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Sigma-Aldrich

2,2′-Dithiodibenzoic acid

≥95.0% (NT)

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Synonym(s):
2-Carboxyphenyl disulfide, Bis(2-carboxyphenyl) disulfide, Dithiosalicylic acid
Linear Formula:
S2(C6H4CO2H)2
CAS Number:
Molecular Weight:
306.36
Beilstein/REAXYS Number:
2221810
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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
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
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Journal of Power Sources, 68(2), 735-738 (1997)
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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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