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3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester is a specialized chemical compound that features a boronic ester and thiophene group within its chemical structure. 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester is known for its ability to participate in cross-coupling reactions with a variety of aryl iodides and bromides, making it a valuable intermediate in organic synthesis. As an organoboron compound, it is particularly notable for its use in palladium-catalyzed coupling reactions, which are a cornerstone in modern organic chemistry. 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester's solubility, stability, and reactivity are influenced by factors such as temperature and the surrounding chemical environment, and detailed chemical data and safety information should be obtained from the manufacturer or scientific databases.

1227664-10-9

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1227664-10-9 Usage

Uses

Used in Organic Synthesis:
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester is used as a synthetic intermediate for the preparation of various complex organic molecules. Its reactivity in cross-coupling reactions allows for the formation of new carbon-carbon bonds, which is essential in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester is used as a key building block in the synthesis of drug candidates. Its involvement in palladium-catalyzed coupling reactions enables the creation of diverse molecular structures with potential therapeutic applications.
Used in Materials Science:
3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester is used as a component in the development of advanced materials, such as organic electronic devices and specialty polymers. Its incorporation into these materials can impart unique properties, such as improved conductivity or enhanced stability.
Used in Research and Development:
In academic and industrial research settings, 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-thiophenecarboxylic acid methyl ester is used as a model compound to study the mechanisms of cross-coupling reactions and to develop new catalytic systems for these transformations. This research contributes to the broader understanding of organoboron chemistry and its applications in various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 1227664-10-9 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,2,2,7,6,6 and 4 respectively; the second part has 2 digits, 1 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1227664-10:
(9*1)+(8*2)+(7*2)+(6*7)+(5*6)+(4*6)+(3*4)+(2*1)+(1*0)=149
149 % 10 = 9
So 1227664-10-9 is a valid CAS Registry Number.

1227664-10-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylate

1.2 Other means of identification

Product number -
Other names 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiophene-2-carboxylic acid methyl ester

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1227664-10-9 SDS

1227664-10-9Downstream Products

1227664-10-9Relevant academic research and scientific papers

Silyl phosphorus and nitrogen donor chelates for homogeneous ortho borylation catalysis

Ghaffari, Behnaz,Preshlock, Sean M.,Plattner, Donald L.,Staples, Richard J.,Maligres, Peter E.,Krska, Shane W.,Maleczka, Robert E.,Smith, Milton R.

supporting information, p. 14345 - 14348 (2014/12/10)

Ir catalysts supported by bidentate silyl ligands that contain P- or N-donors are shown to effect ortho borylations for a range of substituted aromatics. The substrate scope is broad, and the modular ligand synthesis allows for flexible catalyst design.

Ester-directed regioselective borylation of heteroarenes catalyzed by a silica-supported iridium complex

Kawamorita, Soichiro,Ohmiya, Hirohisa,Sawamura, Masaya

experimental part, p. 3855 - 3858 (2010/09/04)

Figure presented The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene, pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.

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