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Basic Information
CAS No.: 637-53-6
Name: THIOACETANILIDE
Article Data: 65
Molecular Structure:
Molecular Structure of 637-53-6 (THIOACETANILIDE)
Formula: C8H9 N S
Molecular Weight: 151.232
Synonyms: Acetanilide,thio- (6CI,7CI,8CI); N-Phenylethanethioamide; N-Phenylthioacetamide; NSC 36984;Thioacetanilide
Density: 1.16g/cm3
Melting Point: 76-79 °C(lit.)
Boiling Point: 147 °C / 1mmHg
Flash Point: 89.95°C
Appearance: yellow crystalline powder
Hazard Symbols: Xn
Risk Codes: R20/21
Safety: A poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and SOx.
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
ConditionsYield
In dichloromethane for 3h; Ambient temperature;A n/a
B 100%
103-84-4

Acetanilid

637-53-6

thioacetanilide

Conditions
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
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
ConditionsYield
With MCM-41 mesoporous silica In ethanol; water at 80 - 90℃; for 8h; Green chemistry;A n/a
B 70%
917-54-4

methyllithium

103-72-0

phenyl isothiocyanate

637-53-6

thioacetanilide

Conditions
ConditionsYield
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
ConditionsYield
In dichloromethane for 120h; Ambient temperature;A n/a
B 59%
64-19-7

acetic acid

62-53-3

aniline

637-53-6

thioacetanilide

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

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

Uses

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

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 .

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

A poison by intraperitoneal route. Moderately toxic by ingestion. When heated to decomposition it emits very toxic fumes of NOx and SOx.Safety information of Thioacetanilide (CAS NO.637-53-6):
Hazard Codes  HarmfulXn
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