[ CAS No. 890839-11-9 ] {[proInfo.proName]}

Name: 890839-11-9|Methyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)propanoate|97%
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SKU: A436570
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Quality Control of [ 890839-11-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 890839-11-9 ]

SDS Specification

Alternatived Products of [ 890839-11-9 ]

Product Details of [ 890839-11-9 ]

CAS No. :	890839-11-9	MDL No. :	MFCD28128120
Formula :	C₁₆H₂₃BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	FJPXZQYGTLPYRT-UHFFFAOYSA-N
M.W :	290.16	Pubchem ID :	57871071
Synonyms :

Calculated chemistry of [ 890839-11-9 ]

Physicochemical Properties

Num. heavy atoms :	21
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.56
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	83.59
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) :	-5.75 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	3.27
Log Po/w (WLOGP) :	2.26
Log Po/w (MLOGP) :	1.78
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	1.94

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.65
Solubility :	0.0655 mg/ml ; 0.000226 mol/l
Class :	Soluble
Log S (Ali) :	-3.88
Solubility :	0.0379 mg/ml ; 0.00013 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.5
Solubility :	0.00913 mg/ml ; 0.0000315 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.53

Safety of [ 890839-11-9 ]

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

Application In Synthesis of [ 890839-11-9 ]

* 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 [ 890839-11-9 ]
Downstream synthetic route of [ 890839-11-9 ]

[ 890839-11-9 ] Synthesis Path-Upstream 1~6

1
[ 74-88-4 ]
[ 890839-11-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 0.333333 h; Stage #2: at 0 - 20℃; for 1 h;	b) Methyl 2-f4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-vDphenvπpropanoate; To a solution of methyl [4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]acetate (1.04 g, 3.78 mmol) in THF (6 mL) was added LDA (3.5 mL, 1.5M in THF) dropwise at -78⁰C under argon. After stirring for 20 min, the reaction mixture was warmed up to 0 ⁰C, MeI ( 3.22 g, 22.6 mmol) was added and the mixture was stirred for 1 h at room temperature. The reaction was quenched by adding HCI (2M solution) until pH~2. The mixture was extracted with EtOAc, concentrated and purified via combiflash to give the product as a white solid (0.77 g, 70percent). ¹H-NMR (CDCI₃) δ : 1.354 (12H, s), 1.517 (3H, d, J=7.2 Hz ), 3.667 (3H, s), 3.750 (1H₁ m), 7.323 (2H,d, J=7.2 Hz), 7.796 (2H, d, J=7.2 Hz).

Reference： [1] Patent: WO2006/63167, 2006, A1, . Location in patent: Page/Page column 23; 24

2
[ 83636-46-8 ]
[ 73183-34-3 ]
[ 890839-11-9 ]

Reference： [1] Patent: EP1054857, 2003, B1, . Location in patent: Page/Page column 19-20

3
[ 39718-97-3 ]
[ 73183-34-3 ]
[ 890839-11-9 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803

4
[ 2945-08-6 ]
[ 890839-11-9 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803

5
[ 50415-69-5 ]
[ 890839-11-9 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803

6
[ 104-03-0 ]
[ 890839-11-9 ]

Reference： [1] Green Chemistry, 2017, vol. 19, # 20, p. 4798 - 4803

[ 890839-11-9 ] Synthesis Path-Downstream 1~31

1
[ 890839-11-9 ]
[ 148322-13-8 ]
[ 236747-82-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In water; dimethyl sulfoxide; at 85℃; for 4h;	A suspension of diboron dipinacolate (205 mg, 0.81 mmol), [1,2-bis(diphenylphosphino)-ethane]dichloropalladium(II) (27 mg, 47 mumol) and KOAc (217 mg, 2.2 mmol) in DMSO (2 mL) was degassed by bubbling N2 for 10 min. Then methyl 2-(4-bromophenyl)propanoate (112 muL, 0.6 mmol) was added and the resulting mixture was heated at 85 C for 2 hours and allowed to cool to room temperature. To this mixture was added a 2.0M aqueous solution of Na2CO3 (1.5 mL, 3 mmol) and a solution of 16a (203 mg, 0.55 mmol) in DMSO (2 mL). The mixture was degassed by bubbling with N2 for 10 min., [1,1'-bis(diphenylphosphino) ferrocene]-dichloropalladium(II)·CH2Cl2 (19 mg, 23 mumol) was added and the reaction was heated at 85 C for 2 hours. Then another portion of palladium catalyst was added (12 mg, 15 mumol) and the reaction was heated for another 2 hours. The reaction was allowed to cool to room temperature, diluted with EtOAc, washed with water, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography (15 to 20% EtOAc/hexanes) to give 37 mg of the title compound as a yellow gum. 1H NMR (d6-acetone) delta 1.45 (3H, d), 2.55 (3H, s), 3.62 (3H, s), 3.78 (1H, q), 7.04 (3H, m), 7.17 (2H, m), 7.34 (2H, d), 7.48 (2H, m), 7.58 (2H, d), 7.67 (1H, s), 10.7 (1H, b).

