Florasulam

Base Information

• Chemical Name: Florasulam
• CAS No.: 145701-23-1
• Molecular Formula: C12H8F3N5O3S
• Molecular Weight: 359.288
• UNII: 00A64ZX8NB
• ChEMBL ID: CHEMBL3185236
• DSSTox Substance ID: DTXSID7044340
• Metabolomics Workbench ID: 155414
• Nikkaji Number: J1.388.962G
• Wikidata: Q22807578
• Mol file: 145701-23-1.mol

Synonyms:florasulam;N-(2,6-difluorophenyl)-5-methoxy-8-fluoro-(1,2,4)-triazolo-(1,5c)-pyrimidine-2-sulfonamide

Chemical Property of Florasulam

Chemical Property:

• Melting Point: 220-221° (dec) (Van Heertum); also reported as 193.5-230.5° (Thompson)
• Refractive Index: 1.676
• PKA: 4.54(at 25℃)
• PSA: 106.86000
• Density: 1.757 g/cm³
• LogP: 2.50480
• Storage Temp.: 0-6°C
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 359.02999479
• Heavy Atom Count: 24
• Complexity: 541

Purity/Quality:

99% ^*data from raw suppliers

Florasulam ^*data from reagent suppliers

Safty Information:

• Pictogram(s): N
• Hazard Codes: N:
• Statements: R50/53:
• Safety Statements: S60-61:

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC1=NC=C(C2=NC(=NN21)S(=O)(=O)NC3=C(C=CC=C3F)F)F
• Description: Florasulam is a kind of selective triazolopyrimidine sulfonanilide post-emergent herbicide. It is absorbed by the foliage or roots of the plants. It acts as a systemic herbicide, being able to disrupt the internal growth processes of the weeds and causes their death in several weeks. It can be used for the control of broadleaf weeds in cereals. Its mechanism of action is through inhibiting the acetolactate synthase (ALS) in plants. The enzyme is present in the chloroplast and participates into the biosynthesis of branch chain amino acids such as valine, leucine and isoleucine. Through this mechanism, it can suppress plant cell division, plant growth and ultimately cause plant death.
• Uses: Herbicide.

Technology Process of Florasulam

There total 4 articles about Florasulam 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: 94.2%

2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine (147150-78-5) + 2,6-difluoroaniline (5509-65-9) → florasulam (145701-23-1)

Guidance literature:

2,6-difluoroaniline; With N-chloro-succinimide; dimethylsulfide; In acetonitrile; at -20 ℃; Inert atmosphere;

2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine; With 3-Methylpyridine; In acetonitrile; at 20 - 40 ℃; Temperature; Inert atmosphere;

Reference yield:

propylene glycol (57-55-6,63625-56-9) + 2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine (147150-78-5) → florasulam (145701-23-1)

Guidance literature:

In dichloromethane; water;

Reference yield:

2-methoxy-4-chloro-5-fluoropyrimidine (1801-06-5) → florasulam (145701-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ethanol / 6 h / Reflux

1.2: 3 h / 10 °C / pH 10 - 11

2.1: sodium nitrite; hydrogenchloride / water / 4 h / 0 °C

2.2: 4 h / 10 - 15 °C

3.1: propylene glycol / dichloromethane / 20 °C

3.2: 5 h / 40 °C

With hydrogenchloride; propylene glycol; sodium nitrite; In ethanol; dichloromethane; water;

upstream raw materials:

2-chlorosulfonyl-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine

2,6-difluoroaniline

propylene glycol

2-methoxy-4-chloro-5-fluoropyrimidine

Refernces

• 1、 -. "Method for preparing florasulam". Paragraph 0019-0032. . Retrieved 2019/12/25.
• 2、 -. "PREPARATION OF N-ARYLARYLSULFONAMIDE COMPOUNDS". Page/Page column 6. . Retrieved 2008/06/13.