[ CAS No. 590418-04-5 ]

Name: 590418-04-5|4,4,5,5-Tetramethyl-2-(3-methyl-4-nitrophenyl)-1,3,2-dioxaborolane|95+%
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Quality Control of [ 590418-04-5 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 590418-04-5 ]

CAS No. :	590418-04-5	MDL No. :	MFCD10699700
Formula :	C₁₃H₁₈BNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	263.10	Pubchem ID :	-
Synonyms :

Computed Properties of [ 590418-04-5 ]

TPSA :Topological Polar Surface Area	-	H-Bond Acceptor Count :	-
XLogP3 :	-	H-Bond Donor Count :	-
SP3 :	-	Rotatable Bond Count :	-

Safety of [ 590418-04-5 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P210-P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P332+P313-P337+P313-P362-P370+P378-P403+P233-P403+P235-P405-P501	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 590418-04-5 ]

Upstream synthesis route of [ 590418-04-5 ]
Downstream synthetic route of [ 590418-04-5 ]

[ 590418-04-5 ] Synthesis Path-Upstream 1~1

1
[ 590418-04-5 ]
[ 590418-05-6 ]

Reference： [1] Patent: US2004/44258, 2004, A1, . Location in patent: Page 157

[ 590418-04-5 ] Synthesis Path-Downstream 1~7

Yield	Reaction Conditions	Operation in experiment
84%

2
[ 590418-04-5 ]
[ 590418-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;platinum(IV) oxide; In methanol; at 20.0℃; for 0.5h;	A solution of Intermediate 102 (4.20 g) in methanol (100 ml) was added with platinum oxide (50 mg, Ald) and stirred at room temperature for 30 minutes under a hydrogen atmosphere. The reaction mixture was filtered, and the solvent of the filtrate was evaporated under reduced pressure to obtain the title compound (Intermediate 103, 2.81 g). Mass (LCMS): 234 (M++1), retention time: 3.04 minutes (elution condition: B).

Reference： [1]Patent: US2004/44258,2004,A1 .Location in patent: Page 157

3
[ 590418-04-5 ]
[ 138647-49-1 ]
[ 1051930-31-4 ]

Yield	Reaction Conditions	Operation in experiment
54%	With sodium carbonate; lithium chloride In toluene at 80℃; Inert atmosphere;	1 [00525] 4-(3-Methyl-4-nitro-phenyl)-3,6-dihydro-2H-pyridine-l-carboxylic acid tert-butyl ester (61): A magnetically stirred solution of tert-butyl 4- { [(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-l (2H)-carboxylate 59 (1.51 g, 5.74 mmol), Pd(PPh3)4 (671 mg, 0.58 mmol), 3,3,4,4-tetramethyl-l-(3-methyl-4- nitrophenyl)borolane 60 (1.9 g, 5.74 mmol), LiCl ( 730 mg, 17.22 mmol) and Na2CO3 (8.2 mL) in toluene was heated to reflux at 8O0C under N2 atm. Upon completion, the reaction was cooled to room temperature, the solvent was concentrated in vacuo. The residue thus obtained, was suspended in water, and extracted several times with ethyl acetate. The organic phases were washed with water and brine and the residue obtained after evaporation of the solvent was purified by flash chromatography on silica gel (elution with 15% ethyl acetate/hexanes) to give tert-butyl 4-(3-methyl-4-nitrophenyl)-3,6- dihydropyridine- l(2H)-carboxylate 61 as a red solid in 54% yield.

Reference： [1]Current Patent Assignee: MYREXIS, INC. - WO2010/111406, 2010, A2 Location in patent: Page/Page column 116

4
[ 590418-04-5 ]
[ 1221232-29-6 ]
4-chloro-6-(3-methyl-4-nitrophenyl)isoquinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 50℃; for 4h;	060.1 Step 1: 4-chloro-6-(3-methyl-4-nitrophenyl)isoquinoline Na2C03(524.5 mg, 4.95 mmol, 2 equiv) and Pd(dppf)Cl2 (181.0 mg, 0.25 mmol, 0.1 equiv) were added to a solution of 6-bromo-4-chloroisoquinoline (600 mg, 2.47 mmol, 1 equiv) and 4,4,5, 5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2-dioxaborolane (976.4 mg, 3.71 mmol, 1.5 equiv) in DME (6 ml) and water (1.5 mL). The mixture was stirred at 50 °C for four hours. Volatiles were removed under reduced pressure and the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10: 1) to afford the desired final product as a brown solid (700mg, 95%)
95%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 50℃; for 4h;	60.1 Step 1: 4-chloro-6-(3-methyl-4-nitrophenyl)isoquinoline Na2C03(524.5 mg, 4.95 mmol, 2 equiv) and Pd(dppf)Ch (181.0 mg, 0.25 mmol, 0.1 equiv) were added to a solution of 6-bromo-4-chloroisoquinoline (600 mg, 2.47 mmol, 1 equiv) and 4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2-dioxaborolane (976.4 mg, 3.71 mmol, 1.5 equiv) in DME (6 ml) and water (1.5 mL). The mixture was stirred at 50 °C for four hours. (1195) Volatiles were removed under reduced pressure and the residue was purified by silica gel column chromatography with petroleum ether/ethyl acetate (10: 1) to afford the desired final product as a brown solid (700mg, 95%)

Reference： [1]Current Patent Assignee: IDEAYA BIOSCIENCES INC. - WO2019/18562, 2019, A1 Location in patent: Paragraph 0348
[2]Current Patent Assignee: IDEAYA BIOSCIENCES INC. - WO2020/18848, 2020, A1 Location in patent: Paragraph 0479

5
[ 590418-04-5 ]
2-chloro-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine [ No CAS ]
2-(3-methyl-4-nitrophenyl)-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene at 100℃;	135.6 Step 6: 2-(3-methyl-4-nitrophenyl)-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine mixture of 2-chloro-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine (400 mg, 1.71 mmol, 1 equiv), 4,4,5, 5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2-dioxaborolane (450.6 mg, 1.71 mmol, 1 equiv), Na2C03 (363.0 mg, 3.42 mmol, 2 equiv), Pd(PPh3)4 (197.9 mg, 0.17 mmol, 0.1 equiv) in toluene (8 mL) and EtOH (4 mL) was stirred overnight at 100 °C. The solids were filtered out and the solution concentrated. The residue was purified by preparative TLC with ethyl acetate/petroleum ether (1/5) as eluent to afford the desired product as a yellow solid in 40% yield.
40%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; toluene at 100℃;	135.6 Step 6: 2-(3-methyl-4-nitrophenyl)-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine A mixture of 2-chloro-6-(trifluoromethyl)pyrido[3,2-d]pyrimidine (400 mg, 1.71 mmol, (1623) 1 equiv), 4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2-dioxaborolane (450.6 mg, 1.71 mmol, 1 equiv), Na2C03 (363.0 mg, 3.42 mmol, 2 equiv), Pd(PPh3)4 (197.9 mg, 0.17 mmol, 0.1 equiv) in toluene (8 mL) and EtOH (4 mL) was stirred overnight at 100 °C. The solids were filtered out and the solution concentrated. The residue was purified by preparative TLC with ethyl acetate/petroleum ether (1/5) as eluent to afford the desired product as a yellow solid in 40% yield.

Reference： [1]Current Patent Assignee: IDEAYA BIOSCIENCES INC. - WO2019/18562, 2019, A1 Location in patent: Paragraph 0496
[2]Current Patent Assignee: IDEAYA BIOSCIENCES INC. - WO2020/18848, 2020, A1 Location in patent: Paragraph 0627

6
[ 25676-75-9 ]
[ 590418-04-5 ]
1-methyl-4-(3-methyl-4-nitrophenyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 100℃; for 16h;	General Method D: Suzuki Coupling Reaction Intermediate C-V-4: 1-methyl-4-(3-methyl-4-nitrophenyl)-1H-imidazole General Method D: Suzuki Coupling Reaction Intermediate C-V-4: 1-methyl-4-(3-methyl-4-nitrophenyl)-1H-imidazole A suspension of 4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-1,3,2-dioxaborolane (0.80 g, 3.0 mmol) and 4-bromo-1-methyl-1H-imidazole (0.49 g, 3.0 mmol) in a mixture of 1,4-dioxane (12 mL) and water (0.5 mL) was treated with potassium carbonate (1.26 g, 9.1 mmol) and the suspension was allowed to stir. The reaction mixture was degassed by bubbling argon for two minutes and treated with Pd(dppf)Cl2.DCM adduct (0.50 g, 0.61 mmol). The resulting reaction mixture was heated at 100° C. 16 h. The reaction was diluted with water and extracted with DCM (4*25 mL). The organics were combined and dried over anhydrous Na2SO4, filtered and concentrated to dryness under vacuum to afford a black oil. The black oil was purified using silica gel (0 to 15% MeOH/DCM, 15 CV's) to obtain 1-methyl-4-(3-methyl-4-nitrophenyl)-1H-imidazole (0.31 g, 47% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.02 (d, J=8.6 Hz, 1H), 7.84 (d, J=7.7 Hz, 2H), 7.77 (d, J=8.6 Hz, 1H), 7.72 (s, 1H), 3.70 (s, 3H), 2.57 (s, 3H); LC-MS (ESI) m/z: 218.2 (M+H+).
47%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium carbonate In 1,4-dioxane; water at 100℃; for 16h;	Intermediate C 1 : 1 -methyl -4-(3 -methyl -4-nitrophenyl)- 1 H-imidazol e : General procedure: A suspension of 4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-l,3,2- dioxaborolane (0.80 g, 3.0 mmol) and 4-bromo-l -methyl- lH-imidazole (0.49 g, 3.0 mmol) in a mixture of 1,4-dioxane (12 mL) and water (0.5 mL) was treated with potassium carbonate (1.26 g, 9.1 mmol) and the suspension was allowed to stir. The reaction mixture was degassed by bubbling argon for two minutes and treated with Pd(dppf)Ch.DCM adduct (0.50 g, 0.61 mmol). The resulting reaction mixture was heated at 100 °C 16 h. The reaction was diluted with water and extracted with DCM (4 x 25 mL). The organics were combined and dried over anhydrous NaiSCE, filtered and concentrated to dryness under vacuum to afford a black oil. The black oil was purified using silica gel (0 to 15 % MeOH/DCM, 15 CV's) to obtain l-methyl-4-(3-methyl-4-nitrophenyl)-lH-imidazole (0.31 g, 47 % yield). 1H NMR (400 MHz, DMSO-de): d 8.02 (d, J = 8.6 Hz, 1H), 7.84 (d, J = 7.7 Hz, 2H), 7.77 (d, J = 8.6 Hz, 1H), 7.72 (s, 1H), 3.70 (s, 3H), 2.57 (s, 3H); LC-MS (ESI) m/z: 218.2 (M+H+).

Reference： [1]Current Patent Assignee: DECIPHERA PHARMACEUTICALS LLC - US2020/354352, 2020, A1 Location in patent: Paragraph 0239-0240
[2]Current Patent Assignee: DECIPHERA PHARMACEUTICALS LLC - WO2020/257180, 2020, A1 Location in patent: Paragraph 000294

7
[ 590418-04-5 ]
3-bromo-1-(4-(methoxymethoxy)phenyl)-1H-1,2,4-triazole [ No CAS ]
1-(4-(methoxymethoxy)phenyl)-3-(3-methyl-4-nitrophenyl)-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 100℃; for 8h;	109 Example 109: Preparation of 1-(4-(methoxymethoxy)phenyl)-3-(3-methyl-4- nitrophenyl)-1H-1,2,4-triazole (C515) 3-Bromo-1-(4-(methoxymethoxy)phenyl)-1H-1,2,4-triazole (C444; 1.2 g, 4.22 mmol), 4,4,5,5-tetramethyl-2-(3-methyl-4-nitrophenyl)-1,3,2-dioxaborolane (1.33 g, 5.07 mmol), potassium phosphate tribasic (2.69 g, 12.67 mmol) and XPhos-Pd-G3 precatalyst (0.072 g, 0.084 mmol) were combined in a 10:1 mixture of dioxane (12.8 mL) and water (1.28 mL). The mixture was heated to 100 °C for 8 h. The mixture was cooled and partitioned between DCM and brine. Separation and concentration of the organic solvents afforded material that was purified on silica gel eluting with 0 - 30% acetone-hexanes. The title compound was isolated as an orange waxy solid (1.00 g, 70%):1H NMR (400 MHz, CDCl3) d 8.52 (s, 1H), 8.20 (d, J = 1.8 Hz, 1H), 8.16 (dd, J = 8.5, 1.9 Hz, 1H), 8.09 (d, J = 8.5 Hz, 1H), 7.69- 7.62 (m, 2H), 7.22- 7.17 (m, 2H), 5.24 (s, 2H), 3.52 (s, 3H), 2.70 (s, 3H); ESIMS m/z 341.0 ([M+H]+).

Reference： [1]Current Patent Assignee: CORTEVA INC - WO2021/11722, 2021, A1 Location in patent: Page/Page column 336

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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
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
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
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

[ CAS No. 590418-04-5 ]

Quality Control of [ 590418-04-5 ]

Related Doc. of [ 590418-04-5 ]

Product Details of [ 590418-04-5 ]

Computed Properties of [ 590418-04-5 ]

Safety of [ 590418-04-5 ]

Application In Synthesis of [ 590418-04-5 ]

[ 590418-04-5 ] Synthesis Path-Upstream 1~1

[ 590418-04-5 ] Synthesis Path-Downstream 1~7

Related Functional Groups of [ 590418-04-5 ]

Nitroes

Organoboron

Aryls

Organoboron

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 590418-04-5 ]