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:

9-(3t-carboxy-acryloyloximethyl)-3,8-dihydroxy-4-[(2-methoxycarbonyl-phenylimino)-methyl]-1,6-dimethyl-11-oxo-11H-dibenzo[b,e][1,4]dioxepin-7-carboxylic acid

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

methyl 2-(2-hydroxyethylamino)benzoate

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

Refernces

Synthesis and spectroscopic properties of Ni(II) complexes of some aroyl hydrazone ligands with 2,6-diacetyl pyridine monooxime: X-ray crystal structure of the salicyloylhydrazone Ni(II) complex

10.1016/j.ica.2010.05.009

The study focuses on the synthesis and characterization of five new Ni(II) complexes with aroyl hydrazone ligands derived from 2,6-diacetyl pyridine monooxime. The complexes were found to have a distorted octahedral N4O2 coordination environment around the Ni(II) ion, with the ligands coordinating through the pyridine nitrogen, imino-hydrazone nitrogen, and the deprotonated oxygen of the hydrazone moiety. The uncoordinated iminooxime groups and the orthogonal orientation of the CH3–C@N–OH groups relative to the adjacent pyridine rings were observed. The ligands and their corresponding Ni(II) complexes exhibited luminescence, with the complexes showing a lower quantum yield compared to the free ligands. The study also includes the X-ray crystal structure of the Ni(II) salicyloylhydrazone complex, which revealed details about the molecular structure and hydrogen bonding interactions in the crystal lattice. The research provides insights into the coordination chemistry of aroyl hydrazone ligands and their potential applications in areas such as pharmaceuticals and materials science.

Synthesis and mass spectrum characterization of lyrame schiff base for synthetic ingredients in perfumes industry

10.13005/ojc/340657

The study focuses on the synthesis and mass spectrum characterization of Lyrame Schiff base, a synthetic precursor used in the perfume industry to enhance fragrance stability and longevity. Lyrame is synthesized through a simple condensation reaction between lyral and methyl anthranilate. Lyral, an aldehyde compound, reacts with methyl anthranilate, an amine trapping agent, to form Lyrame Schiff base and water as a by-product. The study investigates the color of the Lyrame product, which is influenced by the synthesis time and the concentration of methyl anthranilate. The chemical structure of Lyrame is confirmed using gas chromatography-mass spectrometry (GC-MS). The mass fragmentation pattern of Lyrame is analyzed to ensure its successful synthesis. The study concludes that Lyrame Schiff base can be effectively synthesized using the simple condensation method, and its molecular structure is confirmed through GC-MS analysis.