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264679

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde

Name: 2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde
Brand: ALDRICH

technical grade, 80%

Synonym(s):

β-Homocyclocitral

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₈O

CAS Number:

472-66-2

Molecular Weight:

166.26

NACRES:

NA.22

PubChem Substance ID:

24856029

UNSPSC Code:

12352100

EC Number:

207-454-0

MDL number:

MFCD00012057

Assay:

80%

Form:

liquid

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Properties

grade

technical grade

Quality Level

100

assay

80%

form

liquid

refractive index

n20/D 1.485 (lit.)

bp

58-59 °C/0.4 mmHg (lit.)

density

0.941 g/mL at 25 °C (lit.)

functional group

aldehyde

SMILES string

[H]C(=O)CC1=C(C)CCCC1(C)C

InChI

1S/C11H18O/c1-9-5-4-7-11(2,3)10(9)6-8-12/h8H,4-7H2,1-3H3

InChI key

VHTFHZGAMYUZEP-UHFFFAOYSA-N

Description

Application

2,6,6-Trimethyl-1-cyclohexene-1-acetaldehyde can be used as a starting material to prepare:

(±)-Aeginetolide by oxidation in the presence of meta-chloroperoxybenzoic acid (m-CPBA).
(±)-Dihydroactinidiolide (a C₁₁-terpenic lactone) via dehydration of key intermediate aeginetolide.

It can also be used as a key intermediate to synthesize drimane-related sesquiterpenes and substituted retinoic acid analogs.

Other Notes

Contains β-cyclocitral

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pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

10 - Combustible liquids

wgk

WGK 3

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Improved Synthesis of 2, 6, 6-Trimethyl-1-cyclohexene-1-acetaldehyde, A Key Intermediate for Drimane-Related Sesquiterpenes

de Jong JC, et al.

Synthetic Communications, 20(4), 589-596 (1990)

Improved Synthesis of 2, 6, 6-Trimethyl-1-cyclohexene-1-acetaldehyde, A Key Intermediate for Drimane-Related Sesquiterpenes.