Reference： [1]Patent: EP1054857,2003,B1 .Location in patent: Page/Page column 19-20

2
[ 74-88-4 ]
[ 890839-11-9 ]

Yield	Reaction Conditions	Operation in experiment
70%		b) Methyl 2-f4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-vDphenv?propanoate; To a solution of methyl [4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenyl]acetate (1.04 g, 3.78 mmol) in THF (6 mL) was added LDA (3.5 mL, 1.5M in THF) dropwise at -780C under argon. After stirring for 20 min, the reaction mixture was warmed up to 0 0C, MeI ( 3.22 g, 22.6 mmol) was added and the mixture was stirred for 1 h at room temperature. The reaction was quenched by adding HCI (2M solution) until pH~2. The mixture was extracted with EtOAc, concentrated and purified via combiflash to give the product as a white solid (0.77 g, 70%). 1H-NMR (CDCI3) delta : 1.354 (12H, s), 1.517 (3H, d, J=7.2 Hz ), 3.667 (3H, s), 3.750 (1H1 m), 7.323 (2H,d, J=7.2 Hz), 7.796 (2H, d, J=7.2 Hz).

Reference： [1]Patent: WO2006/63167,2006,A1 .Location in patent: Page/Page column 23; 24

3
[ 83636-46-8 ]
[ 73183-34-3 ]
[ 890839-11-9 ]

Yield	Reaction Conditions	Operation in experiment
92%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; for 6h;Inert atmosphere; Reflux;	A mixture of Methyl 2-(4-bromophenyl)propionate (38) (5g, 20.56 mmol), potassium acetate (4.04 g, 41.11 mmol), Bis(pinacolato)diboron (10.45 g, 41.13 mmol) and [1,10-bis(diphenylphosphino)ferrocene]dichloropalladium (II) (0.84 g, 1.03 mmol) in 1,4-dioxane (100 mL) was refluxed for 6 h under nitrogen atmosphere. The reaction mixture was cooled to 60 C and concentrated under reduced pressure. Water (50 mL) and ethyl acetate (50 mL) were charged, stirred for 30 min and filtered through celite. Organic layer was separated, dried over sodium sulfate and concentrated. The residue was purified using column chromatography (silica gel, 3-5 % ethyl acetate in hexane) to afford Methyl 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaboralan-2-yl)phenyl]propionate (44) (5.5 g, 92 %) as a colourless syrup: 1H NMR (400 MHz, CDCl3) delta 7.78 (d, J = 7.6 Hz, 2H), 7.32 (d, J = 8.4 Hz, 2H), 3.73 (q, J = 6.8 Hz, 1H), 3.63 (s, 3H), 1.50 (d, J = 7.2 Hz, 3H), 1.32 (s, 12H); 13C NMR (100 MHz, CDCl3) delta 174.72, 143.73, 135.18, 134.97, 126.89, 124.98, 83.76, 52.02, 45.61, 24.85, 18.50; IR (KBr) numax 2980.90, 1740.69 cm-1; MS: m/z 291.1 (M + H)+.
		A suspension of diboron dipinacolate (205 mg, 0.81 mmol), [1,2-bis(diphenylphosphino)-ethane]dichloropalladium(II) (27 mg, 47 mumol) and KOAc (217 mg, 2.2 mmol) in DMSO (2 mL) was degassed by bubbling N2 for 10 min. Then methyl 2-(4-bromophenyl)propanoate (112 muL, 0.6 mmol) was added and the resulting mixture was heated at 85 C for 2 hours and allowed to cool to room temperature. To this mixture was added a 2.0M aqueous solution of Na2CO3 (1.5 mL, 3 mmol) and a solution of 16a (203 mg, 0.55 mmol) in DMSO (2 mL). The mixture was degassed by bubbling with N2 for 10 min., [1,1'-bis(diphenylphosphino) ferrocene]-dichloropalladium(II)·CH2Cl2 (19 mg, 23 mumol) was added and the reaction was heated at 85 C for 2 hours. Then another portion of palladium catalyst was added (12 mg, 15 mumol) and the reaction was heated for another 2 hours. The reaction was allowed to cool to room temperature, diluted with EtOAc, washed with water, dried over MgSO4 and concentrated. The crude product was purified by flash chromatography (15 to 20% EtOAc/hexanes) to give 37 mg of the title compound as a yellow gum. 1H NMR (d6-acetone) delta 1.45 (3H, d), 2.55 (3H, s), 3.62 (3H, s), 3.78 (1H, q), 7.04 (3H, m), 7.17 (2H, m), 7.34 (2H, d), 7.48 (2H, m), 7.58 (2H, d), 7.67 (1H, s), 10.7 (1H, b).

Reference： [1]Tetrahedron,2019,vol. 75,p. 874 - 887
[2]Patent: EP1054857,2003,B1 .Location in patent: Page/Page column 19-20

4
[ 2945-08-6 ]
[ 890839-11-9 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4798 - 4803

5
[ 50415-69-5 ]
[ 890839-11-9 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4798 - 4803

6
[ 39718-97-3 ]
[ 73183-34-3 ]
[ 890839-11-9 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4798 - 4803

7
[ 104-03-0 ]
[ 890839-11-9 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4798 - 4803

8
[ 890839-11-9 ]
methyl 2-(2'-azido-5'-chloro-[1,1'-biphenyl]-4-yl)propanoate [ No CAS ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4798 - 4803

9
[ 890839-11-9 ]
[ 52263-88-4 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 4798 - 4803
[2]Tetrahedron,2019,vol. 75,p. 874 - 887

10
[ 890839-11-9 ]
[ 63069-48-7 ]
methyl 2-(2'-amino-5'-chloro-[1,1'-biphenyl]-4-yl)propanoate [ No CAS ]