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96-53-7 - 2-Mercaptothiazoline, 98+% - 2-Thiazolinethiol - L04924 - Alfa Aesar

L04924 2-Mercaptothiazoline, 98+%

CAS Number
96-53-7
Synonyms
2-Thiazolinethiol

Size Price ($) Quantity Availability
100g 28.71
500g 92.80
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2-Mercaptothiazoline, 98+%

MDL
MFCD00126013
EINECS
202-512-1

Chemical Properties

Formula
C3H5NS2
Formula Weight
119.21
Melting point
103-107°
Solubility
Soluble in chloroform, methanol. Slightly soluble in water.

Applications

2-Mercaptothiazoline, is used in the chain-lengthening of alkyl halides by trans-iodopropenylenation. 2-Mercaptothiazoline is an antithyroid agent that strongly reduces thyroid hormone levels. 2-Mercaptothiazoline is also used as an intermediate in the preparation of biologically active compounds. It is also used as a tool for highly selective chiral synthesis of penam- and carbapenam-type β-lactam antibiotics.

Notes

Keep container tightly closed in a dry and well-ventilated place. Keep away from oxidizing agents.

Literature References

Lei Tao et. al. Synthesis and bioactivity of poly(HPMA)-lysozyme conjugates: the use of novel thiazolidine-2-thione coupling chemistry. Organic & Biomolecular Chemistry. span>2009, 7,(17), 3481-3485 .

Newton L Dias Filho et. al. Preparation of a clay-modified carbon paste electrode based on 2-thiazoline-2-thiol-hexadecylammonium sorption for the sensitive determination of mercury. Analytical Sciences. span>2005, 21,(11), 1309-1316 .

Used in the chain-lengthening of alkyl halides by trans-iodopropenylenation: Org. Synth. Coll., 6, 704 (1988):

Reaction with ɑ-bromo esters gives the S-alkoxycarbonylmethyl derivatives, which can be C-alkylated by alkyl halides, using NaH as base. Sulfur-free products can be obtained by reduction (Zn/AcOH) to give the substituted acetic acid, or by reaction with iodidomethane to give the corresponding ɑ-iodo ester: Tetrahedron Lett., 2677 (1977).

GHS Hazard and Precautionary Statements

Hazard Statements: H301

Toxic if swallowed.

Precautionary Statements: P280f-P309-P310

Wear protective clothing. IF exposed or if you feel unwell: Immediately call a POISON CENTER or doctor/physician.

Other References

Beilstein
106332
Hazard Class
6.1
Packing Group
III
Harmonized Tariff Code
2934.10
TSCA
Yes
RTECS
XJ6122000

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