[ CAS No. 825644-26-6 ] {[proInfo.proName]}

Name: 825644-26-6|(4-Fluoro-2-formylphenyl)boronic acid|95%
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SKU: A177588
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Quality Control of [ 825644-26-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 825644-26-6 ]

SDS Specification

Alternatived Products of [ 825644-26-6 ]

Product Details of [ 825644-26-6 ]

CAS No. :	825644-26-6	MDL No. :	MFCD10697426
Formula :	C₇H₆BFO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QWUBOCQWTPCPNE-UHFFFAOYSA-N
M.W :	167.93	Pubchem ID :	25185241
Synonyms :

Calculated chemistry of [ 825644-26-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	41.61
TPSA :	57.53 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.05 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.39
Log Po/w (WLOGP) :	-0.26
Log Po/w (MLOGP) :	0.08
Log Po/w (SILICOS-IT) :	-0.16
Consensus Log Po/w :	0.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.36
Solubility :	7.25 mg/ml ; 0.0432 mol/l
Class :	Very soluble
Log S (Ali) :	-1.16
Solubility :	11.5 mg/ml ; 0.0685 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	5.2 mg/ml ; 0.031 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 825644-26-6 ]

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 [ 825644-26-6 ]

* 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 [ 825644-26-6 ]
Downstream synthetic route of [ 825644-26-6 ]

[ 825644-26-6 ] Synthesis Path-Upstream 1~4

1
[ 150-46-9 ]
[ 933585-18-3 ]
[ 825644-26-6 ]

Yield	Reaction Conditions	Operation in experiment
89.5%	Stage #1: With n-butyllithium In tetrahydrofuran; diethyl ether; hexane at -75 - -70℃; Stage #2: at -70℃; Stage #3: With hydrogenchloride In tetrahydrofuran; diethyl ether; hexane; water at -70 - 5℃;	2-Bromo-5-fluorobenzaldehyde (20.0 g, 98.5 mmol) was dissolved in 40 ml of methanol. 0.5 ml of concentrated H₂SO₄ was added and 13.6 g (128 mmol) of trimethyl orthoformate was added dropwise. The solution was refluxed for 1 h and left to cool down. Then the solution was brought to pH 11 with a concentrated solution of NaOMe in methanol. After distillation of the volatiles the product was distilled under vacuum to give 23.8 g of 1-bromo-2-(dimethoxymethyl)-4-fluorobenzene as a colorless liquid (yield 96.9percent). ¹H NMR (CDCl₃, 500 MHz), δ/ppm: 7.51 (m, 1H), 7.35 (m, 1H), 6.93 (m, 1H), 5.50 (s, 1H), 3.38 (s, 6H). 23.8 g (95.0 mmol) of the above compound was dissolved in 200 ml of dry Et₂O and 40 ml THF under argon flow. The solution was cooled down to −75 °C using dry ice/acetone bath. 2.5 M n-butyllithium in hexanes (42.0 ml, 110.0 mmol) was added dropwise to keep the temperature under −70 °C. The solution was stirred for 1 h, then 16.1 g (110.0 mmol) of triethyl borate was added slowly, keeping the temperature under −70 °C. Cooling bath was removed and the solution was brought to pH 3 with 3 M aq. HCl, while the temperature rose to 5 °C. The aqueous layer was separated and extracted with Et₂O (2 × 50 ml). The organic layers were combined and the solvent was partially removed under vacuum. Distillation was continued after addition of water. The solid precipitated after cooling was filtered and dried on air, giving 14.3 g of 4-fluoro-2-formylphenylboronic acid (2) (yield 89.5percent). ¹¹B NMR (64 MHz, acetone-d₆): δ = 30.9 ppm. Compounds 1, 3 and 4 were synthesized in similar way from the appropriate fluoro-substituted 2-bromobenzaldehydes. Overall (two-steps) yields are as follows: 1: 85.4percent, 3: 78.3percent, 4: 92.1percent.

