6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

Base Information

• Chemical Name: 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one
• CAS No.: 615568-17-7
• Molecular Formula: C9H9NO3
• Molecular Weight: 179.175
• DSSTox Substance ID: DTXSID20593989
• Nikkaji Number: J1.362.873D
• Wikidata: Q82488664
• Mol file: 615568-17-7.mol

Synonyms:615568-17-7;6-(hydroxymethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one;6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one;6-(hydroxymethyl)-4H-1,4-benzoxazin-3-one;MFCD09863091;SCHEMBL554735;DTXSID20593989;STL433116;AKOS009333711;AS-43128;SY238055;6-Hydroxymethyl-4H-benzo[1,4]oxazin-3-on;6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one;CS-0134982;6-1Hydroxymethyl-4H-benzo[1,4]oxazin-3-one;6-(Hydroxymethyl)-2,4-dihydro-1,4-benzoxazin-3-one

Chemical Property of 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

Chemical Property:

• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 179.058243149
• Heavy Atom Count: 13
• Complexity: 207

Purity/Quality:

NLT 98% ^*data from raw suppliers

6-(Hydroxymethyl)-2H-benzo[b][1,4]oxazin-3(4H)-one 95+% ^*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)CO

Technology Process of 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one

There total 4 articles about 6-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-one 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: 96.0%

(4-formyl-2-nitrophenyloxy)acetic acid ethyl ester (420786-61-4) → 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one (615568-17-7)

Guidance literature:

With hydrogen; nickel; In methanol; for 23h; under 2482.31 Torr;

DOI:10.1016/j.bmcl.2006.10.080

Reference yield: 69.0%

methyl 3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carboxylate (604756-32-3,202195-67-3) → 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one (615568-17-7)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 14h;

Reference yield:

4-hydroxy-3-nitrobenzaldehyde (3011-34-5) → 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one (615568-17-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaH / tetrahydrofuran; dimethylformamide / 24 h / Heating

2: 96 percent / H₂ / Raney nickel / methanol / 23 h / 2482.31 Torr

With hydrogen; sodium hydride; nickel; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2006.10.080

upstream raw materials:

(4-formyl-2-nitrophenyloxy)acetic acid ethyl ester

4-hydroxy-3-nitrobenzaldehyde

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

Downstream raw materials:

6-chloromethyl-4-(3-methoxy-propyl)-4H-benzo[1,4]oxazin-3-one

[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethyl]triphenyl-phosphonium chloride

methyl 4-[(3R,4S,5S)-3-{2-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]-ethyl}-1-(toluene-4-sulphonyl)-5-triisopropylsilanyloxypiperidin-4-yl]benzoate

methyl 4-[(3R,4S,5S)-3-{2-[4-(3-methoxypropyl)-3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl]vinyl}-1-(toluene-4-sulphonyl)-5-triisopropylsilanyloxypiperidin-4-yl]benzoate