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Merck
CN

184861

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
NACRES:
NA.22
PubChem Substance ID:
24850660
UNSPSC Code:
12352100
EC Number:
227-171-6
MDL number:
MFCD00167975
Form:
solid

Key Documents

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form

solid

InChI key

ULBZLTIPWBXWCY-QDCKJYKTSA-N

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-

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

mp

208-210 °C (lit.)

functional group

chloro

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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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
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European journal of nutrition, 59(3), 1205-1218 (2019-05-11)
Most children do not meet dietary guidelines for fish intake. Fish is the main source of EPA (20:5n-3), DHA (22:6n-3) and vitamin D, but may replace better iron sources such as meat. We investigated if intake of 300 g/week oily fish
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
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
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
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