3-Methylene-1,5,5-trimethylcyclohexene

Base Information

• Chemical Name: 3-Methylene-1,5,5-trimethylcyclohexene
• CAS No.: 16609-28-2
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• Hs Code.: 2902199090
• DSSTox Substance ID: DTXSID60168074
• Nikkaji Number: J1.039.860F
• Wikidata: Q27162240
• Mol file: 16609-28-2.mol

Synonyms:3-Methylene-1,5,5-trimethylcyclohexene;16609-28-2;1,5,5-trimethyl-3-methylidenecyclohexene;3-METHYLENE 1,5,5-TRIMETHYL CYCLOHEXENE-1;Cyclohexene, 1,5,5-trimethyl-3-methylene-;1,5,5-trimethyl-3-methylenecyclohex-1-ene;CHEBI:90015;DTXSID60168074;ZKXYHQFGFMZPPJ-UHFFFAOYSA-N;methylidene 1,5,5trimethylcyclohexene;AKOS006273220;3-methylene-1,5,5-trimethyl cyclohexene;FT-0637383;1,5,5-Trimethyl-3-methylene-1-cyclohexene #;3-METHYLENE1,5,5-TRIMETHYLCYCLOHEXENE-1;Q27162240

Chemical Property of 3-Methylene-1,5,5-trimethylcyclohexene

Chemical Property:

• Vapor Pressure: 2.76mmHg at 25°C
• Boiling Point: 163°Cat760mmHg
• Flash Point: 39.2°C
• PSA: 0.00000
• Density: 0.83g/cm³
• LogP: 3.30890
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 136.125200510
• Heavy Atom Count: 10
• Complexity: 182

Purity/Quality:

99%min ^*data from raw suppliers

3-Methylene-1,5,5-trimethylcyclohexene 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=C)CC(C1)(C)C

Technology Process of 3-Methylene-1,5,5-trimethylcyclohexene

There total 8 articles about 3-Methylene-1,5,5-trimethylcyclohexene 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:

Diazo-acetic acid 3,5,5-trimethyl-cyclohex-2-enyl ester → 3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + 1,5,5-trimethyl-3-methylenecyclohex-1-ene (16609-28-2) + (2aR,2bS,5aR,5bS)-2b,4,4-Trimethyl-hexahydro-1-oxa-cyclopropa[cd]inden-2-one + (2aS,2bR,5aS,5bR)-2b,4,4-Trimethyl-hexahydro-1-oxa-cyclopropa[cd]inden-2-one

Guidance literature:

With tetrakisdirhodium(II); In dichloromethane; Product distribution; Heating; var. rhodium(II) complexes, other allylic diazoacetates;

DOI:10.1021/ja00149a031

Reference yield:

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + methyllithium (917-54-4) → 1,3,5,5-tetramethyl-1,3-cyclohexadiene (4724-89-4) + 1,5,5-trimethyl-3-methylenecyclohex-1-ene (16609-28-2)

Guidance literature:

In diethyl ether; at 0 - 20 ℃; for 2h; Overall yield = 65 %; Overall yield = 22 g; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.jorganchem.2014.08.003

Reference yield:

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + methylmagnesium bromide (75-16-1) → 1,5,5-trimethyl-3-methylenecyclohex-1-ene (16609-28-2)

Guidance literature:

With diethyl ether; Destillation des nach Hydrolyse erhaltenen Reaktionsprodukts mit KHSO₄ unter vermindertem Druck;

DOI:10.1039/jr9600003123 DOI:10.1021/jo01364a011 DOI:10.1021/ja01854a005

upstream raw materials:

methyl magnesium iodide

3,5,5-Trimethylcyclohex-2-en-1-one

methylmagnesium bromide

diazomethane

Downstream raw materials:

4,6-dibromo-1,2,3,5-tetramethylbenzene

Refernces

• 1、 Trifonova, Evgeniya A.,Perekalin, Dmitry S.,Loskutova, Natalia L.,Nelyubina, Yulia V.,Kudinov, Alexander R.. "Synthesis of the cyclohexadienyl ruthenium arene complexes [(η5-C6H3Me4)Ru(η6-arene)]+from the dimethyloctadienyl ruthenium chloride[(μ-η3:η3-C10H16)RuCl2]2". . p. 1 - 5. Retrieved 2014.
• 2、 Uzarewicz,Dresler. "The reaction of cyclic allylic alcohols with aliphatic alcohols in the presence of cerium(III) chloride". . p. 181 - 195. Retrieved 2007/10/03.