68282-49-5

Basic information

• Product Name: 2-Butyl-1H-imidazole-4-carbaldehyde
• Synonyms: 2-BUTYL-1H-IMIDAZOLE-4-CARBALDEHYDE;2-BUTYL-4-FORMYLIMIDAZOLE;2-BUTYL-4-IMIDAZOLYL FORMALDEHYDE;2-BUTYL-3H-IMIDAZOLE-4-CARBALDEHYDE;1H-IMIDAZOLE-4-CARBOXALDEHYDE, 2-BUTYL-;2-Butylimidazole-4-carboxaldehyde;2-Butyl-5-formyl imidazole;2-Butyl-4-imidazoylformaldehyde
• CAS NO: 68282-49-5
• Molecular Formula: C₈H₁₂N₂O
• Molecular Weight: 152.19
• EINECS: 1806241-263-5
• Product Categories: INTERMEDIATESOF;Imidazol&Benzimidazole
• Mol File: 68282-49-5.mol
• Article Data: 16

Chemical Properties

• Melting Point: 117-120°C
• Boiling Point: 359.1 °C at 760 mmHg
• Flash Point: 174.8 °C
• Appearance: /
• Density: 1.099 g/cm³
• Vapor Pressure: 2.44E-05mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: soluble in Methanol
• PKA: 11.58±0.10(Predicted)
• CAS DataBase Reference: 2-Butyl-1H-imidazole-4-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Butyl-1H-imidazole-4-carbaldehyde(68282-49-5)
• EPA Substance Registry System: 2-Butyl-1H-imidazole-4-carbaldehyde(68282-49-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43
• Safety Statements: 26-37/39-36/37
• Hazardous Substances Data: 68282-49-5(Hazardous Substances Data)

Usage

General Description

2-Butyl-1H-imidazole-4-carbaldehyde is a chemical compound with the molecular formula C8H12N2O. It is a derivative of imidazole and belongs to the class of organic compounds known as imidazoles. 2-Butyl-1H-imidazole-4-carbaldehyde is used in the pharmaceutical industry as an intermediate for the synthesis of various drugs and pharmaceuticals. It also has potential applications in the field of organic synthesis and as a reagent in chemical reactions. The chemical structure of 2-Butyl-1H-imidazole-4-carbaldehyde contains a butyl group attached to the imidazole ring, as well as a formyl group at the 4-position of the ring. Its properties and uses make it an important and versatile compound in the chemical and pharmaceutical industries.

InChI:InChI=1/C8H12N2O/c1-2-3-4-8-9-5-7(6-11)10-8/h5-6H,2-4H2,1H3,(H,9,10)

Synthetic route

2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
With oxygen; 2percent V/C In various solvent(s) at 105℃; under 750.075 Torr; for 6h;	100%
With manganese(IV) oxide In dichloromethane Oxidation;

bismuth (7440-69-9) + aqueous H2 O2 + sulfuric acid (7664-93-9) + pyrographite (7440-44-0) + 2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) + platinum (7440-06-4) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
With sodium hydroxide In water	100%
With sodium hydroxide In water	98.2%
With sodium hydroxide In methanol; water	94.5%

bismuth (7440-69-9) + pyrographite (7440-44-0) + 2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) + 4-methyl-2-pentanone (108-10-1) + platinum (7440-06-4) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
With sodium hydroxide In dodecane; water	90%

bismuth (7440-69-9) + aqueous H2 O2 + pyrographite (7440-44-0) + 2-butyl-5-hydroxymethyl-1H-imidazole (68283-19-2) + 4-methyl-2-pentanone (108-10-1) + platinum (7440-06-4) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
With sodium hydroxide In dodecane; water	88.2%

2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
Stage #1: 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde With hydrogen; triethylamine; palladium 10% on activated carbon In methanol at 20 - 25℃; under 2942.29 - 3677.86 Torr; for 8 - 10h; Stage #2: With hydrogenchloride In water at 25 - 30℃; pH=1.2; Stage #3: With sodium carbonate In water pH=6.8 - 7.5; Product distribution / selectivity;	74%

2-n-butyl-4-(hydroxymethyl)imidazole (68283-19-2) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
With sodium hydroxide; bismuth(III) sulfate; dihydrogen peroxide; platinum on carbon In water at 20 - 62℃; for 3.5 - 4.5h; Product distribution / selectivity;	61%

