282537

Sigma-Aldrich

1,8-Dimethylnaphthalene

95%

Linear Formula:
C10H6(CH3)2
CAS Number:
Molecular Weight:
156.22
Beilstein/REAXYS Number:
2039841
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

95%

bp

270 °C (lit.)

mp

59-61 °C (lit.)

SMILES string

Cc1cccc2cccc(C)c12

InChI

1S/C12H12/c1-9-5-3-7-11-8-4-6-10(2)12(9)11/h3-8H,1-2H3

InChI key

XAABPYINPXYOLM-UHFFFAOYSA-N

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General description

Mechanism of NO(2)(+) nitration of 1,8-dimethylnaphthalene has beeen investigated. Photolysis of the 1,8-dimethylnaphthalene/tetranitromethane charge-transfer complex affords the triad of 1,8-dimethylnaphthalene radical cation, nitrogen dioxide and trinitromethanide ion.

Application

1,8-Dimethylnaphthalene has been used in the preparation of 1,4-endoperoxides via dyesensitized photo-oxygenation reaction.

Packaging

1 g in glass bottle

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Tanaka et al.
The Journal of organic chemistry, 65(10), 2972-2978 (2000-05-18)
The nitration of methylnaphthalenes with NO(2)BF(4) and NOBF(4) was examined in order to shed light on the controversial aromatic nitration mechanism, electrophilic vs charge-transfer process. The NO(2)(+) nitration of 1,8-dimethylnaphthalene showed a drastic regioselectivity change depending on the reaction temperature...
Photochemical Nitration by Tetranitromethane. XVI. The Regiochemistry of Adduct Formation in the Photochemical Reaction of 1, 8-Dimethylnaphthalene and Tetranitromethane; Thermal 1, 3-Dipolar Nitro Addition Reactions.
Calvert Jl, et al.
Australian Journal of Chemistry, 47(7), 1211-1222 (1994)
Formation of 1, 4-endoperoxides from the dye-sensitized photo-oxygenation of alkyl-naphthalenes.
Wasserman HH and Larsen DL.
Journal of the Chemical Society. Chemical Communications, 5, 253-254 (1972)
Nien-Hsin Kao et al.
Marine pollution bulletin, 97(1-2), 319-332 (2015-06-08)
Three fishing harbors were investigated to study the polycyclic aromatic hydrocarbons in the sediments and trace possible anthropogenic sources by identification of cyclic terpenoid biomarkers. Seventeen terpanes, 10 steranes and 10 bicyclic sesquiterpanes in the marine diesel and the three...

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