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Merck
CN

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

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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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Florian Weiland et al.
Frontiers in oncology, 10, 1767-1767 (2020-10-27)
Ovarian cancer is the most lethal gynecologic malignancy. Early detection would improve survival, but an effective diagnostic test does not exist. Novel biomarkers for early ovarian cancer diagnosis are therefore warranted. We performed intraoperative blood sampling from ovarian veins of
I S Ayene et al.
International journal of radiation biology, 76(11), 1523-1531 (2000-12-01)
We investigated the effect of protein- and non protein-thiol oxidation on DNA double-strand-break (DSB) rejoining after irradiation and its relevance in the survival of CHO cells. We used mutant cells null for glucose 6 phosphate dehydrogenase (G6PD) activity since reducing
Mary A Robinson et al.
Free radical biology & medicine, 48(2), 189-195 (2009-10-14)
Stimulated macrophages produce nitric oxide (NO) via inducible nitric oxide synthase (iNOS) using molecular O(2), L-arginine, and NADPH. Exposure of macrophages to hypoxia decreases NO production within seconds, suggesting substrate limitation as the mechanism. Conflicting data exist regarding the effect
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
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
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