Methoxybrassinin

Base Information

• Chemical Name: Methoxybrassinin
• CAS No.: 105748-60-5
• Molecular Formula: C12H14 N2 O S2
• Molecular Weight: 266.388
• DSSTox Substance ID: DTXSID90909715
• Nikkaji Number: J391.782G
• Wikidata: Q27107341
• Metabolomics Workbench ID: 46005
• ChEMBL ID: CHEMBL2442575
• Mol file: 105748-60-5.mol

Synonyms:Methoxybrassinin;105748-60-5;1-METHOXYBRASSININ;N-Methoxybrassinin;methyl N-[(1-methoxyindol-3-yl)methyl]carbamodithioate;CHEBI:6841;Methyl ((1-methoxy-1H-indol-3-yl)methyl)carbamodithioate;Carbamodithioic acid, ((1-methoxy-1H-indol-3-yl)methyl)-, methyl ester;Carbamodithioic acid, N-[(1-methoxy-1H-indol-3-yl)methyl]-, methyl ester;starbld0003742;C08506;CHEMBL2442575;SCHEMBL20138481;DTXSID90909715;AKOS040748910;Q27107341;N-[(1-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide;Methyl hydrogen [(1-methoxy-1H-indol-3-yl)methyl]carbonodithioimidate

Chemical Property of Methoxybrassinin

Chemical Property:

• Vapor Pressure: 2.33E-07mmHg at 25°C
• Boiling Point: 422.9°Cat760mmHg
• Flash Point: 209.6°C
• PSA: 90.62000
• Density: 1.25g/cm³
• LogP: 2.84850
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 266.05475542
• Heavy Atom Count: 17
• Complexity: 275

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CON1C=C(C2=CC=CC=C21)CNC(=S)SC

Technology Process of Methoxybrassinin

There total 18 articles about Methoxybrassinin 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:

(1-methoxyindol-3-yl)methylamine (132169-26-7) → 1-methoxybrassinin (105748-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N; pyridine / 1 h / 0 °C

2: 199 mg / Et₃N; pyridine / 16 h / 5 °C

With pyridine; triethylamine; 1: Addition / 2: Methylation;

DOI:10.1016/S0031-9422(00)00277-6

Reference yield:

(1-Methoxy-1H-indol-3-ylmethyl)-dithiocarbamic acid + methyl iodide (74-88-4) → 1-methoxybrassinin (105748-60-5)

Guidance literature:

Yield given;

DOI:10.3987/COM-91-S20

Reference yield:

1-methoxyindole-3-carboxaldehyde oxime (69111-61-1) → 1-methoxybrassinin (105748-60-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 188 mg / TiCl₃; NaBH₃CN; NH₄OAc / methanol / 0.25 h / 0 °C

2: Et₃N; pyridine / 1 h / 0 °C

3: 199 mg / Et₃N; pyridine / 16 h / 5 °C

With pyridine; titanium(III) chloride; ammonium acetate; sodium cyanoborohydride; triethylamine; In methanol; 1: Reduction / 2: Addition / 3: Methylation;

DOI:10.1016/S0031-9422(00)00277-6

upstream raw materials:

methylthiol

1-methoxyindolyl-3-methyl isothiocyanate

methyl iodide

1-methoxy-3-indolylmethyl glucosinolate

Downstream raw materials:

1-benzoyl-1H-indole-3-carbaldehyde

Refernces

• 1、 Budovska, Mariana. "A novel palladium-catalyzed cyclization of indole phytoalexin brassinin and its 1-substituted derivatives". . p. 5575 - 5582. Retrieved 2014.
• 2、 Agerbirk, Niels,Olsen, Carl Erik,Sorensen, Hilmer. "Initial and Final Products, Nitriles, and Ascorbigens Produced in Myrosinase-Catalyzed Hydrolysis of Indole Glucosinolates". . p. 1563 - 1571. Retrieved 2007/10/03.