Imidazole-4-acetic acid supplier

Name
Imidazole-4-acetic acid
EINECS
CAS No. 645-65-8
Article Data12
CAS DataBase
Density 1.426 g/cm³
Solubility
Melting Point 217-219 °C (decomp)
Formula C₅H₆N₂O₂
Boiling Point 447.343 °C at 760 mmHg
Molecular Weight 126.115
Flash Point 224.345 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1H-Imidazole-4-aceticacid (9CI);Imidazole-4(or 5)-acetic acid (6CI);Imidazole-4-acetic acid (8CI);(1H-Imidazol-4-yl)acetic acid;(3H-Imidazol-4-yl)acetic acid;(Imidazol-4-yl)acetic acid;2-(1H-Imidazol-5-yl)acetic acid;4-(Carboxymethyl)-1H-imidazole;I-4-AA;Imidazol-4(5)-ylacetic acid;Imidazoleacetic acid;NSC 60104;Imidazole-4-acetic acid;
PSA 65.98000
LogP 0.03680

Synthetic route

: 18502-05-1
4-cyanomethylimidazole

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

Conditions

Conditions	Yield
With ethanol; sodium
With sodium hydroxide; water
With hydrogenchloride; water

α-oxy-β--propionic acid: α-oxy-β--propionic acid

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

Conditions

Conditions	Yield
With barium permanganate; sulfuric acid

: 872-82-2
2-(1H-imidazol-4-yl)ethanol

: 7732-18-5
water

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

Conditions

Conditions	Yield
UV-Licht.Irradiation;

: 3465-72-3
urocanic Acid

A: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

B: 3034-50-2
4(5)formylimidazole

C: 1072-84-0
imidazole-4-carboxylic acid

D: 7699-35-6
(Z)-urocanic acid

Conditions

Conditions	Yield
With dihydrogen peroxide pH=7.2; Product distribution / selectivity; aqueous phosphate buffer; UV-irradiation;

...Expand

: 3465-72-3
urocanic Acid

A: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

B: 3034-50-2
4(5)formylimidazole

C: 1072-84-0
imidazole-4-carboxylic acid

Conditions

Conditions	Yield
With dihydrogen peroxide pH=7.2; Product distribution / selectivity; Fenton Oxidation; aqueous phosphate buffer;
With dihydrogen peroxide In water pH=7.2; Product distribution / selectivity; Fenton Oxidation;

...Expand

: 67-56-1
methanol

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 4200-46-8
(1H-imidazol-4-yl)-acetic acid methyl ester

Conditions

Conditions	Yield
With thionyl chloride for 4h; Reflux;	99%
With hydrogenchloride Heating;
With hydrogenchloride
With thionyl chloride at 70℃;

: 67-56-1
methanol

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 51718-80-0
methyl 2-(1H-imidazol-4-yl)acetate hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane at 60℃;	98%
With thionyl chloride for 4h; Heating / reflux;

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 142643-14-9
(1S,2S)-2,3-dihydro-1'-(((2-amino-7,7-dimethylbicyclo<2.2.1>hept-1-yl)methyl)sulfonyl)spiro(1H-indene-1,4'-piperidine)

: (1S,2S)-2,3-dihydro-1'-(((7,7-dimethyl-2-((4-imidazolylacetyl)amino)bicyclo<2.2.1>hept-1-yl)methyl)sulfonyl)spiro(1H-indene-1,4'-piperidine)

Conditions

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1-hydroxybenzotriazol-hydrate; triethylamine In N,N-dimethyl-formamide at 25℃; for 18h;	92%

: 64-17-5
ethanol

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 28782-45-8
(1H-imidazol-4-yl)-acetic acid ethyl ester

Conditions

Conditions	Yield
With sulfuric acid	90%
With acetyl chloride for 5h;

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 70-34-8
2,4-Dinitrofluorobenzene

: 153527-31-2
[1-(2,4-dinitrophenyl)-1H-imidazol-4-yl]acetic acid

Conditions

Conditions	Yield
With sodium hydrogencarbonate In N,N-dimethyl-formamide	72%

: C20H30N2O2

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: N-(cyclopentylmethyl)-2-(1H-imidazol-4-yl)-N-{1-(4-methylphenyl)-2-oxo-2-[(tetrahydrofuran-2-ylmethyl)amino]ethyl}acetamide

