2-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester

Base Information

• Chemical Name: 2-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester
• CAS No.: 956229-69-9
• Molecular Formula: C₁₇H₂₅BO₄
• Molecular Weight: 304.194
• Hs Code.: 2934999090
• European Community (EC) Number: 800-444-2
• DSSTox Substance ID: DTXSID60402581
• Nikkaji Number: J3.141.592F
• Wikidata: Q82206006
• Mol file: 956229-69-9.mol

Synonyms:956229-69-9;2-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester;Tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;2-TERT-BUTOXYCARBONYLPHENYLBORONIC ACID PINACOL ESTER;SCHEMBL6240652;2-(tert-Butoxycarbonyl)phenylboronic acid, pinacol ester;DTXSID60402581;LPIQEOUMTWQOOM-UHFFFAOYSA-N;MFCD03453053;AKOS015893177;AB15482;BS-29887;CS-0175395;N12120;2-t-butoxycarbonylphenylboronic acid pinacol ester;2-t-butoxycarbonylphenyl-boronic acid pinacol ester;2-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester, AldrichCPR;Tert-butyl2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate;2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolane-2-yl)benzoic acid tert-butyl ester

Chemical Property of 2-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester

Chemical Property:

• Vapor Pressure: 1.74E-06mmHg at 25°C
• Melting Point: 65-67 °C
• Boiling Point: 396.2°C at 760 mmHg
• Flash Point: 193.4°C
• PSA: 44.76000
• Density: 1.04g/cm³
• LogP: 2.94110
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 304.1845894
• Heavy Atom Count: 22
• Complexity: 409

Purity/Quality:

98%min ^*data from raw suppliers

2-(tert-Butoxycarbonyl)benzeneboronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=CC=C2C(=O)OC(C)(C)C

Technology Process of 2-(tert-Butoxycarbonyl)phenylboronic acid pinacol ester

There total 3 articles about 2-(tert-Butoxycarbonyl)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: 87.0%

benzoic acid tert-butyl ester (774-65-2) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid tert-butyl ester (956229-69-9)

Guidance literature:

With silica-SMAP-Ir(OCH₃)(C₈H₁₂); In hexane; ligand reacted with B-compound in hexane in presence of Ir-complex as catalyst at 50°C for 1 h;

Reference yield: 84.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + tert-butyl 2-bromobenzoate (55666-42-7) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid tert-butyl ester (956229-69-9)

Guidance literature:

tert-butyl 2-bromobenzoate; With sec.-butyllithium; In tetrahydrofuran; hexane; cyclohexane; at -48 ℃; for 1.52778E-05h;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; hexane; cyclohexane; at -48 ℃; for 0.0025h;

DOI:10.1039/c2cc36197c

Reference yield: 71.0%

tert-butyl 2-methoxybenzoate (16537-20-5) + bis(pinacol)diborane (73183-34-3) → 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid tert-butyl ester (956229-69-9)

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium formate; tricyclohexylphosphine; In toluene; at 95 ℃; for 15h; Inert atmosphere;

DOI:10.1021/jacs.5b03955

upstream raw materials:

benzoic acid tert-butyl ester

bis(pinacol)diborane

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

tert-butyl 2-bromobenzoate

Refernces

• 1、 Wang, Guanghui,Liu, Li,Wang, Hong,Ding, You-Song,Zhou, Jing,Mao, Shuai,Li, Pengfei. "N,B-bidentate boryl ligand-supported iridium catalyst for efficient functional-group-directed C-H borylation". supporting information. p. 91 - 94. Retrieved 2017/05/16.
• 2、 Ghaffari, Behnaz,Preshlock, Sean M.,Plattner, Donald L.,Staples, Richard J.,Maligres, Peter E.,Krska, Shane W.,Maleczka, Robert E.,Smith, Milton R.. "Silyl phosphorus and nitrogen donor chelates for homogeneous ortho borylation catalysis". supporting information. p. 14345 - 14348. Retrieved 2014/12/10.