3-(Nitromethyl)cyclopentanone

Base Information

• Chemical Name: 3-(Nitromethyl)cyclopentanone
• CAS No.: 81266-47-9
• Molecular Formula: C₆H₉NO₃
• Molecular Weight: 143.142
• Hs Code.: 2914700090
• DSSTox Substance ID: DTXSID50474712
• Nikkaji Number: J2.222.995H
• Mol file: 81266-47-9.mol

Synonyms:3-(NITROMETHYL)CYCLOPENTANONE;81266-47-9;3-(nitromethyl)cyclopentan-1-one;MFCD11847689;SCHEMBL9833852;DTXSID50474712;OXUCMXDWKATUHP-UHFFFAOYSA-N;AKOS016008233;DS-2581;SY021538;A9988;FT-0767573

Chemical Property of 3-(Nitromethyl)cyclopentanone

Chemical Property:

• Boiling Point: 279.82 °C at 760 mmHg
• Flash Point: 140.959 °C
• PSA: 62.89000
• Density: 1.202 g/cm³
• LogP: 1.15550
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 161

Purity/Quality:

99% ^*data from raw suppliers

3-(Nitromethyl)cyclopentanone >95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)CC1C[N+](=O)[O-]

Technology Process of 3-(Nitromethyl)cyclopentanone

There total 3 articles about 3-(Nitromethyl)cyclopentanone 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: 86.0%

cyclopent-2-enone (930-30-3) + nitromethane (75-52-5) → (+/-)-3-(nitromethyl)cyclopentanone (81266-47-9)

Guidance literature:

With L-arginine; In water; at 25 ℃; for 24h; Reagent/catalyst; Green chemistry;

DOI:10.5012/bkcs.2014.35.12.3671

Reference yield: 65.0%

nitromethane (75-52-5) + (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate (60410-16-4) → (+/-)-3-(nitromethyl)cyclopentanone (81266-47-9)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; regioselective reaction; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2010.01.025

Reference yield:

cyclopent-2-enone (930-30-3) + DBN (3001-72-7) → (+/-)-3-(nitromethyl)cyclopentanone (81266-47-9)

Guidance literature:

With sulfuric acid; In nitromethane; ethyl acetate; isopropyl alcohol;

upstream raw materials:

cyclopent-2-enone

nitromethane

DBN

(1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate

Downstream raw materials:

tert-butyl (3-hydroxycyclopentyl)methylcarbamate

3-(aminomethyl)cyclopentanol

N-{6,7-diethoxy-9-[3-(2-methyl-thiazol-4-yl)-phenylamino]-2,3-dihydro-1H-cyclopenta[b]quinolin-1-ylmethyl}-acetamide

N-{6,7-diethoxy-9-[3-(2-methyl-thiazol-4-yl)-phenylamino]-2,3-dihydro-1H-cyclopenta[b]quinolin-2-ylmethyl}-acetamide

Refernces

• 1、 Khan, Pasha M.,Bisht, Kirpal S.. "Unusual regioselectivity in Pd(0)-catalyzed coupling of allylic monoacetates and nitroalkanes: one-pot isomerization-alkylation". supporting information; experimental part. p. 1407 - 1410. Retrieved 2010/04/25.
• 2、 -. "Cycloalkyl-one-containing benzenesulphonamides". . . Retrieved 2008/06/13.