Conditions

Conditions	Yield
Stage #1: 2-(1H-imidazol-4-yl)acetic acid With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In dichloromethane at 20℃; for 1h; Stage #2: C20H30N2O2 With triethylamine In dichloromethane at 20℃;	70%

: 1428264-81-6
(S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 4-methylbenzenesulfonate

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 1448440-90-1
(S)-N-(2-(2-cyanopyrrolidin-1-yl)-2-oxoethyl)-2-(1H-imidazol-4-yl)acetamide

Conditions

Conditions	Yield
Stage #1: 2-(1H-imidazol-4-yl)acetic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.25h; Stage #2: (S)-1-(2-aminoacetyl)pyrrolidine-2-carbonitrile 4-methylbenzenesulfonate In N,N-dimethyl-formamide at 20℃;	66%

: 373-44-4
1,8-diaminooctan

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: N-(8-(2-(1H-imidazol-4-yl)acetamido)octyl)-2-(1H-imidazol-5-yl)acetamide

Conditions

Conditions	Yield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 12h;	65%

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 85068-29-7
3,5-bis-trifluoromethylbenzylamine

: C14H11F6N3O

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide	62%

: 4-cyano-1H-imidazole-2-carboxylic acid (2-cyclohex-1-enyl-4-piperidin-4-yl-phenyl)-amide trifluoroacetic acid salt

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 4-cyano-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(2-1H-imidazol-4-yl-acetyl)piperidin-4-yl]phenyl}amide trifluoroacetic acid salt

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 10h;	60%

: 24424-99-5
di-tert-butyl dicarbonate

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 112856-43-6
4-carboxymethyl-imidazole-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap; triethylamine In tetrahydrofuran; water at 0 - 20℃;	54%

: C35H38N4O3

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: C54H50N6O8

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 6h;	38%

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 28226-22-4
6-nitro-1,4-benzoxazine

: 928118-22-3
C13H12N4O4

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20 - 25℃;	38%

: 702692-02-2
C43H44N4O5

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: C48H48N6O6

Conditions

Conditions	Yield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran for 6h;	38%

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 4-(2-((5-chloro-2-propoxybenzyl)amino)ethyl)-N-(prop-2-yn-1-yl)benzenesulfon-amide

: N-(5-chloro-2-propoxybenzyl)-2-(1H-imidazol-4-yl)-N-(4-(N-(prop-2-yn-1-yl)sulfamo-yl)phenethyl)acetamide

Conditions

Conditions	Yield
Stage #1: 2-(1H-imidazol-4-yl)acetic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Inert atmosphere; Stage #2: 4-(2-((5-chloro-2-propoxybenzyl)amino)ethyl)-N-(prop-2-yn-1-yl)benzenesulfon-amide With triethylamine In dichloromethane at 20℃; for 3h; Inert atmosphere;	35%

: 1313006-17-5
3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}imidazo[1,2-a]pyridine-6-carbonitrile

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 1313007-40-7
3-(4-{[(3R)-1-(1H-imidazol-4-ylacetyl)piperidin-3-yl]amino}pyrimidin-2-yl)imidazo[1,2-a]pyridine-6-carbonitrile

Conditions

Conditions	Yield
Stage #1: 2-(1H-imidazol-4-yl)acetic acid With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}imidazo[1,2-a]pyridine-6-carbonitrile In N,N-dimethyl-formamide	32%
Stage #1: 2-(1H-imidazol-4-yl)acetic acid With triethylamine; 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: 3-{4-[(3R)-piperidin-3-ylamino]pyrimidin-2-yl}imidazo[1,2-a]pyridine-6-carbonitrile	32%

: 1322757-73-2
ethyl 5-amino-3-(4-chlorophenyl)-4-cyanothiophene-2-carboxylate

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: ethyl 5-(2-(1H-imidazol-4-yl)acetamido)-3-(4-chlorophenyl)-4-cyanothiophene-2-carboxylate

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 120h; Inert atmosphere;	30%

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: (2S,3S)-3-methyl-2-methylaminopentanoic acid benzyl ester

: (2S,3S)-2-[(2-1H-imidazol-4-ylacetyl)methylamino]-3-methylpentanoic acid benzyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	27.4%

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 77-78-1
dimethyl sulfate

: 584-91-8
zwitterionic zooanemonin

: 34529-06-1
dimethyl 3-aminophthalate

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 141344-44-7
dimethyl 3-<<2-(4-carboxymethyl)imidazolyl>azo>phthalate

Conditions

Conditions	Yield
With hydrogenchloride; sodium carbonate; sodium nitrite 2.) 4 deg C, 30 min; Multistep reaction;

: 103259-06-9
2-(methoxycarbonyl)-6-aminobenzoic acid

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 141344-48-1
methyl 2-carboxy-3-<<2-(4-carboxymethyl)imidazolyl>azo>benzoate

Conditions

Conditions	Yield
With hydrogenchloride; sodium carbonate; sodium nitrite 2.) 4 deg C, 30 min; Multistep reaction;

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 113579-20-7
3-amino-2-(methoxycarbonyl)benzoic acid

: 141344-43-6
methyl 2-carboxy-6-<<2-(4-carboxymethyl)imidazolyl>azo>benzoate

Conditions

Conditions	Yield
With hydrogenchloride; sodium carbonate; sodium nitrite 2.) 4 deg C, 30 min; Multistep reaction;

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 3-Amino-N,N-dimethyl-phthalamic acid methyl ester

: 141344-46-9
N,N-dimethyl-2-carbomethoxy-6-<<2-(4-carboxymethyl)imidazolyl>azo>benzamide

Conditions

Conditions	Yield
With hydrogenchloride; sodium carbonate; sodium nitrite 2.) 4 deg C, 30 min; Multistep reaction;

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 2-amino-5-<3,5-bis(trifluoromethyl)phenyl>-1-(3-indolyl)-3-pentanone hydrochloride

: N-[(S)-4-(3,5-Bis-trifluoromethyl-phenyl)-1-(1H-indol-3-ylmethyl)-2-oxo-butyl]-2-(1H-imidazol-4-yl)-acetamide

Conditions

Conditions	Yield
With triethylamine; 1,1'-carbonyldiimidazole 1.) DMF, CH2Cl2, 2.) DMF, CH2Cl2; Multistep reaction;

: 645-65-8
2-(1H-imidazol-4-yl)acetic acid

: 541-41-3
chloroformic acid ethyl ester

: 4-(2-Ethoxycarbonyloxy-2-oxo-ethyl)-imidazole-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0 - 5℃; for 0.25h;

Imidazole-4-acetic acid Specification

The Imidazole-4-acetic acid, with the CAS registry number 645-65-8, is also known as 4-Imidazoleacetic acid and Imidazoleacetic acid (VAN). It belongs to the product category of Imidaxoles. This chemical's molecular formula is C₅H₆N₂O₂and molecular weight is 126.11. Its IUPAC name and systematic name are the same which is called 2-(1H-imidazol-5-yl)acetic acid.

Physical properties about this chemical are: (1)ACD/BCF (pH 5.5): 1; (2)ACD/BCF (pH 7.4): 1; (3)ACD/KOC (pH 5.5): 1; (4)ACD/KOC (pH 7.4): 1; (5)#H bond acceptors: 4; (6)#H bond donors: 2; (7)#Freely Rotating Bonds: 2; (8)Polar Surface Area: 65.98 Å²; (9)Index of Refraction: 1.591; (10)Molar Refractivity: 29.891 cm³; (11)Molar Volume: 88.423 cm³; (12)Surface Tension: 74.087 dyne/cm; (13)Density: 1.426 g/cm³; (14)Flash Point: 224.345 °C; (15)Enthalpy of Vaporization: 74.367 kJ/mol; (16)Boiling Point: 447.343 °C at 760 mmHg; (17)Vapour Pressure: 0 mmHg at 25°C.

Uses of Imidazole-4-acetic acid: it can be used to produce [1-(2,4-dinitro-phenyl)-1H-imidazol-4-yl]-acetic acid. This reaction will need reagent sodium bicarbonate and solvent dimethylformamide. The yield is about 72%.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: C1=C(NC=N1)CC(=O)O
(2)InChI: InChI=1S/C5H6N2O2/c8-5(9)1-4-2-6-3-7-4/h2-3H,1H2,(H,6,7)(H,8,9)
(3)InChIKey: PRJKNHOMHKJCEJ-UHFFFAOYSA-N

Product Name

Imidazole-4-acetic acid

Synthetic route

Imidazole-4-acetic acid Specification

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