3-Aminoacetanilide

3-Aminoacetanilide
Names
	Preferred IUPAC name N-(3-Aminophenyl)acetamide
	Other names m-Aminoacetanilide, 3′-Acetamidoaniline, N-Acetyl-1,3-phenylenediamine
	Identifiers
CAS Number	102-28-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1606123;
ChemSpider	7322;
ECHA InfoCard	100.002.747
EC Number	203-021-5;
PubChem CID	7604;
UNII	Q5K7HYS7JJ ;
CompTox Dashboard (EPA)	DTXSID2024454 ;
	InChI InChI=1S/C8H10N2O/c1-6(11)10-8-4-2-3-7(9)5-8/h2-5H,9H2,1H3,(H,10,11) Key: PEMGGJDINLGTON-UHFFFAOYSA-N;
	SMILES C1(=CC=CC(=C1)N([H])[H])N(C(C)=O)[H];
	Properties
Chemical formula	C8H10N2O
Molar mass	150.18 g/mol
Appearance	gray solid
Melting point	86-88
Solubility in water	Soluble in water 1-5 g/100 mL at 24°C.
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H319, H335
Precautionary statements	P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3'-Aminoacetanilide is a chemical compound which is a amino derivative of acetanilide and meta-isomer of aminoacetanilide. There are two other isomers of aminoacetanilide, 2-aminoacetanilide and 4-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]^[2]

Synthesis

A number of methods are available to synthesize 3'-aminoacetanilide.^[2] It could be prepared by reduction of m-nitroacetanilide. m-Chloroacetanilde has been converted into m-aminoacetanilide.^[3]

Uses

3′-Aminoacetanilide has been used in the preparation of azo compounds, pyrrole, imidazole, thiazole and other heterocycles. It is starting material for Trametinib. It is also used to prepare reactive yellow K-RN and dispersed dye.^[4]

References

^ Rück-Braun, Karola; Kempa, Stefan; Priewisch, Beate; Richter, Anja; Seedorff, Sabine; Wallach, Lukas (2009-10-22). "Azobenzene-Based ω-Amino Acids and Related Building Blocks: Synthesis, Properties, and Application in Peptide Chemistry". Synthesis. 2009 (24): s–0029–1217074. doi:10.1055/s-0029-1217074. ISSN 0039-7881.
^ ^a ^b Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (7 June 2016). "A review on Synthesis of Aminoacetanilides". Journal of Integrated Science and Technology. 4: 111–120. ISSN 2321-4635 – via Google Scholar.
^ Pitts, Michael R.; Harrison, Justin R.; Moody, Christopher J. (2001). "Indium metal as a reducing agent in organic synthesis". Journal of the Chemical Society, Perkin Transactions 1 (9): 955–977. doi:10.1039/b101712h.
^ CN 101328133, Qi, Ou; Huaiqing, Gao & Songtao, Ni et al., "Synthetic method of m-amino acetanilide", issued 2008-07-26, assigned to Zhejiang Longsheng Dyestuff Chemicals Co. Ltd.

[1] Rück-Braun, Karola; Kempa, Stefan; Priewisch, Beate; Richter, Anja; Seedorff, Sabine; Wallach, Lukas (2009-10-22). "Azobenzene-Based ω-Amino Acids and Related Building Blocks: Synthesis, Properties, and Application in Peptide Chemistry". Synthesis. 2009 (24): s–0029–1217074. doi:10.1055/s-0029-1217074. ISSN 0039-7881.

[:0-2] Singh, Raman; Kau, Rajneesh; Singh, Kuldeep (7 June 2016). "A review on Synthesis of Aminoacetanilides". Journal of Integrated Science and Technology. 4: 111–120. ISSN 2321-4635 – via Google Scholar.

[3] Pitts, Michael R.; Harrison, Justin R.; Moody, Christopher J. (2001). "Indium metal as a reducing agent in organic synthesis". Journal of the Chemical Society, Perkin Transactions 1 (9): 955–977. doi:10.1039/b101712h.

[4] CN 101328133, Qi, Ou; Huaiqing, Gao & Songtao, Ni et al., "Synthetic method of m-amino acetanilide", issued 2008-07-26, assigned to Zhejiang Longsheng Dyestuff Chemicals Co. Ltd.

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