Informativa e consenso per l'uso dei cookie

Accetto Il nostro sito salva piccoli pezzi di informazioni (cookie) sul dispositivo, al fine di fornire contenuti migliori e per scopi statistici. È possibile disattivare l'utilizzo di cookies modificando le impostazioni del tuo browser. Continuando la navigazione si acconsente all'utilizzo dei cookie.

24424-99-5 - Di-tert-butyl dicarbonate, 97+% - Boc anhydride - Di-tert-butyl pyrocarbonate - A14708 - Alfa Aesar

A14708 Di-tert-butyl dicarbonate, 97+%

Codice CAS
24424-99-5
Sinonimi
Boc anhydride
Di-tert-butyl pyrocarbonate

Dimensioni Prezzo ($) Quantità Disponibilità
25g 37,29
100g 115,15
500g 453,20
Aggiungi al carrello Aggiungi al preventivo generale Visualizza articolo

Di-tert-butyl dicarbonate, 97+%

MDL
MFCD00008805
EINECS
246-240-1

Proprietà chimiche

Formula
C10H18O5
Peso formula
218.25
Punto di fusione
21-24°
Punto di ebollizione
56-57°/0.5mm
Punto di infiammabilità
37°(99°F)
Densità
0.950
Indice di rifrazione
1.4090
Sensibilità
Moisture Sensitive
Solubilità
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.

Applicazioni

Reagent for the introduction of the Boc protecting group.Di-tert-butyl dicarbonate is a reagent used for the introduction of BOC protecting group. It plays an important role in the preparation of 6-acetyl-1,2,3,4-tetrahydropyridine by reacting with 2-piperidone. It serves as a protecting group used in solid phase peptide synthesis.

Note

Store in a cool place. Keep the container tightly closed in a dry and well-ventilated place. Moisture and light sensitive. Incompatible with oxidizing agents, reducing agents, bases and acids.

Letteratura

Reagent for amino group protection as the tert-butyl carbamate (tert-butoxycarbonyl, Boc derivatives), in high yield under mild conditions, widely used in peptide chemistry; see Appendix 6. For practical details, literature references and tabulated results, see: Org. Synth. Coll., 7, 70 (1990). For further examples see: Synthesis, 223 (1987): Org. Synth. Coll., 9, 124, 300 (1998). Benzyl carbamates (Cbz, Z) may be transformed into Boc in a one pot procedure catalyzed by Pd/C: Tetrahedron Lett., 33, 3167 (1992).

Rapid and efficient formation of Boc derivatives of amines, catayzed by Copper(II)­ tetrafluoroborate hexahydrate, 26127 has been described: Tetrahdron Lett., 47, 1087 (2006).

For Boc protection of phenols, alcohols, thiols etc. under phase-transfer conditions, see: Can. J. Chem., 63, 153 (1985).

Amides can be protected in the presence of a catalytic quantity of DMAP ( 4-(Dimethyl­amino)­pyridine, A13016 ): J. Org. Chem., 48, 2424 (1983); Acta Chem. Scand. B, 40, 745 (1986); the amide link of the product undergoes facile alkaline hydrolysis or methanolysis. The nitrogen function of indoles and pyrroles can also be protected under similar conditions: J. Chem. Soc., Chem. Commun., 1699 (1984); Org. Synth. Coll., 9, 121 (1998). 1-Boc indoles may be synthesized from N-Boc 2-alkylanilines: Synthesis, 871 (1991).

The Boc group is readily cleaved with acid, most often Trifluoroacetic acid, L06374 .

In the presence of 1 equivalent of DMAP in acetonitrile, arylamines are converted to isocyanates, generally in high yield; the dicarbonate here behaves as a convenient phosgene replacement: Angew. Chem. Int. Ed., 34, 2497 (1995). The same reagent system has also been applied to nitroalkanes for the ambient temperature generation of nitrile oxides which were trapped in situ with dipolarophiles: Synthesis, 309 (1997). Carboxylic acids can be esterified in the presence of a catalytic amount of DMAP: Synlett, 263 (2004).

Carboxylic acids have also been converted to Boc-protected amines, via a one-pot Curtius rearrangement, using the reagent in the presence of sodium azide, with catalytic amounts of TBAB and zinc triflate: Org. Lett., 7, 4107 (2005).

For a brief feature on uses of the reagent in synthesis, see: Synlett, 1995 (2001).

Hong, X.; Wang, H.; Liu, B.; Xu, B. Ruthenium-catalyzed double-fold C-H tertiary alkoxycarbonylation of arenes using di-tert-butyl dicarbonate. Chem. Commun. 2014, 50 (91), 14129-14132.

Sweis, R. F.; Wang, Z.; Algire, M.; Arrowsmith, C. H.; Brown, P. J.; Chiang, G. G.; Guo, J.; Jakob, C. G.; Kennedy, S.; Li, F.; Maag, D.; Shaw, B.; Soni, N. B.; Vedadi, M.; Pappano, W. N. The Discovery of A-893, A New Cell-Active Benzoxazinone Inhibitor of Lysine Methyltransferase SMYD2. ACS Med. Chem. Lett. 2015, 6 (6), 695-700.

Rischio GHS e dichiarazioni precauzionali

Dichiarazioni di rischio (UE): H330-H315-H317-H335-H318-H228

Fatal if inhaled. Causes skin irritation. May cause an allergic skin reaction. May cause respiratory irritation. Causes serious eye damage. Flammable solid.

Dichiarazioni precauzionali: P280-P305+P351+P338-P304+P340-P310-P302+P352

Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. IF ON SKIN: Wash with plenty of soap and water.

Altri riferimenti

Beilstein
1911173
Classe di rischio
6.1
Gruppo di imballaggio
II
Codice tariffe armonizzato
2920.90
TSCA
Yes
RTECS
HT0230000

Raccomandato

  • A10807

    1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 98+%
  • A10973

    N,N'-Dicyclohexylcarbodiimide, 99%
  • A12646

    Triethylamine, 99%
  • A13016

    4-(Dimethylamino)pyridine, 99%
  • L06374

    Trifluoroacetic acid, 99%

Visualizzati di recente

Prodotti chimici

Scienze della vita

Metalli e materiali

Catalizzatori

Apparecchiature di analisi e di laboratorio