Conditions | Yield |
---|---|
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran; water at 20℃; for 0.5h; | 100% |
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; | 100% |
With sodium hypophosphite monohydrate; 5%-palladium/activated carbon; hypophosphorous acid In 2-methyltetrahydrofuran; water for 3h; Sonication; chemoselective reaction; | 98% |
Conditions | Yield |
---|---|
for 1h; | 99.5% |
5-methoxy-3H-1,4-benzodiazepine
2-carbomethoxyaniline
Conditions | Yield |
---|---|
In 1,4-dioxane; water for 2h; Heating; | 99% |
2-azido-benzoic acid methyl ester
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium iodide In acetonitrile for 0.0833333h; Ambient temperature; | 98% |
With hydrogen iodide at 20℃; for 1.5h; | 95% |
With ammonium chloride; indium In ethanol for 1h; Reduction; Heating; | 92% |
phthalimide
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With sodium hypochlorite; sodium hydroxide In methanol; water at 0 - 80℃; for 0.0583333h; Temperature; | 96.8% |
5-Methoxy-2-methyl-3H-benzo[e][1,4]diazepine
2-carbomethoxyaniline
Conditions | Yield |
---|---|
In 1,4-dioxane; water for 2h; Heating; | 96% |
2-[(2-methoxycarbonylphenylamino)methylene]malonic acid diethyl ester
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With ethylenediamine In ethanol at 20℃; for 2.3h; | 96% |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 65℃; for 18h; Inert atmosphere; | 95% |
With thionyl chloride Reflux; | 93% |
With thionyl chloride at 0℃; Inert atmosphere; Reflux; | 88% |
2-[3-acetoxy-2-(2-methoxycarbonyl-phenylazo)-propyl]-benzoic acid methyl ester
B
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol under 37503 Torr; for 2h; | A 84% B 95% |
Conditions | Yield |
---|---|
In methanol at 0 - 75℃; for 1h; | 95% |
Conditions | Yield |
---|---|
In diethyl ether at 0℃; | 94% |
With diethyl ether | |
In diethyl ether at 20℃; for 1h; |
Conditions | Yield |
---|---|
With tert.-butylhydroperoxide; caesium carbonate at 20 - 30℃; for 4h; Reagent/catalyst; Sealed tube; | 93% |
With dihydrogen peroxide; sodium methylate Esterification; oxidation; |
Conditions | Yield |
---|---|
With sulfuric acid for 3h; Reflux; | 92% |
With sodium hydride In mineral oil for 2h; Reflux; Inert atmosphere; | 91% |
With caesium carbonate at 20℃; | 88% |
2-Amino-3-triisopropylsilanyl-benzoic acid methyl ester
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With trifluoroacetic acid In tetrachloromethane for 2h; Heating; | 92% |
Conditions | Yield |
---|---|
With dichloro[2,2'-bis(diphenylphosphino)-1,1'-binaphthyl]palladium(II); triethylamine at 100℃; under 2585.74 Torr; for 16h; | 92% |
With triethylamine; 1,1'-bis(diphenylphosphino)ferrocene; [(Pd(μ-Cl)(κ(2)-P,C-P(OC6H2-2,4-tBu2)(OC6H3-2,4-tBu2)2))2] In toluene at 120℃; for 12h; |
Conditions | Yield |
---|---|
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h; | 92% |
Conditions | Yield |
---|---|
90.4% |
methyl 2-(methyl(nitroso)amino)benzoate
A
benzoic acid methyl ester
B
4-nitrobenzoic acid methyl ester
C
diphenic acid dimethyl ester
D
dimethyl (1,1'-biphenyl)-2,4'-dicarboxylate
E
dimethyl (1,1'-biphenyl)-2,3'-dicarboxylate
F
2-(benzoyl-methylamino)benzoic acid methyl ester
G
2-carbomethoxyaniline
H
Methyl N-methylanthranilate
I
methyl 2-(benzamido)benzoate
J
N-formylanthranilic acid methyl ester
Conditions | Yield |
---|---|
at 220℃; for 0.25h; Sealed tube; | A n/a B n/a C n/a D n/a E n/a F n/a G n/a H n/a I 90% J n/a |
Conditions | Yield |
---|---|
With samarium; iodine In methanol for 5h; Heating; | 86% |
anthranilic acid
methyl salicylate
A
2-carbomethoxyaniline
B
salicylic acid
Conditions | Yield |
---|---|
