Cyclopentanone dimethylhydrazone

Base Information

• Chemical Name: Cyclopentanone dimethylhydrazone
• CAS No.: 14090-60-9
• Molecular Formula: C7H14 N2
• Molecular Weight: 126.202
• Hs Code.: 2928000090
• NSC Number: 126436
• UNII: UDS5W7B7J8
• DSSTox Substance ID: DTXSID60298845
• Nikkaji Number: J47.470C
• Mol file: 14090-60-9.mol

Synonyms:Cyclopentanone dimethylhydrazone;14090-60-9;Cyclopentanone, dimethylhydrazone;Cyclopentanone dimethyl hydrazone;N-(cyclopentylideneamino)-N-methylmethanamine;NSC-126436;2-cyclopentylidene-1,1-dimethylhydrazine;UDS5W7B7J8;SCHEMBL2731537;DTXSID60298845;Cyclopentanon-N,N-dimethylhydrazon;WEZHJSIEBKGPAO-UHFFFAOYSA-N;Cyclopentanone N,N-dimethylhydrazone;NSC126436;Cyclopentanone, 2,2-dimethylhydrazone;N'-cyclopentylidene-N,N-dimethylhydrazine

Chemical Property of Cyclopentanone dimethylhydrazone

Chemical Property:

• Vapor Pressure: 0.909mmHg at 25°C
• Boiling Point: 180.1°C at 760 mmHg
• Flash Point: 62.7°C
• PSA: 15.60000
• Density: 0.96g/cm³
• LogP: 1.47800
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 126.115698455
• Heavy Atom Count: 9
• Complexity: 108

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN(C)N=C1CCCC1

Technology Process of Cyclopentanone dimethylhydrazone

There total 5 articles about Cyclopentanone dimethylhydrazone 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: 91.0%

N,N-Dimethylhydrazine (57-14-7) + cyclopentanone (120-92-3) → 2-cyclopentylidene-1,1-dimethylhydrazine (14090-60-9)

Guidance literature:

In trifluoroacetic acid; benzene; for 5h; Heating;

DOI:10.1021/jo9623043

Reference yield: 89.0%

N,N-dimethylhydrazine hydrochloride (593-82-8,55484-54-3) + cyclopentanone (120-92-3) → 2-cyclopentylidene-1,1-dimethylhydrazine (14090-60-9)

Guidance literature:

With triethylamine; In ethanol; for 3.5h; Inert atmosphere; Reflux;

DOI:10.1021/jo402217e

Reference yield: 6.6%

1,1-dimethyldiazenium bromide (35758-82-8) + cyclopentanone ethylhydrazone → Tetramethyltetrazon (6130-87-6) + 2-cyclopentylidene-1,1-dimethylhydrazine (14090-60-9) + 5,5-dimethyl-3,3-tetramethylene-1-ethyl-3,4-dihydroformazan

Guidance literature:

With triethylamine; at -30 - -20 ℃; Title compound not separated from byproducts;

upstream raw materials:

N,N-Dimethylhydrazine

cyclopentanone

Trimethylhydrazin

1,1-dimethyldiazenium bromide

Downstream raw materials:

2-(N,N-dimethylhydrazono)cyclopentanecarbonitrile

2-butylcyclopentanone

2-hexylcyclopentanone

2-(4'-phenylbutyl)cyclopentanone

Refernces

• 1、 McAdoo,Hudson. "Interconversions of C5H10O+. ions with the oxygen on the first, second and third carbons: Approximately 60 communicating isomers". . p. 492 - 496. Retrieved 1995.
• 2、 Pichette, Simon,Winter, Dana K.,Lessard, Jean,Spino, Claude. "Converting cycloalkanones into N-heterocycles: Formal synthesis of (-)-gephyrotoxin 287C". . p. 12532 - 12544. Retrieved 2013.
• 3、 Maity, Sandeepan,Flowers, Robert A.. "Mechanistic Study and Development of Catalytic Reactions of Sm(II)". supporting information. p. 3207 - 3216. Retrieved 2019/02/19.
• 4、 Susinskis, Igors,Mekss, Peteris,Hmelnickis, Juris. "Method development for the determination of 1,1-dimethylhydrazine by the high-performance liquid chromatography–mass spectrometry technique". . p. 352 - 359. Retrieved 2018/07/31.