Di-tert-butyl dicarbonate
Empirical Formula (Hill Notation): | C10H18O5 |
Linear Formula: | [(CH3)3COCO]2O |
CAS Number: | 24424-99-5 |
Molecular Weight: | 218.25 |
Beilstein/REAXYS Number: | 1911173 |
EC Number: | 246-240-1 |
MDL number: | MFCD00008805 |
PubChem Substance ID: | 329755051 |
NACRES: | NA.22 |
Кат. номер |
34660-1KG-F |
34660-100G |
34660-500G-F |
34660-25G-F |
34660-100G-F |
34660-VAR-F |
34660-RSAMPLE-F |
34660-6X500G-F |
34660-6X100G-F |
34660-25KG-F |
34660-10KG-F |
Di-
tert-butyl dicarbonate (Boc2O) is a reagent mainly used for the introduction of the Boc protecting group to amine functionalities. It is also used as a dehydrating agent in some organic reactions, particularly with carboxylic acids, certain hydroxyl groups, or with primary nitroalkanes.
Di-
tert-butyl dicarbonate (Boc2O) has been used in the synthesis of:
- An azobenzene amino acid(aa).
- N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-BOC-MDMA) from MDMA.
It can also be used as a reagent:
- To introduce acid-labile Boc-protecting group in amino acids, peptides, and proteins.
- To prepare styrene derivatives by Heck olefination of aromatic carboxylic acids in the presence of a Pd catalyst.
- To synthesize oxazolidin-2-ones and imidazolidin-2-ones by isocyanation of 1,2-aminoalcohols and 1,2-diamines using DMAP as a catalyst.
- In the preparation of N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-Boc-MDMA) from MDMA.
- For the conversion of amines to corresponding isocyanates, carbamates, and urea derivatives.
- In the N-BOC-ylation of amides.
- In the N-BOC-ylation of sensitive compounds under non-aqueous conditions.
Reagent for the introduction of the Boc protecting group.
Packaging
25, 100, 500 g in poly bottle
Warning
Hydrolyzes to
t-butanol and CO2; causes internal pressure in bottle if exposed to moisture.
Quality Level | 200, |
assay | 98.0% (GC) |
application(s) | peptide synthesis: suitable |
refractive index | n20/D 1.409 (lit.) |
bp | 56-57 °C/0.5 mmHg (lit.) |
mp | 23 °C (lit.) |
density | 0.95 g/mL at 25 °C (lit.) |
storage temp. | 2-8°C |
SMILES string | CC(C)(C)OC(=O)OC(=O)OC(C)(C)C |
InChI | 1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3 |
InChI key | DYHSDKLCOJIUFX-UHFFFAOYSA-N |
pictograms | GHS02,GHS05,GHS06 |
signalword | Danger |
hcodes | H226 - H315 - H317 - H318 - H330 - H335 |
pcodes | P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 |
Target Organs | Respiratory system |
Personal Protective Equipment | Eyeshields,, Faceshields,, Gloves,, type ABEK (EN14387) respirator filter, |
RIDADR | UN 2929 3(6.1) / PGII |
WGK Germany | WGK 3 |
Flash Point F | 98.6 °F - closed cup |
Flash Point C | 37 °C - closed cup |