Stage #1: anthranilic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl salicylate at 110℃; for 24h; | A 84% B n/a |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 1h; Heating; | 82% |
methyl 2-(3,3-diisopropylureido)benzoate
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With water for 18h; Reflux; | 80% |
2-(1-acetoxymethyl-3-ethoxycarbonylpropylazo)benzoic acid methyl ester
B
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With hydrogen; nickel In methanol under 37503 Torr; for 3h; | A 79% B n/a |
methanol
phthalimide
A
methyl 2-((methoxycarbonyl)amino)benzoate
B
2-carbomethoxyaniline
Conditions | Yield |
---|---|
Stage #1: methanol With iodobenzene; toluene-4-sulfonic acid; sodium sulfate; 3-chloro-benzenecarboperoxoic acid at 0℃; for 0.166667h; Inert atmosphere; Stage #2: phthalimide With potassium carbonate at 0 - 20℃; for 2h; Hofmann-type rearrangement; Inert atmosphere; regioselective reaction; | A 79% B 14% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 3h; Reflux; Inert atmosphere; | 77% |
Conditions | Yield |
---|---|
With acetamidine hydrochloride; caesium carbonate In N,N-dimethyl-formamide at 130℃; for 20h; Inert atmosphere; Green chemistry; | 76% |
With copper(I) oxide; sodium azide; L-proline In dimethyl sulfoxide at 100℃; for 0.25h; Inert atmosphere; | 64% |
With copper acetylacetonate; ammonium hydroxide; caesium carbonate; acetylacetone In water; N,N-dimethyl-formamide at 90℃; for 24h; Inert atmosphere; | 23% |
Conditions | Yield |
---|---|
With thionyl chloride at 0 - 55℃; for 6h; | 75% |
Conditions | Yield |
---|---|
With dmap; ethyl 2-cyanoacetate at 20℃; for 4.5h; chemoselective reaction; | 73% |
Conditions | Yield |
---|---|
With samarium; iodine for 6h; Ambient temperature; | 70% |
methyl 2-isothiocyanatobenzoate
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With 3,4-dimercaptotoluene; sodium hydrogencarbonate In methanol at 25℃; for 2h; | 69% |
2-carbomethoxyaniline
p-toluenesulfonyl chloride
methyl N-tosylanthranilate
Conditions | Yield |
---|---|
In pyridine at 25℃; | 100% |
Stage #1: 2-carbomethoxyaniline With pyridine In dichloromethane at 25℃; for 1h; Inert atmosphere; Stage #2: p-toluenesulfonyl chloride In dichloromethane at 25℃; for 24h; Inert atmosphere; | 99% |
In pyridine at 0℃; for 1h; | 98% |
2-carbomethoxyaniline
3,4-dimethoxybenzoic acid chloride
methyl N-(3,4-dimethoxybenzoyl)anthranilate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 0.5h; | 100% |
pivaloyl chloride
2-carbomethoxyaniline
methyl N-trimethylacetylanthranilate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0 - 20℃; for 16h; | 100% |
With potassium carbonate In benzene Heating; | 98% |
With triethylamine In benzene for 1h; Heating; | |
With triethylamine In dichloromethane at 0 - 20℃; |
n-valeryl chloride
2-carbomethoxyaniline
methyl 2-(valerylamino)benzoate
Conditions | Yield |
---|---|
With triethylamine In chloroform at 0℃; for 4h; | 100% |
With potassium carbonate In benzene Heating; | 82% |
methyl thioisocyanate
2-carbomethoxyaniline
2-mercapto-3-methyl-3,4-dihydroquinazolin-4-one
Conditions | Yield |
---|---|
In neat (no solvent) for 72h; Ambient temperature; | 100% |
Benzoyl isothiocyanate
2-carbomethoxyaniline
2-(3-Benzoylthioureido)benzoesaeuremethylester
Conditions | Yield |
---|---|
In neat (no solvent) Ambient temperature; | 100% |
2-chloroethyl isothiocyanate
2-carbomethoxyaniline
methyl 2-<3-(2-chloroethyl)ureido>benzoate
Conditions | Yield |
---|---|
for 16h; Ambient temperature; | 100% |
ethoxyacetyl chloride
2-carbomethoxyaniline
methyl (2-ethoxyacetamido)benzoate
Conditions | Yield |
---|---|
With potassium carbonate In benzene Heating; | 100% |
With triethylamine In dichloromethane | 92.8% |
2-carbomethoxyaniline
isopentanoyl chloride
