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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:
91-17-8
Molecular Weight:
138.25
Beilstein:
878165
EC Number:
202-046-9
MDL number:
MFCD00004130
UNSPSC Code:
12352001
PubChem Substance ID:
329798742
NACRES:
NA.21
grade:
reagent grade
bp:
189-191 °C (lit.)
vapor pressure:
42 mmHg ( 92 °C)
741 mmHg ( 188 °C)

grade

reagent grade

Quality Level

100

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

H226,H304,H314,H331,H410

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

PRTR

Class II Designated Chemical Substances

FSL

Group 4: Flammable liquids
Type 2 petroleums
Hazardous rank III
Water insoluble liquid

ISHL Indicated Name

Substances Subject to be Indicated Names

ISHL Notified Names

Substances Subject to be Notified Names

JAN Code

D251-BULK:
D251-10L:
D251-500ML:
D251-18L-CS:
D251-VAR-D:
D251-VAR:
D251-2.5L:
D251-18L:
D251-4L:
D251-1L:
D251-20L:

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Certificates of Analysis (COA)

Lot/Batch Number
STBK4166
STBK3960
STBK2918
STBJ4144
STBJ1884

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Joseph B Lim et al.
The journal of physical chemistry. B, 116(1), 203-210 (2011-12-06)
A modification of the CHARMM36 lipid force field (C36) for cholesterol, henceforth, called C36c, is reported. A fused ring compound, decalin, was used to model the steroid section of cholesterol. For decalin, C36 inaccurately predicts the heat of vaporization (~10
Franco Cataldo et al.
Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy, 77(5), 998-1004 (2010-09-25)
Oleum (fuming sulphuric acid), a well known superacid, was used as medium for the generation of the radical cation of a series of selected PAHs. The resulting radical cation spectra were studied by electronic absorption spectroscopy. Not only common PAHs
D Kruk et al.
The Journal of chemical physics, 137(4), 044512-044512 (2012-08-03)
(1)H relaxation dispersion of decalin and glycerol solutions of nitroxide radicals, 4-oxo-TEMPO-d(16)-(15)N and 4-oxo-TEMPO-d(16)-(14)N was measured in the frequency range of 10 kHz-20 MHz (for (1)H) using STELAR Field Cycling spectrometer. The purpose of the studies is to reveal how
Shaik Anwar et al.
Organic letters, 13(9), 2200-2203 (2011-04-12)
An efficient and unprecedented organocatalytic reaction of γ-nitroketones with α,β-unsaturated aldehydes to give polyfunctionalized [4.4.0] bicyclic skeletons was developed. The diphenylprolinol silyl ether mediated nitro-Michael/Aldol reaction afforded the hexa-substituted decalin carboaldehydes with excellent diastereo- and enantioselectivity (up to >99:1 dr
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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