3D Mol Similar

Di-tert-butyl dicarbonate

: Iupac Name：tert-butyl (2-methylpropan-2-yl)oxycarbonyl carbonate; CAS No.: 24424-99-5; Molecular Weight：218.249; Modify Date.: 2024-04-09 08:44; Introduction: Reagent commonly used in organic chemistry for the introduction of the BOC protecting group. View more+

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1. Names and Identifiers

: 1.1 Name; Di-tert-butyl dicarbonate; 1.2 Synonyms; (BOC)2O (BOC)2O FLUKA 3,3-Dimethylbutanoyl 2-methyl-2-propanyl carbonate Bis(2-methyl-2-propanyl) dicarbonate Bis(tert-butoxycarbonyl)oxide BOC BOC ANHYDRIDE Boc Anhydride, solid/liquid Boc2O boc-acidanhydride BOC-anhydride Carbonic acid, (1,1-dimethylethoxy)carbonyl 1,1-dimethylethyl ester Carbonic acid, 1,1-dimethylethyl 3,3-dimethyl-1-oxobutyl ester DBDC di(tert-butyl) carbonate Di(tert-butyl) dicarbonate DIBOC DIBOC,BOC Dibutyldicarbonate di-t-Butyl dicarbonate di-t-butylpyrocarbonate Di-tert-butyl Pyrocarbonate Di-tert-butyldicarbonat Di-tert-Butyldicarbonate EINECS 246-240-1 MFCD00008805 PYROCARBONIC ACID DI-TERT-BUTYL ESTER RARECHEM TB OC 0001 tert-butyldicarbonate; View all

1.3 CAS No.: 24424-99-5

1.4 CID: 90495

1.5 EINECS(EC#): 246-240-1

1.6 Molecular Formula: C10H18O5 (isomer)

1.7 Inchi: InChI=1S/C10H18O5/c1-9(2,3)14-7(11)13-8(12)15-10(4,5)6/h1-6H3

1.8 InChIkey: DYHSDKLCOJIUFX-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C

1.10 Isomers Smiles: CC(C)(C)OC(=O)OC(=O)OC(C)(C)C

2. Properties

2.1 Density: 0.949

2.1 Melting point: 22-24℃

2.1 Boiling point: 56-57℃ (0.5 torr)

2.1 Refractive index: 1.4075-1.4095

2.1 Flash Point: 37℃

2.1 Precise Quality: 218.11500

2.1 PSA: 61.83000

2.1 logP: 2.87320

2.1 Appearance: solid

2.2 Storage: Keep Cold. Moisture Sensitive. Store under Nitrogen.

2.3 Chemical Properties: White to off-white microcrystalline powder

2.4 Color/Form: White

2.5 Water Solubility: insoluble

2.6 Stability: Stable. Incompatible with strong oxidizing agents. Flammable.

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 133 companies from 26 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 1 of 133 companies. For more detailed information, please visit ECHA C&L website

Of the 25 notification(s) provided by 132 of 133 companies with hazard statement code(s):

H225 (31.82%): Highly Flammable liquid and vapor [Danger Flammable liquids]
H226 (62.88%): Flammable liquid and vapor [Warning Flammable liquids]
H228 (18.18%): Flammable solid [Danger Flammable solids]
H315 (99.24%): Causes skin irritation [Warning Skin corrosion/irritation]
H317 (96.21%): May cause an allergic skin reaction [Warning Sensitization, Skin]
H318 (14.39%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H319 (84.85%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H330 (98.48%): Fatal if inhaled [Danger Acute toxicity, inhalation]
H335 (56.82%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P210, P233, P240, P241, P242, P243, P260, P261, P264, P271, P272, P280, P284, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P320, P321, P332+P313, P333+P313, P337+P313, P362, P363, P370+P378, P403+P233, P403+P235, P405, and P501; View all

3.2 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 Preparation Products

3.3 Usage: Reagent commonly used in organic chemistry for the introduction of the BOC protecting group.

4. Safety and Handling

4.1 Symbol: GHS02, GHS05, GHS06

4.1 Hazard Codes: T+; Xi; F+

4.1 Signal Word: Danger

4.1 Risk Statements: R10;R26;R36/37/38;R43

4.1 Safety Statements: S16;S24;S37/39;S45

4.1 Packing Group: I

4.1 Hazard Class: 6.1

4.1 Hazard Declaration: H226-H315-H317-H318-H330-H335

4.1 RIDADR: 200kgs

4.1 Caution Statement: P210-P260-P280-P304 + P340 + P310-P305 + P351 + P338 + P310-P370 + P378

4.1 WGK Germany: 3

4.1 RTECS: HT0230000

4.1 Safety: Hazard Codes:?T+ ,?T ,?F,?Xi?,?F+
Risk Statements 11-19-26-36/37/38-43-10?
R11: Highly flammable.?
R19: May form explosive peroxides.?
R26: Very toxic by inhalation.?
R36/37/38: Irritating to eyes, respiratory system and skin.?
R43: May cause sensitization by skin contact.?
R10: Flammable.
Safety Statements 16-26-28-36/37-45-7/9-37/39-24-36/37/39-33?
S16: Keep away from sources of ignition.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S37/39: Wear suitable gloves and eye/face protection.?
S24: Avoid contact with skin.?S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR UN 2929 6.1/PG 1
WGK Germany 3
RTECS HT0230000
F: 4.4-10-21
HazardClass: 6.1
PackingGroup: I; View all

