544418
3-Benzylidene-2,4-pentanedione
97%
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About This Item
Linear Formula:
CH3COC(=CHC6H5)COCH3
CAS Number:
Molecular Weight:
188.22
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352100
EC Number:
224-382-5
MDL number:
Assay:
97%
assay
97%
InChI key
NYRGMNMVISROGJ-UHFFFAOYSA-N
InChI
1S/C12H12O2/c1-9(13)12(10(2)14)8-11-6-4-3-5-7-11/h3-8H,1-2H3
SMILES string
CC(=O)\C(=C\c1ccccc1)C(C)=O
refractive index
n20/D 1.583 (lit.)
bp
185-188 °C/15 mmHg (lit.)
density
1.081 g/mL at 25 °C (lit.)
functional group
ketone, phenyl
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
Storage Class
10 - Combustible liquids
wgk
WGK 3
flash_point_f
>230.0 °F - closed cup
flash_point_c
> 110 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
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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)
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)
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