3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

Base Information

• Chemical Name: 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile
• CAS No.: 134997-74-3
• Molecular Formula: C9H6N2O2
• Molecular Weight: 174.15600
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70443001
• Wikidata: Q82260661
• Mol file: 134997-74-3.mol

Synonyms:134997-74-3;3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile;3-Oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile;3-oxo-4H-1,4-benzoxazine-6-carbonitrile;3-Oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile;SCHEMBL705560;DTXSID70443001;WCBILQWUWLALFZ-UHFFFAOYSA-N;MFCD20039908;DS-6140;SB32953;6-Cyano-2H-1,4-Benzoxazin-3(4H)-one;CS-0062066;A925544;A1-04060;3-oxo-3,4-dihydro-2H-1,4-benzoxazin-6-carbonitrile

Chemical Property of 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

Chemical Property:

• Melting Point: 106-108 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• Boiling Point: 403.2±45.0 °C(Predicted)
• PKA: 11.77±0.20(Predicted)
• PSA: 65.61000
• Density: 1.39±0.1 g/cm3(Predicted)
• LogP: 0.97428
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 174.042927438
• Heavy Atom Count: 13
• Complexity: 268

Purity/Quality:

97% ^*data from raw suppliers

3,4-Dihydro-3-oxo-2H-1,4-benzoxazine-6-carbonitrile 95.0% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)NC2=C(O1)C=CC(=C2)C#N

Technology Process of 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile

There total 12 articles about 3-Oxo-3,4-dihydro-2H-benzo[b][1,4]oxazine-6-carbonitrile 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: 95.0%

2-Bromo-N-(5-cyano-2-hydroxy-phenyl)-acetamide (1026273-07-3) → 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile (134997-74-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 80 ℃; for 0.25h; microwave irradiation;

DOI:10.1016/j.ejmech.2004.05.003

Reference yield: 89.0%

6-bromo-3,4-dihydro-2H-1,4-benzoxazin-3-one (24036-52-0) + dicyanozinc (557-21-1) → 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile (134997-74-3)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 80 ℃;

Reference yield: 69.0%

3-amino-4-hydroxybenzonitrile (14543-43-2) + 2-Bromoacetyl bromide (598-21-0) → 3-oxo-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonitrile (134997-74-3)

Guidance literature:

With sodium hydrogencarbonate; In chloroform; water; at 0 - 20 ℃;

upstream raw materials:

2-Bromo-N-(5-cyano-2-hydroxy-phenyl)-acetamide

3-amino-4-hydroxybenzonitrile

4-hydroxy-3-nitrobenzonitrile

chloroacetyl chloride

Downstream raw materials:

6-(aminomethyl)-2H-benzo[1,4]oxazin-3(4H)-one hydrochloride

methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate