34660

Di-tert-butyl dicarbonate

≥98.0% (GC), for peptide synthesis

• 동의어(들): Boc₂O, Boc anhydride, Di-tert-butyl pyrocarbonate
• Linear Formula: [(CH₃)₃COCO]₂O
• CAS Number: 24424-99-5
• Molecular Weight: 218.25
• Beilstein: 1911173
• EC Number: 246-240-1
• MDL number: MFCD00008805
• UNSPSC 코드: 12352108
• PubChem Substance ID: 329755051
• NACRES: NA.22

속성

• 제품명: Di-tert-butyl dicarbonate, ≥98.0% (GC)
• Quality Level: 200
• 분석: ≥98.0% (GC)
• 양식: solid or liquid
• 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.)
• 응용 분야: peptide synthesis
• 작용기: carbonate
• 저장 온도: 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

설명

일반 설명

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.[1][2]

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)

애플리케이션

Di-tert-butyl dicarbonate (Boc₂O) has been used in the synthesis of:

• An azobenzene amino acid(aa).[3]
• N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-BOC-MDMA) from MDMA.[4][5]

It can also be used as a reagent:

• To introduce acid-labile Boc-protecting group in amino acids, peptides, and proteins.[1][6]        
• To prepare styrene derivatives by Heck olefination of aromatic carboxylic acids in the presence of a Pd catalyst.[7]        
• To synthesize oxazolidin-2-ones and imidazolidin-2-ones by isocyanation of 1,2-aminoalcohols and 1,2-diamines using DMAP as a catalyst.[8]       
• In the preparation of N-tert-butoxycarbonyl-3,4-methylenedioxymethamphetamine (t-Boc-MDMA) from MDMA.[4]
• For the conversion of amines to corresponding isocyanates, carbamates, and urea derivatives.[9]
• In the N-BOC-ylation of amides.[10][11]
• In the N-BOC-ylation of sensitive compounds under non-aqueous conditions.[12]

Reagent for the introduction of the Boc protecting group.

경고

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

안전성 정보

• 픽토그램: GHS02,GHS06,GHS05
• 신호어: Danger
• 유해 및 위험 성명서: H226,H315,H317,H318,H330,H335
• 예방조치 성명서: P210 - P233 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338
• Hazard Classifications: Acute Tox. 1 Inhalation - Eye Dam. 1 - Flam. Liq. 3 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3
• 표적 기관: Respiratory system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point (°F): 98.6 °F - closed cup
• Flash Point (°C): 37 °C - closed cup
• 개인 보호 장비: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter