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. Automated Boc protection and deprotection can be done using Synple Automated Synthesis Platform (SYNPLE-SC002 ), Boc protection cartridges ((SYNPLE-B001 ), (SYNPLE-B002 ), and Boc deprotection cartridges (SYNPLE-B011 ) |
| 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 |