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Rhodanine
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Name

Rhodanine

 EINECS 205-505-1
CAS No. 141-84-4 Density 1.59 g/cm3
PSA 86.49000 LogP 0.46310
Solubility soluble in hot water Melting Point 165-169 °C(lit.)
Formula C3H3NOS2 Boiling Point 218.2 °C at 760 mmHg
Molecular Weight 133.195 Flash Point 85.7 °C
Transport Information UN 3288 Appearance light yellow to beige fine crystalline powder
Safety 22-26-39 Risk Codes 22-41
Molecular Structure Molecular Structure of 141-84-4 (Rhodanine) Hazard Symbols HarmfulXn
Synonyms

4-Oxo-2-thionothiazolidine;4-Oxo-2-thioxothiazolidine;4-Thiazolidinone-2-thione;NSC 1899;Rhodaninicacid;Rhodanine(6CI,8CI);2-Thio-4-ketothiazolidine;2-Thioxo-1,3-thiazolidin-4-one;2-Thioxo-4-thiazolidinone;4-Oxo-1,3-thiazolidine-2-thione;4-Oxo-2-thiazolidinethione;

Article Data 33

Rhodanine Synthetic route

75-15-0

carbon disulfide

3926-62-3

sodium monochloroacetic acid

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
Stage #1: carbon disulfide With ammonium hydroxide In water at 40℃; for 0.5h;
Stage #2: sodium monochloroacetic acid In water for 0.416667 - 0.583333h;
Stage #3: With hydrogenchloride In water at 100 - 110℃;		94%
Stage #1: carbon disulfide With ammonia
Stage #2: sodium monochloroacetic acid at 80℃;
5718-83-2

rhodanine 3-acetic acid

78-84-2

isobutyraldehyde

A

141-84-4

2-thioxo-4-thiazolidinone

B

3-carboxymethyl-5-2,2-dimethylpropylidene

3-carboxymethyl-5-2,2-dimethylpropylidene

Conditions
ConditionsYield
With hydrogenchloride; sodium acetate; acetic acid In N,N-dimethyl-formamideA 83%
B n/a
68-11-1

mercaptoacetic acid

17356-08-0

thiourea

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
With hydrogenchloride In toluene at 110℃; for 8h; Catalytic behavior; Solvent; Reagent/catalyst; Temperature;77%
With sulfuric acid In toluene at 80℃; for 20h; Temperature;

C3H4NO2S2(1-)*Na(1+)

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
With hydrogenchloride In water at 90 - 95℃;70%
513-74-6

ammonium dithiocarbamate

79-04-9

chloroacetyl chloride

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
With triethylamine In water; acetone for 0.5h;68%
With triethylamine In water; acetone for 0.5h; Product distribution; Mechanism; Ambient temperature; other N-substituted dithiocarbamates investigated;68%

ammonium thiocyanate

79-11-8

chloroacetic acid

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
In water for 0.333333h; Reflux;45%
14064-10-9

diethyl 2-chloromalonate

513-74-6

ammonium dithiocarbamate

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
With water
1438-16-0

3-aminorhodanine

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
With hydrogenchloride; sodium nitrite
463-56-9

thiocyanic acid

4438-95-3

thiocyanato-acetic acid

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
With diethyl ether
29596-83-6

(thiocarbamoylthio)acetic acid

141-84-4

2-thioxo-4-thiazolidinone

Conditions
ConditionsYield
beim Erhitzen auf den Schmelzpunkt;
With water
With acid

Rhodanine Chemical Properties

Molecular Formula: C3H3NOS2
Molar Mass: 133.19 g/mol
EINECS: 205-505-1
Density: 1.59 g/cm3
Flash Point: 85.7 °C
Index of Refraction: 1.711
Boiling Point: 218.2 °C at 760 mmHg
Vapour Pressure: 0.128 mmHg at 25 °C
Melting Point: 165-169 °C(lit.)
Water Solubility: soluble
Appearance: light yellow to beige fine crystalline powder
Product categories of Rhodanine (141-84-4): Miscellaneous;Thiazoles, Isothiazoles & Benzothiazoles
Structure of Rhodanine (CAS NO.141-84-4):

XLogP3-AA: 0.7
H-Bond Donor: 1
H-Bond Acceptor: 1
Systematic Name: 2-Thioxothiazolidin-4-one 
SMILES: O=C1NC(=S)SC1 
InChI: InChI=1/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) 
InChIKey: KIWUVOGUEXMXSV-UHFFFAOYAP 
Std. InChI: InChI=1S/C3H3NOS2/c5-2-1-7-3(6)4-2/h1H2,(H,4,5,6) 
Std. InChIKey: KIWUVOGUEXMXSV-UHFFFAOYSA-N

Rhodanine Toxicity Data With Reference

1.    

skn-rbt 500 mg/24H MOD

     28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,202.
2.    

eye-rbt 750 µg/24H SEV

     28ZPAK    Sbornik Vysledku Toxixologickeho Vysetreni Latek A Pripravku Marhold, J.V.,Institut Pro Vychovu Vedoucicn Pracovniku Chemickeho Prumyclu Praha,Czechoslovakia.: 1972,202.
3.    

orl-rat LD50:320 mg/kg

     85JCAE    Prehled Prumyslove Toxikologie; Organicke Latky Marhold, J.,Prague, Czechoslovakia.: Avicenum,1986,1093.
4.    

orl-mus LD50:225 mg/kg

     FRZKAP    Farmatsevtichnii Zhurnal (Kiev). 17 (1)(1962),36.
5.    

ipr-mus LD50:200 mg/kg

     NTIS**    National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .
6.    

scu-mus LDLo:200 mg/kg

     AIPTAK    Archives Internationales de Pharmacodynamie et de Therapie. 12 (1904),447.
7.    

ivn-mus LD50:32 mg/kg

     CSLNX*    U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. (Aberdeen Proving Ground, MD 21010) NX#04798 .

Rhodanine Consensus Reports

Reported in EPA TSCA Inventory.

Rhodanine Safety Profile

Hazard Codes: HarmfulXn
Risk Statements: 22-41 
R22:Harmful if swallowed. 
R41:Risk of serious damage to the eyes.
Safety Statements: 22-26-39 
S22:Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S39:Wear eye / face protection.
RIDADR: 3288
WGK Germany: 3
RTECS: VI7700000
HazardClass: 6.1(a)
PackingGroup: II
HS Code: 29341000
Hazardous Substances Data: 141-84-4(Hazardous Substances Data)
Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. A skin and severe eye irritant. May explode on rapid heating. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Rhodanine Specification

 Rhodanine (CAS NO.141-84-4) also can be called Rhodanine derivative ; 2-Thioxo-1,3-thiazolidin-4-one ; 4-Thiazolidinone, 2-thioxo- ; Rhodanic acid and 2-mercaptothiazolinone . Rhodanine (CAS NO.141-84-4) may explode on rapid heating. It is water soluble. Rhodanine may generate hydrogen sulfide with acids. It may generate heat and hydrogen gas with alkali metals, nitrides, hydrides, and other strong reducing agents.

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