[ CAS No. 24155-42-8 ] {[proInfo.proName]}

Name: 24155-42-8|1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol|97%
Brand: Ambeed
SKU: A290204
Price: 5.0 USD
Availability: InStock
Rating: 92 (29 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 24155-42-8 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 24155-42-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 24155-42-8 ]

SDS Specification

Alternatived Products of [ 24155-42-8 ]

Product Details of [ 24155-42-8 ]

CAS No. :	24155-42-8	MDL No. :	MFCD00044708
Formula :	C₁₁H₁₀Cl₂N₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UKVLTPAGJIYSGN-UHFFFAOYSA-N
M.W :	257.12	Pubchem ID :	32238
Synonyms :

Calculated chemistry of [ 24155-42-8 ]

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	11
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	63.96
TPSA :	38.05 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	2.6
Log Po/w (MLOGP) :	1.86
Log Po/w (SILICOS-IT) :	2.63
Consensus Log Po/w :	2.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.41
Solubility :	0.1 mg/ml ; 0.000391 mol/l
Class :	Soluble
Log S (Ali) :	-3.09
Solubility :	0.209 mg/ml ; 0.000813 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.04
Solubility :	0.0234 mg/ml ; 0.000091 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.41

Safety of [ 24155-42-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 24155-42-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 24155-42-8 ]
Downstream synthetic route of [ 24155-42-8 ]

[ 24155-42-8 ] Synthesis Path-Upstream 1~12

1
[ 106-95-6 ]
[ 24155-42-8 ]
[ 35554-44-0 ]

Reference： [1] European Journal of Medicinal Chemistry, 1998, vol. 32, # 12, p. 1001 - 1007

2
[ 46503-52-0 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
90.5%	With potassium borohydride In methanol for 1 h; Reflux	In 1000ml of three necked flask equipped with a stirrer, thermometer, dropping funnel added 102g of 2,4-dichloro-2-imidazole-acetophenone(0.4mol) , methanol 300ml, portion wise added potassium borohydride was slowly warmed to reflux,after incubated stirring for 1 h, TLC detection reaction (Ethylacetate: methanol 10:1 (ν / ν), the reaction was completed, vacuum recovery of methanol, Concentrated liquid pH was adjusted to ph 4-5 using 5percent of hydrochloric acid, suction filtration , the filtratepH was adjusted to pH 7-8 with 5percent of sodium bicarbonate solution, there appears a white solid, it was suction filtrated , washwith darer , dried , recrystallized to obtain 1-(2,4-dichlorophenyl)-2-imidazolethanol 93.1g. yield 90.5percent, mp. 34-135°C ;
88%	With sodium tetrahydroborate In methanol for 2 h; Reflux	A solution of 15 3 (1mmol, 1eq) in 17 methanol (4ml) were added to a suspension of 16 sodium borohydride (2mmol, 1eq) in anhydrous methanol (20ml) while maintaining the temperature below 0°C. The resulting mixture was stirred at room temperature for 1h and then reflux the mixture for 1h until 3 disappeared. The reaction mixture was cooled to room temperature and 64 water was added. The 18 product was extracted with ethyl acetate (10ml×3). The combined organic phase was dried over Na₂SO₄ and purified by flash chromatography using Hexane/EtOAc (1:1) as the eluent. Yield: 88percent. Mp 130–132°C. ¹H NMR (300MHz, DMSO) δ 7.59 (d, J=1.7Hz, 1H), 7.45 (d, J=7.5Hz, 2H), 7.41 (dd, J₁=7.5Hz, J₂=1.8Hz, 1H), 7.03 (s, 1H), 6.83 (s, 1H), 6.05 (s, 1H), 5.06 (dd, J₁=7.1, J₂=3.4Hz, 1H), 4.16 (dd, J₁=14.1, J₂=3.4Hz, 1H), 4.03 (dd, J₁=14.1Hz, J₂=7.1Hz, 1H)
85%	at 3 - 20℃; for 2 h;	NaBH4 (0.21 g, 5.5 mmol) was added (in three portions) to asolution of the ketone (1.4 g, 5.5 mmol) 8 in 2-propanol (25 mL) at3–5 C. The mixture was stirred at room temperature for 2 h (monitoredby TLC). Then, 50percent of solvent was removed under reducedpressure and 3percent solution of HCl (3 mL) was added. The reactionwas neutralized with sodium carbonate and poured into water.The mixture was extracted with ethyl acetate and the organicphase was dried over anhydrous Na2SO4. The solvent was removedunder reduced pressure on a rotary evaporator to yield a viscousgum, which was recrystallized in acetone to give 13. Yield:1.19 g, 85percent.

Reference： [1] Patent: CN102180835, 2016, B, . Location in patent: Paragraph 0015; 0016
[2] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1665 - 1674
[3] Polyhedron, 2013, vol. 52, p. 106 - 114
[4] Organic and Biomolecular Chemistry, 2018, vol. 16, # 23, p. 4288 - 4294
[5] Medicinal Chemistry Research, 1999, vol. 9, # 3, p. 162 - 175
[6] Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 4, p. 1027 - 1030
[7] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 7035 - 7044
[8] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 284 - 301
[9] Chemical Science, 2017, vol. 8, # 4, p. 2687 - 2701

3
[ 288-32-4 ]
[ 13692-14-3 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
78.7%	With potassium carbonate In water; butanone	(b) An alternative method for the preparation of 1-(2',4'dichlorophenyl)2-(1H-imidazole)-1-ethanol follows. Four g (17.74 mmol) of (+-)-2-chloro-(2',4'dichlorophenyl)-1-ethanol, prepared by sodium borohydride reduction of 2,2',4'-trichloroacetophenone (purchased from Aldrich Chemical), and 5.00 g (73.44 mmol) of imidazole were dissolved in 15 mL of dry 2-butanone in a 100 mL round bottom flask equipped with a magnetic stirrer bar and reflux condenser. Four g K₂CO₃ and a catalytic amount of NaI were added and the solution was refluxed under a nitrogen atmosphere for 36 hours. After cooling to room temperature, the reaction mixture was filtered. Ether was added to the filtrate and the resulting solution was washed with 50 mL of water and the layers separated. The aqueous layer was extracted 3 times with 50 mL portions of ether. The ether extracts were combined with the previous organic phase and the total dried over anhydrous MgSO₄. After filtration to remove MgSO₄, the filtrate was concentrated to give a yellowish oil. Chromatography of the crude product (CH₂Cl₂:CH₃OH/95:5) provided 3.59 g of purified pale yellow crystals (78.7percent yield). 1-(β-Allyloxy-β-2',4'-dichlorophenylethyl)imidazole (Imazalil):

