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24424-99-5

Basic Information
CAS No.: 24424-99-5
Name: Di-tert-butyl dicarbonate
Molecular Structure:
Molecular Structure of 24424-99-5 (Di-tert-butyl dicarbonate)
Formula: C10H18O5
Molecular Weight: 218.25
Synonyms: tert-Butoxycarbonyl anhydride;Bis(tert-butoxycarbonyl)oxide;Pyrocarbonic acid di-tert-butyl ester;Boc Anhydride;tert-butoxycarbonyl tert-butyl carbonate;Di(tert-butyl) carbonate;Dicarbonic acid, bis(1,1-dimethylethyl) ester;tert-Butyl dicarbonate;BOC-acidanhydride;Di-tert-butyl dicarbonate (Boc Anhydride);Di-tert-butyl dicarbonate(DIBOC);Di-BocDi-t-butyl Dicarbonate;Di-t-butyl pyrocarbonate;
EINECS: 246-240-1
Density: 1.054 g/cm3
Melting Point: 22-24 °C
Boiling Point: 235.8 °C at 760 mmHg
Flash Point: 103.7 °C
Solubility: insoluble in water
Appearance: white to off-white microcrystalline powder
Hazard Symbols: ToxicT, VeryT+, FlammableF, HighlyF+, IrritantXi
Risk Codes: 11-19-26-36/37/38-43-10
Safety: 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33
Transport Information: UN 2929 6.1/PG 1
PSA: 61.83000
LogP: 2.87320
Synthetic route

3-benzyl-9-tert-butyloxycarbonyl-3,9-diazabicyclo[3.3.1]nonane

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; under 2280.15 Torr;99%
865-47-4

potassium tert-butylate

4086-73-1

N-octylpyridinium chloride

124-63-0

methanesulfonyl chloride

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With pyridine; sulfuric acid; sodium hydrogencarbonate In hexane; water90%
865-47-4

potassium tert-butylate

124-63-0

methanesulfonyl chloride

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With pyridine; sulfuric acid; sodium hydrogencarbonate In hexane; water89%
In hexane; water87%
In water; N,N-dimethyl-formamide; toluene24%
865-47-4

potassium tert-butylate

104-74-5

N-dodecylpyridinium chloride

124-63-0

methanesulfonyl chloride

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
In hexane; water89%
32315-10-9

bis(trichloromethyl) carbonate

sodium t-butyl carbonate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
at 0 - 30℃; for 4h;88.79%
124-38-9

carbon dioxide

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
Stage #1: carbon dioxide With pyridine; benzyltrimethylammonium chloride; p-toluenesulfonyl chloride In toluene
Stage #2: With sulfuric acid In water for 0.5h;
85%
4086-73-1

N-octylpyridinium chloride

124-63-0

methanesulfonyl chloride

865-48-5

sodium t-butanolate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With sulfuric acid; sodium hydrogencarbonate In hexane; water83%
104-74-5

N-dodecylpyridinium chloride

124-63-0

methanesulfonyl chloride

865-48-5

sodium t-butanolate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
In hexane; water80%
124-38-9

carbon dioxide

865-47-4

potassium tert-butylate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
Stage #1: carbon dioxide; potassium tert-butylate With pyridine; benzyltrimethylammonium chloride; p-toluenesulfonyl chloride In toluene
Stage #2: With sulfuric acid In water for 0.5h;
73%
32315-10-9

bis(trichloromethyl) carbonate

75-65-0

tert-butyl alcohol

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
Stage #1: bis(trichloromethyl) carbonate; tert-butyl alcohol With triethylamine In hexane at -5℃;
Stage #2: With sodium hydroxide In hexane; water at 10℃; for 5.33333h; Reagent/catalyst; Temperature;
72%
124-63-0

methanesulfonyl chloride

865-48-5

sodium t-butanolate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With pyridine; sulfuric acid; sodium hydrogencarbonate In hexane; water71%

sodium t-butyl carbonate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
Stage #1: sodium t-butyl carbonate With pyridine; benzyltrimethylammonium chloride; p-toluenesulfonyl chloride In toluene at 40 - 50℃; for 24h;
Stage #2: With sulfuric acid In water for 0.5h;
62.7%
With pyridine; triethylamine; trichloromethyl chloroformate In N,N-dimethyl-formamide; Petroleum ether at -5 - 25℃; for 3.5h;60 g
24424-95-1

di-tert-butyl tricarbonate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With dmap In [D3]acetonitrile for 0.166667h; Ambient temperature;
With triethylamine In tetrachloromethane
With 1,4-diaza-bicyclo[2.2.2]octane In tetrachloromethane
125260-47-1, 125260-50-6

