alpha-Cyclocitral

Base Information

• Chemical Name: alpha-Cyclocitral
• CAS No.: 432-24-6
• Deprecated CAS: 59462-59-8
• Molecular Formula: C₁₀H₁₆O
• Molecular Weight: 152.236
• European Community (EC) Number: 207-080-8
• UNII: 762EWR23N8
• DSSTox Substance ID: DTXSID60861932
• Nikkaji Number: J127.247K
• Wikidata: Q27266437
• Metabolomics Workbench ID: 47020
• Mol file: 432-24-6.mol

Synonyms:alpha-Cyclocitral;432-24-6;alpha-cyclociral;2,6,6-Trimethylcyclohex-2-ene-1-carbaldehyde;2-Cyclohexene-1-carboxaldehyde, 2,6,6-trimethyl-;Filipendulal;alpha -cyclocitral;2,6,6-Trimethyl-2-cyclohexen-1-carboxaldehyde;.alpha.-Cyclocitral;1-Formyl-2,6,6-trimethyl-2-cyclohexene;2,6,6-Trimethyl-2-cyclohexene-1-carboxaldehyde;UNII-762EWR23N8;762EWR23N8;EINECS 207-080-8;2,6,6-trimethylcyclohex-2-enecarbaldehyde;AI3-37230;2,6,6-Trimethyl-2-cyclohexene-1-carbaldehyde;2,6,6-Trimethylcyclohex-2-en-1-carboxaldehyde;a-Cyclocitral;2,6,6-Trimethyl-cyclohex-2-enecarbaldehyde;alpha-cyclociral, AldrichCPR;CYCLOCITRAL, .ALPHA.-;SCHEMBL1782746;DTXSID60861932;CHEBI:171968;(+/-)-.ALPHA.-CYCLOCITRAL;AKOS006327717;FEMA NO. 3639, .ALPHA.-;.ALPHA.-CYCLOCITRAL, (+/-)-;CS-0435919;FT-0653367;F77896;2,6,6-trimethyl-1-cyclohex-2-enecarboxaldehyde;2,6,6-trimethyl-cyclohex-2-ene-1-carbaldehyde;2,6,6-Trimethyl-2-cyclohexene-1-carbaldehyde #;A826227;J-803004;Q27266437;2,6,6 - trimethylcyclohex - 2 - ene - 1 - carbaldehyde

Chemical Property of alpha-Cyclocitral

Chemical Property:

• Appearance/Colour: Pale Yellow Oil
• Vapor Pressure: 0.382mmHg at 25°C
• Refractive Index: 1.5
• Boiling Point: 197.3 °C at 760 mmHg
• Flash Point: 64.5 °C
• PSA: 17.07000
• Density: 0.935 g/cm³
• LogP: 2.56780
• Storage Temp.: Amber Vial, -20°C Freezer, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 152.120115130
• Heavy Atom Count: 11
• Complexity: 189

Purity/Quality:

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

α-Cyclocitral ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CCCC(C1C=O)(C)C
• Uses: α-Cyclocitral (cas# 432-24-6) is a compound useful in organic synthesis.

Technology Process of alpha-Cyclocitral

There total 37 articles about alpha-Cyclocitral 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: 97.5%

2,6,6-trimethyl-cyclohex-3-enecarbaldehyde (91056-62-1) → α-cyclocitral (14505-74-9,41721-03-3,59462-59-8,432-24-6)

Guidance literature:

With ammonium chloride; triphenylphosphine; nickel dichloride; zinc; In toluene; at 55 ℃; for 1.7h; Large scale;

Reference yield: 95.0%

(1R*,2R*S*,3S*R*)-2,3-epoxy-2,6,6-trimethylcyclohexane-1-carbaldehyde → α-cyclocitral (14505-74-9,41721-03-3,59462-59-8,432-24-6)

Guidance literature:

With 2,4,6-trimethyl-pyridine; bis(cyclopentadienyl)titanium dichloride; manganese; 2,4,6-collidine hydrochloride; Inert atmosphere;

DOI:10.1055/s-0028-1083174

Reference yield: 87.0%

(8,8-dimethyl-4-methylene)-1-oxaspiro<2.5>octane (54345-56-1) → α-cyclocitral (14505-74-9,41721-03-3,59462-59-8,432-24-6) + 2,2-dimethyl-6-methylenecyclohexane-1-carbaldehyde (432-23-5,4350-73-6)

Guidance literature:

With zinc dibromide; In benzene; for 0.75h; Heating;

DOI:10.1016/S0040-4039(00)60109-0

upstream raw materials:

(E/Z)-3,7-dimethyl-2,6-octadienal

2-cyano-5,9-dimethyl-deca-2,4,8-trienoic acid

(+/-)-α-cyclogeraniol

(+/-)-α-cyclogeranic acid

Downstream raw materials:

4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one

alpha-ionone

borat

1-(2,6,6-trimethyl-2-cyclohexenyl)-3-buten-1-ol

Refernces

• 1、 Mayo,Silk,Abeysekera,MaGee. "Synthesis of three putative kairomones of the beech leaf-mining weevil Orchestes fagi (L.)". supporting information. p. 1124 - 1132. Retrieved 2016/07/21.
• 2、 Gansaeuer, Andreas,Piestert, Frederik,Huth, Inga,Lauterbach, Thorsten. "Nitriles and carbonyl groups as acceptors in titanocene-catalyzed radical cyclizations". scheme or table. p. 3509 - 3515. Retrieved 2009/05/26.