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043278

043278-1g



Ethyl (Hydroxyimino)cyanoacetate


CAS Number: 3849-21-6
   
Molecular Formula: C5H6N2O3
   
Molecular Weight: 142.12
   
MDL Number: MFCD00002112


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043278-1g
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Purity:98%
Mp:130-132°
 
Pictograms:
Signal Word:Warning
Hazard Statements:H302, H312, H315, H319, H332, H335
Precautionary Statements:P261, P301 + P312, P302 + P352, P304 + P340, P305 + P351 + P338
Safety Statements:22-24/25
SDS: See MSDS
 

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A coupling reagent for peptide synthesis whose coupling efficiency in solid and liquid phase peptide coupling is superior to HOBt, and at least comparable to HOAt 1. Has a remarkable capacity to inhibit racemization as an additive in carbodiimide mediated amide bond formation 2Also used in resin-to-resin acyl- and aminoacyl-transfer reactions as oxime supports 3.
Advantages of ethyl (hydroxyimino)cyanoacetate include 2: non-explosive replacement for HOBt and HOAt;outperforms HOAt in sterically demanding peptide bond formation;suitable for carbodiimide mediated peptide coupling; less epimerization than HOBt in fragment condensation reactions.

1. Chem.–Eur. J. 2009, 15, 9394
2. Chem.–Eur. J. 2009, 15, 9404
3. J. Am. Chem. Soc.1999, 121, 1636

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