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80844-07-1

Basic Information
CAS No.: 80844-07-1
Name: Ethofenprox
Article Data: 8
Molecular Structure:
Molecular Structure of 80844-07-1 (Ethofenprox)
Formula: C25H28O3
Molecular Weight: 376.496
Synonyms: 2-(4-Ethoxyphenyl)-2-methylpropyl3-phenoxybenzyl ether;4-Ethoxyneophyl 3-phenoxybenzyl ether;Ethophenprox;Ethoproxyfen;Ethoproxyphen;Etof;Etofenprox;MTI 500;SA130301;Trebon;Ethofenprox;
EINECS: 407-980-2
Density: 1.1±0.1 g/cm3
Melting Point: 36oC
Boiling Point: 481.6±40.0 °C at 760 mmHg
Flash Point: 165.1±24.6 °C
Solubility: <0.001 mg l-1(25 °C)
Appearance: white solid
PSA: 27.69000
LogP: 6.37200
Synthetic route
51632-16-7

3-phenoxybenzyl bromide

83493-63-4

2-(4-ethoxyphenyl)-2,2-dimethylethanol

80844-07-1

etofenprox

Conditions
ConditionsYield
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 0.583333h; Irradiation;95%

(m-phenoxyphenyl)methyl chlorosulfite

83493-63-4

2-(4-ethoxyphenyl)-2,2-dimethylethanol

80844-07-1

etofenprox

Conditions
ConditionsYield
at 50℃; for 2h;93%
75-03-6

ethyl iodide

80854-21-3

3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether

80844-07-1

etofenprox

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 0 - 25℃; for 14h; Inert atmosphere;86%
13826-35-2

3-Phenoxybenzyl alcohol

83493-80-5

4-(2'-chloro-1',1'-dimethylethyl)ethoxybenzene

A

80844-07-1

etofenprox

B

80854-21-3

3-phenoxybenzyl 2-(4-hydroxyphenyl)-2-methylpropyl ether

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide at 110 - 120℃; for 15h;A 42.5%
B 8.5%
51632-16-7

3-phenoxybenzyl bromide

2-methyl-2-(m-/p-ethoxyphenyl)-1-propanol

2-methyl-2-(m-/p-ethoxyphenyl)-1-propanol

A

80844-07-1

etofenprox

B

2-Methyl-2-(m-ethoxyphenyl)propyl m-(phenoxy)benzyl ether

Conditions
ConditionsYield
With potassium hydroxide; tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 8h;
515-40-2

neophyl chloride

80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / HNO3; H2SO4
2: 67 percent / K2CO3 / acetone / 15 h / 40 °C
3: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
99359-77-0

1-chloro-2-methyl-2-(4-nitrophenyl)propane

80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 67 percent / K2CO3 / acetone / 15 h / 40 °C
2: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
103-73-1

Phenetole

80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: H2SO4 / 5 h / 20 °C
2: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
71-43-2

benzene

1,x-dichloro-octane

1,x-dichloro-octane

80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 96 percent / H2SO4
2: 91 percent / HNO3; H2SO4
3: 67 percent / K2CO3 / acetone / 15 h / 40 °C
4: 42.5 percent / KOH / dimethylsulfoxide / 15 h / 110 - 120 °C
View Scheme
57225-86-2

methyl 2-(4-chlorophenyl)-2-methylpropanoate

80844-07-1

etofenprox

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere
2: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere
3: potassium hydroxide; tris-(dibenzylideneacetone)dipalladium(0); tert-butyl XPhos / water; 1,4-dioxane / 16 h / 100 - 115 °C / Inert atmosphere
4: potassium carbonate / N,N-dimethyl-formamide / 14 h / 0 - 25 °C / Inert atmosphere
View Scheme
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Specification

The Etofenprox, with the CAS registry number 80844-07-1, is also known as 4-Ethoxyneophyl 3-phenoxybenzyl ether. Its EINECS number is 407-980-2. This chemical's molecular formula is C25H28O3 and molecular weight is 376.49. What's more, its systematic name is 1-{[2-(4-Ethoxyphenyl)-2-methylpropoxy]methyl}-3-phenoxybenzene. This chemical should be sealed and stored in a cool and dry place. It is incompatible with strong oxidizing agents. Its classification codes are: (1)Acaricide; (2)Agricultural Chemical; (3)Insecticide; (4)Reproductive Effect. This chemical is used as a pesticide of broad-spectrum, high effective, low toxic, less residual and it is safe to crop. It is synthetic pyrethroid for insecticidal efficacy against mosquito larvae & on non-target organisms. 

Physical properties of Etofenprox are: (1)ACD/LogP: 7.34±0.52 # of Rule of 5 Violations: 1; (2)ACD/LogD (pH 5.5): 7.35 ACD/LogD (pH 7.4): 7.35; (3)ACD/BCF (pH 5.5): 225191.00; (4)ACD/BCF (pH 7.4): 225191.00; (5)ACD/KOC (pH 5.5): 236010.60; (6)ACD/KOC (pH 7.4): 236010.60; (7)#H bond acceptors: 3; (8)#H bond donors: 0; (9)#Freely Rotating Bonds: 9; (10)Polar Surface Area: 27.69 Å2; (11)Index of Refraction: 1.559; (12)Molar Refractivity: 113.3±0.3 cm3; (13)Molar Volume: 350.8±3.0 cm3; (14)Polarizability: 44.9±0.5×10-24cm3; (15)Surface Tension: 38.6±3.0 dyne/cm; (16)Density: 1.1±0.1 g/cm3; (17)Flash Point: 165.1±24.6 °C; (18)Enthalpy of Vaporization: 71.8±3.0 kJ/mol; (19)Boiling Point: 481.6±40.0 °C at 760 mmHg; (20)Vapour Pressure: 0.0±1.2 mmHg at 25°C.

Preparation of Etofenprox: this chemical can be prepared by 1-(bromomethyl)-3-phenoxybenzene and tetrahydrofuran by irradiation. This reaction time is 35 min. The yield is about 95%.

Etofenprox can be prepared by 1-(bromomethyl)-3-phenoxybenzene and tetrahydrofuran by irradiation

You can still convert the following datas into molecular structure:
(1)SMILES: CCOC1=CC=C(C=C1)C(C)(C)COCC2=CC(=CC=C2)OC3=CC=CC=C3
(2)Std. InChI: InChI=1S/C25H28O3/c1-4-27-22-15-13-21(14-16-22)25(2,3)19-26-18-20-9-8-12-24(17-20)28-23-10-6-5-7-11-23/h5-17H,4,18-19H2,1-3H3
(3)Std. InChIKey: YREQHYQNNWYQCJ-UHFFFAOYSA-N

The toxicity data is as follows:  

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 5gm/kg (5000mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
duck LD50 unreported > 2gm/kg (2000mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
mouse LD50 intraperitoneal > 13400mg/kg (13400mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
mouse LD50 oral > 107gm/kg (107000mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
mouse LD50 skin > 2140mg/kg (2140mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
mouse LD50 subcutaneous > 53600mg/kg (53600mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
rat LC50 inhalation > 5900mg/m3/4H (5900mg/m3)   Nippon Noyaku Gakkaishi. Journal of the Pesticide Science Society of Japan. Vol. 15, Pg. 505, 1989.
rat LD50 intraperitoneal > 42880mg/kg (42880mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
rat LD50 oral > 42800mg/kg (42800mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
rat LD50 skin > 2140mg/kg (2140mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.
rat LD50 subcutaneous > 32160mg/kg (32160mg/kg)   Japan Pesticide Information. Vol. (48), Pg. 23, 1986.