163520-33-0

Basic information

• Product Name: ISOXADIFEN-ETHYL
• Synonyms: ISOXADIFEN-ETHYL;aef122006;isoxadifen-ethyl(bsi,pa iso);ETHYL5,5-DIPHENYL-2-ISOXAZOLINE-3-CARBOXYLATE;Ethyl 4,5-dihydro-5,5-diphenylisoxazol-3-carboxylate;3-Isoxazolecarboxylic acid, 4,5-dihydro-5,5-diphenyl-, ethyl ester;4,5-Dihydro-5,5-diphenyl-3-isoxazolecarboxylic acid ethyl ester;Isoxadifen ethyl ester
• CAS NO: 163520-33-0
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.33
• EINECS: 443-870-0
• Product Categories: herbicide safeners
• Mol File: 163520-33-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 87-88℃ (ethyl ether )
• Boiling Point: 407.7°Cat760mmHg
• Flash Point: 166.8°C
• Appearance: /
• Density: 1.15±0.1 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 7.43E-07mmHg at 25°C
• Refractive Index: 1.576
• Storage Temp.: 0-6°C
• Water Solubility: 1.06mg/L at 20℃
• CAS DataBase Reference: ISOXADIFEN-ETHYL(CAS DataBase Reference)
• NIST Chemistry Reference: ISOXADIFEN-ETHYL(163520-33-0)
• EPA Substance Registry System: ISOXADIFEN-ETHYL(163520-33-0)

Safety Data

• Hazard Codes: Xn,N
• Statements: 22-43-50-50/53
• Safety Statements: 36/37-61-60-22
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: NY2390000
• HazardClass: 9
• PackingGroup: III
• Hazardous Substances Data: 163520-33-0(Hazardous Substances Data)

Usage

Uses

Isoxadifen-ethyl is a particularly useful pesticide.

Definition

ChEBI: An isoxazoline that is the ethyl ester of isoxadifen. It is used as a herbicide safener, especially in conjunction with the herbicides fenoxaprop-P-ethyl and iodosulfuron-methyl-sodium. It is not approved for use within the European Union.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C18H17NO3/c1-2-21-17(20)16-13-18(22-19-16,14-9-5-3-6-10-14)15-11-7-4-8-12-15/h3-12H,2,13H2,1H3

Synthetic route

ethyl 2,2-diphenylcyclopropane-1-carboxylate (67428-04-0, 105561-41-9, 37555-46-7) → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
With trifluoroacetic acid; sodium nitrite at 18 - 40℃; for 0.5h; Reagent/catalyst;	89%

1,1-Diphenylethylene (530-48-3) + nitroacetic acid ethyl ester (626-35-7) → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
With 1,4-diaza-bicyclo[2.2.2]octane In ethanol at 80℃; for 120h;	75%

1,1-Diphenylethylene (530-48-3) + glycine ethyl ester hydrochloride (623-33-6) → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
With tert.-butylnitrite; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; sodium hydrogencarbonate; zinc dibromide In tert-butyl methyl ether at 20℃; for 24h; Schlenk technique; Inert atmosphere; Sealed tube;	67%

ethyl chlorooximidoacetate (95080-93-6) + 1,1-Diphenylethylene (530-48-3) → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
With sodium hydrogencarbonate In isopropyl alcohol at 40℃; for 24h;

benzophenone hydrazone (5350-57-2) → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
Multi-step reaction with 3 steps 1: mercury(II) oxide / Petroleum ether / 16 h / 20 °C 2: Petroleum ether / 0.17 h / 50 °C 3: sodium nitrite; trifluoroacetic acid / 0.5 h / 18 - 40 °C View Scheme

1,1-Diphenylethylene (530-48-3) + ethyl 2-chloro-2-hydroximinoacetate → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
With triethylamine In diethyl ether for 2h;	12.7 g

1,1-Diphenylethylene (530-48-3) + ethyl 2-chloro-2-(hydroxyimino)acetate (14337-43-0) → isoxadifen-ethyl (163520-33-0)

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 25 - 30℃; Temperature;	13 g

isoxadifen-ethyl (163520-33-0) → (5,5-diphenyl-4,5-dihydro-isoxazol-3-yl)-methanol

