Rhodanine supplier | CasNO.141-84-4

Name
Rhodanine
EINECS 205-505-1
CAS No. 141-84-4
Article Data33
CAS DataBase
Density 1.59 g/cm³
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
Hazard Symbols Xn
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;
PSA 86.49000
LogP 0.46310

Synthetic route

: 75-15-0
carbon disulfide

: 3926-62-3
sodium monochloroacetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
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

Conditions	Yield
With hydrogenchloride; sodium acetate; acetic acid In N,N-dimethyl-formamide	A 83% B n/a

...Expand

: 68-11-1
mercaptoacetic acid

: 17356-08-0
thiourea

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With water

: 1438-16-0
3-aminorhodanine

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride; sodium nitrite

: 463-56-9
thiocyanic acid

: 4438-95-3
thiocyanato-acetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With diethyl ether

: 29596-83-6
(thiocarbamoylthio)acetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

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

: 5349-28-0
thiocyanato-acetic acid ethyl ester

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With ethanol; hydrogen sulfide Zufuegen von Salzsaeure und folgend Eindampfen;

: 899417-89-1
thiocarbamoylsulfanyl-acetic acid ethyl ester

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With ethanol
With water

: 55602-07-8
diethyl 2-thiocyanatomalonate

: 98-91-9
thiobenzoic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With benzene Erhitzen des Reaktionsprodukts mit wss. HCl;

: 75-15-0
carbon disulfide

: 556-90-1
pseudothiohydantoin

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With ethanol at 160℃; im Rohr;

: 90669-10-6
thiocarbamoylsulfanyl-acetic acid anilide

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With sulfuric acid

: 540-72-7
sodium thiocyanide

: 3926-62-3
sodium monochloroacetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With water anschliessendes Erwaermen mit wss. HCl;

: 1147550-11-5
ammonium thiocyanate

: 3926-62-3
sodium monochloroacetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With water anschliessendes Erwaermen mit wss. HCl;

: 333-20-0
potassium thioacyanate

: 68-11-1
mercaptoacetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride; ethanol

: 1147550-11-5
ammonium thiocyanate

: 79-11-8
chloroacetic acid

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With water

: 98664-36-9
4-N'-acetylphenylhydrazono-2-thiazolidinethione

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Heating;

: 98664-37-0
3,4,6,8-Tetrahydro-2-phenyl-2H-thiazolo<3,4-c>-1,2,4-triazin-6-thioxo-4-one

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Heating;

: 98664-36-9
4-N'-Acetylphenylhydrazono-2-thiazolidinethione

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Heating;

: 105-39-5
chloroacetic acid ethyl ester

dithiocarbamidacidic ammonium: dithiocarbamidacidic ammonium

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride; ethanol

: 79-11-8
chloroacetic acid

dithiocarbamidacidic ammonium: dithiocarbamidacidic ammonium

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With water folgend Eintragen in konz. Salzsaeure bei 80-90grad oder in Salzsaeure bei 90-95grad;

: 64-17-5
ethanol

: 6326-83-6
bis(carboxymethyl)trithiocarbonate

: 7664-41-7
ammonia

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
at 25℃; bei unterschiedlichem Mengenverhaeltnis der Reaktionspartner und unterschiedlicher Reaktionsdauer;

...Expand

: 7664-93-9
sulfuric acid

: 90669-10-6
thiocarbamoylsulfanyl-acetic acid anilide

: 141-84-4
2-thioxo-4-thiazolidinone

: 6326-83-6
bis(carboxymethyl)trithiocarbonate

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
Stage #1: bis(carboxymethyl)trithiocarbonate With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1.5h; Stage #2: With ammonia In tetrahydrofuran for 4h; Reflux;

: 3926-62-3
sodium monochloroacetic acid

: 513-74-6
ammonium dithiocarbamate

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With hydrogenchloride In water at 85 - 90℃;
With hydrogenchloride In water at 85 - 90℃;

: 24066-82-8
ethyl 2-isothiocyanatoacetate

: 141-84-4
2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 6h;

