2-(5-methyl-1H-indol-3-yl)acetic acid

Base Information

• Chemical Name: 2-(5-methyl-1H-indol-3-yl)acetic acid
• CAS No.: 1912-47-6
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 2933998090
• NSC Number: 21428
• DSSTox Substance ID: DTXSID80281370
• Nikkaji Number: J775.401I
• Wikidata: Q72491857
• ChEMBL ID: CHEMBL81944
• Mol file: 1912-47-6.mol

Synonyms:1912-47-6;2-(5-methyl-1H-indol-3-yl)acetic acid;5-METHYLINDOLE-3-ACETIC ACID;(5-Methyl-1H-indol-3-yl)-acetic acid;1h-indole-3-acetic acid, 5-methyl-;5-Methylindol-3-ylacetic acid;MFCD00022751;NSC21428;CHEMBL81944;SCHEMBL6116786;DTXSID80281370;5-Methyl-1H-indole-3-acetic acid;BCP27600;NSC 21428;NSC-21428;AKOS005259105;(5-methyl-1H-indol-3-yl)acetic acid;SB34715;DS-11879;SY012013;2-(5-methyl-1H-indol-3-yl)ethanoic acid;BB 0254999;CS-0130267;FT-0620623;F15948;M-3974;EN300-1635714;A815726;Z1138836786

Chemical Property of 2-(5-methyl-1H-indol-3-yl)acetic acid

Chemical Property:

• Melting Point: 151 °C
• Boiling Point: 420.8 °C at 760 mmHg
• PKA: 4.53±0.30(Predicted)
• Flash Point: 208.3 °C
• PSA: 53.09000
• Density: 1.299 g/cm³
• LogP: 2.10340
• Storage Temp.: 2-8°C
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 229

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Methylindole-3-aceticAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2=C(C=C1)NC=C2CC(=O)O
• Uses: 5-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.

Technology Process of 2-(5-methyl-1H-indol-3-yl)acetic acid

There total 9 articles about 2-(5-methyl-1H-indol-3-yl)acetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(5-methyl-indol-3-yl)-acetic acid methyl ester (1337870-84-4) → 2-(5-methyl-1H-indol-3-yl)acetic acid (1912-47-6)

Guidance literature:

With water; lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 16h;

Reference yield: 81.0%

→ 2-(5-methyl-1H-indol-3-yl)acetic acid (1912-47-6)

Guidance literature:

With morpholine; sulfur; at 120 ℃; for 8h;

With sodium hydroxide; In ethanol; for 4h; Reflux;

Reference yield:

5-methyl-1H-indole (614-96-0) → 2-(5-methyl-1H-indol-3-yl)acetic acid (1912-47-6)

Guidance literature:

Multi-step reaction with 4 steps

1: diethyl ether / 0.33 h / 0 °C

2: sat. aq. NaHCO₃ / diethyl ether / 0.5 h / Heating

3: methanol / 8 h / Heating

4: NaBH₄ / tetrahydrofuran / 10 h / Heating

With sodium tetrahydroborate; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4039(00)76815-8

upstream raw materials:

Succinic semialdehyde

N-4-methylphenylhydrazine

5-methyl-1H-indole

2-(5-methyl-1H-indol-3-yl)-2-oxoacetyl chloride

Downstream raw materials:

2-(1-(benzyloxycarbonyl)-5-methyl-1H-indol-3-yl)acetic acid

N-benzyl-2-(1,5-dimethyl-1H-indol-3-yl)acetamide

C₁₈H₁₈N₂O

5-methyl-1H-indole-3-acetic acid ethyl e

Refernces

• 1、 -. "TETRAHYDROISOQUINOLINE COMPOUND, PREPARATION METHOD THEREFOR, PHARMACEUTICAL COMPOSITION CONTAINING SAME, AND USE THEREOF". . . Retrieved 2020/12/22.
• 2、 Zhu, Shaolin,MacMillan, David W. C.. "Enantioselective copper-catalyzed construction of aryl pyrroloindolines via an arylation-cyclization cascade". . p. 10815 - 10818. Retrieved 2012/08/07.