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43761

Sigma-Aldrich

2,2′-Dithiodibenzoic acid

≥95.0% (NT)

Synonym(s):

2-Carboxyphenyl disulfide, Bis(2-carboxyphenyl) disulfide, Dithiosalicylic acid

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About This Item

Linear Formula:
S2(C6H4CO2H)2
CAS Number:
119-80-2
Molecular Weight:
306.36
Beilstein:
2221810
EC Number:
204-352-8
MDL number:
MFCD00002465
UNSPSC Code:
12352100
PubChem Substance ID:
57650191
NACRES:
NA.22

Quality Level

100

Assay

≥95.0% (NT)

ign. residue

≤3%

mp

287-290 °C (lit.)
288-293 °C

SMILES string

OC(=O)c1ccccc1SSc2ccccc2C(O)=O

InChI

1S/C14H10O4S2/c15-13(16)9-5-1-3-7-11(9)19-20-12-8-4-2-6-10(12)14(17)18/h1-8H,(H,15,16)(H,17,18)

InChI key

LBEMXJWGHIEXRA-UHFFFAOYSA-N

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General description

2,2′-Dithiodibenzoic acid is an sulfhydryl modifying reagent. 2,2′-Dithiodibenzoic acid on cocrystallization with imidazole or 4-methylimidazole affords bis(imidazolium) 2,2′-dithiodibenzoate and 4-methylimidazolium 2-[(2-carboxyphenyl)disulfanyl]benzoate organic salt, respectively. It also cocrystallizes with isonicotinohydrazide from methanol solution to afford the 1:2 cocrystal, 2,2′-dithiodibenzoic acid-isonicotinohydrazide.

Application

2,2′-Dithiodibenzoic acid may be used for the preparation of novel anionic heptadecanuclear silver(I) cluster, by the reaction with equivalent molar silver oxide under ultrasonic conditions at 50°C. It may be used for the preparation of polyamides containing a disulfide bond in their main chain.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Xiang-Gao Meng et al.
Acta crystallographica. Section C, Crystal structure communications, 64(Pt 5), o261-o263 (2008-05-03)
Cocrystallization of 2,2'-dithiodibenzoic acid with isonicotinohydrazide from methanol solution yields the 1:2 cocrystal 2,2'-dithiodibenzoic acid-isonicotinohydrazide (1/2), C(14)H(10)O(4)S(2) x 2 C(6)H(7)N(3)O. The component molecules are linked by intermolecular O-H...N, N-H...O, N-H...N and C-H...O hydrogen bonds into layers running parallel to the
New type polyamides containing disulfide bonds for positive active material of lithium secondary batteries.J. power
Tsutsumi H, et al.
Journal of Power Sources, 68(2), 735-738 (1997)
Di Sun et al.
Inorganic chemistry, 50(24), 12393-12395 (2011-11-11)
A novel anionic heptadecanuclear silver(I) cluster, (NH(4))(17)[(μ(6)-S)@Ag(17)(mba)(16)]·22H(2)O (1; H(2)mba = 2-mercaptobenzoic acid), was obtained by the reaction of equivalent molar silver oxide and 2,2'-dithiodibenzoic acid (H(2)dtba) under ultrasonic conditions at 50 °C. Complex 1 is a discrete cluster comprised of
J E Bodwell et al.
Biochemistry, 23(7), 1392-1398 (1984-03-27)
Glucocorticoid -receptor complexes from intact rat thymus cells incubated with [3H]dexamethasone at 0 degree C are in the nonactivated form and do not bind to DNA-cellulose. Upon being warmed, they are transformed to activated complexes that bind to DNA-cellulose at
Linheng Wei et al.
Acta crystallographica. Section C, Crystal structure communications, 65(Pt 9), o453-o456 (2009-09-04)
Cocrystallization of imidazole or 4-methylimidazole with 2,2'-dithiodibenzoic acid from methanol solution yields the title 2:1 and 1:1 organic salts, 2C(3)H(5)N(2)(+).C(14)H(10)O(4)S(2)(2-), (I), and C(4)H(7)N(2)(+).C(14)H(10)O(4)S(2)(-), (II), respectively. Compound (I) crystallizes in the monoclinic C2/c space group with the mid-point of the S-S
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