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I6256

Sigma-Aldrich

2-Iminothiolane hydrochloride

≥98% (TLC), powder

Synonym(s):

2-Thiolanimine hydrochloride, 2IT, Dihydro-2(3H)-thiophenimine hydrochloride, Traut’s reagent

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100 MG
€101.00
500 MG
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1 G
€522.00

About This Item

Empirical Formula (Hill Notation):
C4H7NS · HCl
CAS Number:
4781-83-3
Molecular Weight:
137.63
Beilstein:
3620079
MDL number:
MFCD00039013
UNSPSC Code:
12352100
PubChem Substance ID:
24896086
NACRES:
NA.21
grade:
for analytical purposes
form:
powder
solubility:
H2O: 100 mg/mL

€101.00

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grade

for analytical purposes

Assay

≥98% (TLC)

form

powder

impurities

≤5% Free sulfhydryl groups

mp

198-201 °C (lit.)

solubility

H2O: 100 mg/mL

functional group

thioether

storage temp.

2-8°C

SMILES string

N=C1SCCC1.Cl

InChI

1S/C4H7NS.ClH/c5-4-2-1-3-6-4;/h5H,1-3H2;1H

InChI key

ATGUDZODTABURZ-UHFFFAOYSA-N

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General description

2-Iminothiolane hydrochloride (2-IT.HCl), a protein modification reagent,[1] is commonly employed to attach thiol groups to proteins and peptides.[2] Raman spectroscopic analysis of hair keratin fibers modified with 2-IT.HCl showed the formation of new disulfide groups.[3]

Application

2-Iminothiolane hydrochloride has been used in the synthesis of thiolated PEG (poly(ethylene glycol).[4] It may be used to synthesize PLA-SH (polyethylene glycol-thiol) and PLA-PEG-SH (polyethylene glycol–polylactic acid-thiol).[5]
Thiolating reagent for primary amines. Reacts at pH 7-10 by amidine bond to present free sulfhydryl. Useful in preparation of disulfide and/or thioether linked conjugates.

Other Notes

Note that the amidine linkage preserves original primary amine positive charge. Incorporates a five atom linker.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000427626
0000427625
0000420185
0000417935
0000417934

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Hafizah Mahmud et al.
International journal of molecular sciences, 19(3) (2018-03-03)
We recently have established a successful xenograft model of human glioblastoma cells by enriching hyaluronic acid-dependent spheroid-forming populations termed U251MG-P1 cells from U251MG cells. Since U251MG-P1 cells have been confirmed to express CD44 along with principal stemness marker genes, OCT3/4
Alexander Ewe et al.
Nanomedicine : nanotechnology, biology, and medicine, 13(1), 209-218 (2016-08-25)
Therapeutic applications of RNA interference (RNAi) require efficient siRNA delivery strategies in vivo. Combining lipid-based carriers with polymeric nanoparticles offers the favorable properties of both systems. This is the first study to explore polyethylenimine-based lipopolyplexes comprising a low-molecular weight PEI
Akio Kuzuhara
Biopolymers, 79(4), 173-184 (2005-09-08)
For the purpose of investigating in detail the influence of chemical modification using 2-iminothiolane hydrochloride (2-IT) on keratin fibers, the structure of cross-sections at various depths of white human hair, treated with 2-IT and then oxidized, was directly analyzed without
Doyeon Kim et al.
Nano convergence, 7(1), 30-30 (2020-09-09)
One of the major obstacles to successful chemotherapy is multi-drug resistance (MDR). A multi-drug resistant cancerous cell abnormally overexpresses membrane transporters that pump anticancer drugs out of the cell, resulting in low anticancer drug delivery efficiency. To overcome the limitation
Hohyeon Lee et al.
Theranostics, 8(15), 4247-4261 (2018-08-22)
Metastasis is the leading cause of cancer-related deaths. A number of chemotherapeutic and early diagnosis strategies, including nanomedicine, have been developed to target metastatic tumor cells. However, simultaneous inhibition and imaging of metastasis is yet to be fully achieved. Methods:
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  1. How can I determine the shelf life / expiration / retest date of this product?

    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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