[ CAS No. 929626-18-6 ]

Name: 929626-18-6|(3-(Methoxycarbonyl)-5-methylphenyl)boronic acid|98%
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Quality Control of [ 929626-18-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 929626-18-6 ]

SDS

Alternatived Products of [ 929626-18-6 ]

Product Details of [ 929626-18-6 ]

CAS No. :	929626-18-6	MDL No. :	MFCD09751432
Formula :	C₉H₁₁BO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	193.99 g/mol	Pubchem ID :	-
Synonyms :

Calculated chemistry of of [ 929626-18-6 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	52.51
TPSA :	66.76 Å²

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) :	-6.74 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.04
Log Po/w (WLOGP) :	-0.54
Log Po/w (MLOGP) :	0.52
Log Po/w (SILICOS-IT) :	-0.39
Consensus Log Po/w :	0.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.82
Solubility :	2.96 mg/ml ; 0.0152 mol/l
Class :	Very soluble
Log S (Ali) :	-2.03
Solubility :	1.8 mg/ml ; 0.00928 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.75
Solubility :	3.41 mg/ml ; 0.0176 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 929626-18-6 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 929626-18-6 ]

* 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 [ 929626-18-6 ]

[ 929626-18-6 ] Synthesis Path-Downstream 1~7

1
[ 929626-17-5 ]
[ 929626-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With sodium periodate In tetrahydrofuran; water for 0.25h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 4h;
466 mg	Stage #1: methyl 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate With sodium periodate; water In tetrahydrofuran at 23℃; for 8h; Inert atmosphere; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 1h; Inert atmosphere;

Reference： [1]Murphy, Jaclyn M.; Tzschucke, C. Christoph; Hartwig, John F. [Organic Letters, 2007, vol. 9, # 5, p. 757 - 760]
[2]Furuya, Takeru; Ritter, Toblas [Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863]

2
[ 99-36-5 ]
[ 929626-18-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-methoxycarbonyl-3-methylbenzene With pinacol borane; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine In cyclohexane at 80℃; for 24h; Stage #2: With sodium periodate In tetrahydrofuran; water for 0.5h; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 20℃; for 17h;
	Multi-step reaction with 2 steps 1.1: 4,4'-di-tert-butyl-2,2'-bipyridine / [Ir(COD)(OMe)]2 / tetrahydrofuran / 16 h / 80 °C 2.1: sodium periodate / tetrahydrofuran; H₂O / 0.25 h 2.2: HCl / H₂O; tetrahydrofuran / 4 h

Reference： [1]Tzschucke, C. Christoph; Murphy, Jaclyn M.; Hartwig, John F. [Organic Letters, 2007, vol. 9, # 5, p. 761 - 764]
[2]Murphy, Jaclyn M.; Tzschucke, C. Christoph; Hartwig, John F. [Organic Letters, 2007, vol. 9, # 5, p. 757 - 760]

3
[ 929626-18-6 ]
[ 108-69-0 ]
N-(3,5-dimethylphenyl)-3-methoxycarbonyl-5-methylphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With 2,6-dimethylpyridine; air; 1-decanoic acid In toluene at 20℃; for 24h;

Reference： [1]Tzschucke, C. Christoph; Murphy, Jaclyn M.; Hartwig, John F. [Organic Letters, 2007, vol. 9, # 5, p. 761 - 764]

4
[ 929626-18-6 ]
[ 660416-38-6 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: (3-methoxycarbonyl-5-methyl-phenyl)boronic acid With sodium hydroxide In methanol at 23℃; for 0.25h; Inert atmosphere; Stage #2: With silver trifluoromethanesulfonate In methanol at 0℃; for 0.5h; Inert atmosphere; Stage #3: With Selectfluor In acetone at 23℃; for 1h; Inert atmosphere; Molecular sieve; regiospecific reaction;

Reference： [1]Furuya, Takeru; Ritter, Toblas [Organic Letters, 2009, vol. 11, # 13, p. 2860 - 2863]