(2S,12bS)-2-Methyl-1,3,4,6,7,12b-hexahydro-2H-indolo[2,3-a]quinolizine-12-carboxylic acid tert-butyl ester

A

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
Product distribution;
N-(t-butyloxycarbonyl) arginine hydrochloride [Boc-Arg (HCl)-OH]

N-(t-butyloxycarbonyl) arginine hydrochloride [Boc-Arg (HCl)-OH]

60-29-7

diethyl ether

501-53-1

benzyl chloroformate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
In sodium hydroxide; water
aqueous H2 SO4

aqueous H2 SO4

772-80-5

4-methylphenyl chlorosulfate

56-93-9

benzyltrimethylammonium chloride

sodium t-butyl carbonate

24424-99-5

di-tert-butyl dicarbonate

Conditions
ConditionsYield
With pyridine In toluene
478623-90-4

tert-butyl 4-((dimethylamino)methylene)-3,5-dioxopiperidine-1-carboxylate

4637-24-5

N,N-dimethyl-formamide dimethyl acetal

24424-99-5

di-tert-butyl dicarbonate

72-18-4

L-valine

24424-99-5

di-tert-butyl dicarbonate

13734-41-3

t-Boc-L-valine

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water100%
With sodium hydroxide In 1,4-dioxane; water at 0℃;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h;100%
632-20-2

D-Threonine

24424-99-5

di-tert-butyl dicarbonate

2592-18-9, 23082-29-3, 23082-30-6, 55674-67-4, 85979-33-5, 86748-77-8

(2R,3S)-2-tert-butoxycarbonylamino-3-hydroxybutyric acid

Conditions
ConditionsYield
With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 23h;100%
With sodium hydrogencarbonate In methanol; water at 20℃; for 36h; Inert atmosphere;95%
With sodium carbonate In tetrahydrofuran; water87%
61-90-5

L-leucine

24424-99-5

di-tert-butyl dicarbonate

13139-15-6

N-tert-butoxycarbonyl-L-leucine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane at 25℃; for 23h;100%
With sodium hydroxide In 1,4-dioxane; water at 0℃;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 19h;99%
73-32-5

L-isoleucine

24424-99-5

di-tert-butyl dicarbonate

13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃; for 24h;100%
Stage #1: L-isoleucine With sodium hydroxide In 1,4-dioxane; water at 0℃;
Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃;
100%
With sodium hydroxide In 1,4-dioxane; water at 0℃;100%
63-68-3

L-methionine

24424-99-5

di-tert-butyl dicarbonate

2488-15-5

N-tert-butoxycarbonyl-L-methionine

Conditions
ConditionsYield
Stage #1: L-methionine With sodium hydroxide In 1,4-dioxane; water at 0℃; for 0.25h;
Stage #2: di-tert-butyl dicarbonate In 1,4-dioxane; water at 0 - 20℃;
100%
With sodium hydroxide In water; tert-butyl alcohol95%
With triethylamine; sodium hydroxide In water; acetonitrile at 0 - 25℃; for 12h;95%
3054-01-1

S-benzyl-L-cysteine

24424-99-5

di-tert-butyl dicarbonate

5068-28-0

(2R)-3-benzylsulfanyl-2-tert-butoxycarbonylamino-propionic acid

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 4h;100%
With triethylamine99%
With sodium hydroxide In 1,4-dioxane; water at 20 - 40℃; for 15h;65%
24424-99-5

di-tert-butyl dicarbonate

150-13-0

4-amino-benzoic acid

66493-39-8

4-(N-tert-butoxycarbonyl)aminobenzoic acid

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water at 20℃; for 24h;100%
With triethylamine In 1,4-dioxane; water at 20℃; for 24h;100%
98%
110-89-4

piperidine

24424-99-5

di-tert-butyl dicarbonate

75844-69-8

t-butyl piperidinecarboxylate

Conditions
ConditionsYield
With indium(III) bromide at 30 - 35℃; for 0.0833333h;100%
aminosulfonic acid at 25 - 28℃; for 0.05h;100%
With 1-methylimidazolium tetrafluoroborate at 30 - 35℃; for 0.0333333h;100%
6859-99-0

