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282537

1,8-Dimethylnaphthalene

95%

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About This Item

Linear Formula:
C10H6(CH3)2
CAS Number:
569-41-5
Molecular Weight:
156.22
EC Number:
209-314-4
UNSPSC Code:
12352100
PubChem Substance ID:
24857052
Beilstein/REAXYS Number:
2039841
MDL number:
MFCD00004040
Assay:
95%
Form:
solid
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assay

95%

form

solid

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

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
09712HJ
04308DT
13930PX
08211TO
05114AC

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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)
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Global Trade Item Number

SKUGTIN
282537-1G04061826228333