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I6256

2-Iminothiolane hydrochloride

≥98% (TLC), powder

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C4H7NS · HCl
CAS Number:
4781-83-3
Molecular Weight:
137.63
UNSPSC Code:
12352100
NACRES:
NA.21
PubChem Substance ID:
24896086
MDL number:
MFCD00039013
Beilstein/REAXYS Number:
3620079
Assay:
≥98% (TLC)
Form:
powder
Solubility:
H2O: 100 mg/mL
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Quality Level

200

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

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

signalword

Danger

hcodes

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class

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

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCL4349
SLCK8610
SLCK5080
SLCK4538
SLCJ8672

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Articles

Smart Oligonucleotide Delivery by Multifunctional Block Copolymers

Kanjiro Miyata (The University of Tokyo, Japan) provides insights on the rational design of polymeric materials for “smart” oligonucleotide delivery.

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.

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
Sitah Al Harthi et al.
Scientific reports, 9(1), 9563-9563 (2019-07-04)
This study aims to prepare, characterize and evaluate the pharmacokinetics of liposomal donepezil HCl (LDH) dispersed into thiolated chitosan hydrogel (TCH) in rabbits. Various hydrogels including TCH were prepared, and after characterization, TCH was selected for subsequent evaluations, due to
Methyl 4-mercaptobutyrimidate as a cleavable cross-linking reagent and its application to the Escherichia coli 30S ribosome.
R R Traut et al.
Biochemistry, 12(17), 3266-3273 (1973-08-14)
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Global Trade Item Number

SKUGTIN
I6256-100MG04061833857700
I6256-1G04061833857717
I6256-500MG04061833857724