3-hydroxypiperazine

24424-99-5

di-tert-butyl dicarbonate

85275-45-2

N-tert-butoxycarbonyl-3-piperidinol

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With triethylamine In methanol at 20℃; for 15h;99%
With triethylamine In methanol at 20℃; for 15h;99%
109-96-6

3-Pyrroline

24424-99-5

di-tert-butyl dicarbonate

73286-70-1

N-(tert-butoxycarbonyl)-3-pyrroline

Conditions
ConditionsYield
In tetrahydrofuran; water at 0 - 20℃; for 3.16667h;100%
In dichloromethane at 0 - 20℃; Inert atmosphere;100%
In dichloromethane at 0 - 20℃; for 18.58h; Inert atmosphere;100%
1003-29-8

2-pyrrole aldehyde

24424-99-5

di-tert-butyl dicarbonate

161282-57-1

N-tert-butoxycarbonylpyrrole-2-carboxaldehyde

Conditions
ConditionsYield
With N,N-dimethoxy-4-amino-pyridine; triethylamine In dichloromethane at 20℃; for 0.5h;100%
Stage #1: 2-pyrrole aldehyde With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 1h; Inert atmosphere;
Stage #2: di-tert-butyl dicarbonate In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; Inert atmosphere;
100%
In acetonitrile at 25℃; for 24h;99%
504-24-5

4-aminopyridine

24424-99-5

di-tert-butyl dicarbonate

98400-69-2

N-(4-pyridyl) t-butyl carbamate

Conditions
ConditionsYield
copper(II) bis(tetrafluoroborate) at 30 - 35℃; for 0.5h;100%
With perchloric acid at 30 - 35℃; for 0.25h;100%
In PEG-400 at 20℃; for 0.25h;100%
2555-05-7

3-methyl-2-pyrrolidinone

24424-99-5

di-tert-butyl dicarbonate

171017-18-8

tert-butyl 3-methyl-2-oxo-1-pyrrolidine-carboxylate

Conditions
ConditionsYield
With dmap; triethylamine In acetonitrile at 20℃; for 10h;100%
With dmap In acetonitrile96%
With dmap; triethylamine In tetrahydrofuran at 20℃; for 4h;95%
In tetrahydrofuran Heating;85%
With dmap; triethylamine In dichloromethane Ambient temperature;
109-83-1

(2-hydroxyethyl)(methyl)amine

24424-99-5

di-tert-butyl dicarbonate

57561-39-4

methyl(2-hydroxyethyl)carbamic acid tert-butyl ester

Conditions
ConditionsYield
In acetonitrile at 20℃; Condensation;100%
In dichloromethane at 20℃; for 1h;100%
In tetrahydrofuran at 20℃; for 4h;100%
35161-71-8

N-methylpropargylamine

24424-99-5

di-tert-butyl dicarbonate

124045-51-8

N-t-butoxycarbonyl-N-methylpropargylamine

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;100%
90%
In methanol at 20℃; for 16h; Inert atmosphere;87.6%
120-72-9

indole

24424-99-5

di-tert-butyl dicarbonate

75400-67-8

indole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap In tetrahydrofuran at 20℃; for 16h; Acylation;100%
With dmap In tetrahydrofuran at 20℃; for 2h;100%
With dmap In dichloromethane at 20℃;100%
5625-67-2

2-Ketopiperazine

24424-99-5

di-tert-butyl dicarbonate

76003-29-7

4-(t-butyloxycarbonyl)piperazin-2-one

Conditions
ConditionsYield
In dichloromethane for 3h;100%
In dichloromethane at 20℃; for 5h;100%
In dichloromethane at 20℃; Cooling with ice;100%
3731-52-0

3-Aminomethylpyridine

24424-99-5

di-tert-butyl dicarbonate

102297-41-6

3-methyl>pyridine

Conditions
ConditionsYield
In 1,4-dioxane for 3h; Ambient temperature;100%
With glycerol at 20℃; for 0.0833333h; Green chemistry; chemoselective reaction;96%
With triethylamine In dichloromethane at 0℃; for 1.5h;92%
271-34-1

