[ CAS No. 131274-22-1 ] {[proInfo.proName]}

Name: 131274-22-1|Tri-tert-butylphosphonium tetrafluoroborate|98%
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SKU: A198422
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Quality Control of [ 131274-22-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 131274-22-1 ]

SDS Specification

Alternatived Products of [ 131274-22-1 ]

Product Details of [ 131274-22-1 ]

CAS No. :	131274-22-1	MDL No. :	MFCD07189501
Formula :	C₁₂H₂₈BF₄P	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YTJUCJAUJCXFTN-UHFFFAOYSA-O
M.W :	290.13	Pubchem ID :	2734635
Synonyms :		Chemical Name :	Tri-tert-butylphosphonium tetrafluoroborate

Calculated chemistry of [ 131274-22-1 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	79.47
TPSA :	13.59 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	5.11
Log Po/w (WLOGP) :	7.58
Log Po/w (MLOGP) :	5.02
Log Po/w (SILICOS-IT) :	3.01
Consensus Log Po/w :	4.14

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	0.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.66
Solubility :	0.00635 mg/ml ; 0.0000219 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.14
Solubility :	0.00211 mg/ml ; 0.00000726 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-3.63
Solubility :	0.068 mg/ml ; 0.000234 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.59

Safety of [ 131274-22-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 131274-22-1 ]

* 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 ]

Reference： [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 ]

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

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

Reference： [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 1~21

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

Reference： [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 5-bromo-2-phenylpyrimidine (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). <strong>[7560-83-0]N-Methyldicyclohexylamine</strong> (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)+.

Reference： [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). <strong>[7560-83-0]N-Methyldicyclohexylamine</strong> (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)+.

Reference： [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).

Reference： [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 ]