Thioacetanilide supplier | CasNO.637-53-6

Name
THIOACETANILIDE
EINECS
CAS No. 637-53-6
Article Data65
CAS DataBase
Density 1.16g/cm³
Solubility
Melting Point 76-79 °C(lit.)
Formula C8H9 N S
Boiling Point 147 °C / 1mmHg
Molecular Weight 151.232
Flash Point 89.95°C
Transport Information
Appearance yellow crystalline powder
Safety A poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.
Risk Codes R20/21
Molecular Structure
Hazard Symbols Xn
Synonyms Acetanilide,thio- (6CI,7CI,8CI); N-Phenylethanethioamide; N-Phenylthioacetamide; NSC 36984;Thioacetanilide
PSA 44.12000
LogP 2.51880

Synthetic route

: 1600-27-7
mercury(II) diacetate

: bis(thioacetanilide)mercury(II)

A: 637-53-6
thioacetanilide

B: 1563-87-7
N-acetyl-N-phenylacetamide

Conditions

Conditions	Yield
In dichloromethane for 3h; Ambient temperature;	A n/a B 100%

...Expand

: 103-84-4
Acetanilid

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With 2,4-bis(4-(5,5,6,6,7,7,8,8,9,9,10,10,10-tridecafluorodecyloxy)phenyl)-1,3,2,4-dithiadiphosphetane 2,4-disulfide In tetrahydrofuran at 55℃; for 6h;	97%
With 2,4-{[3-[(CH2)5C8F17]-4-MeO-phenyl]}2-P2S2 2,4-disulfide for 0.05h; microwave irradiation;	96%
With Lawessons reagent for 0.0333333h; microwave irradiation;	96%

: 613-91-2
acetophenone oxime

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
Stage #1: acetophenone oxime With triethylamine; p-toluenesulfonyl chloride In acetonitrile at 0 - 20℃; Inert atmosphere; Stage #2: With thiourea In acetonitrile for 2h; Reflux; Inert atmosphere;	90%
With tetraphosphorus decasulfide In benzene at 80℃; for 0.5h; Beckmann Rearrangement;	90%
With trichlorothiophosphine; water; triethylamine at 0 - 75℃; Beckmann rearrangement; chemoselective reaction;	78%

: 98-86-2
acetophenone

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With hydroxylamine hydrochloride; sodium acetate; O,O-Diethyl hydrogen phosphorodithioate In 1,4-dioxane at 80 - 90℃; for 2h; Inert atmosphere;	89%

: 62-53-3
aniline

: 157841-92-4
Thioacetic acid S-(5,5-dimethyl-2-thioxo-2λ5-[1,3,2]dioxaphosphinan-2-yl) ester

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
Stage #1: Thioacetic acid S-(5,5-dimethyl-2-thioxo-2λ5-[1,3,2]dioxaphosphinan-2-yl) ester With 5,5-dimethyl-2-thiolo-2-thiono-1,3,2-dioxaphosphorinane In benzene for 3h; Heating; Stage #2: aniline With triethylamine In benzene cooling; Further stages.;	87.8%

: 62-53-3
aniline

: 507-09-5
thioacetic acid

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With 1H-imidazole; iodine; chloro-diphenylphosphine In dichloromethane for 0.75h; Reflux;	85%
With 1,2-bis(5-methylisoxazol-3-yl)hydrazine; triphenylphosphine In acetonitrile for 4.5h; Mitsunobu reaction; Reflux;	83%

: 110-91-8
morpholine

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

: 103-84-4
Acetanilid

A: 16781-67-2
2-morpholin-4-yl-2-thiazole-4(5H)-one

B: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With MCM-41 mesoporous silica In ethanol; water at 80 - 90℃; for 8h; Green chemistry;	A n/a B 70%

...Expand

: 917-54-4
methyllithium

: 103-72-0
phenyl isothiocyanate

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
In tetrahydrofuran; diethyl ether at -78℃; for 0.5h;	70%

