ChemicalBook > CAS DataBase List > ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE

ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE

Product Name
ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE
CAS No.
100123-25-9
Chemical Name
ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE
Synonyms
ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE;5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLIC ACID ETHYL ESTER;Ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate - [E37736];1H-Indole-2-carboxylic acid, 5-bromo-3-formyl-, ethyl ester
CBNumber
CB9428546
Molecular Formula
C12H10BrNO3
Formula Weight
296.12
MOL File
100123-25-9.mol
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ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE Property

Melting point:
245 °C(Solv: ethanol (64-17-5))
Boiling point:
476.7±45.0 °C(Predicted)
Density 
1.608±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
pka
12.56±0.30(Predicted)
Appearance
Off-white to light yellow Solid
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

TRC
Product number
E702910
Product name
Ethyl5-Bromo-3-formyl-1H-indole-2-carboxylate
Packaging
100mg
Price
$105
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
HCH0035738
Product name
ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE
Purity
95.00%
Packaging
2G
Price
$2021.25
Updated
2021/12/16
Ambeed
Product number
A190769
Product name
Ethyl5-bromo-3-formyl-1H-indole-2-carboxylate
Purity
98%
Packaging
250mg
Price
$66
Updated
2021/12/16
Crysdot
Product number
CD11370601
Product name
Ethyl5-bromo-3-formyl-1H-indole-2-carboxylate
Purity
95+%
Packaging
250mg
Price
$74
Updated
2021/12/16
Ambeed
Product number
A190769
Product name
Ethyl5-bromo-3-formyl-1H-indole-2-carboxylate
Purity
98%
Packaging
1g
Price
$146
Updated
2021/12/16
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ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE Chemical Properties,Usage,Production

Uses

Ethyl 5-Bromo-3-formyl-1h-indole-2-carboxylate is a versatile building block. It was used as a reactant in the synthetic preparation of hydroxyindolecarboxylates by Baeyer-Villiger oxidation.

Synthesis

16732-70-0

100123-25-9

Oxalyl chloride (3.43 mL, 39.9 mmol) was slowly added dropwise to a mixed solution containing DMF (30 mL) and dichloromethane (80 mL) at 0 °C while maintaining stirring. After the dropwise addition was completed, stirring was continued at 0 °C for 20 min. Subsequently, a solution of ethyl 5-bromoindole-2-carboxylate (10 g, 37.3 mmol) dissolved in DMF (80 mL) was added. The reaction mixture was transferred to room temperature and stirred continuously for 24 hours. Upon completion of the reaction, the mixture was poured into saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic phases were combined, washed sequentially with water and saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Finally, the target product ethyl 5-bromo-3-formyl-1H-indole-2-carboxylate was obtained by ethanol recrystallization in a yield of 8.9 g and 81%.

References

[1] Patent: WO2006/77366, 2006, A1. Location in patent: Page/Page column 152
[2] Patent: WO2006/77367, 2006, A1. Location in patent: Page/Page column 89

ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE Preparation Products And Raw materials

Raw materials

Preparation Products

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ETHYL 5-BROMO-3-FORMYL-1H-INDOLE-2-CARBOXYLATE Suppliers

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