N,N'-Diisopropylcarbodiimide

N,N-Diisopropylcarbodiimide is a carbodiimide used in peptide synthesis. As a liquid, it is easier to handle than the commonly used N,N-dicyclohexylcarbodiimide, a waxy solid. In addition, N,N-diisopropylurea, the byproduct of its use in many chemical reactions, is soluble in most organic solvents, a property that facilitates work-up.

N,N-Diisopropylcarbodiimide
Names
Preferred IUPAC name
N,N’-Di(propan-2-yl)methanediimine
Other names
Diisopropylmethanediimine
Identifiers
3D model (JSmol)
Abbreviations DIC, DIPC
878281
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.677
EC Number
  • 211-743-7
101400
UNII
Properties
C7H14N2
Molar mass 126.203 g·mol−1
Appearance Liquid
Density 0.806 g/mL
Boiling point 145 to 148 °C (293 to 298 °F; 418 to 421 K)
Hazards
Safety data sheet External MSDS
GHS pictograms
GHS Signal word Danger
H226, H315, H317, H318, H330, H334
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P285, P302+352, P303+361+353, P304+340, P304+341, P305+351+338, P310, P312, P320, P321, P332+313, P333+313
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Further reading

  • Angell, Y (1994). "Comparative studies of the coupling of N-methylated, sterically hindered amino acids during solid-phase peptide synthesis". Tetrahedron Lett. 35 (33): 5981–5984. doi:10.1016/0040-4039(94)88054-9.
  • Izdebski, JAN; Orlowska, Alicja; Anulewicz, Romana; Witkowska, EWA; Fiertek, Dariusz (1994). "Reinvestigation of the reactions of carbodiimides with alkoxycarbonylamino acid symmetrical anhydrides : Isolation of two N'-acylureas". Int. J. Pept. Protein Res. 43 (2): 184–9. doi:10.1111/j.1399-3011.1994.tb00521.x. PMID 8200738.


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