Reference： [1] Patent: US6207695, 2001, B1,
[2] Patent: US4221803, 1980, A,

4
[ 288-32-4 ]
[ 13692-15-4 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: With sodium hydride In N,N-dimethyl-formamide at 20℃; Inert atmosphere Stage #2: at 60℃; Inert atmosphere	To a mixture of sodium hydride (0.080 g, 2 mmol) in 5 mL of DMF was added imidazole (0.136 g, 2 mmol) dissolved in 2 mL of DMF. The solution was stirred for 30 min under nitrogen atmosphere at room temperature before the addition of 2- (2,4-dichlorophenyl) oxirane 2 (0.378 g, 2 mmol) dissolved in 2 mL of DMF. After, the reaction mixture was stirred at 60 °C for 22 h, TLC indicated the disappearance of the starting material. Then the solution was brought to room temperature with continuous stirring for 20 min, before DMF was removed with extractions using distilled water and AcOEt. The resulting solution was dried over anhydrous Na₂SO₄, filtered and concentrated under reduced pressure. The crude extract was then purified by flash chromatography on silica eluting with ethyl acetate/hexane 2/8 to afford the white solid 3 (0.293 g, 57percent). Rf: 0.32 (EtOAc/Hex 2/8). m.p. 124e126 C. 1H NMR: (300 MHz,DMSO-D6) d 7.59 (d, J 1.9 Hz, 1H, NeCHeN), 7.52e7.40 (m, 3H),7.05 (s, 1H, CH), 6.84 (s, 1H, CHeN), 6.07 (d, J 4.4 Hz, 1H, OH), 5.08(m, 1H), 4.18 (dd, J 14.2, 3.4 Hz, 1H, NeCH2), 4.04 (dd, J 14.1,7.1 Hz, 1H, NeCH2). 13C NMR: (75.4 MHz, DMSO-D6) d 138.61 (C),137.68 (C),132.69 (CeCl),131.75 (CeCl),129.33 (C),128.36 (C),127.91(C),127.40 (C), 119.96 (C), 68.65 (CHeOH), 51.58 (CH2) ppm.MS [EI]m/z (percent): 257 (M), 239 (2), 221 (56), 175 (58), 147 (13), 113 (8), 108(54), 82 (100), 69 (81), 54 (39), 52 (8).

Reference： [1] Organic Preparations and Procedures International, 1992, vol. 24, # 3, p. 342 - 345
[2] European Journal of Medicinal Chemistry, 2015, vol. 97, p. 275 - 279

5
[ 67035-78-3 ]
[ 13692-14-3 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	Reflux	General procedure: Asolution of halohydrins (1.0 equiv.) and ionic liquid 7 (1.0 equiv.)in anhydrous MeCN was refluxed for 10–12 h. The reaction hasbeen monitored by TLC. A 3=4 volume of solvent was removed undervacuum, the residue poured into water and extracted with ethylacetate. The organic phase was dried over anhydrous Na2SO4, distilledoff. The obtained crude product was precipitated in acetone as a white solid. Yield 68percent from 11. Yield 40percent from 12. M.p. 142–143 C. IR (KBr, cm 1): 1512 (m), 1079 (s), 845 (s), 733 (m). 1HNMR (DMSO-d6, ppm): d = 4.0–4.06 (m, 2 H, 2CH2), 5.06–5.08 (m,1 H, 1CH), 4.16 (d, J = 10.8 Hz, 1 H, OH), 6.03 (d, J = 4 Hz, 1 H, 4CHof the imidazole ring), 6.83 (d, J = 4 Hz, 1 H, 5CH of the imidazolering), 7.03 (s, 1 H, 2CH), 7.42–7.46 (m, 2 H, 5CH, 6CH). 7.59 (s, 1H, 3CH). 13C NMR (DMSO-d6, ppm): d = 137.14 (6C), 136.20 (1C),132.99 (10C), 130.11 (7C), 130.01 (2C), 129.68 (8C), 128.04 (11C),126.12 (9C), 118.44 (3C) 63.88 (5C); 53.22 (4C). Anal. Calc. for C11-H10Cl2N2O (257.12): C, 51.38; H, 3.92; N, 10.89; Found C, 51.39;H, 3.92; N, 10.90percent.

Reference： [1] Polyhedron, 2013, vol. 52, p. 106 - 114

6
[ 67035-78-3 ]
[ 53066-15-2 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	Reflux	General procedure: Asolution of halohydrins (1.0 equiv.) and ionic liquid 7 (1.0 equiv.)in anhydrous MeCN was refluxed for 10–12 h. The reaction hasbeen monitored by TLC. A 3=4 volume of solvent was removed undervacuum, the residue poured into water and extracted with ethylacetate. The organic phase was dried over anhydrous Na2SO4, distilledoff. The obtained crude product was precipitated in acetone as a white solid. Yield 68percent from 11. Yield 40percent from 12. M.p. 142–143 C. IR (KBr, cm 1): 1512 (m), 1079 (s), 845 (s), 733 (m). 1HNMR (DMSO-d6, ppm): d = 4.0–4.06 (m, 2 H, 2CH2), 5.06–5.08 (m,1 H, 1CH), 4.16 (d, J = 10.8 Hz, 1 H, OH), 6.03 (d, J = 4 Hz, 1 H, 4CHof the imidazole ring), 6.83 (d, J = 4 Hz, 1 H, 5CH of the imidazolering), 7.03 (s, 1 H, 2CH), 7.42–7.46 (m, 2 H, 5CH, 6CH). 7.59 (s, 1H, 3CH). 13C NMR (DMSO-d6, ppm): d = 137.14 (6C), 136.20 (1C),132.99 (10C), 130.11 (7C), 130.01 (2C), 129.68 (8C), 128.04 (11C),126.12 (9C), 118.44 (3C) 63.88 (5C); 53.22 (4C). Anal. Calc. for C11-H10Cl2N2O (257.12): C, 51.38; H, 3.92; N, 10.89; Found C, 51.39;H, 3.92; N, 10.90percent.

Reference： [1] Polyhedron, 2013, vol. 52, p. 106 - 114

7
[ 4252-78-2 ]
[ 24155-42-8 ]

Reference： [1] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 7035 - 7044
[2] Polyhedron, 2013, vol. 52, p. 106 - 114
[3] Patent: CN102180835, 2016, B,
[4] Chemical Science, 2017, vol. 8, # 4, p. 2687 - 2701
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 23, p. 4288 - 4294

8
[ 2631-72-3 ]
[ 24155-42-8 ]

Reference： [1] Polyhedron, 2013, vol. 52, p. 106 - 114
[2] European Journal of Medicinal Chemistry, 2014, vol. 84, p. 284 - 301
[3] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1665 - 1674

9
[ 874-42-0 ]
[ 24155-42-8 ]

Reference： [1] European Journal of Medicinal Chemistry, 2015, vol. 97, p. 275 - 279

10
[ 2234-16-4 ]
[ 24155-42-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2018, vol. 26, # 8, p. 1665 - 1674

11
[ 94-99-5 ]
[ 24155-42-8 ]
[ 22916-47-8 ]

Reference： [1] Organic Preparations and Procedures International, 1992, vol. 24, # 3, p. 342 - 345

12
[ 24155-42-8 ]
[ 22916-47-8 ]

Reference： [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 23, p. 4288 - 4294

[ 24155-42-8 ] Synthesis Path-Downstream 1~87

1
[ 17512-61-7 ]
[ 24155-42-8 ]
[ 99592-32-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide;tetra(n-butyl)ammonium hydrogensulfate; In toluene; at 35 - 40℃; for 3.25h;	Example 1: Sertaconazole mononitrate monohydrate (V) (Sertaconazole mononitrate pseudopolymorph)A 2-L flask was loaded with 308 mL of toluene, 100 g of 1- (2,4-dichlorophenyl) -2- (lH-imidazol-1-yl) -ethanol (II) (0.389 mol) and 6.67 g of tetrabutylammonium hydrogen sulfate (IV, Z = HSO4) (0.0196 mol) . Then, 155 g of sodium hydroxide (purity 49%; 1.905 mol) were added. The mixture was heated at 35-4O0C and stirred for 15 minutes. A solution comprising 111.11 g of 3-bromomethyl-7- chlorobenzo [Jb] thiophene (III) (0.425 mol) and 595 mL of toluene, maintaining the mass temperature between 37 and 400C, was added for at least 30 minutes. After the addition, the system was maintained between 37 and 400C for 2.5 hours and thereafter water (635 mL ) was added. The mixture was cooled to a mass temperature of 5-100C and the sertaconazole precipitated was filtered and washed with water and cold toluene (5-1O0C), obtaining 179.7 g of wet sertaconazole free base(161.7 g dry) . The sertaconazole free base obtained was loaded into a 2 L reactor containing 848 mL of absolute ethanol. The mixture was refluxed until complete dissolution. Then the mixture was heated at a mass temperature between 68 and 72C, and 236 mL of water were added. The mixture was cooled at 100C and this temperature was maintained for 1 hour. The solid material formed was filtered and washed with a solution of 160 mL of absolute ethanol and 51 mL of water previously- cooled at 100C. Wet pure sertaconazole free base (177.9 g) was obtained (158 g dry) . The obtained pure sertaconazole free base was loaded into a 2 L reactor and re-dissolved with 932 mL of absolute ethanol at 750C. The mixture was then cooled at a mass temperature of 67-700C and a solution containing 53.7 g (0.512 mol) of 60% nitric acid in 193 mL of water is added. The temperature was stabilized for 15 minutes, checking that the pH was maintained below 2. The mixture was cooled at 100C and kept for 1 hour. The precipitated material was filtered and washed with water, providing 215.9 g of sertaconazole mononitrate monohydrate (V) (Sertaconazole mononitrate pseudopolymorph) . Yield 88.7%.Analytical dataIR (infrared) : A Magna-IR 550 Nicolet spectrometer with a database running in Omnic 2.1 software has been used. The recorded IR spectrum of sertaconazole mononitrate monohydrate (V) compared to sertaconazole mononitrate (I) is shown in Figure 2/5.DSC (differential scanning calorimetry) : A Mettler' TA-8000 instrument comprising DSC-820 and TG-50 components, and a MT-5 balance provided with a database running in TAS 810 1.1 software has been used. A product sample of 1 to 5 mg was weighted in a 40 muL aluminum crucible, maintaining the following conditions: Temperature range: 110-1800C Heating speed: 100C / min Nitrogen flow: 100 mL / min The recorded DSC of sertaconazole mononitrate monohydrate (V) compared to sertaconazole mononitrate (I) is shown in Figure 3/5.Microscopy: A Nikon-Eclipse E-600 unit with polarized light, provided with a Linkam THMS 600 heating plate and a Linksys database and image manager software has been used. Some product particles were suspended in mineral oil on a glass slide and the sample was examined by magnification depending on the particle size and using polarized light or not . Sertaconazole mononitrate monohydrate (V) and sertaconazole mononitrate (I) microphotographs are shown in Figure 4/5.X Rays Diffraction: A Siemens powder X Ray Diffraction Equipment model D-500 has been used. The X Rays diffractograms for sertaconazole mononitrate monohydrate (V) and sertaconazole mononitrate (I) are shown in Figure 5/5. The crystal data and structure refinement for sertaconazole mononitrate monohydrate (V) are shown in Table 2. Table2Crystal data and structure refinement for sertaconazole mononitrate monohydrate (V) Empirical formula C20H15CI3N2OS. HNO3. H2O Formula weight 518.78 Temperature 293(2)K Wavelength 0.71069 A Crystal system Monoclinic Space group P2i/c a = 16.049(2)A alpha = 90 Unit cell dimensions b = 8.946(7)A beta = 102.046(7) c = 15.990(3) A Y = 90 Volume 2245(2) A3 Z 4 Density (calculated) 1.535 Mg/m3 Absorption coefficient 0.540 mm"1 Crystal size 0.1 x 0.1 x 0.2 mm Theta range for data collection 1.30 to 30.07 Index ranges -3<h<16, -12<k<12, -22<l<21 Reflections collected 11440 Independent reflections 5861 [R(int) = 0.1748] Refinement method Full-matrix least-squares on F2 Data / restraints / parameters 3246 / 1 /336 Goodness-of-fit on F2 0.980 Final R indices [l>2?(l)] R1 = 0.0644, WR2 = 0.1302 R indices (all data) R1 = 0.3270, WR2 = 0.2365 Extinction coefficient 0.0000(6) Largest diff. peak and hole 0.356 and -0.429 e.A3

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332
[2]Arzneimittel-Forschung/Drug Research,1992,vol. 42,p. 691 - 694
[3]Patent: WO2006/29812,2006,A1 .Location in patent: Page/Page column 6

2
[ 1527-15-7 ]
[ 110-16-7 ]
[ 24155-42-8 ]
1-[2-(2,4-Dichloro-phenyl)-2-(2-phenylsulfanyl-benzyloxy)-ethyl]-1H-imidazole; compound with (Z)-but-2-enedioic acid [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

3
[ 1196-19-6 ]
[ 24155-42-8 ]
[ 99592-24-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

4
[ 1198-51-2 ]
[ 24155-42-8 ]
[ 99597-51-0 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

5
[ 10133-20-7 ]
[ 24155-42-8 ]
[ 99592-23-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

6
[ 3446-75-1 ]
[ 24155-42-8 ]
1-[2-(2,4-Dichloro-phenyl)-2-(4-ethylsulfanyl-benzyloxy)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

7
[ 1667-11-4 ]
[ 24155-42-8 ]
[ 73151-17-4 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

8
[ 7435-83-8 ]
[ 24155-42-8 ]
1-[2-(2,4-Dichloro-phenyl)-2-(2,3,5,6-tetramethyl-benzyloxy)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

9
[ 13692-14-3 ]
[ 24155-42-8 ]
1,3-bis-<β-(2,4-dichlorophenyl)-β-hydroxyethyl>imidazolium chloride [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1981,vol. 31,p. 2127 - 2133

10
[ 80676-35-3 ]
[ 24155-42-8 ]
1-[2-(2,4-Dichloro-phenyl)-2-(4-phenethyl-benzyloxy)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

11
[ 50265-01-5 ]
[ 24155-42-8 ]
1-[2-(4-Chloro-naphthalen-1-ylmethoxy)-2-(2,4-dichloro-phenyl)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

12
[ 1208-87-3 ]
[ 24155-42-8 ]
1-(β-hydroxyethyl-β,2,4-dichlorophenylethyl)-3-(4-phenylthiobenzyl)imidazolium chloride [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1981,vol. 31,p. 2127 - 2133

13
[ 1208-87-3 ]
[ 24155-42-8 ]
1-(β-hydroxyethyl-β,2,4-dichlorophenylethyl)-3-(4-phenylthiobenzyl)imidazolium chloride [ No CAS ]
1-<β-(2,4-dichlorophenyl)-β-(4-phenylthiobenzyloxy)-ethyl>-3-(4-phenylthiobenzyl)imidazolium chloride [ No CAS ]
α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobezyl ether nitrate [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1981,vol. 31,p. 2127 - 2133

14
[ 1208-87-3 ]
[ 24155-42-8 ]
[ 72479-26-6 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

