3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-[tris(1-methylethyl)silyl]-1H-pyrrole

Base Information

• Chemical Name: 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-[tris(1-methylethyl)silyl]-1H-pyrrole
• CAS No.: 365564-11-0
• Molecular Formula: C19H36BNO2Si
• Molecular Weight: 349.397
• Hs Code.: 2934999090
• European Community (EC) Number: 969-621-0
• DSSTox Substance ID: DTXSID60466340
• Nikkaji Number: J1.684.299K
• Wikidata: Q82292881
• Mol file: 365564-11-0.mol

Synonyms:365564-11-0;3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-[TRIS(1-METHYLETHYL)SILYL]-1H-PYRROLE;1-TRIISOPROPYLSILANYL-1H-PYRROLE-3-BORONIC ACID PINACOL ESTER;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole;3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole;tri(propan-2-yl)-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrol-1-yl]silane;N-TIPS PYRROLE-3-BORONIC ACID PINACOL ESTER;MFCD08063117;1-(TRIISOPROPYLSILYL)-1H-PYRROLE-3-BORONIC ACID PINACOL ESTER;C19H36BNO2Si;SCHEMBL28739;3-Ethoxycarbonylmethoxypyridine;1-(Triisopropylsilyl)pyrrole-3-boronic Acid Pinacol Ester;AMY1181;DTXSID60466340;GWFIZBYDIHGZRJ-UHFFFAOYSA-N;(1-(TRIISOPROPYLSILYL)-1H-PYRROL-3-YL)BORONIC ACID PINACOL ESTER;AKOS015946696;PB20241;Pyrrole-3-boronic acid, pinacol ester;AS-55586;SY025049;CS-0051659;FT-0755216;EN300-212692;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tri(propan-2-yl)silyl]-1H-pyrrole;3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole

Chemical Property of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-[tris(1-methylethyl)silyl]-1H-pyrrole

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 59 °C
• Boiling Point: 383.588oC at 760 mmHg
• PKA: -2.53±0.70(Predicted)
• Flash Point: 185.788oC
• PSA: 23.39000
• Density: 0.941g/cm3
• LogP: 4.81090
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 349.2608361
• Heavy Atom Count: 24
• Complexity: 413

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-(Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-pyrrole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CN(C=C2)[Si](C(C)C)(C(C)C)C(C)C

Technology Process of 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-[tris(1-methylethyl)silyl]-1H-pyrrole

There total 19 articles about 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-[tris(1-methylethyl)silyl]-1H-pyrrole 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: 98.0%

N-triisopropylsilylpyrrole (87630-35-1) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Guidance literature:

With 1-(2-borylphenyl)-2,2,6,6-tetramethylpiperidine dimer; In chloroform; at 80 ℃; for 16h;

DOI:10.1126/science.aab3591

Reference yield: 95.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + C6Cl4O2BN(C2H5)3(1+)*AlCl4(1-)=C6Cl4O2BN(C2H5)3[AlCl4] + N-triisopropylsilylpyrrole (87630-35-1) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Guidance literature:

With Et₃N; In dichloromethane; byproducts: Et3NH-AlCl4; to borenium cation made in situ (in Schlenk, to soln. Et2N (CH2Cl2) added Cl4CatBCl, AlCl3; stirred) at 20°C arene added (CH2Cl2); excessEt3N added; pinacol added; stirred for 32 h;; (11)B (1H) NMR; volatiless remowed under vac; extracted (hexane); filtered through silica; removal of solvent;;

DOI:10.1002/anie.201006196

Reference yield: 90.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 3-(1,3,2-benzodioxaborolan-2-yl)-1-(triisopropylsilyl)-1H-pyrrole → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0)

Guidance literature:

With triethylamine; In dichloromethane; for 3h;

upstream raw materials:

N-triisopropylsilylpyrrole

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

bis(pinacol)diborane

3-bromo-1-triisopropylsilanyl-1H-pyrrole

Downstream raw materials:

3-(2-nitrophenyl)-1-(triisopropylsilyl)-1H-pyrrole

2-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

3-(3'-chloro-2'-nitrophenyl)-N-(TIPS)pyrrole

Refernces

• 1、 Kaplan, Anna R.,Musaev, Djamaladdin G.,Wuest, William M.. "Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity". . p. 544 - 551. Retrieved 2021/03/03.
• 2、 -. "BENZOTHIAZOL COMPOUNDS AND METHODS USING THE SAME FOR TREATING NEURODEGENERATIVE DISORDERS". . . Retrieved 2019/04/18.