TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID

Base Information

• Chemical Name: TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID
• CAS No.: 154230-29-2
• Molecular Formula: C8H8 B Cl O2
• Molecular Weight: 182.414
• Hs Code.: 29310099
• Mol file: 154230-29-2.mol

Synonyms:Boronicacid, [(1E)-2-(4-chlorophenyl)ethenyl]- (9CI); Boronic acid,[2-(4-chlorophenyl)ethenyl]-, (E)-; trans-2-(4-Chlorophenyl)ethenylboronic acid

Chemical Property of TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID

Chemical Property:

• Vapor Pressure: 1.04E-05mmHg at 25°C
• Melting Point: 165 °C (dec.)(lit.)
• Refractive Index: 1.6
• Boiling Point: 356.7°Cat760mmHg
• PKA: 9.55±0.43(Predicted)
• Flash Point: 169.6°C
• PSA: 40.46000
• Density: 1.277g/cm³
• LogP: 1.36520
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

trans-2-(4-Chlorophenyl)vinylboronic acid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Uses: Reactant involved in:? ;Synthesis of biarylketones and phthalides1? ;Trifluoromethylation2? ;Asymmetrical Michael addition for preparation of chromanes3? ;Cobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds4? ;1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydes5? ;Petasis reactions6 Reactant involved in:Synthesis of biarylketones and phthalidesTrifluoromethylationAsymmetrical Michael addition for preparation of chromanesCobalt-catalyzed coupling to vinyl nitrogen containing heteroaromatic compounds1,2 and 1,4-Addition reactions with o-hydroxycinnamaldehydesPetasis reactions

Technology Process of TRANS-2-(4-CHLOROPHENYL)VINYLBORONIC ACID

There total 5 articles about TRANS-2-(4-CHLOROPHENYL)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: 99.0%

4-n-chlorophenylacetylene (873-73-4) + benzo[1,3,2]dioxaborole (274-07-7) → (E)-4-chlorostyrylboronic acid (154230-29-2)

Guidance literature:

4-n-chlorophenylacetylene; benzo[1,3,2]dioxaborole; In tetrahydrofuran; for 18h; Reflux;

With water; at 20 ℃; for 4h;

Reference yield: 96.0%

(E)-(4R,5R-4-methyl-3-isopropyl-5-phenyl-1,3,2-oxaazaborolidyl)(4-chlorophenyl)ethene → (E)-4-chlorostyrylboronic acid (154230-29-2)

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:

4-n-chlorophenylacetylene (873-73-4) → (E)-4-chlorostyrylboronic acid (154230-29-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran / 70 °C

2: water

With water; In tetrahydrofuran;

DOI:10.1071/CH10341

upstream raw materials:

4-n-chlorophenylacetylene

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

benzo[1,3,2]dioxaborole

Downstream raw materials:

(1E,3E)-1,4-bis(p-chlorophenyl)-1,3-butadiene

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

(E)-4-chloro-4'-nitrostilbene

(2E)-1,3-bis(4-chlorophenyl)prop-2-en-1-ol

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