1,3,5,5-Tetramethyl-1,3-cyclohexadiene

Base Information

• Chemical Name: 1,3,5,5-Tetramethyl-1,3-cyclohexadiene
• CAS No.: 4724-89-4
• Molecular Formula: C10H16
• Molecular Weight: 136.237
• European Community (EC) Number: 680-729-4
• NSC Number: 123453
• UNII: LW73Z302UP
• DSSTox Substance ID: DTXSID0063575
• Nikkaji Number: J421.737C
• Wikidata: Q81990837
• Mol file: 4724-89-4.mol

Synonyms:1,3,5,5-Tetramethyl-1,3-cyclohexadiene;4724-89-4;1,3,5,5-tetramethylcyclohexa-1,3-diene;1,3-Cyclohexadiene, 1,3,5,5-tetramethyl-;LW73Z302UP;NSC 123453;NSC-123453;NSC123453;UNII-LW73Z302UP;1, 1,3,5,5-tetramethyl-;DTXSID0063575;1,3,5,5-tetramethylcyclohexadiene;MFCD00045518;AKOS025295352;1,5,5-Tetramethyl-1,3-cyclohexadiene;FT-0635410;T1718;D92512

Chemical Property of 1,3,5,5-Tetramethyl-1,3-cyclohexadiene

Chemical Property:

• Vapor Pressure: 2.85mmHg at 25°C
• Refractive Index: 1.4650
• Boiling Point: 162.3°Cat760mmHg
• Flash Point: 38.9°C
• PSA: 0.00000
• Density: 0.813g/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: 192

Purity/Quality:

98%,99%, ^*data from raw suppliers

1,3,5,5-Tetramethyl-1,3-cyclohexadiene >92.0%(GC) ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 1,3,5,5-Tetramethyl-1,3-cyclohexadiene

There total 9 articles about 1,3,5,5-Tetramethyl-1,3-cyclohexadiene 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:

Pinene (80-56-8,177698-18-9,25766-18-1) → 1,3,5,5-tetramethyl-1,3-cyclohexadiene (4724-89-4) + (Z)-ocimene (3338-55-4,1856-63-9) + α-pyronene (514-94-3) + limonene. (138-86-3,555-08-8,8022-90-0,9003-73-0,95327-98-3)

Guidance literature:

In chloroform; at 400 ℃; Further Variations:; Temperatures; Product distribution;

DOI:10.1002/ejoc.200601098

Reference yield:

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + methylmagnesium bromide (75-16-1) + methyl iodide (74-88-4) → 3,3,5,5-tetramethylcyclohexanone (14376-79-5) + 1,3,5,5-tetramethyl-1,3-cyclohexadiene (4724-89-4) + 2,3,3,5,5-Pentamethylcyclohexanon (58367-83-2)

Guidance literature:

With copper(I) bromide; Yield given. Multistep reaction. Yields of byproduct given; 1) ether, reflux, 1.5 h, 2) ether, THF, HMPT, reflux, 3 h;

Reference yield:

3,5,5-Trimethylcyclohex-2-en-1-one (78-59-1) + methylmagnesium chloride (676-58-4) → 1,3,5,5-tetramethyl-1,3-cyclohexadiene (4724-89-4)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; acetic acid; benzene;

upstream raw materials:

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

methylmagnesium bromide

2,4,6-trimethyl-2,5-heptadien-1-ol

3-Hydroxy-1,3,5,5-Tetramethylcyclohexen

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 2015/02/19.
• 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.