2-METHYLINDOLE-3-ACETIC ACID Chemical Properties

Melting point:

205 °C (dec.) (lit.)

Boiling point:

418.2±30.0 °C(Predicted)

Density 

1.299±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

4.19±0.30(Predicted)

color 

Pale Brown to Light Brown

BRN 

152701

CAS DataBase Reference

1912-43-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Safety Statements 

22-24/25

WGK Germany 

3

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-METHYLINDOLE-3-ACETIC ACID Usage And Synthesis

Uses

2-Methylindole-3-acetic Acid is a derivative of Indole-3-acetic acid which is a plant growth regulator. It induces cell division and cell elongation that promotes plant growth.

Definition

ChEBI: 2-Methylindole-3-acetic acid is a member of indole-3-acetic acids.

General Description

2-Methyl-3-indoleacetic acid is a common plant growth hormone. Relative activity of 2-methyl-3-indoleacetic acid in promoting growth (elongation) in plant cells was evaluated.

Synthesis

GENERAL METHOD: Acetylpropionic acid (10 mmol) was dissolved in acetic acid (30 mL) and phenylhydrazine (15 mmol) was added to the solution under stirring conditions. The reaction mixture was heated to reflux for 4 hours. Upon completion of the reaction, it was cooled to room temperature and the mixture was poured into water (200 mL) and the pH was adjusted to 5-6 with 30% sodium hydroxide solution.The precipitated solid was collected by filtration, recrystallized from ethanol and dried under vacuum to give 2-methylindole-3-acetic acid (2a). 2-Methylindole-3-acetic acid (2a): yellow solid, 78% yield, melting point 200-203 °C (literature value 199-200 °C); 1H NMR (500 MHz, CDCl3) δ: 2.31 (3H, s, CH3), 3.65 (2H, s, CH2), 6.97 (1H, t, J = 7.5 Hz, ArH), 7.12 ( 1H, t, J = 7.5 Hz, ArH), 7.23 (1H, d, J = 6.0 Hz, ArH), 7.33 (1H, d, J = 6.0 Hz, ArH), 10.83 (1H, s, COOH), 12.15 (1H, s, NH); IR (νmax, cm-1): 1504, 1518, 1565, 1624, 1769, 2935, 3001, 3535; HRMS m/z: 190.0824 (calculated value C11H11NO2 [M + H]+: 190.0823).

References

[1] Journal of Chemical Research, 2016, vol. 40, # 10, p. 588 - 590

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