: 142-71-2
copper diacetate

: bis(thioacetanilide)mercury(II)

A: 637-53-6
thioacetanilide

B: 1563-87-7
N-acetyl-N-phenylacetamide

Conditions

Conditions	Yield
In dichloromethane for 120h; Ambient temperature;	A n/a B 59%

...Expand

: 64-19-7
acetic acid

: 62-53-3
aniline

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With O,O-Diethyl hydrogen phosphorodithioate In toluene for 8h; Heating;	51%

: 10319-73-0
C16H16N2S2

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With trifluoroacetic acid In chloroform at 5℃; for 15h;	33%

: 19172-47-5
Lawessons reagent

: 1795-83-1
N-Phenylacetohydroxamic acid

A: N-hydroxy-N-phenyl-thioacetamide

B: C15H16NO4PS

C: 637-53-6
thioacetanilide

D: 103-84-4
Acetanilid

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Further byproducts given. Title compound not separated from byproducts;	A 5% B n/a C 28% D 50 % Spectr.

...Expand

: 16766-09-9
(4-acetamidophenyl)disulfide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
at 240 - 260℃;

: 10394-24-8
N-phenyl-3-thio-malonamic acid

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With water Heating;
beim Erhitzen;

: 594-03-6
dithioacetic acid

: 103-71-9
phenyl isocyanate

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

With toluene

: 594-03-6
dithioacetic acid

: 103-71-9
phenyl isocyanate

: 108-88-3
toluene

A: 463-58-1
carbon oxide sulfide

B: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

...Expand

: 917-64-6
methyl magnesium iodide

: 60-29-7
diethyl ether

: 103-72-0
phenyl isothiocyanate

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
durch nachfolgende Behandlung des Reaktionspr. mit Wasser und verd. Schwefelsaeure;

...Expand

: 917-64-6
methyl magnesium iodide

: 103-72-0
phenyl isothiocyanate

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With diethyl ether und Behandeln des Aetherrueckstandes mit Eiswasser und verd.Schwefelsaeure;

: 594-03-6
dithioacetic acid

: 103-72-0
phenyl isothiocyanate

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

With toluene

: 594-03-6
dithioacetic acid

: 103-72-0
phenyl isothiocyanate

: 108-88-3
toluene

A: 75-15-0
carbon disulfide

B: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

...Expand

: 60-29-7
diethyl ether

: 874-69-1
N-phenylacetimidoyl chloride

: 62-55-5
thioacetamide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
reagiert analog mit N-Phenyl-benzimidchlorid;

...Expand

: 874-69-1
N-phenylacetimidoyl chloride

: 62-55-5
thioacetamide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With diethyl ether

: 60-29-7
diethyl ether

: 4903-36-0
N-phenyl-benzimidoyl chloride

: 2227-79-4
benzenecarbothioamide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

...Expand

: 926-67-0
O-Ethyl thioacetate

: 60-29-7
diethyl ether

: 62-53-3
aniline

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

...Expand

: 926-67-0
O-Ethyl thioacetate

: 62-53-3
aniline

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With diethyl ether

: 60-29-7
diethyl ether

: 874-69-1
N-phenylacetimidoyl chloride

: 2227-79-4
benzenecarbothioamide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

...Expand

: 874-69-1
N-phenylacetimidoyl chloride

: 2227-79-4
benzenecarbothioamide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With diethyl ether

: 103-84-4
Acetanilid

A: 637-53-6
thioacetanilide

B: 621-09-0, 141417-91-6, 1086215-03-3
N,N'-diphenylacetamidine

Conditions

Conditions	Yield
With tetraphosphorus decasulfide

: 10341-75-0
(E)-1-phenylethanone oxime

: 98-09-9
benzenesulfonyl chloride

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield
With pyridine beim Behandeln anschliessend mit H2S;

