1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

• Catalog No.: A10807
• CAS Number: 25952-53-8
• M. F.: C8H18ClN3
• M. W.: 191.70162
• Purity: 98+%

SYNONYMS

• Title: 1-(3-二甲基氨丙基)-3-乙基碳二酰亚胺, 盐酸盐
• IUPAC name: (3-{[(ethylimino)methylidene]amino}propyl)dimethylamine hydrochloride
• IUPAC Traditional name: (3-{[(ethylimino)methylidene]amino}propyl)dimethylamine hydrochloride
• Synonyms: EDAC; EDCI

DATABASE IDS

• Beilstein Number: 5764110
• EC Number: 247-361-2
• CAS Number: 25952-53-8
• MDL Number: MFCD00012503

PROPERTIES

• Purity: 98+%
• Melting Point: ca 113°C
• GHS Hazard statements: H315-H319-H335
• European Hazard Symbols: Irritant (Xi)
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Risk Statements: 36/37/38
• RTECS: FF2200000
• Safety Statements: 26-37-60
• Storage Warning: Moisture Sensitive
• TSCA Listed: 是

REFERENCES

• 'Water-soluble carbodiimide', widely used for peptide coupling (see Appendix 6), with the major advantage that excess reagent and the urea by-product can be easily removed by washing with dilute acid or water: J. Org. Chem., 26, 2525 (1961); J. Am. Chem. Soc., 87, 2492 (1965). For discussion of the mechanism of peptide coupling with this reagent, see: J. Am. Chem. Soc., 103, 7090 (1981).
• Often used in conjunction with an additive such as HOBt (1-hydroxybenzotriazole hydrate) to suppress racemization; see, for example: Bull. Chem. Soc. Jpn., 55, 2165 (1982). A two-phase solvent system (dichloromethane-water or isopropyl acetate-water) has been found to give superior results in this type of peptide coupling: J. Org. Chem., 60, 3569 (1995). In a comparative study, submolar quantities HOBt in DMF-water gave good results: Chem. Lett., 1 (1997).
• For use in the synthesis of cyclic derivatives of 3'-amino-3'-deoxyadenosine-5'-di- and triphosphates, see: Angew. Chem. Int. Ed., 33, 1394 (1994).
• Promotes various other N-acylation reactions such as the formation of N-acylsulfonamides from primary sulfonamides and N-protected amino acids in the presence of DMAP: Synlett, 1141 (1995).
• For use in the acylation of phosphoranes, see (Cyanomethyl)triphenylphosphonium chloride, A13096.