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I6256

Sigma-Aldrich

2-Iminothiolane hydrochloride

≥98% (TLC), powder

Synonym(s):
2-Thiolanimine hydrochloride, 2IT, Dihydro-2(3H)-thiophenimine hydrochloride, Traut’s reagent
Empirical Formula (Hill Notation):
C4H7NS · HCl
CAS Number:
Molecular Weight:
137.63
Beilstein:
3620079
MDL number:
PubChem Substance ID:
NACRES:
NA.21

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

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Thioacetamide ACS reagent, ≥99.0%

Sigma-Aldrich

163678

Thioacetamide

assay

≥98% (TLC)

assay

98%

assay

≥99% (HPLC)

assay

≥99.0%

form

powder

form

liquid

form

powder

form

solid

impurities

≤5% Free sulfhydryl groups

impurities

-

impurities

-

impurities

-

mp

198-201 °C (lit.)

mp

108-112 °C (lit.)

mp

250 °C (dec.) (lit.)

mp

108-112 °C (lit.)

solubility

H2O: 100 mg/mL

solubility

-

solubility

H2O: 50 mg/mL, clear, colorless

solubility

passes test 2%

Quality Level

200

Quality Level

200

Quality Level

200

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

Signal Word

Danger

Hazard Statements

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

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