4-Aminoacetanilide

4-Aminoacetanilide
Names
	Preferred IUPAC name N-(4-Aminophenyl)acetamide
	Other names p-Aminoacetanilide, N-(4-Aminophenyl)acetamide
Identifiers
CAS Number	122-80-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:229632;
ChEMBL	ChEMBL1318876;
ChemSpider	10297844 ;
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

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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]

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]

References

^ ^a ^b ^c Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (2016). "A review on Synthesis of Aminoacetanilides". Journal of Integrated Science and Technology. 4: 111–120. ISSN 2321-4635 – via Google Scholar.
^ Mulyono; Takenaka, Shinji; Sasano, Yasuhiro; Murakami, Shuichiro; Aoki, Kenji (February 2007). "Bacillus cereus strain 10-L-2 produces two arylamine N-acetyltransferases that transform 4-phenylenediamine into 4-aminoacetanilide". Journal of Bioscience and Bioengineering. 103 (2): 147–154. doi:10.1263/jbb.103.147. PMID 17368397.
^ 李, 玉涵; 侯, 洁; 王, 越; 吕, 连海 (2009). "催化加氢制备对氨基乙酰苯胺". 染料与染色. 46 (2): 42–45. ISSN 1672-1179.
^ 曹, 玮; 曲, 波; 梁, 足培 (2004). "对氨基乙酰苯胺合成绿色工艺的研究". 化工时刊 (4): 55–56. ISSN 1002-154X.
^ Gregory, Peter (2000-12-04), "Dyes and Dye Intermediates", in John Wiley & Sons, Inc. (ed.), Kirk-Othmer Encyclopedia of Chemical Technology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 0425051907180507.a01, doi:10.1002/0471238961.0425051907180507.a01, ISBN 978-0-471-23896-6, retrieved 2021-02-07
^ Tahriri, Mozhgan; Yousefi, Mohammad; Mehrani, Kheirollah; Tabatabaee, Masoumeh; Ashkezari, Mahmood Dehghani (August 2017). "Synthesis, Characterization and Antimicrobial Activity of Two Novel Sulfonamide Schiff Base Compounds". Pharmaceutical Chemistry Journal. 51 (5): 425–428. doi:10.1007/s11094-017-1626-z. ISSN 0091-150X. S2CID 25837758.

[:0-1] Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (2016). "A review on Synthesis of Aminoacetanilides". Journal of Integrated Science and Technology. 4: 111–120. ISSN 2321-4635 – via Google Scholar.

[2] Mulyono; Takenaka, Shinji; Sasano, Yasuhiro; Murakami, Shuichiro; Aoki, Kenji (February 2007). "Bacillus cereus strain 10-L-2 produces two arylamine N-acetyltransferases that transform 4-phenylenediamine into 4-aminoacetanilide". Journal of Bioscience and Bioengineering. 103 (2): 147–154. doi:10.1263/jbb.103.147. PMID 17368397.

[3] 李, 玉涵; 侯, 洁; 王, 越; 吕, 连海 (2009). "催化加氢制备对氨基乙酰苯胺". 染料与染色. 46 (2): 42–45. ISSN 1672-1179.

[4] 曹, 玮; 曲, 波; 梁, 足培 (2004). "对氨基乙酰苯胺合成绿色工艺的研究". 化工时刊 (4): 55–56. ISSN 1002-154X.

[5] Gregory, Peter (2000-12-04), "Dyes and Dye Intermediates", in John Wiley & Sons, Inc. (ed.), Kirk-Othmer Encyclopedia of Chemical Technology, Hoboken, NJ, USA: John Wiley & Sons, Inc., pp. 0425051907180507.a01, doi:10.1002/0471238961.0425051907180507.a01, ISBN 978-0-471-23896-6, retrieved 2021-02-07

[6] Tahriri, Mozhgan; Yousefi, Mohammad; Mehrani, Kheirollah; Tabatabaee, Masoumeh; Ashkezari, Mahmood Dehghani (August 2017). "Synthesis, Characterization and Antimicrobial Activity of Two Novel Sulfonamide Schiff Base Compounds". Pharmaceutical Chemistry Journal. 51 (5): 425–428. doi:10.1007/s11094-017-1626-z. ISSN 0091-150X. S2CID 25837758.

[1]