ChemicalBook > CAS DataBase List > Di-tert-butyl dicarbonate

Di-tert-butyl dicarbonate

Product Name
Di-tert-butyl dicarbonate
CAS No.
24424-99-5
Chemical Name
Di-tert-butyl dicarbonate
Synonyms
BOC;(BOC)2O;DIBOC;BOC ANHYDRIDE;DI-T-BUTYL DICARBONATE;DBDC;DI-TERT-BUTYL PYROCARBONATE;tert-Butoxycarbonyl Anhydride;Di-tert-butyL;tert-butyldicarbonate
CBNumber
CB4267614
Molecular Formula
C10H18O5
Formula Weight
218.25
MOL File
24424-99-5.mol
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Di-tert-butyl dicarbonate Property

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.)
Flash point:
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
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
Dicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5)
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Safety

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
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
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H226Flammable liquid and vapour

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H330Fatal if inhaled

H335May cause respiratory irritation

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.52261
Product name
Di-tert-butyl dicarbonate
Purity
Novabiochem?
Packaging
25g
Price
$32.8
Updated
2024/03/01
Sigma-Aldrich
Product number
8.52261
Product name
Di-tert-butyl dicarbonate
Purity
Novabiochem?
Packaging
100g
Price
$87.9
Updated
2024/03/01
Sigma-Aldrich
Product number
34660
Product name
Di-tert-butyl dicarbonate
Purity
≥98.0% (GC)
Packaging
25g
Price
$57.6
Updated
2024/03/01
Sigma-Aldrich
Product number
205249
Product name
Di-tert-butyl dicarbonate
Purity
ReagentPlus , 99%
Packaging
10g
Price
$53.8
Updated
2024/03/01
Sigma-Aldrich
Product number
34660
Product name
Di-tert-butyl dicarbonate
Purity
≥98.0% (GC)
Packaging
100g
Price
$147
Updated
2024/03/01
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Di-tert-butyl dicarbonate Chemical Properties,Usage,Production

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.

Application

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.

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.

Di-tert-butyl dicarbonate Preparation Products And Raw materials

Raw materials

Potassium tert-butoxide N-OCTANE Carbon dioxide Carbon tetrachloride DBU Tetrahydrofuran

Preparation Products

TERT-BUTYL 4-(4-FORMYL-1,3-THIAZOL-2-YL)TETRAHYDRO-1(2H)-PYRIDINECARBOXYLATE N-4-Boc-2-piperazinecarboxylic acid 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 Spermidine 3-[(N-(TERT-BUTYLOXYCARBONYL)AMINO)METHYL]PYRIDINE tert-Butyl N-(2-bromoethyl)carbamate 3-TERT-BUTOXYCARBONYLAMINO-ISONICOTINIC ACID TERT-BUTYL 4-FORMYL-2-METHOXYPHENYL CARB ONATE, 99 (S)-N-Boc-allylglycine N-BOC-piperidine-4-carboxylic acid TERT-BUTYL 3-FORMYLPYRIDIN-4-YLCARBAMATE 4-ALLYL-PIPERIDINE-1,4-DICARBOXYLIC ACID MONO-TERT-BUTYL ESTER 1-Boc-3-oxopiperazine 2-(2,2-DIMETHYL-PROPIONYLAMINO)-ISONICOTINIC ACID 1-(4-PYRIDYLMETHYL)PIPERAZINE 6-(BOC-AMINO)-HEXYL BROMIDE BOC-L-Isoleucine 1-Boc-piperazine acetate 1-BOC-4-HYDROXY-4-(HYDROXYMETHYL)-PIPERIDINE 4-CHLORO-(N-BOC)ANILINE 97 BOC-L-Prolinol N,N-DIMETHYL-2-PIPERAZIN-1-YL-ACETAMIDE N-Boc-D-proline Tert-butyl bis(2-chloroethyl)carbamate 4-(BOC-AMINOMETHYL)PYRIDINE N-1-BOC-N-4-CBZ-2-PIPERAZINECARBOXYLIC ACID T-BUTYL ESTER TERT-BUTYL 4-(METHOXYCARBONYL)PYRIDIN-2-YLCARBAMATE 4-BOCAMINO-NICOTINIC ACID (S)-(-)-1-tert-Butoxycarbonyl-3-aminopyrrolidine 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-cyanopiperidine
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View Lastest Price from Di-tert-butyl dicarbonate manufacturers

Hebei Zhuanglai Chemical Trading Co.,Ltd
Product
Di-tert-butyl dicarbonate 24424-99-5
Price
US $10.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
20ton
Release date
2024-05-16
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Di-tert-butyl dicarbonate 24424-99-5
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
99%min
Supply Ability
10 tons
Release date
2021-07-16
Hebei Andu Technology Com.,Ltd
Product
Di-tert-butyl dicarbonate 24424-99-5
Price
US $3.50/kg
Min. Order
1kg
Purity
≥99%
Supply Ability
3000tons/month
Release date
2024-08-18

24424-99-5, Di-tert-butyl dicarbonateRelated Search:

DIBUTYL CARBONATE Dibutyl phthalate Diisobutyl phthalate Di-tert-Butyl azodicarboxylate Dimethyl succinate Diethyl carbonate Tris(trimethylsilyl)phosphate tert-Butanol Dibutyl sebacate Diethylene glycol monobutyl ether BUTYL OLEATE Diphenyl carbonate Cyhalofop-butyl Methyl acrylate Butyl acetate Buprofezin Dihydroactinidiolide Di-tert-butyl peroxide

  • (BOC)2O
  • (BOC)2O FLUKA
  • BOC
  • BOC ANHYDRIDE
  • tert-butyldicarbonate
  • PYROCARBONIC ACID DI-TERT-BUTYL ESTER
  • RARECHEM TB OC 0001
  • Boc Anhydride, solid/liquid
  • (t.-Boc)2O
  • di(tert-butyl) carbonate
  • Dibutyldicarbonate
  • di-t-Butyl-dicarbonate Dicarbonic acid, bis(1,1-dimethylethyl)ester
  • Di-tert-bicarbonate
  • Di-tert-butyl dicarbonate,Diboc
  • DI-TERT-BUTYL DICARBONATE, REAGENTPLUS, 99%
  • DI-TERT-BUTYL PYROCARBONATE GRADE II
  • DI-TERT-BUTYL DICARBONATE, 1.0M SOLUTION IN TETRAHYDROFURAN
  • DI-TERT-BUTYL DICARBONATE, 4X10 G
  • DI-TERT-BUTYL DICARBONATE, REAGENTPLUS, >=99%
  • DI-TERT-BUTYL DICARBONATE (BOC ANHYDRIDE)
  • Di-tert-butyl dicarbonate, 99%+ (Phosgene-free)
  • Di-tert-butyldicarbonate,97+%
  • DI-TERT-BUTYL DICARBONATE (DI-BOC) (BOC-2O)
  • Di-tert-butyl Dicarbonate [Boc-reagent for Amino Acid]
  • DIBOC,BOC
  • BOC-20Dicarbonic acid
  • Di-tert-butyl dicarbonate,Boc anhydride, Di-tert-butyl pyrocarbonate
  • Di-tert-butyl dicarbonate solution,Di-tert-butyl pyrocarbonate
  • Bis(tert-butyl) dicarbonate 99+%
  • Di-tert-butyl dicarb
  • Di-tert-butyl dicarbonate, 1M solution in THF, AcroSeal
  • BOC Anhydride (Di-t-butyl dicarbonate)
  • DiBoc (Di-tert-butyl dicarbonate)
  • Di-tert-butyl dicarbonate, 1M solution in THF, AcroSeal 100ML
  • Bis(tert-butyl) pyrocarbonate, BOC anhydride
  • (BOC)2O Boc Anhydride
  • Bis(1,1-diMethylethyl) Ester Dicarbonic Acid
  • Bis(tert-butyl) Dicarbonate
  • C,C'-bis(1,1-DiMethylethyl) Ester Dicarbonic Acid
  • Oxydi-forMic Acid Di-tert-butyl Ester
  • tert-Butoxycarbonyl Anhydride
  • Di-tert-butyl Pyrocarbonate Pyrocarbonic Acid Di-tert-butyl Ester Boc2O
  • Boc2O Di-tert-butyl Pyrocarbonate Pyrocarbonic Acid Di-tert-butyl Ester DiBoc Boc Anhydride
  • DI-TERT-BUTYL DICARBONATE FOR SYNTHESIS
  • Dicarbonic acid
  • TwoDi tert butylcarbonate
  • Dicarbonic acid, 1,3-bis(1,1-dimethylethyl) ester
  • JACS-24424-99-5
  • Di-tert-butyL
  • DI-T-BUTYL DICARBONATE
  • DI-T-BUTYL PYROCARBONATE
  • DI-TERT-BUTYL PYROCARBONATE
  • DI-TERT-BUTYL DICARBONATE
  • DICARBONIC ACID, BIS(1,1-DIMETHYLETHYL) ESTER
  • DIBOC
  • DBDC
  • bis(1,1-dimethylethyl)dicarbonate
  • bis(tert-butoxycarbonyl)oxide