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

A14708 Di-tert-butyl dicarbonate, 97+%

CAS Number
24424-99-5
Synonyms
Boc anhydride
Di-tert-butyl pyrocarbonate

Size Price ($) Quantity Availability
25g 37.29
100g 115.15
500g 453.20
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Di-tert-butyl dicarbonate, 97+%

MDL
MFCD00008805
EINECS
246-240-1

Chemical Properties

Formula
C10H18O5
Formula Weight
218.25
Melting point
21-24°
Boiling Point
56-57°/0.5mm
Flash Point
37°(99°F)
Density
0.950
Refractive Index
1.4090
Sensitivity
Moisture Sensitive
Solubility
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.

Applications

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.

Notes

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.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: 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.

Precautionary Statements: 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.

Other References

Beilstein
1911173
Hazard Class
6.1
Packing Group
I
Harmonized Tariff Code
2920.90
TSCA
Yes
RTECS
HT0230000

Recommended

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    4-(Dimethylamino)pyridine, 99%
  • A12646

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  • A10973

    N,N'-Dicyclohexylcarbodiimide, 99%
  • L06374

    Trifluoroacetic acid, 99%
  • A10807

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

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