2-(3-Methyl-butyrylamino)-benzoic acid methyl ester
Conditions | Yield |
---|---|
With potassium carbonate In benzene Heating; | 100% |
With sodium hydrogencarbonate In tetrahydrofuran |
Conditions | Yield |
---|---|
With water; fluorine In chloroform; acetonitrile at -15℃; for 0.0333333h; | 100% |
With tert.-butylhydroperoxide; chromium silicalite-2 In methanol at 65℃; for 5h; | 91% |
With tert.-butylhydroperoxide; molecular sieve In methanol for 5h; Heating; | 91% |
With dihydrogen peroxide; <ϖ-C5H5N(1+)(CH2)15CH3>34>(3-) In chloroform for 24h; Heating; | 81% |
bis(trichloromethyl) carbonate
2-carbomethoxyaniline
methyl 2-isocyanatobenzoate
Conditions | Yield |
---|---|
With pyridine In dichloromethane at 20℃; for 4h; | 100% |
With triethylamine In 1,2-dichloro-ethane at 0 - 85℃; for 8.5h; Inert atmosphere; |
3-chlorosulfonyl-4-methylbenzoic acid chloride
2-carbomethoxyaniline
Conditions | Yield |
---|---|
Stage #1: 2-carbomethoxyaniline With sodium hydride In tetrahydrofuran for 0.333333h; Stage #2: 3-chlorosulfonyl-4-methylbenzoic acid chloride In tetrahydrofuran at 20℃; | 100% |
2-(4-acetamidophenylsulfonamido)-4-methylpentanoic acid
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With phosphorus trichloride under 760.051 Torr; Heating; | 100% |
2-(4-acetamidophenylsulfonamido)propanoic acid
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With phosphorus trichloride Heating; | 100% |
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With phosphorus trichloride | 100% |
methyl chloroformate
2-carbomethoxyaniline
methyl 2-((methoxycarbonyl)amino)benzoate
Conditions | Yield |
---|---|
In toluene for 8h; Inert atmosphere; Reflux; | 99% |
In toluene for 8h; Reflux; | 88% |
Conditions | Yield |
---|---|
With bromine; sodium hydrogensulfite In dichloromethane; acetic acid | 99% |
Stage #1: 2-carbomethoxyaniline With bromine In dichloromethane; water at 20℃; for 0.166667h; Industrial scale; Stage #2: With dihydrogen peroxide In dichloromethane; water for 6h; Industrial scale; | 96% |
With dihydrogen peroxide; bromine In dichloromethane; water Solvent; | 96.86% |
2-carbomethoxyaniline
Glycine ethyl ester isocyanate
N-(carbamoyl)glycinaethylester
Conditions | Yield |
---|---|
for 16h; Ambient temperature; | 99% |
2-carbomethoxyaniline
dianthranilide
Conditions | Yield |
---|---|
With sodium hydride In tetrahydrofuran for 72h; Reflux; | 99% |
With sodium hydride In tetrahydrofuran for 96h; | 95% |
With sodium hydride In tetrahydrofuran; mineral oil at 25 - 30℃; for 76.5h; Inert atmosphere; | 81% |
di-tert-butyl dicarbonate
2-carbomethoxyaniline
Conditions | Yield |
---|---|
With lanthanum(III) nitrate at 20℃; for 0.0833333h; | 99% |
In ethanol at 50℃; for 216h; Inert atmosphere; | 98% |
With lanthanum(III) nitrate hexahydrate at 20 - 50℃; for 4h; | 93% |
acrylic acid methyl ester
2-carbomethoxyaniline
2-(E)-[2-methoxycarbonylphenyl]acrylic acid methylester
Conditions | Yield |
---|---|
Stage #1: 2-carbomethoxyaniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; Heck-Matsuda reaction; | 99% |
Stage #1: 2-carbomethoxyaniline With tert.-butylnitrite In methanol at 0℃; for 0.5h; Heck-Matsuda reaction; Stage #2: acrylic acid methyl ester With methanesulfonic acid; palladium diacetate In methanol at 0 - 25℃; for 48h; Heck-Matsuda reaction; | 99% |
With tert.-butylnitrite; methanesulfonic acid; palladium diacetate In methanol; N,N-dimethyl-formamide at 25℃; Heck Reaction; Flow reactor; | 96% |
2,2’-dibromodiphenylmethane
2-carbomethoxyaniline
2-(anthracen-9-yl)aniline
Conditions | Yield |
---|---|
Stage #1: 2,2’-dibromodiphenylmethane With magnesium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Reflux; Stage #2: 2-carbomethoxyaniline In tetrahydrofuran at 20℃; for 4h; Inert atmosphere; | 99% |
Conditions | Yield |
---|---|
Stage #1: cyclohexanone; 2-carbomethoxyaniline With chloro-trimethyl-silane In N,N-dimethyl-formamide Schlenk technique; Inert atmosphere; Stage #2: With sodium tetrahydroborate In N,N-dimethyl-formamide at 0℃; for 0.25h; Schlenk technique; Inert atmosphere; | 99% |
phthalic anhydride
2-carbomethoxyaniline
methyl 2-(1,3-dioxoisoindolin-2-yl)benzoate
Conditions | Yield |
---|---|
With triethylamine In toluene Reflux; Dean-Stark; | 98% |
With acetic acid for 5h; Condensation; Heating; | 72.2% |
With acetic acid | |
With acetic acid Reflux; |
chloroacetyl chloride
2-carbomethoxyaniline
methyl N-(chloroacetyl)anthranilate
Conditions | Yield |
---|---|
With potassium carbonate In acetone at 20℃; for 4h; | 98% |
With sodium hydrogencarbonate In tetrahydrofuran; water | 96% |
In benzene Heating; | 95% |
formaldehyd
2-carbomethoxyaniline
N,N'-methanediyl-di-anthranilic acid dimethyl ester
Conditions | Yield |
---|---|
In water | 98% |
1.Introduction of Methyl anthranilate
The Methyl anthranilate, with its CAS registry number 134-20-3, has the IUPAC name of methyl 2-aminobenzoate. For being a kind of colorless to light yellow liquid with a smell of orange blossom, it is slightly soluble in water while soluble in ethanol, diethyl ether and other organic solvents, and it is stable but incompatible with strong oxidizing agents. Besides, its product categories are including Carboxylicester; Benzene derivatives; Aromatic Esters; pharmacetical.
2. The physical properties of Methyl anthranilate
(1)ACD/LogP: 2.04; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.04; (4)ACD/LogD (pH 7.4): 2.04; (5)ACD/BCF (pH 5.5): 20.85; (6)ACD/BCF (pH 7.4): 20.86; (7)ACD/KOC (pH 5.5): 306.06; (8)ACD/KOC (pH 7.4): 306.21; (9)#H bond acceptors: 3; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 3; (12)Polar Surface Area: 52.32; (13)Index of Refraction: 1.565; (14)Molar Refractivity: 42.26 cm3; (15)Molar Volume: 129.6 cm3; (16)Polarizability: 16.75×10-24 cm3; (17)Surface Tension: 46.2 dyne/cm; (18)Density: 1.166 g/cm3; (19)Flash Point: 112.9 °C; (20)Enthalpy of Vaporization: 49.35 kJ/mol; (21)Boiling Point: 256 °C at 760 mmHg; (22)Vapour Pressure: 0.0158 mmHg at 25°C; (23)Exact Mass: 151.063329; (24)MonoIsotopic Mass: 151.063329; (25)Topological Polar Surface Area: 52.3; (26)Heavy Atom Count: 11; (27)Complexity: 147.
3.Structure descriptors of Methyl anthranilate
(1)Canonical SMILES: COC(=O)C1=CC=CC=C1N
(2)InChI: InChI=1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3
(3)InChIKey: VAMXMNNIEUEQDV-UHFFFAOYSA-N
4.Safety information of Methyl anthranilate
When you are dealing with this chemical, you should be very careful. For being irritating to eyes, respiratory system and skin, it may cause inflammation to the skin or other mucous membranes. Therefore, you should wear suitable protective clothing, gloves and eye/face protection. And if in case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
5.Toxity data of Methyl anthranilate
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
guinea pig | LD50 | oral | 2780mg/kg (2780mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: DYSPNEA LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
mouse | LD50 | oral | 3900mg/kg (3900mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
rabbit | LD50 | skin | > 5gm/kg (5000mg/kg) | Food and Cosmetics Toxicology. Vol. 12, Pg. 935, 1974. | |
rat | LD50 | oral | 2910mg/kg (2910mg/kg) | BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: COMA | Food and Cosmetics Toxicology. Vol. 2, Pg. 327, 1964. |
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