15
[ 1208-87-3 ]
[ 24155-42-8 ]
1-(β-hydroxyethyl-β,2,4-dichlorophenylethyl)-3-(4-phenylthiobenzyl)imidazolium chloride [ No CAS ]
1-<β-(2,4-dichlorophenyl)-β-(4-phenylthiobenzyloxy)-ethyl>-3-(4-phenylthiobenzyl)imidazolium chloride [ No CAS ]
[ 72479-26-6 ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1981,vol. 31,p. 2127 - 2133

16
[ 100415-75-6 ]
[ 24155-42-8 ]
[ 71821-41-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1982,vol. 17,p. 139 - 143

17
[ 83450-19-5 ]
[ 24155-42-8 ]
[ 99597-52-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

18
[ 99592-54-8 ]
[ 24155-42-8 ]
[ 99592-37-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

19
[ 99592-53-7 ]
[ 24155-42-8 ]
[ 99592-34-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

20
6-bromo-2-(bromomethyl)benzo[b]thiophene [ No CAS ]
[ 24155-42-8 ]
[ 99597-59-8 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

21
[ 102246-36-6 ]
[ 24155-42-8 ]
[ 99597-60-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

22
[ 102246-39-9 ]
[ 24155-42-8 ]
[ 100013-19-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

23
[ 102246-40-2 ]
[ 24155-42-8 ]
[ 99651-89-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

24
[ 17512-59-3 ]
[ 24155-42-8 ]
[ 99597-54-3 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

25
4-Bromo-2-bromomethyl-benzo[b]thiophene [ No CAS ]
[ 24155-42-8 ]
[ 99597-57-6 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

26
[ 102246-43-5 ]
[ 24155-42-8 ]
[ 99597-55-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

27
[ 20896-08-6 ]
[ 24155-42-8 ]
[ 99597-53-2 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

28
[ 99592-52-6 ]
[ 24155-42-8 ]
[ 104907-75-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

29
[ 20896-07-5 ]
[ 24155-42-8 ]
[ 99592-26-4 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

30
[ 82071-05-4 ]
[ 24155-42-8 ]
[ 73437-73-7 ]

Reference： [1]European Journal of Medicinal Chemistry,1982,vol. 17,p. 139 - 143

31
2-Bromomethyl-4,6-dichloro-benzo[b]thiophene [ No CAS ]
[ 24155-42-8 ]
[ 99597-56-5 ]

Reference： [1]European Journal of Medicinal Chemistry,1986,vol. 21,p. 329 - 332

32
[ 73437-83-9 ]
[ 24155-42-8 ]
[ 73437-93-1 ]

Reference： [1]European Journal of Medicinal Chemistry,1982,vol. 17,p. 139 - 143

33
[ 24155-42-8 ]
[ 939-26-4 ]
1-[2-(2,4-Dichloro-phenyl)-2-(naphthalen-2-ylmethoxy)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126

34
[ 24155-42-8 ]
[ 86-52-2 ]
1-[2-(2,4-Dichloro-phenyl)-2-(naphthalen-1-ylmethoxy)-ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Arzneimittel-Forschung/Drug Research,1982,vol. 31,p. 2123 - 2126
[2]European Journal of Medicinal Chemistry,1995,vol. 30,p. 955 - 962

35
[ 38641-73-5 ]
[ 24155-42-8 ]
1-[1-(2,4-Dichloro-phenyl)-2-imidazol-1-yl-ethoxymethyl]-1H-benzoimidazole [ No CAS ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 489 - 492

36
1-(chloromethyl)-2-methylbenzimidazole [ No CAS ]
[ 24155-42-8 ]
1-[1-(2,4-Dichloro-phenyl)-2-imidazol-1-yl-ethoxymethyl]-2-methyl-1H-benzoimidazole [ No CAS ]

Reference： [1]Il Farmaco,1994,vol. 49,p. 489 - 492

37
[ 94-99-5 ]
[ 24155-42-8 ]
[ 22916-47-8 ]

Reference： [1]Organic Preparations and Procedures International,1992,vol. 24,p. 342 - 345

38
[ 2567-29-5 ]
[ 24155-42-8 ]
[ 73151-17-4 ]

Reference： [1]Medicinal Chemistry Research,1999,vol. 9,p. 162 - 175

39
[ 4252-78-2 ]
[ 24155-42-8 ]

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 7035 - 7044
[2]Polyhedron,2013,vol. 52,p. 106 - 114
[3]Patent: CN102180835,2016,B
[4]Chemical Science,2017,vol. 8,p. 2687 - 2701
[5]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4288 - 4294
[6]European Journal of Medicinal Chemistry,2020,vol. 198

40
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
[ 94038-16-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

41
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
1-(2,4-dichloro-phenyl)-3-[1-(2,4-dichloro-phenyl)-2-imidazol-1-yl-ethyl]-thiourea [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

42
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
C₁₉H₁₅Cl₃N₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

43
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
C₁₉H₁₅Cl₃N₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

44
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
C₁₉H₁₅Cl₃N₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

45
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
C₁₉H₁₄Cl₄N₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

46
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
C₁₉H₁₄Cl₄N₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1027 - 1030

47
[ 24155-42-8 ]
n-butyl halide [ No CAS ]
O-[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethyl]hydroxylamine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4903 - 4912

48
[ 24155-42-8 ]
6-fluoro-3-(halomethyl)benzo<b>thiophene [ No CAS ]
1-[2-(2,4-dichlorophenyl)-2-(3,7-dimethyloctyloxy)ethyl]-1H-imidazole [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2000,vol. 48,p. 60 - 64

49
[ 24155-42-8 ]
[ 27656-21-9 ]

Yield	Reaction Conditions	Operation in experiment
37%		Example 1: R- (-) -1- (2,4-dichlorophenyl) -2- (lH-imidazol-1- yl) -ethanol (VI); To a solution of 5 g of 1- (2, 4-dichlorophenyl) -2- (IH- imidazol-1-yl) -ethanol (II) in a mixture of acetone- methanol, 3.21 g of D-tartaric acid dissolved in a mixture of acetone-methanol were added at room temperature. Once the addition was completed, the mixture was stirred for further 30 minutes at room temperature. The resultant solid was filtered and crystallized from methanol. A mixture consisting of the resulting salt, water and methylene chloride was treated with a concentrated solution of sodium hydroxide. The organic layer was washed with water and concentrated at reduced pressure to yield 1.85 g (37%) of (VI) whose enantiomeric purity was higher than 98% in R- {-) isomer.

Reference： [1]Patent: WO2006/29811,2006,A1 .Location in patent: Page/Page column 9

50
[ 77470-53-2 ]
[ 56-93-9 ]
[ 7440-44-0 ]
[ 24155-42-8 ]
[ 77470-54-3 ]

Yield	Reaction Conditions	Operation in experiment
12.8 g (71%)	With sodium hydroxide; ethereal hydrochloric acid; In tetrahydrofuran; water;	In a three-necked flask, fitted with stirrer, reflux condenser and gas inlet tube, 44 g of sodium hydroxide (1.1 mol) and 50 ml of water are introduced. While passing nitrogen through the flask, the solution is cooled to 45 and then 11.6 g of (1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.045 mol) [prepared by the method of J. Med. Chem. 12, 784, (1969)], 0.75 g of benzyltrimethylammonium chloride and 150 ml of tetrahydrofuran are added. To the mixture, which is warmed to 50, 8.3 g of 4-chloromethyl-2-methylthiazole, hydrochloride (0.045 mol) are added and the mixture is stirred vigorously for two hours at 60. The filtered biphasic solution is transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml of tetrahydrofuran. The combined tetrahydrofuran layers are treated with charcoal and after drying with sodium sulphate, the solvent is evaporated in vacuo. The resulting oily product, dissolved in 250 ml of ether, is allowed to stand overnight in a refrigerator, by which operation unreacted 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol is separated. Filtering off and addition of ethereal hydrochloric acid to the clear ethereal solution yields the hydrochloride of 4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-methylthiazole. Yield: 12.8 g (71%).

