[ CAS No. 909187-39-9 ]

Name: 909187-39-9|(2-Methoxy-3-methylphenyl)boronic acid|98%
Brand: Ambeed
SKU: A541572
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Quality Control of [ 909187-39-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 909187-39-9 ]

SDS Specification

Alternatived Products of [ 909187-39-9 ]

Product Details of [ 909187-39-9 ]

CAS No. :	909187-39-9	MDL No. :	MFCD06801731
Formula :	C₈H₁₁BO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RGEFKQADFIJDCW-UHFFFAOYSA-N
M.W :	165.98	Pubchem ID :	23005356
Synonyms :

Calculated chemistry of [ 909187-39-9 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	2
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	47.73
TPSA :	49.69 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) :	-6.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.16
Log Po/w (WLOGP) :	-0.32
Log Po/w (MLOGP) :	0.33
Log Po/w (SILICOS-IT) :	-0.3
Consensus Log Po/w :	0.17

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.84
Solubility :	2.41 mg/ml ; 0.0145 mol/l
Class :	Very soluble
Log S (Ali) :	-1.8
Solubility :	2.64 mg/ml ; 0.0159 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.79
Solubility :	2.66 mg/ml ; 0.016 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.64

Safety of [ 909187-39-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P330-P363-P501	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 909187-39-9 ]

* 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.

Downstream synthetic route of [ 909187-39-9 ]

[ 909187-39-9 ] Synthesis Path-Downstream 1~8

1
[ 142010-72-8 ]
[ 909187-39-9 ]
2,2'-Bis-methoxymethoxy-3-(2-methoxy-3-methyl-phenyl)-[1,1']binaphthalenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With barium dihydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In 1,2-dimethoxyethane; water at 80℃; for 12h;

Reference： [1]Ishihara, Kazuaki; Kurihara, Hideki; Matsumoto, Masayuki; Yamamoto, Hisashi [Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6920 - 6930]

2
[ 909187-39-9 ]
[ 175476-73-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Ba(OH)2*8H₂O, Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 12 h / 80 °C 2: 4M aq. HCl / tetrahydrofuran / 5 h / Heating 3: BBr₃ / CH₂Cl₂ / 1 h / 0 °C

Reference： [1]Ishihara, Kazuaki; Kurihara, Hideki; Matsumoto, Masayuki; Yamamoto, Hisashi [Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6920 - 6930]

3
[ 909187-39-9 ]
3-(2-Methoxy-3-methyl-phenyl)-[1,1']binaphthalenyl-2,2'-diol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Ba(OH)2*8H₂O, Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 12 h / 80 °C 2: 4M aq. HCl / tetrahydrofuran / 5 h / Heating

Reference： [1]Ishihara, Kazuaki; Kurihara, Hideki; Matsumoto, Masayuki; Yamamoto, Hisashi [Journal of the American Chemical Society, 1998, vol. 120, # 28, p. 6920 - 6930]

4
[ 52200-69-8 ]
[ 909187-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane at -70 - -20℃; for 0.5h;	89 To a solution of 2-bromo-6-methylphenol (0.520 g, 2.78 mmol) in 15 ML of acetone was added iodomethane (0.338 mL, 5.42 mmol) and potassium carbonate (0.768 g, 5.56 mmol). The reaction was heated to reflux and stirred overnight. Ammonium chloride (sat.) was added and the mixture was extracted with diethyl ether. The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated to afford 456 mg of 1-bromo-2-methoxy-3-methylbenzene as a clear oil. To a solution of 1-bromo-2-methoxy-3-methylbenzene (0.123 g, 0.61 mmol) in 3 mL of THF at -70° C. was added n-butyllithium (1.6 M in hexanes, 0.46 mL, 0.73 mmol) dropwise. The reaction stirred at -70° C. for 30 minutes and was then allowed to warm up to -20° C. Ammonium chloride (sat.) was added and the mixture was extracted with ethyl acetate, dried over sodium sulfate and filter to give 96 mg crude material. The crude material was purified by column chromatography (3/1 hexanes/ethyl acetate) to afford 40 mg of 2-methoxy-3-methylphenylboronic acid as a white solid. MS(ES+): 167.0 (M+H).

Reference： [1]Current Patent Assignee: AMGEN INC - US2006/199817, 2006, A1 Location in patent: Page/Page column 49

5
4-bromo-2-nitro-1-pentyl-1H-imidazole [ No CAS ]
[ 909187-39-9 ]
4-(2-methoxy-3-methylphenyl)-2-nitro-1-pentyl-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 85℃; for 8h; Inert atmosphere;

Reference： [1]Beesu, Mallesh; Caruso, Giuseppe; Salyer, Alex C. D.; Shukla, Nijunj M.; Khetani, Karishma K.; Smith, Luke J.; Fox, Lauren M.; Tanji, Hiromi; Ohto, Umeharu; Shimizu, Toshiyuki; David, Sunil A. [Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3311 - 3330]

6
tert-butyl 3-(7-chloro-8-fluoro-2-((tetrahydro-1H-pyrrolizin-7a(5H)-yl)methoxy)pyrido[4,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]
[ 909187-39-9 ]
tert-butyl 3-(8-fluoro-2-((hexahydro-1H-pyrrolizin-7a-yl)methoxy)-7-(2-methoxy-3-methylphenyl)pyrido[4,3-d]pyrimidin-4-yl)-3,8-diazabicyclo[3.2.1]octane-8-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium phosphate; [(di(1-adamantyl)butylphosphine)-2-(2′-amino-1,1′-biphenyl)]palladium(II) methanesulfonate In tetrahydrofuran at 60℃; for 2h; Inert atmosphere;	313.A Step A. (1 R.5 SVtert-butvl 3 -(8 -fluoro-2-(Yhexahydro- lH-pyrrolizin-7 a- vOmethoxv)-7-(2-methoxv-3-methvlphenvOpvrido[4.3-d1pvrimidin-4-vO-3.8- diazabicvclor3.2.11octane-8-carboxvlate. A mixture of (lR,5S)-tert-butyl 3 -(7-chl oro- 8 -fluoro-2- ((hexahydro-lH-pyrrolizin-7a-yl)methoxy)pyrido[4,3-d]pyrimidin-4-yl)-3,8- diazabicyclo[3.2.1 ]octane-8-carboxylate (150 mg, 281 pmol, 1.00 eq), (2-methoxy-3-methyl- phenyl) boronic acid (142 mg, 855 pmol, 3.04 eq), [2-(2- aminophenyl)phenyl]palladium(l+);bis(l-adamantyl)-butyl-phosphane;methanesulfonate (41.0 mg, 56.3 pmol, 0.20 eq), and K3PO4 (1.50 M, 500 pL, 2.67 eq) in THF (2.0 mL) was degassed and purged with N2 for 3 times, and then the mixture was stirred at 60 °C for 2 hours under N2 atmosphere. After completion, the reaction mixture was diluted with H2O (5.0 mL) and extracted with ethyl acetate (3 c 10 mL). The combined organic layers were washed with saturated brine (30 mL), dried over Na2SOr, filtered and concentrated under reduced pressure to give a residue. The residue was purified by reversed phase flash chromatography [C18, 0.1% FA in water, 0-50% MeCN] affording the title compound (120 mg, 69% yield). White solid; NMR (400 MHz, CDCb-d) d = 9.02 (s, 1H), 7.32-7.27 (m, 2H), 7.16-7.11 (m, 1H), 4.56 (br d, J = 12.4 Hz, 2H), 4.39-4.36 (m, 2H), 4.19 (s, 2H), 3.77-3.58 (m, 2H), 3.55 (s, 3H), 3.15-3.07 (m, 2H), 2.68-2.60 (m, 2H), 2.38 (s, 3H), 2.13-2.04 (m, 2H), 1.99-1.93 (m, 2H), 1.90-1.83 (m, 4H), 1.81-1.73 (m, 2H), 1.71-1.62 (m, 2H), 1.53 (s, 9H); LCMS [ESI, M+l]: 619.3.

Reference： [1]Current Patent Assignee: PFIZER INC; MIRATI THERAPEUTICS, INC. - WO2021/41671, 2021, A1 Location in patent: Paragraph 01158

7
[ 5419-55-6 ]
[ 578-58-5 ]
[ 909187-39-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-methylmethoxybenzene With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexane; cyclohexane at 5 - 20℃; for 7h; Large scale; Stage #2: Triisopropyl borate In hexane; tert-butyl methyl ether; cyclohexane at -70 - -20℃; Large scale;	1.1 Step 1 and 2 - Borylation of 2-Methylanisole [00176] The scale up was started using 40 kg (324 mol, 1 eq) 2-methylanisole (1), 50 kg TMEDA (1.3 eq) and 60 kg cyclohexane. n-Butyllithium solution (23% in hexanes, 115 kg, 1.3 eq) was added at 5-10 °C and after complete addition the line was rinsed with 30 kg cyclohexane. After 1 h at max. 10 °C, in process control (IPC) by HPLC with UV/Vis detection showed 20%area unreacted 2-methylanisole (peak at 10 min). The mixture was stirred at 5-20 °C for approx. 6 h total. At this point, IPC showed 10% area residual 2-methylanisole. (0260) [00177] The batch was cooled to -75 °C and MTBE (230 kg) was added during the cooling period at (0261) [00178] At this temperature the mixture was transferred to the quench reactor containing 15% aqueous HC1 (315 kg). IPCs showed residual 2-methylanisole at 6%area level. (0262) [00179] Subsequently, phases were separated, the organic layer was combined with water (240 kg) and 33% NaOH (53 kg) and layers were separated again. IPC showed no significant product content in the organic layer. (0263) [00180] The aqueous product solution was acidified and stirred for 2 h at (0264) [00181] The product (2, 48.5 kg; LOD: 21%) was additionally slurried with water (280 kg), filtered and the cake was washed with water (50 kg). The damp product resulting from this wash showed the expected purity (99.9%area). (0265) [00182] 42 kg of damp intermediate 2 was obtained. A sample (27 g) was dried in the lab overnight showing loss on drying (LOD) of -12%. The resulting dry product showed 103.6% potency by HPLC. Accordingly, yield for this step is calculated to be 38.3 kg (71%) 2-methoxy-3- methylphenylboronic acid.

Reference： [1]Current Patent Assignee: VENATORX PHARMACEUTICALS INC - WO2022/76070, 2022, A1 Location in patent: Paragraph 00176-00182

8
[ 909187-39-9 ]
[ 913836-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate; sodium hydroxide In lithium hydroxide monohydrate at 35℃; Large scale;	1.3 Step 3 - KMnC Oxidation [00183] Intermediate 2 (~38 kg dry product) was suspended in water (280 kg) and dissolved by addition of 33% NaOH solution (69 kg). Via solid lock, it was charged KMnO4 (100 kg total) starting with 5 kg portions. The exothermic effect observed after addition of a portion was in good agreement with the expected value of approx. 0.8-1 °C/kg. After addition of 30 kg, it was switched to 10 kg portions. A sample taken after 40 kg was showing the expected conversion level. Keeping the internal temperature at (0268) [00184] Damp intermediate 3 showing LOD of 19% was isolated (42.2 kg). This corresponded to 34.2 kg pure intermediate 3 (76%). Additionally, there was an amount of product sticking to the walls of the reactor (2-3 kg). The true yield of the reaction was therefore estimated to be at least 36 kg (80%). HPLC purity of the damp intermediate 3 by in-house analysis was 99.9% with 2-anisic acid and step 1 intermediate as the only impurities detected (each less than 0.1%).

Reference： [1]Current Patent Assignee: VENATORX PHARMACEUTICALS INC - WO2022/76070, 2022, A1 Location in patent: Paragraph 00183-00184

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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
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H230	May react explosively even in the absence of air
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
H251	Self-heating; may catch fire
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
H270	May cause or intensify fire; oxidizer
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Health hazards
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H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
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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

[ CAS No. 909187-39-9 ]

Quality Control of [ 909187-39-9 ]

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Calculated chemistry of [ 909187-39-9 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 909187-39-9 ]

Application In Synthesis of [ 909187-39-9 ]

[ 909187-39-9 ] Synthesis Path-Downstream 1~8

Related Functional Groups of [ 909187-39-9 ]

Organoboron

Aryls

Ethers

Precautionary Statements-General

Prevention

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Storage

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Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 909187-39-9 ]