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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[1].

Application

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

Molecule studied for its pharmacological activity as a KSP inhibitor

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Takuya Ogawa et al.
Frontiers in microbiology, 11, 1104-1104 (2020-06-13)
Eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA), which belong to the same class of long chain ω-3 polyunsaturated fatty acids (PUFAs), are present in marine γ-proteobacteria. In contrast to their de novo biosynthesis that has been intensively studied, their metabolic
Lara T Meital et al.
Scientific reports, 9(1), 12978-12978 (2019-09-12)
Abdominal aortic aneurysm (AAA) is associated with inflammation and oxidative stress, the latter of which contributes to activation of macrophages, a prominent cell type in AAA. Omega-3 polyunsaturated fatty acids (n-3 PUFAs) have been reported to limit oxidative stress in
Bernard Cuenoud et al.
Nutrients, 12(4) (2020-04-11)
Numerous benefits are attributed to omega-3 fatty acids (OM3) especially in cardiovascular health. However, bioavailability and clinical efficacy depend on numerous factors, including OM3 form, food matrix effects (especially the lipid content of the diet), and metabolic capacity. Here, we
Mayssa Hachem et al.
Nutrients, 12(1) (2020-01-23)
AceDoPC® is a structured glycerophospholipid that targets the brain with docosahexaenoic acid (DHA) and is neuroprotective in the experimental ischemic stroke. AceDoPC® is a stabilized form of the physiological 2-DHA-LysoPC with an acetyl group at the sn1 position; preventing the
Suhn Hyung Kim et al.
Nutrients, 11(7) (2019-06-30)
Intracellular Ca2+ homeostasis is commonly disrupted in acute pancreatitis. Sustained Ca2+ release from internal stores in pancreatic acinar cells (PACs), mediated by inositol triphosphate receptor (IP3R) and the ryanodine receptor (RyR), plays a key role in the initiation and propagation
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