1H-Imidazole-4-carbaldehyde
- Iupac Name：1H-imidazole-5-carbaldehyde
- CAS No.: 3034-50-2
- Molecular Weight：96.08736
- Modify Date.: 2022-11-29 10:53
- Introduction: 1H-Imidazole-4-carbaldehyde is a 4-formyl derivative of imidazole used in the preparation of C17,20-lyase inhibitor for the treatemnet of androgen-dependent prostate cancer. 4-Imidazolecarboxaldehyde is also used in the synthesis of other biologically active compounds such as antimalarial drugs. 1H-Imidazole-4-carbaldehyde Preparation Products And Raw materials Raw materials
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1. Names and Identifiers
- 1.1 Name
- 1H-Imidazole-4-carbaldehyde
- 1.2 Synonyms
1H-Imidazol-4-carboxaldehyde 1H-Imidazol-4-ylcarboxaldehyde 1H-Imidazol-5-carboxaldehyde 1H-IMIDAZOLE-4-CARBOXALDEHYDE 1H-Imidazole-5-carbaldehyde 1H-Imidazole-5-carboxaldehyde 3H-Imidazole-4-carboxaldehyde 4(5)-IMIDAZOLECARBOXALDEHYDE 4-FORMYLIMIDAZOLE 4-IMIDAZOLECARBOXALDEHYDE 5-Imidazolecarboxaldehyde FORMYLIMIDAZOLE Imidazole-4(or 5)-carboxaldehyde IMIDAZOLE-4-CARBOXALDEHYDE NSC 400521
- 1.3 CAS No.
- 3034-50-2
- 1.4 CID
- 76428
- 1.5 EINECS(EC#)
- 221-227-3
- 1.6 Molecular Formula
- C4H4N2O (isomer)
- 1.7 Inchi
- InChI=1S/C4H4N2O/c7-2-4-1-5-3-6-4/h1-3H,(H,5,6)
- 1.8 InChkey
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- C1=C(NC=N1)C=O
- 1.10 Isomers Smiles
- C1=C(NC=N1)C=O
2. Properties
- 2.1 Density
- 1.322
- 2.1 Melting point
- 173-177℃
- 2.1 Boiling point
- 163-166℃
- 2.1 Refractive index
- 1.535
- 2.1 Flash Point
- 179.8 °C
- 2.1 Precise Quality
- 96.03240
- 2.1 PSA
- 45.75000
- 2.1 logP
- 0.22220
- 2.1 Solubility
- Soluble in DMSO, methanol.
- 2.2 Appearance
- White to light yellow powder
- 2.3 Storage
- Air Sensitive. Store under Argon. Ambient temperatures.
- 2.4 Chemical Properties
- White to light yellow powder
- 2.5 pKa
- 11.05±0.10(Predicted)
- 2.6 Water Solubility
- soluble in DMSO, methanol.
- 2.7 StorageTemp
- Room temperature.
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- To a solution of 4-bromo-1H-imidazole (0.65 g, 4.4 mmol, 1.0 equiv.) indry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF (2.2 mL, 4.4 mmol, 1.0 equiv.)during 5 min. The clear solution was stirred at that temperature for an additional 5 min, and a2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was added dropwise during5 min, while maintaining the temperature below 20 C. The resulting mixture was stirred at thattemperature for 0.5 h, dry DMF (0.32 g, 4.4 mmol, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ?teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ?ltrate was concentratedand the residue was puri?ed by ash chromatography on silica gel (eluent:petroleum ether/ethylacetate = 10:1) to afford product 3l as off-white solid, 0.36 g (yield: 85percent), m.p.: 175–177 C. 1H-NMR(600 MHz, DMSO) 9.74 (s, 1H), 7.99 (s, 1H), 7.94 (s, 1H). 13C-NMR (151 MHz, DMSO) 184.46, 139.44, 134.9, 129.5.Reference Example 10Under nitrogen stream, to ( 1R, 2S, 3R) -1- (2-sulfanyl-lH- imidazol-4-yl) butane-1, 2, 3, 4-tetraol (10 g, 45.4 mmol) was added water (40 mL) , and to the obtained suspension was added dropwise an aqueous diluted solution- of 30percent aqueous hydrogen peroxide (15.4 g, 136 mmol, 3.0 equivalents) in water (40 mL) over 10 min at 17 to 43°C (the compound was gradually dissolved to give an uniform pale-yellow solution) . The reaction mixture was stirred at 24 to 36°C for 4 hr, and barium carbonate (27 g, 136 mmol, 3.0 equivalents) was added over 5 min at 24 to 26°C (neutralized to pH 7), and the mixture was stirred at 25 to26°C for 1 hr and 20 min. The insoluble material