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Methyl anthranilate is a chemical with a specific purpose. Lookchem provides you with multiple data and supplier information of this chemical.

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  • 134-20-3 Structure
  • Basic information

    1. Product Name: Methyl anthranilate
    2. Synonyms: NEROLI;NEROLI OIL, ARTIFICIAL;2-AMINOBENZOIC ACID METHYL ESTER;ANTHRANILIC ACID METHYL ESTER;ANTHRANILIC ACID:METHYL ESTER;METHYL 2-ANTHRANILATE;METHYL 2-AMINOBENZOATE;METHYL O-AMINOBENZOATE
    3. CAS NO:134-20-3
    4. Molecular Formula: C8H9NO2
    5. Molecular Weight: 151.16
    6. EINECS: 205-132-4
    7. Product Categories: CARBOXYLICESTER;Benzene derivatives;Aromatic Esters;pharmacetical;Aromatics;Building Blocks;C8 to C9;Carbonyl Compounds;Chemical Synthesis;Citrus aurantium (Seville orange);Esters;Nutrition Research;Organic Building Blocks;Phytochemicals by Plant (Food/Spice/Herb);Flavor;Halogenated Heterocycles ,Pyrimidines
    8. Mol File: 134-20-3.mol
    9. Article Data: 138
  • Chemical Properties

    1. Melting Point: 24 °C(lit.)
    2. Boiling Point: 256 °C(lit.)
    3. Flash Point: 220 °F
    4. Appearance: Clear yellow-brown/Liquid
    5. Density: 1.168 g/mL at 25 °C(lit.)
    6. Vapor Pressure: 1 mm Hg ( 20 °C)
    7. Refractive Index: n20/D 1.582(lit.)
    8. Storage Temp.: -20°C Freezer
    9. Solubility: alcohol: freely soluble(lit.)
    10. PKA: pK1:2.23(+1) (25°C)
    11. Explosive Limit: 1.4-7.8%(V)
    12. Water Solubility: slightly soluble
    13. Sensitive: Air Sensitive
    14. Stability: Stable. Combustible. Incompatible with strong oxidizing agents.
    15. Merck: 14,6020
    16. BRN: 606965
    17. CAS DataBase Reference: Methyl anthranilate(CAS DataBase Reference)
    18. NIST Chemistry Reference: Methyl anthranilate(134-20-3)
    19. EPA Substance Registry System: Methyl anthranilate(134-20-3)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38
    3. Safety Statements: 26-36-37/39
    4. WGK Germany: 1
    5. RTECS: CB3325000
    6. F: 21
    7. TSCA: Yes
    8. HazardClass: N/A
    9. PackingGroup: N/A
    10. Hazardous Substances Data: 134-20-3(Hazardous Substances Data)

134-20-3 Usage

Chemical Description

Methyl anthranilate is an organic compound with a floral odor.

Check Digit Verification of cas no

The CAS Registry Mumber 134-20-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,3 and 4 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 134-20:
(5*1)+(4*3)+(3*4)+(2*2)+(1*0)=33
33 % 10 = 3
So 134-20-3 is a valid CAS Registry Number.
InChI:InChI=1/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3

134-20-3 Well-known Company Product Price

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  • Alfa Aesar

  • (A15681)  Methyl anthranilate, 99%   

  • 134-20-3

  • 250g

  • 234.0CNY

  • Detail
  • Alfa Aesar

  • (A15681)  Methyl anthranilate, 99%   

  • 134-20-3

  • 500g

  • 397.0CNY

  • Detail
  • Alfa Aesar

  • (A15681)  Methyl anthranilate, 99%   

  • 134-20-3

  • 1000g

  • 526.0CNY

  • Detail

134-20-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Methyl anthranilate

1.2 Other means of identification

Product number -
Other names nerolioil,artifical

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Food additives -> Flavoring Agents
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:134-20-3 SDS

134-20-3Synthetic 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%

134-20-3Related news

Methyl anthranilate (cas 134-20-3) in Citrus honey. Analytical method and suitability as a chemical marker09/30/2019

The present work describes a method for the determination of methyl anthranilate (MA) in honey, and reports the results of a study carried out on 46 Citrus honey samples produced in different countries. The MA content was measured, and the compliance of the samples with the unifloral Citrus hone...detailed