: 141-84-4
2-thioxo-4-thiazolidinone

: 104-55-2
3-phenyl-propenal

: 15328-87-7
5-(3-phenyl-allylidene)-2-thioxo-thiazolidin-4-on e

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%
With thiourea; urea at 110℃; for 0.1h; Knoevenagel condensation; Neat (no solvent);	91%
With sodium hydroxide

: 141-84-4
2-thioxo-4-thiazolidinone

: 43111-11-1
5-formyl-8-methoxypsoralen

: 105245-75-8
4-<(4-Oxo-2-thioxo-1,3-thiazolidin-5-yl)-methyleno>xanthotoxin

Conditions

Conditions	Yield
With sodium acetate In acetic acid for 2h; Heating;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 4649-09-6
1H-pyrrolo[2,3-b]pyridin-3-carbaldehyde

: 937012-09-4
(Z)-5-(1H-pyrrolo-[2,3-b]pyridin-3-ylmethylene)-2-thioxo-1,3-thiazolidin-4-one

Conditions

Conditions	Yield
With sodium acetate In acetic acid for 12h; Heating / reflux;	100%
With sodium acetate; acetic acid for 5h; Reflux;	88%
With sodium acetate In acetic acid for 5h; Heating / reflux;	88%
With piperidine In ethanol at 70℃; for 16h; Knoevenagel Condensation;	73%

: 141-84-4
2-thioxo-4-thiazolidinone

: 872576-87-9
4-ethoxy-6-formyl-quinoline-3-carbonitrile

: 872576-94-8
4-ethoxy-6-[4-oxo-2-thioxo-thiazolidin-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile

Conditions

Conditions	Yield
With ammonium acetate In toluene for 6h; Knoevenagel Condensation; Heating / reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 879323-78-1
4-ethoxy-quinoline-6-carbaldehyde

: 879324-55-7
5-[1-(4-ethoxy-quinolin-6-yl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one

Conditions

Conditions	Yield
With acetic acid for 12h; Heating / reflux;	100%

: 439811-22-0
quinazoline-6-carbaldehyde

: 141-84-4
2-thioxo-4-thiazolidinone

: 5-quinazolin-6-ylmethylene-2-thioxo-thiazolidin-4-one

Conditions

Conditions	Yield
With sodium acetate; acetic acid at 130℃; for 12h;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 66-77-3
1-naphthaldehyde

: 181765-58-2
(Z)-5-(naphthalen-1'-ylmethylene)-2-thioxothiazolidin-4-one

Conditions

Conditions	Yield
With acetic acid; triethylamine In ethyl acetate at 85℃; for 3h;	100%
With sodium acetate; acetic acid for 16h; Reflux;	82%
With sodium acetate In acetic acid Reflux;	76%
With piperidine In ethanol at 70℃; for 16h; Knoevenagel Condensation;	59%

: 141-84-4
2-thioxo-4-thiazolidinone

: 100-83-4
meta-hydroxybenzaldehyde

: (3-hydroxyphenyl)methylene-2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With sodium acetate; acetic acid In toluene for 4h; Reflux; Dean-Stark;	100%
In isopropyl alcohol at 80 - 90℃; for 2h;	75%
With piperidine; acetic acid for 0.333333h; Knoevenagel Condensation; Microwave irradiation;

: 141-84-4
2-thioxo-4-thiazolidinone

: 60125-23-7, 3541-42-2
2'-hydroxycinnamaldehyde

: 18097-60-4
C12H9NO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 2'-benzoyloxycinnamaldehyde

: 1443442-56-5
C19H13NO3S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 3-(2'-O-benzylphenyl)-2-propenal

: 1443442-57-6
C19H15NO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1443442-69-0
C17H16O2

: 1443442-58-7
C20H17NO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1443442-70-3
C16H13BrO2

: 1443442-59-8
C19H14BrNO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1443442-71-4
C17H13F3O2

: 1443442-60-1
C20H14F3NO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 837387-04-9
C17H16O3

: 1443442-61-2
C20H17NO3S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 837387-05-0
C17H16O3