5-azaindole

24424-99-5

di-tert-butyl dicarbonate

148760-75-2

tert-butyl 1H-pyrrolo[3,2-c]pyridine-1-carboxylate

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 18h;100%
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;98.2%
With triethylamine In dichloromethane at 25℃; for 12h; Inert atmosphere;98.2%
51-67-2

tyrosamine

24424-99-5

di-tert-butyl dicarbonate

64318-28-1

N-t-butoxycarbonyl-tyramine

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran; methanol at 0 - 20℃;100%
In tetrahydrofuran for 3.5h;100%
With triethylamine In N,N-dimethyl-formamide99%
83-34-1

3-Methylindole

24424-99-5

di-tert-butyl dicarbonate

89378-43-8

3-methyl-indole-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With dmap In acetonitrile at 20℃; for 22h;100%
With dmap In acetonitrile Ambient temperature;99%
With dmap In acetonitrile at 20℃; for 16h;98.5%
13258-63-4

4-(2-Aminoethyl)pyridine

24424-99-5

di-tert-butyl dicarbonate

109573-05-9

(tert-Butoxy)-N-<2-(4-pyridyl)ethyl>carbamat

Conditions
ConditionsYield
In dichloromethane at 20℃;100%
In tetrahydrofuran at 0 - 20℃; for 3.5h;81%
In dichloromethane at 25℃;73%
24424-99-5

di-tert-butyl dicarbonate

4043-87-2

pipecolic Acid

98303-20-9

1-(tert-butoxycarbonyl)piperidine-2-carboxylic acid

Conditions
ConditionsYield
With tetramethyl ammoniumhydroxide In acetonitrile for 72h; Ambient temperature;100%
Stage #1: di-tert-butyl dicarbonate; pipecolic Acid With potassium carbonate In water; acetone at 20℃;
Stage #2: With hydrogenchloride In water; acetone pH=~ 3;
99%
With sodium carbonate In ethanol; water at 20℃;99.6%
487-89-8

Indole-3-carboxaldehyde

24424-99-5

di-tert-butyl dicarbonate

57476-50-3

1-tert-butoxycarbonyl-3-formylindole

Conditions
ConditionsYield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In dichloromethane at 0℃; for 1.83333h; Substitution;100%
With dmap; triethylamine In dichloromethane at 20℃;100%
With dmap; triethylamine In dichloromethane at 20℃; for 0.5h; Inert atmosphere;100%
91-21-4

1,2,3,4-tetrahydroisoquinoline

24424-99-5

di-tert-butyl dicarbonate

138350-92-2

tert-butyl 1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Conditions
ConditionsYield
In dichloromethane for 1h; Ambient temperature;100%
In dichloromethane at 20℃; for 2h;100%
With triethylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;99%
24424-99-5

di-tert-butyl dicarbonate

71962-74-8

Ethyl nipecotate

148672-74-6, 130250-54-3

ethyl N-(t-butyloxycarbonyl)nipecotate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;100%
With dmap; triethylamine In water; acetonitrile for 22h;99%
98%
1126-09-6

4-carbethoxypiperidine

24424-99-5

di-tert-butyl dicarbonate

142851-03-4

1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
In tetrahydrofuran100%
With triethylamine In dichloromethane at 20℃; Product distribution / selectivity;100%
41034-52-0

1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

24424-99-5

di-tert-butyl dicarbonate

166591-85-1

(±)-2-tert-butoxycarbonyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylic acid

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃;100%
With sodium hydroxide In tert-butyl alcohol84%
With sodium hydroxide In tert-butyl alcohol for 24h; Ambient temperature;
With triethylamine In tetrahydrofuran; water8.0 g (85%)
107-97-1

sarcosine

24424-99-5

di-tert-butyl dicarbonate

13734-36-6

N-(tert-butoxycarbonyl)sarcosine

Conditions
ConditionsYield
With triethylamine In water for 6h;100%
With triethylamine In water at 25℃; for 3h;97%
With sodium hydroxide In 1,4-dioxane95%
2213-08-3

ethyl 3-methylaminopropionate

24424-99-5

di-tert-butyl dicarbonate

54424-07-6

Ethyl 3-propionate

Conditions
ConditionsYield
In tetrahydrofuran for 1h; Ambient temperature;100%
With triethylamine In dichloromethane at 0℃;
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    Di-ter-butyl dicarbonate