Reference： [1] Journal of Fluorine Chemistry, 2016, vol. 187, p. 1 - 8

2
[ 773094-69-2 ]
[ 825644-26-6 ]

Yield	Reaction Conditions	Operation in experiment
77%	Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -74 - -70℃; for 1 h; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane at -70 - 15℃; for 2 h; Stage #3: With hydrogenchloride; water In tetrahydrofuran; hexane at 60℃; for 1 h;	To a solution of 2.30 g (9.31 mmol) 2- (2-BROMO-5-FLUORO-PHENYL)- [1, 3] dioxolane in 15 ml tetrahydrofuran was added dropwise AT-70 °C 6.11 ml (9.77 mmol) of a 1.6 M solution of n-butyllithium in hexane. The reaction mixture was stirred AT-74 °C for 1 h. After dropwise addition of 2.65 ml (11.2 mmol) triisopropyl borate AT-70 °C the reaction mixture was allowed to warm to 15 °C during a period of 2 h. Water (7 ml) was added, and the mixture was acidified to pH I by addition of 37percent hydrochloric acid solution. After heating at 60 °C for 1 h, the mixture was cooled to room temperature and extracted with three 50-ml portions of diethyl ether. The combined organic layers were washed with 50 ml brine, dried over sodium sulfate and concentrated. Flash chromatography gave 1.2 g (77percent) of the title compound as a light yellow liquid. MS m/e (percent): 167 (M+, 1)

Reference： [1] Patent: WO2005/2577, 2005, A1, . Location in patent: Page 224-225

3
[ 94569-84-3 ]
[ 825644-26-6 ]

Reference： [1] European Journal of Organic Chemistry, 2013, # 12, p. 2316 - 2324
[2] Journal of Fluorine Chemistry, 2016, vol. 187, p. 1 - 8

4
[ 5419-55-6 ]
[ 94569-84-3 ]
[ 825644-26-6 ]

Reference： [1] Patent: CN104478723, 2016, B, . Location in patent: Paragraph 0069; 0070

[ 825644-26-6 ] Synthesis Path-Downstream 1~88

1
[ 773094-69-2 ]
[ 825644-26-6 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a solution of 2.30 g (9.31 mmol) 2- (2-BROMO-5-FLUORO-PHENYL)- [1, 3] dioxolane in 15 ml tetrahydrofuran was added dropwise AT-70 C 6.11 ml (9.77 mmol) of a 1.6 M solution of n-butyllithium in hexane. The reaction mixture was stirred AT-74 C for 1 h. After dropwise addition of 2.65 ml (11.2 mmol) triisopropyl borate AT-70 C the reaction mixture was allowed to warm to 15 C during a period of 2 h. Water (7 ml) was added, and the mixture was acidified to pH I by addition of 37% hydrochloric acid solution. After heating at 60 C for 1 h, the mixture was cooled to room temperature and extracted with three 50-ml portions of diethyl ether. The combined organic layers were washed with 50 ml brine, dried over sodium sulfate and concentrated. Flash chromatography gave 1.2 g (77%) of the title compound as a light yellow liquid. MS m/e (%): 167 (M+, 1)

Reference： [1]Patent: WO2005/2577,2005,A1 .Location in patent: Page 224-225

2
C₁₁H₁₆BFO₄ [ No CAS ]
[ 825644-26-6 ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430

3
[ 825644-26-6 ]
[ 13171-64-7 ]
[ 618-36-0 ]
C₂₁H₂₁BFNO₆ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9395 - 9395

4
[ 825644-26-6 ]
[ 4217-66-7 ]
[ 618-36-0 ]
C₂₄H₂₃BFNO₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9395 - 9395

5
[ 825644-26-6 ]
[ 22422-34-0 ]
[ 618-36-0 ]
C₂₅H₂₉BFNO₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430

6
[ 825644-26-6 ]
[ 3886-69-9 ]
[ 143505-39-9 ]
C₂₅H₂₃BFNO₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430

7
[ 825644-26-6 ]
[ 3886-69-9 ]
[ 124649-67-8 ]
C₂₅H₂₃BFNO₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430

8
[ 825644-26-6 ]
[ 25779-13-9 ]
[ 618-36-0 ]
C₂₃H₂₁BFNO₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9395 - 9395

9
[ 825644-26-6 ]
[ 124649-67-8 ]
[ 618-36-0 ]
C₂₅H₂₃BFNO₄ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9395 - 9395

10
[ 825644-26-6 ]
[ 18531-94-7 ]
[ 618-36-0 ]
C₃₅H₂₅BFNO₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9395 - 9395

11
[ 825644-26-6 ]
[ 103548-16-9 ]
[ 618-36-0 ]
C₂₄H₂₃BFNO₂ [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 427 - 430
[2]Journal of Organic Chemistry,2019,vol. 84,p. 9395 - 9395

12
[ 73290-22-9 ]
[ 825644-26-6 ]
C₁₉H₁₁F₂NO₂ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 4815 - 4818
[2]European Journal of Organic Chemistry,2013,p. 2316 - 2324

13
[ 825644-26-6 ]
[ 1204417-14-0 ]