5-(4-Dimethylaminobenzylidene)rhodanine supplier

Name
5-(4-DIMETHYLAMINOBENZYLIDENE)RHODANINE
EINECS 208-625-2
CAS No. 536-17-4
Article Data17
CAS DataBase
Density 1.368 g/cm³
Solubility Insoluble in water, 993.7(mg/L) at 25°C
Melting Point 285-288 °C(lit.)
Formula C₁₂H₁₂N₂OS₂
Boiling Point 430 °C at 760 mmHg
Molecular Weight 264.372
Flash Point 213.8 °C
Transport Information
Appearance red fluffy powder
Safety 22-24/25-36/37-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Rhodanine,5-[p-(dimethylamino)benzylidene]- (6CI,7CI,8CI);4'-(Dimethylamino)benzalrhodanine;5-[4-(Dimethylamino)benzylidene]-2-thioxo-4-thiazolidone;NSC 5042;p-(Dimethylamino)benzal-5-rhodanine;
PSA 89.73000
LogP 2.57020

Synthetic route

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

: 100-10-7
4-dimethylamino-benzaldehyde

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

Conditions

Conditions	Yield
With thiourea; urea at 110℃; for 0.0833333h; Knoevenagel condensation; Neat (no solvent);	96%
With (2-hydroxyethyl)ammonium formate at 20℃; for 0.05h; Knoevenagel condensation; neat (no solvent);	90%
With sodium acetate; acetic acid at 120℃;	90%

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

: 889-37-2, 1613-99-6
N,N-dimethyl-4-((phenylimino)methyl)aniline

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

Conditions

Conditions	Yield
In acetic acid

: 3-Benzoyl-5-[1-(4-dimethylamino-phenyl)-meth-(Z)-ylidene]-2-thioxo-thiazolidin-4-one

A: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

B: 65-85-0
benzoic acid

Conditions

Conditions	Yield
With hydrogen cation In water

: C12H11N2OS2(1-)*Na(1+)

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: H+ / H2O View Scheme

: 1660-94-2
Tetraethyl methylenediphosphonate

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 634915-49-4
[1-(diethoxy-phosphoryl)-2-(4-dimethylamino-phenyl)-2-(4-oxo-2-thioxo-thiazolidin-5-yl)-ethyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol; N,N-dimethyl-formamide for 0.133333h; Michael addition reaction; microwave irradiation;	87%

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 13939-06-5, 199620-15-0
molybdenum hexacarbonyl

: 952576-76-0
Mo(CO)5[5-(4-dimethylaminobenzylidene)rhodanine]

Conditions

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); Mo complex and rhodanine deriv. dissolved in THF; soln. irradiated for 2h using 400 W medium pressure Hg lamp; solvent evapd. under vac.; solid extd. with CH2Cl2; petroleum ether added; ppt. washed with petroleum ether; dried under vac.; unreacted Cr complex sublimed out in vac.; elem. anal.;	82%

: 50-00-0
formaldehyd

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 51207-85-3
4-amino-N,N-diethylbenzamide

: 104183-56-4
5-(p-Dimethylaminobenzylidene)-3--4-oxo-thiazolidine-2-thione

Conditions

Conditions	Yield
In ethanol; water Heating;	81%

...Expand

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 22303-36-2
N-(4-methoxyphenyl)-2-chloroacetamide

: Z-N-(4-methoxyphenyl)-2-(5-(4-(dimethylamino)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 36h;	80%

: 50-00-0
formaldehyd

: 42837-37-6
4-(N-piperidinocarbonyl)aniline

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 104183-54-2
5-(p-Dimethylaminobenzylidene)-3--4-oxo-thiazolidine-2-thione

Conditions

Conditions	Yield
In ethanol; water Heating;	78%

...Expand

: 50-00-0
formaldehyd

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 79834-39-2
p-(4-Phenylpiperazin-1-ylcarbamoyl)aniline

: 104183-53-1
5-(p-Dimethylaminobenzylidene)-3--4-oxo-thiazolidine-2-thione

Conditions

Conditions	Yield
In ethanol; water Heating;	74%

...Expand

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 199620-14-9, 13007-92-6
chromium(0) hexacarbonyl

: 952576-75-9
Cr(CO)5[5-(4-dimethylaminobenzylidene)rhodanine]

