1,1'-Carbonyldiimidazole supplier

Name
1,1'-Carbonyldiimidazole
EINECS 208-488-9
CAS No. 530-62-1
Article Data33
CAS DataBase
Density 1.39 g/cm³
Solubility Insoluble in water
Melting Point 117-122 °C(lit.)
Formula C₇H₆N₄O
Boiling Point 394.6 °C at 760 mmHg
Molecular Weight 162.151
Flash Point 192.5 °C
Transport Information UN 3263 8/PG 2
Appearance white crystalline powder
Safety 26-36/37/39-45-37/39-27
Risk Codes 22-34-36/37/38
Molecular Structure
Hazard Symbols C,Xi
Synonyms N,N-Carbonylbis(imidazole);1-Oxomethylenebis(N-imidazole);Diimidazol-1-yl ketone;N, N-Carbonylbis (imidazole);Carbonyl diimidazole;1,1-Carbonylbis-1H-imidazole;1H-Imidazole, 1,1-carbonylbis-;1H-imidazole, 1-(1H-imidazol-1-ylcarbonyl)-;1,1'-Carbonyldiimidazole (CDI);Imidazole, 1,1-carbonyldi- (8CI);Carbonyldiimidazole;N,N'-Carbonyldiimidazole;
PSA 52.71000
LogP 0.59600

Synthetic route

: 74731-19-4
1-imidazolylcarbonyl chloride

: 18156-74-6
1-(Trimethylsilyl)imidazole

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
at 20 - 35℃;	97.8%

: 288-32-4
1H-imidazole

: 68-12-2, 33513-42-7
N,N-dimethyl-formamide

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
With bromobenzene; copper(II) oxide; potassium hydroxide at 110℃; for 5h; Reagent/catalyst; Temperature;	96%

: 32315-10-9
bis(trichloromethyl) carbonate

: 18156-74-6
1-(Trimethylsilyl)imidazole

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In dichloromethane at 26℃; for 0.5h; Temperature; Inert atmosphere;	90.5%

: 288-32-4
1H-imidazole

: 503-38-8
trichloromethyl chloroformate

A: 1467-16-9
Imidazole hydrochloride

B: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In tetrahydrofuran at 20 - 55℃; for 4h; Product distribution / selectivity;	A n/a B 90%

...Expand

: 288-32-4
1H-imidazole

: 75-44-5
phosgene

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
With sodium hydroxide In water; chlorobenzene	88%
In acetone at 45℃; for 1.5h; Product distribution / selectivity;	71%
In xylene at 66 - 130℃; for 1.75h; Product distribution / selectivity;	70%

: 288-32-4
1H-imidazole

: 503-38-8
trichloromethyl chloroformate

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 2h; Product distribution / selectivity;	85%

: 288-32-4
1H-imidazole

: 75-44-5
phosgene

methanolic sodium methoxide: methanolic sodium methoxide

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In chlorobenzene	84%
In chlorobenzene	72.3%

...Expand

: 75-44-5
phosgene

: 18156-74-6
1-(Trimethylsilyl)imidazole

A: 74731-19-4
1-imidazolylcarbonyl chloride

B: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
-50 to -40 deg C, then r.t.;	A 81% B 17.2%
-50 to -40 deg C, then r.t.;	A 81% B 17.2%

...Expand

: 288-32-4
1H-imidazole

: 75-44-5
phosgene

A: 1467-16-9
Imidazole hydrochloride

B: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In xylene at 66 - 130℃; for 1.45h; Product distribution / selectivity;	A n/a B 70%
In chloroform at 35 - 55℃; for 3.25 - 3.75h; Product distribution / selectivity;	A n/a B 61.9%
In dichloromethane at 35℃; for 3.25h; Product distribution / selectivity;	A n/a B 59.9%

...Expand

: 288-32-4
1H-imidazole

: 67-66-3
chloroform

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
With 2,6-dimethylpyridine; oxygen at 20 - 50℃; for 0.5h; Irradiation;	38%

: 288-32-4
1H-imidazole

: 32315-10-9
bis(trichloromethyl) carbonate

: argon

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In dichloromethane

...Expand

: 288-32-4
1H-imidazole

: 32315-10-9
bis(trichloromethyl) carbonate

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
In tetrahydrofuran; dry-tetrahydrofuran

: 288-32-4
1H-imidazole

: 75-44-5
phosgene

: 6309-30-4
tri-n-butylamine hydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
Stage #1: tri-n-butylamine hydrochloride With sodium hydroxide In water; xylene pH=12; 40 % aq. NaOH; Stage #2: 1H-imidazole; phosgene In xylene at 65℃; for 1h; Phosgene was passed over the mixture at 72-83 °ree;C over 30 min; Under Ar;

