Irgarol

Base Information

• Chemical Name: Irgarol
• CAS No.: 28159-98-0
• Molecular Formula: C11H19N5S
• Molecular Weight: 253.371
• Hs Code.: 29336990
• European Community (EC) Number: 248-872-3
• UNII: E7B77O21GH
• DSSTox Substance ID: DTXSID3032416
• Nikkaji Number: J135.024B
• Wikidata: Q1147281
• Metabolomics Workbench ID: 53232
• ChEMBL ID: CHEMBL3185551
• Mol file: 28159-98-0.mol

Synonyms:1,3,5-Triazine-2,4-diamine,N-cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)- (9CI);Cybutrin;Cybutryne;Irgaguard A 2000;Irgarol 1051;Irgarol 1071;Microban Additive IA 1;N-Cyclopropyl-N'-(1,1-dimethylethyl)-6-(methylthio)-1,3,5-triazine-2,4-diamine;Nuocide 1051;s-Triazine,2-(tert-butylamino)-4-(cyclopropylamino)-6-(methylthio)- (8CI);2-(Methylthio)-4-(tert-butylamino)-6-(cyclopropylamino)-s-triazine;2-(tert-Butylamino)-4-(cyclopropylamino)-6-(methylthio)-1,3,5-triazine;2-(tert-Butylamino)-4-(cyclopropylamino)-6-(methylthio)-s-triazine;

Chemical Property of Irgarol

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 128-133 °C
• Boiling Point: 427.971 °C at 760 mmHg
• PKA: 4.13±0.10(Predicted)
• Flash Point: 212.629 °C
• PSA: 88.03000
• Density: 1.202 g/cm³
• LogP: 2.52420
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Water Solubility.: Insoluble in water
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 253.13611680
• Heavy Atom Count: 17
• Complexity: 251

Purity/Quality:

99% ^*data from raw suppliers

Irgarol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,N
• Hazard Codes: Xi;N,N,Xi
• Statements: 43-50/53
• Safety Statements: 36/37-60-61

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)NC1=NC(=NC(=N1)NC2CC2)SC
• Uses: Irgarol is a highly specific and effective inhibitor of photosynthesis. This makes it ideal, combined with its very low water solubility, for use in long-life antifouling coatings for marine applicati ons to prevent the growth of algae. Booster algicide in antifouling paint. Photosystem-II (PSII) herbicide; inhibits photosynthetic electron transport in chloroplasts

Technology Process of Irgarol

There total 3 articles about Irgarol 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: 97.9%

→ 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0)

Guidance literature:

Reference yield: 93.0%

N2-tert-butyl-6-chloro-N4-cyclopropyl-1,3,5-triazine-2,4-diamine (26737-71-3) + carbonic acid dimethyl ester (616-38-6) → 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0)

Guidance literature:

With potassium tert-butylate; palladium diacetate; triphenylphosphine; potassium thioacetate; In dimethyl sulfoxide; at 120 ℃; Inert atmosphere;

Reference yield:

tert-butyl-(4-chloro-6-methylsulfanyl-[1,3,5]triazin-2-yl)-amine (4622-80-4) + Cyclopropylamine (765-30-0) → 2-methylthio-4-t-butylamino-6-cyclopropyl-amino-s-triazine (28159-98-0)

Guidance literature:

With sodium hydroxide; In toluene;

upstream raw materials:

tert-butyl-(4-chloro-6-methylsulfanyl-[1,3,5]triazin-2-yl)-amine

Cyclopropylamine

N²-tert-butyl-6-chloro-N⁴-cyclopropyl-1,3,5-triazine-2,4-diamine

carbonic acid dimethyl ester

Downstream raw materials:

2-methylthio-4-tert-butylamino-6-amino-s-triazine

Refernces

• 1、 -. "Methyl aryl thioether compound, and synthetic method and applications thereof". Paragraph 0188; 0189; 0190. . Retrieved 2017/07/21.
• 2、 -. "Agent for combating sea-water algae". . . Retrieved 2008/06/13.