4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER

Product Name: 4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER
CAS No.: 214360-57-3
Chemical Name: 4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER
Synonyms: 4-(Methylcarbamoyl)benzeneboronic Acid Pinacol Ester;(4-(METHYLCARBAMOYL)PHENYL)BORONIC ACID PINACOL ESTER;4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER;4-(N-Methylaminocarbonyl)phenylboronic acid,pinacol ester;4-N-Methylcarboxamidophenylboronic acid, pinacol ester;N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benz...;N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide;Benzamide, N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;N-Methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide
CBNumber: CB0289085
Molecular Formula: C14H20BNO3
Formula Weight: 261.12
MOL File: 214360-57-3.mol

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4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER Property

storage temp.: Store at room temperature
form: solid
Appearance: White to off-white Solid
CAS DataBase Reference: 214360-57-3

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Safety

WGK Germany: 3
HS Code: 2931900090

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: BML00117
Product name: 4-N-Methylcarboxamidophenylboronic acid, pinacol ester
Purity: Aldrich
Packaging: 1g
Price: $179
Updated: 2025/07/31

TRC

Product number: M329385
Product name: 4-N-Methylcarboxamidophenylboronic acid, pinacol ester
Packaging: 50mg
Price: $45
Updated: 2021/12/16

TRC

Product number: M329385
Product name: 4-N-Methylcarboxamidophenylboronic acid, pinacol ester
Packaging: 100mg
Price: $60
Updated: 2021/12/16

TRC

Product number: M329385
Product name: 4-N-Methylcarboxamidophenylboronic acid, pinacol ester
Packaging: 500mg
Price: $90
Updated: 2021/12/16

SynQuest Laboratories

Product number: 8H60-1-9K
Product name: 4-N-Methylcarboxamidophenylboronic acid, pinacol ester
Packaging: 1g
Price: $125
Updated: 2021/12/16

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4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER Chemical Properties,Usage,Production

Synthesis

27466-83-7

73183-34-3

214360-57-3

1. Dissolve 4-bromobenzoic acid (6.00 g, 29.8 mmol) in 80 mL of dichloromethane, add N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (6.30 g, 32.9 mmol), 4-(dimethylamino)pyridine (7.70 g, 63.0 mmol) and methylamine hydrochloride (2.23 g, 33.0 mmol). ). The mixture was stirred overnight, washed with 1.0 N hydrochloric acid, dried over anhydrous sodium sulfate and concentrated. The crude product was purified by rapid chromatography on silica gel using hexane/ethyl acetate as eluent to afford 4-bromo-N-methylbenzamide (5.80 g, 90%) as a white solid. 2. 4-Bromo-N-methylbenzamide (4.00 g, 18.9 mmol) was dissolved in 10 mL of 1,4-dioxane, and bis(pinacolato)diboron (11.9 g, 46.8 mmol), potassium acetate (5.50 g, 56.1 mmol), and [1,1'-bis(diphenylphosphino)ferrocenyl]-dichloropalladium(II) (0.410 g, 0.560 mmol) were added. 0.560 mmol). The mixture was heated at 90 °C overnight, filtered and concentrated. The residue was purified by rapid chromatography on silica gel using hexane/ethyl acetate as eluent to afford N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (4.50 g, 91%) as a white solid. 3. N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide was reacted with ethyl 2-(4-bromophenyl)-2-methylpropanoate to form ethyl 2-methyl-2-(4'-(methylcarbamoyl)-[1,1'-biphenyl]-4-yl)propanoate as an off-white solid according to General Method F. The reaction was completed by the following method. 4. Ethyl 2-methyl-2-(4'-(methylcarbamoyl)-[1,1'-biphenyl]-4-yl)propanoate (1.00 g, 3.07 mmol) was dissolved in a solvent mixture of 4 mL of tetrahydrofuran, 8 mL of methanol, and 3 mL of water and solid sodium hydroxide (0.640 g, 16.0 mmol) was added. After stirring at room temperature overnight, the reaction mixture was concentrated and dissolved in water. It was acidified with 1 N hydrochloric acid to pH~6 and extracted with ethyl acetate. The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated to afford 2-methyl-2-(4'-(methylcarbamoyl)-[1,1'-biphenyl]-4-yl)propionic acid (0.950 g, 100%) as a white solid. The compound can be used directly in the next step of the reaction without further purification. 5. 2-Methyl-2-(4'-(methylcarbamoyl)-[1,1'-biphenyl]-4-yl)propionic acid was reacted with quinuclidinium cyclic-3-ol according to General Method I to afford 4-N-methylcarboxyamino phenylboronic acid pinacol ester as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.47 (q, J = 4.5 Hz, 1H), 7.91 (d, J = 8.5 Hz, 2H), 7.74 (d, J = 6.5 Hz, 2H), 7.67-7.65 (m, 2H), 7.60 (s, 1H), 7.44 (d, J = 6.5 Hz, 2H), 4.43 ( m, 1H), 3.76 (m, 1H), 2.81-2.63 (m, 7H), 2.47-2.36 (m, 1H), 1.85 (m, 2H), 1.56-1.34 (m, 9H) ppm. 13C NMR (125 MHz, CD3OD) δ 170.4, 156.9, 149.1, 145.3, 139.2, 134.1, 128.8, 127.9, 126.7, 71.4, 56.1, 55.9, 48.0, 47.0, 30.0, 29.9, 27.0, 26.5, 24.6, 20.0 ppm. Purity: 100% (214 and 254 nm) LCMS; retention time: 1.72 min; (M + H+) 422.3.

References

[1] Patent: WO2014/43068, 2014, A1. Location in patent: Page/Page column 267; 268
[2] Patent: WO2006/44497, 2006, A2. Location in patent: Page/Page column 129; 130

4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER Preparation Products And Raw materials

Raw materials

Preparation Products

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214360-57-3, 4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTERRelated Search:

3-(Benzylaminocarbonyl)benzeneboronic acid pinacol ester 3-(N-CYCLOPROPYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine 4-bromo-N-methylpicolinamide 4-Methylamino-3-nitrophenylboronic acid,pinacol ester N-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-benzenemethanamine N-Methyl-2-[3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]acetamide Methyl({[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl})amine N-Methyl-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-carboxaMide N-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide N-methyl-N-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide 4-(N-CYCLOPROPYLAMINOCARBONYL)PHENYLBORONIC ACID, PINACOL ESTER 4-(3-ETHOXYCARBONYLPIPERIDINE)CARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER 1-BOC-4-[4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-BENZOYL]-PIPERAZINE 4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER 4-(MORPHOLINE)CARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER (4-METHYL-PIPERAZINE-1-YL)-[4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-PHENYL]-METHANONE PIPERAZIN-1-YL-[4-(4,4,5,5-TETRAMETHYL-[1,3,2]DIOXABOROLAN-2-YL)-PHENYL]-METHANONE

4-N-METHYLCARBOXAMIDOPHENYLBORONIC ACID, PINACOL ESTER

4-(N-Methylaminocarbonyl)phenylboronic acid,pinacol ester

N-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide

Benzamide, N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

(4-(METHYLCARBAMOYL)PHENYL)BORONIC ACID PINACOL ESTER

N-Methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)formamide

N-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benz...

4-<i>N</i>-Methylcarboxamidophenylboronic acid, pinacol ester

4-(Methylcarbamoyl)benzeneboronic Acid Pinacol Ester

214360-57-3