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380474

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
Pricing and availability is not currently available.

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

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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.
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
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
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
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    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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