| Identification | More | [Name]
2-METHYLINDOLE-3-ACETIC ACID | [CAS]
1912-43-2 | [Synonyms]
(2-METHYL-1H-INDOL-3-YL)-ACETIC ACID
2-METHYL-3-INDOLEACETIC ACID
2-METHYLINDOLE-3-ACETIC ACID
AKOS BC-0002
IFLAB-BB F0345-1687
2-METHYLINDOLE-3-ACETIC ACID, 98+%
2-Me-IAA | [EINECS(EC#)]
-0 | [Molecular Formula]
C11H11NO2 | [MDL Number]
MFCD00075006 | [Molecular Weight]
189.21 | [MOL File]
1912-43-2.mol |
| Chemical Properties | Back Directory | [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 | [InChI]
1S/C11H11NO2/c1-7-9(6-11(13)14)8-4-2-3-5-10(8)12-7/h2-5,12H,6H2,1H3,(H,13,14) | [InChIKey]
QJNNHJVSQUUHHE-UHFFFAOYSA-N | [SMILES]
Cc1[nH]c2ccccc2c1CC(O)=O | [CAS DataBase Reference]
1912-43-2(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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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