: 926-67-0
O-Ethyl thioacetate

: anilinomagnesium bromide

: 637-53-6
thioacetanilide

Conditions

Conditions	Yield

: 637-53-6
thioacetanilide

: 103-84-4
Acetanilid

Conditions

Conditions	Yield
With 6H(1+)*Mo9O40PV3(6-); oxygen In acetonitrile at 60℃; under 760.051 Torr; for 0.5h; Inert atmosphere; Glovebox;	99%
With eosin; oxygen In N,N-dimethyl-formamide at 20℃; for 6h; Reagent/catalyst; Solvent; Irradiation; Green chemistry;	93%
With P,P-dichlorophenylphosphine oxide In acetonitrile at -4℃; for 3h;	90%

: 938-10-3
phenylsulfonyl azide

: 637-53-6
thioacetanilide

: N-phenyl-N'-benzenesulfonylacetamidine

Conditions

Conditions	Yield
In ethanol for 1h; Temperature; Solvent; Reflux; chemoselective reaction;	99%
In ethanol at 20℃; for 20h;	63%

: 637-53-6
thioacetanilide

: 536-74-3
phenylacetylene

: 1068465-05-3
N-phenyl-N-[(E)-2-phenylvinyl]thioacetamide

Conditions

Conditions	Yield
With TOP; bis(2-methallyl)(cycloocta-1,5-diene)ruthenium(II) In toluene at 100℃; for 15h; Molecular sieve; Inert atmosphere;	98%

: 637-53-6
thioacetanilide

: 624-90-8, 1516-70-7
Methanesulfonyl azide

: N-phenyl-N'-methanesulfonylacetamidine

Conditions

Conditions	Yield
In ethanol for 1h; Temperature; Solvent; Reflux; chemoselective reaction;	97%

: pentacarbonyl[3-(cyclohex-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

: 637-53-6
thioacetanilide

: syn-pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7-tetrahydro-3aH-inden-1-yl) ester-N]tungsten

Conditions

Conditions	Yield
In diethyl ether under Ar atm. pentacarbonyl(3-(cyclohex-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in diethyl ether at20°C for 25 min; ppt. was collected, washed with n-pentane and dried in vacuo; elem. anal.;	96%

: 637-53-6
thioacetanilide

: 3-(trifluoromethyl)benzenesulfonyl azide

: N'-((3-trifluoromethylphenyl)sulfonyl)-N-phenylacetimidamide

Conditions

Conditions	Yield
In ethanol at 20℃; for 17h;	95%

: pentacarbonyl[3-(cyclohept-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

: 637-53-6
thioacetanilide

: syn-pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7,8-pentahydro-3aH-azulen-1-yl) ester-N]tungsten

Conditions

Conditions	Yield
In diethyl ether under Ar atm. pentacarbonyl(3-(cyclohex-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in diethyl ether at20°C for 25 min; ppt. was collected, washed with n-pentane and dried in vacuo; elem. anal.;	94%

: 637-53-6
thioacetanilide

: 1431968-93-2
3,5-bis(trifluoromethyl)phenylsulfonyl azide

: N'-((3,5-bis(trifluoromethyl)phenyl)sulfonyl)-N-phenylacetimidamide

Conditions

Conditions	Yield
In ethanol at 20℃; for 7h;	93%

: 5256-74-6
1,3-diethyl 2-diazopropanedioate

: 637-53-6
thioacetanilide

: 81022-80-2
diethyl 2-(1-(phenylamino)ethylidene)malonate

Conditions

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride In benzene at 90℃; for 4h; Reagent/catalyst; Time; Inert atmosphere; Sealed tube;	92%
With copper(I)-complexed magnetic nanoparticle catalyst In 1,2-dichloro-ethane at 70℃; for 5h;	90%
With (CuOTf)2*Tol In 1,2-dichloro-ethane at 90℃; for 9h; Inert atmosphere; Sealed tube;	74%

: 2009-97-4
ethyl 2-diazo-3-oxobutanoate

: 637-53-6
thioacetanilide

: 2-acetyl-3-phenylaminobut-2-enoic acid ethyl ester

Conditions

Conditions	Yield
With copper(I)-complexed magnetic nanoparticle catalyst In 1,2-dichloro-ethane at 70℃; for 3h; diastereoselective reaction;	91%

: 10443-65-9
2-bromo-2-propenoic acid

: 637-53-6
thioacetanilide

: 4-carboxy-2-methyl-3-phenyl-Δ2-thiazolinium bromide

Conditions

Conditions	Yield
In toluene at 90℃; for 1h;	90%
In toluene at 90℃;

: tetra[μ-acetato-bis(methanol)]dirhodium

: 637-53-6
thioacetanilide

: Rh2(OC2Me)4(N-phenylthioacetamide)2

Conditions

Conditions	Yield
In ethanol soln. of ligand added to soln. of Rh-complex with stirring (1 h);; filtered, washed with absolute EtOH, dried in vacuo, washed with abundant pentane, elem. anal.;;	90%

: [(Fe(CO)3)2(μ-S(Me)C(CF3)CFC(NMe2))]

: 637-53-6
thioacetanilide

: 436162-62-8
[(Fe(CO)3)2( μ-S(CH3)C(CF3)C β (SC(NPh)Me) C α (N(CH3)2))]

Conditions

Conditions	Yield
In tetrahydrofuran room temp., 3 hs, (Ar); filtration (celite), vac. evapn., washing (-50 °C, pentane), elem. anal.;	90%

: pentacarbonyl[3-(cyclopent-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

: 637-53-6
thioacetanilide

: pentacarbonyl[N-phenyl-thioacetimidic acid (3-ethoxy-2,4,5,6-tetrahydropentalen-1-yl) ester-N]tungsten

Conditions

Conditions	Yield
With triethylamine In dichloromethane under Ar atm. pentacarbonyl(3-(cyclopent-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in dichloromethanein the presence of 1 equiv. triethylamine with stirring for 20 min at 20°C; fast chromy. on silica; elem. anal.;	89%

: 637-53-6
thioacetanilide

: 57959-52-1
1-chloro-1-phenyl-2,2,2-trifluoroethyl isocyanate

: 6-Methylene-2,5-diphenyl-2-trifluoromethyl-[1,3,5]thiadiazinan-4-one

Conditions

Conditions	Yield
With triethylamine In benzene for 3h;	88%

: 637-53-6
thioacetanilide

: 14213-16-2
5-methyl-1-phenyl-1H-tetrazole

Conditions

Conditions	Yield
With sodium azide; tetrachlorosilane In acetonitrile at 20 - 82℃; for 6h;	87%

: 938-81-8
N-nitrosoacetanilide

: 637-53-6
thioacetanilide

A: 2127-03-9
2,2'-dipyridyldisulphide

B: 87107-49-1
N-Phenyl-thioacetimidic acid phenyl ester

C: 103-84-4
Acetanilid

Conditions

Conditions	Yield
Product distribution;	A 86% B 71% C 75%

...Expand

: pentacarbonyl[3-(cyclohept-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

: 637-53-6
thioacetanilide

: pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7,8-pentahydro-3aH-azulen-1-yl) ester-N]tungsten

Conditions

Conditions	Yield
With triethylamine In dichloromethane under Ar atm. pentacarbonyl(3-(cyclohept-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in dichloromethanein the presence of 1 equiv. triethylamine with stirring for 20 min at 20°C; elem. anal.;	86%

: di(rhodium)tetracarbonyl dichloride

: 637-53-6
thioacetanilide

: {Rh2(CO)4(μ-CH3CSN(C6H5))2}

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran byproducts: H2; addn. of N-phenylacetamide to a stirred suspn. of NaH (THF), filtn. of soln. into a stirred soln. of starting Rh-complex (THF, -78°C), all steps under N2; evapg. to dryness, extg. of residue (hexane), concg., cooling to 0°C, elem. anal.;	84%
With triethylamine In not given

: 637-53-6
thioacetanilide

: 6647-85-4
3-nitrobenzenesulfonyl azide

: N'-((3-nitrophenyl)sulfonyl)-N-phenylacetimidamide

Conditions

Conditions	Yield
In ethanol at 20℃; for 20h;	84%

: pentacarbonyl[3-(cyclohex-1-enyl)-1-ethoxy-2-propyn-1-ylidene]tungsten

: 637-53-6
thioacetanilide

: pentacarbonyl[N-phenylthioacetimidic acid (3-ethoxy-4,5,6,7-tetrahydro-3aH-inden-1-yl) ester-N]tungsten

Conditions

Conditions	Yield
With triethylamine In dichloromethane under Ar atm. pentacarbonyl(3-(cyclohex-1-yl)-1-ethoxy-2-propyn-1-ylidene)tungsten was reacted with (N-phenyl)thioacetamide in dichloromethane in the presence of 1 equiv. triethylamine with stirring for 20 min at 20°C; elem. anal.;	83%

: 637-53-6
thioacetanilide

: 1068-57-1
acetic acid hydrazide

: 13576-46-0
3,5-dimethyl-4-phenyl-4H-[1,2,4]triazole

Conditions

Conditions	Yield
With mercury(II) diacetate In tetrahydrofuran microwave irradiation;	82%
In butan-1-ol for 16h; Heating; Yield given;

: (–)-menthone

: 637-53-6
thioacetanilide

: 2-[(1R,2S,5R)-1-hydroxy-5-methyl-2-(propan-2-yl)cyclohexyl]-N-phenylethanethioamide

Conditions

Conditions	Yield
Stage #1: thioacetanilide With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran at -5 - 5℃; for 1.5h; Inert atmosphere; Stage #2: (–)-menthone In tetrahydrofuran at -15 - -5℃; Inert atmosphere; stereoselective reaction;	81%

: 941-55-9
4-toluenesulfonyl azide

: 637-53-6
thioacetanilide

: 27049-62-3
N-phenyl-N'-tosylacetimidamide

Conditions

Conditions	Yield
In pyridine at 90 - 100℃; for 5h;	79%
In ethanol at 20℃; for 20h;	46%

Thioacetanilide Chemical Properties

IUPAC Name: N-Phenylethanethioamide
The MF of Thioacetanilide (CAS NO.637-53-6) is C₈H₉NS.

The MW of Thioacetanilide (CAS NO.637-53-6) is 151.23.
Synonyms of Thioacetanilide (CAS NO.637-53-6): Ethanethioamide, N-phenyl- ; N-Phenylethanthioamid ; Acetanilide, thio- ; Thioacetanilide
Product Categories: Organic Building Blocks;Sulfur Compounds;Thiocarbonyl Compounds
Apperance: yellow crystalline powder
Index of Refraction: 1.653
EINECS: 211-288-4
Density: 1.159 g/ml
Flash Point: 90 °C
Boiling Point: 225.1 °C
Melting Point: 76-79 °C

Thioacetanilide Uses

Thioacetanilide (CAS NO.637-53-6) is used as chemical reagents, organic intermediates, fine chemicals, pharmaceutical research and development.

Thioacetanilide Toxicity Data With Reference

1.	orl-rat LD50:2635 mg/kg	GISAAA Gigiena i Sanitariya. 51 (2)(1986),72.
2.	orl-mus LD50:2625 mg/kg	GISAAA Gigiena i Sanitariya. 51 (2)(1986),72.
3.	ipr-mus LD50:300 mg/kg	NTIS** National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD277-689 .

Thioacetanilide Consensus Reports

Reported in EPA TSCA Inventory.

Thioacetanilide Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.Safety information of Thioacetanilide (CAS NO.637-53-6):
Hazard Codes   Harmful Xn
Risk Statements
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements
S36:Wear suitable protective clothing.
WGK Germany 3
RTECS AE7350000

Product Name

THIOACETANILIDE

Synthetic route

Thioacetanilide Chemical Properties

Thioacetanilide Uses

Thioacetanilide Toxicity Data With Reference

Thioacetanilide Consensus Reports

Thioacetanilide Safety Profile

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