N-Acetic acid-indole-3-carboxaldehyde Chemical Properties

Melting point:

197-200 °C(lit.)

Boiling point:

458.5±25.0 °C(Predicted)

Density 

1.30±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,2-8°C

pka

4.15±0.10(Predicted)

form 

solid

Appearance

Light yellow to yellow Solid

Sensitive 

Air Sensitive

BRN 

5431204

InChI

InChI=1S/C11H9NO3/c13-7-8-5-12(6-11(14)15)10-4-2-1-3-9(8)10/h1-5,7H,6H2,(H,14,15)

InChIKey

ZUUGBTJTGRTIFK-UHFFFAOYSA-N

SMILES

N1(CC(O)=O)C2=C(C=CC=C2)C(C=O)=C1

CAS DataBase Reference

138423-98-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

8-10-23

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:SigmaAldrich

N-Acetic acid-indole-3-carboxaldehyde Usage And Synthesis

Chemical Properties

Solid

Uses

Handle to synthesize an indolecarboxaldehyde resin by coupling to an amino-resin. Amines and derivatives can be immobilized by reductive amination of this aldehyde resin. Mild cleavage with 50% TFA

reaction suitability

reagent type: cross-linking reagent

Synthesis

Ethyl (3-formyl-1H-indol-1-yl)acetate (15.9 g, 69 mmol) was dissolved in 1,4-dioxane (100 mL), 1 N sodium hydroxide solution (10 mL) was added, and the resulting mixture was stirred at 0 °C. The reaction mixture was then stirred at room temperature for 4 days. After completion of the reaction, water (500 mL) was added and the mixture was washed with ether (150 mL). The aqueous phase was acidified with 5 N hydrochloric acid to pH < 2 and subsequently extracted with ethyl acetate (250 mL + 150 mL) in two fractions. The organic phases were combined, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give (3-formylindol-1-yl)acetic acid (10.3 g, 73% yield) as a white solid. The product was characterized by 1H-NMR (DMSO-d6): δH=5.20 (2H, s), 7.3 (2H, m), 7.55 (1H, d), 8.12 (1H, d), 8.30 (1H, s), 9.95 (1H, s), 13.3 (1H, br s).

References

[1] Patent: WO2006/82245, 2006, A1. Location in patent: Page/Page column 230
[2] Patent: US2005/65066, 2005, A1. Location in patent: Page/Page column 120
[3] Patent: WO2004/80480, 2004, A1. Location in patent: Page/Page column 226
[4] Patent: WO2006/5683, 2006, A1. Location in patent: Page/Page column 225
[5] Patent: US2003/229120, 2003, A1. Location in patent: Page 75

N-Acetic acid-indole-3-carboxaldehyde(138423-98-0)Related Product Information

• N-Acetic acid-indole-3-carboxaldehyde
• Indole-3-carboxaldehyde
• clometacin
• Indole
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• 1H-INDOLE-1-ACETIC ACID, 3-FORMYL-, 1,1-DIMETHYLETHYL ESTER
• CHEMBRDG-BB 7865272
• (3-ISOBUTYRYL-INDOL-1-YL)-ACETIC ACID
• 2-(3-FORMYL-1H-INDOL-1-YL)PROPANOIC ACID
• (3-FORMYL-INDOL-1-YL)-ACETIC ACID ETHYL ESTER
• (3-ACETYL-2-METHYL-INDOL-1-YL)-ACETIC ACID
• [3-(FURAN-2-CARBONYL)-INDOL-1-YL]-ACETIC ACID
• ethyl (3-formyl-2-methyl-1H-indol-1-yl)acetate
• (3-FORMYL-INDOL-1-YL)-ACETIC ACID METHYL ESTER
• (3-ACETYL-INDOL-1-YL)-ACETIC ACID
• (3-CYCLOPROPANECARBONYL-INDOL-1-YL)-ACETIC ACID
• CHEMBRDG-BB 9070563
• (3-FORMYL-2-METHYL-INDOL-1-YL)-ACETIC ACID METHYL ESTER