5-BROMOTHIOPHENE-2-BORONIC ACID

Base Information

• Chemical Name: 5-BROMOTHIOPHENE-2-BORONIC ACID
• CAS No.: 162607-17-2
• Molecular Formula: C4H4BBrO2S
• Molecular Weight: 206.856
• Hs Code.: 29349990
• European Community (EC) Number: 678-207-6
• DSSTox Substance ID: DTXSID00370210
• Nikkaji Number: J1.085.491A
• Wikidata: Q72513019
• Mol file: 162607-17-2.mol

Synonyms:Boronicacid, (5-bromo-2-thienyl)- (9CI);5-Bromo-2-thienylboronic acid;

Chemical Property of 5-BROMOTHIOPHENE-2-BORONIC ACID

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.93E-05mmHg at 25°C
• Melting Point: 95-100 °C(lit.)
• Refractive Index: 1.629
• Boiling Point: 342.3 °C at 760 mmHg
• PKA: 8.20±0.53(Predicted)
• Flash Point: 160.8 °C
• PSA: 68.70000
• Density: 1.87 g/cm³
• LogP: 0.19040
• Storage Temp.: 0-6°C
• Water Solubility.: Slightly soluble in water
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 205.92084
• Heavy Atom Count: 9
• Complexity: 103

Purity/Quality:

99%, ^*data from raw suppliers

5-Bromo-2-thiopheneboronic Acid (contains varying amounts of Anhydride) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC=C(S1)Br)(O)O
• Uses: Reactant involved in:Suzuki coupling reactions for the synthesis of benzotriazole-containing organic sensitizers and meso-Polyarylamide-BODIPY hybridsSuzuki-Miyaura coupling for the synthesis of ratanhineMicrowave-assisted Sonogashira reactions for the synthesis of ethynylarylboronates

Technology Process of 5-BROMOTHIOPHENE-2-BORONIC ACID

There total 5 articles about 5-BROMOTHIOPHENE-2-BORONIC ACID 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:

2,5-dibromothiophen (3141-27-3) → (5-bromothiophene-2-yl)boronic acid (162607-17-2)

Guidance literature:

With n-butyllithium; diethyl ether; at -60 ℃; anschliessend Behandeln mit Tributylborat und Behandeln des Reaktionsgemisches mit wss. Salzsaeure;

Reference yield:

2,5-dibromothiophen (3141-27-3) + Trimethyl borate (121-43-7,63156-11-6) → (5-bromothiophene-2-yl)boronic acid (162607-17-2)

Guidance literature:

2,5-dibromothiophen; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

Trimethyl borate; In tetrahydrofuran; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1039/c5ra05226b

Reference yield:

thiophene boronic acid (6165-68-0) → (5-bromothiophene-2-yl)boronic acid (162607-17-2)

Guidance literature:

With chloroform; bromine; at -40 ℃;

upstream raw materials:

5-bromo-[2]thienyl lithium

diethyl ether

boric acid tributyl ester

2,5-dibromothiophen

Downstream raw materials:

5-bromo-2-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)thiophene

2-phenyl-5-(pyridin-2-yl)thiophene

5'-{4-(N,N-diphenylamino)stylyl}-2,2'-bithiophene-5-carbaldehyde

potassium (5-bromothiophen-2-yl)trifluoroboranuide

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