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134-20-3

Basic Information
CAS No.: 134-20-3
Name: Methyl anthranilate
Article Data: 177
Molecular Structure:
Molecular Structure of 134-20-3 (Methyl anthranilate)
Formula: C8H9NO2
Molecular Weight: 151.165
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;
EINECS: 205-132-4
Density: 1.166 g/cm3
Melting Point: 24 °C(lit.)
Boiling Point: 256 °C at 760 mmHg
Flash Point: 112.9 °C
Solubility: slightly soluble in water
Appearance: colorless to light yellow liquid with a smell of orange blossom
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-36/37/39
PSA: 52.32000
LogP: 1.63660
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%
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Consensus Reports

Reported in EPA TSCA Inventory.

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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