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Merck
CN

45778

1,2-Dihydronaphthalene

analytical standard

Synonym(s):

Dialin

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About This Item

Empirical Formula (Hill Notation):
C10H10
CAS Number:
447-53-0
Molecular Weight:
130.19
EC Number:
207-183-8
UNSPSC Code:
41116107
PubChem Substance ID:
329756948
Beilstein/REAXYS Number:
1851372
MDL number:
MFCD00001672

Key Documents

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InChI key

KEIFWROAQVVDBN-UHFFFAOYSA-N

InChI

1S/C10H10/c1-2-6-10-8-4-3-7-9(10)5-1/h1-3,5-7H,4,8H2

SMILES string

C1Cc2ccccc2C=C1

grade

analytical standard

shelf life

limited shelf life, expiry date on the label

technique(s)

HPLC: suitable, gas chromatography (GC): suitable

refractive index

n20/D 1.582 (lit.)

bp

89 °C/16 mmHg (lit.)

mp

−8 °C (lit.)

density

0.997 g/mL at 25 °C (lit.)

application(s)

environmental

format

neat

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General description

1,2-Dihydronaphthalene is a bicyclic hydrocarbon, which resembles naphthalene but shows partial unsaturation in one of its rings. Its derivatives find wide applications in natural compounds of therapeutic interest.

Application

1,2-Dihydronaphthalene may be used as an analytical standard for the determination of the analyte in polycyclic aromatic hydrocarbon (PAH) mixtures by gas chromatography technique.
Refer to the product′s Certificate of Analysis for more information on a suitable instrument technique. Contact Technical Service for further support.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

152.6 °F - closed cup

flash_point_c

67 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK0747
BCBZ5220

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Prediction of gas chromatographic retention indexes of polycyclic aromation compounds and nitrated polycyclic aromatic compounds
Rohrbaugh RH and Jurs PC
Analytical Chemistry, 58(6), 1210-1212 (1986)
Retention indices for programmed-temperature capillary-column gas chromatography of polycyclic aromatic hydrocarbons
Lee ML, et al.
Analytical Chemistry, 51(6), 768-773 (1979)
The synthesis of novel dihydronaphthalenes and benzofluorenes
Novel Selenium-Mediated Rearrangements and Cyclisations, 77(6), 1210-1212 (2012)
S L Eaton et al.
Applied and environmental microbiology, 62(12), 4388-4394 (1996-12-01)
The substrate oxidation profiles of Sphingomonas yanoikuyae B1 biphenyl-2,3-dioxygenase and cis-biphenyl dihydrodiol dehydrogenase activities were examined with 1,2-dihydronaphthalene and various cis-diols as substrates. m-Xylene-induced cells of strain B1 oxidized 1,2-dihydronaphthalene to (-)-(1R,2S)-cis-1,2-dihydroxy-1,2-3,4-tetrahydronaphthalene as the major product (73% relative yield). Small
D S Torok et al.
Journal of bacteriology, 177(20), 5799-5805 (1995-10-01)
Bacterial strains expressing toluene and naphthalene dioxygenase were used to examine the sequence of reactions involved in the oxidation of 1,2-dihydronaphthalene. Toluene dioxygenase of Pseudomonas putida F39/D oxidizes 1,2-dihydronaphthalene to (+)-cis-(1S,2R)-dihydroxy-1,2,3,4-tetrahydronaphthalene, (+)-(1R)-hydroxy-1,2-dihydronaphthalene, and (+)-cis-(1R,2S)-dihydroxy-1,2-dihydronaphthalene. In contrast, naphthalene dioxygenase of Pseudomonas
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