Diisopropylcarbodiimide

Structural formula
General
Surname	Diisopropylcarbodiimide
other names	DIC Diisopropylcarbodiimide
Molecular formula	C 7 H 14 N 2
Brief description	colorless liquid
External identifiers / databases
CAS number 693-13-0 EC number 211-743-7 ECHA InfoCard 100.010.677 PubChem 12734 Wikidata Q408747
properties
Molar mass	126.20 g mol −1
Physical state	liquid
density	0.815 g cm −3
boiling point	145-148 ° C
Refractive index	1.433 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 226-315-317-318-330-334-335 P: 260-280-284-305 + 351 + 338-310
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

N, N'-Diisopropylcarbodiimide ( DIC ) is a carbodiimide and is used as a coupling reagent in peptide synthesis . As a liquid, it is easier to handle than the dicyclohexylcarbodiimide , which is also used for this purpose . The connection is thermally unstable. A DSC measurement shows a strongly exothermic decomposition reaction from 252 ° C with an exothermicity of −410 kJ kg ⁻¹ or −51.7 kJ mol ⁻¹ .

Diisopropylcarbodiimide serves as an activating reagent in the peptide coupling by forming what is known as an active ester during the reaction with the carboxylic acid function, which then reacts with an amino group to form the amide (peptide bond). Furthermore, it binds the water formally formed during the reaction irreversibly, the product being diisopropylurea . DIC is used in peptide synthesis in dissolved form (solution-phase method) as well as in bound solid-phase synthesis (solid-phase method).

literature

• WC Chan, PD White: Fmoc Solid Phase Peptide Synthesis. Reprint 2004, Oxford University Press, ISBN 0-19-963724-5 .

Individual evidence

1. ↑ ^{a b c d e f} DIC data sheet at Sigma-Aldrich , accessed on May 12, 2017 ( PDF ).
2. ↑ Sperry, JB; Minteer, CJ; Tao, J .; Johnson, R .; Duzguner, R .; Hawksworth, M .; Oke, S .; Richardson, PF; Barnhart, R .; Bill, DR; Giusto, RA; Weaver, JD: Thermal Stability Assessment of Peptide Coupling Reagents Commonly Used in Pharmaceutical Manufacturing in Org. Process Res. Dev. 22 (2018) 1262-1275, doi : 10.1021 / acs.oprd.8b00193 .