: 1443442-62-3
C20H17NO3S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1443442-72-5
C16H12Br2O2

: 1443442-63-4
C19H13Br2NO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 208118-64-3
C15H12O4S

: 1443442-64-5
C18H13NO4S3

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 94298-53-0
C16H13NO2

: 1443442-65-6
C19H14N2O2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1794-45-2
2-chlorocinnamaldehyde

: 15328-88-8
5-[3-(2-chloro-phenyl)-allylidene]-2-thioxo-thiazolidin-4-one

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1504-74-1
2-methoxycinnamaldehyde

: 15328-91-3
C13H11NO2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1202464-30-9
C15H13NO2

: 1443442-66-7
C18H14N2O2S2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 28447-15-6
3-(3-pyridyl)acrolein

: 1443442-67-8
C11H8N2OS2

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1039844-65-9
C14H10Br2O2

: 893449-38-2
5-[[5-bromo-2-[(2-bromophenyl)methoxy]phenyl]methylene]-2-thioxo-4-thiazolidinone

Conditions

Conditions	Yield
With ammonium acetate; acetic acid In toluene Reflux;	100%

: 141-84-4
2-thioxo-4-thiazolidinone

: 100-52-7
benzaldehyde

: 3806-42-6
5-benzylidene-2-thioxothiazolidin-4-one

Conditions

Conditions	Yield
With thiourea; urea at 110℃; for 0.0833333h; Knoevenagel condensation; Neat (no solvent);	99%
With urea/choline chloride eutectic salt at 80℃; for 0.75h; Catalytic behavior; Temperature; Aldol Condensation;	96%
With tetra(n-butyl)ammonium hydroxide In ethanol; water at 50℃; for 1.5h; Green chemistry;	95%

: 141-84-4
2-thioxo-4-thiazolidinone

: 1948-40-9
4-hydroxy-3,5-diiodobenzaldehyde

: (Z)-5-(3',5'-diiodo-4'-hydroxybenzylidene)-2-thioxothiazolidin-4-one

Conditions

Conditions	Yield
With sodium acetate; acetic acid for 16h; Heating;	99%
With ammonium acetate In toluene at 110℃; for 24h; Inert atmosphere; Darkness;	94%

: 141-84-4
2-thioxo-4-thiazolidinone

: 4748-78-1
4-ethylbenzylaldehyde

: (5Z)-5-[(4-ethylphenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one

Conditions

Conditions	Yield
With ammonium acetate; acetic acid for 1h; Reflux; stereoselective reaction;	99%
With ammonium acetate; acetic acid for 1 - 12h; Heating / reflux;

: 123-75-1
pyrrolidine

: 141-84-4
2-thioxo-4-thiazolidinone

: 105-07-7
4-cyanobenzaldehyde

: 4-{[4-oxo-2-(pyrrolidin-1-yl)thiazol-5(4H)-ylidene]methyl}benzonitrile

Conditions

Conditions	Yield
With acetic acid In ethanol at 150℃; Microwave irradiation;	99%
With magnesia In ethanol; water at 50℃; for 1.66667h; Knoevenagel Condensation;	78%

...Expand

: 141-84-4
2-thioxo-4-thiazolidinone

: 443-69-6
5-fluoro-1H-indole-2,3-dione

: 5-(5-Fluoro-3-hydroxy-2-oxoindolin-3- yl)-2-thioxothiazolidin-4-one

Conditions

Conditions	Yield
With water at 20℃; for 12h;	99%

: 141-84-4
2-thioxo-4-thiazolidinone

: 39755-95-8
5-methoxyisatine

: 3-hydroxy-5-methoxy-3-(4-oxo-2-thioxothiazolidin-5-yl)indolin-2-one

Conditions

Conditions	Yield
With water at 20℃; for 12h;	99%

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: Harmful Xn
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 NO_x and SO_x.

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.

Product Name

Rhodanine

Synthetic route

Rhodanine Chemical Properties

Rhodanine Toxicity Data With Reference

Rhodanine Consensus Reports

Rhodanine Safety Profile

Rhodanine Specification

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