Conditions

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); Cr complex and rhodanine deriv. dissolved in THF; soln. irradiated for 2h using 400 W medium pressure Hg lamp; solvent evapd. under vac.; solid extd. with CH2Cl2; petroleum ether added; ppt. washed with petroleum ether; dried under vac.; unreacted Cr complex sublimed out in vac.; elem. anal.;	73%

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 3289-75-6
2-chloro-N-(4-chlorophenyl)acetamide

: Z-N-(4-chlorophenyl)-2-(5-(4-(dimethylamino)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 36h;	73%

: 50-00-0
formaldehyd

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 51207-86-4
(4-amino-phenyl)-morpholin-4-yl-methanone

: 104183-55-3
5-(p-Dimethylaminobenzylidene)-3--4-oxo-thiazolidine-2-thione

Conditions

Conditions	Yield
In ethanol; water Heating;	72%

...Expand

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 2564-02-5
N-(4-bromophenyl)-2-chloroacetamide

: Z-N-(4-bromophenyl)-2-(5-(4-(dimethylamino)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 36h;	71%

: 14040-11-0
tungsten hexacarbonyl

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 952576-77-1
W(CO)5[5-(4-dimethylaminobenzylidene)rhodanine]

Conditions

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); W complex and rhodanine deriv. dissolved in THF; soln. irradiated for 2 h using 400 W medium pressure Hg lamp; solvent evapd. under vac.; solid extd. with CH2Cl2; petroleum ether added; ppt. washed with petroleum ether; dried under vac.; unreacted Cr complex sublimed out in vac.; elem. anal.;	70%

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 6974-56-7
2-chloro-N-(2,4-dichlorophenyl)acetamide

: Z-N-(2,4-dichlorophenyl)-2-(5-(4-(dimethylamino)benzylidene)-4-oxo-2-thioxothiazolidin-3-yl)acetamide

Conditions

Conditions	Yield
With sodium hydrogencarbonate; sodium iodide In N,N-dimethyl-formamide at 20℃; for 36h;	70%

: 14220-21-4
rhenium(I) pentacarbonyl bromide

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 952576-78-2
cis-Re(CO)4[5-(4-dimethylaminobenzylidene)rhodanine]

Conditions

Conditions	Yield
In tetrahydrofuran Irradiation (UV/VIS); Re complex and rhodanine deriv. dissolved in THF; soln. irradiated for 2h using 400 W medium pressure Hg lamp; solvent evapd. under vac.; solid extd. with CH2Cl2; petroleum ether added; ppt. washed with petroleum ether; dried under vac.; unreacted Cr complex sublimed out in vac.; elem. anal.;	68%

: 12146-36-0
tetracarbonylnorbornadienchrom

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 1123204-07-8
cis-[(5-(4-dimethylaminobenzylidene)rhodanine)tetra-carbonylchromate(0)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: norbornadiene; Irradiation (UV/VIS); Ar, equimol., a soln. of metal compd. irradiated for 1.5 h, cooled, N compd. added, stirred for 3 h; solvent evapd. (vac.), extd. (CH2Cl2). pptd. (petroleum ether), ppt. washed (petroleum ether), dried (vac.); elem. anal.;	62%

: 12146-37-1, 124717-04-0
(bicyclo[2.2.1]hepta-2,5-diene)tetracarbonylmolybdenum(0)

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 1123204-08-9
cis-[(5-(4-dimethylaminobenzylidene)rhodanine)tetra-carbonylmolybdate(0)]

Conditions

Conditions	Yield
In tetrahydrofuran byproducts: norbornadiene; Irradiation (UV/VIS); Ar, equimol., a soln. of metal compd. irradiated for 1.5 h, cooled, N compd. added, stirred for 3 h; solvent evapd. (vac.), extd. (CH2Cl2). pptd. (petroleum ether), ppt. washed (petroleum ether), dried (vac.); elem. anal.;	54%

: 1067-74-9
Methyl diethylphosphonoacetate

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: {6-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3,5-dioxo-tetrahydro-thiazolo[2,3-b]thiazol-2-yl}-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 20℃; for 72h;	52%

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: {6-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3,5-dioxo-tetrahydro-thiazolo[2,3-b]thiazol-2-yl}-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol at 20℃; for 72h;	50%

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 682-30-4
Diethyl vinylphosphonate

A: 31982-65-7
5-(4'-dimethylamino-phenylmethylene)-2-(ethylthio)-1,3-thiazol-4-one

B: (2-{5-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-4-oxo-4,5-dihydro-thiazol-2-ylsulfanyl}-ethyl)-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With lithium hydride In N,N-dimethyl-formamide for 12h; Heating;	A 28% B 44%

...Expand

: 2537-48-6
diethyl 1-cyanomethylphosphonate

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

A: 2-[5-(4-oxo-2-thioxo-2,4H-1,3-thiazolo)]-1-cyano-2-(dimethylaminophenyl)-ethan-1-yl-phosphonic acid diethyl ester

B: {3-Amino-6-[1-(4-dimethylamino-phenyl)-meth-(Z)-ylidene]-5-oxo-5,6-dihydro-thiazolo[2,3-b]thiazol-2-yl}-phosphonic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: diethyl 1-cyanomethylphosphonate With lithium hydride In N,N-dimethyl-formamide for 1h; Heating; Stage #2: 5-(4-dimethylaminobenzylidene)rhodanine In N,N-dimethyl-formamide Heating;	A 30% B 33%

...Expand

: 867-13-0
diethoxyphosphoryl-acetic acid ethyl ester

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

A: diethyl 2-[5-(4-dimethylaminophenylmethylene)-4-oxo-4H-1,3-thiazol-2-yl]-1,2-ethylenedicarboxylate

B: {6-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3,5-dioxo-tetrahydro-thiazolo[2,3-b]thiazol-2-yl}-phosphonic acid diethyl ester

C: 762292-91-1
[7-(4-dimethylamino-phenyl)-3-ethyl-5-oxo-2-thioxo-3,5,6,7-tetrahydro-2H-pyrano[2,3-d]thiazol-6-yl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 24h; Heating;	A 28% B 14% C 30%

...Expand

: 1067-74-9
Methyl diethylphosphonoacetate

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

A: dimethyl 2-[5-(4-dimethylaminophenylmethylene)-4-oxo-4H-1,3-thiazol-2-yl]-1,2-ethylenedicarboxylate

B: {6-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-3,5-dioxo-tetrahydro-thiazolo[2,3-b]thiazol-2-yl}-phosphonic acid diethyl ester

C: 762292-91-1
[7-(4-dimethylamino-phenyl)-3-ethyl-5-oxo-2-thioxo-3,5,6,7-tetrahydro-2H-pyrano[2,3-d]thiazol-6-yl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
With sodium ethanolate In ethanol for 24h; Heating;	A 30% B 13% C 29%

...Expand

: 1660-94-2
Tetraethyl methylenediphosphonate

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

A: {5-[1-(4-Dimethylamino-phenyl)-meth-(Z)-ylidene]-4-oxo-4,5-dihydro-thiazol-2-ylmethyl}-phosphonic acid diethyl ester

B: 634915-49-4
[1-(diethoxy-phosphoryl)-2-(4-dimethylamino-phenyl)-2-(4-oxo-2-thioxo-thiazolidin-5-yl)-ethyl]-phosphonic acid diethyl ester

Conditions

Conditions	Yield
Stage #1: Tetraethyl methylenediphosphonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 5-(4-dimethylaminobenzylidene)rhodanine In N,N-dimethyl-formamide at 20℃;	A 22% B 28%

...Expand

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 99981-54-1
3-(4-dimethylamino-phenyl)-propionic acid amide

Conditions

Conditions	Yield
With methanol; nickel

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 857205-41-5
3-(4-dimethylamino-phenyl)-2-thioxo-propionic acid

Conditions

Conditions	Yield
With sodium hydroxide

: 186581-53-3, 908094-01-9
diazomethane

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

A: 28996-10-3
5-(4-dimethylamino-benzylidene)-2-methylsulfanyl-thiazol-4-one

B: 23517-84-2
5-(4-dimethylamino-benzylidene)-3-methyl-2-thioxo-thiazolidin-4-one

Conditions

Conditions	Yield
In ethanol

...Expand

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 75-03-6
ethyl iodide

: 31982-65-7
5-(4'-dimethylamino-phenylmethylene)-2-(ethylthio)-1,3-thiazol-4-one

