Boronic acid, 1,2-phenylenebis- (9CI)

Base Information

• Chemical Name: Boronic acid, 1,2-phenylenebis- (9CI)
• CAS No.: 13506-83-7
• Molecular Formula: C6H8 B2 O4
• Molecular Weight: 165.749
• Hs Code.: 2916399090
• Mol file: 13506-83-7.mol

Synonyms:o-Benzenediboronicacid (8CI)

Chemical Property of Boronic acid, 1,2-phenylenebis- (9CI)

Chemical Property:

• Melting Point: 120-123 °C
• Boiling Point: 446.3±55.0 °C(Predicted)
• PKA: 8.18±0.53(Predicted)
• PSA: 80.92000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: -2.95380
• Storage Temp.: 2-8°C

Purity/Quality:

99%, ^*data from raw suppliers

1,2-Phenylenediboronicacid 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Boronic acid, 1,2-phenylenebis- (9CI)

There total 4 articles about Boronic acid, 1,2-phenylenebis- (9CI) 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: 83.1%

Triisopropyl borate (5419-55-6) + 2,3-dibromobenzene (583-53-9) → [2-(dihydroxyboranyl)phenyl]boronic acid (13506-83-7)

Guidance literature:

2,3-dibromobenzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h; Inert atmosphere;

Triisopropyl borate; With water; In tetrahydrofuran; hexane; at 20 ℃;

Reference yield: 76.0%

Trimethyl borate (121-43-7,63156-11-6) + 2-(2'-bromophenyl)-6-butyl[1,3,6,2]dioxazaborocan (1008106-85-1) → [2-(dihydroxyboranyl)phenyl]boronic acid (13506-83-7)

Guidance literature:

2-(2'-bromophenyl)-6-butyl[1,3,6,2]dioxazaborocan; With n-butyllithium; In tetrahydrofuran; at -90 - -75 ℃; for 0.333333h;

Trimethyl borate; at -85 ℃; for 0.333333h;

With hydrogenchloride; In water; at -30 ℃;

DOI:10.1021/om500104w

Reference yield: 76.0%

→ [2-(dihydroxyboranyl)phenyl]boronic acid (13506-83-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -70 ℃; for 1h; Inert atmosphere;

With Trimethyl borate; In tetrahydrofuran; cyclohexane; at 20 ℃; for 1h; Inert atmosphere;

upstream raw materials:

Trimethyl borate

2-(2'-bromophenyl)-6-butyl[1,3,6,2]dioxazaborocan

tetrahydroxydiboron

2-iodochlorobenzene

Downstream raw materials:

benzene-1,2-diol

1,2-bis(4,4,5,5-tetramethyl-[1,3,2]dioxabororan-2-yl)benzene

4-bromo-benzenesulfonic acid-(4-chloro-anilide)

phthalonitrile

Refernces

• 1、 Zernickel, Anna,Du, Weiyuan,Ghorpade, Seema A.,Sawant, Dinesh N.,Makki, Arwa A.,Sekar, Nagaiyan,Eppinger, J?rg. "Bedford-type palladacycle-catalyzed miyaura borylation of aryl halides with tetrahydroxydiboron in water". . p. 1842 - 1851. Retrieved 2018/02/23.
• 2、 Seven, Oemer,Bolte, Michael,Lerner, Hans-Wolfram,Wagner, Matthias. "High-yield syntheses and reactivity studies of 1,2-diborylated and 1,2,4,5-tetraborylated benzenes". . p. 1291 - 1299. Retrieved 2014/04/03.