was filtered off, and washed with water (40 mL) . To the filtrate and washing was added sodium sulfite (11.4 g, 90.8 mmol, 2.0 equivalents) over 5 min at 20 to 32°C. The obtained aqueous solution was stirred at 26 to 32°C for 1 hr and 30 min to give an aqueous solution of (1R, 2S, 3R) -1- (lH-imidazol-4-yl) butane- 1 , 2 , 3 , 4-tetraol . To this aqueous solution was added sodium periodate (29.1 g, 136 mmol, 3.0 equivalents) over 10 min at 12 to 30°C, and the mixture was stirred at 27 to 30°C for 1 hr and 30 min. To the reaction mixture was added sodium periodate(2.91 g, 13.6 mmol, 0.3 equivalents) at 27 to 30°C, and the mixture was stirred at 27 to 30°C for 2 hr. The insoluble material was filtered off, and washed four times with water (10 mL) . To the filtrate and washing was added methanol (500 mL) , and the inorganic salt was filtered off, and washed twice with methanol (50 mL) . To the filtrate and washing was added activated carbon (3 g, SHIRASAGI A, trade name), and the mixture was stirred at room temperature for 1 hr. Theinsoluble material was filtered off, and washed with methanol. The filtrate and washing were concentrated under reduced pressure to give a crude compound (9.37 g) . To the crude compound were added water (3 mL) and seed crystals forcrystallization, and the mixture was stirred at roomtemperature for 24 hr, and then for 2 hr under ice-cooling. The crystals were collected by filtration-, washed with cooled water (1 mL) , and vacuum-dried (50°C) to a constant amount to give (5) -formylimidazole (2.35 g) . yield 54percent.
- 3.2 Usage
- 1H-Imidazole-4-carbaldehyde is a 4-formyl derivative of imidazole used in the preparation of C17,20-lyase inhibitor for the treatemnet of androgen-dependent prostate cancer. 4-Imidazolecarboxaldehyde is also used in the synthesis of other biologically active compounds such as antimalarial drugs. 1H-Imidazole-4-carbaldehyde Preparation Products And Raw materials Raw materials
4. Safety and Handling
- 4.1 Symbol
- GHS07;
- 4.1 Hazard Codes
- Xn
- 4.1 Signal Word
- Warning
- 4.1 Risk Statements
- R20/21/22;R36/37/38
- 4.1 Safety Statements
- S26;S36/37/39
- 4.1 Hazard Declaration
- H315; H319; H335
- 4.1 RIDADR
- NONH for all modes of transport
- 4.1 Caution Statement
- P261; P305 + P351 + P338
- 4.1 WGK Germany
- 3
- 4.1 Safety
-
Hazard Codes:?
Xi,
Xn
Risk Statements: 36/37/38-20/21/22
?R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-36-36/37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36:Wear suitable protective clothing.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
- 4.2 Sensitive
- Air Sensitive
- 4.3 Specification
-
?1H-Imidazole-5-carboxaldehyde , its cas register number is 3034-50-2. It also can be called 4-Formylimidazole ; 4-Imidazolecarboxaldehyde ; and Imidazole-4(1H)-carboxaldehyde .
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Skin irritation, Category 2
Eye irritation, Category 2
Specific target organ toxicity \u2013 single exposure, Category 3
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. |
| Response | P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. |
| Storage | P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up. |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
3034-50-2Total: 2 Synthesis Route
8. Other Information
- 8.0 Usage
- Imidazole-4-carboxaldehyde is a 4-formyl derivative of imidazole used in the preparation of C17,20-lyase inhibitor for the treatment of androgen-dependent prostate cancer. It is also used in the synthesis of other biologically active compounds such as antimalarial drugs, fabrication of colorimetric chemosensor.
