5-Methyl-2-((2-nitrophenyl)amino)-3-thiophenecarbonitrile

5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
Names
	Preferred IUPAC name 5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile
	Other names ROY
Identifiers
CAS Number	138564-59-7 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1990114 ;
ChemSpider	350550 ;
ECHA InfoCard	100.101.989
PubChem CID	395460;
UNII	J7X181M78Y ;
CompTox Dashboard (EPA)	DTXSID40160713 ;
	InChI InChI=1S/C12H9N3O2S/c1-8-6-9(7-13)12(18-8)14-10-4-2-3-5-11(10)15(16)17/h2-6,14H,1H3 Key: NPXUFPFFHANGDL-UHFFFAOYSA-N ;
	SMILES Cc1cc(c(s1)Nc2ccccc2[N+](=O)[O-])C#N;
Properties
Chemical formula	C12H9N3O2S
Molar mass	259.28 g·mol−1
Melting point	99–102 °C (210–216 °F; 372–375 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H410
Precautionary statements	P273, P391, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile, also known as ROY (red-orange-yellow), is an organic compound which is a chemical intermediate to the drug olanzapine. It has been the subject of intensive study because it can exist in multiple well-characterised crystalline polymorphic forms.^[3]^[4]^[5]^[6]

^ US patent 5817655, Chakrabarti, J.K.; Hotten, T.M. & Tupper, D.E., "Methods of treatment using a thieno-benzodiazepine", issued 1998-10-06, assigned to Eli Lilly and Co. Ltd.
^ "5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-05-08.
^ Krämer, Katrina (2020-07-29). "Red–orange–yellow reclaims polymorph record with help from molecular cousin". chemistryworld.com. Retrieved 2021-05-07.
^ Yu, Lian (2010). "Polymorphism in Molecular Solids: An Extraordinary System of Red, Orange, and Yellow Crystals". Accounts of Chemical Research. 43 (9): 1257–1266. doi:10.1021/ar100040r. PMID 20560545.
^ Li, Xizhen; Ou, Xiao; Rong, Haowei; Huang, Siyong; Nyman, Jonas; Yu, Lian; Lu, Ming (2020). "The Twelfth Solved Structure of ROY: Single Crystals of Y04 Grown from Melt Microdroplets". Crystal Growth & Design. 20 (11): 7093–7097. doi:10.1021/acs.cgd.0c01017. S2CID 225294672.
^ Tyler, Andrew R.; Ragbirsingh, Ronnie; McMonagle, Charles J.; Waddell, Paul G.; Heaps, Sarah E.; Steed, Jonathan W.; Thaw, Paul; Hall, Michael J.; Probert, Michael R. (2020). "Encapsulated Nanodroplet Crystallization of Organic-Soluble Small Molecules". Chem. 6 (7): 1755–1765. doi:10.1016/j.chempr.2020.04.009. PMC 7357602. PMID 32685768.

[US5817655-1] US patent 5817655, Chakrabarti, J.K.; Hotten, T.M. & Tupper, D.E., "Methods of treatment using a thieno-benzodiazepine", issued 1998-10-06, assigned to Eli Lilly and Co. Ltd.

[pubchem-2] "5-Methyl-2-[(2-nitrophenyl)amino]-3-thiophenecarbonitrile". pubchem.ncbi.nlm.nih.gov. Retrieved 2021-05-08.

[Chemworld-3] Krämer, Katrina (2020-07-29). "Red–orange–yellow reclaims polymorph record with help from molecular cousin". chemistryworld.com. Retrieved 2021-05-07.

[pmid20560545-4] Yu, Lian (2010). "Polymorphism in Molecular Solids: An Extraordinary System of Red, Orange, and Yellow Crystals". Accounts of Chemical Research. 43 (9): 1257–1266. doi:10.1021/ar100040r. PMID 20560545.

[5] Li, Xizhen; Ou, Xiao; Rong, Haowei; Huang, Siyong; Nyman, Jonas; Yu, Lian; Lu, Ming (2020). "The Twelfth Solved Structure of ROY: Single Crystals of Y04 Grown from Melt Microdroplets". Crystal Growth & Design. 20 (11): 7093–7097. doi:10.1021/acs.cgd.0c01017. S2CID 225294672.

[Hall-6] Tyler, Andrew R.; Ragbirsingh, Ronnie; McMonagle, Charles J.; Waddell, Paul G.; Heaps, Sarah E.; Steed, Jonathan W.; Thaw, Paul; Hall, Michael J.; Probert, Michael R. (2020). "Encapsulated Nanodroplet Crystallization of Organic-Soluble Small Molecules". Chem. 6 (7): 1755–1765. doi:10.1016/j.chempr.2020.04.009. PMC 7357602. PMID 32685768.

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