The MYB transcription factor Emission of Methyl anthranilate (cas 134-20-3) 1 stimulates emission of Methyl anthranilate (cas 134-20-3) from Medicago truncatula hairy roots09/29/2019

Plants respond to herbivore or pathogen attacks by activating specific defense programs that include the production of bioactive specialized metabolites to eliminate or deter the attackers. Volatiles play an important role in the interaction of a plant with its environment. Through transcript pr...detailed

Innovative and high performance synthesis of microcapsules containing Methyl anthranilate (cas 134-20-3) by microsuspension iodine transfer polymerization10/01/2019

In this research, preparations of polymer microcapsule encapsulated methyl anthranilate (MA) as an essential oil model by both microsuspension conventional radical polymerization (ms CRP) and microsuspension iodine transfer polymerization (ms ITP) using methyl methacrylate (MMA) and ethylene gly...detailed

134-20-3Relevant articles and documents

Selective synthesis of Rh5 carbonyl clusters within a polyamine dendrimer for chemoselective reduction of nitro aromatics

Maeno, Zen,Mitsudome, Takato,Mizugaki, Tomoo,Jitsukawa, Koichiro,Kaneda, Kiyotomi

, p. 6526 - 6529 (2014)

The selective synthesis of the [Rh5(CO)15] - cluster within the PPI dendrimer was successfully demonstrated. The dendrimer-encapsulated [Rh5(CO)15]- was resistant to decomposition under the catalytic reaction conditions and exhibited extremely high selectivity for the chemoselective reduction of nitro groups of various nitro aromatics with other reducible groups using CO/H2O as a reductant. This journal is the Partner Organisations 2014.

In situ mosaic strategy generated Co-based N-doped mesoporous carbon for highly selective hydrogenation of nitroaromatics

Li, Huan,Yang, Hengquan,Zhang, Fengwei,Zhang, Xian-Ming,Zhao, Chao,Chen, Shuai

, p. 212 - 222 (2017)

The development of heterogeneous non-noble metal catalytic architectures that can realize the high selective and stable hydrogenation of nitroaromatics under mild conditions is a profound challenge in the catalysis community. Here we report a facile synthesis of highly nitrogen doped and uniformly embedded Co-based mesoporous carbon catalyst through a thermolysis and etching combined strategy, in which the commercial cobalt phthalocyanine and colloidal silica serve as precursor and hard template, respectively. The protocol allows for simultaneous optimization of porous features and cobalt nanoparticles of N-doped mesoporous carbon catalyst by fine-tuning thermolysis temperature. Among the as-prepared catalysts, Co@NMC-800 with lower dosage of cobalt exhibits outstanding catalytic activity and chemoselectivity for various nitroaromatics under mild condition (2.0?mol% Co, 1.0?MPa H2, 80?°C, xand Co NPs surface wrapped thin carbon layers plays a crucial role in providing the excellent selectivity for hydrogenation of vulnerable nitroaromatics via preferential adsorption of polar nitro group.

Nickel Boride Reduction of Aryl Nitro Compounds

Seltzman, Herbert H.,Berrang, Bertold D.

, p. 3083 - 3086 (1993)

Nickel boride smoothly reduces aryl nitro compounds to the corresponding anilines in the presence of iodo and ortho carboalkoxy groups in contrast to the problematic reductions by other methods.

Characterization of different commercial soybean peroxidase preparations and use of the enzyme for N-demethylation of methyl N-methylanthranilate to produce the food flavor methylanthranilate

Van Haandel, Marjon J. H.,Saraber, Florence C. E.,Boersma, Marelle G.,Laane, Colja,Fleming, Yvette,Weenen, Hugo,Rietjens, Ivonne M. C. M.

, p. 1949 - 1954 (2000)

The potential of different peroxidase preparations for the N- demethylation of methyl N-methylanthranilate to produce the food flavor methylanthranilate (MA) was investigated. All tested peroxidase preparations were able to catalyze the N-dealkylation. The tested soybean preparations vary widely with respect to their heme content. Furthermore, the operational stability of purified soybean peroxidase (SP) is at least 25-fold lower than that of horseradish peroxidase and only 5-fold higher than that of microperoxidase 8. Thus, the presence of a large protein chain around a porphyrin cofactor in a peroxidase is, by itself, insufficient to explain the observed differences in operational stability. Despite its relatively low operational stability, SP proved to be the most efficient biocatalyst for the production of MA with high yield and purity, especially observed at the high temperature and low pH values at which SP appeared to be optimally active.

Competitive homolytic and heterolytic decomposition pathways of gas-phase negative ions generated from aminobenzoate esters

Xia, Hanxue,Zhang, Yong,Pavlov, Julius,Jariwala, Freneil B.,Attygalle, Athula B.

, p. 245 - 253 (2016)

An alkyl-radical loss and an alkene loss are two competitive fragmentation pathways that deprotonated aminobenzoate esters undergo upon activation under mass spectrometric conditions. For the meta and para isomers, the alkyl-radical loss by a homolytic cleavage of the alkyl-oxygen bond of the ester moiety is the predominant fragmentation pathway, while the contribution from the alkene elimination by a heterolytic pathway is less significant. In contrast, owing to a pronounced charge-mediated ortho effect, the alkene loss becomes the predominant pathway for the ortho isomers of ethyl and higher esters. Results from isotope-labeled compounds confirmed that the alkene loss proceeds by a specific γ-hydrogen transfer mechanism that resembles the McLafferty rearrangement for radical cations. Even for the para compounds, if the alkoxide moiety bears structural motifs required for the elimination of a more stable alkene molecule, the heterolytic pathway becomes the predominant pathway. For example, in the spectrum of deprotonated 2-phenylethyl 4-aminobenzoate, m/z 136 peak is the base peak because the alkene eliminated is styrene. Owing to the fact that all deprotonated aminobenzoate esters, irrespective of the size of the alkoxy group, upon activation fragment to form an m/z 135 ion, aminobenzoate esters in mixtures can be quantified by precursor ion discovery mass spectrometric experiments.

Novel VEGFR-2 inhibitors with an N-acylhydrazone scaffold

Pauli, Fernanda P.,Martins, Juliana R.,Paschoalin, Thaysa,Ionta, Marisa,Barbosa, Maria Leticia C.,Barreiro, Eliezer J.

, (2020)

Vascular endothelial growth factor receptor 2 (VEGFR-2) is a tyrosine kinase that mediates a large number of cell responses associated with angiogenesis. The control of the angiogenic pathway in tumorigenesis by the inhibition of VEGFR-2 is considered a p

An ecofriendly catalytic route for the preparation of perfumery grade methyl anthranilate from anthranilic acid and methanol

Yadav,Krishnan

, p. 86 - 95 (1998)

Methyl anthranilate is a very important perfumery ester and also a precursor to a number of Schiff bases which are used in several fragrance formulations. The current practice is to use homogeneous acids as catalysts in the manufacture of methyl anthranil

Reductive carbodiazenylation of nonactivated olefins via aryl diazonium salts

Heinrich, Markus R.,Blank, Olga,Woelfel, Sabrina

, p. 3323 - 3325 (2006)

The reduction of aryl diazonium salts in the presence of nonactivated olefins provides rapid entry to carbodiazenylation products. The regioselective functionalization of double bonds is achieved in a one-pot process starting from aniline derivatives. Car

Self-Template Construction of High-Performance Co, N-Decorated Carbon Nanotubes from a Novel Cobalt Dicyandiamide Molecule

Li, Jingjing,Chen, Shuai,Liu, Mengmeng,Li, Zhihong,Dong, Zhengping,Zhang, Fengwei,Zhang, Xian-Ming

, p. 2609 - 2617 (2021)

N-doped carbon nanotubes (NCNTs) based composites have shown great prospect in catalysis relevant communities, which are often evolved from commercial CNTs and nitrogenous hybrid precursors. However, the direct fabrication of high-performance and non-nobl

A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine

Banik, Bimal K.,Mukhopadhyay, Chhanda,Venkatraman,Becker, Frederick F.

, p. 7243 - 7246 (1998)

A simple method for the reduction of aromatic nitro compounds to aromatic amines was developed using samarium and catalytic amounts of iodine.

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