4-Aminoacetanilide

4-Aminoacetanilide or paracetamin is a chemical compound which is a amino derivative of acetanilide and para-isomer of aminoacetanilide. There are two other isomers of aminoacetanilide, 2-aminoacetanilide and 3-aminoacetanilide. Aminoacetanilide derivatives are important synthetic intermediates in heterocyclic and aromatic synthesis. These derivatives have found applications in pharmaceutical industry and dyes and pigment industry.^[1]

4-Aminoacetanilide

Names
Preferred IUPAC name N-(4-Aminophenyl)acetamide
Other names p-Aminoacetanilide, N-(4-Aminophenyl)acetamide
Identifiers
CAS Number	122-80-5 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:229632
ChEMBL	ChEMBL1318876
ChemSpider	10297844 N
ECHA InfoCard	100.004.161
EC Number	204-576-6
PubChem CID	31230
UNII	IH5OX0I3Z9
CompTox Dashboard (EPA)	DTXSID7024455
InChI InChI=1S/C8H10N2O/c1-6(11)10-8-4-2-7(9)3-5-8/h2-5H,9H2,1H3,(H,10,11) Key: CHMBIJAOCISYEW-UHFFFAOYSA-N
SMILES NC1=CC=C(NC(C)=O)C=C1
Properties
Chemical formula	C8H10N2O
Molar mass	150.181 g·mol−1
Appearance	leaf or flake like white-Pink To Brown Powder
Density	1.1392
Melting point	164–167 °C (327–333 °F; 437–440 K)
Boiling point	267 °C (513 °F; 540 K)
Solubility in water	0.1-1 g/100 mL at 25 °C
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H317, H319, H334
Precautionary statements	P261, P264, P272, P280, P285, P302+P352, P304+P341, P305+P351+P338, P321, P333+P313, P337+P313, P342+P311, P363, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Synthesis

Becillus cereus converts 4-phenylenediamine to 4-aminoacetanilide.^[1][2] Reduction of 4-nitroacetanilide by hydrogenation catalyst generates 4-aminoacetanilide.^[3] Green synthesis of p-Aminoacetanilide is achieved by reducing p-nitroaetanilide using Zn/NH₄Cl in water.^[4] Number of methods are available to reduce 4-nitroacetanilide using different catalyst and reaction conditions.^[1]

Uses

4-Aminoacetanilide is used as in intermediate in the production of some dyes.^[5] 4-aminoacetanilide is also used for the synthesis of beta-lactams.^[6]