Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Base Information

• Chemical Name: Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate
• CAS No.: 171364-80-0
• Molecular Formula: C14H19BO4
• Molecular Weight: 262.113
• Hs Code.: 29310099
• European Community (EC) Number: 640-877-2
• DSSTox Substance ID: DTXSID10378500
• Nikkaji Number: J845.354C
• Wikidata: Q72491114
• Mol file: 171364-80-0.mol

Synonyms:171364-80-0;Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;4-Methoxycarbonylphenylboronic acid pinacol ester;17136-80-0;4-Methoxycarbonylphenylboronic acid, pinacol ester;MFCD02179438;Methyl4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;4-(methoxycarbonyl)benzeneboronic acid pinacol ester;methyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;methyl4-(4,4,5,5-tetramethyl-1,3,2- dioxaborolan-2-yl)benzoate;4-(methoxycarbonyl)phenylboronic acid pinacol ester;4-Carbomethoxyphenylboronic acid pinacol ester;SCHEMBL105161;DTXSID10378500;(4-(METHOXYCARBONYL)PHENYL)BORONIC ACID PINACOL ESTER;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester;AKOS000283812;AB11131;AM62748;AS-2266;CS-W000882;SY003286;FT-0643640;M3057;10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N;EN300-336124;10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N.1;4-Methoxycarbonylbenzeneboronic acid pinacol ester;A811322;doi:10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N;(4-methoxycarbonylphenyl)boronic acid, pinacol ester;doi:10.14272/REIZEQZILPXYKS-UHFFFAOYSA-N.1;J-010720;J-522081;J-522239;4-Methoxycarbonylphenylboronic acid pinacol ester, 97%;Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 -yl)benzoate;methyl?4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;2-(4-Methoxycarbonylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;2-[4-(Methoxycarbonyl)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;4-(4,4,5,5-tetramethyl-[1,3,2]dioxa borolan-2-yl)-benzoic acid methyl ester;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)BENZOIC ACID METHYL ESTER;Benzoic acid, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-, methyl ester;Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) benzoate (4-Methoxycarbonylphenylboronic acid pinacol ester)

Chemical Property of Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

Chemical Property:

• Vapor Pressure: 4.88E-07mmHg at 25°C
• Melting Point: 77-81 °C(lit.)
• Refractive Index: 1.507
• Boiling Point: 355.6 °C at 760 mmHg
• Flash Point: 168.8 °C
• PSA: 44.76000
• Density: 1.08 g/cm³
• LogP: 1.77240
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 262.1376392
• Heavy Atom Count: 19
• Complexity: 329

Purity/Quality:

98% ^*data from raw suppliers

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

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)C(=O)OC
• Uses: Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate was used to prepare 2-aryl-4,4,5,5,-tetramethyl-1,3,2-dioxaborolanes via palladium-catalyzed coupling reactions.

Technology Process of Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

There total 59 articles about Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate 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%

Methyl 4-chlorobenzoate (1126-46-1) + bis(pinacol)diborane (73183-34-3) → methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (171364-80-0)

Guidance literature:

With tris(trimethylphosphine)nickel(II) chloride; (2,2,2-trifluoroethoxy)trimethylsilane; cesium fluoride; In tetrahydrofuran; at 100 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol202267t

Reference yield: 96.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 4-methoxycarbonylphenylboronic acid (99768-12-4) → methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (171364-80-0)

Guidance literature:

In tetrahydrofuran; for 6h; Reflux; Inert atmosphere;

DOI:10.1039/d0ra08603g

Reference yield: 94.7%

methyl 4-(methylthio)benzoate (3795-79-7) + bis(pinacol)diborane (73183-34-3) → methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (171364-80-0)

Guidance literature:

bis(pinacol)diborane; With [Rh(OH)(cod)]2; tricyclohexylphosphine; In hexane; at 80 ℃; for 1h; Glovebox; Inert atmosphere;

methyl 4-(methylthio)benzoate; In hexane; at 80 ℃; for 12h; Glovebox; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01250

upstream raw materials:

Phenyl triflate

4-carbomethoxyphenyl triflate

bis(pinacol)diborane

Methyl 4-chlorobenzoate

Downstream raw materials:

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzohydrazide

methyl 2',5'-bis[(E)-1,2-difluoro-2-(4-octyloxyphenyl)vinyl]-4'-methoxybiphenyl-4-carboxylate

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid tert-butyl ester

4'''''-bromo-2',2''''',4,5',5'''''-tetramethoxy-4-methoxycarbonyl(hexa-p-phenylene)

Refernces

• 1、 Zhang, Jie,Wang, Xiaolong,Yu, Haitao,Ye, Jiahai. "Sandmeyer-type reaction to pinacol arylboronates in water phase: A green borylation process". . p. 1394 - 1396. Retrieved 2012.
• 2、 Yang, Shuai-Qi,Qu, Wei,Pan, Hong-Bing,Zhang, Yu-Dong,Zheng, Shi-Jun,Fan, Xing-He,Shen, Zhihao. "Effects of main chain and acceptor content on phase behaviors of hydrogen-bonded main-chain/side-chain combined liquid crystalline polymers". . p. 355 - 364. Retrieved 2016.
• 3、 Lamola, Jairus L.,Moshapo, Paseka T.,Holzapfel, Cedric W.,Christopher Maumela, Munaka. "Palladium-catalyzed borylation of aryl bromides and chlorides using phosphatrioxa-adamantane ligands". supporting information. . Retrieved 2021/12/13.
• 4、 Kleman, Adam F.,Dufek, Deseree L.,Fobe, Theodore L.,McCaslin, Darrell R.,Cary, Brian P.,Shirts, Michael R.,Gellman, Samuel H.. "Potential Foldamers Based on an ortho-Terphenyl Amino Acid". supporting information. p. 4855 - 4859. Retrieved 2021/06/28.