2-butyl-1H-imidazole (50790-93-7) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2O 2: MnO2 / CH2Cl2 View Scheme
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 °C 1.2: 2 h / 0 - 25 °C 2.1: n-butyllithium / tetrahydrofuran / -78 °C / Inert atmosphere 2.2: -78 - -50 °C / Inert atmosphere 2.3: 2 h / 0 - 25 °C View Scheme

pentanonitrile (110-59-8) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 72 percent / hydrogen chloride / 18 h / 0 - 15 °C 2: 75 percent / NH3 / 60 °C / high pressure 3: MnO2 / CH2Cl2 View Scheme

2-butyl-3-dimethylaminomethylimidazole → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
With hydrogenchloride; n-butyllithium In tetrahydrofuran; hexane; N,N-dimethyl-formamide

2-butyl-3-dimethylaminosulfonylimidazole (148454-64-2) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
Stage #1: 2-butyl-3-dimethylaminosulfonylimidazole With n-butyllithium In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -78 - -50℃; Inert atmosphere; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0 - 25℃; for 2h;

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde (133040-03-6) + methyl 4-[(2-butyl-4-formyl-1H-imidazol-1-yl)methyl]benzoate (159708-89-1)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Substitution;	A 27% B 54%
Stage #1: 2-butyl-1H-imidazole-5-carboxaldehyde With tetraethylammonium hydroxide In N,N-dimethyl-formamide for 1h; deprotonation; Stage #2: Methyl 4-(bromomethyl)benzoate In water; N,N-dimethyl-formamide at 0 - 20℃; for 3h; Alkylation;	A 40% B 54%
With sodium carbonate In N,N-dimethyl-formamide at 70℃; Alkylation;
With potassium carbonate In N,N-dimethyl-formamide at 20℃;

Methyl 4'-(bromomethyl)biphenyl-2-carboxylate (114772-38-2) + 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-butyl-1-<(2'-carbomethoxy<1,1'-biphenyl>-4-yl)methyl>-1H-imidazole-5-carboxaldehyde (152147-96-1) + 4'-(2-butyl-4-formyl-imidazol-1-ylmethyl)-biphenyl-2-carboxylic acid methyl ester (470691-30-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 25℃;	A 23% B 48%

(1R,2R,3R,5S)-(-)-Isopinocampheylamine (69460-11-3) + 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → (1R,2R,3R,5S)-N-((2-butyl-1H-imidazol-5-yl)methyl)-2,6,6-trimethylbicyclo[3.1.1]heptan-3-amine hydrochloride

Conditions	Yield
Stage #1: (1R,2R,3R,5S)-(-)-Isopinocampheylamine; 2-butyl-1H-imidazole-5-carboxaldehyde With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 20℃; for 1.5h; Inert atmosphere; Stage #2: With hydrogenchloride In ethyl acetate	44%

pyrrole (109-97-7) + 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → meso-tetrakis(2-n-butylimidazol-5-yl)porphyrin

Conditions	Yield
In propionic acid for 1h; Heating;	26%

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde (83857-96-9)

Conditions	Yield
With N-chloro-succinimide Chlorination;

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 4-[2-butyl-5-(2-ethoxycarbonyl-2-phenylsulfanyl-vinyl)-imidazol-1-ylmethyl]-benzoic acid ethyl ester (220579-46-4)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Na2CO3 / dimethylformamide / 70 °C 2.2: ethanol View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 4-[2-butyl-4-(2-ethoxycarbonyl-2-phenylsulfanyl-vinyl)-imidazol-1-ylmethyl]-benzoic acid ethyl ester (220579-42-0)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: Na2CO3 / dimethylformamide / 70 °C 2.2: ethanol View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → C24H22N2O4S(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Na2CO3 / dimethylformamide / 70 °C 2.2: ethanol 3.1: NaOH / ethanol; H2O / Alkaline hydrolysis View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → C24H22N2O4S(2-)*2Na(1+)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: Na2CO3 / dimethylformamide / 70 °C 2.2: ethanol 3.1: NaOH / ethanol; H2O / Alkaline hydrolysis View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 4'-[5-((Z)-2-Azido-2-methoxycarbonyl-vinyl)-2-butyl-imidazol-1-ylmethyl]-biphenyl-2-carboxylic acid methyl ester (470691-32-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 23 percent / potassium carbonate / dimethylformamide / 25 °C 2: 42 percent / sodium; methanol / -15 °C View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 4'-[4-((E)-2-Azido-2-methoxycarbonyl-vinyl)-2-butyl-imidazol-1-ylmethyl]-biphenyl-2-carboxylic acid methyl ester (470691-34-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 48 percent / potassium carbonate / dimethylformamide / 25 °C 2: 40 percent / sodium; methanol / -15 °C View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → methyl 2-(n-butyl)-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]pyrrolo[2,3-d]imidazole-5-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: 23 percent / potassium carbonate / dimethylformamide / 25 °C 2: 42 percent / sodium; methanol / -15 °C 3: 32 percent / xylene / Heating View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → methyl 2-(n-butyl)-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]pyrrolo[3,2-d]imidazole-5-carboxylate (470691-39-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 48 percent / potassium carbonate / dimethylformamide / 25 °C 2: 40 percent / sodium; methanol / -15 °C 3: 35 percent / xylene / Heating View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → α-azido-β-[2-butyl-1-(4-carbethoxybenzyl)imidazol-5-yl]acrylate

