6-nitro-3,4-dihydro-2H-1,4-benzoxazine

Base Information

• Chemical Name: 6-nitro-3,4-dihydro-2H-1,4-benzoxazine
• CAS No.: 28226-22-4
• Molecular Formula: C8H8N2O3
• Molecular Weight: 180.16
• Hs Code.: 2934999090
• European Community (EC) Number: 808-653-0
• DSSTox Substance ID: DTXSID40427671
• Wikidata: Q82240325
• Mol file: 28226-22-4.mol

Synonyms:6-nitro-3,4-dihydro-2H-1,4-benzoxazine;28226-22-4;6-NITRO-3,4-DIHYDRO-2H-BENZO[B][1,4]OXAZINE;MFCD07698591;2H-1,4-Benzoxazine,3,4-dihydro-6-nitro-;SCHEMBL305008;DTXSID40427671;GZAJZBARYACGSO-UHFFFAOYSA-N;AKOS005070315;6-nitro-2,3-dihydrobenz-1,4-oxazine;AB42101;SY130733;6-nitro-3,4-dihydro-2H-[1,4]benzoxazine;6-nitro-3,4-dihydro-2H-benzo[1,4]oxazine;AM20040086;CS-0089896;FT-0680344;EN300-159912;3Z-5010;J-518955;Z1198173496

Chemical Property of 6-nitro-3,4-dihydro-2H-1,4-benzoxazine

Chemical Property:

• Vapor Pressure: 0.000107mmHg at 25°C
• Melting Point: 117-119 °C
• Refractive Index: 1.585
• Boiling Point: 337.1 °C at 760 mmHg
• PKA: 2.67±0.20(Predicted)
• Flash Point: 157.7 °C
• PSA: 67.08000
• Density: 1.332 g/cm³
• LogP: 2.06030
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 180.05349212
• Heavy Atom Count: 13
• Complexity: 204

Purity/Quality:

98%min ^*data from raw suppliers

6-Nitro-3,4-dihydro-2H-1,4-benzoxazine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COC2=C(N1)C=C(C=C2)[N+](=O)[O-]

Technology Process of 6-nitro-3,4-dihydro-2H-1,4-benzoxazine

There total 3 articles about 6-nitro-3,4-dihydro-2H-1,4-benzoxazine 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: 11.0%

1-amino-2-(4-nitrophenoxy)ethane hydrochloride (98395-62-1) → N-(2-hydroxyethyl)-4-nitroaniline (1965-54-4) + 6-nitro-1,4-benzoxazine (28226-22-4) + N-(2-hydroxyethyl)-2-hydroxy-5-nitroaniline

Guidance literature:

With sodium carbonate; In water; at 2 - 18 ℃; for 2h; Irradiation;

DOI:10.1021/ja00534a055

Reference yield: 11.0%

1-amino-2-(4-nitrophenoxy)ethane hydrochloride (98395-62-1) → N-(2-hydroxyethyl)-4-nitroaniline (1965-54-4) + N-(2-hydroxyethyl)-2-hydroxy-5-nitroaniline (74032-78-3) + 6-nitro-1,4-benzoxazine (28226-22-4)

Guidance literature:

With sodium carbonate; at 0 - 18 ℃; for 1.5h; Product distribution; Mechanism; Irradiation; other β-(nitrophenoxy)ethylamines;

DOI:10.1021/jo00223a016

Reference yield:

acetic anhydride (108-24-7) + 1,4-benzoxazine (5735-53-5) → 6-nitro-1,4-benzoxazine (28226-22-4) + 3,4-dihydro-7-nitro-2H-1,4-benzoxazine (120711-81-1)

Guidance literature:

acetic anhydride; 1,4-benzoxazine; With nitric acid; at 0 ℃; for 0.5h; Cooling with ice; Inert atmosphere;

With hydrogenchloride; In ethanol; at 60 ℃; for 4h;

upstream raw materials:

1-amino-2-(4-nitrophenoxy)ethane hydrochloride

acetic anhydride

1,4-benzoxazine

Downstream raw materials:

N-[4-[6-(2-cyclopentylacetamido)-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoyl]-2-methylbenzenesulphonamide

N-[4-[6-(cyclopentyloxycarbonyl)amino-2,3-dihydrobenz-1,4-oxazin-4-ylmethyl]-3-methoxybenzoyl]benzenesulphonamide

methyl 4-<<6-<<(cyclopentyloxy)carbonyl>amino>-2,3-dihydrobenz-1,4-oxazin-4-yl>methyl>-3-methoxybenzoate

4-<<6-<<(cyclopentyloxy)carbonyl>amino>-2,3-dihydrobenz-1,4-oxazin-4-yl>methyl>-3-methoxybenzoic acid

Refernces

• 1、 Wubbels, Gene G.,Halverson, Ann M.,Oxman, Joe D.,Bruyn, Van H. De. "Regioselectivity of Photochemical and Thermal Smiles Rearrangements and Related Reactions of β-(Nitrophenoxy)ethylamines". . p. 4499 - 4504. Retrieved 2007/10/02.