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549762

Sigma-Aldrich

Ethyl 6,8-dichlorooctanoate

95%

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About This Item

Linear Formula:
CH3CH2OCO(CH2)4CH(Cl)(CH2)2Cl
CAS Number:
1070-64-0
Molecular Weight:
241.15
EC Number:
435-080-1
MDL number:
MFCD01711127
UNSPSC Code:
12352100
PubChem Substance ID:
24874721

assay

95%

refractive index

n20/D 1.462 (lit.)

density

1.107 g/mL at 25 °C (lit.)

SMILES string

CCOC(=O)CCCCC(Cl)CCCl

InChI

1S/C10H18Cl2O2/c1-2-14-10(13)6-4-3-5-9(12)7-8-11/h9H,2-8H2,1H3

InChI key

RFYDWSNYTVVKBR-UHFFFAOYSA-N

Application

Ethyl 6,8-dichlorooctanoate may be used as a starting material in the synthesis of 6-selenolipoic acid and α-lipoic acid derivatives, which show potent anticancer activity.
It may also be used as a starting material to synthesize:
  • 6,8-Dibenzylmercaptooctanoic acid, an intermediate for the preparation of DL-α-lipoic acid.
  • Ethyl 5,7-dichloroheptanoate, an intermediate for the preparation of DL-1,2-dithiolane-3-butyric acid.
  • 7-Bromo-1,3-dichloroheptane, an intermediate for the preparation of DL-12-dithiolane-3-butanesulfonamide.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H317,H411

Hazard Classifications

Aquatic Chronic 2 - Skin Sens. 1

Storage Class

10 - Combustible liquids

wgk_germany

WGK 2

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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Certificates of Analysis (COA)

Lot/Batch Number
05615TI

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Syntheses of DL-a-lipoic acid.
Reed LJ and Niu CI.
Journal of the American Chemical Society, 77(2), 416-419 (1955)
Synthesis of DL-1, 2-Dithiolane-3-caproic Acid and DL-1, 2-Dithiolane-3-butyric Acid, Homologs of a-Lipoic Acid.
Thomas RC and Reed LJ.
Journal of the American Chemical Society, 78(23), 6151-6153 (1956)
Synthesis of some monoselenolipoic acid derivatives and their biological evaluation as anticancer agents.
Xu F, et al.
J. Chem. Res. (M), 37(5), 311-314 (2013)
Synthesis of DL-1, 2-Dithiolane-3-butanesulfonamide, an Analog of a-Lipoic Acid.
Thomas RC and Reed LJ.
Journal of the American Chemical Society, 78(23), 6150-6151 (1956)
Shi-Jie Zhang et al.
Bioorganic & medicinal chemistry letters, 20(10), 3078-3083 (2010-04-21)
alpha-Lipoic acid derivatives were synthesized and evaluated for their in vitro anticancer activities against NCI-460, HO-8910, KB, BEL-7402, and PC-3 cell lines. The results, for most compounds exhibited dose-dependent inhibitory property and several compounds had good inhibitions at the dose

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