4-Iodo-N,N-dimethylaniline

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4-Iodo-N,N-dimethylaniline
Names
Preferred IUPAC name
4-Iodo-N,N-dimethylaniline
Other names
N,N-Dimethyl-4-iodoaniline
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C8H10IN/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,1-2H3
    Key: QYOPPZJZMFMBDN-UHFFFAOYSA-N
  • Ic1ccc(N(C)C)cc1
Properties
C8H10IN
Molar mass 247.079 g·mol−1
Appearance dark blue to purple solid [1]
Density 1.652 g/cm3[2]
Boiling point 263.7 °C (506.7 °F; 536.8 K)
34.64 mg/L
Vapor pressure 2 mmHg
Hazards
GHS labelling:
GHS08: Health hazard GHS09: Environmental hazard
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
2
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  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.
  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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