530-62-1

Basic information

• Product Name: N,N'-Carbonyldiimidazole
• Synonyms: CARBONYLDIIMIDAZOLE;CARBODIIMIDAZOLE;LABOTEST-BB LT00233203;IM2 C O;DI(1H-IMIDAZOL-1-YL)METHANONE;CDI;(DIIMIDAZOL-1-YL)KETONE;AKOS BBS-00004316
• CAS NO: 530-62-1
• Molecular Formula: C₇H₆N₄O
• Molecular Weight: 162.15
• EINECS: 208-488-9
• Product Categories: AMIDE;blocks;BuildingBlocks;Imidazoles;Imidazoles, Pyrroles, Pyrazoles, Pyrrolidines;Peptide Coupling Reagents;Biochemistry;Condensation & Active Esterification;Coupling Reactions (Peptide Synthesis);Peptide Synthesis;Synthetic Organic Chemistry;Peptide;Heterocycles;Intermediates;Zero-Length Crosslinker;pharma material
• Mol File: 530-62-1.mol

Chemical Properties

• Melting Point: 117-122 °C(lit.)
• Boiling Point: 288.83°C (rough estimate)
• Flash Point: 192.5 °C
• Appearance: White to light cream/Crystalline Powder
• 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)
• Water Solubility: Insoluble in water
• Sensitive: Moisture Sensitive
• Stability: Stable, but moisture-sensitive. Incompatible with acids, strong oxidizing agents, water.
• Merck: 14,1819
• BRN: 6826
• CAS DataBase Reference: N,N'-Carbonyldiimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-Carbonyldiimidazole(530-62-1)
• EPA Substance Registry System: N,N'-Carbonyldiimidazole(530-62-1)

Safety Data

• Hazard Codes: C,Xi,Xn
• 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
• TSCA: T
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 530-62-1(Hazardous Substances Data)

Synthetic route

1-imidazolylcarbonyl chloride (74731-19-4) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 1,1'-carbonyldiimidazole (530-62-1)

Conditions	Yield
at 20 - 35℃;	97.8%

1H-imidazole (288-32-4) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 1,1'-carbonyldiimidazole (530-62-1)

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

bis(trichloromethyl) carbonate (32315-10-9) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 1,1'-carbonyldiimidazole (530-62-1)

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

1H-imidazole (288-32-4) + trichloromethyl chloroformate (503-38-8) → Imidazole hydrochloride (1467-16-9) + 1,1'-carbonyldiimidazole (530-62-1)

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

1H-imidazole (288-32-4) + phosgene (75-44-5) → 1,1'-carbonyldiimidazole (530-62-1)

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%

1H-imidazole (288-32-4) + trichloromethyl chloroformate (503-38-8) → 1,1'-carbonyldiimidazole (530-62-1)

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

1H-imidazole (288-32-4) + phosgene (75-44-5) + methanolic sodium methoxide → 1,1'-carbonyldiimidazole (530-62-1)

Conditions	Yield
In chlorobenzene	84%
In chlorobenzene	72.3%

phosgene (75-44-5) + 1-(Trimethylsilyl)imidazole (18156-74-6) → 1-imidazolylcarbonyl chloride (74731-19-4) + 1,1'-carbonyldiimidazole (530-62-1)

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%

1H-imidazole (288-32-4) + phosgene (75-44-5) → Imidazole hydrochloride (1467-16-9) + 1,1'-carbonyldiimidazole (530-62-1)

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%

1H-imidazole (288-32-4) + chloroform (67-66-3) → 1,1'-carbonyldiimidazole (530-62-1)

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

1H-imidazole (288-32-4) + bis(trichloromethyl) carbonate (32315-10-9) + argon → 1,1'-carbonyldiimidazole (530-62-1)

Conditions	Yield
In dichloromethane

1H-imidazole (288-32-4) + bis(trichloromethyl) carbonate (32315-10-9) → 1,1'-carbonyldiimidazole (530-62-1)

Conditions	Yield
In tetrahydrofuran; dry-tetrahydrofuran

1H-imidazole (288-32-4) + phosgene (75-44-5) + tri-n-butylamine hydrochloride (6309-30-4) → 1,1'-carbonyldiimidazole (530-62-1)

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;

1H-imidazole (288-32-4) + phosgene (75-44-5) + Reaxys ID: 19827342 → Reaxys ID: 19827340 + 1,1'-carbonyldiimidazole (530-62-1)

Conditions	Yield
at 60 - 80℃;

1H-imidazole (288-32-4) + bisphenol A-polycarbonate → BPA (80-05-7) + 1,1'-carbonyldiimidazole (530-62-1)

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

phenylacetic acid (103-82-2) + 1,1'-carbonyldiimidazole (530-62-1) → 1-(Phenylacetyl)imidazole (55628-82-5)

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

1,12-dodecanedioic acid (693-23-2) + 1,1'-carbonyldiimidazole (530-62-1) → 1,12-Di-imidazol-1-yl-dodecane-1,12-dione (122236-61-7)

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

caffeic acid (331-39-5) + 1,1'-carbonyldiimidazole (530-62-1) → caffeic acid imidazolide (863107-05-5)

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;

6-Methylpyrid-2-one-3-carboxylic Acid (38116-61-9) + 1,1'-carbonyldiimidazole (530-62-1) → 3-(N-imidazolyl-carbonyl)-6-methyl-2-pyridone (88252-29-3)

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

isopropyl (2S,3S)-3-amino-4-cyclohexyl-2-hydroxybutyrate hydrochloride (115131-72-1) + 1,1'-carbonyldiimidazole (530-62-1) → (4S,5S)-4-(cyclohexylmethyl)-5-(isopropoxycarbonyl)-2-oxazolidinone (126832-10-8)

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 + 1,1'-carbonyldiimidazole (530-62-1) → 4-((1S,3S,5R)-3-Benzyloxy-5-methoxymethoxy-4-methylene-cyclohexyl)-[1,3]dioxolan-2-one (122940-88-9, 123049-34-3)

Conditions	Yield
In benzene Heating;	100%

(2E)-5-(tert-butyldiphenylsilyloxy)-3-methylpent-2-enoic acid (82495-51-0) + 1,1'-carbonyldiimidazole (530-62-1) → (E)-5-(tert-Butyl-diphenyl-silanyloxy)-1-imidazol-1-yl-3-methyl-pent-2-en-1-one (82495-54-3)

Conditions	Yield
In tetrahydrofuran Ambient temperature;	100%

(1β,2α,12α,16β)-20-(tert-butyldiphenylsiloxy)-1,2-dihydroxy-16-methoxy-12-(methoxymethoxy)picrasan-11-one (137175-16-7) + 1,1'-carbonyldiimidazole (530-62-1) → C40H54O9Si (137175-17-8)

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

S-tert-butyl hydrogen 4-hydroxy-3,4-dimethyl-1-thioglutarate acetate (76405-12-4) + 1,1'-carbonyldiimidazole (530-62-1) → S-tert-butyl γ-hydroxy-β,γ-dimethyl-δ-oxoimidazole-1-thiovalerate acetate (76405-13-5)

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

ADP tributylammonium salt (73763-39-0) + 1,1'-carbonyldiimidazole (530-62-1) → ADP-imidazolate (86342-06-5)

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

(3R)-(-)-3-hydroxy-2-methylamino-3-phenylpropionitrile hydrochloride (143870-63-7) + 1,1'-carbonyldiimidazole (530-62-1) → (5R)-(+)-4-carbonitrile-3-methyl-5-phenyloxazolidin-2-one (143771-17-9)

