Product Name

  • Name

    Kresoxim-methyl

  • EINECS 604-351-6
  • CAS No. 143390-89-0
  • Article Data16
  • CAS DataBase
  • Density 1.1 g/cm3
  • Solubility 2 mg/L (20 °C ) in water
  • Melting Point 98-100 °C
  • Formula C18H19NO4
  • Boiling Point 429.4 °C at 760 mmHg
  • Molecular Weight 313.353
  • Flash Point 171.2 °C
  • Transport Information UN 3077 9/PG 3
  • Appearance
  • Safety 2-36/37-60-61
  • Risk Codes 40-50/53
  • Molecular Structure Molecular Structure of 143390-89-0 (Kresoxim-methyl)
  • Hazard Symbols HarmfulXn,DangerousN
  • Synonyms Bas 490F;Methyl (E)-alpha-(methoxyimino)-2-((2-methylphenoxy)methyl)benzeneacetate;BAS 490 F;Benzeneacetic acid,R-(methoxyimino)-2-[(2- methylphenoxy)methyl]-,methyl ester,(RE)-;Methyl (E)-2-methoxyimino-(2-(o-tolyloxymethyl)Phenyl)Acetate;Kresoxim methyl;
  • PSA 57.12000
  • LogP 3.09750

Synthetic route

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
In methanol for 6h; Reflux;84.8%
ortho-cresol
95-48-7

ortho-cresol

methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate
133409-72-0

methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With copper(l) iodide In butanone for 4h; Concentration; Reagent/catalyst; Reflux;80%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

A

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

B

methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate
248582-68-5

methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate

Conditions
ConditionsYield
In pyridine at 20℃; for 17.5h; Condensation;A 63%
B 28%
...Expand
methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate
248582-68-5

methyl (Z)-O-methyloximino-2-[(2-methyl)phenoxymethyl]phenylacetate

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With iodine In benzene at 63℃; for 120h; Isomerization; UV-irradiation;
2-(2-methylphenoxymethyl)phenylzinc chloride

2-(2-methylphenoxymethyl)phenylzinc chloride

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 61 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / 0 °C
2: 63 percent / pyridine / 17.5 h / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 61 percent / Pd(PPh3)4 / tetrahydrofuran / 4 h / 0 °C
2: 28 percent / pyridine / 17.5 h / 20 °C
3: I2 / benzene / 120 h / 63 °C / UV-irradiation
View Scheme
2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / pyridine / 17.5 h / 20 °C
2: I2 / benzene / 120 h / 63 °C / UV-irradiation
View Scheme
methyl 2-(2-methylphenoxymethyl)phenylglyoxylate dimethyl acetal
143390-88-9

methyl 2-(2-methylphenoxymethyl)phenylglyoxylate dimethyl acetal

N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester
143211-10-3

2-oxo-2-(((o-tolyl)oxymethyl)phenyl)acetic acid methyl ester

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With hydrogenchloride In methanol; dichloromethane
...Expand
methyl E-2-(2-methylphenoxymethyl)phenylglyoxylate oxime
150869-72-0

methyl E-2-(2-methylphenoxymethyl)phenylglyoxylate oxime

methylene chloride
74-87-3

methylene chloride

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With sodium methylate In 1-methyl-pyrrolidin-2-one; methanol; diethyl ether
(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate
189813-45-4

(E)-methyl 2-(2-(chloromethyl)phenyl)-2-(methoxyimino)acetate

ortho-cresol
95-48-7

ortho-cresol

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 50℃; for 64h;
2-[(2-methylphenoxy)methyl]benzoic acid
108475-90-7

2-[(2-methylphenoxy)methyl]benzoic acid

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: thionyl chloride / 3 h / Reflux
2.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
3.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
3.2: 5 h / Reflux
4.1: methanol / 6 h / Reflux
View Scheme
2-[(2-methylphenoxy)methyl]benzoyl chloride
143211-21-6

2-[(2-methylphenoxy)methyl]benzoyl chloride

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
2.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
2.2: 5 h / Reflux
3.1: methanol / 6 h / Reflux
View Scheme
2-[(2-methylphenoxy)methyl]benzoyl cyanide
143211-11-4

2-[(2-methylphenoxy)methyl]benzoyl cyanide

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
1.2: 5 h / Reflux
2.1: methanol / 6 h / Reflux
View Scheme
methanol
67-56-1

methanol

2-methoxyimino(2-(o-tolyl)oxymethylphenyl)acetic acid
137169-29-0

2-methoxyimino(2-(o-tolyl)oxymethylphenyl)acetic acid

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Stage #1: 2-methoxyimino(2-(o-tolyl)oxymethylphenyl)acetic acid With thionyl chloride In N,N-dimethyl-formamide at 40 - 45℃; for 8h;
Stage #2: methanol at 60 - 65℃; for 2h;		42.5 g
ortho-cresol
95-48-7

ortho-cresol

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium methylate / methanol / 1 h / 20 °C
1.2: 2 h / 190 °C
2.1: thionyl chloride / 3 h / Reflux
3.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
4.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
4.2: 5 h / Reflux
5.1: methanol / 6 h / Reflux
View Scheme
2-methyl-α-hydroxyiminobenzeneacetonitrile
107960-33-8

2-methyl-α-hydroxyiminobenzeneacetonitrile

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 11 - 15 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 11 - 15 °C
2.1: sodium hydroxide / water / 3 h / 70 - 75 °C
2.2: 5 - 10 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 1 h / 7 - 15 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-methyl-a-cyanobenzoxime potassium
178983-50-1

2-methyl-a-cyanobenzoxime potassium

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 3 h / 70 - 75 °C
2.2: 5 - 10 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
2.2: 6 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-methyl-a-cyanobenzoxime sodium

2-methyl-a-cyanobenzoxime sodium

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
2.2: 25 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium hydroxide / water / 3 h / 70 - 75 °C
2.2: 5 - 10 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 4 steps
1.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
2.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
2.2: 6 °C
3.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
4.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-benzofuran-1(3H)-one
87-41-2

2-benzofuran-1(3H)-one

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: sodium methylate / methanol / 1 h / 20 °C
1.2: 2 h / 190 °C
2.1: thionyl chloride / 3 h / Reflux
3.1: tetrabutylammomium bromide / toluene / 2.5 h / 20 - 35 °C
4.1: hydrogenchloride; acetic anhydride / tert-butyl methyl ether / 10 h / -5 - 30 °C
4.2: 5 h / Reflux
5.1: methanol / 6 h / Reflux
View Scheme
2-tolylmethylnitrile
22364-68-7

2-tolylmethylnitrile

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: ethyl nitrite; sodium hydroxide / chlorobenzene / 1 h / 15 °C
2.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
3.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
3.2: 6 °C
4.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
5.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: isopentyl nitrite; potassium hydroxide / chlorobenzene / 1 h / 15 °C
2.1: sodium hydroxide / water / 0.5 h / 8 - 10 °C
3.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
3.2: 6 °C
4.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
5.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: sodium carbonate; n-propyl nitrite / dichloromethane / 1.5 h / 5 °C
2.1: sodium hydroxide / water / 0.5 h / 11 - 15 °C
3.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
3.2: 25 °C
4.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
5.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
2-methyl-α-methoxyiminophenylacetonitrile

2-methyl-α-methoxyiminophenylacetonitrile

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium carbonate / water / 1.6 h / 80 - 85 °C
1.2: 6 °C
2.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
3.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / 2.5 h / 50 - 65 °C
1.2: 25 °C
2.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
3.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water / 3 h / 70 - 75 °C
1.2: 5 - 10 °C
2.1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
3.1: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate
120974-97-2

methyl-(E)-2-(2-tolyl)-2-methoxyiminoacetate

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dibenzoyl peroxide; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / 1,2-dichloro-ethane / 4 h / 55 °C
2: copper(l) iodide / butanone / 4 h / Reflux
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-methyl 2-(2-((4-iodo-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate

(E)-methyl 2-(2-((4-iodo-2-methylphenoxy)methyl)phenyl)-2-(methoxyimino)acetate

Conditions
ConditionsYield
With Iodine monochloride In dichloromethane; acetic acid at 20℃; for 5h;95%
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-2-methoxyimino-2-{[2-(2-tolyl)oxymethyl]phenyl}acetic acid
1007364-30-8

(E)-2-methoxyimino-2-{[2-(2-tolyl)oxymethyl]phenyl}acetic acid

Conditions
ConditionsYield
Stage #1: methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate With sodium hydroxide In water; toluene at 40 - 70℃; for 6h;
Stage #2: With hydrogenchloride In water; toluene at 10 - 15℃; pH=1.5;		93.75%
With water; sodium hydroxide In methanol for 3h; Reflux;92%
With sodium hydroxide In methanol at 65℃;86%
With sodium hydroxide; water In methanol Reflux;
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

N-Methyl-E-2-methoxyimino-2-[(2-methylphenyloxymethyl)phenyl]-acetamide
156996-22-4

N-Methyl-E-2-methoxyimino-2-[(2-methylphenyloxymethyl)phenyl]-acetamide

Conditions
ConditionsYield
In methylamine
In methylamine
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hex-5-ynoate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hex-5-ynoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoate

(E)-tert-butyl 6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
3: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 16 h / 20 °C / 3040.2 Torr
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoic acid

(E)-6-(4-((2-(2-methoxy-1-(methoxyimino)-2-oxoethyl)benzyl)oxy)-3-methylphenyl)hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
3: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 16 h / 20 °C / 3040.2 Torr
4: formic acid / 3 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-tert-butyl 6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoate

(E)-tert-butyl 6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / methanol / 65 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

(E)-6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoic acid

(E)-6-(2-(methoxyimino)-2-(2-((o-tolyloxy)methyl)phenyl)acetoxy)hexanoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide / methanol / 65 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
3: formic acid / 3 h / 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C28H32N2O8

C28H32N2O8

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Iodine monochloride / dichloromethane; acetic acid / 5 h / 20 °C
2: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere
3: Wilkinson's catalyst; hydrogen / tetrahydrofuran / 16 h / 20 °C / 3040.2 Torr
4: formic acid / 3 h / 20 °C / Inert atmosphere
5: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C27H30N2O8

C27H30N2O8

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: sodium hydroxide / methanol / 65 °C
2: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere
3: formic acid / 3 h / 20 °C / Inert atmosphere
4: triethylamine / acetonitrile / 0 - 20 °C / Inert atmosphere
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C23H28BrNO4

C23H28BrNO4

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; water / methanol / 3 h / Reflux
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 20 °C / Reflux
View Scheme
methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate
143390-89-0

methyl (E)-2-methoxyimino-2-[2-(o-tolyloxymethyl)phenyl]acetate

C41H43NO4P(1+)*Br(1-)

C41H43NO4P(1+)*Br(1-)

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sodium hydroxide; water / methanol / 3 h / Reflux
2: dicyclohexyl-carbodiimide; dmap / dichloromethane / 12 h / 20 °C / Reflux
3: potassium iodide / acetonitrile / 24 h / Reflux
View Scheme

Kresoxim-methyl Chemical Properties

Molecular Structure of Kresoxim-methyl (CAS NO.143390-89-0):

IUPAC Name: Methyl (2E)-2-methoxyimino-2-[2-[(2-methylphenoxy)methyl]phenyl]acetate
Molecular Formula: C18H19NO4
Molecular Weight: 313.35 g/mol
Density: 1.1 g/cm3
Melting Point: 98-100 °C
Boiling Point: 429.4 °C  at 760 mmHg
Flash Point: 171.2 °C
Water Solubility: 2 mg/L (20 °C )
Storage Temp: 0-6 °C 
Index of Refraction: 1.53
Molar Refractivity: 87.92 cm3
Molar Volume: 284.1 cm3
Surface Tension: 36.8 dyne/cm 
XLogP3-AA: 4.1
H-Bond Acceptor: 5
Rotatable Bond Count: 7
Exact Mass: 313.131408
MonoIsotopic Mass: 313.131408
Topological Polar Surface Area: 57.1
Heavy Atom Count: 23 
Canonical SMILES: CC1=CC=CC=C1OCC2=CC=CC=C2C(=NOC)C(=O)OC
Isomeric SMILES: CC1=CC=CC=C1OCC2=CC=CC=C2/C(=N\OC)/C(=O)OC
InChI: InChI=1S/C18H19NO4/c1-13-8-4-7-11-16(13)23-12-14-9-5-6-10-15(14)17(19-22-3)18(20)21-2/h4-11H,12H2,1-3H3/b19-17+
InChIKey: ZOTBXTZVPHCKPN-HTXNQAPBSA-N
Product Categories of Kresoxim-methyl (CAS NO.143390-89-0): Agricultural chemicals(bactericide)

Kresoxim-methyl Toxicity Data With Reference

1.    

orl-rat LD50:5000 mg/kg

     FEREAC    Federal Register. 64 (1999),31130.
2.    

skn-rat LD50:2000 mg/kg

     FEREAC    Federal Register. 64 (1999),31130.
3.    

ihl-rat LC50:5.6 g/m3

     FEREAC    Federal Register. 64 (1999),31130.

Kresoxim-methyl Safety Profile

Hazard Codes: HarmfulXn, DangerousN
Risk Statements: 40-50/53 
R40:Limited evidence of a carcinogenic effect. 
R50/53:Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.
Safety Statements: 2-36/37-60-61 
S2:Keep out of the reach of children. 
S36/37:Wear suitable protective clothing and gloves. 
S60:This material and its container must be disposed of as hazardous waste. 
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN3077 9/PG 3
Moderately toxic by skin contact. Low toxicity by ingestion and inhalation. Questionable carcinogen with experimental data reported. When heated to decomposition it emits toxic vapors of NOx.

Kresoxim-methyl Specification

 Kresoxim-methyl (CAS NO.143390-89-0) is also named as Bas 490F ; HSDB 7020 ; Methyl (E)-alpha-(methoxyimino)-2-((2-methylphenoxy)methyl)benzeneacetate ; Benzeneacetic acid, alpha-(methoxyimino)-2-((2-methylphenoxy)methyl)-, methyl ester, (E)- .

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