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Thiazolidine

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Name

Thiazolidine

EINECS 208-002-5
CAS No. 504-78-9 Density 1.058 g/cm3
PSA 37.33000 LogP 0.60910
Solubility N/A Melting Point N/A
Formula C3H7NS Boiling Point 164.5 °C at 760 mmHg
Molecular Weight 89.1613 Flash Point 56.1 °C
Transport Information UN 1993 3/PG 3 Appearance clear colorless liquid
Safety 45-36/37/39-26 Risk Codes 34
Molecular Structure Molecular Structure of 504-78-9 (Thiazolidine) Hazard Symbols CorrosiveC
Synonyms

Thiazolidine

Article Data 30

Thiazolidine Synthetic route

50-00-0

formaldehyd

156-57-0

2-mercaptoethylamine hydrochloride

504-78-9

1,3-thiazolidine

50-00-0

formaldehyd

60-23-1

Cysteamine

504-78-9

1,3-thiazolidine

Conditions
ConditionsYield
With phosphate buffer In water at 25℃; for 0.5h;
50-00-0

formaldehyd

60-23-1

Cysteamine

A

504-78-9

1,3-thiazolidine

B

504-79-0

4,5-dihydro-thiazole

Conditions
ConditionsYield
With phosphate buffer at 25℃; for 0.5h; Mechanism; var. buffer systems; var. aldehydes; also in the presence of ethanol;
504-78-9

1,3-thiazolidine

24424-99-5

di-tert-butyl dicarbonate

148312-55-4

tert-butyl thiazolidine-3-carboxylate

Conditions
ConditionsYield
In tetrahydrofuran; water at 20℃; for 20h;100%
In tetrahydrofuran; water at 20℃; for 20h; Schlenk technique;99%
With dmap In acetonitrile for 3h; Ambient temperature;89%
In 1,4-dioxane; water86.2%
504-78-9

1,3-thiazolidine

6601-22-5

2,6-Dichloro-4-morpholino-1,3,5-triazine

2-chloro-4-morpholino-6-(3-thiazolidinyl)-1,3,5-triazine

Conditions
ConditionsYield
With potassium carbonate In water; N,N-dimethyl-formamide a) -5 deg C, 2 h, b) RT, 20 h;97%
With potassium carbonate In hexane; ethyl acetate; N,N-dimethyl-formamide97.2%
504-78-9

1,3-thiazolidine

841302-34-9

(S)-[1-(3-hydroxyadamantan-1-yl)-2-oxo-2-pyrrolidin-1-ylethyl]-carbamic acid tert-butyl ester

841302-35-0

(S)-[1-(3-hydroxyadamantan-1-yl)-2-oxo-2-thiazolidin-3-ylethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In DMF (N,N-dimethyl-formamide) at 0℃; for 22h;95.7%
504-78-9

1,3-thiazolidine

98-88-4

benzoyl chloride

941599-07-1

N-benzoyl-1,3-thiazolidine

Conditions
ConditionsYield
In dichloromethane at 0℃; for 0.75h;95%
504-78-9

1,3-thiazolidine

143815-60-5

2-chloro-5-cyano-6-ethoxy-4-phenylpyridine-3-carboxaldehyde

143815-68-3

2-Ethoxy-5-formyl-4-phenyl-6-thiazolidin-3-yl-nicotinonitrile

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 0.166667h; Heating;93%
504-78-9

1,3-thiazolidine

76-05-1

trifluoroacetic acid

N-Boc pyroglutamic acid-Wang resin

N-Boc pyroglutamic acid-Wang resin

(S)-2-Amino-5-oxo-5-thiazolidin-3-yl-pentanoic acid; compound with trifluoro-acetic acid

Conditions
ConditionsYield
Stage #1: 1,3-thiazolidine; N-Boc pyroglutamic acid-Wang resin In tetrahydrofuran Addition;
Stage #2: trifluoroacetic acid In water for 2.5h; Hydrolysis;
93%
504-78-9

1,3-thiazolidine

336870-02-1

(S)-tert-butoxycarbonylamino-(trans-4-hydroxy-cyclohexyl)-acetic acid

(S)-[1-(4-hydroxy-cyclohexyl)-2-oxo-2-thiazolidin-3-yl-ethyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: (S)-tert-butoxycarbonylamino-(trans-4-hydroxy-cyclohexyl)-acetic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In Isopropyl acetate at 0℃; for 2h;
Stage #2: 1,3-thiazolidine In Isopropyl acetate at 0 - 20℃; for 18h;
93%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran at 20℃; for 12h;

Thiazolidine Specification

The Thiazolidine, with the CAS registry number 504-78-9 and EINECS registry number 208-002-5, has the systematic name and IUPAC name of 1,3-thiazolidine. It is a kind of clear colorless liquid, and belongs to the following product categories: Heterocyclic Compounds; Building Blocks; Heterocyclic Building Blocks; Thiazolines/Thiazolidines. And the molecular formula of the chemical is C3H7NS.

The characteristics of Thiazolidine are as followings: (1)ACD/LogP: -0.12; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -3.03; (4)ACD/LogD (pH 7.4): -1.57; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 1; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 28.54 Å2; (13)Index of Refraction: 1.513; (14)Molar Refractivity: 25.34 cm3; (15)Molar Volume: 84.2 cm3; (16)Polarizability: 10.04×10-24cm3; (17)Surface Tension: 37.5 dyne/cm; (18)Density: 1.058 g/cm3; (19)Flash Point: 56.1 °C; (20)Enthalpy of Vaporization: 40.1 kJ/mol; (21)Boiling Point: 164.5 °C at 760 mmHg; (22)Vapour Pressure: 1.96 mmHg at 25°C. 

It may be synthesized by a condensation reaction between a thiol and an aldehyde or ketone. The reaction is reversible. Therefore,many thiazolidines are labile towards hydrolysis in aqueous solution. Hydrolysis of the thiazolidine generates the thiol and aldehyde or ketone from which it was synthesized.

Uses of Thiazolidine: It can react with 4-cyano-benzenediazonium; tetrafluoroborate to produce 3-(p-cyanophenylazo)-1,3-thiazolidine. This reaction will need the menstruum acetone and H2O. The reaction time is 0.5 hours with temperature of 0°C, and the yield is about 37%.

You should be cautious while dealing with this chemical. It may cause burns. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: S1CCNC1
(2)InChI: InChI=1/C3H7NS/c1-2-5-3-4-1/h4H,1-3H2
(3)InChIKey: OGYGFUAIIOPWQD-UHFFFAOYAA

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 800mg/kg (800mg/kg)   Farmaco, Edizione Scientifica. Vol. 36, Pg. 740, 1981.

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