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The
Comparative Reaction Solvent Research
at Gaylord Chemical Company,
L.L.C. systematically compares DMSO performance versus other common solvents
in commercially important reactions. Using established references from the chemi-
cal literature, our scientists test reaction systems to ascertain the yield, selectivity,
and reaction rates of DMSO versus other solvents.
Nucleophilic Aromatic Substitution (S
N
Ar)
reactions are essential tools for the
synthesis of many pharmaceutical targets (quinolone antibiotics) and agricultural
products (dinitrophenyl ether herbicides). Addition-elimination reactions of this type
benefit from the use of dipolar aprotic solvents, and DMSO has been shown to excel
as a reaction solvent in these applications.
Gaylord Chemical Company's
Comparative Reaction Solvent Research
Examines Nucleophilic Aromatic Substitution
Gaylord Chemical Company,
L.L.C. (GCC) is the world's
leading provider of Dimethyl
Sulfoxide (DMSO) solutions.
Beginning in the early
1960's ,GCC has been dedi-
cated to the development of
new uses for DMSO. In or-
der to meet customer-specific
needs, GCC has pioneered
the development of multiple
grades of DMSO, including
DMSO USP.

Gaylord Chemical's solutions
-based approach has contrib-
uted to the development and
growth of industries including
pharmaceuticals, hydro-
carbons, electronics, poly-
mers, coatings, agricultural
chemicals, and industrial
cleaners.

Gaylord Chemical's head-
quarters are located in Slidell,
Louisiana with manufactur-
ing, research, and develop-
ment facilities in nearby
Bogalusa, Louisiana. GCC
remains the only producer of
DMSO in the Western Hemi-
sphere.
D M S O
DMSO PRODUCT INFORMATION BULLETIN
dimethyl sulfoxide
and the S
N
Ar reaction
NO
2
Cl
O
2
N
NH
2
O
NH
2
HO
solvent
0
10
20
30
40
50
60
70
80
90
100
0
50
100
150
200
time (min)
y
i
e
l
d

(
%
)
DMSO
NMP
DMF
An unusual degree of
selectivity
was seen in the reaction shown.
Excellent yield
of
the diphenyl ether product was obtained, even when a bifunctional nucleophile was
employed.
NMP and DMF produced product mixtures containing the corresponding diphenyl-
amine as a significant impurity.
Bulletin 153B
Oct 2007
Gaylord Chemical Company, L.L.C.
Your Global Leader For DMSO Solutions!
P.O. Box 1209
Slidell, LA 70459-1209 USA
1.800.426.6620 Office
1.985.649.0068 Fax
info@gaylordchemical.com