[ CAS No. 269409-73-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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2D 3D

Structure of 269409-73-6 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 269409-73-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 269409-73-6 ]

SDS Specification

Alternatived Products of [ 269409-73-6 ]

Product Details of [ 269409-73-6 ]

CAS No. :	269409-73-6	MDL No. :	MFCD03411930
Formula :	C₁₃H₁₇BO₄	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	OPWAPCOSDAFWFB-UHFFFAOYSA-N
M.W :	248.08	Pubchem ID :	2734653
Synonyms :		Chemical Name :	3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

Calculated chemistry of [ 269409-73-6 ] 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 :	2.87

Safety of [ 269409-73-6 ]

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

Application In Synthesis of [ 269409-73-6 ]

* 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 [ 269409-73-6 ]

[ 269409-73-6 ] Synthesis Path-Downstream 1~4

1
[ 269409-73-6 ]
[ 6274-22-2 ]
[ 1415695-08-7 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; HATU; In N,N-dimethyl-formamide; at 20℃; for 24h;	A mixture of 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoic acid (0.8 g, 3.22 mmol), <strong>[6274-22-2]4-amino-N-methylbenzamide</strong> (0.58 g, 3.86 mmol), HATU (1.47 g, 3.8 mmol) and DIEA (1 g, 7.7 mmol) in DMF (10 mL) was stirred at room temperature for 24 h. The solvent was evaporated at 70C under reduced pressure to give a crude product. It was filtered through a plug of silica gel and the filter cake washed with ethyl acetate / petroleum ether (1: 1, v/v). The combined filtrates were concentrated to give crude N-(4- (methylcarbamoyl)phenyl)-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzamide (0.56 g, 45.9 %) as a white solid that was used directly without further purification.LC/MS: 381.1 [M+H]+.

Reference： [1]Patent: WO2012/163724,2012,A1 .Location in patent: Page/Page column 47

2
[ 269409-73-6 ]
[ 49851-36-7 ]
methyl 2-(2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamido)phenyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		TEA (1.685 mL, 12.09 mmol) was added to a mixture of 3-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)benzoic acid (CAS 269409-73-6) (1 g, 4.03 mmol) and HATU (1.686 g, 4.43 mmol) in DMF (4.5 mL). After 30 min, <strong>[49851-36-7]methyl 2-(2-aminophenyl)acetate hydrochloride</strong> (CAS 49851-36-7) (0.666 g, 4.03 mmol) was added and the resulting mixture was stirred at room temperature overnight. The reaction was diluted with a 4:1 EtOAc/heptanes mixture and water. The aqueous phase was extracted with 4:1 EtOAc/heptanes. The combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (heptane/EtOAc with 10% MeOH, 100:0 to 0:100) to give the title compound. MS (ESI+) m/z 396.4 (M+H).

Reference： [1]Patent: WO2015/9977,2015,A1 .Location in patent: Page/Page column 131

3
[ 109-04-6 ]
[ 269409-73-6 ]
[ 4467-07-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In water; N,N-dimethyl-formamide; at 110℃;Inert atmosphere;	To a degassed souton of DMF:H20 (10:1 raUo) (0.3 M), under an atmosphere of nitrogen, was added the pnaco ester (1 mmo), 2-bromopyrdne or 2-choropyrmdne (1 .5 eq.), and Cs2CO3 (4.4 eq.). The whoe mxture was degassed once agan and then Pd(PPh3)4 (5mo%) was added. The resutng souton was heated to 110C overnght. The sovent was removed in vacuo to give a dark gummy residue, which was taken up nto EtOAc and H20, then acdfied with 2 M HC to pH 2. The organic ayer was separated and the aqueous ayer was further extracted with EtOAc (2x). The combined organic ayers were dried over MgSO4 and concentrated in vacuo to gve a back ofly residue. The residue was dry oaded ontosWca ge in vacuo then purfied by flash coumn chromatography, eutng with 10-30% EtOAc/petroeum benzne and 1% acetic acid to afford the tWe compound.The foHowng compounds were made by Suzuk CoupUng F:P1B1Off white soUd (75% yed). 1H NMR (400 MHz,DMSO) 6 8.71 8.68 (m, 1 H), 8.67 (s, 1 H), 8.29 (d,J = 7.8 Hz, 1 H), 8.01 (t, J = 8.4 Hz, 2H), 7.91 (td, J =7.8, 1.8 Hz, 1 H), 7.61 (t, J = 7.7 Hz, 1 H), 7.42 7.37(m, 1H). LCMS B rt3.17, m/z200.1 [M + H].

Reference： [1]Patent: WO2016/198507,2016,A1 .Location in patent: Page/Page column 40; 50

4
[ 17321-93-6 ]
[ 269409-73-6 ]
C₁₂H₁₁N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; In 1,4-dioxane; water; at 95℃;Inert atmosphere;	General procedure: The halo aryl (1.0 equiv) was dissolved in a mixture of water:dioxane (1:1). The boronic acid or ester(1.5 equiv) and potassium phosphate (5.0 equiv) were added. The solution was degassed byvacuum/argon cycles (10 times) before addition of PdCl2(PPh3)2 (10 molpercent) and further degassed (5times). The resulting mixture was stirred at 95 °C under argon atmosphere for 16-20 hours. Thereaction mixture was filtered through Celite and diluted with water (approx. 30 mL) before washingwith chloroform (3 x 30 mL). If not stated otherwise, the aqueous phase was concentrated underreduced pressure and applied to a C18 precolumn before purification on a 10g or 60 g C18 column witha gradient of acetonitrile in water (10-100percent) to yield the desired product.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 634 - 648

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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

Historical Records

Related Functional Groups of
[ 269409-73-6 ]

Organoboron

[ 180516-87-4 ]

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Aryls

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Carboxylic Acids

[ 180516-87-4 ]

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

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P220	Keep/Store away from clothing/combustible materials.
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P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
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P342	If experiencing respiratory symptoms:
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P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
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P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
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Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
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H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
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H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 269409-73-6 ] {[proInfo.proName]}

Quality Control of [ 269409-73-6 ]

Related Doc. of [ 269409-73-6 ]

Product Details of [ 269409-73-6 ]

Calculated chemistry of [ 269409-73-6 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 269409-73-6 ]

Application In Synthesis of [ 269409-73-6 ]

[ 269409-73-6 ] Synthesis Path-Downstream 1~4

Technical Information

Related Functional Groups of [ 269409-73-6 ]

Organoboron

Aryls

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 269409-73-6 ]