58954-23-7

Basic information

• Product Name: 2-Propyl-1H-imidazole-4,5-dicarboxy acid
• Synonyms: 2-propyl-1H-imidazole-4,5-dicarboxylic acid;1H-imidazole-4,5-dicarboxy acid,2-propyl;1H-Imidazole-4,5-dicarboxylic acid, 2-propyl-;2-Propyl Imidazole Dicarboxylic Acid;2-propylimidazloe-4,5-dicarboxylic acid;2-PROLPYL-1H-LMIDAZOLE-4,5-DICARBOXYLICALID;2-PROLPYL-1H-IMIDAZOLE-4,5-DICARBOXYLICALID,98%;2-Propyl-1H-imidazole-4,5-dicarboxy acid
• CAS NO: 58954-23-7
• Molecular Formula: C₈H₁₀N₂O₄
• Molecular Weight: 198.176
• EINECS: 1312995-182-4
• Product Categories: Organic acids;API intermediates
• Mol File: 58954-23-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 262-264 °C(Solv: ethanol (64-17-5))
• Boiling Point: 552.885 °C at 760 mmHg
• Flash Point: 288.174 °C
• Appearance: /
• Density: 1.464 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.608
• Storage Temp.: 2-8°C
• PKA: 0.65±0.10(Predicted)
• CAS DataBase Reference: 2-Propyl-1H-imidazole-4,5-dicarboxy acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propyl-1H-imidazole-4,5-dicarboxy acid(58954-23-7)
• EPA Substance Registry System: 2-Propyl-1H-imidazole-4,5-dicarboxy acid(58954-23-7)

Safety Data

• Hazardous Substances Data: 58954-23-7(Hazardous Substances Data)

Usage

Uses

2-Propylimidazole-4,5-dicarboxylic acid is a useful research chemical compound.

Chemical Properties

White flake crystal

InChI:InChI=1/C8H10N2O4/c1-2-3-4-9-5(7(11)12)6(10-4)8(13)14/h2-3H2,1H3,(H,9,10)(H,11,12)(H,13,14)

Synthetic route

2-propylimidazole-4,5-dicarbonitrile (51802-42-7) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With hydrogenchloride In water at 100℃; for 0.0333333h; Temperature;	96.5%
With hydrogenchloride; water for 4h; Reflux; Large scale reaction;	95%
With hydrogenchloride for 8h; Heating;	80%

2-propyl-1H-benzimidazole (5465-29-2) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With sodium tungstate; disodium hydrogenphosphate; potassium dihydrogenphosphate; dihydrogen peroxide In water at 100℃; for 1h; pH=4.9; Concentration; pH-value; Temperature;	85.5%
With sulfuric acid; dihydrogen peroxide In water at 100 - 120℃; for 0.5h; Concentration;	72%
With sulfuric acid; dihydrogen peroxide In water for 3h; Reflux;	35%

2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With sodium hydroxide In tetrahydrofuran at 50℃; for 4h;	85%

L-Tartaric acid (87-69-4) + butyraldehyde (123-72-8) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
Stage #1: L-Tartaric acid With sulfuric acid; nitric acid at 43 - 46℃; for 1.61667h; Stage #2: butyraldehyde With ammonium hydroxide In 1-methyl-pyrrolidin-2-one at -10 - 4℃; Solvent; Temperature;	46%

2-propyl-1H-benzimidazole (5465-29-2) → 4,5-imidazoledicarboxylic acid (570-22-9) + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In water at 100 - 130℃;	A 31% B 1%

butyraldehyde (123-72-8) + dinitrate of/the/ (+)-tartaric acid → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With ammonia

di-O-nitro-tartaric acid (610-20-8) + butyraldehyde (123-72-8) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
With ammonium hydroxide at 0℃; for 0.5h;	97 g

1,1,1-trimethoxybutane (43083-12-1) + diaminomaleonitrile (1187-42-4) → 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7)

Conditions	Yield
In methanol Reflux;

methanol (67-56-1) + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → 2-propyl-4,5-bis(methoxycarbonyl)-imidazole (124750-59-0)

Conditions	Yield
With thionyl chloride at 40 - 45℃; Large scale reaction;	96%
With thionyl chloride at 43℃; for 11h;
Stage #1: methanol; 2-propyl-1H-imidazole-4,5-dicarboxylic acid With thionyl chloride Reflux; Stage #2: With sodium hydroxide In water for 0.25h;

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + ethanol (64-17-5) → 2-propyl-1H-imidazole-4, 5-diethyl azodicarboxylate (144689-94-1)

Conditions	Yield
Stage #1: 2-propyl-1H-imidazole-4,5-dicarboxylic acid; ethanol With hydrogenchloride; thionyl chloride at 5℃; for 0.166667h; Stage #2: for 1.5h; Heating;	94%
With hydrogenchloride Ambient temperature;	86%
With thionyl chloride In water at 8℃; for 6.6h; Temperature; Reflux;	77%
at 0℃; for 12h; Reflux;

cobalt(II) nitrate hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) + dimethyl sulfoxide (67-68-5) → C16H22CoN4O10*2C2H6OS

Conditions	Yield
In methanol at 80℃; for 72h;	88.49%

cobalt(II) chloride hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → [Co3(pimda)2(H2O)5]

Conditions	Yield
With triethylamine In water at 170℃; for 96h; Autoclave;	84%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) + zinc(II) chloride (7646-85-7) → diaquabis(2-propyl-4,5-imidazoledicarboxylato)zinc(II) tetrahydrate

Conditions	Yield
In ethanol; water ligand dissolved in H2O at room temp., mixed with EtOH soln. of ZnCl2, heated at 70°C for 8 h; crystd. at room temp. for 5 d, washed (H2O), elem. anal.;	81.3%
In ethanol; water imidazole-compd. dissolved in H2O, Zn-compd. dissolved in EtOH, two solution mixed, heated to 70°C for 8 h; filtered, evaporated at room temp. for 5 d, washed with H2O, elem. anal.;	81.3%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + zinc(II) acetate dihydrate (5970-45-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → diaquabis(2-propyl-4,5-imidazoledicarboxylato)zinc(II) - N,N-dimethylformamide (1/2)

Conditions	Yield
In water; N,N-dimethyl-formamide ligand dissolved in H2O at room temp., mixed with DMF soln. of Zn(CH3COO)2*2H2O, refluxed for 8 h; crystd. at room temp. for 15 d, washed (H2O), elem. anal.;	78%
In water; N,N-dimethyl-formamide imidazole-compd. dissolved in H2O at room temp., Zn-compd. dissolved in DMF, two solution mixed, refluxed for 8 h; filtered, evaporated at room temp. for 15 d, washed with H2O, elem. anal.;	78%

cadmium(II) nitrate tetrhydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → Cd(2-propyl-1H-imidazole-4,5-dicarboxylic acid(-1H))2(H2O)2*4H2O

Conditions	Yield
With 3,3',4,4'-biphenyltetracarboxylic acid In water mixt. of acid and Cd(NO3)2*4H2O dissolved in H2O; stirred for 0.5 h; heated at 75°C for 3 d; elem. anal.;	77%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + copper(II) acetate monohydrate (6046-93-1) → [Cu(2-propylimidazole-4-carboxylato-5-carboxylic acid)2]n

Conditions	Yield
In water at 20 - 130℃; Sealed tube;	75%

cadmium(II) nitrate tetrhydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → [Cd2(2-propyl-1H-imidazole-4,5-dicarboxylic acid(-2H))2(DMF)2

Conditions	Yield
With benzidine; terephthalic acid In water; N,N-dimethyl-formamide mixt. of imidazole deriv., Cd nitrate, benzidine, terephthalic adcid heated in mixt. DMF/H2O heated at 75°C for 48 h; washed by water, dried in air; elem. anal.;	74%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + zinc diacetate (557-34-6) + water (7732-18-5) → Zn(2-propyl-1H-imidazole-4,5-dicarboxylic acid(-1H))2(H2O)2*3.5H2O

Conditions	Yield
With 3,3',4,4'-biphenyltetracarboxylic acid In water mixt. of acid and Zn(OAc)2 dissolved in H2O; stirred for 0.5 h; heated at 75°C for 3 d; elem. anal.;	72%

4,4'-bipyridine (553-26-4) + manganese (II) sulfate monohydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → [Mn3(2-propyl-4,5-imidazoledicarboxylate(2-))2(2-propyl-4,5-imidazoledicarboxylate(1-))2(4,4'-bipyridine)2(H2O)2]n

Conditions	Yield
With sodium hydroxide In ethanol; water; acetonitrile at 130℃; for 48h; pH=6.5; Sealed tube; High pressure;	71%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + cadmium(II) acetate dihydrate (5743-04-4) → [Cd(2-propyl-4,5-imidazoledicarboxylic acid(-1H))2]n

Conditions	Yield
Stage #1: 2-propyl-1H-imidazole-4,5-dicarboxylic acid With sodium hydroxide In water at 20℃; pH=6; Stage #2: cadmium(II) acetate dihydrate In ethanol; water at 75℃; for 8h;	70.8%
Stage #1: 2-propyl-1H-imidazole-4,5-dicarboxylic acid; cadmium(II) acetate dihydrate In water for 0.333333h; Stage #2: In water at 180℃; for 120h; Sealed tube;	35.2%

copper(II) choride dihydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → [Cu(2-propyl-4,5-imidazoledicarboxylic acid(-1H))2] (1233863-63-2)

Conditions	Yield
Stage #1: 2-propyl-1H-imidazole-4,5-dicarboxylic acid With sodium hydroxide In water at 20℃; pH=6.5; Stage #2: copper(II) choride dihydrate In ethanol; water at 70℃; for 8h;	70.8%

lead(II) acetate trihydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → [Pb(2-propyl-4,5-imidazoledicarboxylic acid(-1H))2(water)2]n

Conditions	Yield
Stage #1: 2-propyl-1H-imidazole-4,5-dicarboxylic acid With sodium hydroxide In water at 20℃; pH=6; Stage #2: lead(II) acetate trihydrate In ethanol; water at 75℃; for 8h;	70.8%

1,10-Phenanthroline (66-71-7) + cobalt(II) nitrate hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → [Co(2-propyl-1H-imidazole-4,5-dicarboxylic acid(-3H))(1,10-phenanthroline)]*H2O (1389320-06-2)

Conditions	Yield
In water High Pressure; Co compd., ligand, and phen (1:1:1 molar ratio) in H2O, sealed, heated at 170°C for 3 d; cooled, crystd., septd., washed (H2O);	70%

lead(II) perchlorate trihydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → Pb(2-propyl-4,5-imidazole dicarboxylate(-1H))2

Conditions	Yield
In water High Pressure; mixt. of Pb(ClO4)2*3H2O, acid and water stirred 1 h, sealed in Teflon reactor, heated at 160°C for 5 d; cooled to room temp. at 3°C/h; elem. anal.;	69.8%

1,10-Phenanthroline (66-71-7) + cobalt(II) chloride hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → 2C8H9N2O4(1-)*Co(2+)*H2O*C12H8N2

Conditions	Yield
With hydrogenchloride In acetonitrile at 110℃; for 99h; pH=4; Autoclave; High pressure;	69%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) + cobalt(II) diacetate tetrahydrate (6147-53-1) → [Co(2-propylimidazole-4,5-dicarboxylic acid(-H))2(H2O)2]*3H2O

Conditions	Yield
With sodium hydroxide at 80℃; for 2h; pH=3.6;	68%
In water High Pressure; stoich. mixt. in H2O, sealed, heated at 130°C for 144 h; cooled to room temp. in 20 h, crystd., septd., washed (H2O), dried in air, elem. anal.;	56%

cobalt(II) nitrate hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → diaquabis(2-propyl-1H-imidazole-4,5-dicarboxylate)cobalt(II) (1263036-89-0, 1263416-17-6)

Conditions	Yield
In water; acetonitrile High Pressure; mixt. of Co(NO3)2*6H2O and imidazole dicarboxylic acid (1:1) in H2O/CH3CN heated in an autoclave at 152°C for 72 h; cooled to room temp. (10°C/h), collected, washed (h2O), dried (air), elem. anal.;	68%

1,1'-(1,4-butanediyl)bis(imidazole) (69506-86-1) + cadmium(II) perchlorate hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → [Cd2(2-propyl-4,5-imidazoledicarboxylic acid(-1H))2(1,1'-(1,4-butanediyl)bis(imidazole))0.5(H2O)2]

Conditions	Yield
In water High Pressure; Zn compd., ligand, and bbi (2:2:1 molar ratio) in H2O, sealed, heated at140°C for 3 h; cooled (5°C), elem. anal.;	67%

2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) + cobalt(II) diacetate tetrahydrate (6147-53-1) + 1,2-diaminopropan (78-90-0, 10424-38-1) → 4C3H10N2*4Co(3+)*9H2O*4C8H7N2O4(3-)

Conditions	Yield
at 120℃; for 24h; Autoclave;	67%

cadmium(II) perchlorate + 1,3-di(4-pyridyl)propane (17252-51-6) + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → 2Cd(2+)*2(C3H7)C3HN2(COO)2(2-)*C5H4N(CH2)3C5H4N*H2O=[Cd2((C3H7)C3HN2(COO)2)2(C5H4N(CH2)3C5H4N)(H2O)]

Conditions	Yield
In water High Pressure; Cd compd.:H2pimdc:bpp (1:1:5 molar ratio) in water, sealed, heated at 140°C for 3 d; crystd. on cooling to room temp., elem. anal.;	66%

1,10-Phenanthroline (66-71-7) + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + copper(II) ion → [Cu(3-propyl-4,5-dicarboxy-1H-imidazole(1-))2(1,10-phenanthroline)]

Conditions	Yield
In water High Pressure; hydrothermal synthesis; 3-propyl-4,5-dicarboxy-1H-imidazole, 1,10-phenanthroline, Cu salt, H2O stirred for 10 min; heated in a sealed Teflon-lined stainless steel autoclave at 170°C for 72 h; cooled to room temp. with 5°C/h; washed with H2O; dried in air; elem. anal.;	66%

manganese (II) sulfate monohydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → diaquabis(2-propyl-1H-imidazole-4,5-dicarboxylate)manganese(II) (1256502-07-4, 1374450-98-2)

