Bentranil

Base Information

• Chemical Name: Bentranil
• CAS No.: 1022-46-4
• Molecular Formula: C14H9 N O2
• Molecular Weight: 223.231
• Hs Code.: 29349990
• European Community (EC) Number: 620-965-7
• NSC Number: 16082
• UNII: F6R7D8UJO5
• DSSTox Substance ID: DTXSID60144732
• Nikkaji Number: J12.254H
• Wikidata: Q72444980
• ChEMBL ID: CHEMBL24449
• Mol file: 1022-46-4.mol

Synonyms:Bentranil;1022-46-4;2-Phenyl-4H-3,1-benzoxazin-4-one;Linarotox;Linurotox;2-Phenyl-3,1-benzoxazin-4-one;4H-3,1-BENZOXAZIN-4-ONE, 2-PHENYL-;H-170;2-Phenyl-3,1-benzoxazinone-(4);2-Phenyl-benzo[d][1,3]oxazin-4-one;NSC 16082;3-Phenyl-1H-2,4-benzoxazin-1-one;F6R7D8UJO5;CHEMBL24449;3-Phenyl-2,4-benzoxazin-1-one;NSC-16082;AI3-61952;SR-01000389722;NSC16082;2-phenylbenzo[d]1,3-oxazin-4-one;2-Phenyl-4-[4H]-3,1-benzoxazinone;4H-3, 2-phenyl-;Maybridge1_006945;ChemDiv2_003515;UNII-F6R7D8UJO5;Oprea1_579311;CBDivE_001429;SCHEMBL272702;WLN: T66 BVO ENJ DR;HMS561D15;DTXSID60144732;CHEBI:145402;HMS1378P17;2-phenyl-[3,1]benzoxazin-4-one;BAA02246;BDBM50077011;MFCD00043598;STK385092;AKOS000313370;JS-3012;2-PHENYL-4-OXO-3,1-BENZOXAZINE;2-Phenyl-4H-benzo[d][1,3]oxazin-4-one;B5739;CS-0086717;EU-0066816;FT-0622748;2-PHENYLBENZO(D)(1,3)OXAZIN-4-ONE;Bentranil, PESTANAL(R), analytical standard;T70020;EN300-22840157;J-000660;SR-01000389722-1;SR-01000389722-2;Z57177801

Chemical Property of Bentranil

Chemical Property:

• Vapor Pressure: 5.32E-05mmHg at 25°C
• Melting Point: 123-125 °C(lit.)
• Refractive Index: 1.4700 (estimate)
• Boiling Point: 189-192 °C8 mm Hg(lit.)
• PKA: 1.74±0.20(Predicted)
• Flash Point: 163°C
• PSA: 43.10000
• Density: 1.23g/cm³
• LogP: 2.85500
• Solubility.: soluble in Toluene
• Water Solubility.: 5.5mg/L(20 oC)
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 223.063328530
• Heavy Atom Count: 17
• Complexity: 331

Purity/Quality:

98%,99%, ^*data from raw suppliers

Bentranil ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C2=NC3=CC=CC=C3C(=O)O2
• Uses: Bentranil is used as part of a pesticide formulation. Also used in the preparation of a new class of DPP-4 and DPPH inhibitors as potential antidiabetic agents and antioxidants.

Technology Process of Bentranil

There total 118 articles about Bentranil 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%

carbon monoxide (201230-82-2) + 2-iodophenylamine (615-43-0) + benzoyl chloride (98-88-4) → 2-phenyl-4H-3,1-benzoxazin-4-one (1022-46-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; palladium diacetate; In tetrahydrofuran; at 100 ℃; for 24h; under 15514.9 Torr;

DOI:10.1021/ol990258y

Reference yield: 98.0%

2-azidobenzoic benzoic anhydride → 2-phenyl-4H-3,1-benzoxazin-4-one (1022-46-4)

Guidance literature:

With triphenylphosphine; In toluene; at 20 ℃; for 1h; Reagent/catalyst; Solvent; Temperature;

