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:
Molecular Weight:
137.63
UNSPSC Code:
12352100
NACRES:
NA.21
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
3620079
Assay:
≥98% (TLC)
Form:
powder
Solubility:
H2O: 100 mg/mL
Quality Level
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
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.
signalword
Danger
hcodes
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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