4.2 Sensitive: Moisture Sensitive

4.3 Specification: 1. First Aid Measures:
Ingestion: Do NOT induce vomiting. If victim is conscious and alert, give 2-4 cupfuls of milk or water. Never give anything by mouth to an unconscious person. Get medical aid immediately.
Inhalation: Remove from exposure to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid. DO NOT use mouth-to-mouth respiration.
Skin: Get medical aid. Flush skin with plenty of soap and water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
2. Handling and Storage:
Storage: Keep away from heat, sparks, and flame. Keep away from sources of ignition. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Refrigerator (approx 4 C).
Handling: Wash thoroughly after handling. Use only in a well ventilated area. Minimize dust generation and accumulation. Ground and bond containers when transferring material. Use spark-proof tools and explosion proof equipment. Avoid contact with eyes, skin, and clothing. Empty containers retain product residue, (liquid and/or vapor), and can be dangerous. Keep container tightly closed. Avoid contact with heat, sparks and flame. Avoid ingestion and inhalation. Do not pressurize, cut, weld, braze, solder, drill, grind, or expose empty containers to heat, sparks or open flames.; View all

4.4 Toxicity: 1. mammal (species unspecified) LD50 oral > 5gm/kg (5000mg/kg)
?? National Technical Information Service. Vol. OTS0538278.
2. mammal (species unspecified) LD50 skin > 2gm/kg (2000mg/kg)
?? National Technical Information Service. Vol. OTS0538278.?
3. 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.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Flammable liquids, Category 2

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Acute toxicity - Inhalation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H225 Highly flammable liquid and vapour H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation H330 Fatal if inhaled
Precautionary statement(s)
Prevention	P210 Keep away from heat, hot surfaces, sparks, open flames and other ignition sources. No smoking. P233 Keep container tightly closed. P240 Ground and bond container and receiving equipment. P241 Use explosion-proof [electrical/ventilating/lighting/...] equipment. P242 Use non-sparking tools. P243 Take action to prevent static discharges. P280 Wear protective gloves/protective clothing/eye protection/face protection. P264 Wash ... thoroughly after handling. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection.
Response	P303+P361+P353 IF ON SKIN (or hair): Take off immediately all contaminated clothing. Rinse skin with water [or shower]. P370+P378 In case of fire: Use ... to extinguish. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P310 Immediately call a POISON CENTER/doctor/\u2026 P320 Specific treatment is urgent (see ... on this label).
Storage	P403+P235 Store in a well-ventilated place. Keep cool. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

IR : liquid film

Mass

7. Synthesis Route

24424-99-5Total: 11 Synthesis Route

124-38-9 151 Suppliers

24424-99-5 447 Suppliers

Literatures:
Ciba Specialty Chemicals Corporation Patent: US6359122 B1, 2002 ; Location in patent: Example 1 ;
Yield: ~83%

24424-95-1 1 Suppliers

24424-99-5 447 Suppliers

Literatures:
Tetrahedron Letters, , vol. 31, # 19 p. 2697 - 2700
Yield: null

125260-47-1

24424-99-5 447 Suppliers

4859-16-9

Literatures:
Tetrahedron, , vol. 45, # 12 p. 3975 - 3992
Yield: null

View all

8. Precursor and Product

precursor:

4637-24-5

125260-47-1

124-38-9

865-47-4

4086-73-1

865-48-5

104-74-5

24424-95-1

478623-90-4

product :

2419-94-5

712-95-8

3392-12-9

762-75-4

4976-88-9

3303-84-2

870-46-2

2900-27-8

4888-33-9

7733-29-1

3350-20-7

3392-07-2

4326-36-7

3262-72-4

3422-01-3

7150-72-3

2766-43-0

2488-15-5

6404-29-1

870-50-8

3392-10-7

3978-80-1

4248-19-5

2592-19-0

3674-06-4

View all

9. Other Information

9.0 Usage: Reagent for the introduction of the Boc protecting group.Di-tert-butyl dicarbonate is a reagent used for the introduction of BOC protecting group. 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.

9.1 BRN: 1911173

9.2 Chemical Properties: White to off-white microcrystalline powder

9.3 Chemical Properties: Di-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.; View all

9.4 Uses: Reagent commonly used in organic chemistry for the introduction of the BOC protecting group.

9.5 Uses: reagent for t-BOC-protected amines

9.6 Uses: Reagent for the preparation of Boc-amino acids and peptides in high yields.

9.7 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.

10. Computational chemical data

Molecular Weight: 218.249g/mol
Molecular Formula: C₁₀H₁₈O₅
Compound Is Canonicalized: True
XLogP3-AA: 2.7
Exact Mass: 218.11542367
Monoisotopic Mass: 218.11542367
Complexity: 218
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 61.8
Heavy Atom Count: 15
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADceBwOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAAAAAADESAgAACCAAABAAIAAAACAAAAAAAAAAAAAAAAAAQAAAAAAAgAAAAAAAEAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

What Makes Di-tert-butyl Dicarbonate a Versatile Carboxylating Reagent? Apr 13 2024
Di-tert-butyl dicarbonate (Boc-anhydride) is a commonly used reagent in organic chemistry, known for its efficiency in introducing the tert-butoxycarbonyl (BOC) protecting group for amines. It also se..
How to prepare Boc acid anhydride (Di-tert-butyl dicarbonate)? Jul 05 2022
Background and overview[1] Di-tert-butyl dicarbonate (Boc acid anhydride) is an amino protective agent in the process of organic synthesis. It is mostly used in the synthesis of special proteins, pept..
Is Di-tert-butyl dicarbonate stable? Jun 28 2022
Di-tert-butyl dicarbonate is widely used in various fields such as food and medicine. It is a newly emerged amino protecting agent that promotes product synthesis. It is usually colorless and exists i..
Can carboxylic acids and non-nucleophilic N-containing heterocyclic amines undergo condensation with Boc2O? Feb 20 2021
Background introductionAs an important functional group, amide bonds are widely found in natural products, proteins and other substances. To date, there are many reports on amide bond formation. Howev..

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