4-Iodo-N,N-dimethylaniline

4-Iodo-N,N-dimethylaniline
Names
	Preferred IUPAC name 4-Iodo-N,N-dimethylaniline
	Other names N,N-Dimethyl-4-iodoaniline
Identifiers
CAS Number	698-70-4;
3D model (JSmol)	Interactive image;
ChemSpider	120299;
PubChem CID	136531;
UNII	K6X9S6FT68 ;
CompTox Dashboard (EPA)	DTXSID00220100 ;
	InChI InChI=1S/C8H10IN/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,1-2H3 Key: QYOPPZJZMFMBDN-UHFFFAOYSA-N;
	SMILES Ic1ccc(N(C)C)cc1;
Properties
Chemical formula	C8H10IN
Molar mass	247.079 g·mol−1
Appearance	dark blue to purple solid
Density	1.652 g/cm3
Boiling point	263.7 °C (506.7 °F; 536.8 K)
Solubility in water	34.64 mg/L
Vapor pressure	2 mmHg
Hazards
	GHS labelling:
Pictograms
NFPA 704 (fire diamond)	3 2 0
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

4-Iodo-N,N-dimethylaniline, usually called 4-iododimethylaniline, is an organic compound with the formula IC₆H₄N(CH₃)₂. It is a dark blue to purple solid. The compound is used to attach the dimethylanilinyl group to other substrates.

Synthesis

4-Iodo-dimethylaniline is prepared by iodination of dimethylaniline.^[3]

C₆H₅NMe₂ + I₂ → I:C₆H₄NMe₂ + HI

The iodination is so efficient that it has been recommended for quantifying the presence of iodine.^[4]

References

^ SDS from LGC Standards https://www.lgcstandards.com/DE/de/4-Iodo-N-N-dimethylaniline/p/TRC-I719595-100MG last checked 24.11.2023
^ ACDLabs. "N,N-Dimethyl-4-iodoaniline". ChemSpider.
^ Boothe, Richard; Dial, Christopher; Conaway, Richard; Pagnl, Richard M.; Kabalka, George W. (1986). "The iodination of aromatic substrates on alumina". Tetrahedron Letters. 27 (20): 2207–10. doi:10.1016/S0040-4039(00)84488-3.
^ Mishra S, Singh V, Jain A, Verma K. K. "Determination of iodide by derivatization to 4-iodo-N,N-dimethylaniline and gas chromatography-mass spectrometry" Analyst. 2000, vol. 125, p. 459-64.

[1] SDS from LGC Standards https://www.lgcstandards.com/DE/de/4-Iodo-N-N-dimethylaniline/p/TRC-I719595-100MG last checked 24.11.2023

[2] ACDLabs. "N,N-Dimethyl-4-iodoaniline". ChemSpider.

[DoiS-3] Boothe, Richard; Dial, Christopher; Conaway, Richard; Pagnl, Richard M.; Kabalka, George W. (1986). "The iodination of aromatic substrates on alumina". Tetrahedron Letters. 27 (20): 2207–10. doi:10.1016/S0040-4039(00)84488-3.

[4] Mishra S, Singh V, Jain A, Verma K. K. "Determination of iodide by derivatization to 4-iodo-N,N-dimethylaniline and gas chromatography-mass spectrometry" Analyst. 2000, vol. 125, p. 459-64.

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