[ CAS No. 25487-66-5 ] {[proInfo.proName]}

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2D 3D

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Quality Control of [ 25487-66-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 25487-66-5 ]

SDS Specification

Alternatived Products of [ 25487-66-5 ]

Product Details of [ 25487-66-5 ]

CAS No. :	25487-66-5	MDL No. :	MFCD00036833
Formula :	C₇H₇BO₄	Boiling Point :	-
Linear Structure Formula :	HOOCC₆H₄B(OH)₂	InChI Key :	DBVFWZMQJQMJCB-UHFFFAOYSA-N
M.W :	165.94	Pubchem ID :	2733957
Synonyms :		Chemical Name :	3-Boronobenzoic acid

Calculated chemistry of [ 25487-66-5 ] Expand+

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 :	3.0
Molar Refractivity :	43.23
TPSA :	77.76 ?2

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) :	-7.06 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	0.35
Log Po/w (WLOGP) :	-0.94
Log Po/w (MLOGP) :	-0.13
Log Po/w (SILICOS-IT) :	-1.35
Consensus Log Po/w :	-0.41

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.33
Solubility :	7.81 mg/ml ; 0.0471 mol/l
Class :	Very soluble
Log S (Ali) :	-1.55
Solubility :	4.71 mg/ml ; 0.0284 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.65
Solubility :	36.8 mg/ml ; 0.222 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.61

Safety of [ 25487-66-5 ]

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 [ 25487-66-5 ]

* 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.

Upstream synthesis route of [ 25487-66-5 ]
Downstream synthetic route of [ 25487-66-5 ]

[ 25487-66-5 ] Synthesis Path-Upstream 1~2

1
[ 1120-87-2 ]
[ 25487-66-5 ]
[ 4385-78-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate In water; acetonitrileReflux	Example 165 A3-(pyridin-4-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 4-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g 3-(pyridin-4-yl)benzoic acid. Yield: 83percent. LC-MS (ESI) m/z: 200 (M+1)⁺.

Reference： [1] Patent: US2009/197863, 2009, A1, . Location in patent: Page/Page column 76

2
[ 25487-66-5 ]
[ 19524-06-2 ]
[ 4385-78-8 ]

Reference： [1] Inorganic Chemistry, 2016, vol. 55, # 3, p. 1089 - 1095

[ 25487-66-5 ] Synthesis Path-Downstream 1~8

1
[ 626-55-1 ]
[ 25487-66-5 ]
[ 4385-77-7 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile;Reflux;	Example 163 A3-(pyridin-3-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.5 g, 9 mmol) and 3-bromopyridine (1.5 g, 9.9 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II) chloride (400 mg, 0.37 mmol) was added. The mixture was stirred under reflux overnight. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.5 g of 3-(pyridin-3-yl)benzoic acid. Yield: 83%. LC-MS (ESI) m/z: 200 (M+1)+.
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In acetonitrile; at 90℃; for 14.0h;	20 ml of 0.4 M sodium carbonate aqueous solution,3.2 g of 3-bromopyridine (21), 3.3 g of 3-carboxyphenylboronic acid and 1.15 g of tetrakis (triphenylphosphine) palladium (0) were added to 100 ml of acetonitrile,And the mixture was stirred at 90 C. for 14 hours. After completion of the reaction,Filter through Celite, add 1N dilute hydrochloric acid to the filtrate, Extracted with ethyl acetate, and washed with saturated brine.The organic layer was dried over anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure.The precipitated crystals were washed with hexane and filtered,3- (Pyridin-3-yl) benzoic acid (22)Was obtained. To the solid,50 ml of ethanol and 5 ml of concentrated sulfuric acid were added.After heating under reflux for 12 hours,Sodium bicarbonate was added to the reaction solution to quench. After distilling off ethanol under reduced pressure,An aqueous sodium hydrogen carbonate solution was addedAnd extracted three times with ethyl acetate. The organic layers were combined,Washed with saturated brine,After drying with anhydrous magnesium sulfate,The solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 4: 1)Ethyl 3- (pyridin-3-yl) benzoate(23) was obtained

