32596
Diallyl pyrocarbonate
≥95.0% (T)
Synonym(s):
(Alloc)2O, Diallyl dicarbonate
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About This Item
Linear Formula:
(CH2=CHCH2OCO)2O
CAS Number:
Molecular Weight:
186.16
PubChem Substance ID:
UNSPSC Code:
12352108
Beilstein/REAXYS Number:
4390381
MDL number:
SMILES string
C=CCOC(=O)OC(=O)OCC=C
InChI
1S/C8H10O5/c1-3-5-11-7(9)13-8(10)12-6-4-2/h3-4H,1-2,5-6H2
InChI key
XVSSGIXTKVRGAR-UHFFFAOYSA-N
assay
≥95.0% (T)
bp
60 °C/0.05 mmHg (lit.)
density
1.121 g/mL at 25 °C (lit.)
application(s)
peptide synthesis
storage temp.
2-8°C
General description
Diallyl pyrocarbonate or (Alloc)2O is used as a reagent for the introduction of allyloxycarbonyl (Alloc or Aloc) protecting group to primary and secondary amines. In peptide synthesis, it is also used to protect amino acid functional groups due to its stability to the acidic and basic conditions. Various amino functional groups such as amino sugars and nucleosides are also protected by using diallyldicarbonate reagent.
Other Notes
Reagent for the convenient introduction of the N-allyloxycarbonyl (N-Alloc) amino protection ; Allyl carbamate protections can be readily cleaved by palladium(0) reagents.
wgk
WGK 3
Storage Class
10 - Combustible liquids
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
target_organs
Respiratory system
flash_point_f
201.2 °F - closed cup
flash_point_c
94 °C - closed cup
ppe
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Regulatory Information
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G. Sennyey et al.
Tetrahedron Letters, 28, 5809-5809 (1987)
H. Kunz et al.
Angewandte Chemie (International Edition in English), 96, 426-426 (1984)
Diallyl dicarbonate. A convenient reagent for the synthesis of allyl carbamates.
Barcelo G, et al.
Tetrahedron Letters, 28(47), 5809-5810 (1987)
O. Dangles et al.
The Journal of Organic Chemistry, 52, 4984-4984 (1987)
N-[(Allyloxycarbonyl) oxy] maleimide-styrene Copolymer
N Carmen, et al.
Encyclopedia of Reagents for Organic Synthesis, Second Edition, 1-2 (2001)
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