[ CAS No. 1150561-77-5 ]

Name: 1150561-77-5|Methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)propanoate|98%
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Quality Control of [ 1150561-77-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1150561-77-5 ]

SDS Specification

Alternatived Products of [ 1150561-77-5 ]

Product Details of [ 1150561-77-5 ]

CAS No. :	1150561-77-5	MDL No. :	MFCD10700159
Formula :	C₁₀H₁₉BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	214.07	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 1150561-77-5 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	58.41
TPSA :	44.76 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) :	-6.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.43
Log Po/w (WLOGP) :	1.64
Log Po/w (MLOGP) :	0.46
Log Po/w (SILICOS-IT) :	0.79
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) :	-1.8
Solubility :	3.36 mg/ml ; 0.0157 mol/l
Class :	Very soluble
Log S (Ali) :	-1.98
Solubility :	2.27 mg/ml ; 0.0106 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.37
Solubility :	0.909 mg/ml ; 0.00425 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.91

Safety of [ 1150561-77-5 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1150561-77-5 ]

* 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 [ 1150561-77-5 ]

[ 1150561-77-5 ] Synthesis Path-Downstream 1~26

1
[ 1150561-77-5 ]
potassium 3-trifluoroboratopropionate methyl ester [ No CAS ]

Reference： [1]Organic Letters,2008,vol. 10,p. 1795 - 1798

2
[ 292638-85-8 ]
[ 73183-34-3 ]
[ 1150561-77-5 ]

Yield	Reaction Conditions	Operation in experiment
92%		Example 15: beta-Boration of methyl acrylate to methyl-3-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan- 2-yl)-propanoate in water: In a dry two-necked round bottom flask were placed catalyst CuC03 basic (0.03 mmol, 3 mol% according to starting material) and ligand Ph3P (0.035 mmol, 3.5 mol% according to starting material) under the nitrogen. Afterwards 2.5 mL of deionized water was added and reaction mixture was vigorously (900 rpm) stirred at ambient temperature for 20 min. The boronating reagent bis(pinacolato)diboron (B2pin2; 1 .1 mmol, 280 mg, 1 .1 equiv.) was added in one portion and such reaction mixture was stirred at ambient temperature for 30 min. Starting material methyl acrylate (1 .0 mmol, 86 mg) was slowly added into the reaction system and such reaction mixture was intensively stirred at 27 C for 12 hours. The reaction mixture was diluted with brine (5 mL) and extracted with EtOAc (2 x 40 mL). Combined organic layers were again washed with brine (30 mL), dried over Na2S04 and organic solvent was removed under the reduced pressure. The crude product was purified with column chromatography (Si02; n-hexane : EtOAc = 9 : 1 ) to obtain 1 97 mg (92%, yield) of pure oily product as determined with 1 H, 11 B, 13C NMR and MS analysis. 1 H NM R (500 MHz, CDCI3, ppm) delta = 3.66 (s, 3H), 2.48 (t, J =7.6 Hz, 2H), 1 .21 (s, 12H), 0.98 (t, J = 7.5 Hz, 2H); 11 B (160 M Hz, CDCI3, ppm) delta = 33.7 (bs); 13C (125 MHz, CDCI3, ppm) delta = 175.1 , 83.2, 51 .5, 28.6, 24.8, 24.7, 24.5, 24.1 , 6.2 (broad, C-B);
92%		In a dry two-necked round bottom flask were placed catalyst CuCO3 (0.03 mmol, 7.50 mg, 3 mol% according to starting material) and ligand Ph3P (0.035 mmol, 8.8 mg, 3.5 mol% according to starting material) under the nitrogen. Afterwards 2.5 mL of deionized water was added and reaction mixture was vigorously (900 rpm) stirred at ambient temperature for 20 min. The boronating reagent bis(pinacolato)diboron (1.1 mmol, 280.0 mg, 1.1 equiv.) was added in one portion and such reaction mixture was stirred at ambient temperature for 30 min. Starting material methyl acrylate (1.0 mmol) was slowly added into the reaction system and such reaction mixture was intensively stirred at 27 C for 12 hours. The reaction mixture was diluted with brine (5 mL) and extracted with EtOAc (2 x 40 mL). Combined organic layers were again washed with brine (30 mL), dried over Na2SO4 and organic solvent was removed under the reduced pressure. The crude product was purified with column chromatography (SiO2; n-hexane: EtOAc = 9: 1) to obtain 197 mg (92%, yield) of pure oily product as determined with 1H, 11B, 13C NMR and MS analysis. 1H NMR (500 MHz, CDCl3, ppm) delta = 3.66 (s, 3H), 2.48 (t, J =7.6 Hz, 2H), 1.21 (s, 12H), 0.98 (t, J = 7.5 Hz, 2H); 11B (160 MHz, CDCl3, ppm) delta = 33.7 (bs); 13C (125 MHz, CDCl3, ppm) delta = 175.1, 83.2, 51.5, 28.6, 24.8, 24.7, 24.5, 24.1, 6.2 (broad, C-B);
42%		Preparation of methyl 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)propanoate A mixture of copper(I) chloride (0.172 g, 1.742 mmol), sodium tert- butoxide (0.558 g, 5.81 mmol) and bis(2-diphenylphosphino)ferrocene (0.938 g, 1.742 mmol) in THF (8 ml) was purged with N2 for 30min and stirred at room temperature for 45 min. Bis(pinacolato)diboron (16.22 g, 63.9 mmol) in THF (17ml) was added to the mixture via syringe, and the mixture stirred for another 30 min. The reaction flask was then cooled to 0C and methyl acrylate (5.0 g, 58.1 mmol) was added to the mixture by syringe followed immediately by methanol (9.40 mL, 232 mmol). The reaction was allowed to stir at room temperature overnight. The suspension was filtered through Celite and and n- hexane was added to the filtrate. A white suspension appeared which was removed by filtration and the filtrate was concentrated under vaccum. The residue was purified by Combiflash using pet ether and EtOAc (5%) as an eluant and a 40g silica column. Yield: 5.2g (42%). 1H NMR (400 MHz, CHLOROFORM- ) delta ppm 3.66 (s, 3 H) 2.43-2.48 (t, J=10 Hz, 2 H) 1.25-1.27 (s, 12 H) 1.01-1.06 (t, J=10 Hz, 2 H).

