1,1'-Carbonyldiimidazole Property

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.

pka

2.90±0.10(Predicted)

form 

Crystalline Powder

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.

InChIKey

PFKFTWBEEFSNDU-UHFFFAOYSA-N

CAS DataBase Reference

530-62-1(CAS DataBase Reference)

EPA Substance Registry System

1H-Imidazole, 1,1'-carbonylbis- (530-62-1)

Safety

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 

T

HazardClass 

8

PackingGroup 

III

HS Code 

29332990

Toxicity

LD50 orally in Rabbit: 1071 mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

Precautionary statements

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

1,1'-Carbonyldiimidazole Chemical Properties,Usage,Production

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.

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.

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.

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.

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.