[ CAS No. 273731-82-1 ] {[proInfo.proName]}

Name: 273731-82-1|5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehyde|98%
Brand: Ambeed
SKU: A693690
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Quality Control of [ 273731-82-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 273731-82-1 ]

SDS Specification

Alternatived Products of [ 273731-82-1 ]

Product Details of [ 273731-82-1 ]

CAS No. :	273731-82-1	MDL No. :	MFCD16295105
Formula :	C₁₁H₁₅BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VSQZZPPWTRWPTM-UHFFFAOYSA-N
M.W :	222.05	Pubchem ID :	53217094
Synonyms :

Calculated chemistry of [ 273731-82-1 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.55
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.57
TPSA :	48.67 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.8
Log Po/w (WLOGP) :	1.39
Log Po/w (MLOGP) :	-0.31
Log Po/w (SILICOS-IT) :	1.42
Consensus Log Po/w :	0.86

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.45
Solubility :	0.788 mg/ml ; 0.00355 mol/l
Class :	Soluble
Log S (Ali) :	-2.44
Solubility :	0.804 mg/ml ; 0.00362 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.17
Solubility :	0.152 mg/ml ; 0.000682 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.35

Safety of [ 273731-82-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 273731-82-1 ]

* 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.

Downstream synthetic route of [ 273731-82-1 ]

[ 273731-82-1 ] Synthesis Path-Downstream 1~18

1
[ 273731-82-1 ]
[ 104-94-9 ]
C₁₈H₂₂BNO₄ [ No CAS ]

Reference： [1]Heteroatom Chemistry,2009,vol. 20,p. 56 - 63

2
[ 273731-82-1 ]
[ 1393677-08-1 ]
(S)-2-(tert-butyloxycarbonylamino)-5-(fur-2-yl)pent-4-enoic acid [ No CAS ]
(S)-2-(tert-butyloxycarbonylamino)-5-(fur-2-yl)pent-4-enoic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2013,p. 7960 - 7972

3
[ 273731-82-1 ]
[ 231278-20-9 ]
[ 231278-84-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With palladium 10% on activated carbon; N-ethyl-N,N-diisopropylamine; In methanol; for 8h;Reflux;	Example 65-(4-(3-Chloro-4-(3-fluorobenzyloxy)phenylam ino)ch inazolin-6-yl)furan-2-carbaldehyde IIII (3.3 g, 6.42 mmol), 10 % Pd/C (78 mg, 0.07 mmol, 1.2 mol. %), methanol (45 ml), N,N-diisopropylethylamine (2.2 ml, 12.85 mmol, 2 equiv.) were added to the ester Vila (1.8 g, 8.35 mmol, 1.3 equiv.) and the resulting suspension was refluxed for 8 hours.After cooling to the room temperature the yellow suspension was filtered and washed with methanol (3 X 20 ml). The product was subsequently dissolved in THF (45 ml) and filtered through a kieselguhr layer, which, after evaporation of the solvent, WO 2014/059956 PCT/CZ2013/000132provided 2.6 g (87 %) of the title compound (I) as a yellow powdery substance. HPLCpurity: 95%1H NMR (500 MHz, DMSOd6): 5.27 (s, 2 H), 7.16-7.20 (m, I H), 7.28-7.35 (m, 3H)7.43 (d, J = 3.7 Hz, 1 H), 7.45-7.48 (m, I H), 7.71-7.74 (m, 2 H), 7.46 (d, J = 3.56 Hz,H), 7.85 (J = 8.7 Hz, 1H), 8.00 (J = 2.4 Hz, 1H), 8.29 (dd, J = 1.8 Hz, J = 8.7 Hz),8.59 (s, 1H), 8.99 (d, J= 1.5 Hz, IH), 9.67 (s, 1H), 10.14 (s, IH).

