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| | Di-tert-butyl iminodicarboxylate Chemical Properties |
| Melting point | 114-117 °C(lit.) | | Boiling point | 273.8±9.0 °C(Predicted) | | density | 1.037±0.06 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | Chloroform, Methanol | | pka | 8.25±0.46(Predicted) | | form | Crystalline Powder | | color | White to beige | | Water Solubility | Insoluble in water. | | Sensitive | Air & Light Sensitive | | BRN | 1911172 | | 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) | | InChIKey | XCAQIUOFDMREBA-UHFFFAOYSA-N | | SMILES | C(C)(C)(C)OC(=O)NC(=O)OC(C)(C)C | | CAS DataBase Reference | 51779-32-9(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-37/39 | | WGK Germany | 3 | | Hazard Note | Irritant | | HS Code | 29241990 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | Di-tert-butyl iminodicarboxylate Usage And Synthesis |
| Synthesis | 
A solution of DMAP (0.61 g, 5.0 mmol) in MeCN (15 ml) was slowly added to a solution of formamide (2.5 g, 56 mmol) and Boc2O (24 g, 110 mol) in MeCN (15 ml). After stirring at room temperature for 4 h, the yellow solution was cooled to 0 °C, and N,N-diethylethylenediamine (6.97 g, 60 mmol) was slowly added at 0 °C. The resulting mixture was stirred at room temperature for 12 h and filtered through a silica mat; the resulting mixture was then filtered at room temperature. The solvent was then evaporated under reduced pressure. The crude product was purified by silica gel chromatography, eluted with EtOAc/hexane (1:5) to give the title product as a white solid (10.99 g, 92%). | | Uses | 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.
| | Chemical Properties | White to beige crystalline powder | | Uses | Di-tert-butyl iminodicarboxylate is a protected amine group that is used to prepare conformationally constrained spirocycles as CCR1 antagonists. |
| | Di-tert-butyl iminodicarboxylate Preparation Products And Raw materials |
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