[ CAS No. 105365-51-3 ] {[proInfo.proName]}

Name: 105365-51-3|(4-Butoxyphenyl)boronic acid|98%
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SKU: A220016
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Quality Control of [ 105365-51-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 105365-51-3 ]

SDS Specification

Alternatived Products of [ 105365-51-3 ]

Product Details of [ 105365-51-3 ]

CAS No. :	105365-51-3	MDL No. :	MFCD03427054
Formula :	C₁₀H₁₅BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QUPFQMXWFNJUNJ-UHFFFAOYSA-N
M.W :	194.04	Pubchem ID :	3836310
Synonyms :

Calculated chemistry of [ 105365-51-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	5
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	57.18
TPSA :	49.69 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.05
Log Po/w (WLOGP) :	0.55
Log Po/w (MLOGP) :	0.95
Log Po/w (SILICOS-IT) :	0.28
Consensus Log Po/w :	0.76

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.32
Solubility :	0.925 mg/ml ; 0.00477 mol/l
Class :	Soluble
Log S (Ali) :	-2.72
Solubility :	0.368 mg/ml ; 0.0019 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.63
Solubility :	0.451 mg/ml ; 0.00232 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.95

Safety of [ 105365-51-3 ]

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 [ 105365-51-3 ]

* 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 [ 105365-51-3 ]
Downstream synthetic route of [ 105365-51-3 ]

[ 105365-51-3 ] Synthesis Path-Upstream 1~3

1
[ 105365-51-3 ]
[ 122-94-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With dihydrogen peroxide In acetonitrile at 30 - 35℃; for 0.166667 h; Schlenk technique	General procedure: an oven-dried Schlenk flask was allowed to cool to room temperature and charged sequentially with arylboronic acid (1 mmol), MeCN (3.0 mL) and silica chloride (0.5 mmol). The reaction was then activated by addition of 30percent H₂O₂ (1.0 equiv.) and stirred at 30–35 °C for the required time as given in Table 5. The progress of reaction was monitored by TLC. After complete conversion of starting material, the reaction mixture was filtered to remove silica gel. The reaction mixture was neutralized with 5percent NaHCO₃ solution (5 mL). Then the product was extracted with ethyl acetate (30 mL) and subsequently washed with distilled water (10 mL). The organic extract was dried over Na₂SO₄ and the solvent was removed under reduced pressure. The resultant product was purified by column chromatography using silica gel with n-hexane and ethyl acetate as solvent to get the pure product. The structure of the product was confirmed by GC–MS, M.P. and ¹H NMR spectroscopic techniques.

Reference： [1] Tetrahedron Letters, 2017, vol. 58, # 33, p. 3323 - 3326

2
[ 39969-57-8 ]
[ 105365-51-3 ]

Reference： [1] Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals, 2003, vol. 391, p. 41 - 56

3
[ 109-65-9 ]
[ 106-41-2 ]
[ 105365-51-3 ]

Reference： [1] Chemistry - A European Journal, 2013, vol. 19, # 7, p. 2370 - 2383

[ 105365-51-3 ] Synthesis Path-Downstream 1~88

1
[ 872409-99-9 ]
[ 105365-51-3 ]
[ 872410-02-1 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 16578 - 16591

2
[ 855120-18-2 ]
[ 105365-51-3 ]
[ 872410-03-2 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 16578 - 16591

4
[ 29022-11-5 ]
[ 82565-68-2 ]
[ 105365-51-3 ]
2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid tert-butyl ester [ No CAS ]
[(5S,10bR)-9-(4-Butoxy-phenyl)-3-oxo-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline-5-carbonyl]-amino}-acetic acid [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7959 - 7962

5
[ 29022-11-5 ]
[ 82565-68-2 ]
[ 105365-51-3 ]
2-(2-carboxy-ethyl)-[1,3]oxazinane-3-carboxylic acid tert-butyl ester [ No CAS ]
2-{2-[2-(4'-butoxy-biphenyl-4-yl)-1-(carboxymethyl-carbamoyl)-ethylcarbamoyl]-ethyl}-[1,3]oxazinane-3-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7959 - 7962

6
[ 4701-17-1 ]
[ 105365-51-3 ]
[ 940953-38-8 ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1521 - 1527

7
C₃₉H₂₈Br₂N₄O₂Si^(2-)*Zn⁽²⁺⁾ [ No CAS ]
[ 105365-51-3 ]
C₅₉H₅₄N₄O₄Si^(2-)*Zn⁽²⁺⁾ [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 5742 - 5744

8
[ 105365-51-3 ]
(1R,2R)-N-[1-[2,2']Bithiophenyl-5-yl-meth-(E)-ylidene]-N'-[1-[5-(4-butoxy-phenyl)-thiophen-2-yl]-meth-(E)-ylidene]-cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1521 - 1527

9
[ 105365-51-3 ]
N-[2,2']bithiophenyl-5-ylmethyl-N'-[5-(4-butoxy-phenyl)-thiophen-2-ylmethyl]-cyclohexane-1,2-diamine [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2006,vol. 348,p. 1521 - 1527

10
[ 105365-51-3 ]
4-[5-(4-butoxy-benzylidene)-[1,3]dioxan-2-yl]-1-decyl-pyridinium; iodide [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1137 - 1140

11
[ 105365-51-3 ]
4-[5-(4-butoxy-benzylidene)-[1,3]dioxan-2-yl]-1-decyl-pyridinium; iodide [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 1137 - 1140

12
[ 105365-51-3 ]
[ 287738-70-9 ]

Reference： [1]Chemical Communications,2003,p. 974 - 975

13
[ 105365-51-3 ]
2'-bromomethyl-4,4''-dibutoxy-[1,1';4',1'']terphenyl [ No CAS ]

Reference： [1]Chemical Communications,2003,p. 974 - 975

14
[ 105365-51-3 ]
C₅₀H₆₆N₄O₄ [ No CAS ]

Reference： [1]Organic Letters,2002,vol. 4,p. 513 - 516

15
[ 14221-01-3 ]
[ 105365-51-3 ]
2-(4-butoxyphenyl)5-nitrothiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With sodium carbonate;	Step 9.3 2-(4-butoxyphenyl)5-nitrothiophene. Quantities: <strong>[105365-51-3]4-butoxy-1-phenylboronic acid</strong> (3.38 g, 0.017 mol), compound of compound of step 9.2 (3.31 g, 0.016 mol), tetrakis (triphenylphosphine) palladium(O) (0.910 g, 0.001 mol), sodium carbonate (15.8 ml, 2.0M, 0.03 mol). The experimental procedure is carried out as described in step 8.3 above. The product was purified by column chromatography ?silica gel/petroleum fraction (bp 40-60 C.), dichloromethane, 3:1! and was recrystallized from ethanol to give 4.57 g (94% yield) of pale yellow solid which was dried in vacuo (P2 O5).

Reference： [1]Patent: US5888421,1999,A

16
[ 874305-22-3 ]
[ 105365-51-3 ]
Zn(CH₃C(O)OC₆H₄C₂₀H₈N₄(C₆H₄O(CH₂)3CH₃)2C₆H₄CCSi(CH₃)3) [ No CAS ]

Reference： [1]Chemical Communications,2005,p. 5742 - 5744

17
2-octyl-1,1,3,3-tetradeuterio-1,3-propanediol [ No CAS ]
[ 105365-51-3 ]
2-(4-butoxyphenyl)-5-octyl-4,4,6,6-tetradeuterio-1,3,2-dioxaborinane [ No CAS ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2103 - 2108

18
[ 1034017-97-4 ]
[ 105365-51-3 ]
3',5'-dibenzyloxy-4-butoxy-2'-methoxymethoxy-p-terphenyl [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 5331 - 5344

19
[ 1034017-51-0 ]
[ 105365-51-3 ]
[ 1034017-55-4 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 5331 - 5344

20
[ 876913-90-5 ]
[ 105365-51-3 ]
[ 876913-94-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2315 - 2319

21
[ 106-40-1 ]
[ 105365-51-3 ]
[ 101286-63-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2315 - 2319

22
[ 107-21-1 ]
[ 105365-51-3 ]
[ 1193708-95-0 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7217 - 7220
Angewandte Chemie,2009,vol. 121,p. 7353 - 7356

23
[ 200055-89-6 ]
[ 105365-51-3 ]
[ 1196530-97-8 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 5374 - 5377

24
[ 1178858-55-3 ]
[ 105365-51-3 ]
[ 1178858-58-6 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 4757 - 4773

25
[ 54063-49-9 ]
[ 105365-51-3 ]
[ 1184304-23-1 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 5044 - 5057

26
[ 108-05-4 ]
[ 105365-51-3 ]
[ 105337-03-9 ]

Reference： [1]Synlett,2009,p. 3151 - 3154

27
[ 870521-18-9 ]
[ 105365-51-3 ]
C₃₁H₃₀F₃NO₆S [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 77 - 105

28
[ 1227366-41-7 ]
[ 105365-51-3 ]
[ 1246518-73-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1-methyl-pyrrolidin-2-one; water; at 220℃; for 4h;Inert atmosphere;	Under nitrogen atmosphere, 0.14 g (0.12 mmol) of tetrakistriphenylphosphine palladium(0) is dissolved in 100 ml of NMP in a 300 ml three-necked flask. 1.85 g (4.0 mmol) of Compound IV-a, 8.0 ml of a 2M sodium carbonate aqueous solution, and 1.71 g (8.8 mmol) of 4-n-butoxyphenyl borate are sequentially added, in this order, to the solution in the flask. The resultant mixture is refluxed for 4 hours in an oil bath at 220 C. under stirring by a magnetic stirrer. The completion of the reaction is confirmed by 1H-NMR, the reaction solution is cooled to 25 C., and the reaction solution is poured into 1 L of pure water in a 2 L beaker. The resultant mixture in the beaker is stirred at 25 C. for 20 minutes using a magnetic stirrer. After completion of the stirring, the precipitated crystal is collected by suction filtration, and is washed with 1 L of pure water. The obtained crystal is further washed with 200 ml of methanol, and then with 250 ml of toluene, and then vacuum-dried at 60 C. for 15 hours. 150 ml of NMP is added to the crystal, and recrystallization is performed, followed by purification by sublimation. As the result, Exemplary Compound 11 in the form of an orange crystal is obtained in an amount of 1.0 g. The IR spectrum and 1H-NMR spectrum of the obtained Exemplary Compound 11 are shown in FIGS. 3 and 4, respectively.

Reference： [1]Patent: US2010/137611,2010,A1 .Location in patent: Page/Page column 10

29
[ 331678-10-5 ]
[ 105365-51-3 ]
[ 1227952-57-9 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 3736 - 3741

30
[ 956485-90-8 ]
[ 105365-51-3 ]
[ 1234510-74-7 ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 3598 - 3600

31
C₁₇H₁₉BrN₂O [ No CAS ]
[ 105365-51-3 ]
C₂₇H₃₂N₂O₂ [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 3598 - 3600

32
[ 128-63-2 ]
[ 105365-51-3 ]
[ 1237525-20-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 3292 - 3295

33
[ 916516-94-4 ]
[ 105365-51-3 ]
[ 1222498-29-4 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3154 - 3168

34
[ 845550-72-3 ]
[ 105365-51-3 ]
[ 1222498-44-3 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3154 - 3168

35
[ 1200445-94-8 ]
[ 105365-51-3 ]
[ 1200445-95-9 ]

Reference： [1]Langmuir,2010,vol. 26,p. 3615 - 3622

36
[ 35578-47-3 ]
[ 105365-51-3 ]
[ 1258434-21-7 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 46 - 49

37
[ 35578-47-3 ]
[ 105365-51-3 ]
[ 1258434-15-9 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 46 - 49

38
[ 1262404-12-5 ]
[ 105365-51-3 ]
C₃₉H₅₆N₂O₂ [ No CAS ]

Reference： [1]New Journal of Chemistry,2010,vol. 34,p. 2892 - 2896

39
C₂₉H₄₅BrN₆O₆ [ No CAS ]
[ 105365-51-3 ]
C₃₉H₅₈N₆O₇ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 3041 - 3049

40
[ 99-90-1 ]
[ 105365-51-3 ]
[ 56117-00-1 ]

Yield	Reaction Conditions	Operation in experiment
79%	With palladium diacetate; triphenylphosphine; In propan-1-ol; water; at 100℃; for 2h;	[0289] Briefly, to a solution of 4-bromoacetophenone, 8.25 g (41.4 mmol), 4- butoxyphenylboronic acid, 8.85 g (45.54 mmol) in 1 -propanol (150 ml), palladium acetate (70 mg), triphenylphosphine (246 mg), sodium carbonate solution (aq. 2.0 M, 70 ml), and water(45 ml) were added in order. The reaction mixture was stirred in 100C oil bath for 2 hour, cooled to room temperature, and then put the reaction flask in ice bath for 2 hours. The white crystals were collected by filtration, washed with cooled water and dried. The crude product was washed with diethyl ether and dissolved in DCM, passed a short silica gel column to remove palladium. Pure priduct, 1-(4?-butoxy-[1 ,T-biphenyl]-4-yl)ethan-1-one, 8.8 g (yield 79%) as off-white solid. 1H NMR (CDCb): d (ppm) 1.01 (t, 3H, CH3), 1.50-1.57 (m, 2H, CH2), 1.77-1.84 (m, 2H, CH2), 2.64 (s, 3H, CH3), 4.04 (t, 2H, OCH2), 6.99 (d, 2H, arom., J=8.7 Hz), 7.57 (d, 2H, arom., J=8.7 Hz), 7.65 (d, 2H, arom., J=8.7 Hz), 8.01 (d, 2H, arom., J=8.7 Hz).

Reference： [1]Patent: WO2019/246603,2019,A1 .Location in patent: Paragraph 0276; 0288-0289
[2]Chemical Communications,2011,vol. 47,p. 9206 - 9208

41
[ 1370619-09-2 ]
[ 105365-51-3 ]
[ 1370619-10-5 ]