ChemicalBook Product Catalog Biochemical Engineering Condensing agent 1,1'-Carbonyldiimidazole

1,1'-Carbonyldiimidazole

Product Name1,1'-Carbonyldiimidazole
CAS530-62-1
MFC7H6N4O
MW162.15
EINECS208-488-9
MOL File530-62-1.mol

Chemical Properties

Melting point	117-122 °C(lit.)
Boiling point	288.83°C (rough estimate)
Density	1.303 g/mL at 25 °C
vapor pressure	0.006-0.012Pa at 20-25℃
refractive index	n20/D1.434
storage temp.	2-8°C
solubility	Soluble in dimethylformamide.
form	Crystalline Powder
pka	2.90±0.10(Predicted)
color	White to light cream
PH Range	7.7 at 50 g/l
PH	7.7 (50g/l, H2O, 20℃)
Water Solubility	Insoluble in water
Sensitive	Moisture Sensitive
Merck	14,1819
BRN	6826
Stability	Stable, but moisture-sensitive. Incompatible with acids, strong oxidizing agents, water.
InChI	1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H
InChIKey	PFKFTWBEEFSNDU-UHFFFAOYSA-N
SMILES	O=C(n1ccnc1)n2ccnc2
CAS DataBase Reference	530-62-1(CAS DataBase Reference)
EPA Substance Registry System	1H-Imidazole, 1,1'-carbonylbis- (530-62-1)

Safety Information

Hazard Codes	C,Xi,Xn
Risk Statements	22-34-36/37/38-40-36/38
Safety Statements	26-36/37/39-45-37/39-27-36/37
RIDADR	UN 3263 8/PG 2
WGK Germany	2
F	10-21
Hazard Note	Harmful/Corrosive/Moisture Sensitive
TSCA	TSCA listed
HazardClass	8
PackingGroup	III
HS Code	29332990
Storage Class	8A - Combustible corrosive hazardous materials
Hazard Classifications	Acute Tox. 4 Oral Eye Dam. 1 Skin Corr. 1B
Toxicity	LD50 orally in Rabbit: 1071 mg/kg

MSDS

Provider	Language
1,1'-Carbonyldiimidazole	English
SigmaAldrich	English
ACROS	English
ALFA	English

Usage And Synthesis

Chemical Properties

The substance appears as a white to slightly pale-yellow crystalline powder with a melting point range of 115.5-116°C. It exhibits poor solubility in water, while displaying solubility in alcohol and ether.

Application

Peptide coupling reagent1,1'-Carbonyldiimidazole acts as a coupling reagent and utilized for coupling of amino acids in order to prepare peptide in organic synthesis. It is also used in the preparation of beta-keto sulfones, sulfoxides and beta-enamino acid derivatives. It is used to convert alcohols and amines into carbamates, esters, and ureas. It is involved in the preparation of formylized imidazole by reaction with formic acid. Further, it is used in the synthesis of dipolar polyamides compounds. In addition to this, it is considered as an equivalent of phosgene and used to prepare asymmetric bis alkyl carbonate.

Uses

CDI, also known as 1,1'-carbonyldiimidazole, is a commonly used peptide coupling reagent in the synthesis of peptides and nucleoside triphosphates. It usually contains approximately 10% imidazole and reacts rapidly with carboxylic acids to produce acyl imidazoles. Later, it readily reacts with amines to create amides. In addition, CDI is useful in converting alcohols and amines into a range of chemical compounds, including carbamates, esters, and ureas.

Preparation

1,1'-Carbonyldiimidazole has been prepared by the reaction of imidazole and phosgene in anhydrous benzene and anhydrous tetrahydrofuran. It has also been obtained by the reaction of 1-(trimethylsilyl)imidazole and phosgene in anhydrous benzene, but that method offers no advantages that justify the more extensive preparative effort required.
DOI: 10.15227/orgsyn.048.0044

General Description

1,1′-Carbonyldiimidazole (N,N′-carbonyldiimidazole) is a versatile peptide-forming reagent.

reaction suitability

reaction type: Coupling Reactions

Purification Methods

Crystallise it from *benzene or tetrahydrofuran in a dry-box and store it dry. [Hearn Methods Enzymol 135 102 1987, Beilstein 23/4 V 245.]

Precautions

1,1'-Carbonyldiimidazole is incompatible with oxidizing agents and strong acids and should not be stored or handled near them. Store in a refrigerator, under inert gas and protected from moisture. This substance is heat sensitive and moisture sensitive.

References

[1] Journal of Nanoscience and Nanotechnology, 2018, vol. 18, # 1, p. 234 - 241

Preparation Products And Raw materials