1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

Base Information

• Chemical Name: 1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine
• CAS No.: 747413-21-4
• Molecular Formula: C17H27BN2O2
• Molecular Weight: 302.225
• Hs Code.: 2933599090
• European Community (EC) Number: 640-473-6
• DSSTox Substance ID: DTXSID40592131
• Wikidata: Q72495613
• Mol file: 747413-21-4.mol

Synonyms:747413-21-4;1-Methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine;1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine;4-(4-Methylpiperazin-1-yl)phenylboronic acid, pinacol ester;4-(4-Methylpiperazin-1-yl)phenylboronic Acid Pinacol Ester;4-(4-METHYL-1-PIPERAZINYL)PHENYLBORONIC ACID PINACOL ESTER;MFCD06795650;4-(4-METHYL-1-PIPERAZINYL)BENZENEBORONIC ACID PINACOL ESTER;4-(4-Methylpiperazin-1-yl)phenylboronic acid, pinacol ester, AldrichCPR;1-methyl-4-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine;SCHEMBL19583;4-(4-Methyl-1-piperazinyl)phenylboronicAcidPinacolEster;DTXSID40592131;RDFJBDMCBVSCFI-UHFFFAOYSA-N;(4-(4-METHYLPIPERAZIN-1-YL)PHENYL)BORONIC ACID PINACOL ESTER;RB2063;AKOS015903909;AB29168;AC-7064;AM85290;AS-2372;CS-W012121;SY003842;A22640;EN300-7390362;J-513553;Z2044826970;4-(4-Methylpiperazin-1-yl)phenylboronic acid,pinacol ester;4-(4-methylpiperazin-1-yl) phenylboronic acid pinacol ester;1-METHYL-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]PIPERAZINE;1-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-piperazine;1-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]piperazine;1-METHYL-4-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL) PHENYL]PIPERAZINE;1-Methyl-4[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-phenyl]-piperazine;Piperazine, 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-

Chemical Property of 1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

Chemical Property:

• Vapor Pressure: 3.09E-07mmHg at 25°C
• Melting Point: 112-114°C
• Refractive Index: 1.542
• Boiling Point: 419.2 °C at 760 mmHg
• PKA: 7.78±0.42(Predicted)
• Flash Point: 207.3 °C
• PSA: 24.94000
• Density: 1.07 g/cm³
• LogP: 1.74050
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: Insoluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 302.2165583
• Heavy Atom Count: 22
• Complexity: 370

Purity/Quality:

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

1-Methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N3CCN(CC3)C
• Uses: 4-(4-Methyl-1-piperazinyl)benzeneboronic acid pinacol ester is used as pharmaceutical intermediate.

Technology Process of 1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine

There total 5 articles about 1-Methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine 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: 85.0%

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) + 1-bromo-4-(4-methyl-1-piperazinyl)benzene (130307-08-3) → 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (747413-21-4)

Guidance literature:

1-bromo-4-(4-methyl-1-piperazinyl)benzene; With tert.-butyl lithium; In tetrahydrofuran; n-heptane; at -78 ℃; for 1h; Inert atmosphere;

2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane; In tetrahydrofuran; n-heptane; at 20 ℃; for 6h;

Reference yield: 67.0%

bis(pinacol)diborane (73183-34-3) + 1-bromo-4-(4-methyl-1-piperazinyl)benzene (130307-08-3) → 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (747413-21-4)

Guidance literature:

With potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Inert atmosphere; Reflux;

Reference yield: 45.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + 1-bromo-4-(4-methyl-1-piperazinyl)benzene (130307-08-3) → 1-methyl-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine (747413-21-4)

Guidance literature:

1-bromo-4-(4-methyl-1-piperazinyl)benzene; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

2,3-dimethyl-2,3-butane diol; With Triisopropyl borate; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2012.11.001

upstream raw materials:

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

1-bromo-4-(4-methyl-1-piperazinyl)benzene

4-bromo-aniline

bis(pinacol)diborane

Downstream raw materials:

(1R,2S)-5'-methoxy-1'-methyl-2-(3-(4-(4-methylpiperazin-1-yl)phenyl)-1H-indazol-6-yl)spiro[cyclopropan-1,3'-indolin]-2'-one 2,2,2-trifluoroacetate

(1R,2R)-methyl 1-((S)-2-(tert-butoxycarbonylamino)butanamido)-2-(4'-(4-methylpiperazin-1-yl)biphenyl-4-yl)cyclopropanecarboxylate

(1S,2S)-methyl 1-((S)-2-(tert-butoxycarbonylamino)butanamido)-2-(4'-(4-methylpiperazin-1-yl)biphenyl-4-yl)cyclopropanecarboxylate

tert-butyl (S)-1-((1R,2R)-1-carbamoyl-2-(4'(4-methylpiperazine-1-yl)biphenyl-4-yl)cyclopropylamino)-1-oxobutan-2-ylcarbamate

Refernces

• 1、 Andersen, Valdemar L.,Herth, Matthias M.,Lehel, Szabolcs,Knudsen, Gitte M.,Kristensen, Jesper L.. "Palladium-mediated conversion of para-aminoarylboronic esters into para-aminoaryl-11C-methanes". supporting information. p. 213 - 216. Retrieved 2013/02/22.
• 2、 -. "QUINOXALINE DERIVATIVES AS INHIBITORS OF THE TYROSINE KINASE ACTIVITY OF JANUS KINASES". Page/Page column 49-50. . Retrieved 2009/01/24.