2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Base Information

• Chemical Name: 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline
• CAS No.: 819058-34-9
• Molecular Formula: C12H17BFNO2
• Molecular Weight: 237.082
• Hs Code.: 2931900090
• European Community (EC) Number: 690-889-7
• DSSTox Substance ID: DTXSID10591550
• Nikkaji Number: J2.303.813G
• Wikidata: Q72437286
• Mol file: 819058-34-9.mol

Synonyms:819058-34-9;4-Amino-3-fluorophenylboronic acid pinacol ester;2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;4-Amino-3-fluorophenylboronic acid, pinacol ester;MFCD09033884;2-fluoro-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)aniline;BENZENAMINE, 2-FLUORO-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-;SCHEMBL59080;(4-AMINO-3-FLUOROPHENYL)BORONIC ACID PINACOL ESTER;DTXSID10591550;AIXGNRNTXUKZLC-UHFFFAOYSA-N;AKOS015920193;CS-W008460;MB06838;DS-13208;SY011627;AM20041200;EN300-1723410;A864484;Z1741977421;4-Amino-3-fluorophenylboronic acid pinacol ester, AldrichCPR;2-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine;2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-aniline;2-fluoro-4-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)aniline

Chemical Property of 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Chemical Property:

• Vapor Pressure: 0.000136mmHg at 25°C
• Refractive Index: 1.504
• Boiling Point: 333.5 °C at 760 mmHg
• PKA: 2.84±0.10(Predicted)
• Flash Point: 155.5 °C
• PSA: 44.48000
• Density: 1.11 g/cm³
• LogP: 2.28830
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Sensitive.: Air Sensitive
• Solubility.: Chloroform (Sparingly), DMSO (Sparingly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 237.1336371
• Heavy Atom Count: 17
• Complexity: 282

Purity/Quality:

98% ^*data from raw suppliers

4-Amino-3-fluorophenylboronic acid pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC(=C(C=C2)N)F

Technology Process of 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

There total 13 articles about 2-Fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline 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: 90.6%

4-bromo-2-fluoroaniline (367-24-8) + bis(pinacol)diborane (73183-34-3) → 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (819058-34-9)

Guidance literature:

With potassium acetate; 1,1'-bis-(diphenylphosphino)ferrocene; In 1,4-dioxane; at 80 ℃;

Reference yield: 84.0%

2-(3-fluoro-4-nitrophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (939968-60-2) → 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (819058-34-9)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃; for 4h; under 760.051 Torr;

DOI:10.1021/jo402618r

Reference yield: 75.0%

2-fluro-4-iodoaniline (29632-74-4) + bis(pinacol)diborane (73183-34-3) → 2-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (819058-34-9)

Guidance literature:

With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In dimethyl sulfoxide; at 85 ℃; for 4.5h; Inert atmosphere;

upstream raw materials:

2-fluro-4-iodoaniline

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

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

bis(pinacol)diborane

Downstream raw materials:

4-(4-amino-3-fluorophenyl)-2-(2-difluoromethylbenzimidazol-1-yl)-6-morpholinopyrimidine

2,5-dichloro-N-[4-(6-chloro-5-formyl-pyrazin-2-yl)-2-fluoro-phenyl]benzenesulfonamide

potassium 8-(4-amino-3-fluorophenyl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylate

Refernces

• 1、 Montero Bastidas, Jose R.,Oleskey, Thomas J.,Miller, Susanne L.,Smith, Milton R.,Maleczka, Robert E.. "Para-Selective, Iridium-Catalyzed C-H Borylations of Sulfated Phenols, Benzyl Alcohols, and Anilines Directed by Ion-Pair Electrostatic Interactions". . p. 15483 - 15487. Retrieved 2019/10/11.
• 2、 -. "NOVEL COMPOUNDS AS REARRANGED DURING TRANSFECTION (RET) INHIBITORS". Page/Page column 68. . Retrieved 2016/04/20.