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

Base Information

• Chemical Name: 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine
• CAS No.: 852227-90-8
• Molecular Formula: C16H24BNO2
• Molecular Weight: 273.183
• Hs Code.: 2934999090
• European Community (EC) Number: 640-330-8
• DSSTox Substance ID: DTXSID80594477
• Nikkaji Number: J3.611.165H
• Wikidata: Q72505283
• Mol file: 852227-90-8.mol

Synonyms:852227-90-8;1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine;1-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)PHENYL]PYRROLIDINE;4-Pyrrolidinophenylboronic acid, pinacol ester;4-(1-Pyrrolidinyl)benzeneboronic acid pinacol ester;4-Pyrrolidinophenylboronic acid pinacol ester;4-(Pyrrolidin-1-yl)benzeneboronic acid, pinacol ester;SCHEMBL2354573;DTXSID80594477;DWJNNJSONWFVBT-UHFFFAOYSA-N;(4-(PYRROLIDIN-1-YL)PHENYL)BORONIC ACID PINACOL ESTER;1-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolidine;MFCD08060504;RB2064;AKOS015842226;AM85288;CS-W014023;SB22911;DS-13152;DB-076290;EN300-1674304;A863644;J-504106;Z1741976085;Pyrrolidine, 1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-;1-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]pyrrolidine, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 1.77E-06mmHg at 25°C
• Melting Point: 109 °C
• Refractive Index: 1.531
• Boiling Point: 396 °C at 760 mmHg
• PKA: 5.14±0.40(Predicted)
• Flash Point: 193.3 °C
• PSA: 21.70000
• Density: 1.05 g/cm³
• LogP: 2.65100
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility.: Slightly soluble in water.
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 273.1900092
• Heavy Atom Count: 20
• Complexity: 328

Purity/Quality:

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

1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC=C(C=C2)N3CCCC3
• Uses: It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff.

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

There total 7 articles about 1-(4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidine 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: 92.0%

2,3-dimethyl-2,3-butane diol (76-09-5) + C16H16BNO2 → 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidineate (852227-90-8)

Guidance literature:

With triethylamine; In toluene; at 20 ℃; for 1h; Schlenk technique;

DOI:10.1002/anie.201611536

Reference yield: 86.0%

N-(4-fluorophenyl)tetrahydropyrrole (4280-34-6) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidineate (852227-90-8)

Guidance literature:

With 2-((2,4,6-trimethylphenyl)amino)-4-((2,4,6-trimethylphenyl)imino)-2-pentene; magnesium; cobalt(II) chloride; In tetrahydrofuran; at 60 ℃; for 48h; Inert atmosphere; Glovebox;

DOI:10.1021/acs.orglett.8b03167

Reference yield: 66.0%

1-(4-bromo-phenyl)-pyrrolidine (22090-26-2) + bis(pinacol)diborane (73183-34-3) → 1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidineate (852227-90-8)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; Reflux; Inert atmosphere;

DOI:10.1246/bcsj.20180151

upstream raw materials:

N-phenylpyrrolidine

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

1-(4-bromo-phenyl)-pyrrolidine

bis(pinacol)diborane

Downstream raw materials:

C₂₆H₂₅FN₄O₃

C₃₆H₄₇FN₄O₄Si

C₂₂H₂₈ClFN₄OSi

C₂₂H₂₈ClFN₄OSi

Refernces

• 1、 Asako, Sobi,Ilies, Laurean,Jin, Yushu,Ramadoss, Boobalan. "Remote steric control for undirected meta-selective C-H activation of arenes". . p. 658 - 663. Retrieved 2022/02/21.
• 2、 Yin, Qin,Klare, Hendrik F. T.,Oestreich, Martin. "Catalytic Friedel–Crafts C?H Borylation of Electron-Rich Arenes: Dramatic Rate Acceleration by Added Alkenes". . p. 3712 - 3717. Retrieved 2017/03/21.