1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone

Base Information

• Chemical Name: 1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone
• CAS No.: 69195-97-7
• Molecular Formula: C12H10N4O5
• Molecular Weight: 290.235
• Hs Code.: 2933290090
• DSSTox Substance ID: DTXSID20475852
• Nikkaji Number: J1.690.737E
• Wikidata: Q82306657
• Mol file: 69195-97-7.mol

Synonyms:69195-97-7;1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone;2-Nitro-1-[5-nitro-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone;1-(1-benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethan-1-one;1-(1-BENZYL-5-NITROIMIDAZOL-4-YL)-2-NITROETHANONE;1-(1-benzyl-5-nitro-imidazol-4-yl)-2-nitro-ethanone;SCHEMBL11463358;DTXSID20475852;NCGPOUCWHOHOER-UHFFFAOYSA-N;2-Nitro-1-[5-nitro-1-(phenylmethyl)-1H-imidazol-4-yl] ethanone;AKOS015961643;PB12439;AC-14388;CS-0057422;FT-0650974;P10444;2-nitro-1-(1-benzyl-5-nitro-1h-imidazole-4-yl)ethanone

Chemical Property of 1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone

Chemical Property:

• Vapor Pressure: 6.95E-13mmHg at 25°C
• Refractive Index: 1.671
• Boiling Point: 567.2°C at 760 mmHg
• Flash Point: 296.9°C
• PSA: 126.53000
• Density: 1.5g/cm³
• LogP: 2.34540
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 290.06511943
• Heavy Atom Count: 21
• Complexity: 413

Purity/Quality:

98%min ^*data from raw suppliers

2-Nitro-1-[5-nitro-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CN2C=NC(=C2[N+](=O)[O-])C(=O)C[N+](=O)[O-]

Technology Process of 1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone

There total 8 articles about 1-(1-Benzyl-5-nitro-1H-imidazol-4-yl)-2-nitroethanone 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: 68.0%

nitromethane (75-52-5) + 5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxylic acid (69195-96-6) → 2-nitro-1-(1-benzyl-5-nitro-1H-imidazol-4-yl)ethanone (69195-97-7)

Guidance literature:

5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 1h; Heating;

nitromethane; With potassium tert-butylate; at 0 - 5 ℃;

DOI:10.1016/S0040-4039(02)00053-9

Reference yield:

imidazolide (857027-07-7) + 1,1'-carbonyldiimidazole (530-62-1) + 5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxylic acid (69195-96-6) → 2-nitro-1-(1-benzyl-5-nitro-1H-imidazol-4-yl)ethanone (69195-97-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; nitromethane; dichloromethane; water;

Reference yield:

5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxaldehyde (87471-10-1) → 2-nitro-1-(1-benzyl-5-nitro-1H-imidazol-4-yl)ethanone (69195-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaClO₂; NH₂SO₃H / methanol; H₂O / 1.5 h / 20 °C

2.1: CDI / tetrahydrofuran / 1 h / Heating

2.2: 68 percent / t-BuOK / 0 - 5 °C

With sodium chlorite; aminosulfonic acid; 1,1'-carbonyldiimidazole; In tetrahydrofuran; methanol; water;

DOI:10.1016/S0040-4039(02)00053-9

upstream raw materials:

nitromethane

5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxylic acid

5-nitro-1-(phenylmethyl)-1H-imidazole-4-carboxaldehyde

benzyl chloride

Downstream raw materials:

6,7-dihydroimidazo<4,5-d><1,3>diazepin-8(3H)-one hydrochloride

2-amino-1-[5-amino-1-(phenylmethyl)-1H-imidazol-4-yl]ethanone dihydrochloride

(8S)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol

(8R)-3-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-3,6,7,8-tetrahydroimidazo<4,5-d><1,3>diazepin-8-ol

Refernces

• 1、 Chan,Putt,Showalter,Baker. "Total synthesis of (8R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-3,6,7,8- tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol (pentostatin), the potent inhibitor of adenosine deaminase". . p. 3457 - 3464. Retrieved 2007/10/02.