3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester

Base Information

• Chemical Name: 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester
• CAS No.: 944392-68-1
• Molecular Formula: C16H21BO6
• Molecular Weight: 320.15
• Mol file: 944392-68-1.mol

Synonyms:dimethyl isophthalate-5-pinacolboronate;QC-9864;3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester;dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-benzenedicarboxylate;C-2333;benzene-1,3,5-tris(3',5'-benzenedicarboxylic acid dimethyl ester);3,5-DIMETHYL(BENZENECARBOXYLATE)-5-BORONIC ACID PINACOL ESTER;dimethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolyl)isophthalate;Dimethyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-isophthalate;查看更多英文别名收起

Chemical Property of 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester

Chemical Property:

• Melting Point: 128℃
• Boiling Point: 435.4±35.0 °C(Predicted)
• PSA: 71.06000
• Density: 1.16±0.1 g/cm3(Predicted)
• LogP: 1.55900
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature

Purity/Quality:

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

Dimethyl 5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isophthalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester

There total 12 articles about 3,5-Bis(methoxycarbonyl)phenylboronic acid pinacol ester 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%

dimethyl Isophthalate (1459-93-4) + bis(pinacol)diborane (73183-34-3) → dimethyl 5-(pinacolboryl)isophthalate (944392-68-1)

Guidance literature:

With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1-(4,4'-di-tert-butyl-[2,2'-bipyridin]-6-yl)-2-(dimethyl(phenyl)silyl)-2,3-dihydro-1H-benzo[d][1,3,2]diazaborole; Inert atmosphere; Schlenk technique; Sealed tube;

DOI:10.3390/molecules24071434

Reference yield: 92.0%

dimethyl 5-bromoisophthalate (51760-21-5) + bis(pinacol)diborane (73183-34-3) → dimethyl 5-(pinacolboryl)isophthalate (944392-68-1)

Guidance literature:

With Pd(dppf)Cl₂; potassium acetate; In 1,4-dioxane; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1039/c5cc01055a

Reference yield: 86.0%

1,3-dimethyl 5-chlorobenzene-1,3-dicarboxylate (20330-90-9) + bis(pinacol)diborane (73183-34-3) → dimethyl 5-(pinacolboryl)isophthalate (944392-68-1)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; rac-3-(tert-butyl)-4-(2,6-dimethoxyphenyl)-2,3-dihydrobenzo[d][1,3]oxaphosphole; potassium acetate; In N,N-dimethyl acetamide; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol2000556

upstream raw materials:

5-iodo-isophthalic acid dimethyl ester

bis(pinacol)diborane

dimethyl 5-aminoisophthalate

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

Downstream raw materials:

biphenyl-3,4',5-tricarboxylic acid

tetramethyl 5,5'-(9H-fluorene-2,7-diyl)diisophthalate

C₁₆H₁₈F₃NO₈S

1,3-dimethyl 5-ethynylisophthalate

Refernces

• 1、 Slack, Eric D.,Colacot, Thomas J.. "Understanding the Activation of Air-Stable Ir(COD)(Phen)Cl Precatalyst for C-H Borylation of Aromatics and Heteroaromatics". supporting information. p. 1561 - 1565. Retrieved 2021/02/20.
• 2、 Gao, Pengcheng,Szostak, Michal. "Highly Selective and Divergent Acyl and Aryl Cross-Couplings of Amides via Ir-Catalyzed C-H Borylation/N-C(O) Activation". supporting information. p. 6010 - 6015. Retrieved 2020/07/30.