[ CAS No. 180516-87-4 ] {[proInfo.proName]}

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2D 3D

Structure of 180516-87-4 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 180516-87-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 180516-87-4 ]

SDS Specification

Alternatived Products of [ 180516-87-4 ]

Product Details of [ 180516-87-4 ]

CAS No. :	180516-87-4	MDL No. :	MFCD01863710
Formula :	C₁₃H₁₇BO₄	Boiling Point :	-
Linear Structure Formula :	HOCOC₆H₄B(OC(CH₃)₂)₂	InChI Key :	IYDKBQIEOBXLTP-UHFFFAOYSA-N
M.W :	248.08	Pubchem ID :	2734621
Synonyms :		Chemical Name :	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Calculated chemistry of [ 180516-87-4 ] Expand+

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.46
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	69.88
TPSA :	55.76 ?2

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) :	-6.09 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.43
Log Po/w (WLOGP) :	1.68
Log Po/w (MLOGP) :	1.27
Log Po/w (SILICOS-IT) :	1.25
Consensus Log Po/w :	1.33

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-3.02
Solubility :	0.235 mg/ml ; 0.000947 mol/l
Class :	Soluble
Log S (Ali) :	-3.24
Solubility :	0.142 mg/ml ; 0.00057 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.38
Solubility :	0.104 mg/ml ; 0.000421 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.76

Safety of [ 180516-87-4 ]

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 [ 180516-87-4 ]

* 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 [ 180516-87-4 ]
Downstream synthetic route of [ 180516-87-4 ]

[ 180516-87-4 ] Synthesis Path-Upstream 1~1

1
[ 180516-87-4 ]
[ 179117-44-3 ]

Yield	Reaction Conditions	Operation in experiment
45%	With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃; for 3 h;	Step 1 4-(4,4,5,5-Metramethyl-1,3,2-dioxaborolan-2-yl)benzamide Procedure To a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (200 mg, 0.746 mmol), EDCI (214 mg, 1.12 mmol), HOBt (151 mg, 1.12 mmol) and Et3N (151 mg, 1.49 mmol) in DCM (20 mL) was bubbled ammonia until saturation. The mixture was stirred at room temperature for 3 h, then was filtered and the filtrate was concentrated to give residue which was purified by column chromatography (DCM:MeOH=50:1) to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (90 mg, 45percent) as a yellow solid. LC-MS: 248 [M+H]⁺, t_R=1.421 min.

Reference： [1] Patent: US2012/252777, 2012, A1, . Location in patent: Page/Page column 96
[2] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 13, p. 4036 - 4040

[ 180516-87-4 ] Synthesis Path-Downstream 1~10

1
[ 19524-06-2 ]
[ 180516-87-4 ]
[ 4385-76-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine)palladium (0); In N-methyl-acetamide;	a 4-(4-pyridinyl)benzoic acid 4-Bromopyridine hydrochloride (0.4 g, 2 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (0.5 g, 2 mmol), and tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.04 mmol) in dimethylformamide (15 mL) was treated with 2M potassium carbonate (2 mL) and the mixture was heated to 80° C. for 16 h. The mixture was concentrated in vacuo and the residue was diluted with water to afford a solid which was filtered to afford the title compound (0.26 g).

Reference： [1]Patent: US6399656,2002,B1

2
[ 29022-11-5 ]
[ 64709-55-3 ]
[ 180516-87-4 ]
[ 147290-11-7 ]
[ 1609670-33-8 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 5854 - 5857

3
[ 64709-55-3 ]
[ 143824-78-6 ]
[ 180516-87-4 ]
[ 147290-11-7 ]
[ 1609670-32-7 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 5854 - 5857
[2]New Journal of Chemistry,2017,vol. 41,p. 2593 - 2603

