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MilliporeSigma

144754

4-Phenylimidazole

97%

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About This Item

Empirical Formula (Hill Notation):
C9H8N2
CAS Number:
670-95-1
Molecular Weight:
144.17
Beilstein/REAXYS Number:
2969
EC Number:
211-580-1
MDL number:
MFCD00005197
UNSPSC Code:
12352005
PubChem Substance ID:
24848681
NACRES:
NA.22

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assay

97%

mp

128-131 °C (lit.)

solubility

acetone: soluble 25 mg/mL, clear, colorless to yellow (typical)

functional group

phenyl

SMILES string

c1ccc(cc1)-c2c[nH]cn2

InChI

1S/C9H8N2/c1-2-4-8(5-3-1)9-6-10-7-11-9/h1-7H,(H,10,11)

InChI key

XHLKOHSAWQPOFO-UHFFFAOYSA-N

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1 of 4

This Item
191434235199375357
4-Phenylimidazole 97%

Sigma-Aldrich

144754

4-Phenylimidazole

4-Nitrobenzylamine hydrochloride 97%

Sigma-Aldrich

191434

4-Nitrobenzylamine hydrochloride

7-Methoxycoumarin-4-acetic acid 97%

Sigma-Aldrich

235199

7-Methoxycoumarin-4-acetic acid

4-Amino-2,6-dimethoxypyrimidine 97%

Sigma-Aldrich

375357

4-Amino-2,6-dimethoxypyrimidine

assay

97%

assay

97%

assay

97%

assay

97%

solubility

acetone: soluble 25 mg/mL, clear, colorless to yellow (typical)

solubility

methanol:glacial acetic acid (1:1): soluble 25 mg/mL, clear, colorless to light yellow

solubility

DMF: soluble 50 mg/mL, clear, colorless to yellow

solubility

methanol: soluble 25 mg/mL, clear, colorless to yellow

mp

128-131 °C (lit.)

mp

~265 °C (dec.) (lit.)

mp

193 °C (dec.) (lit.)

mp

149-152 °C (lit.)

functional group

phenyl

functional group

amine, nitro

functional group

carboxylic acid, ester

functional group

-

Application

4-Phenylimidazole was used to investigate the protein-ligand interactions in cytochrome P450 from the thermoacidophile Picrophilus torridus[1]. It was used as heme ligand during the crystallization of recombinant human indoleamine 2,3-dioxygenase[2]. It was used in the synthesis of complexes of copper and cobalt[3].

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCT7598
MKCR8906
MKCQ1137
MKCL4115
MKCL1656

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J K Yano et al.
The Journal of biological chemistry, 275(40), 31086-31092 (2000-06-22)
The structure of the first P450 identified in Archaea, CYP119 from Sulfolobus solfataricus, has been solved in two different crystal forms that differ by the ligand (imidazole or 4-phenylimidazole) coordinated to the heme iron. A comparison of the two structures
Y K Li et al.
Biochimica et biophysica acta, 999(3), 227-232 (1989-12-21)
Over 25 nitrogen-containing heterocycles were tested as inhibitors of sweet almond beta-glucosidase (EC 3.2.1.21). Among the most potent of these are some imidazole derivatives. The pH dependence indicates that the unprotonated inhibitor binds most tightly to the catalytically active species
Y K Li et al.
Journal of biochemistry, 123(3), 416-422 (1998-05-30)
Series of 4-arylimidazoles, omega-N-acylhistamines and 4-(omega-phenylalkyl)imidazoles were synthesized in order to probe the active site topology of sweet almond beta-glucosidase. These imidazole derivatives were shown to be very powerful competitive inhibitors. Among the 20 tested compounds, omega-N-benzoylhistamine and 4-(3'-phenylpropyl)imidazole are
Danni L Harris et al.
Proteins, 55(4), 895-914 (2004-05-18)
The molecular origins of temperature-dependent ligand-binding affinities and ligand-induced heme spin state conversion have been investigated using free energy analysis and DFT calculations for substrates and inhibitors of cytochrome P450 2B4 (CYP2B4), employing models of CYP2B4 based on CYP2C5(3LVdH)/CYP2C9 crystal
M Sono et al.
Biochemistry, 28(13), 5392-5399 (1989-06-27)
The effects of norharman, one of the few known inhibitors of the heme protein indoleamine 2,3-dioxygenase, and of 4-phenylimidazole (4-PheImid), a heme ligand, on the catalytic (Vmax, Km) and spectroscopic properties (optical absorption, CD, and magnetic CD) of the rabbit
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