Product Name

  • Name

    Methyl anthranilate

  • EINECS 205-132-4
  • CAS No. 134-20-3
  • Article Data177
  • CAS DataBase
  • Density 1.166 g/cm3
  • 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
  • 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;
  • PSA 52.32000
  • LogP 1.63660

Synthetic route

methyl 2-nitrobenzoate
606-27-9

methyl 2-nitrobenzoate

2-carbomethoxyaniline
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%
methanol
67-56-1

methanol

2-(sulfinylamino)benzoyl chloride
64001-48-5

2-(sulfinylamino)benzoyl chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
for 1h;99.5%
5-methoxy-3H-1,4-benzodiazepine
107468-21-3

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

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In 1,4-dioxane; water for 2h; Heating;99%
2-azido-benzoic acid methyl ester
16714-23-1

2-azido-benzoic acid methyl ester

2-carbomethoxyaniline
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%
phthalimide
136918-14-4

phthalimide

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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
107468-34-8

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

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In 1,4-dioxane; water for 2h; Heating;96%
2-[(2-methoxycarbonylphenylamino)methylene]malonic acid diethyl ester
42063-41-2

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

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

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

methanol

anthranilic acid
118-92-3

anthranilic acid

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

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

B

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

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

isatoic anhydride

sodium methylate
124-41-4

sodium methylate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In methanol at 0 - 75℃; for 1h;95%
anthranilic acid
118-92-3

anthranilic acid

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
In diethyl ether at 0℃;94%
With diethyl ether
In diethyl ether at 20℃; for 1h;
methanol
67-56-1

methanol

indole-2,3-dione
91-56-5

indole-2,3-dione

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With tert.-butylhydroperoxide; caesium carbonate at 20 - 30℃; for 4h; Reagent/catalyst; Sealed tube;93%
With dihydrogen peroxide; sodium methylate Esterification; oxidation;
methanol
67-56-1

methanol

isatoic anhydride
118-48-9

isatoic anhydride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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
110036-11-8

2-Amino-3-triisopropylsilanyl-benzoic acid methyl ester

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With trifluoroacetic acid In tetrachloromethane for 2h; Heating;92%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

2-bromoaniline
615-36-1

2-bromoaniline

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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;
2-bromobenzoic acid methyl ester
610-94-6

2-bromobenzoic acid methyl ester

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With copper(I) oxide; ammonium hydroxide In 1-methyl-pyrrolidin-2-one at 80℃; for 24h;92%
anthranilic acid
118-92-3

anthranilic acid

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
90.4%
methyl 2-(methyl(nitroso)amino)benzoate
68061-82-5

methyl 2-(methyl(nitroso)amino)benzoate

A

benzoic acid methyl ester
93-58-3

benzoic acid methyl ester

B

4-nitrobenzoic acid methyl ester
619-50-1

4-nitrobenzoic acid methyl ester

C

diphenic acid dimethyl ester
5807-64-7

diphenic acid dimethyl ester

D

dimethyl (1,1'-biphenyl)-2,4'-dicarboxylate
55676-77-2

dimethyl (1,1'-biphenyl)-2,4'-dicarboxylate

E

dimethyl (1,1'-biphenyl)-2,3'-dicarboxylate
32947-58-3

dimethyl (1,1'-biphenyl)-2,3'-dicarboxylate

F

2-(benzoyl-methylamino)benzoic acid methyl ester
75541-61-6

2-(benzoyl-methylamino)benzoic acid methyl ester

G

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

H

Methyl N-methylanthranilate
85-91-6

Methyl N-methylanthranilate

I

methyl 2-(benzamido)benzoate
7510-49-8

methyl 2-(benzamido)benzoate

J

N-formylanthranilic acid methyl ester
41270-80-8

N-formylanthranilic acid methyl ester

Conditions
ConditionsYield
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
methanol
67-56-1

methanol

ethyl 2-nitrobenzoate
610-34-4

ethyl 2-nitrobenzoate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With samarium; iodine In methanol for 5h; Heating;86%
anthranilic acid
118-92-3

anthranilic acid

methyl salicylate
119-36-8

methyl salicylate

A

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

B

salicylic acid
69-72-7

salicylic acid

Conditions
ConditionsYield
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
anthranilic acid
118-92-3

anthranilic acid

methyl iodide
74-88-4

methyl iodide

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With potassium carbonate In acetone for 1h; Heating;82%
methyl 2-(3,3-diisopropylureido)benzoate
1150096-69-7

methyl 2-(3,3-diisopropylureido)benzoate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With water for 18h; Reflux;80%
2-(1-acetoxymethyl-3-ethoxycarbonylpropylazo)benzoic acid methyl ester
916811-64-8

