Di-tert-butyl dicarbonate Properties

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)
EWG's Food Scores	1
FDA UNII	Z10Q236C3G
EPA Substance Registry System	Dicarbonic acid, bis(1,1-dimethylethyl) ester (24424-99-5)

SAFETY

Risk and Safety Statements

Symbol(GHS)

GHS02,GHS05,GHS06

Signal word

Danger

Hazard statements

H226-H315-H317-H318-H330-H335

Precautionary statements

P210-P233-P280-P303+P361+P353-P304+P340+P310-P305+P351+P338

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

NFPA 704

	3
4		1

Di-tert-butyl dicarbonate price More Price(70)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Sigma-Aldrich	8.52261	Di-tert-butyl dicarbonate Novabiochem?	24424-99-5	25g	$32.8	2024-03-01	Buy
Sigma-Aldrich	8.52261	Di-tert-butyl dicarbonate Novabiochem?	24424-99-5	100g	$87.9	2024-03-01	Buy
Sigma-Aldrich	34660	Di-tert-butyl dicarbonate ≥98.0% (GC)	24424-99-5	25g	$57.6	2024-03-01	Buy
Sigma-Aldrich	205249	Di-tert-butyl dicarbonate ReagentPlus , 99%	24424-99-5	10g	$53.8	2024-03-01	Buy
Sigma-Aldrich	34660	Di-tert-butyl dicarbonate ≥98.0% (GC)	24424-99-5	100g	$147	2024-03-01	Buy

Product number	Packaging	Price	Buy
8.52261	25g	$32.8	Buy
8.52261	100g	$87.9	Buy
34660	25g	$57.6	Buy
205249	10g	$53.8	Buy
34660	100g	$147	Buy

Di-tert-butyl dicarbonate Chemical Properties,Uses,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.

Definition

ChEBI: Di-tert-butyl dicarbonate is an acyclic carboxylic anhydride. It is functionally related to a dicarbonic acid.

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%.

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 synthesis

Synthesis of Di-tert-butyl dicarbonate from Di-tert-butyl Tricarbonate

Di-tert-butyl dicarbonate Preparation Products And Raw materials

Raw materials

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

Tetrahydrofuran

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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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Di-tert-butyl dicarbonate Suppliers

Global( 1007)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Shanghai Time Chemicals CO., Ltd.	+86-021-57951555 +8617317452075	jack.li@time-chemicals.com	China	1803	55
SIMAGCHEM CORP	+86-13806087780	sale@simagchem.com	China	17365	58
Neostar United (Changzhou) Industrial Co., Ltd.	+86-0519-85551759 +8613506123987	marketing1@neostarunited.com	China	8838	58
Shandong Zhishang New Material Co., Ltd.	+8617653113209	sales002@sdzschem.com	China	3049	58
Chemtour Biotech Co., Ltd	+8617327281506	market@chemtour.com	China	1460	58
GenChem & GenPharm (Changzhou) Co., Ltd.	+86-86020003 +86-18861157602	sales03@genchem.cn	China	104	58
ZHEJIANG JIUZHOU CHEM CO., LTD	+86-0576225566889 +86-13454675544	admin@jiuzhou-chem.com；jamie@jiuzhou-chem.com；alice@jiuzhou-chem.com	China	12272	58
Hebei Weibang Biotechnology Co., Ltd	+8615531157085	abby@weibangbio.com	China	8810	58
Hebei Mojin Biotechnology Co., Ltd	+86 13288715578 +8613288715578	sales@hbmojin.com	China	12837	58
Hebei Chuanghai Biotechnology Co,.LTD	+86-13131129325	sales1@chuanghaibio.com	China	5889	58

Supplier	Advantage
Shanghai Time Chemicals CO., Ltd.	55
SIMAGCHEM CORP	58
Neostar United (Changzhou) Industrial Co., Ltd.	58
Shandong Zhishang New Material Co., Ltd.	58
Chemtour Biotech Co., Ltd	58
GenChem & GenPharm (Changzhou) Co., Ltd.	58
ZHEJIANG JIUZHOU CHEM CO., LTD	58
Hebei Weibang Biotechnology Co., Ltd	58
Hebei Mojin Biotechnology Co., Ltd	58
Hebei Chuanghai Biotechnology Co,.LTD	58

View Lastest Price from Di-tert-butyl dicarbonate manufacturers

Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
2024-12-18	Di-tert-butyl dicarbonate 24424-99-5	US $10.00 / kg	1kg	99%	20ton	Hebei Zhuanglai Chemical Trading Co.,Ltd
2024-12-13	Di-tert-butyl dicarbonate 24424-99-5	US $0.00 / Kg/Drum	1KG	99%min	10 tons	WUHAN FORTUNA CHEMICAL CO., LTD
2024-12-11	Di-tert-butyl dicarbonate 24424-99-5	US $3.50 / kg	1kg	≥99%	3000tons/month	Hebei Andu Technology Com.,Ltd

Di-tert-butyl dicarbonate
24424-99-5
US $10.00 / kg
99%
Hebei Zhuanglai Chemical Trading Co.,Ltd

Di-tert-butyl dicarbonate
24424-99-5
US $0.00 / Kg/Drum
99%min
WUHAN FORTUNA CHEMICAL CO., LTD

Di-tert-butyl dicarbonate
24424-99-5
US $3.50 / kg
≥99%
Hebei Andu Technology Com.,Ltd

Di-tert-butyl dicarbonate Spectrum

Di-tert-butyl dicarbonate(24424-99-5)MS Di-tert-butyl dicarbonate(24424-99-5)¹HNMR Di-tert-butyl dicarbonate(24424-99-5)¹³CNMR Di-tert-butyl dicarbonate(24424-99-5)IR1 Di-tert-butyl dicarbonate(24424-99-5)Raman

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Di-tert-butyl dicarbonate