Reference： [1]Patent: WO2014/59956,2014,A1 .Location in patent: Page/Page column 9; 10

4
[ 13529-27-6 ]
[ 61676-62-8 ]
[ 273731-82-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example I5-(4,4, 5, 5-Tetramethyl- 1, 3,2-dioxaborolan-2-yl)furan-2-carbaldehyde (VIla)A 2.5M solution of butyllithium in hexanes (50 ml, 0.125 mol) was added to a solution of <strong>[13529-27-6]diethylacetal furan-2-carbaldehyde</strong> (17.0 g, 0.1 mol) in dimethoxyethane (100 mL) with a linear dispenser at the temperature of -50C during 1 hour and the mixture wasstirred under nitrogen at this temperature for 4 hours. Then, 2-isopropoxy-4,4,5,5- tetramethyl-l,3,2-dioxaborolane (24.0 g, 0.129 mol) was added with a linear dispenser during 30 minutes and the mixture was stirred at -40C for 2 hours and then stirred without cooling under nitrogen for 4 hours (the internal temperature rose to 20C). 2.5M HCI (100 ml) was added dropwise to the dark reaction mixture and themixture was stirred at the room temperature for 30 minutes. After addition of ethyl acetate (200 ml), the organic layer was separated and the aqueous layer was shaken with ethyl acetate (2 x 25 ml). The combined organic fractions were washed with water (4 x 25 ml) and dried with MgSO4. 18.3 g of the crude product was obtained containing, according to HPLC, 96.8% of the desired compound in the form of ayellowish liquid. The product contained 2-3% of the corresponding boronic acid. If it is undesired, it can be easily removed by addition of a small amount of pinacol to a solution of the crude compound VIla in a suitable solvent.1H NMR (250 MHz, DMSOd6): 1.30(s, 12 H), 7.23(d, J= 3.6 Hz, IH), 7.51 (d, J3.6 Hz, I H), 9.71 ppm (s, 1 H).

Reference： [1]Patent: WO2014/59956,2014,A1 .Location in patent: Page/Page column 7

5
[ 273731-82-1 ]
[ 231277-92-2 ]

Reference： [1]Patent: WO2014/59956,2014,A1

6
[ 76-09-5 ]
[ 27329-70-0 ]
[ 273731-82-1 ]

Yield	Reaction Conditions	Operation in experiment
70%	In tetrahydrofuran; at 20℃; for 2h;	Example 25-(4,4, 5, 5-Tetramethyl- 1, 3,2-d ioxaborolan-2-yl)furan-2-carbaldehyde Vila5-Formylfuran-2-yl boronic acid (139 mg, 1.47 mmol) was suspended in dry THF (4.4 ml), subsequently anhydrous pinacol (174 mg, 1.47 mmol, I equiv.) was added and the reaction mixture was stirred at the room temperature for 2 hours. The resulting solution was filtered and evaporated at a reduced pressure, which provided 228 mg (70%) of the title compound VIla in the form of yellowish oil.1H NMR (250 MHz, DMSO-d6): 1.30 (s, 12 H), 7.23 (d, J = 3.60 Hz, IH), 7.51 (d, J =3.60 Hz, I H), 9.71 ppm (s, 1 H).

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 17890 - 17896
[2]Patent: WO2014/59956,2014,A1 .Location in patent: Page/Page column 8
[3]Chemical Communications,2019,vol. 55,p. 10567 - 10570

7
[ 273731-82-1 ]
[ 171082-32-9 ]
C₂₂H₂₂BN₃O₄ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 17890 - 17896

8
[ 273731-82-1 ]
tert-butyl ((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-yl)methyl)carbamate [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 10567 - 10570

9
[ 273731-82-1 ]
C₁₁H₁₆BNO₄ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 10567 - 10570

10
[ 273731-82-1 ]
C₁₁H₁₈BNO₃*C₂HF₃O₂ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 10567 - 10570

11
[ 1899-24-7 ]
[ 73183-34-3 ]
[ 273731-82-1 ]

Reference： [1]Organic Letters,2021,vol. 23,p. 2320 - 2325

12
[ 611-32-5 ]
[ 273731-82-1 ]
4-(quinolin-8-ylmethyl)furan-2-carbaldehyde [ No CAS ]

Reference： [1]Organic Letters,2021,vol. 23,p. 7177 - 7182

13
[ 273731-82-1 ]
[ 2927-71-1 ]
5-(2-chloro-5-fluoropyrimidin-4-yl)furan-2-carbaldehyde [ No CAS ]