Di-tert-butyl dicarbonate
SIAL/34660 - ≥98.0% (GC)
Synonym: Boc2O; Boc anhydride; Di-tert-butyl pyrocarbonate
CAS Number: 24424-99-5
Empirical Formula (Hill Notation): C10H18O5
Molecular Weight: 218.25
EC Number: 246-240-1
MDL Number: MFCD00008805
Linear Formula: [(CH3)3COCO]2O
Product Type: Chemical
| application(s) | peptide synthesis |
| assay | ≥98.0% (GC) |
| bp | 56-57 °C/0.5 mmHg (lit.) |
| density | 0.95 g/mL at 25 °C (lit.) |
| form | solid or liquid |
| InChI | 1S/C10H18O5/c1-9(2,3)14-7 |
| InChI key | DYHSDKLCOJIUFX-UHFFFAOYSA |
| mp | 23 °C (lit.) |
| Quality Level | 200  |
| refractive index | n |
| SMILES string | CC(C)(C)OC(=O)OC(=O)OC(C) |
| storage temp. | 2-8°C |
| Application: | Di-tert-butyl dicarbonate (Boc2O) has been used in the synthesis of: • An azobenzene amino acid(aa). • N-tert-butoxycarbonyl-3,4-methy 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-methy • 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. |
| Application: | Reagent for the introduction of the Boc protecting group. |
| General description: | 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. |
| Packaging: | 25, 100, 500 g in poly bottle |
| Warning: | Hydrolyzes to t-butanol and CO2; causes internal pressure in bottle if exposed to moisture. |
| Symbol |    GHS02,GHS05,GHS06 |
| Signal word | Danger |
| Hazard statements | H226 - H315 - H317 - H318 - H330 - H335 |
| Precautionary statements | P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338 |
| Hazard Codes | T+ |
| Risk Statements | 10-26-36/37/38-43 |
| Safety Statements | 7/9-16-26-28-36/37/39-45 |
| 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 |
| Purity | ≥98.0% (GC) |
| bp | 56-57 °C/0.5 mmHg (lit.) |
| mp | 23 °C (lit.) |
| Density | 0.95 g/mL at 25 °C (lit.) |
| Refractive Index | n |
| Storage Temp. | 2-8°C |
| UNSPSC | 12352108 |