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Methyl anthranilate

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Name

Methyl anthranilate

EINECS 205-132-4
CAS No. 134-20-3 Density 1.166 g/cm3
PSA 52.32000 LogP 1.63660
Solubility slightly soluble in water Melting Point 24 °C(lit.)
Formula C8H9NO2 Boiling Point 256 °C at 760 mmHg
Molecular Weight 151.165 Flash Point 112.9 °C
Transport Information N/A Appearance colorless to light yellow liquid with a smell of orange blossom
Safety 26-36/37/39 Risk Codes 36/37/38
Molecular Structure Molecular Structure of 134-20-3 (Methyl anthranilate) Hazard Symbols IrritantXi
Synonyms

Anthranilicacid, methyl ester (6CI,8CI);2-(Methoxycarbonyl)aniline;2-Aminobenzoic acidmethyl ester;2-Carbomethoxyaniline;Bird Shield;Grain 96-1;Methyl2-aminobenzoate;Methyl 6-aminobenzoate;Methylo-aminobenzoate;NSC 3109;ReJex-iT;Rejex-iT TP 40;SunaromeUVA;o-(Methoxycarbonyl)aniline;Methyl anthranilate;

Article Data 177

Methyl anthranilate Synthetic route

606-27-9

methyl 2-nitrobenzoate

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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%
67-56-1

methanol

64001-48-5

2-(sulfinylamino)benzoyl chloride

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
for 1h;99.5%
107468-21-3

5-methoxy-3H-1,4-benzodiazepine

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In 1,4-dioxane; water for 2h; Heating;99%
16714-23-1

2-azido-benzoic acid methyl ester

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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%
136918-14-4

phthalimide

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With sodium hypochlorite; sodium hydroxide In methanol; water at 0 - 80℃; for 0.0583333h; Temperature;96.8%
107468-34-8

5-Methoxy-2-methyl-3H-benzo[e][1,4]diazepine

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In 1,4-dioxane; water for 2h; Heating;96%
42063-41-2

2-[(2-methoxycarbonylphenylamino)methylene]malonic acid diethyl ester

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 2.3h;96%
67-56-1

methanol

118-92-3

anthranilic acid

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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%
906097-05-0

2-[3-acetoxy-2-(2-methoxycarbonyl-phenylazo)-propyl]-benzoic acid methyl ester

A

acetic acid 1-oxo-1,2,3,4-tetrahydro-isoquinolin-3-ylmethyl ester

B

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With hydrogen; nickel In methanol under 37503 Torr; for 2h;A 84%
B 95%
118-48-9

isatoic anhydride

124-41-4

sodium methylate

134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In methanol at 0 - 75℃; for 1h;95%

Methyl anthranilate Consensus Reports

Reported in EPA TSCA Inventory.

Methyl anthranilate Specification

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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