4-Fluoroaniline

4-Fluoroaniline

Names
Other names p-Fluoroaniline
Identifiers
CAS Number	371-40-4  Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28546
ChEMBL	ChEMBL32014
ChemSpider	9349
ECHA InfoCard	100.006.123
EC Number	206-735-5
KEGG	C11014
PubChem CID	9731
UNII	60HI1G076Z
UN number	2941
CompTox Dashboard (EPA)	DTXSID9022027
InChI InChI=1S/C6H6FN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2 Key: KRZCOLNOCZKSDF-UHFFFAOYSA-N
SMILES C1=CC(=CC=C1N)F
Properties
Chemical formula	C6H6FN
Molar mass	111.119 g·mol−1
Appearance	colorless liquid
Density	1.1725 g/cm3
Melting point	−1.9 °C (28.6 °F; 271.2 K)
Boiling point	188 °C (370 °F; 461 K)
Hazards
GHS labelling: [1]
Pictograms
Signal word	Danger
Hazard statements	H302, H312, H314, H315, H317, H319, H332, H372, H373, H410, H411
Precautionary statements	P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P313, P337+P317, P362+P364, P363, P391, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Fluoroaniline is an organofluorine compound with the formula FC₆H₄NH₂. A colorless liquid, it is one of three isomers of fluoroaniline. 4-Fluoroaniline can be prepared by the hydrogenation of 4-nitrofluorobenzene. ^[2]

It is a common building block in medicinal chemistry and related fields. ^[3] For example, it is a precursor to the fungicide fluoroimide  [ de ] or the fentanyl analogue parafluorofentanyl. It has also been evaluated for the production of ligands for homogeneous catalysis. ^[4]

References

1. "4-Fluoroaniline". pubchem.ncbi.nlm.nih.gov.
2. Jagadeesh, Rajenahally V.; Surkus, Annette-Enrica; Junge, Henrik; Pohl, Marga-Martina; Radnik, Jörg; Rabeah, Jabor; Huan, Heming; Schünemann, Volker; Brückner, Angelika; Beller, Matthias (2013). "Nanoscale Fe₂O₃-Based Catalysts for Selective Hydrogenation of Nitroarenes to Anilines". Science. 342 (6162): 1073–1076. Bibcode:2013Sci...342.1073J. doi:10.1126/science.1242005. PMID   24288327. S2CID   11780985.
3. Wei, Jinbao; Chen, Jinghong; Ju, Peijun; Ma, Le; Chen, Li; Ma, Weidong; Zheng, Tao; Yang, Guangyi; Wang, Yong-Xiang (2019). "Synthesis and Biological Evaluation of 4β-N-Acetylamino Substituted Podophyllotoxin Derivatives as Novel Anticancer Agents". Frontiers in Chemistry. 7: 253. Bibcode:2019FrCh....7..253W. doi: 10.3389/fchem.2019.00253 . PMC   6491884 . PMID   31106192.
4. Mitani, Makoto; Mohri, Jun-Ichi; Yoshida, Yasunori; Saito, Junji; Ishii, Seiichi; Tsuru, Kazutaka; Matsui, Shigekazu; Furuyama, Rieko; Nakano, Takashi; Tanaka, Hidetsugu; Kojoh, Shin-Ichi; Matsugi, Tomoaki; Kashiwa, Norio; Fujita, Terunori (2002). "Living Polymerization of Ethylene Catalyzed by Titanium Complexes Having Fluorine-Containing Phenoxy−Imine Chelate Ligands". Journal of the American Chemical Society. 124 (13): 3327–3336. doi:10.1021/ja0117581. PMID   11916417.