Allyl anthranilate

Base Information

• Chemical Name: Allyl anthranilate
• CAS No.: 7493-63-2
• Molecular Formula: C10H11NO2
• Molecular Weight: 177.203
• Hs Code.: 2922498050
• European Community (EC) Number: 231-331-0
• NSC Number: 147476
• UNII: 81T0041N82
• DSSTox Substance ID: DTXSID3024441
• Nikkaji Number: J180.744G
• Wikidata: Q27269266
• Metabolomics Workbench ID: 47883
• ChEMBL ID: CHEMBL1606698
• Mol file: 7493-63-2.mol

Synonyms:ALLYL ANTHRANILATE;7493-63-2;Allyl 2-aminobenzoate;prop-2-enyl 2-aminobenzoate;2-Propenyl 2-aminobenzoate;Anthranilic acid, allyl ester;Allyl O-aminobenzoate;2-Propen-1-yl anthranilate;Vinyl carbinyl anthranilate;Benzoic acid, 2-amino-, 2-propenyl ester;ALLYLANTHRANILATE;FEMA No. 2020;2-Propen-1-yl 2-aminobenzoate;Allyl Anthraniliate;CCRIS 6207;EINECS 231-331-0;NSC 147476;AI3-36005;DTXSID3024441;UNII-81T0041N82;NSC-147476;81T0041N82;prop-2-en-1-yl 2-aminobenzoate;Allyl 2-aminobenzoate #;Allyl anthranilate, >=98%;MLS002415710;SCHEMBL759012;DTXCID804441;CHEMBL1606698;2-amino-benzoic acid allyl ester;ALLYL ANTHRANILATE [FHFI];CHEBI:178980;HMS3039M08;ALLYL ANTHRANILATE [USP-RS];Tox21_201129;NSC147476;Anthranilic acid, allyl ester (8CI);LS-1648;NCGC00091858-01;NCGC00091858-02;NCGC00258681-01;SMR001370893;Benzoic acic, 2-amino-, 2-propenyl ester;CAS-7493-63-2;Benzoic acid,2-amino-,2-propen-1-yl ester;FT-0739321;BENZOIC ACID, 2-AMINO-, 2-PROPEN-1-YL ESTER;Q27269266;Allyl anthranilate, United States Pharmacopeia (USP) Reference Standard

Chemical Property of Allyl anthranilate

Chemical Property:

• Appearance/Colour: Clear golden liquid
• Vapor Pressure: 0.0011mmHg at 25°C
• Melting Point: 224-228 °C
• Refractive Index: n20/D 1.574(lit.)
• Boiling Point: 300.7 °C at 760 mmHg
• Flash Point: 156.1 °C
• PSA: 52.32000
• Density: 1.123 g/cm³
• LogP: 2.19280
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

AllylAnthraniliate ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC(=O)C1=CC=CC=C1N
• Uses: Allyl Anthraniliate is used in the synthesis of diazabicyclo-heptanone compounds mimicking β-lactam antibiotics. Allyl Anthranilate is a synthetic flavoring agent that is a light yel- low colored liquid of green leaf-wine odor. it is stable but may cause discoloration. it should be stored in glass or tin containers. it is used as flavoring for its wine note and has application in beverages and candy at 1–2 ppm.

Technology Process of Allyl anthranilate

There total 5 articles about Allyl 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: 97.0%

2-propenyl o-nitrobenzoate (107616-19-3) → anthranilic acid allyl ester (7493-63-2)

Guidance literature:

With tin(ll) chloride; In methanol; for 1.5h; Ambient temperature;

Reference yield: 45.7%

isatoic anhydride (118-48-9) + allyl alcohol (107-18-6) → anthranilic acid allyl ester (7493-63-2)

Guidance literature:

With sodium; Heating;

DOI:10.1135/cccc19960751

Reference yield: 38.0%

anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) + allyl bromide (106-95-6) → allyl 2-(N-allylamino)benzoate (1023287-68-4) + anthranilic acid allyl ester (7493-63-2)

Guidance literature:

anthranilic acid; With potassium hydroxide; at 20 ℃;

allyl bromide; In N,N-dimethyl-formamide; at 20 ℃; Further stages.;

DOI:10.1002/jhet.5570450222

upstream raw materials:

2-propenyl o-nitrobenzoate

isatoic anhydride

allyl alcohol

ortho-nitrobenzoic acid

Downstream raw materials:

2-(3,4-Dimethoxy-benzoylamino)-benzoic acid allyl ester

(2S,4R)-2-(2-Allyloxycarbonyl-phenylcarbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid allyl ester

2-{[3-(2,6-Dichloro-phenyl)-5-methyl-isoxazole-4-carbonyl]-amino}-benzoic acid allyl ester

2-(2-Carboxyphenyl)-2,5-diazabicyclo[2.2.1]heptan-3-one

Refernces

• 1、 Brown, David P.,Duong, Hoan Q.. "Synthesis of novel aromatic macrolactones via ring closing metathesis of substituted phenylalkanoic acid allylic esters". . p. 435 - 443. Retrieved 2008/09/19.
• 2、 Hadfield, Peter S.,Galt, Ron H. B.,Sawyer, Yvonne,Layland, Nicola J.,Page, Michael I.. "An unexpected Mitsunobu reaction. A direct route to the 2,5-diazabicyclo[2.2.1]heptan-3-one skeleton as a γ-lactam mimic of β-lactam antibiotics". . p. 503 - 509. Retrieved 2007/10/03.