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Di-tert-butyl-iminodicarboxylate

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Di-tert-butyl-iminodicarboxylate
Names
Preferred IUPAC name Di-tert-butyl 2-imidodicarbonate
Other names HN(Boc)2; Bis-Boc amine
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C10H19NO4/c1-9(2,3)14-7(12)11-8(13)15-10(4,5)6/h1-6H3,(H,11,12,13)Key: XCAQIUOFDMREBA-UHFFFAOYSA-N
SMILES
  • CC(C)(C)OC(=O)NC(=O)OC(C)(C)C
Properties
Chemical formula C10H19NO4
Molar mass 217.265 g·mol
Appearance White solid
Melting point 119–121 °C (246–250 °F; 392–394 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula 2NH. It is a white solid that is soluble in organic solvents. The compound is used as a reagent for the preparation of primary amines from alkyl halides. It was popularized as an alternative to the Gabriel synthesis for the same conversion. Amines can also be prepared from alcohols by dehydration using the Mitsunobu reaction.

In the usual implementation the reagent is deprotonated to give the potassium salt, which is N-alkylated. The Boc protecting groups are subsequently removed under acidic conditions.

References

  1. Ulf Ragnarsson; Leif Grehn (1991). "Novel Gabriel Reagents". Acc. Chem. Res. 24 (10): 285–289. doi:10.1021/ar00010a001.
  2. Neelamkavil, Santhosh "Di-tert-butyl-imidocarbonate" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. doi:10.1002/047084289X.rn00488
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