4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate
• CAS No.: 480424-70-2
• Molecular Formula: C14H19BO4
• Molecular Weight: 262.113
• Hs Code.: 29189900
• European Community (EC) Number: 808-214-3
• DSSTox Substance ID: DTXSID80378830
• Nikkaji Number: J1.982.317B
• Wikidata: Q72434390
• Mol file: 480424-70-2.mol

Synonyms:480424-70-2;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate;4-Acetoxyphenylboronic acid pinacol ester;[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl] Acetate;4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate;4-Acetoxyphenylboronic acid, pinacol ester;4-Acetoxybenzeneboronic acid pinacol ester;MFCD03453060;2-(4-Acetoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;(4-ACETOXYPHENYL)BORONIC ACID PINACOL ESTER;SCHEMBL311872;DTXSID80378830;KHBAJCWEQNVCSN-UHFFFAOYSA-N;AKOS015894332;AB15490;AS-2793;CS-W000940;AC-33904;SY057168;FT-0644725;T3224;4-Acetoxyphenylboronic acid pinacol ester, 97%;4-(4,4,5,5-tetramethyl-1,3-dioxaborolan-2-yl)phenyl acetate;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylacetate

Chemical Property of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate

Chemical Property:

• Melting Point: 67-71 °C(lit.)
• Refractive Index: 1.498
• Boiling Point: 351.9 °Cat760mmHg
• Flash Point: 166.6 °C
• PSA: 44.76000
• Density: 1.08 g/cm³
• LogP: 1.91110
• Storage Temp.: Inert atmosphere,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

4-Acetoxyphenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate

There total 6 articles about 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate 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: 84.4%

4-methylsulfanyl(methylcarbonyloxy)benzene (50910-13-9) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate (480424-70-2)

Guidance literature:

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

4-methylsulfanyl(methylcarbonyloxy)benzene; In hexane; at 80 ℃; for 12h; Glovebox; Inert atmosphere;

DOI:10.1021/acs.orglett.6b01250

Reference yield: 77.0%

4-acetoxyiodobenzene (33527-94-5) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate (480424-70-2)

Guidance literature:

With pyridine; C₅₀H₄₄CuN₄OP₂⁽¹⁺⁾*F₆P^(1-); N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 20 ℃; for 12h; Inert atmosphere; Irradiation;

DOI:10.1002/chem.201806345

Reference yield: 61.0%

4-acetyloxy-benzoic acid (2345-34-8) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl acetate (480424-70-2)

Guidance literature:

With palladium diacetate; 2,2-dimethylpropanoic anhydride; triethylamine; 1,4-di(diphenylphosphino)-butane; In 1,4-dioxane; at 160 ℃; for 15h;

DOI:10.1002/anie.201810145

upstream raw materials:

Phenyl acetate

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

4-methylsulfanyl(methylcarbonyloxy)benzene

bis(pinacol)diborane

Downstream raw materials:

methyl 4-acetoxybenzoate

N-(3-((4-cyanobenzyl)(4-(4'-hydroxybiphenyl-3-yloxy)benzyl)amino)-2-methylphenyl)methanesulfonamide

Refernces

• 1、 Wu, Jie,Wang, Zengwei,Chen, Xiao-Yue,Wu, Yichen,Wang, Daoming,Peng, Qian,Wang, Peng. "Para-selective borylation of monosubstituted benzenes using a transient mediator". . p. 336 - 340. Retrieved 2019/12/09.
• 2、 Nitelet, Antoine,Thevenet, Damien,Schiavi, Bruno,Hardouin, Christophe,Fournier, Jean,Tamion, Rodolphe,Pannecoucke, Xavier,Jubault, Philippe,Poisson, Thomas. "Copper-Photocatalyzed Borylation of Organic Halides under Batch and Continuous-Flow Conditions". supporting information. p. 3262 - 3266. Retrieved 2019/02/13.