4
[ 180516-87-4 ]
[ 59878-57-8 ]
(4-cyclopropylcarbonylpiperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61.4%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; water; N,N-dimethyl-formamide; at 20℃;	At room temperature will 4-carboxyphenyl boronic acid pinacol ester (3g, 12.10mmol) was dissolved in dichloromethane (27ml, 0.422mol) And N,N-dimethylformamide (9ml, 0.116mol) was added 1-cyclopropyl-methylpiperazine (2.3g, 14.9mmol), And successively added 1-ethyl - (3-dimethylaminopropyl)carbodiimide hydrochloride (2.79g, 14.4mmol), N- hydroxybenzotriazole (1.98g, 12.9mmol), triethylamine (2.5ml, 17.99mmol), The reaction was stirred at room temperature until TLC monitoring Completion of the reaction starting material, the reaction solution was added 30ml of water, stirred for 30 minutes, (100ml * 3) and extracted with dichloromethane, and then With a saturated sodium chloride solution (100ml * 2) washing the organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure, to give: (4- Cyclopropylcarbonyl - piperazin-1-yl) - [4- (4,4,5,5-tetramethyl - [1,3,2] dioxaborolan-2-yl) - phenyl ] - methanone (3.5g, White solid), 61.4% yield, used in the next reaction.

Reference： [1]Patent: CN103087077,2016,B .Location in patent: Paragraph 0083-0085

5
[ 64709-55-3 ]
[ 96402-49-2 ]
[ 180516-87-4 ]
[ 147290-11-7 ]
C₄₃H₃₉BN₄O₆ [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 2593 - 2603

6
[ 64709-55-3 ]
[ 35661-40-6 ]
[ 180516-87-4 ]
[ 147290-11-7 ]
C₃₉H₃₇BN₄O₆ [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 2593 - 2603

7
[ 64709-55-3 ]
[ 109425-51-6 ]
[ 180516-87-4 ]
[ 147290-11-7 ]
C₃₆H₃₅BN₆O₆ [ No CAS ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 2593 - 2603

8
[ 180516-87-4 ]
[ 1420477-60-6 ]

Reference： [1]Patent: CN108250186,2018,A
[2]Patent: CN108250186,2018,A

9
[ 854601-60-8 ]
[ 180516-87-4 ]
1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-5,8,11,14,17,20,23,26,29,32,35-undecaoxaazahexatriacontan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃;	4-(4,4,5,5-Tetramethyl-l ,3,2-dioxaborolan-2-yl)benzoic acid (100 mg) and2,5,8,1 l,14,17,20,23,26,29,32-undecaoxatetratriacontan-34-amine (229 mg) were dissolved in dichloromethane (2 mL). N1-((Ethylimino)methylene)-N3^V3-dimethylpropane-l,3-diaminehydrochloride (162 mg) and NN-dimethylpyridin-4-amine (73.9 mg) were added. The solution was mixed at room temperature overnight. The solution was concentrated under vacuum and purified by flash column chromatography using a gradient of 0-20% methanol in dichloromethane. The solvent was removed under vacuum to yield the title compound. 'H NMR (500 MHz, dimethylsulfoxide-cfe) δ ppm 8.56 (t, IH), 7.85 (d, 2H), 7.74 (d, 2H), 3.56-3.46 (m, 44H), 3.24 (s, 3H), 1.31 (s, 12H). MS (ESI) m/z 763.0 (M+NH4)+.

Reference： [1]Patent: WO2019/35927,2019,A1 .Location in patent: Paragraph 00457

10
[ 180516-87-4 ]
[ 568577-88-8 ]

Reference： [1]Journal of the American Chemical Society,2020,vol. 142,p. 5918 - 5923

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Isomers

Technical Information

? Acyl Group Substitution ? Arndt-Eistert Homologation ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Friedel-Crafts Reaction ? Hunsdiecker-Borodin Reaction ? Hydrogenolysis of Benzyl Ether ? Passerini Reaction ? Preparation of Alkylbenzene ? Preparation of Amines ? Preparation of Carboxylic Acids ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Carboxylic Acids ? Reactions with Organometallic Reagents ? Schmidt Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction ? Vilsmeier-Haack Reaction

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[ CAS No. 180516-87-4 ] {[proInfo.proName]}

Quality Control of [ 180516-87-4 ]

Related Doc. of [ 180516-87-4 ]

Product Details of [ 180516-87-4 ]

Calculated chemistry of [ 180516-87-4 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 180516-87-4 ]

Application In Synthesis of [ 180516-87-4 ]

[ 180516-87-4 ] Synthesis Path-Upstream 1~1

[ 180516-87-4 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 180516-87-4 ]

Organoboron

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 180516-87-4 ]