Allessan® CAP
CAS Number: 68957-94-8
Empirical formula: C9H21O6P3
Chemical name: 1-PROPANEPHOSPHONIC ANHYDRIDE
Weight: 318,181
An outstanding coupling and water-removal reagent
Allessan®CAP is an outstanding coupling and water removal reagent, offering numerous advantages over many other commonly used but hazardous coupling reagents such as DCC (toxic), HOBt (explosive), HBTU, and PyBOP.
Safe handling – no CMR properties, non-toxic, non-allergenic, non-sensitizing
Excellent safety profile: high thermal stability, no decomposition
Broad functional group tolerance, mild reaction conditions (0 –25 °C)
Well established at large-scale for challenging liquid phase amide/peptide coupling reactions
Low epimerization, no additives required
Excellent selectivity, high chemical and optical purity, high product purities, and excellent yields
Easy purification/workup due to water-soluble by-products, no need of further purifications
Simple product isolation by liquid/liquid extraction and phase separation
Reduced overall process costs
Long shelf life (> 36 months)
No special storage required
Allessan®CAP can be used for:
- Amidations and Peptide couplings in the liquid phase (linear and cyclic peptides)
- Esterifications
- Functional Group Transformation (nitrile formation, olefine formation, alcohol oxidation, reduction of carboxylic acids, Lossen rearrangement, Beckmann rearrangement)
- Synthesis of heterocyclic compounds (pyrazolone, indole, quinolines, coumarins)
- Swern-type oxidations as a substitute of oxalyl dichloride and triethylamine
- Aza-Diels-Alder reactions as a catalyst
- pH neutral dehydration reagent, similar in strength to the highly reactive and hazardous phosphorous pentoxide and polyphosphoric acid
- Alternative to molecular sieves for water removal from organic solvents
- Lewis acid catalysis
|
Coupling Reagent |
Toxicity |
Epimirization |
Yield |
Purification |
Costs |
|
PPA |
No |
Low |
High |
Simple |
Medium |
|
DCC |
High |
High |
Low |
Very difficult |
Low |
|
DCC/HOBt |
High |
Medium |
Medium |
Very difficult |
Low |
|
EDC |
High |
Medium |
Medium |
Simple |
Medium |
|
BOP |
Very high |
Low |
High |
Difficult |
High |
|
PyClop |
Medium |
Low |
High |
Difficult |
Very high |
|
TBTU/HBTU |
Medium |
Low |
High |
Difficult |
Medium |
|
Coupling Reagent |
Racemization (%) |
Yield (%) |
|
PPA |
1.8 |
86.6 |
|
HOBt/DCC |
5.9 |
60.5 |
|
HOBt/EDC |
11.1 |
67.3 |
|
HOAt/DCC |
11.6 |
N/A |
|
PyBOP |
14.2 |
63.4 |
|
HBTU |
16.1 |
65.6 |
|
HATU |
21.1 |
N/A |
Facility
- Produced in an ISO 9001 certified facility
- Capacity: several hundred tons per year
Variety of Solvents
- Allessan®CAP is typically offered as a concentrated 50% (w/w) solution in various kinds of solvents.
- Ethyl acetate and THF are the most widely used, however, Allessan®CAP can be available in many other solvents (DMF, 2-Me-THF, Acetonitrile, Dichloromethane, Toluene)
Packaging
- 5 L, 50 L, 200 L steel drums with PE inliners or twin-lock drums (DMF)
- Only 5 L drums are allowed to be shipped by air freight
|
|
ALLESSAN®CAP |
|
Name |
PPAA (Propanephosphonic acid anhydride), also shortened to PPA (Polyphosphoric acid) or T3P |
|
Empirical formula |
[C3 H7 O2 P]3 |
|
Molecular weight (g/mol) |
318.18 |
|
CAS No. |
68957-94-8 |
|
Appearance |
Clear solution |
|
Active content (%w/w) |
Min. 50 |
|
Solvent content (%w/w) |
40 - 44.5 |
|
Content of solvent-free Allessan®CAP* (%w/w) |
55.5 - 60 |
|
Hydrogen chloride content of Allessan®CAP solution (%) |
< 0.1 |
*Content of solvent free Allessan®CAP = 100 – solvent content
