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122-80-5

Basic Information
CAS No.: 122-80-5
Name: Acetamide,N-(4-aminophenyl)-
Article Data: 137
Cas Database
Molecular Structure:
Molecular Structure of 122-80-5 (Acetamide,N-(4-aminophenyl)-)
Formula: C8H10N2O
Molecular Weight: 150.18
Synonyms: Acetanilide,4'-amino- (6CI,7CI,8CI);Acetanilide, p-amino- (4CI);(4-(Acetylamino)phenyl)amine;1-Amino-4-(acetylamino)benzene;4-(Acetylamino)aniline;4-Acetylaminobenzeneamine;Acetparamin;Acetyl-p-phenylenediamine;C.I. 76005;C.I.Oxidation Base 19;Fourrine 88;Fourrine A;N-(4-Aminophenyl)acetamide;N-(p-Aminophenyl)acetamide;N-Acetyl-1,4-benzenediamine;N-Acetyl-p-phenylenediamine;NSC 2135;Paracetamin;p-(Acetylamino)aniline;p-Acetamidoaniline;p-Aminoacetanilide;
EINECS: 204-576-6
Density: 1.203 g/cm3
Melting Point: 164-167 °C(lit.)
Boiling Point: 267.726 °C at 760 mmHg
Flash Point: 115.717 °C
Solubility: 0.1-1 g/100 mL at 25 °C
Appearance: pink to brown fine crystalline powder
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 36-42/43-20/21/22
Safety: 22-26-36/37-39-36
Transport Information: N/A
PSA: 55.12000
LogP: 1.88140
Synthetic route
104-04-1

N-(4-Nitrophenyl)acetamide

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With hydrazine hydrate; nickel In methanol for 6h;100%
With indium; acetic acid In tetrahydrofuran Heating;100%
With trimethylamine-borane; palladium hydroxide - carbon In methanol for 3.5h; Heating;99%
64-19-7

acetic acid

141-78-6

ethyl acetate

106-50-3

1,4-phenylenediamine

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With 1,4-diaza-bicyclo[2.2.2]octane at 65 - 90℃; for 6h; Time; Inert atmosphere;98.6%
38063-81-9

p-aminoacetophenone oxime

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With chlorosulfonic acid In toluene at 90℃; for 0.5h; Beckmann rearrangement;98%
With trifluoromethylsulfonic anhydride In dichloromethane at 20℃; for 3h; Beckmann Rearrangement; Inert atmosphere;94%
With iodine In acetonitrile for 4h; Beckmann rearrangement; Reflux;90%
108-24-7

acetic anhydride

106-50-3

1,4-phenylenediamine

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
at 20℃;95%
In dichloromethane at 20℃; Inert atmosphere;95%
In tetrahydrofuran at 20℃;65%
103-88-8

4-bromoacetanilide

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With bis(triphenylphosphine)nickel(II) chloride; lithium hexamethyldisilazane In 1,4-dioxane at 90℃; for 2h; Glovebox; Sealed tube;91%
Stage #1: 4-bromoacetanilide With lithium hexamethyldisilazane; DavePhos; tris(dibenzylideneacetone)dipalladium (0) In 1,4-dioxane at 100℃; for 17h;
Stage #2: With hydrogenchloride In 1,4-dioxane at 20℃; for 0.0833333h; Further stages.;
70%
622-50-4

4-Acetamido-1-iodobenzene

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate; 1-(5,6,7,8-tetrahydroquinolin-8-yl)-2-methylpropan-1-one; copper(I) bromide In dimethyl sulfoxide at 25℃; for 24h; Inert atmosphere; Sealed tube;90%
539-03-7

N-(4-chlorophenyl)acetamide

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With ammonium hydroxide; potassium phosphate In dimethyl sulfoxide at 80℃; UV-irradiation;89%

N-acetyl-N-(4-chlorophenyl)-4-nitrobenzenesulfonamide

106-50-3

1,4-phenylenediamine

A

16937-03-4

4-nitro-N-(4-chlorophenyl)benzenesulfonamide

B

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With potassium carbonate In water at 80℃; for 2h; Green chemistry; chemoselective reaction;A n/a
B 86%
52578-66-2

N-(4-azido-phenyl)acetamide

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With iron(III) oxide; hydrazine hydrate In water at 120℃; for 1.5h; Inert atmosphere;85%
127740-25-4

2-[(4-acetylaminophenylamino)methylene]malonic acid diethyl ester

122-80-5

N-acetyl-p-phenylenediamine

Conditions
ConditionsYield
With ethylenediamine In ethanol at 20℃; for 1.3h;80%
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Specification

The p-Amino acetanilide with CAS registry number of 122-80-5 is also called Acetamide,N-(4-aminophenyl)-. The IUPAC name is N-(4-aminophenyl)acetamide. Its EINECS registry number is 204-576-6. In addition, the molecular formula is C8H10N2O and the molecular weight is 150.1778. It belongs to the classes of Amineprimary; Intermediates of Dyes and Pigments; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts. It is a kind of white or slightly reddish solid. And it is slightly soluble in water. What's more, it should be stored in a airtight, cool and dry place.

Physical properties about this chemical are: (1)ACD/LogP: 0.08; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0; (4)ACD/LogD (pH 7.4): 0; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 22; (8)ACD/KOC (pH 7.4): 26; (9)#H bond acceptors: 3; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 55.12 Å2; (13)Index of Refraction: 1.636; (14)Molar Refractivity: 44.761 cm3; (15)Molar Volume: 124.796 cm3; (16)Polarizability: 17.745 ×10-24cm3; (17)Surface Tension: 53.079 dyne/cm; (18)Density: 1.203 g/cm3; (19)Flash Point: 115.717 °C; (20)Enthalpy of Vaporization: 50.577 kJ/mol; (21)Boiling Point: 267.726 °C at 760 mmHg; (22)Vapour Pressure: 0.008 mmHg at 25°C.

Preparation of p-Amino acetanilide: it can be prepared by p-nitroacetylaniline. p-Nitroacetylaniline can be prepared by acetylaniline. At first, you can put the sulfuric acid into the kettle, then add the acetylaniline in 2-2.5 hours with stirring at the temperature of 20-25 °C and make the whole to dissolve. Then cool the mixture to 4-7 ℃, add mix acid in 20 hours by dropping. After the separation process, you can get p-nitroacetylaniline. At last, you can use iron powder to resolve p-nitroacetylaniline to get  p-Amino acetylaniline.

Uses of p-Amino acetanilide: it can be used in organic synthesis and pharmaceutical industry. it can be used as Azo Dye Intermediates. It can react with hexane-1-sulfonyl chloride to get N-(4-acetamidophenyl)sulfamoylhexane. This reaction will need reagent  pyridine. The yield is about 83%.

P-Amino acetanilide can react with to hexane-1-sulfonyl chloride get N-(4-acetamidophenyl)sulfamoylhexane

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes and harmful by inhalation, in contact with skin and if swallowed. And it may cause sensitization by inhalation and skin contact. During using it, you should  not breathe dust and should wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: Nc1ccc(NC(C)=O)cc1
(2)InChI: InChI=1/C8H10N2O/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11)
(3)InChIKey: CHMBIJAOCISYEW-UHFFFAOYAK

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 633mg/kg (633mg/kg)   Meditsina Truda i Promyshlennaya Ekologiya. Industrial Medicine and Ecology. Vol. (10), Pg. 36, 1996.
rat LD50 oral 2500mg/kg (2500mg/kg)   Meditsina Truda i Promyshlennaya Ekologiya. Industrial Medicine and Ecology. Vol. (10), Pg. 36, 1996.