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2-Iminothiolane hydrochloride

Name: 2-Iminothiolane hydrochloride
Brand: SIGMA

≥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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Properties

Quality Segment

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

Description

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

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.

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).

Other Notes

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

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This Item	D0632	D9779	D8130
Sigma-Aldrich I6256 2-Iminothiolane hydrochloride	Sigma-Aldrich D0632 DL-Dithiothreitol	Sigma-Aldrich D9779 DL-Dithiothreitol	Sigma-Aldrich D8130 5,5′-Dithiobis(2-nitrobenzoic acid)
description ≥98% (TLC), powder	description ≥98% (HPLC), ≥99.0% (titration)	description Molecular Biology, ≥98% (HPLC), ≥99% (titration)	description ≥98%, BioReagent, suitable for determination of sulfhydryl groups
form powder	form powder	form powder	form powder
solubility H₂O: 100 mg/mL	solubility H₂O: soluble 50 mg/mL, clear, colorless to very faintly yellow	solubility H₂O: 50 mg/mL	solubility -
assay ≥98% (TLC)	assay ≥98% (HPLC), ≥99.0% (titration)	assay ≥98% (HPLC), ≥99% (titration)	assay ≥98%
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
impurities ≤5% Free sulfhydryl groups	impurities -	impurities -	impurities -
mp 198-201 °C (lit.)	mp 41-44 °C (lit.)	mp 41-44 °C (lit.)	mp 240-245 °C (dec.) (lit.)

pictograms

GHS06

signalword

Danger

hcodes

H301

pcodes

P264 - P270 - P301 + P310 - P405 - P501

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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