trans-2-(4-Methoxyphenyl)vinylboronic acid

Base Information

• Chemical Name: trans-2-(4-Methoxyphenyl)vinylboronic acid
• CAS No.: 72316-18-8
• Molecular Formula: C9H11 B O3
• Molecular Weight: 177.996
• Hs Code.: 2931900090
• DSSTox Substance ID: DTXSID601249261
• Nikkaji Number: J1.915.546C,J2.512.630K
• ChEMBL ID: CHEMBL2315707
• Mol file: 72316-18-8.mol

Synonyms:72316-18-8;trans-2-(4-Methoxyphenyl)vinylboronic acid;(E)-(4-Methoxystyryl)boronic acid;[(E)-2-(4-methoxyphenyl)ethenyl]boronic acid;(E)-4-Methoxystyrylboronic acid;TRANS-2-(4-METHOXYPHENYL)-;4-Methoxystyrylboronic Acid;[(E)-2-(4-methoxyphenyl)vinyl]boronic acid;(E)-(4-Methoxystyryl)boronicacid;SCHEMBL542740;CHEMBL2315707;DTXSID601249261;[(E)-4-Methoxystyryl]boronic acid;XCA31618;MFCD04039879;AKOS015851876;AS-65652;(E)-2-(4-methoxyphenyl)vinylboronic acid;CS-0110014;trans-2-(4-methoxyphenyl)vinyl boronic acid;[trans-2-(4-Methoxyphenyl)ethenyl]boronic acid;D76970;[(1E)-2-(4-methoxyphenyl)ethenyl]boronic acid;EN300-1242088;A866286;boronic acid, [(E)-2-(4-methoxyphenyl)ethenyl]-;TRANS-2-(4-METHOXYPHENYL)VINYLBORONICACID;trans-2-(4-Methoxyphenyl)vinylboronic acid, >=95%

Chemical Property of trans-2-(4-Methoxyphenyl)vinylboronic acid

Chemical Property:

• Vapor Pressure: 3.15E-06mmHg at 25°C
• Melting Point: 140-144 °C(lit.)
• Refractive Index: 1.568
• Boiling Point: 373.1°C at 760 mmHg
• PKA: 9.61±0.43(Predicted)
• Flash Point: 179.4°C
• PSA: 49.69000
• Density: 1.149g/cm³
• LogP: 0.72040
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 178.0801244
• Heavy Atom Count: 13
• Complexity: 162

Purity/Quality:

97% ^*data from raw suppliers

trans-2-(4-Methoxyphenyl)vinylboronic acid ≥95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C=CC1=CC=C(C=C1)OC)(O)O
• Isomeric SMILES: B(/C=C/C1=CC=C(C=C1)OC)(O)O
• Uses: Reactant involved in:? ;Enantioselective conjugate addition reactions with indole-appended enones1? ;Liebeskind-Srogl cross-coupling reactions2? ;Petasis asymmetric dihydroxylation for synthesis of (dihydroxy)homotyrosines3? ;Copper-catalyzed trifluoromethylation4? ;Asymmetric Michael addition with hydroxycinnamaldehydes5? ;Cobalt-catalyzed coupling for synthesis of phenylbutenylheteroarenes6 Reactant involved in:Enantioselective conjugate addition reactions with indole-appended enonesLiebeskind-Srogl cross-coupling reactionsPetasis asymmetric dihydroxylation for synthesis of (dihydroxy)homotyrosinesCopper-catalyzed trifluoromethylationAsymmetric Michael addition with hydroxycinnamaldehydesCobalt-catalyzed coupling for synthesis of phenylbutenylheteroarenes

Technology Process of trans-2-(4-Methoxyphenyl)vinylboronic acid

There total 6 articles about trans-2-(4-Methoxyphenyl)vinylboronic 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%

4-methoxyphenylacetylen (768-60-5) → (E)-2-(4-methoxyphenyl)vinylboronic acid (72316-18-8)

Guidance literature:

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

DOI:10.1016/j.bmcl.2005.03.098

Reference yield: 94.0%

(E)-(4R,5R-4-methyl-3-isopropyl-5-phenyl-1,3,2-oxaazaborolidyl)(4-methoxyphenyl)ethene → (E)-2-(4-methoxyphenyl)vinylboronic acid (72316-18-8)

Guidance literature:

With NaOH; In water; the compd. was mixed with H2O and NaOH, heated to 100°C for 10 min, cooled, acidified with aq. HCl; filtered, recrystd. from boiling water, dried in vac.; elem. anal.;

DOI:10.1021/ja00082a006

Reference yield: 92.0%

2-[(E)-2-(4-methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (149777-83-3) → (E)-2-(4-methoxyphenyl)vinylboronic acid (72316-18-8)

Guidance literature:

With sodium periodate; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/S0040-4039(03)01140-7

upstream raw materials:

2-[(E)-2-(4-methoxyphenyl)ethenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

4-methoxyphenylacetylen

4-Methoxystyrene

(benzo-1,3,2-dioxoborolidyl)-(E)-2-(4-methoxyphenyl)ethene

Downstream raw materials:

5-[(E)-2-(4-Methoxy-phenyl)-vinyl]-pyrimidine-4,6-diamine

(E,E)-3-(4-chlorophenyl)-1-furan-2-yl-5-(4-methoxyphenyl)penta-2,4-dien-1-one

1-benzyl-4-(2-(4-methoxyphenyl)ethylidene)piperidine

1-(2-cyclohexylideneethyl)-4-methoxybenzene