Reference： [1]Synlett,2000,p. 829 - 831
[2]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 76
[3]Journal of the American Chemical Society,2013,vol. 135,p. 1853 - 1863
[4]Patent: JP5743418,2015,B2 .Location in patent: Paragraph 0142; 0143; 0144

2
[ 6967-82-4 ]
[ 25487-66-5 ]
[ 378242-13-8 ]

Yield	Reaction Conditions	Operation in experiment
37%	With sodium carbonate; In 1,2-dimethoxyethane; water;	4-Methyl-[1,1'-biphenyl]-2,3'-dicarboxylic acid To a solution of <strong>[6967-82-4]2-bromo-5-methylbenzoic acid</strong> (5.00 g, 23.3 mmol) in DME (100 mL) were added 3-carboxyphenylboronic acid (3.86 g; 23.3 mmol), a solution of Na2CO3 (9.90 g, 93 mmol) in H2O and tetrakis(triphenylphosphine)palladium. The mixture was stirred at 90 C. for 4 days. The mixture was allowed to cool to room temperature, diluted with EtOAc (50 mL), and washed with a saturated NaHCO3 solution. The aqueous layer was separated, acidified with 10 % HCl, and extracted with EtOAc (3*20 mL). The combined extracts were dried over MgSO4 and concentrated. The crude material was purified by column chromatography (9:1 hexanes/EtOAc 1% acetic acid) to afford 4-methyl-[1,1'-biphenyl]-2,3'-dicarboxylic acid (2.20 g, 37%) as a solid: H NMR (DMSO-d6) delta2.40 (s, 3H), 7.30 (m, 1H), 7.42 (m, 1H), 7.52-7.57 (m, 2H), 7.60 (s, 1H), 7.85 (s, 1H), 7.91-7.92 (m, 1H).
37%	With sodium carbonate; In 1,2-dimethoxyethane; water;	4-Methyl-[1,1'-biphenyl]-2,3'-dicarboxylic acid To a solution of <strong>[6967-82-4]2-bromo-5-methylbenzoic acid</strong> (5.00 g, 23.3 mmol) in DME (100 mL) were added 3-carboxyphenylboronic acid (3.86 g; 23.3 mmol), a solution of Na2CO3 (9.90 g, 93 mmol) in H2O and tetrakis(triphenylphosphine)palladium. The mixture was stirred at 90 C. for 4 days. The mixture was allowed to cool to rt, diluted with EtOAc (50 mL), and washed with a saturated NaHCO3 solution. The aqueous layer was separated, acidified with 10% HCl, and extracted with EtOAc (3*20 mL). The combined extracts were dried over MgSO4 and concentrated. The crude material was purified by column chromatography (9:1 hexanes/EtOAc 1% acetic acid) to afford 4-methyl-[1,1'-biphenyl]-2,3'-dicarboxylic acid (2.20 g, 37%) as a solid: 1H NMR (DMSO-d6) delta2.40 (s, 3H), 7.30 (m, 1H), 7.42 (m, 1H), 7.52-7.57 (m, 2H), 7.60 (s, 1H), 7.85 (s, 1H), 7.91-7.92 (m, 1H).

Reference： [1]Patent: US2003/36534,2003,A1
[2]Patent: US2003/100607,2003,A1

3
[ 109-04-6 ]
[ 25487-66-5 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate;bis-triphenylphosphine-palladium(II) chloride; In water; acetonitrile; at 100℃; for 24.0h;Inert atmosphere;	Example 161 A3-(pyridin-2-yl)benzoic acid; To a solution of 3-boronobenzoic acid (1.66 g, 10 mmol) and 2-bromopyridine (1.72 g, 11 mmol) in acetonitrile (40 mL) and water (40 mL), potassium carbonate (5.5 g, 40 mmol), Bis(triphenylphosphine)palladium(II)chloride (400 mg, 0.37 mmol) was added. The mixture was degassed and purged withed nitrogen. The mixture was stirred at 100 C. for 24 h. Then the hot suspension was filtered and concentrated to half of the original volume and washed with dichloromethane. The aquatic phase was adjusted to pH=3 with hydrochloric acid (1 M) and filtrated, washed with water. The residue was dried in vacuum to obtain 1.69 g of white solid of 3-(pyridin-2-yl)benzoic acid. Yield: 85%. LC-MS (ESI) m/z: 200 (M+1)+.

