A10807 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 98+%

CAS Number
25952-53-8
Synonyms
EDAC
EDCI

Size Price ($) Quantity Availability
1g 19.35
5g 54.28
25g 180.86
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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 98+%

MDL
MFCD00012503
EINECS
247-361-2

Chemical Properties

Formula
C8H17N3•HCl
Formula Weight
191.70
Melting point
ca 113°
Sensitivity
Moisture Sensitive
Solubility
Soluble in acetonitrile dichloromethane, dimethylformamide, and tetrahydrofuran. Slightly soluble in water.

Notes

Sensitive to moisture. Incompatible with strong acids, strong oxidizing agents and moisture.

Literature 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.

Liu, J. A.; Guo, X. P.; Liang, S.; An, F.; Shen, H. Y.; Xu, Y. J. Regioselective synthesis of 5'-amino acid esters of some nucleosides via orthogonal protecting protocol. Tetrahedron 2015, 71 (9), 1409-1412.

Meng, H.; Zheng, J.; Wen, X.; Cai, Z.; Zhang, J.; Chen, T. pH- and Sugar-Induced Shape Memory Hydrogel Based on Reversible Phenylboronic Acid-Diol Ester Bonds. Macromol. Rapid Commun. 2015, 36 (6), 533-537.

GHS Hazard and Precautionary Statements

Hazard Statements: H315-H319-H335

Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.

Precautionary Statements: P261-P280-P305+P351+P338-P304+P340-P405-P501a

Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Beilstein
5764110
Harmonized Tariff Code
2925.19
TSCA
Yes
RTECS
FF2200000

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