Reference： [1]Applied Organometallic Chemistry,2013,vol. 27,p. 159 - 165
[2]Patent: WO2013/150125,2013,A1 .Location in patent: Page/Page column 38
[3]Patent: EP2647640,2013,A1 .Location in patent: Paragraph 0072; 0073
[4]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3451 - 3456
[5]Bulletin of the Korean Chemical Society,2010,vol. 31,p. 551 - 552
[6]Patent: WO2014/159559,2014,A1 .Location in patent: Page/Page column 161-162
[7]Organic Letters,2008,vol. 10,p. 1795 - 1798

3
4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane [ No CAS ]
[ 292638-85-8 ]
[ 1150561-77-5 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3478 - 3481

4
[ 67-56-1 ]
[ 292638-85-8 ]
[ 73183-34-3 ]
[ 1150561-77-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3451 - 3456
[2]Chemistry - A European Journal,2012,vol. 18,p. 1121 - 1126

5
[ 1150561-77-5 ]
[ 100-39-0 ]
[ 1243540-13-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3451 - 3456
[2]Organic and Biomolecular Chemistry,2010,vol. 8,p. 3451 - 3456

6
[ 1150561-77-5 ]
[ 111-42-2 ]
[ 1290145-53-7 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 3571 - 3575

7
4,8-dimethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,6,2-dioxazaborocane [ No CAS ]
[ 292638-85-8 ]
[ 1150561-77-5 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 3997 - 4007

8
[ 1150561-77-5 ]
6-bromo-2-(4-fluorophenyl)-5-isopropoxy-N-methylbenzofuran-3-carboxamide [ No CAS ]
methyl 3-(2-(4-fluorophenyl)-5-isopropoxy-3-(methylcarbamoyl)benzofuran-6-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
46%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; caesium carbonate; In water; toluene; at 100℃;	Preparation of methyl 3-(2-(4-fluorophenyl)-5-isopropoxy-3- (methylcarbamoyl)benzofuran-6-yl)propanoate A mixture of 6-bromo-2-(4-fluorophenyl)-5-isopropoxy-N- methylbenzofuran-3-carboxamide (3.0 g, 7.38 mmol), methyl 3-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)propanoate (1.897 g, 8.86 mmol) and cesium carbonate (7.22 g, 22.15 mmol) in toluene (40 mL) and water (2 mL) at room temperature was degassed for 10 min, added with PdCl2(dppf)-CH2Cl2 adduct (0.362 g, 0.443 mmol) and then degassed again for 5 min. The resulting reaction mixture was heated at 100C for overnight. The reaction mixture was filtered through celite, the celite bed washed with EtOAc and the filtrate concentrated. The residue was purified by Combiflash using a mixture of pet ether and EtOAc as an eluent and a 120g silica gel column. The product was collected at 25% EtOAc in pet ether. Yield: 1.4g (46%). 1H NMR (400 MHz, CHLOROFORM-^) delta ppm 1.37 (d, J=6.02 Hz, 6 H) 2.62 - 2.69 (m, 2 H) 2.96 - 3.06 (m, 5 H) 3.65 - 3.69 (m, 3 H) 4.59 - 4.70 (m, 1 H) 5.76 (br. s., 1 H) 7.13 - 7.20 (m, 2 H) 7.25 - 7.30 (m, 2 H) 7.81 - 7.89 (m, 2 H). LCMS (ES+) m/z = 414.1 (M+H). Column- Acquity BEH C18 (2.1 x 50 mm) 1.7 u M phase A : 0.1% TFA in water M phase B : Acetonitrile Flow : 0.8ml/Min Time % A % 0.0 98 2 1.0 2 98 1.6 2 98 Rt min: 1.00, wavelength: 220nm

Reference： [1]Patent: WO2014/159559,2014,A1 .Location in patent: Page/Page column 162-163

9
[ 1150561-77-5 ]
3-(tert-butyldimethylsilyloxy)-4-methoxyphenyl trifluoromethanesulfonate [ No CAS ]
[ 3536-96-7 ]
methyl 5-(3-((tert-butyldimethylsilyl)oxy)-4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 3153 - 3160

10
[ 1150561-77-5 ]
[ 3536-96-7 ]
C₁₂H₂₂BO₄^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 3153 - 3160

11
[ 768-11-6 ]
[ 1150561-77-5 ]
[ 3536-96-7 ]
methyl 5-(benzo[d]thiazol-5-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 3153 - 3160

12
[ 593-60-2 ]
[ 1150561-77-5 ]
C₁₂H₂₂BO₄^(1-) [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 3153 - 3160

13
[ 1150561-77-5 ]
methyl (S)-5-phenyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pentanoate [ No CAS ]