24424-99-5 Usage
Chemical Properties
Di-tert-butyl dicarbonate (BOC Anhydride, DiBOC) is a colorless to white to yellow crystals, solidified mass or clear liquid. It melts around room temperature (m.p.=23°C). It does not decompose at this or even slightly higher temperatures. For example, it is typically purified by distillation under reduced pressure at temperatures up to around 65°C. At higher temperatures it will decompose to isobutene, t-butyl alcohol and carbon dioxide.
Uses
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. 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.
Preparation
The preparation of Di-tert-butyl dicarbonate is as follows:To a monoester sodium salt solution were added 2g of N, N-dimethylformamide, 1g of pyridine, 1g of triethylamine,Cooling to -5~0°C, 60g diphosgene was slowly added dropwise within 1.5h dropwise addition was complete, warmed to room temperature (25°C), incubated for 2h, the reaction was allowed to stand after filtration, washing organic solution. Dried with anhydrous magnesium sulfate, the solvent was distilled off at atmospheric pressure to give crude product 65~70g. After cooling and crystallization, 57-60g of di-tert-butyl dicarbonate were obtained in a yield of 60-63%.
Definition
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.
Reactions
The reaction of substituted anilines with Boc2O in the presence of a stoichiometric amount of 4-dimethylaminopyridine (DMAP) in an inert solvent (acetonitrile, dichloromethane, ethyl acetate, tetrahydrofuran, toluene) at room temperature leads to aryl isocyanates in almost quantitative yields within 10 min.Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. Their reactions with amines and alcohols
General Description
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.
Hazard
An irritant that may cause serious eye injury; May cause skin sensitization; Highly toxic by inhalation
Flammability and Explosibility
Flammable
Purification Methods
Melt the ester by heating at ~35o, and distil it in a vacuum. If IR and NMR ( 1810m 1765 cm-1 , in CCl4 1.50 singlet) suggest very max impure, then wash with an equal volume of H2O containing citric acid to make the aqueous layer slightly acidic, collect the organic layer and dry it over anhydrous MgSO4 and distil it in a vacuum. [Pope et al. Org Synth 57 45 1977, Keller et al. Org Synth 63 160 1985, Grehn et al. Angew Chem 97 519 1985.] FLAMMABLE.
Check Digit Verification of cas no
The CAS Registry Mumber 24424-99-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,4,2 and 4 respectively; the second part has 2 digits, 9 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 24424-99:
(7*2)+(6*4)+(5*4)+(4*2)+(3*4)+(2*9)+(1*9)=105
105 % 10 = 5
So 24424-99-5 is a valid CAS Registry Number.
InChI:InChI=1/C10H18O5/c1-8(2,3)11-7(10)12-9(4,5)6/h1-6H3
24424-99-5Relevant articles and documents
Modeling and spectroscopic studies of synthetic diazabicyclo analogs of the HIV-1 inhibitor BMS-378806 and evaluation of their antiviral activity
Legnani, Laura,Colombo, Diego,Cocchi, Elena,Solano, Lucrezia,Villa, Stefania,Lopalco, Lucia,Asti, Valeria,Diomede, Lorenzo,Marinone Albini, Franca,Toma, Lucio
, p. 287 - 294 (2011)
Three diazabicyclo analogs of BMS-378806, in which theaxial methyl group present on its piperazine ring is replaced by a carbon bridge, were synthesized and tested, through a viral neutralization assay, on a panel of six pseudoviruses. The diazabicyclooctane and-nonane derivatives maintained a significant infectivity reduction power, whereas the diazabicycloheptane derivative was much less effective. A modeling study allowed to relate the antiviral activity to the conformational preferences of the compounds. Moreover, similarly to BMS-378806, theoretical calculations predict the existence of different conformational families corresponding to the possible arrangements at the two planar amido functions of the compounds. High-field 1H NMR spectra confirm these results, as they show two distinct series of signals. A viral neutralization assay on a panel of six HIV-related pseudoviruses allowed the determination of the antiviral activity of three diazabicyclo analogs of BMS-378806, in which the axial methyl group on its piperazine ring is replaced by a carbon bridge. The diazabicyclooctane and-nonane derivatives show a significant infectivity reduction power that is related to their conformational preference. Copyright
Preparation method of di-tert-butyl dicarbonate
-
Paragraph 0025, (2017/07/19)
The invention relates to a preparation method of di-tert-butyl dicarbonate and belongs to the technical field of synthesis of pharmaceutical intermediates. The preparation method comprises the following steps: adding metal sodium into xylol; heating to obtain sodium sand; then dropwise adding tert-butyl alcohol and carrying out pumping filtration to obtain sodium tert-butoxide; dissolving the sodium tert-butoxide into petroleum ether; introducing carbon dioxide and reacting to obtain a monoester sodium salt solution; adding a catalyst and slowly dropwise adding diphosgene to react; after reacting, standing and carrying out the pumping filtration; and washing with water, drying, distilling, cooling and crystallizing to obtain the di-tert-butyl dicarbonate. According to the preparation method, the sodium tert-butoxide is prepared from the metal sodium and the di-tert-butyl dicarbonate is prepared from the sodium tert-butoxide; a pumping filtration method is used for replacing a previous distillation method, so that the process is simpler and more energy is saved; the petroleum ether is used for replacing n-hexane and toluene, so that the production cost is reduced and a product is easier to purify; and finally, after the reaction, the pumping filtration is carried out and then water washing is carried out, so that the amount of wastewater is reduced and the environment-friendly treatment cost is reduced.
NOVEL THIOPHENE DERIVATIVES AS SPHINGOSINE-1-PHOSPHATE-1 RECEPTOR AGONISTS
-
, (2011/10/01)
The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.
