Ethyl anthranilate

Base Information

• Chemical Name: Ethyl anthranilate
• CAS No.: 87-25-2
• Molecular Formula: C9H11NO2
• Molecular Weight: 165.192
• Hs Code.: 29224999
• European Community (EC) Number: 201-735-1
• NSC Number: 4146
• UNII: 38Y050IUE4
• DSSTox Substance ID: DTXSID6025272
• Nikkaji Number: J4.276E
• Wikidata: Q27256834
• Metabolomics Workbench ID: 46120
• ChEMBL ID: CHEMBL1332922
• Mol file: 87-25-2.mol

Synonyms:ethyl anthranilate

Chemical Property of Ethyl anthranilate

Chemical Property:

• Appearance/Colour: colourless liquid
• Vapor Pressure: 0.00954mmHg at 25°C
• Melting Point: 13-15 °C(lit.)
• Refractive Index: n20/D 1.564(lit.)
• Boiling Point: 264.7 °C at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 126.5 °C
• PSA: 52.32000
• Density: 1.13 g/cm³
• LogP: 2.02670
• Storage Temp.: Store below +30°C.
• Solubility.: Insoluble in water but soluble in organic solvents
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 165.078978594
• Heavy Atom Count: 12
• Complexity: 159

Purity/Quality:

99.9% ^*data from raw suppliers

Ethyl Anthranilate >99.0%(GC) ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Aminobenzoic Acids
• Canonical SMILES: CCOC(=O)C1=CC=CC=C1N
• Uses: Ethyl 2-aminobenzoate is used as a reactant in the amination of aryl chlorides, bromides, and triflates. Perfumery and flavors, similar to methyl anthranilate.

Technology Process of Ethyl anthranilate

There total 43 articles about Ethyl 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: 98.0%

boron trifluoride diethyl etherate (109-63-7) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 2-ethoxycarbonylaniline (87-25-2)

Guidance literature:

at 120 ℃; for 4h;

DOI:10.4314/bcse.v32i2.16

Reference yield: 89.0%

isatoic anhydride (118-48-9) + ethanol (64-17-5) → 2-ethoxycarbonylaniline (87-25-2)

Guidance literature:

With sodium hydride; In mineral oil; for 2h; Reflux; Inert atmosphere;

DOI:10.1016/j.carres.2012.08.001

Reference yield: 82.0%

o-azidobenzoic acid ethyl ester (90408-05-2) → 2-ethoxycarbonylaniline (87-25-2)

Guidance literature:

With sodium tetrahydroborate; nickel(II) chloride hexahydrate; In methanol; at 20 ℃; for 3h; Sealed tube; Darkness;

DOI:10.1055/a-1579-2190

upstream raw materials:

phthalimide

isatoic anhydride

ethanol

2-amino-cyclohex-3-enecarboxylic acid ethyl ester

Downstream raw materials:

2-amino-N-(2-morpholin-4-yl-ethyl)-benzamide

N-(2-amino-6-methyl-pyrimidin-4-yl)-anthranilic acid ethyl ester

N-(4-amino-6-methyl-pyrimidin-2-yl)-anthranilic acid ethyl ester

2-{[(8-hydroxyquinolin-7-yl)phenylmethyl]amino}benzoic acid ethyl ester

Refernces

• 1、 Liu, Jie,Zhang, Guang-Yu,Zhang, Zhe,Li, Bo,Chai, Fei,Wang, Qi,Zhou, Zi-Dan,Xu, Ling-Ling,Wang, Shou-Kai,Jin, Zhen,Tang, You-Zhi. "Design, synthesis, in vitro and in vivo evaluation against MRSA and molecular docking studies of novel pleuromutilin derivatives bearing 1, 3, 4-oxadiazole linker". . . Retrieved 2021/05/17.
• 2、 Begam, Hasina Mamataj,Jana, Ranjan,Manna, Kartic,Samanta, Krishanu. "Overcoming the Deallylation Problem: Palladium(II)-Catalyzed Chemo-, Regio-, and Stereoselective Allylic Oxidation of Aryl Allyl Ether, Amine, and Amino Acids". supporting information. p. 7443 - 7449. Retrieved 2020/10/09.