Reference： [1]Patent: US4307105,1981,A

51
[ 534-07-6 ]
[ 2227-79-4 ]
[ 24155-42-8 ]
[ 77470-57-6 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 3 4-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)-ethoxy]methyl]-2-phenylthiazole, hydrochloride (1:1) Following the procedure of Example 1b, 4-chloromethyl-2-phenylthiazole (prepared according to Example 1a from thiobenzamide and 1,3-dichloroacetone, m.p. 134-136 C. (absolute alcohol/ethylacetate), is reacted with 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol to obtain the title compound, m.p. 204-205 C. (absolute alcohol/ethyl acetate).

Reference： [1]Patent: US4307105,1981,A

52
[ 3747-74-8 ]
[ 56-93-9 ]
[ 24155-42-8 ]
2-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water;	EXAMPLE 5 2-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:2) 3.2 g of 2-Chloromethylquinoline hydrochloride (0.015 mol) (commercially available), 3.85 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 14.8 g sodium hydroxide (0.37 mol) in 25 ml of water, 0.25 g of benzyltrimethylammonium chloride and 40 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up, the oily product (6.4 g) is dissolved in 150 ml of ether, charcoaled and then etheral hydrochloric acid is added to the clear solution while stirring. The precipitated hydrochloride (5.8 g) is filtered off, washed with ether and hexane and recrystallized from acetonitrile; m.p. 148-149 C. The following additional products of formula D or E are obtained by the procedure of Example 1 by reacting the unsubstituted or substituted 1-phenyl-2-(1H-imidazol-1-yl)ethanol of formula A with the unsubstituted or substituted 2-chloromethylquinoline of formula B or the unsubstituted or substituted 4-chloromethylquinoline of formula C. The substituents apply to the respective formulae.

Reference： [1]Patent: US4282230,1981,A

53
[ 20151-11-5 ]
[ 56-93-9 ]
[ 24155-42-8 ]
2-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water;	EXAMPLE 1 2-Chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline In a three necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced 30 g of sodium hydroxide (0.75 mol) and 30 ml of water. While passing nitrogen through the flask, the solution is cooled to 45 C. and then are added 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 0.5 g of benzyltrimethylammonium chloride, 100 ml of tetrahydrofuran and 6.4 g of 2-chloro-4-chloromethylquinoline (0.03 mol). Then the mixture is stirred vigorously for 1.5 hours at 60-65 C. After cooling the mixture is separated, and the lower aqueous sodium hydroxide is extracted with 20 ml of tetrahydrofuran. The combined tetrahydrofuran layers are dried with sodium sulfate, charcoaled, filtered and after the solvent has been removed, the residual oil is extracted with 175 ml of ether, and the etheral solution is allowed to stand overnight in a refrigerator. The crystallized 2-chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline is recrystallized from ethyl acetate (refrigerator). Yield 5.5 g (42.3%); m.p. 180-181 C.

Reference： [1]Patent: US4282230,1981,A

54
4-bromomethyl-2,6-dichloroquinoline [ No CAS ]
[ 56-93-9 ]
[ 24155-42-8 ]
[ 78649-52-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water;	EXAMPLE 2 2,6-Dichloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:1) 8.7 g of 4-bromomethyl-2,6-dichloroquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g of sodium hydroxide (0.75 mol) dissolved in 30 ml water, 0.5 g of benzyltrimethylammonium chloride and 100 ml of tetrahydrofuran are reacted as described in Example 1. Work up of the mixture results in an oil, which after treatment in boiling ether, is dissolved in 250 ml of ethyl acetate.

Reference： [1]Patent: US4282230,1981,A

55
[ 23976-52-5 ]
[ 56-93-9 ]
[ 24155-42-8 ]
6-Chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-quinolinol, hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ammonium hydroxide; sodium hydroxide; In tetrahydrofuran; water; ethyl acetate; acetonitrile;	EXAMPLE 3 6-Chloro-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-quinolinol, hydrochloride (1:1.5) 4.1 g of 4-bromomethyl-6-chloro-2-hydroxyquinoline (0.015 mol), 3.9 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol), 15.2 g of sodium hydroxide (0.38 mol) in 15 ml of water, 0.25 g of benzyltrimethylammonium chloride and 50 ml of tetrahydrofuran are reacted in a manner similar to the procedure of Example 1. After work up of the mixture, the oily product is treated with water and ether. To the aqueous layer is added half concentrated hydrochloric acid (pH 5) and subsequently aqueous ammonia (10%) for neutralization of the hydrochloride. The deposited oily product is extracted with chloroform and the chloroform layer is washed with water, dried and charcoaled. Then the solvent is removed in vacuo, the solid product dissolved in ethyl acetate and to the clear solution is added etheral hydrochloric acid. The precipitated hydrochloride (3.4 g) is washed with ethyl acetate, treated with boiling acetonitrile and then with anhydrous ether. The filtered off product, which contains two moles of crystal water, is dried at 70-75 C.; m.p. 176-178 C.

Reference： [1]Patent: US4282230,1981,A

56
[ 4876-10-2 ]
[ 56-93-9 ]
[ 24155-42-8 ]
4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-quinolinol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water; ethyl acetate;	EXAMPLE 4 4-[[1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-quinolinol 7.2 g of 4-bromomethyl-2-hydroxyquinoline (0.03 mol), 7.7 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol), 30 g sodium hydroxide (0.75 mol) in 30 ml of water, 0.5 g benzyltrimethylammonium chloride and 45 ml of tetrahydrofuran are reacted in a manner as described in Example 1. After work up of the reaction mixture the sodium salt of the title compound is dissolved in 400 ml of water and acidified with acetic acid. After standing overnight, the solution is filtered and then neutralized with aqueous ammonia. The deposited oil is extracted with chloroform, the chloroform layer washed with water, dried with sodium sulfate and evaporated. The residual oil (8 g) is dissolved in 100 ml of ethyl acetate, charcoaled and allowed to stand overnight in the refrigerator. The crystallized 4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-quinolinol melts at 190-192 C.

Reference： [1]Patent: US4282230,1981,A

57
[ 24155-42-8 ]
[ 77470-58-7 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 4 2-(4-Chlorophenyl)-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]thiazole, hydrochloride (1:1) Following the procedure of Example 1b, 4-chloromethyl-2-(4-chlorophenyl)thiazole (m.p. 66) is reacted with 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol to yield the title compound, m.p. 108-110 C. (acetonitrile).

