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Sigma-Aldrich

2-Hydroxyethyl disulfide

technical grade

Synonym(s):

2,2′-Dithiodiethanol, Bis(2-hydroxyethyl) disulfide

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About This Item

Linear Formula:
HOCH2CH2SSCH2CH2OH
CAS Number:
1892-29-1
Molecular Weight:
154.25
Beilstein:
1735851
EC Number:
217-576-6
MDL number:
MFCD00002906
UNSPSC Code:
12162002
PubChem Substance ID:
24863744
NACRES:
NA.23

grade

technical grade

Quality Level

200

form

liquid

refractive index

n20/D 1.57 (lit.)

bp

158-163 °C/3.5 mmHg (lit.)

mp

25-27 °C (lit.)

density

1.261 g/mL at 25 °C (lit.)

SMILES string

OCCSSCCO

InChI

1S/C4H10O2S2/c5-1-3-7-8-4-2-6/h5-6H,1-4H2

InChI key

KYNFOMQIXZUKRK-UHFFFAOYSA-N

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General description

2-Hydroxyethyldisulfide (HEDS) is an organosulfur compound ​that belongs to the class ofdialkyl disulfides and has a disulfide bond -S-S- between two hydroxyethylgroups. In material science, HEDS is used as a precursor to form self-assembledmonolayers (SAMs) on gold surfaces for applications such as corrosionprotection, lubrication, and sensors. In addition, 2-hydroxyethyl disulfide isalso used as a reducing agent in organic synthesis and as a crosslinking agentin the production of rubber compounds.

Application

2-Hydroxyethyl disulfide can be used as:
  • A chain extender in the preparation of waterborne self-healing polyurethane, which is used in leather coating.
  • As a precursor in the synthesis of multifunctional initiator, which is used in the preparation of star polystyrenes by atom transfer radical polymerization of styrene.
  • A starting material to prepare a disulfide-based branching agent. This branching agent is used to synthesize highly branched poly(2-hydroxypropyl methacrylate).

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Statements

H301,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

233.6 °F - closed cup

Flash Point(C)

112 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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P C Hiestand et al.
International journal of immunopharmacology, 7(1), 129-140 (1985-01-01)
HEDS (2-hydroxyethyl disulfide) and structurally related compounds were found to affect lymphocyte proliferation and functions in vitro. HEDS, and ADA 202-718 (ethylene-2-2'-bis(dithio)bis(ethanol], were shown to stimulate the proliferation of murine spleen cells. The growth of populations of murine T-cells (thymocytes)
J E Brotherton et al.
Physiological chemistry and physics, 12(6), 483-495 (1980-01-01)
Incubation of horse liver aldehyde dehydrogenase (aldehyde:NAD oxidoreductase, EC 1.2.1.3) with 2-hydroxyethyl disulfide formed mixed-disulfides between protein sulfhydryl groups and beta-mercaptoethanol. Reduction of aldehyde dehydrogenase activity may be associated with formation of one, or at most two, mixed-disulfides per dehydrogenase
Cristina Lamberti et al.
Electrophoresis, 28(10), 1633-1638 (2007-05-12)
Despite the large number of papers dealing with bacterial proteomes, very few include information about proteins with alkaline pI's, because of the limits inherent in 2-DE technology. Nonetheless, analyses of in silico proteomes of many prokaryotes show a bimodal distribution
Rakesh Kumar et al.
Biomacromolecules, 9(9), 2430-2437 (2008-08-01)
Biodegradable soy protein isolate (SPI), containing 2,2-diphenyl-2-hydroxyethanoic acid, films (SB) were successfully prepared with bis-(2-hydroxyethyl)sulfide as a plasticizer by compression molding at 155 degrees C and 15 MPa. By immersing the SB in distilled water for 26 h, we prepared
Nikola Mesecke et al.
Biochemistry, 47(5), 1452-1463 (2008-01-04)
Two novel monothiol glutaredoxins from yeast (ScGrx6 and ScGrx7) were identified and analyzed in vitro. Both proteins are highly suited to study structure-function relationships of glutaredoxin subclasses because they differ from all monothiol glutaredoxins investigated so far and share features
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