Conditions	Yield
With sodium tetrahydroborate In ethanol; dichloromethane at 20℃; for 6h;	92%
With sodium tetrahydroborate In methanol for 1h; Heating;

isoxadifen-ethyl (163520-33-0) → 3-chloromethyl-5,5-diphenyl-4,5-dihydro-isoxazole

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / methanol / 1 h / Heating 2: SOCl2 / benzene / 1 h / Heating View Scheme

isoxadifen-ethyl (163520-33-0) → C-(5,5-diphenyl-4,5-dihydro-isoxazol-3-yl)-methylamine (368886-04-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: NaBH4 / methanol / 1 h / Heating 2: SOCl2 / benzene / 1 h / Heating 3: dimethylformamide / 20 °C 4: NH2NH2 / methanol / 2 h / 60 °C View Scheme

isoxadifen-ethyl (163520-33-0) → 2-(5,5-diphenyl-4,5-dihydro-isoxazol-3-ylmethyl)-isoindole-1,3-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: NaBH4 / methanol / 1 h / Heating 2: SOCl2 / benzene / 1 h / Heating 3: dimethylformamide / 20 °C View Scheme

isoxadifen-ethyl (163520-33-0) → 2-allyloxyimino-2-cyano-N-(5,5-diphenyl-4,5-dihydro-isoxazol-3-ylmethyl)-acetamide

Conditions	Yield
Multi-step reaction with 5 steps 1: NaBH4 / methanol / 1 h / Heating 2: SOCl2 / benzene / 1 h / Heating 3: dimethylformamide / 20 °C 4: NH2NH2 / methanol / 2 h / 60 °C 5: Et3N / methanol / 20 °C View Scheme

oct-1-ene (111-66-0) + isoxadifen-ethyl (163520-33-0) → C26H33NO3 + C26H33NO3

Conditions	Yield
With fac-tris(2-(4,6-difluorophenyl)pyridinato,N,C(2'))iridium(III) In acetonitrile at 20℃; Paterno-Buechi Cycloaddition; Irradiation; Sealed tube; Inert atmosphere; Overall yield = 72 percent; regioselective reaction;	A n/a B n/a

Upstream product

• 530-48-3 1,1-Diphenylethylene 
• 626-35-7 nitroacetic acid ethyl ester 
• 67428-04-0 ethyl 2,2-diphenylcyclopropane-1-carboxylate 
• 623-33-6 glycine ethyl ester hydrochloride 
• 14337-43-0 ethyl 2-chloro-2-(hydroxyimino)acetate 
• 5350-57-2 benzophenone hydrazone 
• 95080-93-6 ethyl chlorooximidoacetate 

Downstream Products

• 209866-92-2 4,5-dihydro-5,5-diphenylisoxazole-3-carboxylic acid 
• 368886-04-8 C-(5,5-diphenyl-4,5-dihydro-isoxazol-3-yl)-methylamine 

Relevant articles and documents

Isoxadifen-ethyl with few impurities and preparation method of ethyl isoxadifen-ethyl

The invention relates to isoxadifen-ethyl with low content of impurity compounds shown in a formula (II), a preparation method of the isoxadifen-ethyl, a quantitative method of the compound shown in the formula (II), and application of the compound shown in the formula (II) as a standard substance to control the quality of the isoxadifen-ethyl.

Synthesizing method of isoxadifen-ethyl for industrialized production

The invention provides a synthesizing method of isoxadifen-ethyl for industrialized production. The synthesizing method comprises the following steps of using chlorobenzene as a raw material, using tetrahydrofuran as a solvent, and reacting with magnesium, so as to obtain a phenyl magnesium chloride Grignard reagent; performing nucleophilic addition reaction with acetophenone to generate 1,1-diphenylethanol; adding p-toluenesulfonic acid to dewater, so as to generate 1,1-diphenylethene; reacting with ethyl 2-chloro-2-(hydroxyimino)acetate, so as to generate an isoxadifen-ethyl product, whereinthe purity can reach 99%.

PROCESS FOR PRODUCING ISOXAZOLINE DERIVATIVES

A process for producing isoxazoline derivatives by ring-opening and cyclization of the corresponding cyclopropane derivatives with electrophilic nitrosylation reagents.