Tri-tert-butylphosphine tetrafluoroborate | Phosphoruses

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Quality Control of Tri-tert-butylphosphine tetrafluoroborate Purity: 98% SDS Specification

COA

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NMR

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CNMR

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Product Citations Show More

Anhydrous and Stereoretentive Fluoride-Enhanced Suzuki–Miyaura Coupling of Immunomodulatory Imide Drug Derivatives

William F. Tracy ; Geraint H. M. Davies ; Lauren N. Grant ; Jacob M. Ganley ; Jesus Moreno ; Emily C. Cherney , et al.

DOI: 10.1021/acs.joc.3c02873 JOC,2024,89(7):4595-4606.

Abstract: Immunomodulatory imide drugs form the core of many pharmaceutically relevant structures, but Csp2–Csp2 bond formation via metal-catalyzed cross coupling is difficult due to the sensitivity of the glutarimide ring ubiquitous in these structures. We report that replacement of the traditional alkali base with a fluoride source enhances a previously challenging Suzuki–Miyaura coupling on glutarimide-containing compounds with trifluoroborates. These enabling conditions are reactive enough to generate these derivatives in high yields but mild enough to preserve both the glutarimide and its sensitive stereocenter. Experimental and computational data suggest a mechanistically distinct process of π-coordination of the trifluoroborate enabled by these conditions.

Purchased from AmBeed: 395083-14-4 ; 13472-85-0 ; 2093387-36-9 ; 2093536-12-8 ; 835616-62-1 ; 2527-99-3 ; 1010100-26-1 ; 2304513-76-4 ; 20493-60-1 ; 2229976-08-1 ; 153766-81-5 ; 15803-02-8 ; 2509137-01-1 ; 233664-53-4 ; 1334497-00-5 ; 34259-99-9 ; 131274-22-1 ; 92629-11-3 ; 906674-55-3 ; 13682-77-4 ; 1258323-45-3 ; 1111732-84-3 ; 1902198-18-8 ; 30318-99-1 ; 1186667-20-8 ; 166328-14-9 ; 26166-92-7 ; 1216805-49-0 ; 24674-39-3 ; 1111732-99-0

The Fundamental Electrochemical Characteristics of Rare-Earth Cluster-Based Metal–Organic Frameworks

Miller, Lars ;

Abstract: This work explores the synthesis and characterization of redox active rare-earth (RE) metal–organic frameworks (MOFs). MOFs are of interest due to their unique properties including permanent porosity, high surface area, and stability. Redox active MOFs have shown promise in a variety of applications including catalysis and molecular electronics. The second chapter will explore materials composed of Ce(IV) clusters bridged by ditopic carboxylate-based linkers. The synthesis of a series of UiO-66 analogues using the redox active metal Ce(IV) is completed with the original linker benzene-1,4-dicarboxylic acid as well as with various functionalized linkers including: 2-aminobenzene-1,4-dicarboxylic acid, 2-fluorobenzene1,4-dicarboxylic acid, 2-bromobenzene-1,4-dicarboxylic acid, 2,5-dihydroxybenzene-1,4- dicarboxylic acid, and 2,3,5,6-tetrafluorobenzene-1,4-dicarboxylic acid. The electrochemical differences between the analogues is explored via cyclic voltammetry. The third chapter delves into the synthesis of a series of redox active MOFs using the tetratopic tetrathiaflvalene-3,4,5,6-tetrakis(4-benzoic acid) (TTFTBA) redox active linker. Synthesis of a 3D cluster based MOF is attempted using Ce(III/IV), Yb(III), and Lu(III). Two new MOFs with shp topology are synthesized using TTFTBA and Yb(III) or Lu(III). The materials are characterized, and their redox properties are explored.

Purchased from AmBeed: 5798-75-4 ; 445-29-4 ; 31366-25-3 ; 610-92-4 ; 131274-22-1 ; 3906-87-4 ; 652-36-8 ; 586-35-6

Product Details of Tri-tert-butylphosphine tetrafluoroborate

CAS No. :	131274-22-1
Formula :	C₁₂H₂₈BF₄P
M.W :	290.13
SMILES Code :	CC([PH+](C(C)(C)C)C(C)(C)C)(C)C.F[B-](F)(F)F
MDL No. :	MFCD07189501
InChI Key :	YTJUCJAUJCXFTN-UHFFFAOYSA-O
Pubchem ID :	2734635

Safety of Tri-tert-butylphosphine tetrafluoroborate

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Tri-tert-butylphosphine tetrafluoroborate

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 131274-22-1 ]
Downstream synthetic route of [ 131274-22-1 ]

[ 131274-22-1 ] Synthesis Path-Upstream 1~3

1
[ 13716-12-6 ]
[ 131274-22-1 ]

References: [1] Dyes and Pigments, 2011, vol. 91, # 2, p. 182 - 191.
[2] Organic letters, 2001, vol. 3, # 26, p. 4295 - 4298.

2
[ 677-22-5 ]
[ 131274-22-1 ]

References: [1] Synthesis, 2011, # 15, p. 2369 - 2371.

3
[ 13716-12-6 ]
[ 75-05-8 ]
[ 131274-22-1 ]

References: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 37, p. 11929 - 11933[2] Angew. Chem., 2018, vol. 130, # 37, p. 12105 - 12109,5.