2-(1-acetoxymethyl-3-ethoxycarbonylpropylazo)benzoic acid methyl ester

A

4-acetylamino-5-hydroxypentanoic acid ethyl ester

4-acetylamino-5-hydroxypentanoic acid ethyl ester

B

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With hydrogen; nickel In methanol under 37503 Torr; for 3h;A 79%
B n/a
methanol
67-56-1

methanol

phthalimide
136918-14-4

phthalimide

A

methyl 2-((methoxycarbonyl)amino)benzoate
7143-42-2

methyl 2-((methoxycarbonyl)amino)benzoate

B

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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%
anthranilic acid
118-92-3

anthranilic acid

dimethyl sulfate
77-78-1

dimethyl sulfate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With potassium carbonate In acetone for 3h; Reflux; Inert atmosphere;77%
o-iodo-methyl-benzoic acid
610-97-9

o-iodo-methyl-benzoic acid

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
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%
methanol
67-56-1

methanol

anthranilic acid amide
28144-70-9

anthranilic acid amide

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With thionyl chloride at 0 - 55℃; for 6h;75%
methanol
67-56-1

methanol

2-nitro-benzaldehyde
552-89-6

2-nitro-benzaldehyde

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With dmap; ethyl 2-cyanoacetate at 20℃; for 4.5h; chemoselective reaction;73%
methanol
67-56-1

methanol

2-azidobenzoic acid
31162-13-7

2-azidobenzoic acid

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With samarium; iodine for 6h; Ambient temperature;70%
methyl 2-isothiocyanatobenzoate
16024-82-1

methyl 2-isothiocyanatobenzoate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

Conditions
ConditionsYield
With 3,4-dimercaptotoluene; sodium hydrogencarbonate In methanol at 25℃; for 2h;69%
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

methyl N-tosylanthranilate
50998-74-8

methyl N-tosylanthranilate

Conditions
ConditionsYield
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
134-20-3

2-carbomethoxyaniline

3,4-dimethoxybenzoic acid chloride
3535-37-3

3,4-dimethoxybenzoic acid chloride

methyl N-(3,4-dimethoxybenzoyl)anthranilate
67836-52-6

methyl N-(3,4-dimethoxybenzoyl)anthranilate

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 0.5h;100%
pivaloyl chloride
3282-30-2

pivaloyl chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl N-trimethylacetylanthranilate
84540-62-5

methyl N-trimethylacetylanthranilate

Conditions
ConditionsYield
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
638-29-9

n-valeryl chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(valerylamino)benzoate
136304-94-4

methyl 2-(valerylamino)benzoate

Conditions
ConditionsYield
With triethylamine In chloroform at 0℃; for 4h;100%
With potassium carbonate In benzene Heating;82%
methyl thioisocyanate
556-61-6

methyl thioisocyanate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

2-mercapto-3-methyl-3,4-dihydroquinazolin-4-one
1705-09-5

2-mercapto-3-methyl-3,4-dihydroquinazolin-4-one

Conditions
ConditionsYield
In neat (no solvent) for 72h; Ambient temperature;100%
Benzoyl isothiocyanate
532-55-8

Benzoyl isothiocyanate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

2-(3-Benzoylthioureido)benzoesaeuremethylester
77711-35-4

2-(3-Benzoylthioureido)benzoesaeuremethylester

Conditions
ConditionsYield
In neat (no solvent) Ambient temperature;100%
2-chloroethyl isothiocyanate
1943-83-5

2-chloroethyl isothiocyanate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-<3-(2-chloroethyl)ureido>benzoate
77093-92-6

methyl 2-<3-(2-chloroethyl)ureido>benzoate

Conditions
ConditionsYield
for 16h; Ambient temperature;100%
ethoxyacetyl chloride
14077-58-8

ethoxyacetyl chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl (2-ethoxyacetamido)benzoate
134017-46-2

methyl (2-ethoxyacetamido)benzoate

Conditions
ConditionsYield
With potassium carbonate In benzene Heating;100%
With triethylamine In dichloromethane92.8%
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

isopentanoyl chloride
108-12-3

isopentanoyl chloride

2-(3-Methyl-butyrylamino)-benzoic acid methyl ester
84604-44-4

2-(3-Methyl-butyrylamino)-benzoic acid methyl ester

Conditions
ConditionsYield
With potassium carbonate In benzene Heating;100%
With sodium hydrogencarbonate In tetrahydrofuran
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-nitrobenzoate
606-27-9

methyl 2-nitrobenzoate

Conditions
ConditionsYield
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
32315-10-9

bis(trichloromethyl) carbonate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-isocyanatobenzoate
1793-07-3

methyl 2-isocyanatobenzoate

Conditions
ConditionsYield
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
547739-67-3

