methyl 2-(1H-indol-3-yl)acetate

Base Information

• Chemical Name: methyl 2-(1H-indol-3-yl)acetate
• CAS No.: 1912-33-0
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 29339900
• European Community (EC) Number: 217-622-5
• NSC Number: 63806
• UNII: 30TIF5OY0K
• DSSTox Substance ID: DTXSID40172639
• Nikkaji Number: J103.822B
• Wikidata: Q27140143
• Metabolomics Workbench ID: 44026
• ChEMBL ID: CHEMBL4529044
• Mol file: 1912-33-0.mol

Synonyms:1912-33-0;methyl 2-(1H-indol-3-yl)acetate;Methyl indole-3-acetate;Methyl 3-indolylacetate;IAA methyl ester;Indole-3-methyl acetate;Methyl 1H-indol-3-ylacetate;Indole-3-acetic acid, methyl ester;Methyl indol-3-ylacetate;1H-INDOLE-3-ACETIC ACID, METHYL ESTER;Indole-3-acetic acid methyl ester;methyl (indol-3-yl)acetate;methyl IAA;Methyl .beta.-indoleacetate;MeIAA;Methyl 1H-indole-3-acetate;UNII-30TIF5OY0K;.beta.-Indolylacetic acid methyl ester;30TIF5OY0K;EINECS 217-622-5;MFCD00022749;NSC-63806;Methyl 3-indolyacetate;INDOLE-3-ACETIC ACID METHYLESTER;Methyl beta-indoleacetate;Methyl beta-indolylacetate;Methyl beta -indoleacetate;Methyl beta -indolylacetate;NCIOpen2_000050;Methyl .beta.-indolylacetate;SCHEMBL584367;CHEMBL4529044;methyl (1H-indol-3-yl)acetate;Methyl 1H-indol-3-ylacetate #;3-Indoleacetic acid methyl ester;CHEBI:72782;AMY2869;DTXSID40172639;Methylester of 3-Indoleacetic acid;NSC63806;beta-Indolylacetic acid methyl ester;Methyl ester of 3-indoleacetic acid;1H-Indole-3-aceticacid,methyl ester;beta -indolylacetic acid methyl ester;NSC 63806;s6280;AKOS006229746;CS-W015940;FS-3596;HY-W015224;SB15032;1H-indol-3-yl-acetic acid methyl ester;SY014240;(1H-indol-3-yl)-acetic acid methyl ester;INDOLYL-3-ACETIC ACID METHYL ESTER;A4220;FT-0671862;M2605;Methyl indole-3-acetate, >=99.0% (GC);EN300-28648;C20635;I-1140;(1H-INDOL-3-YL)ACETIC ACID METHYL ESTER;Q27140143;Z18279395;Methyl indole-3-acetate, analytical standard, suitable for (for IAA Immunoassay Kit, PGR-3)

Chemical Property of methyl 2-(1H-indol-3-yl)acetate

Chemical Property:

• Appearance/Colour: Dark brown oil
• Vapor Pressure: 7.86E-05mmHg at 25°C
• Melting Point: 50-52 °C
• Refractive Index: 1.622
• Boiling Point: 341.8 °C at 760 mmHg
• PKA: 16.66±0.30(Predicted)
• Flash Point: 160.5 °C
• PSA: 42.09000
• Density: 1.223 g/cm³
• LogP: 1.88340
• Storage Temp.: 2-8°C
• Solubility.: methanol: 0.1 g/mL, clear
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 217

Purity/Quality:

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

Methyl indole-3-acetate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC1=CNC2=CC=CC=C21
• Uses: A phytohormone.

Technology Process of methyl 2-(1H-indol-3-yl)acetate

There total 43 articles about methyl 2-(1H-indol-3-yl)acetate 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: 100.0%

methanesulfonyl chloride (124-63-0) + butan-1-ol (71-36-3) → n-butyl methanesulfonate (1912-32-9)

Guidance literature:

butan-1-ol; With triethylamine; In dichloromethane; at 25 ℃;

methanesulfonyl chloride; In dichloromethane; at 0 - 20 ℃;

Reference yield: 100.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + indole-3-acetic acid (87-51-4) → Indole-3-acetic acid methyl ester (1912-33-0)

Guidance literature:

In diethyl ether; at 20 ℃;

DOI:10.1021/np020375t

Reference yield: 99.0%

methanol (67-56-1) + indole-3-acetic acid (87-51-4) → Indole-3-acetic acid methyl ester (1912-33-0)

Guidance literature:

With thionyl chloride; at -78 - 25 ℃; for 12h;

DOI:10.1021/ol0061642

upstream raw materials:

diazomethane

indole-3-acetic acid

3-[(E)-octa-2,7-dienyl]-1H-indole

indole

Downstream raw materials:

bis-(3-methoxycarbonylmethyl-indol-2-yl)-phenyl-methane

2-(1H-indol-3-yl)-N-phenethyl acetamide

2-(3-indole)-ethanol

indole-3-acetic acid

Refernces

• 1、 Kn?r, Sebastian,Khrenov, Alexey V.,Laufer, Burkhardt,Saenko, Evgueni L.,Hauser, Charlotte A. E.,Kessler, Horst. "Development of a peptidomimetic ligand for efficient isolation and purification of factor VIII via affinity chromatography". . p. 4329 - 4339. Retrieved 2007.
• 2、 Stauffer. "Synthesis of new substituted tryptamines". . p. 1199 - 1203. Retrieved 1966.
• 3、 Kai, Kenji,Wakasa, Kyo,Miyagawa, Hisashi. "Metabolism of indole-3-acetic acid in rice: Identification and characterization of N-β-d-glucopyranosyl indole-3-acetic acid and its conjugates". . p. 2512 - 2522. Retrieved 2007.
• 4、 Eldehna, Wagdy M.,Hassan, Ghada S.,Al-Rashood, Sara T.,Alkahtani, Hamad M.,Almehizia, Abdulrahman A.,Al-Ansary, Ghada H.. "Marine-inspired bis-indoles possessing antiproliferative activity against breast cancer; design, synthesis, and biological evaluation". . . Retrieved 2020.
• 5、 Zhao, Nan,Guan, Ju,Lin, Hong,Chen, Feng. "Molecular cloning and biochemical characterization of indole-3-acetic acid methyltransferase from poplar". . p. 1537 - 1544. Retrieved 2007.
• 6、 -. "Pyridopyrimidinone intermediate ionic derivative containing indole units, and preparation method and application thereof". Paragraph 0047; 0050; 0051. . Retrieved 2021/08/25.
• 7、 Ketsomboon, Nutthanicha,Saeeng, Rungnapha,Sirion, Uthaiwan,Srisook, Klaokwan. "Convenient synthesis of long alkyl-chain triazolylglycosides using ionic liquid as dual promoter-solvent: Readily access to non-ionic triazolylglycoside surfactants for evaluation of cytotoxic activity". . . Retrieved 2021/08/26.