Reference： [1]Patent: US4307105,1981,A

58
3-bromomethyl-4,6-dichlorobenzofuran [ No CAS ]
[ 24155-42-8 ]
1-[2,4-dichloro-β-[(4,6-dichlorobenzofuran-3-yl)methoxy]phenethyl]imidazole nitrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With nitric acid; In N-methyl-acetamide; diethyl ether; water; acetic acid; ethyl acetate; mineral oil;	EXAMPLE 1 A stirred solution of 0.51 g (0.002 mol) of 2,4-dichloro-alpha-[(1-imidazolyl)methyl]benzyl alcohol was cooled to 0 C. and treated with 48 mg (0.002 mol) of sodium hydride (60 mg of an 80% dispersion in mineral oil). Stirring was continued and, after the effervescence had ceased (about 0.5 hour), the mixture was treated with a solution of 0.56 g (0.002 mol) of 3-bromomethyl-4,6-dichlorobenzofuran in 2 ml of dry dimethylformamide. The mixture was stirred at 0 C. for 0.5 hour and then at room temperature for 2 hours. The mixture was treated with 50 ml of water containing 0.5 ml of glacial acetic acid and then saturated with sodium chloride. The product was extracted with three 30 ml portions of ethyl acetate. The combined ethyl acetate extracts were washed with brine, dried over sodium sulphate and evaporated at 30 C./12 mmHg to give a pale brown viscous oil. This oil was dissolved in 15 ml of dry diethyl ether by the addition of the minimum volume of ethyl acetate and treated with 0.2 ml of concentrated nitric acid. The precipitated product was crystallized from ethanol to yield 0.57 g of 1-[2,4-dichloro-beta-[(4,6-dichlorobenzofuran-3-yl)methoxy]-phenethyl]imidazole nitrate of melting point 105 C. The 2,4-dichloro-alpha-[(1-imidazolyl)methyl]benzyl alcohol used as the starting material can be prepared according to Godefroi et al, J. Med. Chem. 784,12, (1969). The 3-bromomethyl-4,6-dichlorobenzofuran used as the starting material can be prepared as follows:

Reference： [1]Patent: US4402968,1983,A

59
5-bromo-4-(chloromethyl)-2-methylthiazole [ No CAS ]
[ 24155-42-8 ]
[ 77470-59-8 ]

Yield	Reaction Conditions	Operation in experiment
		(b) 5-Bromo-4-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-2-methylthiazole, hydrochloride (1:1) Following the procedure of Example 1b, reaction of 5-bromo-4-chloromethyl-2-methylthiazole and 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol, yields the title compound, m.p. 247-248 C. (absolute ethanol).

Reference： [1]Patent: US4307105,1981,A

60
[ 73998-96-6 ]
base alcoholic hydrochloric acid [ No CAS ]
[ 56-93-9 ]
[ 7440-44-0 ]
[ 24155-42-8 ]
[ 73998-98-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; water;	In a three-necked flask, fitted with stirrer, reflux condenser and gas inlet tube 29.3 g. of sodium hydroxide (0.73 mol.) and 27 ml. of water are introduced. While passing nitrogen through the flask, the solution is cooled to 45 and then 7.71 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.03 mol.) [prepared by the method of J. Med. Chem. 12, 784 (1969)], 0.5 g. of benzyltrimethylammonium chloride and 30 ml. of tetrahydrofuran are added. To the mixture, which is warmed to 50, 5.9 g. of 5-chloromethyl-2,4-dichloropyridine are added and the mixture is stirred vigorously for two hours at 60. The filtered biphasic solution is transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml. of tetrahydrofuran. The combined tetrahydrofuran layers are treated with charcoal and dried by means of sodium sulfate. Ether is then added to the tetrahydrofuran extract in order to remove an oily by-product. To the clear solution of the free base alcoholic hydrochloric acid is added dropwise. The precipitated 2,4-dichloro-5-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethoxy]-methyl]pyridine, hydrochloride (3.5 g.) is treated with acetonitrile. A second crop is obtained by removing the tetrahydrofuran/alcohol mother liquor and treating the residue with acetonitrile (3.5 g.), m.p. 177. Total yield 7 g. (52%). Recrystallization from acetonitrile elevates the melting point to 181-182.

Reference： [1]Patent: US4191831,1980,A

61
[ 56-93-9 ]
[ 7440-44-0 ]
[ 63928-56-3 ]
[ 24155-42-8 ]
[ 72444-77-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethereal hydrochloric acid; In tetrahydrofuran; water;	(b) 4-Chloro-5-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]pyridine, hydrochloride (1:1) In a three necked flask (250 ml.), fitted with a stirrer, reflux condenser and gas inlet tube are introduced 24.4 g. of sodium hydroxide (0.61 mol.) and 23 ml. of water. While passing nitrogen through the flask, the solution is cooled to 45 and then are added 6.43 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.025 mol.), [prepared according to J. Med. Chem., Vol. 12, 784 (1969)], 0.43 g. of benzyltrimethylammonium chloride and 25 ml. of tetrahydrofuran. To the mixture, which is warmed to 50, a solution of 6.1 g. of 4-chloro-5-chloromethyl-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]-pyridine (0.025 mol.) in 10 ml. of tetrahydrofuran is added from a prewarmed dropping funnel within 3 minutes. The mixture is stirred vigorously for 3 hours at 60 using a water bath. Then the warm mixture is transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml. of tetrahydrofuran. The combined tetrahydrofuran layers are dried by means of sodium sulfate and after the solvent has been removed the residual oil is extracted with ether, treated with charcoal and filtered. To the solution of free base are added dropwise 5.9 ml. of ethereal hydrochloric acid (30.9%). The precipitated 4-chloro-5[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]- 1-ethyl-3-methyl-1H-pyrazolo[3,4-b]pyridine, hydrochloride is filtered off, dried in the vacuum desiccator and recrystallized from acetonitrile, m.p. 200-201; yield 5.67 g. (45%).

Reference： [1]Patent: US4159380,1979,A

62
[ 71422-83-8 ]
[ 7440-44-0 ]
[ 24155-42-8 ]
5-[[1-(2,4-Dichlorophenyl)-2H-(1H-imidazol-1-yl)ethoxy]methyl]-1-ethyl-3-methyl-1H-pyrazolo-[3,4-b]pyridine, hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ethereal hydrochloric acid;	(d) 5-[[1-(2,4-Dichlorophenyl)-2H-(1H-imidazol-1-yl)ethoxy]methyl]-1-ethyl-3-methyl-1H-pyrazolo-[3,4-b]pyridine, hydrochloride 7.71 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol (0.03 mol.) and 7.4 g. of 5-chloromethyl-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]-pyridine, hydrochloride (0.03 mol.) are reacted according to the procedure of Example 1b. The combined tetrahydrofuran layers are treated with charcoal, filtered and dried with sodium sulfate. After addition of 300 ml. of ether and filtering over charcoal, the filtrate containing the free base is mixed with 8 ml. of ethereal hydrochloric acid (415 g. HCl/1) (0.09 mol.). The precipitated 5-[[1-(2,4-dichlorophenyl)-2H-(1H-imidazol-1-yl)-ethoxy]methyl]-1-ethyl-3-methyl-1H-pyrazolo[3,4-b]-pyridine, hydrochloride (14.8 g.) is treated with ether, filtered off, dried in the vacuum desiccator and recrystallized from acetone; m.p. 158-159 (dec.); yield: 8.11 g. (58%).

