| Identification | More | [Name]
(S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE | [CAS]
76186-04-4 | [Synonyms]
(S)-4,5-DIHYDRO-4-ISOPROPYLTHIAZOLE-2-THIOL
(S)-(-)-4-ISOPROPYL-1,3-THIAZOLIDINE-2-THIONE
(S)-4-ISOPROPYL-1,3-THIAZOLIDINE-2-THIONE
(S)-4-ISOPROPYLTHIAZOLIDINE-2-THIONE
2-Thiazolidinethione,4-(1-methylethyl)-,(4S)-(9CI) | [Molecular Formula]
C6H11NS2 | [MDL Number]
MFCD03844797 | [Molecular Weight]
161.29 | [MOL File]
76186-04-4.mol |
| Chemical Properties | Back Directory | [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 Rotation]
[α]20/D -37±3°, c = 1 in chloroform | [InChI]
1S/C6H11NS2/c1-4(2)5-3-9-6(8)7-5/h4-5H,3H2,1-2H3,(H,7,8)/t5-/m1/s1 | [InChIKey]
CWIZUGZKLJDJLE-RXMQYKEDSA-N | [SMILES]
CC(C)[C@H]1CSC(=S)N1 | [CAS DataBase Reference]
76186-04-4(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [HS Code ]
2934100090 | [Storage Class]
11 - Combustible Solids |
| Hazard Information | Back Directory | [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 |
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| Company Name: |
Energy Chemical
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021-021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
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