? -Tert- ?? ? ?????
|
|
? -Tert- ?? ? ????? ??
- ???
- 23 °C (lit.)
- ?? ?
- 56-57 °C/0.5 mmHg (lit.)
- ??
- 0.95 g/mL at 25 °C (lit.)
- ???
- 3.85Pa at 25℃
- ???
- n
20/D 1.409(lit.)
- ???
- 99 °F
- ?? ??
- 2-8°C
- ???
- ?????(???? ??), ???(?? ???)
- ??? ??
- ??? ??? ??
- ??
- ???
- Specific Gravity
- 0.950
- ???
- ???, ???, ?????, ????????, ???, ???, ???, ?????? ? ????????? ?? ?????. ?? ??? ????.
- ??
- Moisture Sensitive
- BRN
- 1911173
- ???
- ??? ???
- InChIKey
- DYHSDKLCOJIUFX-UHFFFAOYSA-N
- LogP
- 1.87 at 25℃
- CAS ??????
- 24424-99-5(CAS DataBase Reference)
??
- ?? ? ?? ??
- ?? ? ???? ?? (GHS)
| ??? ?? | T+,T,F,Xi,F+ | ||
|---|---|---|---|
| ?? ???? ?? | 11-19-26-36/37/38-43-10-40 | ||
| ????? | 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33 | ||
| ????(UN No.) | UN 2929 6.1/PG 1 | ||
| WGK ?? | 3 | ||
| RTECS ?? | HT0230000 | ||
| F ?????? | 4.4-10-21 | ||
| ?? ?? ?? | 460 °C | ||
| ?? ?? ?? | Flammable/Irritant/Very Toxic | ||
| TSCA | Yes | ||
| ?? ?? | 6.1 | ||
| ???? | I | ||
| HS ?? | 29209010 | ||
| ?? | LD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg | ||
| ???? ?? | KE-10019 |
? -Tert- ?? ? ????? C??? ??, ??, ??
??
??? ??? ??, n- ??, ?? ?? ?????? ?? ?? ??? ???? ?? ?? ????.??
?? ? ?? ?? ???? ?? ? ?? ??? ????? ??? ??? ??????. ?? ? ?? ??? ???? ????, ?? ? ?? ??? ????? ??? ??? ??????. ?? ?? ???? ??, ??, ??, ???, ??, ?? ? ??? ?? ??? ?? ???? tert- ? ?? ?? ? ?? ??? ?? ?? ??? ??? ?? ??? ????. tert- ? ?? ?? ? ?? (???? ??); ? ???? ??? ???? ?? ?? ??? ?? ?? (? : ??, ?? ???? ???? ?)?? ??? ??? ???? ?? ?????. ?? ??, ?? ? ??, ??? ?? ? ??? ?? ?? ??? ?? (BOC)? ?? ? ???.??
? -tert- ?? ? ????? (Diboc)? ?? ????? ??? ????? tert- ? ?? ?? ? (BOC) ???? ???? ?? ?? ???? ???? ?? ? ??? - ?????. ???, ??? ? ???? ??, ???, ??, ??? ? ?? ??? ??? ?? ?????.??
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.?? ??
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%.??
ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.?? ??
Di-tert-butyl dicarbonate 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.
?? ??
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
?? ??
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.???
An irritant that may cause serious eye injury; May cause skin sensitization; Highly toxic by inhalationPurification 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.? -Tert- ?? ? ????? ?? ?? ? ???
???
?? ??
TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE
N-4-Boc-2-?????????
TERT-BUTYL 4-(HYDROXYMETHYL)PYRIDIN-2-YLCARBAMATE
1-BOC-PIPERAZINE
TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE
TERT-BUTYL 3-(4-AMINO-2,6-DICHLOROPHENOXY)PROPYLCARBAMATE
1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE
?????
3-[(N-(TERT-BUTYLOXYCARBONYL)AMINO)METHYL]PYRIDINE
tert-Butyl N-(2-bromoethyl)carbamate
3-TERT-??????????-??????
TERT-BUTYL 4-FORMYL-2-METHOXYPHENYL CARB ONATE, 99
(S)-N-Boc-?????
N-BOC-piperidine-4-carboxylic acid
TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE
4-ALLYL-PIPERIDINE-1,4-DICARBOXYLICACMON-TERT-BUTYL????
1-Boc-3-??????
2-(2,2-???-????????)-??????
1-(4-?????)????
6-(BOC-AMINO)-HEXYL BROMIDE
BOC-L-Isoleucine
1-Boc-piperazine acetate
1-BOC-4-HYDROXY-4-(???????)-????
4-CHLORO-(N-BOC)ANILINE 97
BOC-L-Prolinol
N,N-???-2-????-1-YL-??????
N-Boc-D-proline
N-Boc-N,N-??(2-?????)??
4-(BOC-AMINOMETHYL)PYRIDINE
N-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLICACIDT-??????
TERT-BUTYL 4-(METHOXYCARBONYL)PYRIDIN-2-YLCARBAMATE
4-????-????
(S)-(-)-1-tert-???????-3-???????
5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINE
6-BOC-HYDRAZINONICOTINIC ACID
TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE
6-TERT-BUTOXYCARBONYLAMINO-PYRIDINE-2-CARBOXYLIC ACID
(R)-PIPERAZINE-2-CARBOXYLIC ACID
(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER
1-Boc-4-???????
? -Tert- ?? ? ????? ?? ??
???( 1008)?? ??
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