Conditions

Conditions	Yield
With triethylamine In 1,4-dioxane

: 50-00-0
formaldehyd

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 334-22-5
N,N-bis(chloro-2-ethyl)amine

: 7751-32-8
3-{[bis-(2-chloro-ethyl)-amino]-methyl}-5-(4-dimethylamino-benzylidene)-2-thioxo-thiazolidin-4-one

Conditions

Conditions	Yield
In ethanol at 0 - 5℃;

...Expand

: 536-17-4
5-(4-dimethylaminobenzylidene)rhodanine

: 4303-28-0
5-(4-dimethylamino-benzylidene)-thiazolidine-2,4-dithione

Conditions

Conditions	Yield
With tetraphosphorus decasulfide In 1,4-dioxane for 0.5h; Heating;

5-(4-Dimethylaminobenzylidene)rhodanine Chemical Properties

IUPAC Name: (5E)-5-[(4-Dimethylaminophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one
CAS: 536-17-4
Formula: C₁₂H₁₂N₂OS₂
Molecular Weight: 264.37
Molecular Structure of (5E)-5-[(4-Dimethylaminophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one (CAS NO.536-17-4):

Density: 1.36 g/cm³
Flash Point: 213.8 °C
Melting Point: 285-288 °C(lit.)
Boiling Point: 430 °C at 760 mmHg
Index of Refraction: 1.703
Molar Refractivity: 74.94 cm³
Molar Volume: 193.1 cm³
Polarizability: 29.7×10^-24cm³
Surface Tension: 68.3 dyne/cm
Enthalpy of Vaporization: 68.53 kJ/mol
Appearance: red fluffy powder
Vapour Pressure: 1.35E-07 mmHg at 25°C
Water Solubility: 993.7(mg/L) at 25°C
Product Categories: building blocks;heterocyclic building blocks;thiazoles.

5-(4-Dimethylaminobenzylidene)rhodanine Toxicity Data With Reference

ipr-mus LD50:150 mg/kg

NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD603-561 .

5-(4-Dimethylaminobenzylidene)rhodanine Consensus Reports

Reported in EPA TSCA Inventory.

5-(4-Dimethylaminobenzylidene)rhodanine Safety Profile

Poison by intraperitoneal route. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.
Safety Information about (5E)-5-[(4-Dimethylaminophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one (CAS NO.536-17-4):
Hazard Codes:
Xi:
Risk Statements about (5E)-5-[(4-Dimethylaminophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one (CAS NO.536-17-4):
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements about (5E)-5-[(4-Dimethylaminophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one (CAS NO.536-17-4):
S22: Do not breathe dust.
S23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer).
S24/25: Avoid contact with skin and eyes.
S36/37: Wear suitable protective clothing and gloves.
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
WGK Germany: 3
RTECS: VI8090000

5-(4-Dimethylaminobenzylidene)rhodanine Specification

The chemical synonyms of (5E)-5-[(4-Dimethylaminophenyl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one (CAS NO.536-17-4) are 5-((4-(Dimethylamino)phenyl)methylene)-2-thioxo-4-thiazolidinon ; 5-(p-(Dimethylamino)benzylidene)-rhodanin ; 5-(p-Dimethylaminobenzal)rhodanine ; 5-(p-Dimethylaminobenzoylidene)rhodanine ; 5-[[4-(Dimethylamino)phenyl]methylene]-2-thioxo-4-thiazolidinon ; 5-[4-(Dimethylamino)phenyl]methylene-2-thioxo-4-Thiazolidinone ; p-(Dimethylamino)benzal-5-rhodanine ; p-Dimethylaminobenzalrhodanin . As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Use water spray, dry chemical, carbon dioxide, or chemical foam. Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Store in a cool, dry place. Store in a tightly closed container. It can be used as organic reagents pharmaceutical intermediate.

Product Name

5-(4-DIMETHYLAMINOBENZYLIDENE)RHODANINE

Synthetic route

5-(4-Dimethylaminobenzylidene)rhodanine Chemical Properties

5-(4-Dimethylaminobenzylidene)rhodanine Toxicity Data With Reference

5-(4-Dimethylaminobenzylidene)rhodanine Consensus Reports

5-(4-Dimethylaminobenzylidene)rhodanine Safety Profile

5-(4-Dimethylaminobenzylidene)rhodanine Specification

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