Methyl anthranilate

Base Information

• Chemical Name: Methyl anthranilate
• CAS No.: 134-20-3
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.165
• Hs Code.: 2922.49
• European Community (EC) Number: 205-132-4
• NSC Number: 3109
• UNII: 981I0C1E5W
• DSSTox Substance ID: DTXSID6025567
• Nikkaji Number: J2.018D
• Wikipedia: Methyl anthranilate
• Wikidata: Q420894
• RXCUI: 29742
• Metabolomics Workbench ID: 43994
• ChEMBL ID: CHEMBL1493986
• Mol file: 134-20-3.mol

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;

Chemical Property of Methyl anthranilate

Chemical Property:

• Appearance/Colour: colorless to light yellow liquid with a smell of orange blossom
• Vapor Pressure: 1 mm Hg ( 20 °C)
• Melting Point: 24 °C(lit.)
• Refractive Index: 1.582 - 1.584
• Boiling Point: 256 °C at 760 mmHg
• PKA: pK1:2.23(＋1) (25°C)
• Flash Point: 112.9 °C
• PSA: 52.32000
• Density: 1.166 g/cm³
• LogP: 1.63660
• Storage Temp.: -20°C Freezer
• Sensitive.: Air Sensitive
• Solubility.: alcohol: freely soluble(lit.)
• Water Solubility.: slightly soluble
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 151.063328530
• Heavy Atom Count: 11
• Complexity: 147

Purity/Quality:

99% ^*data from raw suppliers

Methyl anthranilate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Aminobenzoic Acids
• Canonical SMILES: COC(=O)C1=CC=CC=C1N
• 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.
• 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.

Technology Process of Methyl anthranilate

There total 81 articles about Methyl anthranilate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

methyl 2-nitrobenzoate (606-27-9) → 2-carbomethoxyaniline (134-20-3)

Guidance literature:

With potassium fluoride; polymethylhydrosiloxane; palladium diacetate; In tetrahydrofuran; water; at 20 ℃; for 0.5h;

DOI:10.1021/ol052120n

Reference yield: 99.0%

5-methoxy-3H-1,4-benzodiazepine (107468-21-3) → 2-carbomethoxyaniline (134-20-3)

Guidance literature:

In 1,4-dioxane; water; for 2h; Heating;

Reference yield: 98.0%

2-azido-benzoic acid methyl ester (16714-23-1) → 2-carbomethoxyaniline (134-20-3)

Guidance literature:

With chloro-trimethyl-silane; sodium iodide; In acetonitrile; for 0.0833333h; Ambient temperature;

DOI:10.1016/S0040-4039(97)01628-6

upstream raw materials:

diazomethane

anthranilic acid

methanol

isatoic anhydride

Downstream raw materials:

N,N-bis-(2-hydroxy-ethyl)-anthranilic acid methyl ester

methyl 2-(2-hydroxyethylamino)benzoate

N-(2-mercapto-ethyl)-anthranilic acid methyl ester

2-(3-phenyl-triazenyl)-benzoic acid methyl ester

Refernces

• 1、 Li, Huan,Yang, Hengquan,Zhang, Fengwei,Zhang, Xian-Ming,Zhao, Chao,Chen, Shuai. "In situ mosaic strategy generated Co-based N-doped mesoporous carbon for highly selective hydrogenation of nitroaromatics". . p. 212 - 222. Retrieved 2017.
• 2、 Van Haandel, Marjon J. H.,Saraber, Florence C. E.,Boersma, Marelle G.,Laane, Colja,Fleming, Yvette,Weenen, Hugo,Rietjens, Ivonne M. C. M.. "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". . p. 1949 - 1954. Retrieved 2000.
• 3、 Xia, Hanxue,Zhang, Yong,Pavlov, Julius,Jariwala, Freneil B.,Attygalle, Athula B.. "Competitive homolytic and heterolytic decomposition pathways of gas-phase negative ions generated from aminobenzoate esters". . p. 245 - 253. Retrieved 2016.
• 4、 Yadav,Krishnan. "An ecofriendly catalytic route for the preparation of perfumery grade methyl anthranilate from anthranilic acid and methanol". . p. 86 - 95. Retrieved 1998.
• 5、 Li, Jingjing,Chen, Shuai,Liu, Mengmeng,Li, Zhihong,Dong, Zhengping,Zhang, Fengwei,Zhang, Xian-Ming. "Self-Template Construction of High-Performance Co, N-Decorated Carbon Nanotubes from a Novel Cobalt Dicyandiamide Molecule". . p. 2609 - 2617. Retrieved 2021.
• 6、 Banik, Bimal K.,Mukhopadhyay, Chhanda,Venkatraman,Becker, Frederick F.. "A facile reduction of aromatic nitro compounds to aromatic amines by samarium and iodine". . p. 7243 - 7246. Retrieved 1998.
• 7、 Cohen,Tirpak. "-". . p. 143,144,146. Retrieved 1975.
• 8、 Trecker et al.. "-". . p. 1034. Retrieved 1968.
• 9、 Taupp, Marcus,Harmsen, Dag,Heckel, Frank,Schreier, Peter. "Production of natural methyl anthranilate by microbial N-demethylation of N-methyl methyl anthranilate by the topsoil-isolated bacterium Bacillus megaterium". . p. 9586 - 9589. Retrieved 2005.
• 10、 Miltojevi?, Ana B.,Radulovi?, Niko S.. "Structural elucidation of thermolysis products of methyl N-methyl-N-nitrosoanthranilate". . p. 53569 - 53585. Retrieved 2015.