Skip to Content
Merck
All Photos(4)

Documents

I6256

Sigma-Aldrich

2-Iminothiolane hydrochloride

≥98% (TLC), powder

Synonym(s):

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

Sign Into View Organizational & Contract Pricing
All Photos(4)

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

Quality Level

200

Assay

≥98% (TLC)

form

powder

impurities

≤5% Free sulfhydryl groups

mp

198-201 °C (lit.)

solubility

H2O: 100 mg/mL

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

Looking for similar products? Visit Product Comparison Guide

General description

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

Application

2-Iminothiolane hydrochloride has been used in the synthesis of thiolated PEG (poly(ethylene glycol). It may be used to synthesize PLA-SH (polyethylene glycol-thiol) and PLA-PEG-SH (polyethylene glycol–polylactic acid-thiol).
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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
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:
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
View All Related Papers

Articles

Tailoring Collagen-Based Matrices for Regenerative Medicine and Tissue Engineering

Collagen molecules play a critical role in tissue architecture and strength, and in cell-matrix interactions as insoluble ligands to regulate the diverse phenotypic activities of cells.

Tailoring Collagen-Based Matrices for Regenerative Medicine and Tissue Engineering

Collagen molecules play a critical role in tissue architecture and strength, and in cell-matrix interactions as insoluble ligands to regulate the diverse phenotypic activities of cells.

Tailoring Collagen-Based Matrices for Regenerative Medicine and Tissue Engineering

Collagen molecules play a critical role in tissue architecture and strength, and in cell-matrix interactions as insoluble ligands to regulate the diverse phenotypic activities of cells.

Tailoring Collagen-Based Matrices for Regenerative Medicine and Tissue Engineering

Collagen molecules play a critical role in tissue architecture and strength, and in cell-matrix interactions as insoluble ligands to regulate the diverse phenotypic activities of cells.

See All

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service