(S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

Base Information

• Chemical Name: (S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol
• CAS No.: 187235-08-1
• Molecular Formula: C6H7 N3 O4
• Molecular Weight: 185.139
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID80435977
• Nikkaji Number: J2.456.845H
• Wikidata: Q72494633
• ChEMBL ID: CHEMBL489704
• Mol file: 187235-08-1.mol

Synonyms:187235-08-1;(S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol;(6S)-2-NITRO-6,7-DIHYDRO-5H-IMIDAZO[2,1-B][1,3]OXAZIN-6-OL;5H-Imidazo[2,1-b][1,3]oxazin-6-ol, 6,7-dihydro-2-nitro-, (6S)-;(S)-(-)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol;4-Nitro-(S)-alcohol;(6S)-2-nitro-5H,6H,7H-imidazo[2,1-b][1,3]oxazin-6-ol;SCHEMBL64590;CHEMBL489704;DTXSID80435977;MFCD08436173;AKOS016843175;AC-6401;AS-33271;CS-0053124;A880594;(S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxa-zin-6-ol;(6S)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine-6alpha-ol

Chemical Property of (S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.765
• Boiling Point: 446.2°Cat760mmHg
• PKA: 13.21±0.20(Predicted)
• Flash Point: 223.7°C
• PSA: 93.10000
• Density: 1.91g/cm³
• LogP: 0.06780
• Storage Temp.: 2-8°C
• Solubility.: Chloroform, DCM, Methanol
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 185.04365571
• Heavy Atom Count: 13
• Complexity: 218

Purity/Quality:

97% ^*data from raw suppliers

(S)-(-)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(COC2=NC(=CN21)[N+](=O)[O-])O
• Isomeric SMILES: C1[C@@H](COC2=NC(=CN21)[N+](=O)[O-])O
• Uses: (S)-(-)-2-Nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol is an intermediate in the synthesis of (S)-PA 824 (P122500), a novel anti-tuberculosis drug.

Technology Process of (S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol

There total 8 articles about (S)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-6-ol 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: 93.0%

C15H13N3O5 → (S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol (187235-08-1)

Guidance literature:

With titanium(IV) isopropylate; In methanol; for 12h; Heating;

DOI:10.1002/adsc.200700119

Reference yield: 90.0%

C10H13N3O5 → (S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol (187235-08-1)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; at 20 ℃; for 1h;

DOI:10.1002/adsc.200700119

Reference yield: 86.0%

(S)-2-nitro-6-(tetrahydro-pyran-2-yloxy)-6,7-dihydro-5H-imidazo[2,1-b]-[1,3]oxazine (187235-06-9) → (S)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazin‐6‐ol (187235-08-1)

Guidance literature:

With hydrogenchloride; In methanol; water; at 60 ℃; for 4h; Temperature;

upstream raw materials:

(S)-2-nitro-6-(tetrahydro-pyran-2-yloxy)-6,7-dihydro-5H-imidazo[2,1-b]-[1,3]oxazine

C₁₂H₂₂N₄O₆Si

Downstream raw materials:

(S)‐6‐((4‐bromobenzyl)oxy)‐2‐nitro‐6,7‐dihydro‐5H‐imidazo[2,1‐b][1,3]oxazine

(6S)-2-nitro-6-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

(6S)-6-[(4-bromo-2-fluorobenzyl)oxy]-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine

(S)-6-(4-chloromethyl-benzyloxy)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine