| Identification | More | [Name]
Di-tert-butyl dicarbonate | [CAS]
24424-99-5 | [Synonyms]
BOC
(BOC)2O
(BOC)2O FLUKA
BOC ANHYDRIDE
DBDC
DIBOC
DICARBONIC ACID, BIS(1,1-DIMETHYLETHYL) ESTER
DI-T-BUTYL DICARBONATE
DI-T-BUTYL PYROCARBONATE
DI-TERT-BUTYL DICARBONATE
DI-TERT-BUTYL PYROCARBONATE
PYROCARBONIC ACID DI-TERT-BUTYL ESTER
RARECHEM TB OC 0001
bis(1,1-dimethylethyl)dicarbonate
bis(tert-butoxycarbonyl)oxide
boc-acidanhydride
di-tert-butyloxydiformate
oxydi-formicacidi-tert-butylester
tert-butyldicarbonate
(t.-Boc)2O | [EINECS(EC#)]
246-240-1 | [Molecular Formula]
C10H18O5 | [MDL Number]
MFCD00008805 | [Molecular Weight]
218.25 | [MOL File]
24424-99-5.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white microcrystalline powder | [Melting point ]
23 °C (lit.) | [Boiling point ]
56-57 °C/0.5 mmHg (lit.) | [density ]
0.95 g/mL at 25 °C(lit.)
| [vapor pressure ]
3.85Pa at 25℃ | [refractive index ]
n20/D 1.409(lit.)
| [Fp ]
99 °F
| [storage temp. ]
2-8°C
| [solubility ]
Chloroform (Sparingly), Methanol (Slightly) | [form ]
Low Melting Crystalline Solid | [color ]
White | [Specific Gravity]
0.950 | [Water Solubility ]
Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water. | [Sensitive ]
Moisture Sensitive | [Detection Methods]
GC | [BRN ]
1911173 | [Stability:]
Acid Sensitive | [InChIKey]
DYHSDKLCOJIUFX-UHFFFAOYSA-N | [LogP]
1.87 at 25℃ | [CAS DataBase Reference]
24424-99-5(CAS DataBase Reference) | [EPA Substance Registry System]
24424-99-5(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
T+,T,F,Xi,F+ | [Risk Statements ]
R11:Highly Flammable.
R19:May form explosive peroxides.
R26:Very Toxic by inhalation.
R36/37/38:Irritating to eyes, respiratory system and skin .
R43:May cause sensitization by skin contact.
R10:Flammable. | [Safety Statements ]
S16:Keep away from sources of ignition-No smoking .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S36/37:Wear suitable protective clothing and gloves .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S7/9:Keep container tightly closed and in a well-ventilated place .
S37/39:Wear suitable gloves and eye/face protection .
S24:Avoid contact with skin .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S33:Take precautionary measures against static discharges . | [RIDADR ]
UN 2929 6.1/PG 1
| [WGK Germany ]
3
| [RTECS ]
HT0230000
| [F ]
4.4-10-21 | [Autoignition Temperature]
460 °C | [Hazard Note ]
Flammable/Irritant/Very Toxic | [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
I | [HS Code ]
29209010 | [Toxicity]
LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg |
| Hazard Information | Back Directory | [Chemical Properties]
Di-tert-butyl dicarbonate (Boc2O,24424-99-5
) and di-tert-butyl tricarbonate ((BocO)2CO) have been used as amine carbonylating reagents to obtain linear or branched aliphatic isocyanates.
most of the known methods for transforming amines into isocyanates are not mild enough and furnish undefined products as a result of uncontrolled side reactions. However, 4-dimethylaminopyridine (DMAP)-catalyzed reaction with activated carbonates as C1 building blocks constitutes a convenient laboratory method for the phosgene-free isocyanation of amines. A procedure has been described whereby alkyl- and arylamines are converted into isocyanates in high yields by reaction with activated carbonates (for example, di-tert-butyl dicarbonate, Boc2O) in the presence of a catalytic amount of a nucleophilic nitrogen base at room temperature.
Di-tert-butyl dicarbonate (Boc2O) is a widely used reagent for introducing protecting groups in peptide synthesis. 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.
| [Chemical Properties]
White to off-white microcrystalline powder | [Uses]
Reagent commonly used in organic chemistry for the introduction of the BOC protecting group. | [Uses]
reagent for t-BOC-protected amines | [Uses]
Reagent for the preparation of Boc-amino acids and peptides in high yields. | [Application]
Di-tert-butyl dicarbonate(24424-99-5) has the following uses:
(1) As part of a series of bovine plasma amine oxidase inactivators. Aminomethylenes were prepared by the reaction of Boc propargylamine with formaldehyde, diisopropylamine and copper bromide.
(2) It can be used as a general purpose carboxylation reagent. Carbon nucleophiles generated by a non-nucleophilic base (LDA) were effectively trapped with di-tert-butyl dicarbonate (Boc-anhydride) to provide the corresponding tert-butyl aryl acetates, di-tert-butyl aryl malonates, unsymmetrical aryl malonates and tert-butyl benzoates in high yields.
(3) Alcohols as Boc derivatives were catalytically protected by Lewis acids. Reagents for the introduction of Boc protecting groups.
(4) Reagents for the preparation of Boc-protected amines. Tri-tert-butoxycarbonyl-protected hydrazines prepare Fmoc esters in chromogenic reagents for monitoring solid-phase aldehydes.
| [Definition]
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid. | [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%. | [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. |
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