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24424-99-5

Basic Information
CAS No.: 24424-99-5
Name: Di-tert-butyl dicarbonate
Article Data: 40
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%
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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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