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274658

Sigma-Aldrich

2,3,4,5-Tetramethyl-2-cyclopentenone, mixture of cis and trans

95%

Synonym(s):

2,3,4,5-Tetramethyl-2-cyclopenten-1-one, 2,3,4,5-Tetramethylcyclopenten-1-one, 2,3,4,5-Tetramethylcyclopentenone, Tetramethylcyclopent-2-enone

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About This Item

Empirical Formula (Hill Notation):
C9H14O
CAS Number:
54458-61-6
Molecular Weight:
138.21
Beilstein/REAXYS Number:
2324088
MDL number:
MFCD00010248
UNSPSC Code:
12352100
PubChem Substance ID:
24856595
NACRES:
NA.22

assay

95%

form

liquid

refractive index

n20/D 1.476 (lit.)

bp

100 °C/30 mmHg (lit.)

density

0.917 g/mL at 25 °C (lit.)

SMILES string

CC1C(C)C(=O)C(C)=C1C

InChI

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

InChI key

ARUAYSANQMCCEN-UHFFFAOYSA-N

Application

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.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

163.4 °F - closed cup

flash_point_c

73 °C - closed cup

ppe

Eyeshields, Gloves, multi-purpose combination respirator cartridge (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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3-Methyl-2-cyclopentenone

Li Wang et al.
Dalton transactions (Cambridge, England : 2003), 41(24), 7350-7357 (2012-05-15)
Two new chiral pre-ligands, (R)-3,3'-bis(tetramethylcyclopentadienyl)-2,2'-bismethoxy-1,1'-bisnaphthalene (1) and (R)-3-tetramethylcyclopentadienyl-2,2'-bismethoxy-1,1'-bisnaphthalene (2), were synthesized by reaction of (R)-3,3'-dilithium-2,2'-bismethoxy-1,1'-bisnaphthalene with 2,3,4,5-tetramethyl-2-cyclopentenone at room temperature. Treatment of the pre-ligands 1 and 2 with butyllithium and Me(3)SiCl first, and subsequently with TiCl(4) (2 and 1 equiv

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