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D251

Sigma-Aldrich

Decahydronaphthalene, mixture of cis + trans

reagent grade, 98%

Synonym(s):

Decalin

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About This Item

Empirical Formula (Hill Notation):
C10H18
CAS Number:
Molecular Weight:
138.25
Beilstein:
878165
EC Number:
MDL number:
UNSPSC Code:
12352001
PubChem Substance ID:
NACRES:
NA.21

grade

reagent grade

Quality Level

vapor density

4.76 (vs air)

vapor pressure

42 mmHg ( 92 °C)
741 mmHg ( 188 °C)

Assay

98%

form

liquid

autoignition temp.

482 °F

expl. lim.

0.7-4.9 %, 100 °F

refractive index

n20/D 1.474 (lit.)

bp

189-191 °C (lit.)

mp

−125 °C (lit.)

density

0.896 g/mL at 25 °C (lit.)

SMILES string

C1CCC2CCCCC2C1

InChI

1S/C10H18/c1-2-6-10-8-4-3-7-9(10)5-1/h9-10H,1-8H2

InChI key

NNBZCPXTIHJBJL-UHFFFAOYSA-N

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General description

Decahydronaphthalene, mixture of cis + trans is a bicyclic organic compound that can be used as an industrial solvent. It can be prepared by the complete catalytic hydrogenation of naphthalene or tetralin.

Application

Decahydronaphthalene, mixture of cis+ trans can be used as a solvent in the:
  • Distannoxane-catalyzed synthesis of aliphatic polyesters via polycondensation.
  • Intramolecular carbonyl-ene cyclocondensation of oxygenated o-phenylallylbenzaldehydes to synthesize substituted naphthalenes.

Legal Information

Decalin is a trademark of Sigma-Aldrich Co. LLC

Signal Word

Danger

Hazard Statements

Hazard Classifications

Acute Tox. 3 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1 - Asp. Tox. 1 - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1C

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

134.6 °F - closed cup

Flash Point(C)

57 °C - closed cup


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ken K Qian et al.
Journal of pharmaceutical sciences, 100(7), 2801-2815 (2011-02-22)
Spontaneous crystalline-to-amorphous phase transformation of organic or medicinal molecules in the presence of mesoporous materials has been observed, for which pathway was suggested to be via the vapor phase, that is, sublimation of the crystalline molecules followed by adsorption on
Mohit Kumar et al.
Nanoscale, 3(5), 2130-2133 (2011-03-30)
Naphthalene diimide (NDI) bolaamphiphilic molecules (1) self-assemble in water to form organic nanoparticles, which exhibit self-assembly induced preassociated excimer formation and hence an enhanced green fluorescence.
Sabir Hussain et al.
Journal of the American Chemical Society, 133(6), 1614-1617 (2011-01-25)
Decalins bearing two axial -NHCONHAr substituents and an ester-linked alkyl side chain have been synthesized and studied as anion receptors and transporters. The design relates to steroid-based "cholapods" but is more compact and less intrinsically lipophilic. Transport rates depend on
Christie Aroulanda et al.
The journal of physical chemistry. B, 113(31), 10628-10640 (2009-07-16)
The conformational dynamics and orientational behavior of two model cyclic molecules, cis-decalin (cis-dec) and tetrahydrofurane (THF), dissolved in weakly ordering, polypeptidic chiral liquid crystals (CLCs) are theoretically discussed and experimentally investigated using deuterium and carbon-13 NMR spectroscopies. The analysis of
Xiaozu Liu et al.
Organic letters, 14(11), 2886-2889 (2012-05-19)
A concise enantioselective synthesis of (-)-teucvidin has been achieved. Our synthetic strategy involved the diastereoselective Michael/Conia-ene cascade cyclization reaction for rapid establishment of the cis-decalin skeleton with three new stereogenic centers in one pot (72%, single diastereomer), the epoxidation/dealkoxycarbonylation protocol

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