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290971

Sigma-Aldrich

2,2-Dimethyl-4-pentenal

technical grade, 90%, contains 1000 ppm hydroquinone as stabilizer

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About This Item

Linear Formula:
H2C=CHCH2C(CH3)2CHO
CAS Number:
5497-67-6
Molecular Weight:
112.17
MDL number:
MFCD00010699
UNSPSC Code:
12352100
PubChem Substance ID:
24857501
NACRES:
NA.22

grade

technical grade

Assay

90%

contains

1000 ppm hydroquinone as stabilizer

refractive index

n20/D 1.4203 (lit.)

bp

124-125 °C (lit.)

density

0.825 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC(C)(CC=C)C=O

InChI

1S/C7H12O/c1-4-5-7(2,3)6-8/h4,6H,1,5H2,2-3H3

InChI key

DXSDIWHOOOBQTJ-UHFFFAOYSA-N

Application

2,2-Dimethyl-4-pentenal has been used:
  • as electrophile in the synthesis of rearranged bicyclo[6.3.0]undecane isoprenoid skeleton of cyclooctenoid sesquiterpene dactylol and 3a-epi-dactylol
  • in the preparation of imine ligand via condensation with primary amine

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 2

Flash Point(F)

64.4 °F - closed cup

Flash Point(C)

18 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
BGBC0650V
39998PJ
05325JE
04807JE
14015PA

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Latent olefin metathesis catalysts featuring chelating alkylidenes.
Hejl A, et al.
Organometallics, 25(26), 6149-6154 (2006)
Alois Fürstner et al.
The Journal of organic chemistry, 61(25), 8746-8749 (1996-12-13)
A straightforward total synthesis of the cyclooctenoid sesquiterpene dactylol (1) and of 3a-epi-dactylol (13) has been achieved in six synthetic operations. The unusual rearranged bicyclo[6.3.0]undecane isoprenoid skeleton of these target molecules has been formed via an initial three-component coupling triggered

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