amine 
• 4861-61-4 2-dodecylthiophene 
• 527-72-0 2-thiophenylcarboxylic acid 
• 355408-49-0 2,10-dihydro-10-methyl-2,2-diphenyl-8-(2-thienyl)pyrano[2,3-b]carbazole 

Relevant articles and documents

Ni-Catalyzed Borylation of Aryl Sulfoxides

A nickel/N-heterocyclic carbene (NHC) catalytic system has been developed for the borylation of aryl sulfoxides with B2(neop)2 (neop=neopentyl glycolato). A wide range of aryl sulfoxides with different electronic and steric properties were converted into the corresponding arylboronic esters in good yields. The regioselective borylation of unsymmetric diaryl sulfoxides was also feasible leading to borylation of the sterically less encumbered aryl substituent. Competition experiments demonstrated that an electron-deficient aryl moiety reacts preferentially. The origin of the selectivity in the Ni-catalyzed borylation of electronically biased unsymmetrical diaryl sulfoxide lies in the oxidative addition step of the catalytic cycle, as oxidative addition of methoxyphenyl 4-(trifluoromethyl)phenyl sulfoxide to the Ni(0) complex occurs selectively to give the structurally characterized complex trans-[Ni(ICy)2(4-CF3-C6H4){(SO)-4-MeO-C6H4}] 4. For complex 5, the isomer trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I was structurally characterized in which the phenyl sulfinyl ligand is bound via the oxygen atom to nickel. In solution, the complex trans-[Ni(ICy)2(C6H5)(OSC6H5)] 5-I is in equilibrium with the S-bonded isomer trans-[Ni(ICy)2(C6H5)(SOC6H5)] 5, as shown by NMR spectroscopy. DFT calculations reveal that these isomers are separated by a mere 0.3 kJ/mol (M06/def2-TZVP-level of theory) and connected via a transition state trans-[Ni(ICy)2(C6H5)(η2-{SO}-C6H5)], which lies only 10.8 kcal/mol above 5.

Simple base-free Miyaura-type borylation of triarylantimony diacetates with tetra(alkoxo)diborons under aerobic conditions

The reaction of triarylantimony diacetates with tetra(alkoxo)diborons in the presence of PdCl2(PPh3)2 (1 mol%) catalyst resulted in the Miyaura-type B-arylation to form arylboronates in moderate to good yields under base-free conditions. In the present reaction, two of the three aryl groups of antimony reagent were transferred to the coupling products when the reaction was carried out under aerobic conditions, although only one of the three aryl group of the antimony reagent was involved under an argon atmosphere. The broad scope of the reaction was demonstrated by using a variety of triarylantimony diacetates with sterically hindered aryl groups and highly reactive p-bromo-functionalized aryl derivatives.

Copper-catalyzed amination of arylboronates with N,N-dialkylhydroxylamines

A tolerant coupling: The title reaction has been developed to deliver arylamines (see scheme; Bz=benzoyl, dppbz=1,2-bis(diphenylphosphino)benzene). The catalysis is based on electrophilic, umpolung amination and enables the use of secondary acyclic amines. Various functional groups are tolerated, thus opening up a new substrate class for the Chan-Lam-type coupling.