1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Product Name: 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
CAS No.: 837392-62-8
Chemical Name: 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Synonyms: 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole;1-Methyl-5-(4;AKOS BRN-1159;2-dioxaborolan-2-yl)-1H-indole;Pinacol 1-methylindole-5-borate;1-Methylindole-5-borate pinacol ester;1-Methyl-5-indoleboronic acid pinacol ester;1-METHYLINDOLE-5-BORONIC ACID, PINACOL ESTER;1-Methyl-5-indolylboronic acid, pinacol ester;1-Methyl-1H-indole-5-boronic acid, pinacol ester
CBNumber: CB4296474
Molecular Formula: C15H20BNO2
Formula Weight: 257.14
MOL File: 837392-62-8.mol

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1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Property

Melting point:: 110-114 °C (lit.)
Boiling point:: 391.3±15.0 °C(Predicted)
Density: 1.05±0.1 g/cm3(Predicted)
storage temp.: under inert gas (nitrogen or Argon) at 2-8°C
form: solid
Appearance: Off-white to light yellow Solid
InChI: InChI=1S/C15H20BNO2/c1-14(2)15(3,4)19-16(18-14)12-6-7-13-11(10-12)8-9-17(13)5/h6-10H,1-5H3
InChIKey: JQLYKUPEQYNDFF-UHFFFAOYSA-N
SMILES: N1(C)C2=C(C=C(B3OC(C)(C)C(C)(C)O3)C=C2)C=C1

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Safety

Hazard Codes: Xi
Safety Statements: 22-24/25
WGK Germany: 3
Hazard Note: Irritant
HS Code: 2933299090

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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

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 640395
Product name: 1-Methylindole-5-boronic acid pinacol ester
Purity: 97%
Packaging: 1g
Price: $243
Updated: 2025/07/31

Sigma-Aldrich

Product number: 640395
Product name: 1-Methylindole-5-boronic acid pinacol ester
Purity: 97%
Packaging: 5g
Price: $329
Updated: 2023/06/20

TRC

Product number: M338053
Product name: 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
Packaging: 10mg
Price: $45
Updated: 2021/12/16

SynQuest Laboratories

Product number: 8H60-1-U3
Product name: 1-Methyl-1H-indole-5-boronic acid, pinacol ester
Purity: 97%
Packaging: 1g
Price: $60
Updated: 2021/12/16

AK Scientific

Product number: AMTB258
Product name: 1-Methyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole
Packaging: 1g
Price: $40
Updated: 2021/12/16

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1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Chemical Properties,Usage,Production

Chemical Properties

off-white powder

Synthesis

10075-52-2

73183-34-3

837392-62-8

The general procedure for the synthesis of 1-methylindole-5-boronic acid pinacol ester from 5-bromo-1-methyl-1H-indole and biboronic acid pinacol ester is as follows: the synthesis was carried out according to the literature method with appropriate adjustments. To an 8-dram vial equipped with a magnetic stirrer were sequentially added pinacol bis(boronic acid) ester (2 mmol, 508 mg), 5-bromo-1-methyl-1H-indole (2.1 mmol, 441 mg), [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) dichloride (0.06 mmol, 44 mg), potassium acetate (6 mmol, 589 mg), and degassed 1,1'-bis(diphenylphosphino)ferrocene(III). ), and degassed 1,4-dioxane (10 mL). The reaction mixture was purged under a strong stream of nitrogen for 5 min to deoxygenate, followed by transferring the reaction system to an oil bath preheated to 80 °C with continuous stirring for 48 h. The reaction was carried out in a cooled room with a temperature range of 0.5 °F to 0.5 °F. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was filtered through a diatomaceous earth pad and washed with ethyl acetate (50 mL). The filtrates were combined and concentrated under reduced pressure to remove the solvent. The crude product was purified by fast column chromatography with petroleum ether as eluent, followed by a 5% to 12% gradient elution of ether/petroleum ether to afford 342 mg (67% yield) of the target product, 1-methylindole-5-boronic acid pinacol ester, as a white solid.

References

[1] Synlett, 2018, vol. 29, # 15, p. 2031 - 2034
[2] ACS Catalysis, 2018, vol. 8, # 5, p. 4049 - 4054
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 34, p. 10999 - 11003
[4] Angew. Chem., 2018, # 130, p. 11165 - 11169,5
[5] Patent: WO2016/180537, 2016, A1. Location in patent: Page/Page column 133

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Preparation Products And Raw materials

Raw materials

Preparation Products

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1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Suppliers

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837392-62-8, 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleRelated Search:

1-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-INDOLE

1-METHYLINDOLE-5-BORONIC ACID, PINACOL ESTER

AKOS BRN-1159

1-Methyl-5-(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)-1H-indole

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1-Methyl-5-(4

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1-Methyl-1H-indole-5-boronic acid, pinacol ester 97%

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole, 2-(1-Methyl-1H-indol-5-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole

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

1-Methyl-5-indolylboronic acid, pinacol ester

1-Methyl-1H-indole-5-boronic acid, pinacol ester

1H-Indole, 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

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

1-Methylindole-5-borate pinacol ester

Pinacol 1-methylindole-5-borate

837392-62-8

C15H20BNO2

Boronate Esters

Boronic Acids and Derivatives

Chemical Synthesis

Heteroaryl Boronate Esters

Organometallic Reagents