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Di-tert-butyl dicarbonate, 97+%, Thermo Scientific Chemicals
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Catalog number A14708.14
Price (USD)/ Each
44.65
Online exclusive
49.00 Save 4.35 (9%)
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Quantity:
25 g
Price (USD)/ Each
44.65
Online exclusive
49.00 Save 4.35 (9%)
Di-tert-butyl dicarbonate, 97+%, Thermo Scientific Chemicals
Catalog numberA14708.14
Price (USD)/ Each
44.65
Online exclusive
49.00 Save 4.35 (9%)
-
Chemical Identifiers
CAS24424-99-5
IUPAC Namedi-tert-butyl dicarbonate
Molecular FormulaC10H18O5
InChI KeyDYHSDKLCOJIUFX-UHFFFAOYSA-N
SMILESCC(C)(C)OC(=O)OC(=O)OC(C)(C)C
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Specifications
Specification Sheet
Specification SheetAppearance (Color)Clear colorless or white to pale yellow
FormCrystals or powder or crystalline powder or fused/lumpy solid or liquid as melt
Assay from Supplier's CofA≥97.0%
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.
This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.
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.
Solubility
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
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.
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.
Solubility
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
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.
RUO – Research Use Only
General 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-(Dimethyl amino) 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).