(E)-Styrylboronic acid

Base Information

• Chemical Name: (E)-Styrylboronic acid
• CAS No.: 6783-05-7
• Molecular Formula: C8H9BO2
• Molecular Weight: 147.969
• Hs Code.: 29310099
• European Community (EC) Number: 691-946-9
• DSSTox Substance ID: DTXSID201346540
• Nikkaji Number: J271.000E,J813.854K
• ChEMBL ID: CHEMBL559289
• Mol file: 6783-05-7.mol

Synonyms:6783-05-7;(E)-Styrylboronic acid;styrylboronic acid;E-Phenylethenylboronic acid;trans-2-Phenylvinylboronic acid;4363-35-3;2-Phenylvinylboronic Acid;[(E)-2-phenylethenyl]boronic acid;(Z/E)-Styrylboronic acid;Trans-Beta-Styreneboronic Acid;Boronic acid, [(1E)-2-phenylethenyl]-;CHEMBL559289;Boronic acid,B-[(1E)-2-phenylethenyl]-;[(E)-styryl]boronic acid;((E)-Styryl)boronic acid;styryl boronic acid;(E)-Phenylethenylboronic acid;MFCD00963621;trans-styryl boronic acid;D0F7QZ;(E)-phenylvinylboronic acid;E-phenylethenyl boronic acid;trans-phenylvinyl-boronic acid;(2-phenylethenyl)boronic acid;SCHEMBL144460;trans-2-Phenylvinylboronicacid;(E)-2-Phenylvinylboronic acid;(E)-phenylethenyl boronic acid;trans-beta-styrene boronic acid;(E)-STYRENEBORONIC ACID;TRANS-STYRENEBORONIC ACID;(E)-2-phenylethenylboronic acid;(E-2-phenylethenyl]boronic acid;trans-2-phenylvinyl boronic acid;trans-2-phenylvinyl-boronic acid;(trans-Phenylethenyl)boronic acid;(E)-2-phenylethenyl boronic acid;[(E)-2-phenylvinyl]boronic acid;VKIJXFIYBAYHOE-VOTSOKGWSA-N;DTXSID201346540;(E)-2-Phenyl-ethene boronic acid;TRANS-?-STYRENEBORONIC ACID;(E)-(2-Phenylethenyl)boronic acid;STR09885;TRANS-|A-STYRENEBORONIC ACID;[(1Z)-2-phenylethenyl]boronic acid;BDBM50294578;TRANS-PHENYLETHENYLBORONIC ACID;TRANS-PHENYLVINYL BORONIC ACID;AKOS015855910;trans-2-Phenylvinylboronic acid, 97%;(E)-2-PHENYL-ETHENEBORONIC ACID;NCGC00249460-01;NCGC00249460-02;AS-75653;CS-0106351;EN300-187909;EN300-1242089;A853401;Z2315575087

Chemical Property of (E)-Styrylboronic acid

Chemical Property:

• Appearance/Colour: Brown granular powder
• Melting Point: 146-156 °C(lit.)
• Boiling Point: 315.9 °C at 760 mmHg
• PKA: 9.38±0.43(Predicted)
• Flash Point: 144.9 °C
• PSA: 40.46000
• Density: 1.13 g/cm³
• LogP: 0.71180
• Storage Temp.: 0-6°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 148.0695597
• Heavy Atom Count: 11
• Complexity: 128

Purity/Quality:

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

[(E)-2-Phenylvinyl]boronicAcid ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C=CC1=CC=CC=C1)(O)O
• Isomeric SMILES: B(/C=C/C1=CC=CC=C1)(O)O
• Uses: E-Phenylethenylboronic acid is a reagent used for? ;Palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions 1 Rhodium (Rh)-catalyzed intramolecular amination of aryl azides 2 Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction 3 Copper (Cu)-mediated cyanation 4 Rhodium (Rh)-catalyzed asymmetric addition 5 Diastereoselective synthesis via iridium (Ir)-catalyzed addition 6 Palladium (Pd)-catalyzed cascade cyclization 7 Reagent used in Preparation of ? ;Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reactio trans-beta-Styrylboronic acid as reagent is used for palladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions, diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction and rhodium (Rh)-catalyzed intramolecular amination of aryl azides. It is also used as reagent in preparation of optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction and amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization. Reagent used forPalladium (Pd)-catalyzed Suzuki-Miyaura coupling reactions Rhodium (Rh)-catalyzed intramolecular amination of aryl azides Diastereoselective synthesis via Pd-catalyzed Heck-Suzuki cascade reaction Copper (Cu)-mediated cyanation Rhodium (Rh)-catalyzed asymmetric addition Diastereoselective synthesis via iridium (Ir)-catalyzed addition Palladium (Pd)-catalyzed cascade cyclization Reagent used in Preparation of Optically active unsaturated amino acids by diastereoselective Petasis borono-Mannich reaction Amino alcohol dienes via Petasis 3-component reaction using Ru-catalyzed ring-closing metathesis and isomerization

Technology Process of (E)-Styrylboronic acid

There total 23 articles about (E)-Styrylboronic 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: 100.0%

phenylacetylene (536-74-3) → trans-2-phenylvinylboronic acid (6783-05-7)

Guidance literature:

With benzo[1,3,2]dioxaborole; In tetrahydrofuran; Heating;

DOI:10.1016/j.bmcl.2005.03.098

Reference yield: 91.0%

(E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole (6783-04-6,57001-92-0,96794-40-0) → trans-2-phenylvinylboronic acid (6783-05-7)

Guidance literature:

With water; at 70 ℃; for 1h;

DOI:10.1016/j.bmc.2004.01.051

Reference yield: 91.0%

potassium styryltrifluoroborate → Dihydroxy-styryl-boran (4363-35-3,6783-05-7,60806-02-2)

Guidance literature:

With aluminum oxide; water; at 70 ℃; for 0.25h; Microwave irradiation;

DOI:10.1016/j.tetlet.2009.09.008

upstream raw materials:

dichloro(E-2-phenylethen-1-yl)borane

tris(ethylenedioxyboryl)methane

benzaldehyde

(E)-2-(2'-phenylethenyl)-1,3,2-benzodioxaborole

Downstream raw materials:

(1R,2S)-(-)-2-phenyl-1-cyclopropane

(1S,2R)-2-phenyl-1-cyclopropanol

5-<(E)-2-phenylethenyl>-2'-deoxyuridine

styrene

Refernces

• 1、 Boylan, Amy,Li, Jian-Yuan,Lundy, Brian J.,May, Jeremy A.,Nguyen, Thien S.,Sundstrom, Sasha,Vallakati, Ravikrishna. "Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones". . . Retrieved 2021/06/16.
• 2、 Havare, Nizam,Kano, Naokazu,Morokuma, Keiji,O'Brien, Nathan J.,Ramozzi, Romain,Uematsu, Ryohei. "Synthesis, Structure and Reactivities of Pentacoordinated Phosphorus–Boron Bonded Compounds". . . Retrieved 2020/04/29.