Indole-3-butyric acid

Base Information

• Chemical Name: Indole-3-butyric acid
• CAS No.: 133-32-4
• Deprecated CAS: 111150-79-9,65216-51-5,65216-51-5
• Molecular Formula: C12H13NO2
• Molecular Weight: 203.241
• Hs Code.: Oral mouse LD50: 100 mg/Kg
• European Community (EC) Number: 205-101-5
• NSC Number: 3130
• UNII: 061SKE27JP
• DSSTox Substance ID: DTXSID8032623
• Nikkaji Number: J2.525I
• Wikipedia: Indole-3-butyric acid
• Wikidata: Q2622539
• NCI Thesaurus Code: C63656
• Metabolomics Workbench ID: 38018
• ChEMBL ID: CHEMBL582878
• Mol file: 133-32-4.mol

Synonyms:1H-indole-3-butanoic acid;3-indolebutyric acid;indole-3-butyric acid;indolebutyric acid;indolebutyric acid, monoammonium salt;indolebutyric acid, monopotassium salt;indolebutyric acid, monosodium salt

Chemical Property of Indole-3-butyric acid

Chemical Property:

• Appearance/Colour: white to light yellow crystalline powder
• Vapor Pressure: 4.9E-08mmHg at 25°C
• Melting Point: 124-125.5 °C(lit.)
• Refractive Index: 1.5440 (estimate)
• Boiling Point: 426.562 °C at 760 mmHg
• PKA: 4.83±0.10(Predicted)
• Flash Point: 211.777 °C
• PSA: 53.09000
• Density: 1.252 g/cm³
• LogP: 2.57520
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• Water Solubility.: Soluble in water(0.25g/L).
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 203.094628657
• Heavy Atom Count: 15
• Complexity: 230

Purity/Quality:

98%, ^*data from raw suppliers

Indole-3-butyric acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T,Xi
• Hazard Codes: T,Xi
• Statements: 25-36/37/38
• Safety Statements: 26-36-45-38-36/37/39-28A

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Pesticides -> Plant Growth Regulators
• Canonical SMILES: C1=CC=C2C(=C1)C(=CN2)CCCC(=O)O
• Uses: Indole butyric acid (IBA) is a broad spectrum indole-class plant growth regulators and is a good rooting agent. It can promote the cuttings and rooting of herbaceous and woody ornamental plant. It can also be applied to the fruit setting of fruit as well as improving the fruit setting rate. Used to stimulate root formation of plant clippings. Suitable for plant cell culture tested. Indole-3-butyric acid is auxin-family plant hormone (phytohormone). IBA is thought to be a precursor of indole-3-acetic acid (IAA) the most abundant and the basic auxin natively occurring and functioning in plants. IAA generates the majority of auxin effects in intact plants, and is the most potent native auxin.

Technology Process of Indole-3-butyric acid

There total 15 articles about Indole-3-butyric 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: 90.0%

4-butanolide (96-48-0) + indole (120-72-9) → 4-indol-3-yl-butyric acid (133-32-4)

Guidance literature:

With Na-NaOH/γ-Al₂O₃; polyethylene glycol; In tetralin; at 210 ℃; for 5h;

Reference yield: 79.0%

3-allylindole (16886-09-2) + formic acid (64-18-6) → 4-indol-3-yl-butyric acid (133-32-4)

Guidance literature:

With palladium diacetate; acetic anhydride; P(p-C₆H₄F)3; In toluene; at 80 ℃; for 48h; Inert atmosphere; Sealed tube;

Reference yield:

4-(3-indolyl)butanenitrile (59108-95-1) → 4-indol-3-yl-butyric acid (133-32-4)

Guidance literature:

With potassium hydroxide;

upstream raw materials:

4-(3-indolyl)butanenitrile

1-hydroxy-carbazole-2-carboxylic acid

4-(2-carboxy-indol-3-yl)-butyric acid

5-(2-amino-phenyl)-6-chloro-hex-5-enoic acid

Downstream raw materials:

4-(2-Formamidobenzoyl)buttersaeure

1-<4-(3-indolyl)butanoyl>-1,2,3,6-tetrahydro-4-phenylpyridine

1-[4-(4-Fluoro-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-4-(1H-indol-3-yl)-butan-1-one

4-(1H-Indol-3-yl)-1-[4-(4-methoxy-phenyl)-3,6-dihydro-2H-pyridin-1-yl]-butan-1-one

Refernces

Substituted benzylaminoalkylindoles with preference for the σ₂ binding site

10.1016/j.ejmech.2007.09.012

The research aimed to develop new ligands with high affinity and selectivity for the s receptors, specifically focusing on the s2 subtype. The study synthesized a series of N-benzyl-3-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylpropan-1-amines and N-benzyl-4-[1-(4-fluorophenyl)-1H-indol-3-yl]-N-methylbutan-1-amines with various substitutions on the phenyl ring. The key chemicals used included 3(1H-indol-3-yl)propanoic acid, 4-(1H-indol-3-yl)butanoic acid, LiAlH4 for reduction, 4-bromofluorobenzene for coupling, methanesulfonyl chloride for esterification, and various substituted benzylamines for final derivatization. The results indicated that phenyl substituents positively modulated the ability of these compounds to displace [3H]-DTG from s2 sites, while reducing displacement from s1 sites. The butylene derivatives showed greater binding affinity for s2 over s1 receptors, with the 2,4-dimethyl substituted butylene derivative (2l) exhibiting the highest s2 affinity (s2Ki = 5.9 nM) and selectivity (s1Ki/s2Ki = 22). The study concluded that a butylene chain separating the indole moiety from variously substituted benzylamino groups is crucial for interaction with the s2 binding site, suggesting that these structural features could be leveraged to design new s2 selective ligands with potential therapeutic applications.