Isosorbide 2-nitrate

Base Information

• Chemical Name: Isosorbide 2-nitrate
• CAS No.: 16106-20-0
• Molecular Formula: C₆H₉NO₆
• Molecular Weight: 191.141
• Hs Code.: 2932999000
• European Community (EC) Number: 240-271-4
• UNII: 21BMF8FI0K
• DSSTox Substance ID: DTXSID40873331
• Wikidata: Q27253548
• ChEMBL ID: CHEMBL1310
• Mol file: 16106-20-0.mol

Synonyms:isosorbide 2-nitrate;isosorbide-2-mononitrate

Chemical Property of Isosorbide 2-nitrate

Chemical Property:

• Vapor Pressure: 8.66E-07mmHg at 25°C
• Melting Point: >51.5°C
• Refractive Index: 1.4860 (estimate)
• Boiling Point: 364.5°Cat760mmHg
• PKA: 13.09±0.40(Predicted)
• Flash Point: 174.2°C
• PSA: 93.74000
• Density: 1.56g/cm³
• LogP: -0.75500
• Storage Temp.: -20°C Freezer
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 191.04298701
• Heavy Atom Count: 13
• Complexity: 216

Purity/Quality:

90.0%Min ^*data from raw suppliers

1,4:3,6-Dianhydro-2-nitro-D-glucitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C2C(O1)C(CO2)O[N+](=O)[O-])O
• Isomeric SMILES: C1[C@H]([C@@H]2[C@H](O1)[C@H](CO2)O[N+](=O)[O-])O
• Uses: Isosorbide 2-mononitrate is a metabolite of Isosorbide Dinitrate. Used as an antianginal.

Technology Process of Isosorbide 2-nitrate

There total 27 articles about Isosorbide 2-nitrate 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%

Isosorbide (652-67-5) → isosorbide mononitrate (16106-20-0,16908-90-0,16908-91-1,35993-37-4,38709-03-4,114718-64-8,127001-76-7,16051-77-7)

Guidance literature:

Isosorbide; With chloro-trimethyl-silane; triethylamine; at -5 ℃; for 0.5h;

With aluminum (III) chloride; sodium nitrate; at -5 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield: 91.0%

isosorbide 2-acetate-5-mononitrate (39813-48-4) → isosorbide mononitrate (16106-20-0,16908-90-0,16908-91-1,35993-37-4,38709-03-4,114718-64-8,127001-76-7,16051-77-7)

Guidance literature:

With potassium carbonate; In methanol; water;

Reference yield: 85.0%

(3S,3aR,6R,6aS)-6-(nitrooxy)hexahydrofuro[3,2-b]furan-3-yl benzoate (75648-24-7) → isosorbide mononitrate (16106-20-0,16908-90-0,16908-91-1,35993-37-4,38709-03-4,114718-64-8,127001-76-7,16051-77-7)

Guidance literature:

With potassium hydroxide; In ethanol; at 50 ℃; for 0.333333h;

DOI:10.1002/cmdc.201500275

upstream raw materials:

D-sorbitol

isosorbide 2-acetate-5-mononitrate

isosorbide dinitrate

isosorbide 2-O-butanoate

Downstream raw materials:

(1S,2S,5S,6R)-6-(nitrooxy)-4,8-dioxabicyclo(3.3.0)oct-2-yl 2-(1-((4-chlorophenyl)carbonyl)-5-methoxy-2-methylindol-3-yl)acetate

C₁₃H₁₂N₂O₁₀

C₂₇H₃₇N₃O₈S

C₂₈H₃₇N₃O₁₁S

Refernces

• 1、 -. "Synthesis method and application of isosorbide mononitrate". Paragraph 0032-0040. . Retrieved 2021/07/14.
• 2、 Zhu, Shi-Guo,Yang, Jiang-Tao,Zhang, Gui-Min,Chen, Cheng-Fu,Zhang, Fu-Li. "An Improved Process for Industrial Production of Isosorbide-5-mononitrate: Recycling of Wastes". supporting information. p. 991 - 995. Retrieved 2018/08/03.