| Identification | More | [Name]
2-IMINOTHIOLANE | [CAS]
4781-83-3 | [Synonyms]
2-IMINOTHIOLANE
2-IMINOTHIOLANE HCL
2-IMINOTHIOLANE HYDROCHLORIDE
2-THIOLANIMINE HYDROCHLORIDE
DIHYDRO-2(3H)-THIOPHENIMINE HYDROCHLORIDE
METHYL 4-MERCAPTOBUTYRIMIDATE HYDROCHLORIDE
TRAUT'S REAGENT
Methyl-4-mercaptobutyrimidate hydrochloride 2-Iminothiolane hydrochloride
2(3H)-Thiophenimine, dihydro-, hydrochloride
2-Thiolanimine hydrochloride, 2IT, Dihydro-2(3H)-thiophenimine hydrochloride, Trauts reagent
2-Furancarboxyaldehyde, Reagent | [EINECS(EC#)]
800-330-2 | [Molecular Formula]
C4H7NS | [MDL Number]
MFCD00216010 | [Molecular Weight]
101.17 | [MOL File]
4781-83-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White Crystalline Solid | [Melting point ]
198-201 °C(lit.) | [storage temp. ]
2-8°C
| [solubility ]
H2O: 100 mg/mL
| [form ]
powder
| [Water Solubility ]
Freely soluble in water | [Usage]
A valuable tool in studies of cellular organelles and oligomeric enzymes, using the techniques of protein-protein cross-linking. It may also be used to introduce reactive sulfhydryl groups into proteins for subsequent reaction with alkylating agen | [BRN ]
3620079 | [CAS DataBase Reference]
4781-83-3(CAS DataBase Reference) |
| Safety Data | Back Directory | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [WGK Germany ]
3
| [F ]
1-3-10 | [HS Code ]
29349990 |
| Hazard Information | Back Directory | [Chemical Properties]
White Crystalline Solid | [Uses]
2-Iminothiolane hydrochloride is a valuable tool in studies of cellular organelles and oligomeric enzymes, using the techniques of protein-protein cross-linking. It may also be used to introduce reactive sulfhydryl groups into proteins for subsequent reaction with alkylating agents or heavy metal compounds.
| [Uses]
2-Iminothiolane hydrochloride is predominantly used as an amine reactive at pH 7-10 and is also an effective thiolation reagent for polysaccharides. It is also used as a RNA-protein crosslinking reagent as well as useful in cross-linking proteins.. | [Uses]
Cross-linking reagent cleavable by thiols. | [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. | [Purification Methods]
Recrystallise the hydrochloride from MeOH/Et2O (m 187-192o) or (MeOH/Me2CO), but after sublimation at ~180o/0.2mm the melting point rises to 202-203o. It has 1HNMR with 2.27 (2H, t), 3.25 (2H, t) and 3.52 (2H, t) in (CD3)2SO. [King et al. Biochemistry 17 1499 1978.] The free base is purifed by vacuum distillation (b 71-72o/6mm) with IR (film) with 1700 (C=N)cm-1 and 1HNMR (CDCl3) with at 3.58 (2H, t) and max 2.10-2.8 (4H, m). The free base is stable on storage but slowly hydrolyses in aqueous solutions with half-lives at 25o of 390hours at pH 9.1, 210hours at pH 10 and 18hours at pH 11. [Traut et al. Biochemistry 12 3266 1973, Biochemistry 17 399 1978, Alagon & King Biochemistry 19 4343 1980, Beilstein 17/9 V 12.] |
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