Conditions	Yield
With triethylamine Ambient temperature;	100%

12-(tert-butyl)dimethylsilyloxydrim-7-ene-9,11-diol (71557-89-6) + 1,1'-carbonyldiimidazole (530-62-1) → 9α,11-carbonyldioxy-12-(tert-butyl)dimethyl-silyldrim-7-ene (71557-90-9)

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

C48H80N2O15 + 1,1'-carbonyldiimidazole (530-62-1) → C49H78N2O16

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

C14H20O8 + 1,1'-carbonyldiimidazole (530-62-1) → C15H18O9 (148706-58-5)

Conditions	Yield
In dichloromethane	100%

(1-Allyl-1H-pyrrol-2-yl)-phenyl-methanol (154047-18-4) + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(1-Allyl-1H-pyrrol-2-yl)-phenyl-methyl]-1H-imidazole

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

[((E)-1-But-2-enyl)-1H-pyrrol-2-yl]-phenyl-methanol + 1,1'-carbonyldiimidazole (530-62-1) → 1-{[((E)-1-But-2-enyl)-1H-pyrrol-2-yl]-phenyl-methyl}-1H-imidazole

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

(4-Phenyl-1H-pyrrol-3-yl)-thiophen-3-yl-methanol + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(4-Phenyl-1H-pyrrol-3-yl)-thiophen-3-yl-methyl]-1H-imidazole

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

(3,5-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(3,5-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

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

(3,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(3,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

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

(2,6-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol (944657-10-7) + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(2,6-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

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

(2,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methanol (944656-13-7) + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(2,4-Dichloro-phenyl)-(1-methyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

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

(3,4-Dichloro-phenyl)-(1-propyl-1H-pyrrol-2-yl)-methanol + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(3,4-Dichloro-phenyl)-(1-propyl-1H-pyrrol-2-yl)-methyl]-1H-imidazole

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

[N-(phenylsulfonyl)-pyrrol-3-yl]-(4-methylphenyl)-methanol (156026-71-0) + 1,1'-carbonyldiimidazole (530-62-1) → 1-[(1-Benzenesulfonyl-1H-pyrrol-3-yl)-p-tolyl-methyl]-1H-imidazole (156026-75-4)

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

1,1'-carbonyldiimidazole (530-62-1) + (2S,3E)-2-(4-Methoxybenzylthio)-2-methylpent-3-enoic acid (188443-86-9) → 1-<(2S,3E)-2-(4-Methoxybenzylthio)-2-methylpent-3-enoyl>imidazole (114191-23-0)

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

1,1'-carbonyldiimidazole (530-62-1) + tert-butyl alcohol (75-65-0) → tert-butyl 1H-imidazole-1-carboxylate (49761-82-2)

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%

1,1'-carbonyldiimidazole (530-62-1) → 1-[(4E,6S,8E,10E,12E)-4,6,12-Trimethyltetradecatetra-4,8,10,12-enoyl]imidazole (129056-30-0)

Conditions	Yield
In tetrahydrofuran	100%

4-methoxy-benzylamine (2393-23-9) + 1,1'-carbonyldiimidazole (530-62-1) → N-(1H-imidazol-1-ylcarbonyl)-4-methoxybenzylamine

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%

1,4-butenediol (6117-80-2) + 1,1'-carbonyldiimidazole (530-62-1) → 1,4-bis<(1-imidazolyl)carbonyloxy>-cis-2-butene (1026530-53-9)

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%

isobutyric Acid (79-31-2) + 1,1'-carbonyldiimidazole (530-62-1) → 1-(1H-imidazol-1-yl)-2-methylpropan-1-one (4122-53-6)

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

3-Phenyl-1-propanol (122-97-4) + 1,1'-carbonyldiimidazole (530-62-1) → 1-(3-phenylpropoxycarbonyl)-1H-imidazole (170895-01-9)

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;

Upstream product

• 288-32-4 1H-imidazole 
• 75-44-5 phosgene 
• 18156-74-6 1-(Trimethylsilyl)imidazole 
• 74731-19-4 1-imidazolylcarbonyl chloride 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 503-38-8 trichloromethyl chloroformate 
• 6309-30-4 tri-n-butylamine hydrochloride 
• 68-12-2 N,N-dimethyl-formamide 
• 67-66-3 chloroform 

Downstream Products

• 13589-08-7 meso-N,N'-carbonyl-bis-phenylalanine 
• 4192-77-2 ethyl cinnamate 
• 5649-76-3 1H-naphth<2,3-d>imidazol-2(3H)-one 
• 30189-51-6 ethyl (N-tert-butoxycarbonyl-L-phenylalanyl)glycinate 
• 1170-76-9 Z-Gly-(L)-Phe 
• 615-16-7 1,3-dihydro-2H-benzimidazol-2-one 
• 60330-99-6 3-[(2-oxo-4-phenyl-1,4-dihydro-2H-benzo[d][1,3]oxazin-4-ylmethyl)-amino]-but-2-enoic acid ethyl ester 
• 72543-04-5 3-(5-acetyl-2-hydroxy-phenyl)-[1,4,2]dioxazol-5-one 
• 35746-43-1 3-phenyl-5-phenyloxazol-2(3H)-one 
• 61416-47-5 3-methyl-5-phenyloxazol-2(3H)-one 
• 57500-97-7 2,8-dibenzyl-4a,10a-diphenyl-octahydro-dipyrimido[1,6-b;1',6'-e][1,4,2,5]dioxadiazine-1,7-dione 
• 57501-04-9 2,8-dibenzyl-4a,10a-bis-(4-methoxy-phenyl)-octahydro-dipyrimido[1,6-b;1',6'-e][1,4,2,5]dioxadiazine-1,7-dione 
• 47878-53-5 N,N'-Bis-(3-(3-(2-amidinoethylcarbamoyl)-phenylcarbamoyl)-phenyl)-harnstoff 
• 65739-79-9 4-(2-methoxy-anilino)-benzo[4,5]thieno[2,3-e][1,3]oxazin-2-one 

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PROCESS FOR PRODUCING N,N'-CARBONYLDIIMIDAZOLE

The present invention provides a process for producing N,N'-carbonyldiimidazole, comprising: reacting phosgene, diphosgene, or triphosgene with imidazole in an inert solvent to produce N,N'-carbonyldiimidazole; to imidazole hydrochloride yielded as a by-product in the above step, adding a gaseous or liquid basic compound represented by the below-shown general formula (1) in an inert solvent to conduct neutralization reaction; and circulating the imidazole thus generated to use it as a starting material for N,N'-carbonyldiimidazole production. In the general formula (1), R 1 , R 2 , and R 3 each independently represents a hydrogen atom, a methyl group, or an ethyl group. The CDI produced by the production process of the invention is a compound useful in the fields of synthesis of pharmaceutical agents, synthesis of agricultural chemicals, peptide synthesis, and the like, e.g., intermolecular condensation reactions, intramolecular condensation reactions for synthesizing N-carboxylic anhydrides, production of activated esters, and the like. The compound is especially suitable for use in applications where colorlessness is required.

Process for preparing N,N'-carbonyldiazoles

A process is provided for preparing N,N′-carbonyldiazoles by reacting azoles with phosgene in halogenated aliphatic hydrocarbon solvents, the entirety of the azole for reaction being introduced in the solvent, followed by the addition of phosgene.

METHOD FOR THE PRODUCTION OF N,N -CARBONYLDIAZOLES

Disclosed is a method for producing N,N'-carbonyldiazoles by reacting azoles with phosgene in polar solvents from the group comprising ethers, ketones, and chlorinated aliphatic solvents. According to the inventive method, the azole and the phosgene are dosed such that 0.17 to 0.37 mole of phosgene are dosed during the time one mole of azole is dosed.