2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE Chemical Properties

Boiling point:

100 °C30 mm Hg(lit.)

Density 

0.927 g/mL at 20 °C(lit.)

refractive index 

n20/D 1.476

Flash point:

164 °F

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform, Methanol

form 

Oil

color 

Clear Colourless

Specific Gravity

0.917

Water Solubility 

Not miscible with water.

BRN 

2324088

InChI

InChI=1S/C9H14O/c1-5-6(2)8(4)9(10)7(5)3/h5,7H,1-4H3

InChIKey

ARUAYSANQMCCEN-UHFFFAOYSA-N

SMILES

C1(=O)C(C)C(C)C(C)=C1C

CAS DataBase Reference

54458-61-6(CAS DataBase Reference)

Safety Information

Safety Statements 

23-24/25-35-3/9/49-43-36-15

WGK Germany 

3

HS Code 

29142990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE Usage And Synthesis

Uses

2,3,4,5-Tetramethyl-2-cyclopentenone can be used as organic synthesis intermediates and pharmaceutical intermediates, mainly used in laboratory research and development processes and chemical production processes.

Uses

2,3,4,5-Tetramethyl-2-cyclopentenone was used in the synthesis of chiral pre-ligands, (R)-3,3?-bis(tetramethylcyclopentadienyl)-2,2?-bismethoxy-1,1?-bisnaphthalene and (R)-3-tetramethylcyclopentadienyl-2,2?-bismethoxy-1,1?-bisnaphthalene by reacting with (R)-3,3?-dilithium-2,2?-bismethoxy-1,1?-bisnaphthalene.

Synthesis

In a bottom round flask equipped with a mechanical stirrer, a dropping funnel and a reflux condenser was loaded 2000g (23.2 mol) of the starting ketone with 75% w/w of butylacetate as the solvent, 0.35 molar equivalents of anhydrous magnesium chloride and the aforementioned titanium catalytic solution containing 0.06 molar equivalents of the trichloropropoxytitanium complex. The resulting suspension was stirred vigorously and allowed to heat to 90°C. Then 2 molar equivalents of the acetaldehyde were added dropwise over 3h at 90°C. The reaction was continued for an additional hour and cooled to 40°C. The reaction mixture was hydrolysed with a 10% aqueous acetic acid solution and neutralised with a 20% aqueous potassium carbonate solution. The resulting organic phase was directly fractionated into a laboratory Sulzer packed column, to afford the title compound, as a mixture of isomers trans:cis = 85:15, in 27 % yield and the enone (II) (i.e. 4-methyl-4-hexen-3-one) in 31 % yield. mixture of isomers trans:cis = (B.p. = 70-80°C at P = 8 mbar); 4-methyl-4-hexen-3-one = (B.p. = 45-65°C at P = 8 mbar). 1H-NMR (isomer trans): 1.15 (d 3H); 1.19 (d 3H); 1.68 (s 3H); 1.88 (m 1H); 1.98 (s 3H); 2.25 (m 1H). 13C-NMR (isomer trans): 8.5; 14.6; 15.1 ; 17.7; 46.2; 48.4; 134.5; 171.6; 21 1.0.

2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE(54458-61-6)Related Product Information

• Cyclopentene
• 2-Cyclopenten-1-one
• TRANS-2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE
• SALOR-INT L162698-1EA
• SALOR-INT L161136-1EA
• SALOR-INT L160792-1EA
• SALOR-INT L162744-1EA
• 2,3,4,5-TETRAMETHYL-2-CYCLOPENTENONE