Di-tert-butyl-iminodicarboxylate

Di-tert-butyl-iminodicarboxylate

Names
Other names HN(Boc)2; Bis-Boc amine
Identifiers
CAS Number	51779-32-9
3D model (JSmol)	Interactive image
ChemSpider	246393
PubChem CID	279800
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	217.27 g·mol−1
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 [77 °F], 100 kPa).
Infobox references

Di-tert-butyl-iminodicarboxylate is an organic compound that can be described with the formula [(CH₃)₃COC(O)]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.