[ 131274-22-1 ] Synthesis Path-Downstream 1~18

1
[ 13716-12-6 ]
[ 131274-22-1 ]

References: [1]Dyes and Pigments,2011,vol. 91,p. 182 - 191.
[2]Organic letters,2001,vol. 3,p. 4295 - 4298.

2
[ 38696-20-7 ]
[ 7560-83-0 ]
[ 292638-85-8 ]
[ 131274-22-1 ]
[ 545426-64-0 ]

Yield	Reaction Conditions	Operation in experiment
178 mg (56%)	tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane;	Step A (2E)-3-(2-Phenyl-5-pyrimidinyl)-2-propenoic Acid Methyl Ester Dioxane (1.3 mL) was added to a mixture of <strong>[38696-20-7]5-bromo-2-phenylpyrimidine</strong> (310 mg, 1.32 mmol, prepared as described in Org. Lett. 2002, 4, 513), tri-t-butylphosphonium tetrafluoroborate (11 mg, 0.038 mmol), and tris(dibenzylideneacetone)dipalladium(0) (18 mg, 0.020 mmol). N-Methyldicyclohexylamine (0.31 mL, 1.45 mmol) and methyl acrylate (0.24 mL, 2.67 mmol) were added and the mixture was stirred for 72 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. The residue was triturated with 5:1 hexane/ethyl acetate and the solid was filtered and dried in vacuo to provide 178 mg (56percent) of the title compound as an off-white solid. MS 241 (M+H)+.

References: [1]Patent: US2003/220272,2003,A1 .

3
[ 7560-83-0 ]
[ 623-70-1 ]
[ 131274-22-1 ]
[ 210354-17-9 ]
[ 545426-62-8 ]

Yield	Reaction Conditions	Operation in experiment
0.47 g (70%)	tris-(dibenzylideneacetone)dipalladium(0); In 1,4-dioxane;	Step A (2E)-3-[4-(2-Pyrimidinyl)phenyl]-2-butenoic Acid Ethyl Ester Dioxane (2 mL) was added to a mixture of 2-(4-bromophenyl)pyrimidine (0.59 g, 2.51 mmol, prepared as described in U.S. Pat. No. 5,780,473), tri-t-butylphosphonium tetrafluoroborate (36 mg, 0.12 mmol), and tris(dibenzylideneacetone)dipalladium(0) (57 mg, 0.062 mmol). N-Methyldicyclohexylamine (0.64 mL, 2.99 mmol) and ethyl crotonate (0.62 mL, 4.99 mmol) were added and the mixture was stirred for 18 h at room temperature. The mixture was diluted with ethyl acetate, filtered through a small plug of silica gel which was washed with additional ethyl acetate, and the combined filtrates were concentrated. Purification by chromatography (SiO2, 5:1 hexane/ethyl acetate) provided 0.47 g (70percent) of the title compound as an off-white solid. MS 269 (M+H)+.

References: [1]Patent: US2003/220272,2003,A1 .

4
potassium phosphate [ No CAS ]
aqueous potassium carbonate [ No CAS ]
[ 894794-90-2 ]
[ 5720-07-0 ]
[ 131274-22-1 ]
[ 894794-96-8 ]

Yield	Reaction Conditions	Operation in experiment
	bis(dibenzylideneacetone)-palladium(0); In 1,4-dioxane;	Reference Example 31 tert-Butyl {(3R)-1-[5-(2-chlorobenzyl)-7-(4-methoxyphenyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate Bis(dibenzylideneacetone)palladium (18 mg), tri-tert-butylphosphonium tetrafluoroborate (22 mg), potassium phosphate (329 mg) and 4-methoxyphenylboronic acid (236 mg) were added to a solution of tert-butyl {(3R)-1-[7-bromo-5-(2-chlorobenzyl)-1,3-dimethyl-2,4-dioxo-2,3,4,5-tetrahydro-1H-pyrrolo[3,2-d]pyrimidin-6-yl]piperidin-3-yl}carbamate (90 mg) in dioxane (4 ml), and the resulting mixture was stirred with heating at 50°C for 15 hours. The reaction solution was filtered through Celite and washed with tetrahydrofuran and the filtrate was concentrated under reduced pressure. A 10percent aqueous potassium carbonate solution was added to the residue, followed by two runs of extraction with chloroform (50 ml). The organic layer was dried over sodium sulfate and filtered and the filtrate was concentrated under reduced pressure. The resulting residue was purified by a silica gel column chromatography (hexane / ethyl acetate = 2/1) to obtain the title compound (10 mg). 1H NMR (300 MHz, CDCl3) delta 7.41-7.37 (m, 1H), 7.26-7.10 (m, 4H), 6.92 (d, J = 8.8 Hz, 1H), 6.52-6.50 (m, 1H), 5.80 (d, J = 16.7 Hz, 1H), 5.66 (d, J = 16.7 Hz, 1H), 3.87 (s, 3H), 3.52-3.50 (m, 1H), 3.37 (s, 3H), 3.07 (s, 3H), 2.80-2.40 (m, 4H), 1.62-1.39 (m, 4H), 1.38 (s, 9H). MS (ESI+) 608 (M++1, 76percent).

References: [1]Patent: EP1829877,2007,A1 .

5
[ 120-72-9 ]
potassium phosphate [ No CAS ]
[ 890315-75-0 ]
[ 131274-22-1 ]
[ 564483-18-7 ]
[ 890313-93-6 ]