Brassinin

Base Information

• Chemical Name: Brassinin
• CAS No.: 105748-59-2
• Molecular Formula: C11H12N2S2
• Molecular Weight: 236.362
• Hs Code.: 2933990090
• UNII: J2IBO1B8VH
• DSSTox Substance ID: DTXSID30909714
• Nikkaji Number: J391.783E
• Wikidata: Q27117380
• NCI Thesaurus Code: C63657
• Metabolomics Workbench ID: 46004
• ChEMBL ID: CHEMBL373777
• Mol file: 105748-59-2.mol

Synonyms:brassinin;methyl N-(1H-indol-3-ylmethyl)carbamodithioate

Chemical Property of Brassinin

Chemical Property:

• Vapor Pressure: 7.8E-08mmHg at 25°C
• Melting Point: 132-133 ºC
• Refractive Index: 1.732
• Boiling Point: 436.899 °C at 760 mmHg
• Flash Point: 218.029 °C
• PSA: 85.21000
• Density: 1.321 g/cm³
• LogP: 3.29630
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 236.04419074
• Heavy Atom Count: 15
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

Brassinin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CSC(=S)NCC1=CNC2=CC=CC=C21
• Uses: A biosynthetic precursor of Brassilexin Brassinin is a plant metabolite of great significance due to its dual role both as an effective phytoalexin and as an early biosynthetic precursor of the majority of the phytoalexins produced by plants of the family Brassicaceae (Cruciferae).

Technology Process of Brassinin

There total 15 articles about Brassinin 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%

carbon disulfide (75-15-0,12122-00-8) + 3-aminomethylindole (22259-53-6) + methyl iodide (74-88-4) → brassinin (105748-59-2)

Guidance literature:

carbon disulfide; 3-aminomethylindole; With pyridine; triethylamine; at 0 ℃; for 0.333333h;

methyl iodide; at 0 ℃; for 0.5h;

DOI:10.1016/j.bmc.2006.03.014

Reference yield: 92.0%

1-(tert-butoxycarbonyl)brassinin (188988-50-3) → brassinin (105748-59-2)

Guidance literature:

With piperidine; 15-crown-5; sodium thiomethoxide; In acetonitrile; for 1.41667h; Ambient temperature;

DOI:10.1055/s-1997-761

Reference yield:

indol-3-ylmethyl isothiocyanate + sodium thiomethoxide (5188-07-8) → phenethylbrassinin (16022-44-9) + brassinin (105748-59-2)

Guidance literature:

With phosphate buffer; In water; for 0.0833333h; Ambient temperature;

DOI:10.1021/ja00094a021

upstream raw materials:

carbon disulfide

3-aminomethylindole

methyl iodide

sodium thiomethoxide

Downstream raw materials:

cyclobrassinin

S-methyl dithiocarbamate

Indole-3-carboxaldehyde

Refernces

• 1、 Zhong, Xin,Chen, Ning,Xu, Jiaxi. "A concise synthesis of cyclobrassinin and its analogues via a thiyl radical aromatic substitution". supporting information. p. 13549 - 13557. Retrieved 2018/08/21.
• 2、 -. "Novel IDO inhibitors and methods of use thereof". Page/Page column Sheet 2/7; 7. . Retrieved 2010/11/27.