2-(2,5-Dibromothiophen-3-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Base Information

• Chemical Name: 2-(2,5-Dibromothiophen-3-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
• CAS No.: 942070-22-6
• Molecular Formula: C₁₀H₁₃BBr₂O₂S
• Molecular Weight: 367.897
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID60700014
• Nikkaji Number: J2.900.226F
• Wikidata: Q72465146
• Mol file: 942070-22-6.mol

Synonyms:942070-22-6;2-(2,5-DIBROMOTHIOPHEN-3-YL)-4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLANE;MFCD12405469;2-(2,5-dibromo-3-thienyl)-4,4,5,5-tetramethyl-1,3,2-Dioxaborolane;C10H13BBr2O2S;2,5-Dibromothiophene-3-boronic acid pinacol ester;DTXSID60700014;(2,5-DIBROMOTHIOPHEN-3-YL)BORONIC ACID PINACOL ESTER;AMY22022;AKOS016006564;DS-18455;SY108352;CS-0101386;FT-0749353;F30017;A859522

Chemical Property of 2-(2,5-Dibromothiophen-3-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Chemical Property:

• Melting Point: 72-73 °C
• Boiling Point: 371℃
• Flash Point: 178℃
• PSA: 46.70000
• Density: 1.66
• LogP: 3.57230
• Storage Temp.: 2-8°C(protect from light)
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 367.90756
• Heavy Atom Count: 16
• Complexity: 272

Purity/Quality:

98%Min ^*data from raw suppliers

2-(2,5-Dibromothiophen-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane ^*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=C(SC(=C2)Br)Br

Technology Process of 2-(2,5-Dibromothiophen-3-YL)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

There total 4 articles about 2-(2,5-Dibromothiophen-3-YL)-4,4,5,5-tetramethyl-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: 85.0%

4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane (214360-70-0) → pinacol 2,5-dibromo-3-thiopheneylboronate (942070-22-6)

Guidance literature:

With gold(III) chloride; N-Bromosuccinimide; In 1,2-dichloro-ethane; at 70 ℃; for 24h; regioselective reaction;

DOI:10.1021/ol102350v

Reference yield: 84.0%

2,5-dibromothiophen (3141-27-3) + bis(pinacol)diborane (73183-34-3) → pinacol 2,5-dibromo-3-thiopheneylboronate (942070-22-6)

Guidance literature:

bis(pinacol)diborane; With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 4,4'-di-tert-butyl-2,2'-bipyridine; In tert-butyl methyl ether; Inert atmosphere;

2,5-dibromothiophen; In tert-butyl methyl ether; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1021/ol901306m

Reference yield: 65.0%

N-Bromosuccinimide (128-08-5) + 4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane (214360-70-0) → pinacol 2,5-dibromo-3-thiopheneylboronate (942070-22-6)

Guidance literature:

In N,N-dimethyl-formamide; at 20 ℃; for 14h;

DOI:10.1016/j.tetlet.2014.06.003

upstream raw materials:

2,5-dibromothiophen

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

4,4,5,5-tetramethyl-2-thiophen-3-yl-[1,3,2]dioxaborolane

bis(pinacol)diborane

Refernces

• 1、 Kamei, Toshiyuki,Ishibashi, Aoi,Shimada, Toyoshi. "Metal-free halogenation of arylboronate with N-halosuccinimide". . p. 4245 - 4247. Retrieved 2014/07/22.
• 2、 Harrisson, Peter,Morris, James,Marder, Todd B.,Steel, Patrick G.. "Microwave-accelerated iridium-catalyzed borylation of aromatic C-H bonds". supporting information; experimental part. p. 3586 - 3589. Retrieved 2011/02/22.