1,1′-Carbonyldiimidazole

1,1′-Carbonyldiimidazole Basic information
Product Name:1,1′-Carbonyldiimidazole
Synonyms:LABOTEST-BB LT00233203;IM2 C O;(DIIMIDAZOL-1-YL)KETONE;AKOS BBS-00004316;RARECHEM AK HZ 0060;1,1′-CARBONYLBIS-1H-IMIDAZOLE;1.1′-CARBONYL-BIS-IMIDAZOLE;1,1′-CARBONYLDIIMIDAZOLE
CAS:530-62-1
MF:C7H6N4O
MW:162.15
EINECS:208-488-9
Product Categories:Zero-Length Crosslinker;blocks;BuildingBlocks;pharma material;AMIDE;Peptide;Heterocycles;Intermediates;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Peptide Coupling Reagents;Imidazoles;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry;530-62-1
Mol File:530-62-1.mol
1,1'-Carbonyldiimidazole Structure
1,1′-Carbonyldiimidazole 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
pka2.90±0.10(Predicted)
color White to light cream
PH7.7 (50g/l, H2O, 20℃)
PH Range7.7 at 50 g/l
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.
InChIKeyPFKFTWBEEFSNDU-UHFFFAOYSA-N
CAS DataBase Reference530-62-1(CAS DataBase Reference)
EPA Substance Registry System1H-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
10-21
Hazard Note Harmful/Corrosive/Moisture Sensitive
TSCA T
HazardClass 8
PackingGroup III
HS Code 29332990
ToxicityLD50 orally in Rabbit: 1071 mg/kg
MSDS Information
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1,1′-CarbonyldiimidazoleEnglish
SigmaAldrichEnglish
ACROSEnglish
ALFAEnglish
1,1′-Carbonyldiimidazole Usage And Synthesis
Chemical PropertiesThe 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.
UsesCDI, 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.
ApplicationPeptide 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.
Preparation1,1′-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 Description1,1′-Carbonyldiimidazole (N,N′-carbonyldiimidazole) is a versatile peptide-forming reagent.
Purification MethodsCrystallise it from *benzene or tetrahydrofuran in a dry-box and store it dry. [Hearn Methods Enzymol 135 102 1987, Beilstein 23/4 V 245.]
Precautions1,1′-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.
1,1′-Carbonyldiimidazole Preparation Products And Raw materials
Raw materialsImidazole–>N-(Trimethylsilyl)imidazole–>PHOSGENE–>Benzene
Preparation Products6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE–>1-Boc-4-(aminomethyl)piperidine–>2,8-DICHLOROPYRIMIDO[5,4-D]PYRIMIDINE–>2-Ethylpiperazine–>4-N-BOC-Aminopiperidine–>5-BROMO-2-BENZOXAZOLINONE 97–>Pazufloxacin–>isoglutamine–>2-chloro-5-cyanopyridine–>4-Cyanopiperidine–>1,3-THIAZOLIDIN-2-ONE–>2-AMINO-5-BROMOBENZAMIDE–>3-(1H-INDOL-3-YL)-1-PROPANAMINE–>3-BROMOTHIOPHENE-2-CARBOXAMIDE–>2,3-diaminonaphthalene–>1-Boc-2-Methylpiperazine–>5-AMINO-3-PYRIDINECARBONITRILE–>5-(Pyridin-3-yl)-1H-pyrazole-3-carboxamide ,97%–>2-(Boc-aminomethyl)-piperidine–>4-(Boc-Aminomethyl)piperidine–>8-METHOXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID AMIDE–>7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID AMIDE–>5-BROMOTHIOPHENE-2-CARBONITRILE–>1-(4-ACETYLPIPERIDINO)ETHAN-1-ONE–>4-AMINOMETHYL-BENZAMIDE–>3-oxo-3-phenyl-propanamide–>Progabide–>3-Cyanomethylthiophene–>N-Heptafluorobutyrylimidazole

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