ChemicalBook > CAS DataBase List > 1,1'-Carbonyldiimidazole

1,1'-Carbonyldiimidazole

Product Name
1,1'-Carbonyldiimidazole
CAS No.
530-62-1
Chemical Name
1,1'-Carbonyldiimidazole
Synonyms
CDI;CARBONYLDIIMIDAZOLE;1,1'-CARBONYLDIIMIDAZOLE (CDI);DI(1H-IMIDAZOL-1-YL)METHANONE;N,N-CARBONYLDIIMIDAZOLE;Diimidazolyl ketone;1,1-CARBONYL DIIMIDAZOLE;5% Pd-BaSO4;CARBODIIMIDAZOLE;Di-imidazol-1-yl-methanone
CBNumber
CB0215374
Molecular Formula
C7H6N4O
Formula Weight
162.15
MOL File
530-62-1.mol
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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)
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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
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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.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
8.02301
Product name
1,1′-Carbonyldiimidazole
Purity
for synthesis
Packaging
2G
Price
$32.9
Updated
2024/03/01
Sigma-Aldrich
Product number
8.51054
Product name
CDI
Purity
1,1′-Carbonyldiimidazole Novabiochem?
Packaging
25g
Price
$172
Updated
2024/03/01
Sigma-Aldrich
Product number
8.51054
Product name
CDI
Purity
1,1′-Carbonyldiimidazole Novabiochem?
Packaging
100g
Price
$514
Updated
2024/03/01
Sigma-Aldrich
Product number
8.02301
Product name
1,1′-Carbonyldiimidazole
Purity
for synthesis
Packaging
5G
Price
$34.1
Updated
2024/03/01
Sigma-Aldrich
Product number
8.02301
Product name
1,1′-Carbonyldiimidazole
Purity
for synthesis
Packaging
25G
Price
$124
Updated
2024/03/01
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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.

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.

1,1'-Carbonyldiimidazole Preparation Products And Raw materials

Raw materials

Imidazole

Preparation Products

2-(Boc-aminomethyl)-piperidine 3-oxo-3-phenyl-propanamide 5-(Pyridin-3-yl)-1H-pyrazole-3-carboxamide ,97% 3-Cyanomethylthiophene 4-AMINOMETHYL-BENZAMIDE 2,8-DICHLOROPYRIMIDO[5,4-D]PYRIMIDINE Progabide 2-AMINO-5-BROMOBENZAMIDE 2-Ethylpiperazine 6-FLUORO-1H-PYRAZOLO[3,4-B]PYRIDINE-3-CARBONITRILE Pazufloxacin 5-BROMOTHIOPHENE-2-CARBONITRILE N-Heptafluorobutyrylimidazole 4-(Boc-Aminomethyl)piperidine 8-METHOXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID AMIDE 2-chloro-5-cyanopyridine 7-HYDROXY-2-OXO-2H-CHROMENE-3-CARBOXYLIC ACID AMIDE 1-Boc-2-Methylpiperazine 3-(1H-INDOL-3-YL)-1-PROPANAMINE 1-(4-ACETYLPIPERIDINO)ETHAN-1-ONE 5-BROMO-2-BENZOXAZOLINONE 97 isoglutamine 3-BROMOTHIOPHENE-2-CARBOXAMIDE 1-Boc-4-(aminomethyl)piperidine 2,3-diaminonaphthalene 4-N-BOC-Aminopiperidine 5-AMINO-3-PYRIDINECARBONITRILE 4-Cyanopiperidine 1,3-THIAZOLIDIN-2-ONE
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View Lastest Price from 1,1'-Carbonyldiimidazole manufacturers

Jinan Finer Chemical Co., Ltd
Product
1,1'-Carbonyldiimidazole 530-62-1
Price
US $5.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
200mt
Release date
2022-02-24
WUHAN FORTUNA CHEMICAL CO., LTD
Product
1,1'-Carbonyldiimidazole 530-62-1
Price
US $0.00/KG
Min. Order
20KG
Purity
98%min
Supply Ability
30tons/month
Release date
2023-02-03
Hebei Mujin Biotechnology Co.,Ltd
Product
N,N'-Carbonyldiimidazole 530-62-1
Price
US $0.00/Kg/Bag
Min. Order
1Kg/Bag
Purity
99%
Supply Ability
5000kg/month
Release date
2021-10-14

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