Reference： [1]Patent: US2009/197863,2009,A1 .Location in patent: Page/Page column 75

4
[ 931-34-0 ]
[ 25487-66-5 ]
[ 1262519-06-1 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 572 - 579

5
[ 931-34-0 ]
[ 25487-66-5 ]
3-(5-((4-oxo-2-thioxo-3-(3-(trifluoromethyl)phenyl)thiazolidin-5-ylidene)methyl)-1H-pyrrol-2-yl)benzoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 572 - 579

6
[ 25487-66-5 ]
[ 376592-93-7 ]

Reference： [1]Patent: WO2013/49605,2013,A1
[2]Patent: EP2799425,2014,A1
[3]Patent: WO2014/177517,2014,A1

7
[ 25487-66-5 ]
[ 15969-10-5 ]
[ 376592-58-4 ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; sodium carbonate; In water; at 50℃; for 3.5h;Inert atmosphere;	[0055] A mixture of Na2C03 (424 mg, 4 mmol), Pd(OAc)2 (22.4 mg, 5 mol %), PEG 2000 (7 g) and water (6 mL) was heated to 50 C under an inert atmosphere with stirring. Afterward, <strong>[15969-10-5]2-bromo-4-chloro-6-nitrophenol</strong> (Compound lb, 508 mg, 2 mmol) and 3- carboxyphenylboronic acid (Compound 3) (494 mg, 3 mmol) were added to the solution, and the mixture was heated at 50 C under an inert atmosphere. After 3.5 hrs the reaction mixture was cooled to room temperature, diluted with water (50 mL), treated with 5% aq. HC1 to adjust to pH = 2 and extracted with ethyl acetate (3x 20 mL). The combined ethyl acetate extracts were washed with water and brine (50 mL), dried over anhydrous Na2S04 and concentrated in vacuo. The crude product was obtained as a brown solid and was recrystallized from 60 % acetic acid/water to afford compound (2b) (340 mg, 58%, purity 92%, HPLC Method B).

Reference： [1]Patent: WO2013/49605,2013,A1 .Location in patent: Paragraph 0055

8
[ 106-38-7 ]
[ 25487-66-5 ]
[ 147404-69-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In ethanol; water; toluene; at 100.0℃; for 4h;	186 mg 3-carboxyphenylboronic acid (1.05 mmol), 126 μ 4-bromotoluene (1.0 mmol), 417 mg K2CO3 (3.0 mmol) and 23 mg palladium(0) tetrakis(triphenylphosphine) (0.02 mmol) were given in a screw-cap reactor, 8.5 mL of a 8:8:1 toluene/EtOH/H2O mixture were added, the reactor was closed tightly and heated to 100C under stirring. After 4 h the mixture was cooled to room temperature, diluted with AcOEt (10 mL) and extracted with 2 % NaHCO3 (4x10 mL). The pooled basic extracts were acidified to pH 3 by dropwise addition of 6 N HCl under stirring and extracted with AcOEt (3x12 mL), the pooled organic extracts were washed H2O (10 mL) and brine (10 mL), then dried over Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude product was purified by preparative HPLC, yielding 128 mg 3-(4'-tolyl)-benzoic acid (60 % yield).

Reference： [1]Patent: WO2017/12890,2017,A1 .Location in patent: Page/Page column 25-26

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Technical Information

? Arndt-Eistert Homologation ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? 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 ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Ugi Reaction ? Vilsmeier-Haack Reaction

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H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 25487-66-5 ] {[proInfo.proName]}

Quality Control of [ 25487-66-5 ]

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Calculated chemistry of [ 25487-66-5 ] Expand+

Physicochemical Properties

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Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 25487-66-5 ]

[ 25487-66-5 ] Synthesis Path-Upstream 1~2

[ 25487-66-5 ] Synthesis Path-Downstream 1~8

Technical Information

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Organoboron

Aryls

Carboxylic Acids

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[ 25487-66-5 ]