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361941

Sigma-Aldrich

Di-tert-butyl dicarbonate

≥99%, for peptide synthesis, ReagentPlus®

Sinonimo/i:

Boc anhydride, Di-tert-butyl pyrocarbonate

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5 G
CHF 49.80
25 G
CHF 177.00
250 G
CHF 1’180.00

CHF 49.80

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Cambia visualizzazione
5 G
CHF 49.80
25 G
CHF 177.00
250 G
CHF 1’180.00

About This Item

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:
12352302
ID PubChem:
24862282
NACRES:
NA.22

CHF 49.80

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Nome del prodotto

Di-tert-butyl dicarbonate, ReagentPlus®, ≥99%

Livello qualitativo

200

Nome Commerciale

ReagentPlus®

Saggio

≥99%

Stato

solid or liquid

Indice di rifrazione

n20/D 1.409 (lit.)

P. ebollizione

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

Gruppo funzionale

carbonate

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

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Categorie correlate

Applicazioni

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)
Di-tert-butyl dicarbonate (Boc anhydride) can be used:
  • As a reagent to introduce Boc protecting group for the amine functionalities.[1][2]
  • To prepare tert-butyl ethers and Boc-alcohols in presence of Lewis acid catalyst.[3]
  • As a carboxylating agent for the preparation of a variety of tert-butyl carboxylates.[4]
  • For the conversion of amines to corresponding isocyanates, carbamates and urea derivatives.[4]
  • As a coupling reagent for anchoring various carboxylic acids to hydroxymethylated resins.[5]
  • To synthesize quinolinones and 2-(pseudo)haloquinolines from 2-alkenylanilines in presence of DMAP as a catalyst.[6]

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.

Note legali

ReagentPlus is a registered trademark of Merck KGaA, Darmstadt, Germany

Avvertenze

Danger

Indicazioni di pericolo

H226,H315,H317,H318,H330,H335

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

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Certificati d'analisi (COA)

Lot/Batch Number
BCCJ5699
BCCG6268
BCCG0558
BCCF2132
BCCC9639

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Di-tert-butyl dicarbonate as an efficient coupling reagent for the immobilization of carboxylic acid moieties
de los Angeles Laborde M, et al.
Tetrahedron Letters, 49(31), 4624-4625 (2008)
Aqueous MW eco-friendly protocol for amino group protection
Nardi M, et al.
Royal Society of Chemistry Advances, 5(24), 18751-18760 (2015)
An expeditious, high-yielding construction of the food aroma compounds 6-acetyl-1, 2, 3, 4-tetrahydropyridine and 2-acetyl-1-pyrroline
Harrison TJ and Dake GR
The Journal of Organic Chemistry, 70(26), 10872-10874 (2005)
Beyond a Protecting Reagent: DMAP-Catalyzed Cyclization of Boc-Anhydride with 2-Alkenylanilines
Huang Y-N, et al.
The Journal of Organic Chemistry, 81(11), 4645-4653 (2016)
Synlett, 2104-2104 (2006)
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Questions

1–2 of 2 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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