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High quality Methyl Anthranilate supplier in China
Cas No: 134-20-3
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Methyl anthranilate
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Methyl anthranilate CAS NO.134-20-3
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Methyl 2-aminobenzoate
Cas No: 134-20-3
USD $ 5.0-5.0 / Kilogram 1 Kilogram 1000 Kilogram/Month Enke Pharma-tech Co.,Ltd. (Cangzhou, China ) Contact Supplier
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Methyl anthranilate
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2-amino-5-methylbenzoic acid methyl ester
Cas No: 134-20-3
No Data 10 Milligram Amadis Chemical Co., Ltd. Contact Supplier

134-20-3 Usage

Description

Methyl anthranilate, also known as MA, methyl 2-amino benzoate or carbo methoxy aniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2.

Chemical Properties

Methyl anthranilate has a characteristic orange-flower odor and a slightly bitter, pungent taste. May be prepared by heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.

Chemical Properties

Methyl Anthranilate occurs in a large number of blossom essential oils (e.g., neroli, ylang-ylang, and jasmine oils), grapes, and citrus oils. It occurs as white crystals (mp 24–25°C), or a yellowish liquid, that show blue fluorescence and have an orange blossom odor. Methyl anthranilate is prepared by esterification of anthranilic acid with methanol or by reaction of isatoic anhydride with methanol.It is used in a large number of blossom fragrances. However, its use in perfumes for soaps and cosmetics is limited because it causes discoloration. It is used in flavor compositions (e.g., in grape and citrus flavors).

Occurrence

Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes or hybrids thereof, and in bergamot, black locust, champaca , gardenia, jasmine, lemon, mandarin, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate.It is also secreted by the musk glands of foxes and dogs, and lends a "sickly sweetness" to the smell of rotting flesh.

Uses

Methyl anthranilate acts as a bird repellent. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and golf courses. Dimethyl anthranilate (DMA) has a similar effect. It is also used for the flavor of grape Kool Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs. Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery . It is also used to produce Schiff's Bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol - produced by combining methyl anthranilate and hydroxyl citronellal.

Definition

ChEBI: Methyl anthranilate is a benzoate ester that is the methyl ester of anthranilic acid. It has a role as a metabolite and a flavouring agent. It derives from an anthranilic acid.

Preparation

By heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.

Synthesis Reference(s)

Tetrahedron Letters, 33, p. 3599, 1992 DOI: 10.1016/S0040-4039(00)92512-7

General Description

Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence.

Air & Water Reactions

Methyl anthranilate is sensitive to air and light. Slightly water soluble .

Reactivity Profile

An amine and ester. Amines are chemical bases. They neutralize acids to form salts plus water. These acid-base reactions are exothermic. The amount of heat that is evolved per mole of amine in a neutralization is largely independent of the strength of the amine as a base. Amines may be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated by amines in combination with strong reducing agents, such as hydrides. Esters react with acids to liberate heat along with alcohols and acids. Strong oxidizing acids may cause a vigorous reaction that is sufficiently exothermic to ignite the reaction products. Heat is also generated by the interaction of esters with caustic solutions. Flammable hydrogen is generated by mixing esters with alkali metals and hydrides.

Fire Hazard

Methyl anthranilate is combustible.

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. A skin irritant. See also ESTERS. Combustible liquid. When heated to decomposition it emits toxic fumes of NOx.

Toxicology

Methyl anthranilate is a colorless liquid that has a sweet, fruity, grape-like flavor. It is found in the essential oils of orange, lemon, and jasmine and has been widely used to create imitation Concord grape flavor. Table 10.8 shows the acute toxicity of methyl anthranilate. Methyl anthranilate promotes some allergic reactions on human skin, which has led to it being prohibited for use in cosmetic products.

Metabolism

It is probable that this ester is hydrolysed and the anthranilate is excreted mostly as oaminobenzoyl glucuronide (Charconnet-Harding, Dalgliesh & Neuberger, 1953).

Toxicity evaluation

Even though MA is palatable to humans, it is an irritant to birds. The bird-repellent properties of MA and related compounds were discovered in the late 1950s (25). The mode of action is via the trigeminal nerve. Thus, all avian species tested so far perceive MA as an irritant, not as a taste repellent per se.
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

Brand (Code)Product description CAS number Packaging Price Detail
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%

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