3-chlorosulfonyl-4-methylbenzoic acid chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(3-(chlorosulfonyl)-4-methylbenzamido)benzoate

methyl 2-(3-(chlorosulfonyl)-4-methylbenzamido)benzoate

Conditions
ConditionsYield
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
64527-19-1

2-(4-acetamidophenylsulfonamido)-4-methylpentanoic acid

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(2-(4-acetamidophenylsulfonamido)-4-methylpentanamido)benzoate

methyl 2-(2-(4-acetamidophenylsulfonamido)-4-methylpentanamido)benzoate

Conditions
ConditionsYield
With phosphorus trichloride under 760.051 Torr; Heating;100%
2-(4-acetamidophenylsulfonamido)propanoic acid
64527-17-9

2-(4-acetamidophenylsulfonamido)propanoic acid

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(2-(4-acetamidophenylsulfonamido)propanamido)benzoate

methyl 2-(2-(4-acetamidophenylsulfonamido)propanamido)benzoate

Conditions
ConditionsYield
With phosphorus trichloride Heating;100%
Nα-(4-acetamidobenzenesulfonyl)-L-phenylalanine

Nα-(4-acetamidobenzenesulfonyl)-L-phenylalanine

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(2-(4-acetamidophenylsulfonamido)-3-phenylpropanamido)benzoate

methyl 2-(2-(4-acetamidophenylsulfonamido)-3-phenylpropanamido)benzoate

Conditions
ConditionsYield
With phosphorus trichloride100%
methyl chloroformate
79-22-1

methyl chloroformate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-((methoxycarbonyl)amino)benzoate
7143-42-2

methyl 2-((methoxycarbonyl)amino)benzoate

Conditions
ConditionsYield
In toluene for 8h; Inert atmosphere; Reflux;99%
In toluene for 8h; Reflux;88%
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

2-amino-3,5-dibromo-benzoic acid methyl ester
606-00-8

2-amino-3,5-dibromo-benzoic acid methyl ester

Conditions
ConditionsYield
With bromine; sodium hydrogensulfite In dichloromethane; acetic acid99%
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
134-20-3

2-carbomethoxyaniline

Glycine ethyl ester isocyanate
2949-22-6

Glycine ethyl ester isocyanate

N-(carbamoyl)glycinaethylester
78754-93-5

N-(carbamoyl)glycinaethylester

Conditions
ConditionsYield
for 16h; Ambient temperature;99%
2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

dianthranilide
15351-42-5

dianthranilide

Conditions
ConditionsYield
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
24424-99-5

di-tert-butyl dicarbonate

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-((tert-butoxycarbonyl)amino)benzoate

methyl 2-((tert-butoxycarbonyl)amino)benzoate

Conditions
ConditionsYield
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
292638-85-8

acrylic acid methyl ester

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

2-(E)-[2-methoxycarbonylphenyl]acrylic acid methylester
34288-40-9, 63600-27-1, 18454-56-3

2-(E)-[2-methoxycarbonylphenyl]acrylic acid methylester

Conditions
ConditionsYield
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
61592-89-0

2,2’-dibromodiphenylmethane

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

2-(anthracen-9-yl)aniline
1252763-38-4

2-(anthracen-9-yl)aniline

Conditions
ConditionsYield
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%
cyclohexanone
108-94-1

cyclohexanone

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(cyclohexylamino)benzoate
10286-54-1

methyl 2-(cyclohexylamino)benzoate

Conditions
ConditionsYield
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
85-44-9

phthalic anhydride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl 2-(1,3-dioxoisoindolin-2-yl)benzoate
19688-99-4

methyl 2-(1,3-dioxoisoindolin-2-yl)benzoate

Conditions
ConditionsYield
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
79-04-9

chloroacetyl chloride

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

methyl N-(chloroacetyl)anthranilate
58915-18-7

methyl N-(chloroacetyl)anthranilate

Conditions
ConditionsYield
With potassium carbonate In acetone at 20℃; for 4h;98%
With sodium hydrogencarbonate In tetrahydrofuran; water96%
In benzene Heating;95%
formaldehyd
50-00-0

formaldehyd

2-carbomethoxyaniline
134-20-3

2-carbomethoxyaniline

N,N'-methanediyl-di-anthranilic acid dimethyl ester
21038-62-0

N,N'-methanediyl-di-anthranilic acid dimethyl ester

Conditions
ConditionsYield
In water98%

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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