Wikipedia

N,N'-Diisopropylcarbodiimide

N,N′-Diisopropylcarbodiimide is a carbodiimide used in peptide synthesis.[1] [2]As a liquid, it is easier to handle than the commonly used N,N′-dicyclohexylcarbodiimide, a waxy solid. In addition, N,N′-diisopropylurea, its byproduct in many chemical reactions, is soluble in most organic solvents, a property that facilitates work-up.

N,N′-Diisopropylcarbodiimide
Ball-and-stick model of the N,N'-diisopropylcarbodiimide molecule
Names
Preferred IUPAC name
N,N'-Di(propan-2-yl)methanediimine
Other names
Diisopropylmethanediimine, DIC
Identifiers
3D model (JSmol)
Abbreviations DIC, DIPC
878281
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.010.677 Edit this at Wikidata
EC Number
  • 211-743-7
101400
UNII
  • InChI=1S/C7H14N2/c1-6(2)8-5-9-7(3)4/h6-7H,1-4H3 ☒N
    Key: BDNKZNFMNDZQMI-UHFFFAOYSA-N ☒N
  • InChI=1/C7H14N2/c1-6(2)8-5-9-7(3)4/h6-7H,1-4H3
    Key: BDNKZNFMNDZQMI-UHFFFAOYAW
  • CC(C)N=C=NC(C)C
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
GHS labelling:
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS07: Exclamation markGHS08: Health hazard
Danger
H226, H315, H317, H318, H330, H334
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P285, P302+P352, P303+P361+P353, P304+P340, P304+P341, P305+P351+P338, P310, P312, P320, P321, P332+P313, P333+P313, P342+P311, P362, P363, P370+P378, P403+P233, P403+P235, P405, P501
Safety data sheet (SDS) External MSDS
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Safety

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In vivo dermal sensitization studies according to OECD 429[3] confirmed DIC is a strong skin sensitizer, showing a response at 0.20 wt% in the Local Lymph Node Assay (LLNA) placing it in Globally Harmonized System of Classification and Labelling of Chemicals (GHS) Dermal Sensitization Category 1A.[4] Thermal hazard analysis by differential scanning calorimetry (DSC) shows DIC poses minimal explosion risks.[5]


References

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  1. ^ Angell, Yvonne M.; García-Echeverría, Carlos; Rich, Daniel H. (1994-08-15). "Comparative studies of the coupling of N-methylated, sterically hindered amino acids during solid-phase peptide synthesis". Tetrahedron Letters. 35 (33): 5981–5984. doi:10.1016/0040-4039(94)88054-9. ISSN 0040-4039.
  2. ^ 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". International Journal of Peptide and Protein Research. 43 (2): 184–189. doi:10.1111/j.1399-3011.1994.tb00521.x. ISSN 0367-8377.
  3. ^ OECD (2010). Test No. 429: Skin Sensitisation: Local Lymph Node Assay. Paris: Organisation for Economic Co-operation and Development.
  4. ^ Graham, Jessica C.; Trejo-Martin, Alejandra; Chilton, Martyn L.; Kostal, Jakub; Bercu, Joel; Beutner, Gregory L.; Bruen, Uma S.; Dolan, David G.; Gomez, Stephen; Hillegass, Jedd; Nicolette, John; Schmitz, Matthew (2022-06-20). "An Evaluation of the Occupational Health Hazards of Peptide Couplers". Chemical Research in Toxicology. 35 (6): 1011–1022. doi:10.1021/acs.chemrestox.2c00031. ISSN 0893-228X. PMC 9214767. PMID 35532537.
  5. ^ Sperry, Jeffrey B.; Minteer, Christopher J.; Tao, JingYa; Johnson, Rebecca; Duzguner, Remzi; Hawksworth, Michael; Oke, Samantha; Richardson, Paul F.; Barnhart, Richard; Bill, David R.; Giusto, Robert A.; Weaver, John D. (2018-09-21). "Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing". Organic Process Research & Development. 22 (9): 1262–1275. doi:10.1021/acs.oprd.8b00193. ISSN 1083-6160.
 

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