5
[ 99-36-5 ]
[ 73183-34-3 ]
[ 929626-18-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1-methoxycarbonyl-3-methylbenzene; bis(pinacol)diborane In tetrahydrofuran at 23 - 80℃; Stage #2: With sodium periodate; water In tetrahydrofuran at 23℃; for 8h; Stage #3: With hydrogenchloride In tetrahydrofuran; water for 1h;	62 Example 62. 3-Methoxycarbonyl-5-methylphenyl boronic acid (S52)To m-toluic acid methyl ester (451 mg, 3.00 mmol, 1.00 equiv) in THF (6.0 mL) at 23 0C was added [Ir(COD)(OMe)]2 (10 mg, 0.015 mmol, 0.50 mol%), dtbpy (8.0 mg, 0.030 mmol, 1.0 mol%) and bis(pinacolato)diborone (610 mg, 2.40 mmol, 0.800 equiv). After stirring for 24 hr at 80 0C, the reaction mixture was added to H2O (6.0 mL) and NaIO4 (3.21 g, 15.0 mmol, 5.00 equiv). After stirring for 8.0 hr at 23 0C, the reaction mixture was added to IN HCl aq (10 mL) and was further stirred for 1.0 hr. To the reaction mixture was added EtOAc (20 mL) and the phases were separated. The aqueous phase was extracted with EtOAc (2 x 20 mL). The combined organic phases are washed with brine (20 mL) and dried (Na2SO4). The filtrate was concentrated in vacuo and the residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 7:3 (v/v) to afford 466 mg of the title compound as a colorless solid (80% yield). R/ = 0.15 (hexanes/EtOAc 7:3 (v/v)). NMR Spectroscopy: 1U NMR (500 MHz,OMSO-d6, 23 0C, δ): 8.21 (s, IH), 8.19 (s, 2H), 7.84 (s, IH), 7.79 (s, IH), 3.83 (s, 3H), 2.35 (s, 3H). 13C NMR (125 MHz, OMSO-d6, 23 0C, δ): 166.71, 139.65, 136.97, 134.70 (br), 132.24, 131.14, 128.83, 51.99, 20.82.

Reference： [1]Current Patent Assignee: HARVARD UNIVERSITY - WO2010/59943, 2010, A2 Location in patent: Page/Page column 87

6
[ 929626-18-6 ]
[ 96898-10-1 ]
[ 1261650-22-9 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: (3-methoxycarbonyl-5-methyl-phenyl)boronic acid With sodium hydroxide In methanol at 23℃; for 0.25h; Inert atmosphere; Stage #2: With silver(I) hexafluorophosphate In methanol at 0℃; for 0.5h; Inert atmosphere; Stage #3: tris(dimethylamino)sulfonium trifluoromethoxide Further stages;

Reference： [1]Huang, Chenghong; Liang, Theresa; Harada, Shinji; Lee, Eunsung; Ritter, Tobias [Journal of the American Chemical Society, 2011, vol. 133, # 34, p. 13308 - 13310]

7
[ 929626-18-6 ]
C₂₅H₃₉BrN₆O₆ [ No CAS ]
C₃₄H₄₈N₆O₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; XPhos In 1,4-dioxane; water at 90℃; for 16h; Inert atmosphere;	Preparation of intermediate 12 A mixture of 1,4-dioxane and water (3:1, 15 ml) was degassed by bubbling nitrogen gas through the mixture. Intermediate 11(3.00 g, 5.00 mmol) and (3-methoxycarbonyl-5-methyl- phenyl)boronic acid (1 .79 g, 6.50 mmol) were dissolved. 2-Dicyclohexylphosphino-2’,4’,6’- triisopropylbiphenyl (Xphos) (143 mg, 0.30 mmol), tetrakis(triphenylphosphine)palladium(0) (116 mg, 0.10 mmol), and potassium phosphate tribasic (5.03 g, Seq.) were added and themixture was stirred under nitrogen gas at 90°C for 16 hours. The reaction mixture was cooled, passed over celite and the solvent was removed under reduced pressure. The residue was purified by flash column chromatography over silica gel using dichloromethane and methanol as eluents (gradient elution from 0% to 10% methanol). The product fractions were collected and the solvent was removed under reduced pressure.Yield: 3.00 g of intermediate 12 (90%)LCMS method 1: MH = 569 (MW-Boc), RT = 1.419 mm

Reference： [1]Current Patent Assignee: CRÉDIT INDUSTRIEL ET COMMERCIAL - CIC; BANQUE DE VIZILLE - WO2015/136073, 2015, A1 Location in patent: Page/Page column 108

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P337 + P313	IF eye irritation persists: Get medical advice/attention.
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
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H271	May cause fire or explosion; strong oxidizer
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H302	Harmful if swallowed
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H311	Toxic in contact with skin
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
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H319	Causes serious eye irritation
H320	Causes eye irritation
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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
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H336	May cause drowsiness or dizziness
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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

[ CAS No. 929626-18-6 ]

Quality Control of [ 929626-18-6 ]

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Product Details of [ 929626-18-6 ]

Calculated chemistry of of [ 929626-18-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 929626-18-6 ]

Application In Synthesis of [ 929626-18-6 ]

[ 929626-18-6 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 929626-18-6 ]

Organoboron

Aryls

Esters

Organoboron

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 929626-18-6 ]