96525-23-4

Basic information

• Product Name: FLURTAMONE
• Synonyms: (+-)-3(2h)-furanon;(+-)-5-(methylamino)-2-phenyl-4-(3-(trifluoromethyl)phenyl)-3(2h)-furanone;benchmark;BACARA;FLURTAMONE;(±)-5-(methylamino)-2-pheny-4-(3-(triflurormethyl)phenyl)-3(2H)-furanone;(RS)-5-methylamino-2-phenyl-4-(α,α,α-trifluoro-m-tolyl)furan-3(2H)-one;FLURTAMONE 97 % (HPLC, EFFEKTIV)
• CAS NO: 96525-23-4
• Molecular Formula: C₁₈H₁₄F₃NO₂
• Molecular Weight: 333.3
• Product Categories: Alpha sort;E-GAlphabetic;F;FA - FLPesticides&Metabolites;Herbicides;Others;Pesticides&Metabolites
• Mol File: 96525-23-4.mol
• Article Data: 3

Chemical Properties

• Melting Point: 152.5℃
• Boiling Point: 446.2 °C at 760 mmHg
• Flash Point: 223.6 °C
• Appearance: /
• Density: 1.38 mg/m3
• Vapor Pressure: 3.73E-08mmHg at 25°C
• Refractive Index: 1.576
• PKA: 2.97±0.40(Predicted)
• BRN: 7543933
• CAS DataBase Reference: FLURTAMONE(CAS DataBase Reference)
• NIST Chemistry Reference: FLURTAMONE(96525-23-4)
• EPA Substance Registry System: FLURTAMONE(96525-23-4)

Safety Data

• Hazard Codes: N
• Statements: 50/53
• Safety Statements: 60-61
• RIDADR: UN3077 9/PG 3
• WGK Germany: 2
• RTECS: LU5105000
• Hazardous Substances Data: 96525-23-4(Hazardous Substances Data)

Usage

Uses

Herbicide.

InChI:InChI=1/C18H14F3NO2/c1-22-17-14(12-8-5-9-13(10-12)18(19,20)21)15(23)16(24-17)11-6-3-2-4-7-11/h2-10,16,22H,1H3

Synthetic route

2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran (96525-22-3) + N-benzyl-N,N,N-triethylammonium chloride (56-37-1) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
With sodium hydroxide; dimethyl sulfate In dichloromethane; water

2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran (96525-22-3) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
With methylamine In tetrahydrofuran; methanol; water
With hydrogenchloride In methanol; water; methylamine

2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran (96525-22-3) + dimethyl sulfate (77-78-1) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
With trimethyldodecylammonium chloride; sodium sulfite In water; 1,2-dichloro-ethane at 20℃; for 2.5h; Reagent/catalyst; Large scale;

3-trifluoromethylphenylacetonitrile (2338-76-3) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 16 h / 25 °C / Large scale 2: bromine / methanol / 13 h / 20 °C / Large scale 3: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / 1,2-dichloro-ethane; water / 3.5 h / 20 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 16 h / 25 °C / Large scale 2: bromine / methanol / 13 h / 20 °C / Large scale 3: sodium sulfite; trimethyldodecylammonium chloride / 1,2-dichloro-ethane; water / 2.5 h / 20 °C / Large scale View Scheme

Ethyl 2-phenylethanoate (101-97-3) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 16 h / 25 °C / Large scale 2: bromine / methanol / 13 h / 20 °C / Large scale 3: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / 1,2-dichloro-ethane; water / 3.5 h / 20 °C / Large scale View Scheme
Multi-step reaction with 3 steps 1: sodium methylate / methanol / 16 h / 25 °C / Large scale 2: bromine / methanol / 13 h / 20 °C / Large scale 3: sodium sulfite; trimethyldodecylammonium chloride / 1,2-dichloro-ethane; water / 2.5 h / 20 °C / Large scale View Scheme

(3-trifluoromethylphenyl)benzylcarbonylacetonitrile (68084-26-4) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: bromine / methanol / 13 h / 20 °C / Large scale 2: N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide / 1,2-dichloro-ethane; water / 3.5 h / 20 °C / Large scale View Scheme

2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran (96525-22-3) + carbonic acid dimethyl ester (616-38-6) → 2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water; 1,2-dichloro-ethane at 20℃; for 3.5h; Reagent/catalyst; Large scale;

2-Phenyl-3-oxo-4-(-3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran (96525-23-4) → Lithium salt of 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-methylamino-2,3-dihydrofuran

Conditions	Yield
With n-butyllithium In tetrahydrofuran; hexane

Upstream product

• 96525-22-3 2-phenyl-3-oxo-4-(3-trifluoromethylphenyl)-5-amino-2,3-dihydrofuran 
• 77-78-1 dimethyl sulfate 
• 2338-76-3 3-trifluoromethylphenylacetonitrile 
• 101-97-3 Ethyl 2-phenylethanoate 
• 68084-26-4 (3-trifluoromethylphenyl)benzylcarbonylacetonitrile 
• 616-38-6 carbonic acid dimethyl ester 
• 56-37-1 N-benzyl-N,N,N-triethylammonium chloride 

Relevant articles and documents

[...] method for the production of efficient herbicide (by machine translation)

The invention discloses an efficient method of producing herbicide [...], to trifluoromethyl benzene b nitrile and benzene acetic acid ethyl ester as the main raw material, the claisen condensation, cyclization under in an acidic solvent, methylation three steps [...] the target product can be obtained. The present invention has higher safety, for reaction and purification conditions is relatively low, it is relatively easy to separate, and is not easy to generate discharge of waste acid, the solvent can be recycled, the production yield is higher. This method is more suitable for the industrial production of [...], [...] is more favorable for the wide application of efficient herbicide. (by machine translation)

Herbicidal 5-amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof

5-Amino-3-oxo-4-(substituted-phenyl)-2,3-dihydrofuran and derivatives thereof. The compounds generally exhibit both pre-emergence and post-emergence phytotoxicity and are useful as herbicides and also at low dosages as plant growth regulating agents.