1-Methyl-1,3-cyclohexadiene

Base Information

• Chemical Name: 1-Methyl-1,3-cyclohexadiene
• CAS No.: 1489-56-1
• Deprecated CAS: 68739-08-2,80789-06-6
• Molecular Formula: C7H10
• Molecular Weight: 94.1564
• Hs Code.: 2902199090
• European Community (EC) Number: 250-269-5,216-071-8
• UNII: NZ9H475GT1
• DSSTox Substance ID: DTXSID70892095
• Nikkaji Number: J206.693I
• Wikidata: Q27285120
• Metabolomics Workbench ID: 44932
• Mol file: 1489-56-1.mol

Synonyms:1-Methyl-1,3-cyclohexadiene;1-Methylcyclohexa-1,3-diene;1489-56-1;Methylcyclohexadiene;5,6-Dihydrotoluene;2,3-Dihydrotoluene;1,3-Cyclohexadiene, 1-methyl-;30640-46-1;Cyclohexadiene, methyl-;UNII-NZ9H475GT1;NZ9H475GT1;EINECS 216-071-8;lemon hexadiene;3h-toluene;Methyl-Cyclohexadiene;Cyclohexadiene, methyl;1-methyl-cyclohexa-1,3-diene;DTXSID70892095;CHEBI:165805;EINECS 250-269-5;MFCD01074681;AKOS006275295;SY292105;FT-0694752;FEMA NO. 4311, METHYLCYCLOHEXADIENE-;Q27285120

Chemical Property of 1-Methyl-1,3-cyclohexadiene

Chemical Property:

• Vapor Pressure: 22.3mmHg at 25°C
• Refractive Index: 1.4453 (estimate)
• Boiling Point: 115.8°Cat760mmHg
• Flash Point: 4°C
• PSA: 0.00000
• Density: 0.848g/cm³
• LogP: 2.28270
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 94.078250319
• Heavy Atom Count: 7
• Complexity: 107

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CCC1
• Description: By dehalogenation of 1,2-dibromo-l-methyl cyclohexane with sodium ethoxide; purified by distillation over metallic sodium.

Technology Process of 1-Methyl-1,3-cyclohexadiene

There total 35 articles about 1-Methyl-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: 73.0%

2-methylcyclohex-2-enyl phenyl sulphone (131179-51-6) → 1-methyl-1,3-cyclohexadiene (1489-56-1)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 80 ℃; for 6h;

DOI:10.1021/jo00002a061

Reference yield: 35.0%

cyclohexa-1,3-dien-1-yl trifluoromethanesulfonate (63028-11-5) + methylmagnesium chloride (676-58-4) → 1-methyl-1,3-cyclohexadiene (1489-56-1)

Guidance literature:

With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); In diethyl ether; at -78 - 0 ℃;

DOI:10.1021/jacs.8b09974

Reference yield: 14.3%

5-methyl-1,3-cyclohexadiene (19656-98-5) → 3-methyl-1-cyclohexene (591-48-0) + 4-methylcyclohexene (591-47-9) + 2-methylcyclohexa-1,3-diene (1489-57-2) + 1-methyl-1,3-cyclohexadiene (1489-56-1) + toluene (108-88-3,15644-74-3,16713-13-6)

Guidance literature:

rhodium(III) chloride; In nitromethane; water; at 45 ℃; for 1.33333h; Product distribution; Mechanism; variation of time; with Kat₂;

upstream raw materials:

1-methylcyclohex-2-en-1-ol

1-methyl-cyclohexane-1,3-diyldiamine

3-methylcyclohexen-2-one

1-methyl-4-oxo-cyclohex-2-enecarboxylic acid ethyl ester

Downstream raw materials:

1-Methyl-bicyclo<2.2.2>octan-2-carbonsaeure-ethylester

Refernces

• 1、 Liu,Burnell. "Synthetic studies toward the kempane diterpenes: Preparation of the ring system". . p. 9584 - 9585. Retrieved 1997.
• 2、 Mironov et al.. "". . . Retrieved 1971.
• 3、 Miranov et al.. "". . . Retrieved 1973.
• 4、 Trost, Barry M.,Huang, Zhongxing. "Catalytic (3+2) Palladium-Aminoallyl Cycloaddition with Conjugated Dienes". supporting information. p. 6396 - 6399. Retrieved 2019/04/13.
• 5、 Hatano, Manabu,Sakamoto, Tatsuhiro,Mizuno, Tomokazu,Goto, Yuta,Ishihara, Kazuaki. "Chiral Supramolecular U-Shaped Catalysts Induce the Multiselective Diels-Alder Reaction of Propargyl Aldehyde". supporting information. p. 16253 - 16263. Retrieved 2018/11/27.