Thioquinanthrene

Thioquinanthrene, also known as thiochinathren, is an aromatic organic chemical compound. It has the chemical formula C₁₈H₁₀N₂S₂ and reacts with alcoholates or alkoxides.^[1] One of the key uses is to act as a catalyst poison in the Rosenmund reduction.^[2][3] It has the IUPAC name of 2,13-dithia-10,21-diazapentacyclo[12.8.0.0^3,12.0^4,9.0^15,20]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene.^[4]

Thioquinanthrene

Names
IUPAC name 2,13-Dithia-10,21-diazapentacyclo[12.8.0.03,12.04,9.015,20]docosa-1(14),3(12),4,6,8,10,15,17,19,21-decaene
Other names Thiochinathren
Identifiers
CAS Number	50634-27-0 N
3D model (JSmol)	Interactive image
ChemSpider	9046144
PubChem CID	10870863
InChI InChI=1S/C18H10N2S2/c1-3-7-13-11(5-1)17-15(9-19-13)22-18-12-6-2-4-8-14(12)20-10-16(18)21-17/h1-10H Key: KZQKWVYWXKNYAO-UHFFFAOYSA-N
SMILES C1=CC=C2C(=C1)C3=C(C=N2)SC4=C(S3)C=NC5=CC=CC=C54
Properties
Chemical formula	C18H10N2S2
Molar mass	318.41 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Rosenmund catalyst poison

In the Rosenmeund reaction, an acid chloride is reduced to an aldehyde. Continuing the reduction produces an alcohol. This further reaction is undesirable as the alcohol will now react with the acyl chloride to produce the unwanted ester product. For this reaction (over reduction) to be prevented, the catalyst needs to be poisoned. Thioquinanthrene was used initially, although other materials have been used since.^[5][6][7][8]