530-62-1

Basic information

• Product Name: 1,1'-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
• Article Data: 22

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: 1,1'-Carbonyldiimidazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1'-Carbonyldiimidazole(530-62-1)
• EPA Substance Registry System: 1,1'-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)

Usage

Chemical Properties

White crystalline powder

Uses

Different sources of media describe the Uses of 530-62-1 differently. You can refer to the following data:
1. Used in the synthesis of peptides. Contains up to 10% imidazole.
2. peptide coupling reagent
3. CDI is mainly employed to convert alcohols and amines into carbamates, esters, and ureas. It is also used in the synthesis of peptides and nucleoside triphosphates.
4. 1,1'-Carbonyldiimidazole is a peptide coupling reagent,it is used in the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.
5. 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.

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.]

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

Downstream Products

• 14509-66-1 5,6,7,8-tetrahydro-5-oxoimidazo[1,5-c]pyrimidine 
• 130115-99-0 3,5-dimethyl-2,6-di-p-tolyl-4(1H)-pyridone 
• 126921-88-8 1-Benzyl-5-{[(imidazole-1-carbonyl)-amino]-methyl}-1H-imidazole-4-carboxylic acid amide 
• 130116-00-6 3,5-diethyl-2,6-diphenyl-4(1H)-pyridone 
• 77308-04-4 2-Benzyl-4-methyl-4-phenyl-[1,5,2]dioxazinane-3,6-dione 
• 93849-15-1 4-(2-chlorophenyl)-3-ethoxycarbonyl-2-{2-[N-(1-imidazolylcarbonyl)amino]ethoxymethyl}-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine 
• 128791-77-5 p-nitrobenzyl (2S,3S)-2-(imidazol-1-yl)carbonyloxymethyl-4-oxo-3-(phenylacetamido)azetidine-1-acetate 
• 20816-58-4 adenosine 5'-phosphorimidazolide 
• 56428-57-0 uridine 5’-monophosphate-imidazole 
• 2682-49-7 thiazolidine-2-one 
• 120743-65-9 (E)-1-<<<<5,6-bis<4-(tert-butyldimethylsiloxy)phenyl>-5-octen-1-yl>oxy>carbonyl>amino>-2-chloroethane 
• 7150-63-2 diethyl N,N'-carbonylbisglycinate 
• 151265-18-8 1,5-anhydro-6-O-(tert-butyldiphenylsilyl)-3,4-O-carbonate-2-deoxy-D-lyxo-hex-1-enopyranose 
• 26416-38-6 2-[3-(1-methoxycarbonyl-2-phenylethyl)ureido]-3-phenylpropionic acid methyl ester 

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