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009018

009018-5g



BOP


CAS Number: 56602-33-6
   
Molecular Formula: C12H22F6N6OP2
   
Molecular Weight: 442.28
   
MDL Number: MFCD00011948


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009018-5g
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009018-25g
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009018-100g
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009018-500g
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Purity:97%
Mp:>130°(dec.)
 
Pictograms:
Signal Word:Danger
Hazard Statements:H228.1, H302, H315, H317, H319, H335, EUH044
Precautionary Statements:P210, P233, P261, P271, P280, P302 + P352, P304 + P340, P305 + P351 + P338
UN#:UN1325
Packing Group:II
Hazard Class:4.1
SDS: See MSDS
 
Limited Quantities:1.0 Kg (2.2 lbs)
Excepted Quantities:Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

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A reagent commonly used in the synthesis of peptides. A very efficient reagent that allows in situ formation of hydroxybenzotriazolyl esters 1. Its main disadvantage is that the highly toxic and carcinogenic HMPA is formed during the course of the reaction 2,3. BOP allows the efficient in situ traping of the dipeptide amine by the acylating reagent. This specific ability of BOP for avoiding diketopiperazine formation is illustrated in liquid phase synthesis as well as in the SPPS 4. BOP is  also used as a condensing agent to promote internucleotidic bond formation in phosphotriester oligodeoxyribonucleotide synthesis 5,6. A useful coupling agent to synthesis nitriles from aldoximes 7.

1. Tetrahedron Lett. 1996, 37, 4237.
2. Tetrahedron Lett1994, 35, 5603.
3. Ukr. Bio. Acta  2005, 2, 13.
4. Tetrahedron Lett. 1990, 31, 7363.
5. Eur. J. Org. Chem. 2008, 10, 1705. 
6. Ukr. Bio. Acta  2004, 1, 23.
7. J. Org. Chem. 2009, 74, 3079.

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