2-Methylcyclopentanone

Base Information

• Chemical Name: 2-Methylcyclopentanone
• CAS No.: 1120-72-5
• Deprecated CAS: 32854-37-8
• Molecular Formula: C6H10O
• Molecular Weight: 98.1448
• Hs Code.: 29142990
• European Community (EC) Number: 214-318-4
• NSC Number: 105429
• UNII: HTH47R9TXS
• DSSTox Substance ID: DTXSID50862554
• Nikkaji Number: J100.694K
• Wikidata: Q72489745
• Mol file: 1120-72-5.mol

Synonyms:2-METHYLCYCLOPENTANONE;1120-72-5;2-Methylcyclopentan-1-one;Cyclopentanone, 2-methyl-;.alpha.-Methylcyclopentanone;alpha-Methylcyclopentanone;HTH47R9TXS;Cyclopentan-1-one, 2-methyl-;EINECS 214-318-4;MFCD00001414;NSC 105429;NSC-105429;AI3-39196;28631-88-1;Cyclopentanone, methyl-;2-METHYLCYCLOPENTANONE (2,5,5-D3);methylcyclopentanone;methyl cyclopentanone;2-methyl cyclopentanone;UNII-HTH47R9TXS;3-methyl-2-cyclopentanone;2-methyl-cyclopentan-1-one;2-Methylcyclopentanone, 98%;(rac)-2-methyl-cyclopentanone;DTXSID50862554;BBL102758;NSC105429;STL556564;AKOS005259854;AM84338;SY045483;2-METHYLCYCLOPENTANONE (D3-METHYL);FT-0600375;CYCLOPENTANONE, 2-METHYL-, (+/-)-;EN300-69526;A904603;J-002702;F9995-1299;Z813018382

Chemical Property of 2-Methylcyclopentanone

Chemical Property:

• Appearance/Colour: clear colourless to very slightly yellow liquid
• Vapor Pressure: 5.8mmHg at 25°C
• Melting Point: -75°C
• Refractive Index: n20/D 1.435(lit.)
• Boiling Point: 141.647 °C at 760 mmHg
• Flash Point: 32.701 °C
• PSA: 17.07000
• Density: 0.933 g/cm³
• LogP: 1.37550
• Storage Temp.: Flammables area
• Water Solubility.: soluble
• XLogP3: 1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 98.073164938
• Heavy Atom Count: 7
• Complexity: 86.2

Purity/Quality:

99.9% ^*data from raw suppliers

2-Methylcyclopentanone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 10
• Safety Statements: 16-29-33

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CCCC1=O

Technology Process of 2-Methylcyclopentanone

There total 192 articles about 2-Methylcyclopentanone 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: 98.0%

1-(trimethylsilyloxy)cyclopentene (19980-43-9) + methyl iodide (74-88-4) → 2-Methylcyclopentanone (1120-72-5) + 2,2-dimethylcyclopentanone (4541-32-6) + cis-2,5-dimethylcyclopentanone (6672-39-5) + (+/-)-trans-2,5-dimethylcyclopentanone (83664-37-3)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; methyllithium; dimethyl zinc(II); In tetrahydrofuran; at -78 ℃; for 10h;

DOI:10.1021/jo00269a006

Reference yield: 81.0%

lithium cyclopent-1-enolate (37160-52-4) + methyl iodide (74-88-4) → 2-Methylcyclopentanone (1120-72-5) + 2,2-dimethylcyclopentanone (4541-32-6) + 2,5-dimethylcyclopentanone (4041-09-2)

Guidance literature:

In tetrahydrofuran; at -50 ℃; for 10h;

Reference yield: 79.0%

1-(trimethylsilyloxy)cyclopentene (19980-43-9) + methyl iodide (74-88-4) → 2-Methylcyclopentanone (1120-72-5) + 2,2-dimethylcyclopentanone (4541-32-6) + 2,2,5-trimethylcyclopentanone (4573-09-5) + cis-2,5-dimethylcyclopentanone (6672-39-5)

Guidance literature:

With methyllithium; In tetrahydrofuran; at 0 ℃; for 3h; Further byproducts given;

DOI:10.1021/jo00269a006

upstream raw materials:

2-chlorocyclopentanone

methyl magnesium iodide

diethyl ether

(+/-)-2t-chloro-1-methyl-cyclopentan-r-ol

Downstream raw materials:

1-cyclohexyl-2-methyl-cyclopentene

2-methyl-1-phenethyl-cyclopentanol

δ-caprolactam

2,2-dimethylcyclopentanone

Refernces

• 1、 Fu, Yilei,Hoelsch, Kathrin,Weuster-Botz, Dirk. "A novel ene-reductase from Synechococcus sp. PCC 7942 for the asymmetric reduction of alkenes". . p. 1988 - 1997. Retrieved 2012.
• 2、 Bertrand et al.. "". . p. 790. Retrieved 1964.
• 3、 Larson, Gerald L.,Cadiz, Carlos. "ATTEMPTED GENERATION OF HALOCARBENES: PROTODESILYLATION OF DIHALOMETHYLSILANES". . p. 113 - 116. Retrieved 1982.
• 4、 Tsuji, Jiro,Nisar, Mohammad,Shimizu, Isao,Minami, Ichiro. "Novel Synthetic Method for 2-Methyl-2-cyclopentenone from Diallyl Adipate by Two-Pot Reactions". . p. 1009. Retrieved 1984.
• 5、 Conia,J.M.,Girard,C.. "-". . p. 2767 - 2770. Retrieved 1973.
• 6、 Bartlett,White. "-". . p. 2785. Retrieved 1934.
• 7、 Hammond,Collins. "-". . p. 4323,4324. Retrieved 1960.
• 8、 Molnar, Arpad,Bucsi, Imre,Bartok, Mihaly. "Studies on the chemistry of diols and cyclic ethers-53. Dehydration of 1,1-bishydroxymethylcycloalkanes: A quest for a 1,3-hydride shift". . p. 4929 - 4936. Retrieved 1992.
• 9、 Suzuki, Masaaki,Koyama, Hiroko,Noyori, Ryoji. "Effects of HMPA on the Structure and Reactivity of the Lithium Enolate of Cyclopentanone in THF: The Dimer is Responsible for Alkylation and Proton Exchange Reactions". . p. 259 - 268. Retrieved 2004.
• 10、 Pereyre et al.. "". . p. 97. Retrieved 1968.