...Expand

: 288-32-4
1H-imidazole

: 75-44-5
phosgene

Reaxys ID: 19827342: Reaxys ID: 19827342

A Reaxys ID: 19827340: Reaxys ID: 19827340

B: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
at 60 - 80℃;

...Expand

: 288-32-4
1H-imidazole

bisphenol A-polycarbonate: bisphenol A-polycarbonate

A: 80-05-7
BPA

B: 530-62-1
1,1'-carbonyldiimidazole

Conditions

Conditions	Yield
With zinc(II) oxide; tetrabutyl-ammonium chloride In tetrahydrofuran at 100℃; under 760.051 Torr; for 7h; Autoclave; Inert atmosphere;

...Expand

: 103-82-2
phenylacetic acid

: 530-62-1
1,1'-carbonyldiimidazole

: 55628-82-5
1-(Phenylacetyl)imidazole

Conditions

Conditions	Yield
In tetrahydrofuran for 1h; Inert atmosphere;	100%
In dichloromethane for 4h; Ambient temperature;	94%
In dichloromethane at 20 - 25℃; for 15h;	94%

: 693-23-2
1,12-dodecanedioic acid

: 530-62-1
1,1'-carbonyldiimidazole

: 122236-61-7
1,12-Di-imidazol-1-yl-dodecane-1,12-dione

Conditions

Conditions	Yield
In neat (no solvent) for 2h;	100%
In N,N-dimethyl acetamide at 40℃;
In tetrahydrofuran for 24h; Ambient temperature;
In tetrahydrofuran

: 331-39-5
caffeic acid

: 530-62-1
1,1'-carbonyldiimidazole

: 863107-05-5
caffeic acid imidazolide

Conditions

Conditions	Yield
In tetrahydrofuran 1) room temp, 1.5 h, caution: heavy gas production, 2) reflux, 2 h;	100%
In N,N-dimethyl-formamide for 2h; Ambient temperature;

: 38116-61-9
6-Methylpyrid-2-one-3-carboxylic Acid

: 530-62-1
1,1'-carbonyldiimidazole

: 88252-29-3
3-(N-imidazolyl-carbonyl)-6-methyl-2-pyridone

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 55℃; for 2.5h;	100%

: 115131-72-1
isopropyl (2S,3S)-3-amino-4-cyclohexyl-2-hydroxybutyrate hydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

: 126832-10-8
(4S,5S)-4-(cyclohexylmethyl)-5-(isopropoxycarbonyl)-2-oxazolidinone

Conditions

Conditions	Yield
With triethylamine In chloroform for 4h; Ambient temperature;	100%
In dichloromethane Yield given;

: 1-((1S,3S,5R)-3-Benzyloxy-5-methoxymethoxy-4-methylene-cyclohexyl)-ethane-1,2-diol

: 530-62-1
1,1'-carbonyldiimidazole

: 122940-88-9, 123049-34-3
4-((1S,3S,5R)-3-Benzyloxy-5-methoxymethoxy-4-methylene-cyclohexyl)-[1,3]dioxolan-2-one

Conditions

Conditions	Yield
In benzene Heating;	100%

: 82495-51-0
(2E)-5-(tert-butyldiphenylsilyloxy)-3-methylpent-2-enoic acid

: 530-62-1
1,1'-carbonyldiimidazole

: 82495-54-3
(E)-5-(tert-Butyl-diphenyl-silanyloxy)-1-imidazol-1-yl-3-methyl-pent-2-en-1-one

Conditions

Conditions	Yield
In tetrahydrofuran Ambient temperature;	100%

: 137175-16-7
(1β,2α,12α,16β)-20-(tert-butyldiphenylsiloxy)-1,2-dihydroxy-16-methoxy-12-(methoxymethoxy)picrasan-11-one

: 530-62-1
1,1'-carbonyldiimidazole

: 137175-17-8
C40H54O9Si

Conditions

Conditions	Yield
With dmap In dichloromethane 1) 0 deg C, 12.5 h, 2) RT, 1.5 h;	100%

: 76405-12-4
S-tert-butyl hydrogen 4-hydroxy-3,4-dimethyl-1-thioglutarate acetate

: 530-62-1
1,1'-carbonyldiimidazole

: 76405-13-5
S-tert-butyl γ-hydroxy-β,γ-dimethyl-δ-oxoimidazole-1-thiovalerate acetate

Conditions

Conditions	Yield
In tetrahydrofuran for 3.5h; Ambient temperature;	100%

: 73763-39-0
ADP tributylammonium salt

: 530-62-1
1,1'-carbonyldiimidazole

: 86342-06-5
ADP-imidazolate

Conditions

Conditions	Yield
In N,N-dimethyl-formamide for 4h; Ambient temperature;	100%

: 143870-63-7
(3R)-(-)-3-hydroxy-2-methylamino-3-phenylpropionitrile hydrochloride

: 530-62-1
1,1'-carbonyldiimidazole

: 143771-17-9
(5R)-(+)-4-carbonitrile-3-methyl-5-phenyloxazolidin-2-one

Conditions

Conditions	Yield
With triethylamine Ambient temperature;	100%

: 71557-89-6
12-(tert-butyl)dimethylsilyloxydrim-7-ene-9,11-diol

: 530-62-1
1,1'-carbonyldiimidazole

: 71557-90-9
9α,11-carbonyldioxy-12-(tert-butyl)dimethyl-silyldrim-7-ene

Conditions

Conditions	Yield
In benzene for 0.5h; Heating;	100%

: C48H80N2O15

: 530-62-1
1,1'-carbonyldiimidazole

: C49H78N2O16

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 60℃;	100%

: C14H20O8

: 530-62-1
1,1'-carbonyldiimidazole

: 148706-58-5
C15H18O9

Conditions

Conditions	Yield
In dichloromethane	100%

: 154047-18-4
(1-Allyl-1H-pyrrol-2-yl)-phenyl-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(1-Allyl-1H-pyrrol-2-yl)-phenyl-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: [((E)-1-But-2-enyl)-1H-pyrrol-2-yl]-phenyl-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-{[((E)-1-But-2-enyl)-1H-pyrrol-2-yl]-phenyl-methyl}-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: (4-Phenyl-1H-pyrrol-3-yl)-thiophen-3-yl-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(4-Phenyl-1H-pyrrol-3-yl)-thiophen-3-yl-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 20h; Ambient temperature;	100%

: (3,5-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(3,5-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: (3,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(3,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: 944657-10-7
(2,6-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(2,6-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: 944656-13-7
(2,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(2,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: (3,4-Dichloro-phenyl)-(1-propyl-1H-pyrrol-2-yl)-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 1-[(3,4-Dichloro-phenyl)-(1-propyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 2h; Ambient temperature;	100%

: 156026-71-0
[N-(phenylsulfonyl)-pyrrol-3-yl]-(4-methylphenyl)-methanol

: 530-62-1
1,1'-carbonyldiimidazole

: 156026-75-4
1-[(1-Benzenesulfonyl-1H-pyrrol-3-yl)-p-tolyl-methyl]-1H-imidazole

Conditions

Conditions	Yield
In acetonitrile for 3h; Ambient temperature;	100%
	100%

: 530-62-1
1,1'-carbonyldiimidazole

: 188443-86-9
(2S,3E)-2-(4-Methoxybenzylthio)-2-methylpent-3-enoic acid

: 114191-23-0
1-<(2S,3E)-2-(4-Methoxybenzylthio)-2-methylpent-3-enoyl>imidazole

Conditions

Conditions	Yield
In tetrahydrofuran for 18h;	100%
	95%

: 530-62-1
1,1'-carbonyldiimidazole

: 75-65-0
tert-butyl alcohol

: 49761-82-2
tert-butyl 1H-imidazole-1-carboxylate

Conditions

Conditions	Yield
potassium hydroxide In toluene at 60℃;	100%
In toluene at 20 - 60℃; for 6h; Inert atmosphere;	95%
With potassium hydroxide In toluene at 60℃; for 4h;	92%

: 530-62-1
1,1'-carbonyldiimidazole

: 129056-30-0
1-[(4E,6S,8E,10E,12E)-4,6,12-Trimethyltetradecatetra-4,8,10,12-enoyl]imidazole

Conditions

Conditions	Yield
In tetrahydrofuran	100%

: 2393-23-9
4-methoxy-benzylamine

: 530-62-1
1,1'-carbonyldiimidazole

: N-(1H-imidazol-1-ylcarbonyl)-4-methoxybenzylamine

Conditions

Conditions	Yield
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.166667h; Stage #2: 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 0℃; for 0.116667h;	100%
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In 1,4-dioxane; dichloromethane at 20℃; for 0.0833333h; Inert atmosphere; Stage #2: 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide for 2h; Inert atmosphere;	98%
Stage #1: 4-methoxy-benzylamine With hydrogenchloride In dichloromethane; isopropyl alcohol Stage #2: 1,1'-carbonyldiimidazole In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol at 20℃; for 1.5h;	87%

: 6117-80-2
1,4-butenediol

: 530-62-1
1,1'-carbonyldiimidazole

: 1026530-53-9
1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 3h; Inert atmosphere;	100%
In tetrahydrofuran for 24h; Ambient temperature;	85%
In dichloromethane at 20℃; Inert atmosphere;	84.7%

: 79-31-2
isobutyric Acid

: 530-62-1
1,1'-carbonyldiimidazole

: 4122-53-6
1-(1H-imidazol-1-yl)-2-methylpropan-1-one

Conditions

Conditions	Yield
In tetrahydrofuran	100%
In tetrahydrofuran Heating;
In N,N-dimethyl-formamide for 3h; Ambient temperature;

: 122-97-4
3-Phenyl-1-propanol

: 530-62-1
1,1'-carbonyldiimidazole

: 170895-01-9
1-(3-phenylpropoxycarbonyl)-1H-imidazole

Conditions

Conditions	Yield
In dichloromethane for 1h; Ambient temperature;	100%
In tetrahydrofuran at 23℃; for 14h;	93%
In dichloromethane at 20℃;
Stage #1: 3-Phenyl-1-propanol; 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Molecular sieve; Stage #2: With Pyridine hydrobromide In dichloromethane Solvent; Reagent/catalyst; Reflux; Molecular sieve;

1,1'-Carbonyldiimidazole Specification

1,1'-Carbonyldiimidazole, its cas register number is 530-62-1. It also can be called 1-Oxomethylenebis(N-imidazole); Carbonyl diimidazole; Diimidazol-1-yl ketone; N,N'-Carbonylbis(imidazole); 1,1'-Carbonylbis-1H-imidazole; 1H-Imidazole, 1,1'-carbonylbis-; Imidazole, 1,1'-carbonyldi- (8CI); Methanone, di-1H-imidazol-1-yl-. It is a white crystalline powder.The product categories is Amide; blocks; BuildingBlocks; Imidazoles; Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines; Peptide Coupling Reagents; Biochemistry; Condensation & Active Esterification; Coupling Reactions (Peptide Synthesis); Peptide Synthesis; Synthetic Organic Chemistry. It is often used for the coupling of amino acids for peptide synthesis and as a reagent in organic synthesis.

Physical properties about 1,1'-Carbonyldiimidazole are: (1)ACD/LogP: -0.657; (2)ACD/LogD (pH 5.5): -0.66; (3)ACD/LogD (pH 7.4): -0.66; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 10.43; (7)ACD/KOC (pH 7.4): 10.46; (8)#H bond acceptors: 5; (9)Index of Refraction: 1.691; (10)Molar Refractivity: 44.576 cm³; (11)Molar Volume: 116.453 cm³; (12)Polarizability: 17.671 10-24cm³; (13)Surface Tension: 63.2849998474121 dyne/cm; (14)Density: 1.392 g/cm³; (15)Flash Point: 192.47 °C; (16)Enthalpy of Vaporization: 64.469 kJ/mol; (17)Boiling Point: 394.638 °C at 760 mmHg

Preparation of 1,1'-Carbonyldiimidazole: 1,1'-Carbonyldiimidazole can be prepared straightforwardly by the reaction of phosgene with four equivalents of imidazole under anhydrous conditions. Removal of the side product, imidazolium chloride, and solvent results in the crystalline product in ~90% yield. 4 C₃H₄N₂ + C(O)Cl₂ → (C₃H₃N₂)₂CO + 2 [C₃H₃N₂H₂]Cl

Uses of 1,1'-Carbonyldiimidazole: 1,1'-Carbonyldiimidazole is often used for the coupling of amino acids for peptide synthesis and as a reagent in organic synthesis.Also it is used as a pharmaceutical intermediates.

When you are using this chemical, please be cautious about it as the following:
1. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice;
2. Wear suitable protective clothing, gloves and eye/face protection;
3. In case of accident or if you feel unwell, seek medical advice immediately (show label where possible);
4. Wear suitable gloves and eye/face protection;

You can still convert the following datas into molecular structure:
(1)InChI=1S/C7H6N4O/c12-7(10-3-1-8-5-10)11-4-2-9-6-11/h1-6H;
(2)InChIKey=PFKFTWBEEFSNDU-UHFFFAOYSA-N;
(3)Smilesc1nccn1C(=O)n1cncc1;

Product Name

1,1'-Carbonyldiimidazole

Synthetic route

1,1'-Carbonyldiimidazole Specification

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