4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane

Base Information

• Chemical Name: 4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane
• CAS No.: 476004-80-5
• Molecular Formula: C11H19BO3S
• Molecular Weight: 224.132
• Hs Code.: 2934999090
• European Community (EC) Number: 891-530-9
• DSSTox Substance ID: DTXSID80473556
• Nikkaji Number: J1.768.871E
• Wikidata: Q82303039
• Mol file: 476004-80-5.mol

Synonyms:476004-80-5;4,4,5,5-tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane;5-Methylthiophene-2-boronic acid pinacol ester;5-Methylthiophene-2-boronic acid, pinacol ester;5-METHYLTHIOPHEN-2-BORONIC ACID PINACOL ESTER;MFCD05664108;4,4,5,5-tetramethyl-2-(5-methyl-2-thienyl)-1,3,2-dioxaborolane;5-(2-Methylthiophene)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;1,3,2-Dioxaborolane, 4,4,5,5-tetramethyl-2-(5-methyl-2-thienyl)-;SCHEMBL30846;(5-METHYLTHIOPHEN-2-YL)BORONIC ACID PINACOL ESTER;DTXSID80473556;LTOLNTYOBPPFLS-UHFFFAOYSA-N;BCP30230;AKOS015943349;AB22291;DS-17400;SY102349;CS-0041968;EN300-156336;A872114;5-Methylthiophene-2-boronic acid pinacol ester,95%;5-Methylthiophene-2-boronic acid pinacol ester, 95%;Z1336745165;4,4,5,5-tetramethyl-2-(5-methyl-thiophen-2-yl)-[1,3,2]dioxaborolane;4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane

Chemical Property of 4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane

Chemical Property:

• Vapor Pressure: 0.00125mmHg at 25°C
• Refractive Index: 1.5
• Boiling Point: 308.2°Cat760mmHg
• Flash Point: 140.2°C
• PSA: 46.70000
• Density: 1.06g/cm³
• LogP: 2.35570
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 224.1042311
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

97% ^*data from raw suppliers

4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(S2)C
• Uses: 5-Methylthiophene-2-boronic acid pinacol ester can be used as a reactant: In the palladium-catalyzed Suzuki coupling reaction for the preparation of heteroaryl derivatives. To synthesize N-(4-methylpyridin-2-yl)thiophene-2-carboxamide analog as potential inhibitor of acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). To prepare organic recyclable mechanoluminescent luminogen via Wittig and Suzuki reactions.

Technology Process of 4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane

There total 28 articles about 4,4,5,5-Tetramethyl-2-(5-methylthiophen-2-yl)-1,3,2-dioxaborolane which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

2-Methylthiophene (554-14-3) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylthiophene (476004-80-5)

Guidance literature:

2-Methylthiophene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 2h; Inert atmosphere; Schlenk technique;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 8h; Inert atmosphere; Schlenk technique;

DOI:10.1021/om400636r

Reference yield: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + (5-methylthiophen-2-yl)boronic acid (162607-20-7) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylthiophene (476004-80-5)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1002/jhet.931

Reference yield: 88.0%

2-Methylthiophene (554-14-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2-methylthiophene (476004-80-5)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tetrahydrofuran; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol301570t

upstream raw materials:

2-Methylthiophene

bis(pinacol)diborane

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

(dippe)Ir(Bpin)3

Downstream raw materials:

2-methyl-5-(3-(trifluoromethyl)phenyl)thiophene

3-benzyl-1,3,4-trimethyl-6-[1-[2-(5-methylthiophen-2-yl)pyridin-3-yl]meth-(Z)-ylidene]piperazine-2,5-dione

4-(4-methoxyphenyl)-7-(5-methylthiophen-2-yl)-2,1,3-benzothiadiazole

2,8-dimethyl-5-(2-(5-methylthiophen-2-yl)phenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole