3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

Name: 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID
Brand: Zhengzhou Whchem

CAS：459423-32-6 | 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID | Whchem

CAS: 459423-32-6

Other Names

3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID;3-(1-ADAMANTYL)-4-METHOXYPHENYLBORONIC ACID;3-(Adamantan-1-yl)-4-methoxybenzeneboronic acid;3-(Adamantan-1-yl)-4-methoxybenzeneboronic acid 96%;[4-Methoxy-3-(tricyclo[3.3.1.1(3,7)]dec-1-yl)phenyl]boronic acid;[3-(adaMantan-1-yl)-4-Methoxyphenyl]boronic acid;Boronic acid,B-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-;3-Adamant-1-yl-4-methoxybenzeneboronic acid

Structure - 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

Molecular Formula

Purity

>97%

Molecular Weight

286.17 g/mol

EINECS

Structure Available Verified Product

English Name	3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID
English Synonyms	3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID;3-(1-ADAMANTYL)-4-METHOXYPHENYLBORONIC ACID;3-(Adamantan-1-yl)-4-methoxybenzeneboronic acid;3-(Adamantan-1-yl)-4-methoxybenzeneboronic acid 96%;[4-Methoxy-3-(tricyclo[3.3.1.1(3,7)]dec-1-yl)phenyl]boronic acid;[3-(adaMantan-1-yl)-4-Methoxyphenyl]boronic acid;Boronic acid,B-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-;3-Adamant-1-yl-4-methoxybenzeneboronic acid
CAS Number	459423-32-6
Molecular Formula	C17H23BO3
Molecular Weight	286.17 g/mol
EINECS Number
Related Categories
Mol File	Download MOL File
Structure Image

Property	Value
Melting point	239-242
Boiling point	475.0±55.0 °C (Predicted)
Density	1.20±0.1 g/cm³ (Predicted)
Storage condition	Inert atmosphere, 2-8°C
Acidity Coefficient (pKa)	8.94±0.10 (Predicted)
Appearance	White to off-white solid
InChI	InChI=1S/C17H23BO3/c1-21-16-3-2-14(18(19)20)7-15(16)17-8-11-4-12(9-17)6-13(5-11)10-17/h2-3,7,11-13,19-20H,4-6,8-10H2,1H3
InChIKey	FPZOBRFHRPQGAA-UHFFFAOYSA-N
SMILES	B(C1=CC=C(OC)C(C23CC4CC(CC(C4)C2)C3)=C1)(O)O

3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID (CAS 459423-32-6) is a high-purity fine chemical intermediate widely used in organic synthesis, pharmaceutical R&D, agrochemical manufacturing and specialty chemical applications.

As a professional supplier, Zhengzhou Whchem provides 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID with >97% purity, COA, structure confirmation and flexible packaging, available from research quantities to commercial scale with global shipping.

Category	Description (English Translation)
Uses & Synthesis Methods Synthetic Route Diagram 3-(1-Adamantyl)-4-methoxyphenylboronic Acid	Uses & Synthesis Methods Uses: 3-(1-Adamantyl)-4-methoxyphenylboronic acid is used in biochemical research, reference standards, pharmaceutical intermediates, etc. Production Method: Starting Materials: 121-43-7 (Trimethyl borate) 104224-63-7 (2-(1-Adamantyl)-4-bromoanisole) 459423-32-6 (3-(1-Adamantyl)-4-methoxyphenylboronic acid) Step B: Synthesis of 3-(1-Adamantyl)-4-methoxyphenylboronic acid Example 2: In a 1 L three-necked flask equipped with a stirrer, reflux condenser, and dropping funnel, a mixture of 8 g (0.33 mol) of magnesium turnings and 200 mL of anhydrous tetrahydrofuran was added, followed by 8 g (0.19 mol) of crushed anhydrous lithium chloride. The air in the flask was replaced with argon, and subsequent operations were carried out under an inert atmosphere. Under vigorous stirring, 11 g (5 mL, 0.06 mol) of 1,2-dibromoethane was added in one portion. After the vigorous reaction subsided, a solution of 50 g (0.16 mol) of 2-(1-adamantyl)-4-bromoanisole in 400 mL of THF was added dropwise, maintaining a rate that kept the reaction at a gentle reflux. After the addition was complete, the mixture was stirred and heated at a gentle reflux for 30 minutes. Stirring was stopped, and the resulting Grignard reagent was decanted from the residual magnesium into an Erlenmeyer flask that had been flushed with argon and cooled to 0°C, and kept sealed for 2 hours. In another 1 L three-necked flask, 33 g (36 mL, 0.35 mol) of trimethyl borate and 100 mL of anhydrous THF were added and stirred. The resulting solution was cooled to 0-5°C (ice-water bath), and the pre-prepared Grignard reagent was added dropwise over 10 minutes under vigorous stirring. The reaction mixture was allowed to stand overnight (16 hours) in a 0-5°C refrigerator. After cooling, 50 mL of hydrochloric acid (diluted with 50 mL of water) was added under vigorous stirring to quench the reaction. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was diluted with 200 mL of water and extracted twice with 100 mL of diethyl ether. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure (bath temperature about 50°C). The residue was treated with 200 mL of ethyl acetate and allowed to stand overnight in a refrigerator. The precipitate was collected by filtration and dried at 100°C to afford 30 g (68% yield) of 3-(1-adamantyl)-4-methoxyphenylboronic acid (melting point 300°C). Example 10: The reaction was carried out as described in Example 2, except that the reaction of the 3-(1-adamantyl)-4-methoxyphenylmagnesium bromide solution with trimethyl borate was performed at -70°C, yielding 30.6 g (69% yield) of 3-(1-adamantyl)-4-methoxyphenylboronic acid. References: [1] Russian Journal of General Chemistry, 2010, vol. 80, # 4, p. 868 - 869 [2] Patent: US2010/160677, 2010, A1. Location in patent: Page/Page column 3-4

Category

Description (English Translation)

Uses & Synthesis Methods

Synthetic Route Diagram

3-(1-Adamantyl)-4-methoxyphenylboronic Acid

Uses & Synthesis Methods

Uses: 3-(1-Adamantyl)-4-methoxyphenylboronic acid is used in biochemical research, reference standards, pharmaceutical intermediates, etc.

Production Method:

Starting Materials:

121-43-7 (Trimethyl borate)

104224-63-7 (2-(1-Adamantyl)-4-bromoanisole)

459423-32-6 (3-(1-Adamantyl)-4-methoxyphenylboronic acid)

Step B: Synthesis of 3-(1-Adamantyl)-4-methoxyphenylboronic acid

Example 2: In a 1 L three-necked flask equipped with a stirrer, reflux condenser, and dropping funnel, a mixture of 8 g (0.33 mol) of magnesium turnings and 200 mL of anhydrous tetrahydrofuran was added, followed by 8 g (0.19 mol) of crushed anhydrous lithium chloride. The air in the flask was replaced with argon, and subsequent operations were carried out under an inert atmosphere. Under vigorous stirring, 11 g (5 mL, 0.06 mol) of 1,2-dibromoethane was added in one portion. After the vigorous reaction subsided, a solution of 50 g (0.16 mol) of 2-(1-adamantyl)-4-bromoanisole in 400 mL of THF was added dropwise, maintaining a rate that kept the reaction at a gentle reflux. After the addition was complete, the mixture was stirred and heated at a gentle reflux for 30 minutes. Stirring was stopped, and the resulting Grignard reagent was decanted from the residual magnesium into an Erlenmeyer flask that had been flushed with argon and cooled to 0°C, and kept sealed for 2 hours.

In another 1 L three-necked flask, 33 g (36 mL, 0.35 mol) of trimethyl borate and 100 mL of anhydrous THF were added and stirred. The resulting solution was cooled to 0-5°C (ice-water bath), and the pre-prepared Grignard reagent was added dropwise over 10 minutes under vigorous stirring. The reaction mixture was allowed to stand overnight (16 hours) in a 0-5°C refrigerator. After cooling, 50 mL of hydrochloric acid (diluted with 50 mL of water) was added under vigorous stirring to quench the reaction. The mixture was transferred to a separatory funnel and the layers were separated. The aqueous layer was diluted with 200 mL of water and extracted twice with 100 mL of diethyl ether. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure (bath temperature about 50°C). The residue was treated with 200 mL of ethyl acetate and allowed to stand overnight in a refrigerator. The precipitate was collected by filtration and dried at 100°C to afford 30 g (68% yield) of 3-(1-adamantyl)-4-methoxyphenylboronic acid (melting point 300°C).

Example 10: The reaction was carried out as described in Example 2, except that the reaction of the 3-(1-adamantyl)-4-methoxyphenylmagnesium bromide solution with trimethyl borate was performed at -70°C, yielding 30.6 g (69% yield) of 3-(1-adamantyl)-4-methoxyphenylboronic acid.

References:

[1] Russian Journal of General Chemistry, 2010, vol. 80, # 4, p. 868 - 869

[2] Patent: US2010/160677, 2010, A1. Location in patent: Page/Page column 3-4

Category	Value
Hazard Symbol	Xi
Hazard Note	Irritant/Keep Cold
HS Code (Customs)	2931900090

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3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

CAS：459423-32-6 | 3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID | Whchem

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3-(1-ADAMANTYL)-4-METHOXYBENZENEBORONIC ACID

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