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

CAS Number
25952-53-8
Synonyms
EDAC
EDCI

Stock No. Size Price ($) Quantity Availability
A10807-03 1g 22.50
A10807-06 5g 56.80
A10807-14 25g 194.00
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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°
Storage & Sensitivity
Keep Cold. Moisture Sensitive.
Solubility
Soluble in acetonitrile dichloromethane, dimethylformamide, and tetrahydrofuran. Slightly soluble in water.

Applications

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is used as a carboxyl activating agent. It is used in peptide synthesis, 3'-amino-3'-deoxyadenosine-5'-di- and triphosphates and in the preparation of antibodies like immunoconjugates. It plays a vital role for immobilization of large biomolecules in association with N-hydroxysuccinimide. It is also used in the acylation of phosphoranes.

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: H302-H315-H317-H319

Harmful if swallowed. Causes skin irritation. May cause an allergic skin reaction. Causes serious eye irritation.

Precautionary Statements: P261-P264b-P270-P272-P280-P301+P312-P302+P352-P305+P351+P338-P330-P333+P313-P337+P313-P362-P501c

Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Contaminated work clothing should not be allowed out of the workplace. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Rinse mouth. If skin irritation or rash occurs: Get medical advice/attention. If eye irritation persists: Take off contaminated clothing and wash before reuse. Dispose of contents/ container to an approved waste disposal plant

Other References

Beilstein
5764110
Hazard Class
9
Packing Group
III
Harmonized Tariff Code
2925.19
TSCA
Yes
RTECS
FF2200000

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