- 8.1 Storage Conditions
- To a solution of 4-bromo-1H-imidazole (0.65 g, 4.4 mmol, 1.0 equiv.) indry THF (20 mL) at 0 C was added a 2 M solution of i-PrMgCl in THF (2.2 mL, 4.4 mmol, 1.0 equiv.)during 5 min. The clear solution was stirred at that temperature for an additional 5 min, and a2.5 M solution of n-BuLi in hexanes (3.5 mL, 8.8 mmol, 2.0 equiv.) was added dropwise during5 min, while maintaining the temperature below 20 C. The resulting mixture was stirred at thattemperature for 0.5 h, dry DMF (0.32 g, 4.4 mmol, 1.0 equiv.) was added to 20 C. The resultingmixture was warmed to 20 C in 0.5 h and quenched with water (6 mL). After stirring the mixturebelow 20 C for 10 min, the phases were separated and the water phase was extracted one additionaltime with ethyl acetate. The resulting suspension was allowed to reach room temperature and ?teredthrough a 0.5 1 cm pad of silica gel eluted with 10 mL of ethyl acetate. The ?ltrate was concentratedand the residue was puri?ed by ash chromatography on silica gel (eluent:petroleum ether/ethylacetate = 10:1) to afford product 3l as off-white solid, 0.36 g (yield: 85percent), m.p.: 175–177 C. 1H-NMR(600 MHz, DMSO) 9.74 (s, 1H), 7.99 (s, 1H), 7.94 (s, 1H). 13C-NMR (151 MHz, DMSO) 184.46, 139.44, 134.9, 129.5.Reference Example 10Under nitrogen stream, to ( 1R, 2S, 3R) -1- (2-sulfanyl-lH- imidazol-4-yl) butane-1, 2, 3, 4-tetraol (10 g, 45.4 mmol) was added water (40 mL) , and to the obtained suspension was added dropwise an aqueous diluted solution- of 30percent aqueous hydrogen peroxide (15.4 g, 136 mmol, 3.0 equivalents) in water (40 mL) over 10 min at 17 to 43°C (the compound was gradually dissolved to give an uniform pale-yellow solution) . The reaction mixture was stirred at 24 to 36°C for 4 hr, and barium carbonate (27 g, 136 mmol, 3.0 equivalents) was added over 5 min at 24 to 26°C (neutralized to pH 7), and the mixture was stirred at 25 to26°C for 1 hr and 20 min. The insoluble material was filtered off, and washed with water (40 mL) . To the filtrate and washing was added sodium sulfite (11.4 g, 90.8 mmol, 2.0 equivalents) over 5 min at 20 to 32°C. The obtained aqueous solution was stirred at 26 to 32°C for 1 hr and 30 min to give an aqueous solution of (1R, 2S, 3R) -1- (lH-imidazol-4-yl) butane- 1 , 2 , 3 , 4-tetraol . To this aqueous solution was added sodium periodate (29.1 g, 136 mmol, 3.0 equivalents) over 10 min at 12 to 30°C, and the mixture was stirred at 27 to 30°C for 1 hr and 30 min. To the reaction mixture was added sodium periodate(2.91 g, 13.6 mmol, 0.3 equivalents) at 27 to 30°C, and the mixture was stirred at 27 to 30°C for 2 hr. The insoluble material was filtered off, and washed four times with water (10 mL) . To the filtrate and washing was added methanol (500 mL) , and the inorganic salt was filtered off, and washed twice with methanol (50 mL) . To the filtrate and washing was added activated carbon (3 g, SHIRASAGI A, trade name), and the mixture was stirred at room temperature for 1 hr. Theinsoluble material was filtered off, and washed with methanol. The filtrate and washing were concentrated under reduced pressure to give a crude compound (9.37 g) . To the crude compound were added water (3 mL) and seed crystals forcrystallization, and the mixture was stirred at roomtemperature for 24 hr, and then for 2 hr under ice-cooling. The crystals were collected by filtration-, washed with cooled water (1 mL) , and vacuum-dried (50°C) to a constant amount to give (5) -formylimidazole (2.35 g) . yield 54percent.
- 8.2 Mesh Entry Terms
- imidazole-4-carboxaldehyde
9. Computational chemical data
- Molecular Weight: 96.08736g/mol
- Molecular Formula: C4H4N2O
- Compound Is Canonicalized: True
- XLogP3-AA: -0.1
- Exact Mass: 96.032362755
- Monoisotopic Mass: 96.032362755
- Complexity: 74.1
- Rotatable Bond Count: 1
- Hydrogen Bond Donor Count: 1
- Hydrogen Bond Acceptor Count: 2
- Topological Polar Surface Area: 45.8
- Heavy Atom Count: 7
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADcYBjIAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAABgAAAHgAQAAAACAjhlgYtkBbJkACoARx35AAAgC2XEqABUYG4cECASAhACSAUAIAIEAJAAOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
10. Question & Answer
-
4-Imidazolecarboxaldehyde (1H-Imidazole-4-carbaldehyde, 4(5)formylimidazole, 4-formylimidazole) is a 4-formyl derivative of imidazole used in the preparation of C17,20-lyase inhibitor for the treatment of androgen-dependent prostate cancer. 4-Imidazolecarboxaldehyde is also used in the synthesis of...
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