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Merck
CN

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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InChI

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

SMILES string

N=C1SCCC1.Cl

InChI key

ATGUDZODTABURZ-UHFFFAOYSA-N

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

Quality Level

200

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
0000519402
0000519402
0000497262
0000497261
0000497260

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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:
Preparation of bioconjugates of CdTe nanocrystals for cancer marker detection.
Hu F, et al.
Nanotechnology, 17(12), 2972-2972 (2006)
Yu Su et al.
Frontiers in pharmacology, 11, 1165-1165 (2020-08-28)
Effective treatments for neurodegenerative diseases need to be developed. MiR132 is abundantly expressed in the brain, and it modulates neuron morphology and plays a key role in maintaining neuron survival. Regulating miR132 can effectively improve the symptoms of Alzheimer's disease.
Multifunctional micelles for cancer cell targeting, distribution imaging, and anticancer drug delivery.
Huang CK, et al.
Advances in Functional Materials, 17(14), 2291-2297 (2007)
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
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Product Information Sheet - I6256

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