Anthranil

Base Information

• Chemical Name: Anthranil
• CAS No.: 271-58-9
• Molecular Formula: C7H5 N O
• Molecular Weight: 119.123
• Hs Code.: 29349990
• European Community (EC) Number: 205-980-5
• NSC Number: 99331
• UNII: 58GQ20G9W6
• DSSTox Substance ID: DTXSID00181565
• Nikkaji Number: J5.446A
• Wikipedia: Anthranil
• Wikidata: Q27122650
• Metabolomics Workbench ID: 57785
• ChEMBL ID: CHEMBL508432
• Mol file: 271-58-9.mol

Synonyms:anthranil

Chemical Property of Anthranil

Chemical Property:

• Appearance/Colour: CLEAR YELLOW TO BROWN-RED LIQUID
• Vapor Pressure: 0.221mmHg at 25°C
• Melting Point: <-18.15°C
• Refractive Index: n20/D 1.584(lit.)
• Boiling Point: 215°Cat760mmHg
• PKA: -2.03±0.30(Predicted)
• Flash Point: 93.9°C
• PSA: 26.03000
• Density: 1.196g/cm³
• LogP: 1.82780
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 119.037113783
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

99% ^*data from raw suppliers

2,1-Benzisoxazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 24/25-25-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC2=CON=C2C=C1

Technology Process of Anthranil

There total 70 articles about Anthranil 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%

2-nitro-benzaldehyde (552-89-6) → anthranil (271-58-9)

Guidance literature:

With hydrogen; In toluene; at 30 ℃; for 1h; under 6750.68 Torr; chemoselective reaction; Autoclave;

DOI:10.1021/acscatal.7b01841

Reference yield: 98.0%

2-nitro-benzaldehyde (552-89-6) → anthranil (271-58-9) + o-aminobenzaldehyde (529-23-7)

Guidance literature:

With 2-bromo-2-nitropropane; zinc; In methanol; at 50 ℃; for 5h; Yields of byproduct given;

DOI:10.3987/com-96-7682

Reference yield: 65.0%

2-nitro-benzaldehyde (552-89-6) → anthranil (271-58-9) + 2-azidobenzaldehyde (16714-25-3)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; for 20h; > 60 deg C;

DOI:10.1016/S0040-4039(97)01272-0

upstream raw materials:

2-azidobenzaldehyde

diethyl ether

2-Nitrobenzyl alcohol

1-methyl-2-nitrobenzene

Downstream raw materials:

(+/-)-2-phenyl-(3at.9at)-9,9a-dihydro-3aH-4r,9c-epoxido-pyrrolo[3,4-b]quinoline-1,3-dione

N-(2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)benzenesulfonamide

isatoic anhydride

2-methyl-4-oxo-3,1-benzoxazine

Refernces

• 1、 Bucher, Goetz. "A laser flash photolysis study on 2-azido-N,N-diethylbenzylamine - The reactivity of iminoquinone methides in solution". . p. 2463 - 2475. Retrieved 2001.
• 2、 Zhang, Jingyi,Li, Ying,Zhang, Chaofeng,Wang, Xiao-Na,Chang, Junbiao. "Metal-Free [3+2] Annulation of Ynamides with Anthranils to Construct 2-Aminoindoles". supporting information. p. 2029 - 2035. Retrieved 2021/04/05.
• 3、 Zhuang, Shi-Yi,Tang, Yong-Xing,Chen, Xiang-Long,Wu, Yan-Dong,Wu, An-Xin. "I2-DMSO mediated oxidative amidation of methyl ketones with anthranils for the synthesis of: α -ketoamides". supporting information. p. 4258 - 4262. Retrieved 2021/05/31.