N,N'-Diisopropylcarbodiimide

N,N′-Diisopropylcarbodiimide

Names
Preferred IUPAC name N,N’-Di(propan-2-yl)methanediimine
Other names Diisopropylmethanediimine
Identifiers
CAS Number	693-13-0
3D model (JSmol)	Interactive image
Abbreviations	DIC, DIPC
Beilstein Reference	878281
ChEBI	CHEBI:53092
ChEMBL	ChEMBL1332992
ChemSpider	12211
ECHA InfoCard	100.010.677
EC Number	211-743-7
Gmelin Reference	101400
PubChem CID	12734
UNII	OQO20I6TWH
CompTox Dashboard (EPA)	DTXSID4025086
InChI InChI=1S/C7H14N2/c1-6(2)8-5-9-7(3)4/h6-7H,1-4H3 Key: BDNKZNFMNDZQMI-UHFFFAOYSA-N InChI=1/C7H14N2/c1-6(2)8-5-9-7(3)4/h6-7H,1-4H3 Key: BDNKZNFMNDZQMI-UHFFFAOYAW
SMILES CC(C)N=C=NC(C)C
Properties
Chemical formula	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
GHS hazard statements	H226, H315, H317, H318, H330, H334
GHS precautionary statements	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,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.

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.