DOI:10.1021/acscatal.6b00165

Reference yield: 96.0%

benzoyl chloride (98-88-4) + anthranilic acid (118-92-3,159201-01-1,50816-84-7,80206-34-4,104809-47-4) → 2-phenyl-4H-3,1-benzoxazin-4-one (1022-46-4)

Guidance literature:

With sodium carbonate; In tetrahydrofuran; at 20 ℃; Cooling with ice;

DOI:10.1039/c9cc03905h

upstream raw materials:

2-Benzoylbenzoic acid

2-(Benzoylamino)benzoic Acid

isatoic anhydride

benzoyl chloride

Downstream raw materials:

2-benzoylaminobenzamide

4-methoxy-2-phenyl-quinoline

4-ethoxy-3-methyl-2-phenylquinoline

2-benzamido-N-cyclohexylbenzamide

Refernces

• 1、 Zhang, Chenhao,Li, Sanliang,Bure?, Filip,Lee, Richmond,Ye, Xinyi,Jiang, Zhiyong. "Visible Light Photocatalytic Aerobic Oxygenation of Indoles and pH as a Chemoselective Switch". . p. 6853 - 6860. Retrieved 2016.
• 2、 Mokale, Santosh N.,Palkar, Akash D.,Dube, Pritam N.,Sakle, Nikhil S.,Miniyar, Pankaj B.. "Design, synthesis and in vivo screening of some novel quinazoline analogs as anti-hyperlipidemic and hypoglycemic agents". . p. 272 - 276. Retrieved 2016.
• 3、 Nasli-Esfahani, Ensieh,Mohammadi-Khanaposhtani, Maryam,Rezaei, Sepideh,Sarrafi, Yaghoub,Sharafi, Zeinab,Samadi, Nasser,Faramarzi, Mohammad Ali,Bandarian, Fatemeh,Hamedifar, Haleh,Larijani, Bagher,Hajimiri, Mirhamed,Mahdavi, Mohammad. "A new series of Schiff base derivatives bearing 1,2,3-triazole: Design, synthesis, molecular docking, and α-glucosidase inhibition". . . Retrieved 2019.
• 4、 Patel, Mohan,Chhasatia, Mehul,Bhatt, Bhupesh. "In vitro bacteriostatic and DNA interaction studies of drug-based mixed-ligand complexes of cobalt(II)". . p. 220 - 230. Retrieved 2011.
• 5、 Bristow et al.. "-". . p. 677. Retrieved 1974.
• 6、 Rad-Moghadam, Kurosh,Rouhi, Somayeh. "Silica-bound benzoyl chloride mediated the solid-phase synthesis of 4H-3, 1-benzoxazin-4-ones". . . Retrieved 2009.
• 7、 Eckroth,Squire. "-". . p. 224. Retrieved 1971.
• 8、 Pisal, Pooja,Deodhar, Meenakshi,Kale, Amol,Nigade, Ganesh,Pawar, Smita. "Design, synthesis, docking studies and biological evaluation of 2-phenyl-3-(Substituted benzo[d] thiazol-2-ylamino)-quinazoline-4(3H)-one derivatives as antimicrobial agents". . p. 57 - 61. Retrieved 2018.
• 9、 Eissa, Ibrahim.H.,Ibrahim, Mohammed K.,Metwaly, Ahmed M.,Belal, Amany,Mehany, Ahmed B.M.,Abdelhady, Alsayed A.,Elhendawy, Mostafa A.,Radwan, Mohamed M.,ElSohly, Mahmoud A.,Mahdy, Hazem A.. "Design, molecular docking, in vitro, and in vivo studies of new quinazolin-4(3H)-ones as VEGFR-2 inhibitors with potential activity against hepatocellular carcinoma". . . Retrieved 2021.
• 10、 Dewangan, Dhansay,Nakhate, Kartik T.,Verma, Vinay Sagar,Nagori, Kushagra,Tripathi, Dulal Krishna. "Synthesis, Characterization, and Screening for Analgesic and Anti-Inflammatory Activities of Schiff Bases of 1,3,4-Oxadiazoles Linked With Quinazolin-4-One". . p. 3187 - 3194. Retrieved 2017.