Reference： [1]Patent: US4159380,1979,A

63
[ 765-50-4 ]
[ 24155-42-8 ]
[ 61747-01-1 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	EXAMPLE 1 A solution of 1-(2,4-dichloro-phenyl)-2-(1-imidazolyl) ethanol (1.5 g, 5.8mmole) dissolved in dry tetrahydrofuran (10 ml) was added to a stirred suspension of sodium hydride (0.39 g, as 80% dispersion in oil, 16 mmole) in dry tetrahydrofuran (10 ml) and warmed to 70 C for 90 minutes. The mixture was cooled in ice and a solution of 2-chloromethyl-thiophene (1.16 g, 8.8 mmole) in dry tetrahydrofuran was added. The mixture was heated at 70 for 3 hours and allowed to stir at room temperature overnight. The solvent was removed under vacuum and the residue stirred with dry ether (200 ml). The ether solution was filtered through celite and saturated with hydrogen chloride gas to precipitate an oil which was solidified by trituration with ether and ethylacetate. The solid product was collected and recrystallized from a mixture of acetone and di-isopropyl ether to give 1-[2,4-dichloro-beta-(2-thienylmethoxy)phenethyl]imidazole hydrochloride as fine white crystals (0.63 g, 31%) m.p. 153-154 C. (Found: C, 49.2; H, 3.8; N, 7.3. C16 H14 Cl2 N2 OS.HCl requires C, 49.3; H, 3.9; N, 7.2%).

Reference： [1]Patent: US4062966,1977,A

64
ethereal oxalic acid [ No CAS ]
[ 24155-42-8 ]
[ 2812-73-9 ]
1-[2,4-dichloro-β-(ethoxythiocarbonyloxy)phenethyl]imidazole oxalate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; mineral oil;	A. two hundred forty (240) mg of a dispersion of 56% w sodium hydride in mineral oil is added to 1.30g of 1-[2,4-dichloro-beta-hydroxyphenethyl]imidazole in 10 ml. hexamethylphosphoramide under nitrogen and the mixture stirred at 10-25 C. for 1 hour and at 50 C. for a further 1 hour. The resulting solution is then cooled to ca. 5 C. and treated dropwise with 685mg. of O-ethyl chlorothioformate and the mixture stirred 1 hour at room temperature and at 40 for 1-2 hours. The mixture is poured into water, extracted with ether and the extracts washed with water, dried over magnesium sulfate and evaporated. The product is purified by chromatography on silica gel eluding with 10-15% acetone in dichloromethane. The oxalate salt is precipitated by addition of ethereal oxalic acid to the product in ether until precipitation is complete. Recrystallization from ethyl acetate/acetone gives crystals of 1-[2,4-dichloro-beta-(ethoxythiocarbonyloxy)phenethyl]imidazole oxalate. B. by following the procedure of part A of this example but employing other appropriate O-hydrocarbyl chlorothioformates, the following products may be prepared: 1-[2,4-dichloro-beta-(n-propoxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(n-butoxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(n-pentyloxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(n-hexyloxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(n-heptyloxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(p-chlorophenoxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(2,4-dichlorophenoxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(3,4-dichlorophenoxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(p-chlorobenzyloxythiocarbonyloxy)phenethyl]imidazole; 1-[2,4-dichloro-beta-(2,4-dichlorobenzyloxythiocarbonyloxy)phenethyl]imidazole; and

Reference： [1]Patent: US4039677,1977,A

65
[ 3364-76-9 ]
[ 24155-42-8 ]
[ 61675-70-5 ]

Yield	Reaction Conditions	Operation in experiment
46%	With hydrogenchloride; In tetrahydrofuran;	EXAMPLE 11 A solution of 1-(2,4-dichloro-phenyl)-2-(1-imidazolyl) ethanol (2.4 g, 9.4 mmole) in dry tetrahydrofuran (20 ml) was added to sodium hydride (0.62 g, as an 80% dispersion in oil, 0.02 mole) and warmed at 70 C for 90 minutes. The solution was cooled to 0 C and 4-chloromethylthiazole (1.5 g, 11.2 mmole), dissolved in a little dry tetrahydrofuran, was added. The mixture was stirred at 0 C for 1 hour and at room temperature for 6 hours. Further 4-chloromethylthiazole (0.25 g) was added and the stirring continued for 36 hours. The reaction mixture was then diluted with water (70 ml) and extracted several times with ether. The ether extracts were combined, dried over MgSO4 and evaporated. The oily residue was taken up in dry ether (50 ml) and treated with a solution of HCl in ether. The solid precipitate was collected and recrystallized from a mixture of methanol and di-isopropyl ether to give 1-[2,4-dichloro-beta-(4-thiazolylmethoxy) phenethyl]imidazole hydrochloride (1.7 g, 46%) m.p. 183-184. (Found: C, 46.3; H, 3.7; N, 10.7. C15 H13 N3 Cl2 OS.HCl requires C, 46.1; H, 3.6; N, 10.7%).

Reference： [1]Patent: US4062966,1977,A

66
[ 24155-42-8 ]
[ 46503-49-5 ]

Yield	Reaction Conditions	Operation in experiment
74.3%	With thionyl chloride; at 20℃; for 12h;	General procedure: Intermediate 10a (25.7 g, 0.1 mol) was added to the solution ofthionyl chloride (59.5 g, 0.5 mol). The mixture was stirred at 20 C for 12 h. Then, the solution was added to the mixture of ice andwater (300 g). The pH value of the mixture was adjusted to neutralwith potassium hydroxide. The white solid was obtained by filtrationand recrystallization (EtOH). Yield 74.3%, HRMS m/z:275.9833.0217 [M+Na]+. According to the preparation method of11a, 10b was used as raw material to prepare the intermediate 11b:white solid, Yield 73.6%, HRMS m/z: 243.0504 [M+H]+.
	With thionyl chloride; In dichloromethane;	EXAMPLE 18 This example demonstrates the preparation of the optical isomers of 1-[2,4-dichloro-beta-(4'-chlorobenzylthio)phenethyl]-imidazole nitrate. Distilled thionyl chloride (0.5 ml.) is added dropwise to a solution of 0.27 g. of (+)-1-(2,4-dichloro-beta-hydroxyphenethyl)-imidazole[alphaD25 =+99 (c=1, methanol), see U.S. Pat. No. 3,839,574] in 50 ml. of dichloromethane at 0 C. After stirring for 2 hours, the solvent is removed in vacuo. The resultant residue, a pale yellow gum, is dissolved in 50 ml. of dichloromethane, and the solution neutralized with dilute potassium carbonate solution, dried over magnesium sulfate and evaporated to yield 0.29 g. of 1-(2,4-dichloro-beta-chlorophenethyl)imidazole.

