(3-Boc-aminophenyl)boronic acid

Base Information

• Chemical Name: (3-Boc-aminophenyl)boronic acid
• CAS No.: 380430-68-2
• Molecular Formula: C11H16BNO4
• Molecular Weight: 237.063
• Hs Code.: 2931900090
• European Community (EC) Number: 670-412-9
• DSSTox Substance ID: DTXSID00959004
• Nikkaji Number: J2.246.081A
• Wikidata: Q72448338
• Mol file: 380430-68-2.mol

Synonyms:380430-68-2;(3-BOC-AMINOPHENYL)BORONIC ACID;3-(N-Boc-amino)phenylboronic acid;3-BOC-aminophenylboronic acid;3-(tert-Butoxycarbonylamino)phenylboronic acid;[3-[(2-methylpropan-2-yl)oxycarbonylamino]phenyl]boronic Acid;(3-((tert-Butoxycarbonyl)amino)phenyl)boronic acid;MFCD03411945;3-(tert-Butoxycarbonylamino)phenyl-boronic acid;{3-[(tert-Butoxycarbonyl)amino]phenyl}boronic acid;(3-{[(tert-butoxy)carbonyl]amino}phenyl)boronic acid;N-Boc-3-aminophenylboronic Acid;3-[(tert-butoxycarbonyl)amino]phenylboronic acid;3-[(tert-Butoxycarbonyl)amino]benzeneboronic acid;SCHEMBL177465;3-(Boc-amino)phenylboronic Acid;DTXSID00959004;CWLNHPXWZRALFS-UHFFFAOYSA-N;BCP33013;AKOS015841458;AB14304;AS-2309;CS-W000924;3-(BOC-AMINO)BENZENEBORONIC ACID;PD194973;SY031626;3-(N-Boc-amino)phenylboronic acid, >=95%;B4279;FT-0644550;(3-tert-Butoxycarbonylaminophenyl)-boronic acid;EN300-316758;[3-(tert-butoxycarbonylamino)phenyl]boronic acid;J-510914;(3-{[tert-Butoxy(hydroxy)methylidene]amino}phenyl)boronic acid;[3-({[(1,1-dimethylethyl)oxy]carbonyl}amino)phenyl]boronic acid

Chemical Property of (3-Boc-aminophenyl)boronic acid

Chemical Property:

• Melting Point: 160-170°C
• Refractive Index: 1.53
• PKA: 8.23±0.10(Predicted)
• PSA: 78.79000
• Density: 1.18g/cm³
• LogP: 0.78640
• Storage Temp.: Keep Cold
• Solubility.: soluble in Methanol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 237.1172382
• Heavy Atom Count: 17
• Complexity: 265

Purity/Quality:

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

3-Boc-aminophenylboronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B(C1=CC(=CC=C1)NC(=O)OC(C)(C)C)(O)O
• Uses: Reactant for:Rhodium-catalyzed cross-couplingPd-catalyzed Suzuki-Miyaura coupling

Technology Process of (3-Boc-aminophenyl)boronic acid

There total 5 articles about (3-Boc-aminophenyl)boronic acid 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: 97.0%

tert-butyl N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]carbamate (330793-09-4) + dihydroxy-methyl-borane (13061-96-6) → 3-(tert-butoxycarbonylamino)phenylboronic acid (380430-68-2)

Guidance literature:

With sodium hydroxide; In acetone; at 20 ℃;

DOI:10.1021/acs.orglett.9b00584

Reference yield: 77.0%

{3-[5-(4-methoxyphenyl)-4,4-dimethyl-[1,3,2]dioxaborolan-2-yl]-phenyl}carbamic acid tert-butyl ester → 3-(tert-butoxycarbonylamino)phenylboronic acid (380430-68-2)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 24h;

DOI:10.1016/j.tetlet.2005.10.010

Reference yield: 62.0%

tetrahydroxydiboron (13675-18-8) + iodo-3-(tert-butyloxycarbonylamino)benzene (143390-49-2) → 3-(tert-butoxycarbonylamino)phenylboronic acid (380430-68-2)

Guidance literature:

With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); tetramethyl ammonium acetate; In 2-methyltetrahydrofuran; methanol; water; at 40 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1021/acs.joc.0c00929

upstream raw materials:

di-tert-butyl dicarbonate

3-Aminophenylboronic acid

tert-butyl N-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)phenyl]carbamate

dihydroxy-methyl-borane

Downstream raw materials:

tert-butyl (3-(2-fluoro-2-(2-(quinolin-8-ylcarbamoyl)phenyl)ethyl)phenyl)carbamate

tert-butyl 3-allylphenylcarbamate

tert-butyl 3-(4-amino-1-methyl-1H-pyrazol-5-yl)phenylcarbamate

{3-[6-(1-methylpiperidin-4-ylamino)imidazo[1,2-b]pyridazin-3-yl]phenyl}carbamic acid tert-butyl ester

Refernces

• 1、 -. "MITOGEN-ACTIVATED PROTEIN KINASE KINASE 7 INHIBITORS". Page/Page column 36-37. . Retrieved 2019/12/28.
• 2、 Juchum, Michael,Günther, Marcel,D?ring, Eva,Sievers-Engler, Adrian,L?mmerhofer, Michael,Laufer, Stefan. "Trisubstituted Imidazoles with a Rigidized Hinge Binding Motif Act As Single Digit nM Inhibitors of Clinically Relevant EGFR L858R/T790M and L858R/T790M/C797S Mutants: An Example of Target Hopping". supporting information. p. 4636 - 4656. Retrieved 2017/06/13.