(S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE Chemical Properties

Melting point:

69-71 °C

Boiling point:

223.3±23.0 °C(Predicted)

Density 

1.17±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

almost transparency in Chloroform

form 

powder to crystal

pka

12.95±0.40(Predicted)

color 

White to Almost white

optical activity

[α]20/D -37±3°, c = 1 in chloroform

CAS DataBase Reference

76186-04-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2934100090

MSDS

• Language:English Provider:SigmaAldrich

(S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE Usage And Synthesis

Uses

(S)-4-Isopropylthiazolidine-2-thione may be used as a chiral auxiliary for the stereochemical induction at the phosphorus atom during the diastereoselective synthesis of aryloxy phosphoramidate prodrugs of 3μ-deoxy-2μ,3μ-didehydrothymidine monophosphate (d4TMP).', 'A highly selective and efficient chiral auxiliary which can be directly reduced to its corresponding aldehyde and the chiral auxiliary by reductive cleavage with diisobutylaluminum hydride.

Synthesis

The yields of the following procedures are higher than those reported in the literature (Erik Galvez, P. R., Felix Urp. (2009). Organic Synthesis, 86, 70). To a sealed tube was added aqueous KOH (2.7 g, 48.4 mmol, 5 eq., dissolved in 8 mL of water), 2 mL of ethanol, CS2 (2.9 mL, 48.4 mmol, 5 eq.) and (S)-(+)-2-amino-3-methyl-1-butanol (1.0 g, 9.69 mmol, 1 eq.). The reaction mixture was heated at 80 °C for 15 h, followed by purging with N2 to remove excess CS2. The reaction solution was neutralized with 1 M aqueous HCl and extracted with EtOAc (3 x 60 mL). The organic layers were combined, washed with brine (5 mL), dried over MgSO4 and concentrated in vacuum. The crude product was purified by silica gel column chromatography to afford (S)-4-isopropylthiazolidine-2-thione as a yellow solid (1.19 g, 76% yield). The characterization data of the product were in agreement with literature reports.

References

[1] European Journal of Organic Chemistry, 2011, # 23, p. 4397 - 4408
[2] Organic Syntheses, 2009, vol. 86, p. 70 - 80
[3] Tetrahedron, 2008, vol. 64, # 24, p. 5637 - 5644
[4] Organic Letters, 2011, vol. 13, # 21, p. 5916 - 5919
[5] European Journal of Organic Chemistry, 2009, # 33, p. 5841 - 5846

(S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE(76186-04-4)Related Product Information

• (R)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE
• (S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE