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Merck

380474

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
UNSPSC Code:
12162002
NACRES:
NA.23
PubChem Substance ID:
24863744
EC Number:
217-576-6
Beilstein/REAXYS Number:
1735851
MDL number:
MFCD00002906

Product Name

2-Hydroxyethyl disulfide, technical grade

InChI key

KYNFOMQIXZUKRK-UHFFFAOYSA-N

InChI

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

SMILES string

OCCSSCCO

grade

technical grade

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.)

Quality Level

200

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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).

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.

pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

signalword

Danger

hcodes

H301,H318

Hazard Classifications

Acute Tox. 3 Oral - Eye Dam. 1

Storage Class

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

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCK8369
BCCJ0399
BCCH5572
STBK4758
STBK2511

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D B Wetlaufer et al.
Protein engineering, 1(2), 141-146 (1987-02-01)
The rate and yield of oxidative renaturation of reduced RNase A has been studied as a function of [-S-S-]/[-SH]. The principal conclusion of these studies is that rates and yields of oxidative renaturation are strongly dependent on the low mol.
H Nakamura et al.
Free radical biology & medicine, 24(7-8), 1176-1186 (1998-06-17)
Thioredoxin (Trx) and glutaredoxin (Grx) are both multifunctional redox-active proteins. In this study, Grx was identified in human plasma by immunoaffinity purification. The affinity-purified material from human plasma displayed a band of 12 kDa identical to recombinant human Grx by
Nicolas Rouhier et al.
FEBS letters, 511(1-3), 145-149 (2002-02-01)
Six mutants (Y26A, C27S, Y29F, Y29P, C30S and Y26W/Y29P) have been engineered in order to explore the active site of poplar glutaredoxin (Grx) (Y26CPYC30). The cysteinic mutants indicate that Cys 27 is the primary nucleophile. Phe is a good substitute
A Goswami et al.
Endocrinology, 126(5), 2597-2606 (1990-05-01)
To study the physiological regulation of the iodothyronine 5'-deiodinases (I-5'D), we have examined the effects of some thiol blockers and of thyroid status on I-5'D activities both in vitro and in vivo. At low (less than 5 mM) concentrations of
Iraimoudi S Ayene et al.
The Journal of biological chemistry, 277(12), 9929-9935 (2002-01-15)
Glucose-6-phosphate dehydrogenase (G6PD), the rate-limiting enzyme of the oxidative pentose phosphate cycle, regulates the NADPH/NADP(+) ratio in eukaryotic cells. G6PD deficiency is one of the most common mutations in humans and is known to cause health problems for hundreds of
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