(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE

(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE Property

Melting point:

93-94℃

Boiling point:

328.4±25.0 °C(Predicted)

Density 

1.27±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

pka

13.01±0.40(Predicted)

color 

Off-white

optical activity

[α]20/D -122±5°, c = 1% in chloroform

CAS DataBase Reference

171877-39-7(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36

WGK Germany 

3

F 

10-23

Hazard Note 

Irritant

HS Code 

29341000

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H300Fatal if swallowed

H312Harmful in contact with skin

H315Causes skin irritation

H317May cause an allergic skin reaction

H341Suspected of causing genetic defects

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P272Contaminated work clothing should not be allowed out of the workplace.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P391Collect spillage. Hazardous to the aquatic environment

P405Store locked up.

P501Dispose of contents/container to..…

(S)-4-BENZYL-1,3-THIAZOLIDINE-2-THIONE Chemical Properties,Usage,Production

Chemical Properties

Off-white crystalline

Uses

Evans-Type Oxazolidinethione And Thiazolidinethione Auxiliaries

Synthesis

The general procedure for the synthesis of S-4-benzylthiazolidine-2-thione from the compound (CAS: 131744-19-9) is as follows: the crude oxazolidinethione was dissolved in carbon disulfide (CS2, 364.0 mL, 5.95 mol), followed by the addition of 1N aqueous potassium hydroxide (KOH) solution (5.95 L). The reaction mixture was heated to 100 °C and stirred at this temperature for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and extracted with dichloromethane (CH2Cl2, 3 x 3 L). The organic layers were combined, dried with anhydrous sodium sulfate (Na2SO4), filtered and rinsed through a silica gel plug (800 g) with a 1:1 solvent mixture of hexane/ethyl acetate (EtOAc, 2 L). Subsequently, the crude product was concentrated by rotary evaporation. The crude product was further purified by fast chromatography using a gradient elution from hexane to 1:1 hexane/ethyl acetate to give S-4-benzylthiazoline-2-thione (S2, 201.5 g, 81% yield). Supporting information S2: Thin-layer chromatography (TLC, 1:1 hexane/EtOAc): Rf = 0.31; 1H NMR (CDCl3, 500 MHz) δ 8.36 (broad single peak, 1H), 7.32 (multiple peaks, 2H), 7.26 (multiple peaks, 1H), 7.18 (multiple peaks, 2H), 4.46 (double double peaks, J = 7.5, 15.0 Hz, 1H), 3.50 (double triple peak, J = 7.9, 11.5 Hz, 1H), 3.25 (double triple peak, J = 7.2, 11.5 Hz, 1H), 3.04 (multiple peaks, 1H), 2.93 (multiple peaks, 1H); 13C NMR (CDCl3, 125 MHz) δ 200.5, 135.7, 129.0, 128.9, 127.2, 65.1, 39.7, 37.8; Fourier Transform Infrared Spectroscopy (FTIR, thin film) vmax 3154, 1602, 1495, 1437, 1327, 1297, 1279, 1233, 1204, 1040, 1008, 957, 743 cm-1; High Resolution Electrospray Ionization Mass Spectrometry (HR- ESI-MS) m/z calculated value for C10H11NS2 [M]+: 209.0333, measured value 209.0342.

References

[1] Organic Letters, 2012, vol. 14, # 21, p. 5396 - 5399
[2] Patent: WO2013/148324, 2013, A1. Location in patent: Paragraph 0158-0159
[3] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6604 - 6607
[4] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 14, p. 2139 - 2145