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    ProName: Di-tert-butyl dicarbonate CAS NO.24424... CasNo: 24424-99-5 Molecular Formula: Di-tert-butyl dicarbonate Appearance: crystal, powder Application: Pharmaceutical intermediates DeliveryTime: 1-2 days PackAge: as yo

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    Boc Anhydride

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  • Di-tert-butyl dicarbonate

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    Di-tert-butyl dicarbonate

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Specification

1.Introduction of Di-tert-butyl dicarbonate

The IUPAC name of Boc anhydride is tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate. With the CAS registry number 24424-99-5, it is also named as Di-tert-butyl dicarbonate. The product's categories are Amino Acid Derivatives; Starting Raw Materials & Intermediates; 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. Besides, it is white to off-white microcrystalline powder, which should be stored in closed containers in a cool, dry place at 2-8 °C.

2.The properties of Di-tert-butyl dicarbonate

(1)EINECS: 246-240-1; (2)ACD/LogP: 2.88; (3)# of Rule of 5 Violations: 0; (4)ACD/LogD (pH 5.5): 2.88; (5)ACD/LogD (pH 7.4): 2.88; (6)ACD/BCF (pH 5.5): 90.45; (7)ACD/BCF (pH 7.4): 90.45; (8)ACD/KOC (pH 5.5): 874.99; (9)ACD/KOC (pH 7.4): 874.99; (10)#H bond acceptors: 5; (11)#H bond donors: 0; (12)#Freely Rotating Bonds: 6; (13)Index of Refraction: 1.431; (14)Molar Refractivity: 53.6 cm3; (15)Molar Volume: 207 cm3; (16)Surface Tension: 31.2 dyne/cm; (17)Density: 1.054 g/cm3; (18)Flash Point: 103.7 °C; (19)Melting Point: 22-24 °C; (20)Enthalpy of Vaporization: 47.26 kJ/mol; (21)Boiling Point: 235.8 °C at 760 mmHg; (22)Vapour Pressure: 0.049 mmHg at 25 °C.

3.Structure descriptors of Di-tert-butyl dicarbonate

(1)SMILES: O=C(OC(=O)OC(C)(C)C)OC(C)(C)C
(2)InChI: InChI=1/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3
(3)InChIKey: DYHSDKLCOJIUFX-UHFFFAOYAG
 

4.Preparation of Di-tert-butyl dicarbonate

Di-tert-butyl dicarbonate can be prepared from tert-Butanol, Carbon dioxide, Phosgene, using DABCO as a base.

5.Uses of Di-tert-butyl dicarbonate

The Di-tert-butyl dicarbonate is an intermediate and amino-protecting agent widely used in organic synthesis. It is also used in the Synthesis of 6-acetyl-1,2,3,4-tetrahydropyridine. Simlilarly, it can react with 3-Amino-benzoic acid to get 3-tert-Butoxycarbonylamino-benzoic acid.



This reaction needs Et3N, H2O and Dioxane at temperature of 20 °C for 24 hours. The yield is 100 %.

6.Safety information of Di-tert-butyl dicarbonate

The Di-tert-butyl dicarbonate is highly flammable that may form explosive peroxides. Please keep away from sources of ignition. It is also very toxic by inhalation, so you should keep container tightly closed in a well-ventilated place. Moreover, it is irritating to eyes, respiratory system and skin. And it may cause sensitization by skin contact. In case of contact with eyes, please rinse immediately with plenty of water and seek medical advice. Additionally, you should wear suitable protective clothing, gloves and eye/face protection to avoid contact with skin. After contact with skin, please wash immediately with plenty of soap-suds. And please take precautionary measures against static discharges. What's more, in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible).

7. The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mammal (species unspecified) LD50 oral > 5gm/kg (5000mg/kg)   National Technical Information Service. Vol. OTS0538278,
mammal (species unspecified) LD50 skin > 2gm/kg (2000mg/kg)   National Technical Information Service. Vol. OTS0538278,
rat LC50 inhalation 100mg/m3/4H (100mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0538278,

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