2-Methylindole

2-Methylindole
Names
	Preferred IUPAC name 2-Methyl-1H-indole
Identifiers
CAS Number	95-20-5 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL259419 ;
ChemSpider	6954 ;
ECHA InfoCard	100.002.181
PubChem CID	7224;
UNII	I7CN58827I ;
CompTox Dashboard (EPA)	DTXSID5059117 ;
	InChI InChI=1S/C9H9N/c1-7-6-8-4-2-3-5-9(8)10-7/h2-6,10H,1H3 Key: BHNHHSOHWZKFOX-UHFFFAOYSA-N ;
	SMILES Cc2cc1ccccc1[nH]2;
Properties
Chemical formula	C9H9N
Molar mass	131.178 g·mol−1
Appearance	Yellow viscous liquid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Methylketol or 2-methylindole is a mildly toxic and slightly flammable organic compound which occurs as a white solid which turns brown over time.^[1]^[2] It has chemical formula C₉H₉N.^[3]

Methylketol is used as an intermediate for synthesizing dyes,^[4] pigments,^[5] optical brighteners, and pharmaceuticals.^[6]

^ Brown, Daniel R.; Clark, Bryan W.; Garner, Lindsey V. T.; Di Giulio, Richard T. (June 2015). "Zebrafish cardiotoxicity: the effects of CYP1A inhibition and AHR2 knockdown following exposure to weak aryl hydrocarbon receptor agonists". Environmental Science and Pollution Research International. 22 (11): 8329–8338. Bibcode:2015ESPR...22.8329B. doi:10.1007/s11356-014-3969-2. ISSN 1614-7499. PMC 4442063. PMID 25532870.
^ Brown, D. R.; Clark, B. W.; Garner, L. V. T.; Di Giulio, R. T. (October 2016). "Embryonic cardiotoxicity of weak aryl hydrocarbon receptor agonists and CYP1A inhibitor fluoranthene in the Atlantic killifish (Fundulus heteroclitus)". Comparative Biochemistry and Physiology. Toxicology & Pharmacology. 188: 45–51. doi:10.1016/j.cbpc.2016.05.005. ISSN 1532-0456. PMID 27211013.
^ Parker, Amie; Lamata, Pilar; Viguri, Fernando; Rodríguez, Ricardo; López, José A.; Lahoz, Fernando J.; García-Orduña, Pilar; Carmona, Daniel (2020-10-12). "Half-sandwich complexes of osmium containing guanidine-derived ligands". Dalton Transactions. 49 (39): 13601–13617. doi:10.1039/d0dt02713h. hdl:10261/233133. ISSN 1477-9234. PMID 32975256. S2CID 221913494.
^ Casas-Catalán, María José; Doménech-Carbó, María Teresa (May 2005). "Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation". Analytical and Bioanalytical Chemistry. 382 (2): 259–268. doi:10.1007/s00216-005-3064-0. ISSN 1618-2642. PMID 15782338. S2CID 44407380.
^ Shaki, Hanieh; Gharanjig, Kamaladin; Khosravi, Alireza (July 2015). "Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides". Biotechnology Progress. 31 (4): 1086–1095. doi:10.1002/btpr.2107. ISSN 1520-6033. PMID 25967675. S2CID 25349059.
^ Ozcan-Sezer, Senem; Ince, Elif; Akdemir, Atilla; Ceylan, Özlem Öztürk; Suzen, Sibel; Gurer-Orhan, Hande (May 2019). "Aromatase inhibition by 2-methyl indole hydrazone derivatives evaluated via molecular docking and in vitro activity studies". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 49 (5): 549–556. doi:10.1080/00498254.2018.1482029. ISSN 1366-5928. PMID 29804490. S2CID 44062839.

[1] Brown, Daniel R.; Clark, Bryan W.; Garner, Lindsey V. T.; Di Giulio, Richard T. (June 2015). "Zebrafish cardiotoxicity: the effects of CYP1A inhibition and AHR2 knockdown following exposure to weak aryl hydrocarbon receptor agonists". Environmental Science and Pollution Research International. 22 (11): 8329–8338. Bibcode:2015ESPR...22.8329B. doi:10.1007/s11356-014-3969-2. ISSN 1614-7499. PMC 4442063. PMID 25532870.

[2] Brown, D. R.; Clark, B. W.; Garner, L. V. T.; Di Giulio, R. T. (October 2016). "Embryonic cardiotoxicity of weak aryl hydrocarbon receptor agonists and CYP1A inhibitor fluoranthene in the Atlantic killifish (Fundulus heteroclitus)". Comparative Biochemistry and Physiology. Toxicology & Pharmacology. 188: 45–51. doi:10.1016/j.cbpc.2016.05.005. ISSN 1532-0456. PMID 27211013.

[3] Parker, Amie; Lamata, Pilar; Viguri, Fernando; Rodríguez, Ricardo; López, José A.; Lahoz, Fernando J.; García-Orduña, Pilar; Carmona, Daniel (2020-10-12). "Half-sandwich complexes of osmium containing guanidine-derived ligands". Dalton Transactions. 49 (39): 13601–13617. doi:10.1039/d0dt02713h. hdl:10261/233133. ISSN 1477-9234. PMID 32975256. S2CID 221913494.

[4] Casas-Catalán, María José; Doménech-Carbó, María Teresa (May 2005). "Identification of natural dyes used in works of art by pyrolysis-gas chromatography/mass spectrometry combined with in situ trimethylsilylation". Analytical and Bioanalytical Chemistry. 382 (2): 259–268. doi:10.1007/s00216-005-3064-0. ISSN 1618-2642. PMID 15782338. S2CID 44407380.

[5] Shaki, Hanieh; Gharanjig, Kamaladin; Khosravi, Alireza (July 2015). "Synthesis and investigation of antimicrobial activity and spectrophotometric and dyeing properties of some novel azo disperse dyes based on naphthalimides". Biotechnology Progress. 31 (4): 1086–1095. doi:10.1002/btpr.2107. ISSN 1520-6033. PMID 25967675. S2CID 25349059.

[6] Ozcan-Sezer, Senem; Ince, Elif; Akdemir, Atilla; Ceylan, Özlem Öztürk; Suzen, Sibel; Gurer-Orhan, Hande (May 2019). "Aromatase inhibition by 2-methyl indole hydrazone derivatives evaluated via molecular docking and in vitro activity studies". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 49 (5): 549–556. doi:10.1080/00498254.2018.1482029. ISSN 1366-5928. PMID 29804490. S2CID 44062839.

[1]

[2]

[3]

[4]

[5]

[6]