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Kresoxim-methyl

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Name

Kresoxim-methyl

EINECS 604-351-6
CAS No. 143390-89-0 Density 1.1 g/cm3
PSA 57.12000 LogP 3.09750
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 N/A
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;

Article Data 16

Kresoxim-methyl Synthetic route

593-56-6

N-methoxylamine hydrochloride

143211-10-3

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

143390-89-0

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

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

ortho-cresol

133409-72-0

methyl (E)-2-[2-(bromomethyl)phenyl]-2-(methoxyimino)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%
593-56-6

N-methoxylamine hydrochloride

143211-10-3

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

A

143390-89-0

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

B

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%
248582-68-5

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

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

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
143211-10-3

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

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
143390-88-9

methyl 2-(2-methylphenoxymethyl)phenylglyoxylate dimethyl acetal

593-56-6

N-methoxylamine hydrochloride

143211-10-3

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

143390-89-0

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

Conditions
ConditionsYield
With hydrogenchloride In methanol; dichloromethane
150869-72-0

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

74-87-3

methylene chloride

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
189813-45-4

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

95-48-7

ortho-cresol

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;
108475-90-7

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

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

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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