34660

Di-tert-butyl dicarbonate

≥98.0% (GC), for peptide synthesis

• Sinonimo/i: Boc₂O, Boc anhydride, Di-tert-butyl pyrocarbonate
• Formula condensata: [(CH₃)₃COCO]₂O
• Numero CAS: 24424-99-5
• Peso molecolare: 218.25
• Beilstein: 1911173
• Numero CE: 246-240-1
• Numero MDL: MFCD00008805
• Codice UNSPSC: 12352108
• ID PubChem: 329755051
• NACRES: NA.22

Proprietà

• product name: Di-tert-butyl dicarbonate, ≥98.0% (GC)
• Livello qualitativo: 200
• Saggio: ≥98.0% (GC)
• Forma fisica: solid or liquid
• Indice di rifrazione: n20/D 1.409 (lit.)
• P. eboll.: 56-57 °C/0.5 mmHg (lit.)
• Punto di fusione: 23 °C (lit.)
• Densità: 0.95 g/mL at 25 °C (lit.)
• applicazioni: peptide synthesis
• Temperatura di conservazione: 2-8°C
• Stringa SMILE: 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; DYHSDKLCOJIUFX-UHFFFAOYSA-N

Descrizione

Descrizione generale

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)

Applicazioni

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.

Attenzione

Hydrolyzes to t-butanol and CO₂; causes internal pressure in bottle if exposed to moisture.

Informazioni sulla sicurezza

• Pittogrammi: GHS02,GHS06,GHS05
• Avvertenze: Danger
• Indicazioni di pericolo: H226,H315,H317,H318,H330,H335
• Consigli di prudenza: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Classi di pericolo: Acute Tox. 1 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• Organi bersaglio: Respiratory system
• Codice della classe di stoccaggio: 3 - Flammable liquids
• Classe di pericolosità dell'acqua (WGK): WGK 3
• Punto d’infiammabilità (°F): 98.6 °F - closed cup
• Punto d’infiammabilità (°C): 37 °C - closed cup
• Dispositivi di protezione individuale: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter