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544418

Sigma-Aldrich

3-Benzylidene-2,4-pentanedione

97%

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Linear Formula:
CH3COC(=CHC6H5)COCH3
CAS Number:
4335-90-4
Molecular Weight:
188.22
EC Number:
224-382-5
MDL number:
MFCD00014990
UNSPSC Code:
12352100
PubChem Substance ID:
24878761
NACRES:
NA.22

Assay

97%

refractive index

n20/D 1.583 (lit.)

bp

185-188 °C/15 mmHg (lit.)

density

1.081 g/mL at 25 °C (lit.)

SMILES string

CC(=O)\C(=C\c1ccccc1)C(C)=O

InChI

1S/C12H12O2/c1-9(13)12(10(2)14)8-11-6-4-3-5-7-11/h3-8H,1-2H3

InChI key

NYRGMNMVISROGJ-UHFFFAOYSA-N

General description

3-Benzylidene-2,4-pentanedione (BPD) can be prepared by reacting benzaldehyde with 2,4-pentanedione in the presence of a base.

Application

3-Benzylidene-2,4-pentanedione may be used in the preparation of:
  • Five membered cyclic oxyphosphoranes by reacting with phosphonite esters.
  • 5-Hydroxy-N-substituted-2H-pyrrol-2-ones by reacting with alkyl isocyanides.
  • 3-Benzylidene-2,4-bis (trimethylsilyloxy)-1,4-pentadiene via trimethylsilylation.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

WGK

WGK 3

Flash Point(F)

>230.0 °F

Flash Point(C)

> 110 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

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3-Benzylidene-2, 4-bis (trimethylsilyloxy)-1, 4-pentadiene; Synthesis and its diene-transmissive Diels-Alder reaction.
Tsuge O, et al.
Chemistry Letters (Jpn), 2, 239-242 (1983)
5-Hydroxy-2H-pyrrol-2-ones and not 2-aminofurans are the cycloaddition products between alkyl isocyanides and benzyliden-1,3-diketones.
Quai M, et al.
Tetrahedron Letters, 45(7), 1413-1416 (2004)
Stereoisomerism at phosphorus in cyclic oxyphosphoranes. Reaction of phosphonite and phosphinite esters with 3-benzylidene-2, 4-pentanedione.
Ramirez F, et al.
Journal of the American Chemical Society, 90(5), 1275-1280 (1968)

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