tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Base Information

• Chemical Name: tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate
• CAS No.: 159624-15-4
• Molecular Formula: C17H26BNO4
• Molecular Weight: 319.209
• Hs Code.: 2934999090
• European Community (EC) Number: 671-698-8
• DSSTox Substance ID: DTXSID20378293
• Nikkaji Number: J1.486.113K
• Wikidata: Q72448344
• Mol file: 159624-15-4.mol

Synonyms:159624-15-4;tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate;2-(Boc-amino)phenylboronic Acid Pinacol Ester;Tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;2-boc-aminophenylboronic acid, pinacol ester;2-(boc-amino)benzeneboronic acid pinacol ester;(2-boc-aminophenyl)boronic acid, pinacol ester;2-(N-Boc-amino)phenylboronic acid pinacol ester;tert-Butyl-N-[2-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;MFCD03411943;tert-Butyl-N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-carbamate;tert-butyl [2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate;SCHEMBL14560;DTXSID20378293;2-(tert-Butoxycarbonylamino)phenylboronic acid pinacol ester;STR09002;(2-((TERT-BUTOXYCARBONYL)AMINO)PHENYL)BORONIC ACID PINACOL ESTER;AKOS015960066;AB14302;SY023463;2-(Boc-amino)phenylboronicAcidPinacolEster;2-BOC-aminophenylboronic acid pinacol ester;CS-0112317;FT-0643550;O10021;J-009620;2-(N-Boc-amino)phenylboronic acid pinacol ester, 97%;[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamic acid tert-butyl ester;2-[2-(tert-Butoxycarbonylamino)phenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane;tert-butyl 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-phenylcarbamate;Carbamic acid, N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-, 1,1-dimethylethyl ester;Carbamic acid,N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-,1,1-dimethylethylester

Chemical Property of tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

Chemical Property:

• Vapor Pressure: 4.4E-06mmHg at 25°C
• Melting Point: 96-100 °C(lit.)
• Refractive Index: 1.504
• Boiling Point: 383.423 °C at 760 mmHg
• PKA: 14.00±0.70(Predicted)
• Flash Point: 185.688 °C
• PSA: 56.79000
• Density: 1.073 g/cm³
• LogP: 3.40580
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 319.1954885
• Heavy Atom Count: 23
• Complexity: 428

Purity/Quality:

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

2-Boc-aminophenylboronicAcidPinacolEster ^*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=C2NC(=O)OC(C)(C)C

Technology Process of tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate

There total 6 articles about tert-Butyl (2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate 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: 68.0%

tert-butyl phenylcarbamate (3422-01-3) + bis(pinacol)diborane (73183-34-3) → tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (159624-15-4)

Guidance literature:

bis(pinacol)diborane; With 5-methyl-2-(thiophen-3-yl)pyridine; (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; In tetrahydrofuran; at 20 ℃; for 0.0333333h; Inert atmosphere; Glovebox;

tert-butyl phenylcarbamate; In tetrahydrofuran; at 100 ℃; for 12h; regioselective reaction; Inert atmosphere; Sealed tube;

DOI:10.1021/jacs.0c13415

Reference yield: 57.0%

tert-butyl 2-iodophenylcarbamate (161117-84-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → tert-butyl phenylcarbamate (3422-01-3) + tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (159624-15-4)

Guidance literature:

With triethylamine; CyJohnPhos; palladium diacetate; at 80 ℃; for 1h;

DOI:10.1021/jo005663d

Reference yield: 47.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 2-bromo-N-(tert-butoxycarbonyl)aniline (78839-75-5) → tert-butyl N-[2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate (159624-15-4)

Guidance literature:

2-bromo-N-(tert-butoxycarbonyl)aniline; With methyllithium; In diethyl ether; at 20 ℃; Inert atmosphere;

With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1h; Inert atmosphere;

2,3-dimethyl-2,3-butane diol; Further stages;

DOI:10.1021/ol9020755

upstream raw materials:

2-bromo-N-(tert-butoxycarbonyl)aniline

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

tert-butyl 2-iodophenylcarbamate

2,3-dimethyl-2,3-butane diol

Downstream raw materials:

2-methoxy-2'-N-tert-butoxycarbonylamino-6-p-tolylsulfinyl biphenyl

{2-[1-(tert-butyl-dimethyl-silanyloxymethyl)vinyl]phenyl}carbamic acid tert-butyl ester

ethyl 3-(1-(2-tert-butoxycarbonylamino)phenyl)-(3-formyl-5,6,7,8-tetrahydroindolizin-8-yl)propanoate

Refernces

• 1、 Reddy, Venkata Jaganmohan,Douglas, Christopher J.. "Highly enantioselective intramolecular cyanoamidation: (+)-horsfiline, (-)-coerulescine, and (-)-esermethole". supporting information; experimental part. p. 952 - 955. Retrieved 2010/06/15.
• 2、 Colobert, Francoise,Valdivia, Victoria,Choppin, Sabine,Leroux, Frederic R.,Fernandez, Inmaculada,Alvarez, Eleuterio,Khiar, Noureddine. "Axial chirality control during suzuki-miyaura cross-coupling reactions: The tert-Butylsulfinyl group as an efficient chiral auxiliary". supporting information; experimental part. p. 5130 - 5133. Retrieved 2009/12/28.