Conditions	Yield
Multi-step reaction with 2 steps 1: 27 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C 2: 66 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → ethyl 2-butyl-1-(4-carbethoxybenzyl)pyrrolo[3,2-d]imidazole-5-carboxylate

Conditions	Yield
Multi-step reaction with 3 steps 1: 54 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C 2: 40 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C 3: 28 percent / xylene / 2 h / Heating View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 27 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C 2: 66 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C 3: 22 percent / xylene / 2 h / Heating View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → α-azido-β-[2-butyl-1-(4-carbethoxybenzyl)imidazol-4-yl]acrylate (203204-02-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / sodium carbonate / dimethylformamide / 24 h / 100 °C 2: 40 percent / NaOEt / tetrahydrofuran / 2 h / -10 °C View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde (133040-03-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: N-chlorosuccinimide 2: K2CO3 / dimethylformamide 3: H2 / Pd/C View Scheme

2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-butyl-4-chloro-1-<(4-carbomethoxyphenyl)methyl>-1H-imidazole-5-carboxaldehyde (133040-02-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: N-chlorosuccinimide 2: K2CO3 / dimethylformamide View Scheme

Chloromethyl pivalate (18997-19-8) + methyl (E)-3-<2-butyl-1-<(2-chlorophenyl)methyl>imidazol-5-yl>-2-<(2-thienyl)methyl>-2-propenoate (133485-47-9) + 2-butyl-1H-imidazole-5-carboxaldehyde (68282-49-5) → 2-n-butyl-1-pivalyloxymethylimidazol-5-carboxaldehyde (133486-33-6)

Conditions	Yield
With manganese dioxide; potassium carbonate In N-methyl-acetamide

Upstream product

• 68283-19-2 2-butyl-5-hydroxymethyl-1H-imidazole 
• 7440-69-9 bismuth 
• 7664-93-9 sulfuric acid 
• 7440-44-0 pyrographite 
• 7440-06-4 platinum 
• 108-10-1 4-methyl-2-pentanone 
• 68283-19-2 2-n-butyl-4-(hydroxymethyl)imidazole 
• 83857-96-9 2-n-butyl-4-chloro-1H-imidazol-5-carboxaldehyde 
• 148454-64-2 2-butyl-3-dimethylaminosulfonylimidazole 
• 68-12-2 N,N-dimethyl-formamide 
• 110-59-8 pentanonitrile 
• 50790-93-7 2-butyl-1H-imidazole 

Downstream Products

• 133040-03-6 2-n-butyl-1-[(4-carbomethoxyphenyl)methyl]-1H-imidazol-5-carboxaldehyde 
• 159708-89-1 methyl 4-[(2-butyl-4-formyl-1H-imidazol-1-yl)methyl]benzoate 
• 905456-95-3 2-butyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazole-5-carbaldehyde 
• 1246667-40-2 eprosartan mesylate 
• 148674-41-3 4-({2-butyl-5-[2-carboxy-2-(thiophen-2-ylmethyl)eth-1-en-1-yl]-1H-imidazol-1-yl}methyl)benzoic acid 
• 152147-96-1 2-butyl-1-<(2'-carbomethoxy<1,1'-biphenyl>-4-yl)methyl>-1H-imidazole-5-carboxaldehyde 
• 470691-30-6 4'-(2-butyl-4-formyl-imidazol-1-ylmethyl)-biphenyl-2-carboxylic acid methyl ester 
• 1206696-90-3 2-butyl-1-[2'-(1-trityl-1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazole-4-carbaldehyde 

Relevant articles and documents

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