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

Base Information

• Chemical Name: tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate
• CAS No.: 330793-01-6
• Molecular Formula: C17H26 B N O4
• Molecular Weight: 319.209
• Hs Code.: 2934999090
• European Community (EC) Number: 671-693-0
• DSSTox Substance ID: DTXSID60370397
• Wikidata: Q72448339
• Mol file: 330793-01-6.mol

Synonyms:330793-01-6;4-(N-Boc-amino)phenylboronic acid pinacol ester;tert-Butyl (4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate;tert-Butyl N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;4-boc-aminophenylboronic acid, pinacol ester;4-(boc-amino)benzeneboronic acid pinacol ester;4-(Boc-amino)phenylboronic acid pinacol ester;MFCD02179439;tert-butyl N-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;tert-Butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate;4-BOC-aminophenylboronic acid pinacol ester;4-(tert-butoxycarbonylamino)phenylboronic acid pinacol ester;tert-butyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate;tert-Butyl-N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-carbamate;SCHEMBL1255934;DTXSID60370397;4-(tert-butoxycarbonyl)aminophenylboronic acid, pinacol ester;AKOS015949229;AB11134;AM86864;AS-2611;CS-W000913;SY012199;A5908;B5588;FT-0616701;(4-boc-aminophenyl)boronic acid pinacol ester;EN300-312231;W10905;J-019008;J-513862;4-(Boc-amino)benzeneboronic acid pinacol cyclic ester;4-(N-Boc-amino)phenylboronic acid pinacol ester, 97%;Z1508685612;4-(tert-Butoxycarbonyl)aminophenylboronic acid pinacol ester;4-[(tert-Butoxycarbonyl)amino]phenylboronic Acid Pinacol Ester;N-Boc-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;(4-((TERT-BUTOXYCARBONYL)AMINO)PHENYL)BORONIC ACID PINACOL ESTER;4-[(TERT-BUTOXYCARBONYLAMINO)PHENYL]BORONIC ACID PINACOL ESTER;t-butyl(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)carbamate;tert-butyl[4(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]carbamate;N-(tert-Butoxycarbonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;t-butyl [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamate;t-butyl[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-carbamate;tert-butyl-n-[4-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)phenyl]carbamate;4-(N-Boc-amino)phenylboronicacidpinacolester

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

Chemical Property:

• Appearance/Colour: White crystalline powder
• Vapor Pressure: 2.57E-07mmHg at 25°C
• Melting Point: 167-170 ºC
• Boiling Point: 421.6°C at 760 mmHg
• PKA: 14.00±0.70(Predicted)
• Flash Point: 208.8°C
• PSA: 56.79000
• Density: 1.06g/cm³
• LogP: 3.40580
• Storage Temp.: Refrigerator (+4°C)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 319.1954885
• Heavy Atom Count: 23
• Complexity: 420

Purity/Quality:

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

4-Boc-aminophenylboronicAcidPinacolEster ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22-43
• Safety Statements: 37/39-26-36-36/37

MSDS Files:

SDS file from LookChem

Useful:

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

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

There total 15 articles about tert-Butyl (4-(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: 99.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + [4-(tert-butoxycarbonylamino)phenyl]boronic acid (380430-49-9) → (4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester (330793-01-6)

Guidance literature:

With 1H-imidazole; iron(III) chloride; In water; acetonitrile; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0033-1340500

Reference yield: 88.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline (214360-73-3) → (4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester (330793-01-6)

Guidance literature:

In toluene; at 90 ℃; for 18h; Inert atmosphere;

DOI:10.1002/anie.201907668

Reference yield: 88.0%

N-Boc-4-iodoaniline (159217-89-7) + bis(pinacol)diborane (73183-34-3) → (4-tert-butoxycarbonylaminophenyl)boronic acid pinacol ester (330793-01-6)

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

upstream raw materials:

bis(pinacol)diborane

tert-butyl (4-bromophenyl)carbamate

N-Boc-4-iodoaniline

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

Downstream raw materials:

methyl 4-(4-tert-butoxycarbonylamino-phenyl)-1-methyl-imidazole-2-carboxylate

t-butyl-4-(4-cyanothiophen-3-yl)phenylcarbamate

di(tert-butyl) 4',4''-(diazene-1,2-diyl)bis(biphenyl-4,4'-diyl)dicarbamate

5-(N-(tert-butoxycarbonyl)-4-anilino)-15-(2-pyridyl)ethynyl-10,20-bis[3,4,5-tris(9-methoxy-1,4,7-trioxanonyl)phenyl]porphyrinatozinc

Refernces

• 1、 Strauss, Michael J.,Jia, Manping,Evans, Austin M.,Castano, Ioannina,Li, Rebecca L.,Aguilar-Enriquez, Xavier,Roesner, Emily K.,Swartz, Jeremy L.,Chavez, Anton D.,Enciso, Alan E.,Stoddart, J. Fraser,Rolandi, Marco,Dichtel, William R.. "Diverse Proton-Conducting Nanotubes via a Tandem Macrocyclization and Assembly Strategy". supporting information. p. 8145 - 8153. Retrieved 2021/06/21.
• 2、 K?nig, Burkhard,Wang, Hua,Wang, Shun. "Photo-induced thiolate catalytic activation of inert Caryl-hetero bonds for radical borylation". supporting information. p. 1653 - 1665. Retrieved 2021/06/17.