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I6256 Sigma-Aldrich

2-Iminothiolane hydrochloride

≥98% (TLC), powder

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

  • CAS Number 4781-83-3

  • Empirical Formula (Hill Notation) C4H7NS · HCl

  • Molecular Weight 137.63

  •  Beilstein/REAXYS Number 3620079

  •  MDL number MFCD00039013

  •  PubChem Substance ID 24896086

  •  NACRES NA.21

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Properties

Related Categories Molecular Biology, Protein Modification, Protein Structural Analysis, Proteomics, Reagents for lysine modification,
Quality Level   200
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

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

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.

Packaging

1 g in glass bottle

100, 500 mg in glass bottle

Other Notes

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

Safety & Documentation

Safety Information

Symbol 
GHS06  GHS06
Signal word 
Danger
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Smart Oligonucleotide Delivery by Multifunctional Block Copolymers

1Innovation Center of NanoMedicine, Kawasaki Institute of Industrial Promotion, Tonomachi, Kawasaki-ku, Kawasaki, Japan. 2Department of Materials Engineering, Graduate School of Engineering, The Univ...
Keywords: Adsorption, Aminations, Antitumor agents, Bacterial conjugations, Biochemistry, Cancer, Cell culture, Click chemistry, Clinical, Degradations, Gene expression, Ligands, Oxidations, Polymerization reactions, Reductions, Ring-opening polymerization

Tailoring Collagen-Based Matrices for Regenerative Medicine and Tissue Engineering

Jiayu Leong,1 Liam Grover,2 Hyunjoon Kong1* 1Department of Chemical and Biomolecular Engineering University of Illinois, Urbana-Champaign, IL 61801 USA 2University of Birmingham, UK *Email: hjkong06@...
Keywords: Adhesion, Adsorption, Aminations, Bacterial conjugations, Biomaterials, Building blocks, Cell culture, Clinical, Deaminations, Degradations, Deposition, Diffusion, Growth factors, Hydroxylations, Immobilization, Ligands, Methylations, Michael reaction, PAGE, Purification, Recombination, Reductive aminations, Transfection

Peer-Reviewed Papers
15

References

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