70557-99-2

Basic information

• Product Name: Iodomethylboronic acid, pinacol ester
• Synonyms: Iodomethylboronic acid, pinacol ester;2-(Iodomethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 2-(iodoMethyl)-4,4,5,5-tetraMethyl-
• CAS NO: 70557-99-2
• Molecular Formula: C₇H₁₄BIO₂
• Molecular Weight: 267.90033
• Product Categories: organic boroinic acid;Organic boronic acid
• Mol File: 70557-99-2.mol
• Article Data: 12

Chemical Properties

• Boiling Point: 64-65 °C(Press: 0.2 Torr)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: Iodomethylboronic acid, pinacol ester(CAS DataBase Reference)
• NIST Chemistry Reference: Iodomethylboronic acid, pinacol ester(70557-99-2)
• EPA Substance Registry System: Iodomethylboronic acid, pinacol ester(70557-99-2)

Safety Data

• Hazardous Substances Data: 70557-99-2(Hazardous Substances Data)

Usage

Description

Iodomethylboronic acid, pinacol ester is an organic compound that serves as a versatile reagent in chemical synthesis. It is characterized by its ability to form stable boron-containing intermediates, which can be further transformed into a variety of functional groups. This unique property makes it a valuable building block in the synthesis of complex organic molecules and pharmaceuticals.

Uses

Used in Pharmaceutical Synthesis:
Iodomethylboronic acid, pinacol ester is used as a synthetic intermediate for the preparation of Taspase1 inhibitors and α-methylene-γ-butyrolactones. These compounds have potential applications in the development of therapeutic agents targeting specific enzymes and pathways involved in various diseases.
Used in Cancer Research:
In the field of cancer research, Iodomethylboronic acid, pinacol ester is used as a key component in the synthesis of α-methylene-γ-butyrolactones. These compounds have demonstrated the ability to suppress the growth of pancreatic carcinoma cells, making them promising candidates for the development of novel anticancer drugs.
Used in Organic Synthesis:
Iodomethylboronic acid, pinacol ester is employed as a reagent in various organic synthesis processes. Its ability to form stable boron-containing intermediates allows for the efficient construction of complex molecular architectures, which are essential in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

Upstream product

• 75-11-6 diiodomethane 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 76-09-5 2,3-dimethyl-2,3-butane diol 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 166330-03-6 pinacol (bromomethyl)boronate 
• 167967-38-6 diisopropyl (iodomethyl)boronate 
• 83622-42-8 2-(chloromethyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 7681-82-5 sodium iodide 
• 31103-51-2 Jodmethyllithium 
• 66080-23-7 4,4,5,5-tetramethyl-2-((phenylsulfanyl)methyl)-1,3,2-dioxaborolane 

Downstream Products

• 281681-22-9 (E)-3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)propiophenone O-methyloxime 
• 1041203-01-3 potassium dimethyl 2-acetyl-2-methyl-3-(trifluoroborato)propanoate 
• 1041202-99-6 potassium methyl 2-phenylsulfonyl-3-(trifluoroborato)propanoate 
• 1041202-98-5 potassium 2,2-bis(phenylsulfonyl)ethyltrifluoroborate 
• 1041202-96-3 potassium 2-cyano-2-phenylsulfonylethyltrifluoroborate 
• 1041203-00-2 potassium dimethyl 2-acetyl-3-(trifluoroborato)propanoate 
• 13377-46-3 exo-tricyclo[3.2.1.0(2,4)]octane 

Relevant articles and documents

PREPARATION OF HALOMETHANEBORONATES

A facile preparation of iodomethaneboronic esters is described.The key step utilizes a tin hydride reduction of dichloromethaneboronic esters.

Methyl Radical Initiated Kharasch and Related Reactions

An improved procedure to run halogen atom and related chalcogen group transfer radical additions is reported. The procedure relies on the thermal decomposition of di-tert-butylhyponitrite (DTBHN), a safer alternative to the explosive diacetyl peroxide, to produce highly reactive methyl radicals that can initiate the chain process. This mode of initiation generates byproducts that are either gaseous (N2) or volatile (acetone and methyl halide) thereby facilitating greatly product purification by either flash column chromatography or distillation. In addition, remarkably simple and mild reaction conditions (refluxing EtOAc during 30 minutes under normal atmosphere) and a low excess of the radical precursor reagent (2 equivalents) make this protocol particularly attractive for preparative synthetic applications. This initiation procedure has been demonstrated with a broad scope since it works efficiently to add a range of electrophilic radicals generated from iodides, bromides, selenides and xanthates over a range of unactivated terminal alkenes. A diverse set of radical trap substrates exemplifies a broad functional group tolerance. Finally, di-tert-butyl peroxyoxalate (DTBPO) is also demonstrated as alternative source of tert-butoxyl radicals to initiate these reactions under identical conditions which gives gaseous by-products (CO2). (Figure presented.).

Total synthesis of virgatolide B

The first total synthesis of the benzannulated spiroketal virgatolide A is presented. Key features include sp3-sp2 Suzuki coupling of an enantiomerically enriched β-trifluoroboratoamide and an aryl bromide, regioselective intramolecular carboalkoxylation, and a 1,3-anti-selective Mukaiyama aldol reaction followed by global deprotection/cyclization with regioselectivity governed by internal hydrogen bonding.