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184861

Sigma-Aldrich

Naphthalene-bis(hexachlorocyclopentadiene) adduct

Synonym(s):

DHA, NSC 122892

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About This Item

Empirical Formula (Hill Notation):
C20H8Cl12
CAS Number:
5696-92-4
Molecular Weight:
673.71
EC Number:
227-171-6
MDL number:
MFCD00167975
UNSPSC Code:
12352100
PubChem Substance ID:
24850660
NACRES:
NA.22

form

solid

mp

208-210 °C (lit.)

functional group

chloro

SMILES string

ClC1=C(Cl)[C@@]2(Cl)C3C(C4C(c5ccccc35)[C@@]6(Cl)C(Cl)=C(Cl)[C@]4(Cl)C6(Cl)Cl)[C@]1(Cl)C2(Cl)Cl

InChI

1S/C20H8Cl12/c21-11-13(23)17(27)9-7(15(11,25)19(17,29)30)5-3-1-2-4-6(5)8-10(9)18(28)14(24)12(22)16(8,26)20(18,31)32/h1-4,7-10H/t7?,8?,9?,10?,15-,16+,17+,18-

InChI key

ULBZLTIPWBXWCY-QDCKJYKTSA-N

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General description

Naphthalene-bis(hexachlorocyclopentadiene) adduct is precursor to substituted naphthalenes which are otherwise difficult to synthesize.

Application

Naphthalene-bis(hexachlorocyclopentadiene) adduct was used in the synthesis of:
  • 2,3-diiodonaphthalene via iodination in methanesulfonic acid
  • 2,3-dibromonapthalene via bromination
Reactant involved in iodination and retro Diels-alder reactions

Molecule studied for its pharmacological activity as a KSP inhibitor

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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