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Home> Encyclopedia >Pharmaceutical Intermediates>Organic Intermediate>Organic Intermediates
1H-Imidazole-4-carbaldehyde structure
1H-Imidazole-4-carbaldehyde structure

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 View more+
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:?IrritantXi,HarmfulXn
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

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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