Conditions	Yield
In water; acetonitrile High Pressure; mixt. of MnSO4*H2O and imidazole dicarboxylic acid (1:1) in H2O/CH3CN heated in an autoclave at 152°C for 72 h; cooled to room temp. (10°C/h), collected, washed (h2O), dried (air), elem. anal.;	65%

cobalt(II) chloride hexahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + 1,4-phenylenediacetic acid (7325-46-4) → 3Co(2+)*6C8H7N2O4(3-)*C10H10O4*6H2O*12H(1+)

Conditions	Yield
In ethanol; water at 130℃; for 78h; pH=6; Autoclave;	65%

1,10-Phenanthroline (66-71-7) + iron(II) chloride tetrahydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) + water (7732-18-5) → 2C8H9N2O4(1-)*Fe(2+)*H2O*C12H8N2

Conditions	Yield
With hydrogenchloride In acetonitrile at 100℃; for 99h; pH=2; Autoclave; High pressure;	65%

[2,2]bipyridinyl (366-18-7) + manganese (II) sulfate monohydrate + 2-propyl-1H-imidazole-4,5-dicarboxylic acid (58954-23-7) → [Mn(2-propyl-4,5-imidazoledicarboxylate(1-))2(2,2'-bipyridine)]

Conditions	Yield
With sodium hydroxide In ethanol; water; acetonitrile at 130℃; for 48h; pH=6; Sealed tube; High pressure;	63%

Upstream product

• 51802-42-7 2-propylimidazole-4,5-dicarbonitrile 
• 5465-29-2 2-propyl-1H-benzimidazole 
• 144689-94-1 diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate 
• 87-69-4 L-Tartaric acid 
• 123-72-8 butyraldehyde 
• 43083-12-1 1,1,1-trimethoxybutane 
• 1187-42-4 diaminomaleonitrile 
• 610-20-8 di-O-nitro-tartaric acid 

Downstream Products

• 144689-94-1 diethyl 2-(n-propyl)-1H-imidazole-4,5-dicarboxylate 
• 172875-52-4 2-propylimidazole-4-carboxylic acid 
• 124750-59-0 2-propyl-4,5-bis(methoxycarbonyl)-imidazole 
• 752179-89-8 1-((2'-(2-triphenylmethyl-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylic acid 
• 144689-63-4 olmesartan 
• 1020157-01-0 (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2′-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate 
• 1027174-22-6 5-(1-Hydroxy-1-methyl-ethyl)-2-propyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid 2,2-dimethyl-propionyloxymethyl ester 
• 172876-04-9 5-Hydroxymethyl-2-propyl-1-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-1H-imidazole-4-carboxylic acid ethyl ester 
• 172875-70-6 5-Isopropenyl-2-propyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester 
• 172875-59-1 ethyl 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[2'-(2-triphenylmethyl-2H-tetrazol-5-yl)biphenyl-4-yl]methyl-1H-imidazole-5-carboxylate 
• 172876-01-6 5-Hydroxymethyl-2-propyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester 
• 172875-61-5 5-Isopropyl-2-propyl-3-[2'-(2-trityl-2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid ethyl ester 
• 144689-63-4 olmesartan medoxomil 
• 1026321-00-5 3-[2'-(2,2-Dimethyl-propionyloxymethoxycarbonyl)-biphenyl-4-ylmethyl]-5-(1-hydroxy-1-methyl-ethyl)-2-propyl-3H-imidazole-4-carboxylic acid benzyl ester 

Relevant articles and documents

Preparation method of diacid

The invention relates to a preparation method of diacid, and belongs to the field of medicinal chemistry. The preparation method provided by the invention comprises: carrying out carboxylation reaction on raw materials under the action of acid under a continuous flow reaction condition. The method provided by the invention has the advantages of cheap and easily available raw materials, simple process, low cost, high product purity and yield, green and environment-friendly process, and facilitation of industrialization.

Influence of Oxidation Conditions on the Yield of 2-Substituted Imidazole-4,5-dicarboxylic Acids

Conditions were found which allow 2-alkyl-substituted imidazole-4,5-dicarboxylic acids to be synthesized in preparative quantities by the oxidation of 2-alkylbenzimidazoles with hydrogen peroxide. It was shown that optimal results can be obtained at the concentration of 2-alkylimidazole in sulfuric acid of 1 M and the hydrogen peroxide: 2-alkylbenzimidazole molar ratio of 11: 1. Oxidation under these conditions results in higher yields of the target 2-alkylimidazole-4,5-dicarboxylic acids, including those with a branched alkyl group.

Unexpected formation of imidazole-4,5-dicarboxylic acid in the oxidation of 2-substituted benzimidazoles with hydrogen peroxide

-