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Di-tert-butyl dicarbonate

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Di-tert-butyl dicarbonate Basic information
Product Name:Di-tert-butyl dicarbonate
Synonyms:(BOC)2O;(BOC)2O FLUKA;BOC;BOC ANHYDRIDE;tert-butyldicarbonate;PYROCARBONIC ACID DI-TERT-BUTYL ESTER;RARECHEM TB OC 0001;Boc Anhydride, solid/liquid
CAS:24424-99-5
MF:C10H18O5
MW:218.25
EINECS:246-240-1
Product Categories:Pharmaceutical Intermediates;Starting Raw Materials & Intermediates;Amino Acid Derivatives;Organics;N-Protecting Reagents;Biochemistry;Peptide Synthesis;Protection & Derivatization Reagents (for Synthesis);Protective Reagents (Peptide Synthesis);Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;Boc-Amino acid series;Miscellaneous Reagents;DIBOC
Mol File:24424-99-5.mol
Di-tert-butyl dicarbonate Structure
Di-tert-butyl dicarbonate Chemical Properties
Melting point 23 °C (lit.)
Boiling point 56-57 °C/0.5 mmHg (lit.)
density 0.95 g/mL at 25 °C (lit.)
refractive index n20/D 1.409(lit.)
Fp 99 °F
storage temp. 2-8°C
form Low Melting Crystalline Solid
Specific Gravity0.950
color White
Water Solubility Miscible with decalin, toluene, carbon tetrachloride, tetrahydrofuran, dioxane, alcohols, acetone, acetonitrile and dimethylformamide. Immiscible with water.
Sensitive Moisture Sensitive
BRN 1911173
InChIKeyDYHSDKLCOJIUFX-UHFFFAOYSA-N
CAS DataBase Reference24424-99-5(CAS DataBase Reference)
EPA Substance Registry SystemDicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5)
Safety Information
Hazard Codes T+,T,F,Xi,F+
Risk Statements 11-19-26-36/37/38-43-10-40
Safety Statements 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33
RIDADR UN 2929 6.1/PG 1
WGK Germany 3
RTECS HT0230000
4.4-10-21
Autoignition Temperature460 °C
Hazard Note Flammable/Irritant/Very Toxic
TSCA Yes
HazardClass 6.1
PackingGroup I
HS Code 29209010
ToxicityLD50 orally in Rabbit: > 5000 mg/kg LD50 dermal Rabbit > 2000 mg/kg
MSDS Information
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Di-tert-butyl dicarbonate Usage And Synthesis
Chemical PropertiesWhite to off-white microcrystalline powder
Chemical PropertiesDi-tert-butyl dicarbonate (Boc2O) 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.
UsesReagent commonly used in organic chemistry for the introduction of the BOC protecting group.
Usesreagent for t-BOC-protected amines
UsesReagent for the preparation of Boc-amino acids and peptides in high yields.
Purification MethodsMelt 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.
Di-tert-butyl dicarbonate Preparation Products And Raw materials
Raw materialsTetrahydrofuran-->Carbon tetrachloride-->CARBON DIOXIDE-->Potassium tert-butoxide-->1,8-Diazabicyclo[5.4.0]undec-7-ene-->N-OCTANE
Preparation ProductsN-Boc-D-proline-->BOC-L-Isoleucine-->5-[N-(TERT-BUTOXYCARBONYL)AMINO]-2-CHLOROPYRIDINE-->TERT-BUTYL 4-(5-FORMYL-4-METHYL-1,3-THIAZOL-2-YL)PIPERIDINE-1-CARBOXYLATE-->1-Boc-4-cyanopiperidine-->TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE-->6-TERT-BUTOXYCARBONYLAMINO-PYRIDINE-2-CARBOXYLIC ACID-->1-TERT-BUTYL 6-METHYL 3-FORMYL-1H-INDOLE-1,6-DICARBOXYLATE-->(S)-N-Boc-allylglycine-->TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE-->2-(2,2-DIMETHYL-PROPIONYLAMINO)-ISONICOTINIC ACID-->1-Boc-piperazine acetate-->Spermidine-->TERT-BUTYL 3-(4-AMINO-2,6-DICHLOROPHENOXY)PROPYLCARBAMATE-->3-TERT-BUTOXYCARBONYLAMINO-ISONICOTINIC ACID-->6-BOC-HYDRAZINONICOTINIC ACID-->4-BOCAMINO-NICOTINIC ACID-->(S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine-->(R)-PIPERAZINE-2-CARBOXYLIC ACID-->(3-HYDROXYMETHYL-PYRIDIN-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER-->6-(BOC-AMINO)-HEXYL BROMIDE-->N-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLIC ACID T-BUTYL ESTER-->4-ALLYL-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER-->1-BOC-PIPERAZINE-->TERT-BUTYL 4-(HYDROXYMETHYL)PYRIDIN-2-YLCARBAMATE-->1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE-->(S)-(-)-1-Boc-2-pyrrolidinemethanol-->TERT-BUTYL 4-FORMYL-2-METHOXYPHENYL CARB ONATE, 99-->3-[(N-(TERT-BUTYLOXYCARBONYL)AMINO)METHYL]PYRIDINE-->tert-Butyl N-(2-bromoethyl)carbamate-->N-Boc-N,N-bis(2-chloroethyl)amine-->4-CHLORO-(N-BOC)ANILINE 97-->TERT-BUTYL N-(2-HYDROXYETHYL)CARBAMATE-->4-(BOC-AMINOMETHYL)PYRIDINE-->N-BOC-piperidine-4-carboxylic acid-->1-(4-PYRIDYLMETHYL)PIPERAZINE-->N,N-DIMETHYL-2-PIPERAZIN-1-YL-ACETAMIDE-->1-Boc-3-oxopiperazine
Tag:Di-tert-butyl dicarbonate(24424-99-5) Related Product Information
(2,6,6-Trimethyl-2-hydroxycyclohexylidene)acetic acid lactone Di-tert-butyl peroxide Diisobutyl phthalate Dimethyl succinate Diethyl carbonate Diethyl pyrocarbonate DMC Di-tert-butyl dicarbonate tert-Butanol Dibutyl sebacate Butyldiglycol Dimethyl dicarbonate BUTYL OLEATE DIBUTYL CARBONATE Dicarbonate Di-tert-Butyl azodicarboxylate TERT-BUTYL FORMATE METHYL ISOPROPYL CARBONATE