Reference： [1]European Journal of Medicinal Chemistry,2020,vol. 198
[2]Patent: US4055652,1977,A

67
[ 288-32-4 ]
[ 13692-14-3 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,1,1,3',3',3'-hexafluoro-propanol; alumina-supported potassium hydroxide; at 45℃; for 3.5h;	with mechanical stirring,1500g of HFIP was recovered from the 500mL four-port reaction bottle of the reflux condenser.KOH/A12O3 38g, recovered imidazole 18.7g,1-(2,4-dichlorophenyl)-2-chloro-ethanol 44.7 g,Heating and heating to 45 C for 3.5 h,The reaction was followed by TLC, filtered to obtain filter cake I and filtrate I. The filter cake I was rinsed with recovered HFIP to obtain the washing liquid I and the filter cake II, and the filtrate 1 and the washing liquid 1 were combined for rotary evaporation to control the rotation speed of 70 r/min, vacuum. Degree -0.09 ~ -0.1MPa, water temperature 40 ~ 50 C to no distillate outflow, add 10% dilute hydrochloric acid 13g (36% hydrochloric acid 3.6g mixed with water 9.4g) adjust the pH to 7, add water 350g, stir for 10min , filtered, to obtain filter cake III and filtrate II, filter cake III is added to the machine with mechanical stirring, reflux condenserIn a 250mL four-neck reaction flask, add 65g of absolute ethanol, stir, heat until the crude imidazole ethanol is completely dissolved, add 0.5g of activated carbon after a little cold, reflux for 10min, heat filter, naturally reduce to room temperature, then cool down in ice water. 3 C, filtration, drying at 60 C, to obtain imidazole ethanol, named sample IV;
78.7%	With potassium carbonate;sodium iodide; In water; butanone;	(b) An alternative method for the preparation of 1-(2',4'dichlorophenyl)2-(1H-imidazole)-1-ethanol follows. Four g (17.74 mmol) of (+-)-2-chloro-(2',4'dichlorophenyl)-1-ethanol, prepared by sodium borohydride reduction of 2,2',4'-trichloroacetophenone (purchased from Aldrich Chemical), and 5.00 g (73.44 mmol) of imidazole were dissolved in 15 mL of dry 2-butanone in a 100 mL round bottom flask equipped with a magnetic stirrer bar and reflux condenser. Four g K2CO3 and a catalytic amount of NaI were added and the solution was refluxed under a nitrogen atmosphere for 36 hours. After cooling to room temperature, the reaction mixture was filtered. Ether was added to the filtrate and the resulting solution was washed with 50 mL of water and the layers separated. The aqueous layer was extracted 3 times with 50 mL portions of ether. The ether extracts were combined with the previous organic phase and the total dried over anhydrous MgSO4. After filtration to remove MgSO4, the filtrate was concentrated to give a yellowish oil. Chromatography of the crude product (CH2Cl2:CH3OH/95:5) provided 3.59 g of purified pale yellow crystals (78.7% yield). 1-(beta-Allyloxy-beta-2',4'-dichlorophenylethyl)imidazole (Imazalil):
	With sodium; In N-methyl-acetamide; methanol; water;	EXAMPLE B 1-(2',4'-dichlorophenyl)-2-(N-imidazolyl)-ethanol 30 g of sodium were added to a solution of 88.5 g of imidazole in 600 ml of methanol; the solvent was then evaporated off. The residue was dissolved in 300 ml of dimethylformamide and heated to 115-120 C. To the solution so obtained was added, dropwise and under stirring, a solution of 225 g of 1-(2',4'-dichlorophenyl)-2-chloro-ethanol in 400 ml of dimethylformamide. The mixture was heated to 115-120 C. and maintained at that temperature for 20 minutes and, after subsequent cooling to 40 C., 2500 ml of iced water were added under vigorous stirring. The product precipitated under stirring over a period of about two hours, the upper liquid was then decanted off, a further 2500 ml of water were added and, after standing, the whole was filtered. The precipitate thus obtained was dried and crystallized from toluene. 170 g of the desired product, melting at 134-135 C., was obtained.

Reference： [1]Patent: CN109111402,2019,A .Location in patent: Paragraph 0030; 0033; 0035; 0037; 0039; 0041; 0043; 0045
[2]Patent: US6207695,2001,B1
[3]Patent: US4221803,1980,A

68
3-chloromethyl-4,6-dichloroquinoline [ No CAS ]
[ 56-93-9 ]
[ 7440-44-0 ]
[ 24155-42-8 ]
[ 78107-85-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; ethereal hydrochloric acid; In tetrahydrofuran; water;	(d) 4,6-Dichloro-3-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:1) In a three necked flask, fitted with stirrer, reflux condenser and gas inlet tube are introduced 14.8 g. of sodium hydroxide (0.37 mol.) and 25 ml. of water. While passing nitrogen through the flask, the solution is cooled to 45 and then are added 3.85 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.015 mol.), [prepared according to J. Med. Chem., Vol. 12, 784 (1969)], 0.25 g. of benzyltrimethylammonium chloride and 25 ml. of tetrahydrofuran. To the mixture, which is warmed to 50, a solution of 3.6 g. of 3-chloromethyl-4,6-dichloroquinoline (0.015 mol.) in 10 ml. of tetrahydrofuran is added from a prewarmed dropping funnel within 3 minutes. The mixture is stirred vigorously for 3 hours at 60 using a water bath. Then the warm mixture is transferred into a separating funnel, the lower aqueous sodium hydroxide is extracted with 10 ml. of tetrahydrofuran. The combined tetrahydrofuran layers are dried by means of sodium sulfate, and after the solvent has been removed, the residual oil is extracted with ether, treated with charcoal and filtered. To the solution of free base are added dropwise ethereal hydrochloric acid. The precipitated 4,6-dichloro-3-[[1-(2,4-dichlorophenyl-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride is filtered off, dried in the vacuum desiccator and recrystallized from absolute ethanol; yield: 1.9 g. (25%); m.p. 148-150.

Reference： [1]Patent: US4202985,1980,A

69
3-chloromethyl-4,7-dichloroquinoline [ No CAS ]
[ 24155-42-8 ]
[ 78126-05-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ethereal hydrochloric acid; In tetrahydrofuran; water; mineral oil;	(d) 4,7-Dichloro-3-[[1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy]methyl]quinoline, hydrochloride (1:2) 5.2 g. of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (0.02 mol.) dissolved in 45 ml. of anhydrous tetrahydrofuran and 0.8 g. of sodium hydride (55-60% dispersion in mineral oil) are stirred for 4.5 hours at room temperature. After the sodium salt formation is complete, 4.9 g. of 3-chloromethyl-4,7-dichloroquinoline (0.02 mol.) dissolved in 25 ml. of anhydrous tetrahydrofuran are added and the mixture is stirred at 50-60 (bath temperature) for 4 hours. Then tetrahydrofuran is removed, the residue treated with water and extracted with ether. The ethereal layer is washed with water and dried with sodium sulfate. Addition of ethereal hydrochloric acid to the ether solution of the base precipitates the hydrochloride salt. For purification the hydrochloride is converted into the free base and again extracted and treated with ethereal hydrochloric acid.

Reference： [1]Patent: US4202985,1980,A

70
[ 24155-42-8 ]
[ 27646-28-2 ]
[ 27656-21-9 ]

Reference： [1]Chirality,2010,vol. 22,p. 69 - 76

71
[ 108-24-7 ]
[ 24155-42-8 ]
[ 61258-54-6 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 2115 - 2122

72
[ 939-99-1 ]
[ 24155-42-8 ]
C₁₉H₁₅Cl₂F₃N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		10.30g of compound 1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl)ethanol was suspended in 26 mL of acetone, then 31 mL of a 50% solution of sodium hydroxide in water was added, followed by more than 26 mL of acetone, keeping the entire reaction mixture on intense agitation. Then 0.45 g of triethyl ammonium benzyl chloride was added, keeping the reaction mixture under reflux for thirty minutes. Still under reflux 8.2 g of 1-(chloromethyl)-4-(trifluoromethyl)benzene compound (diluted in 13 mL of acetone) were added, maintaining the agitation and reflux for 6 hours. At the end, the heterogeneous mixture was filtered and the phases separated. The organic phase was rotoevaporated at 45 C to dryness. The obtained residue was dissolved in 100 mL of cold ethyl ether. It was then added 2 mL of nitric acid (65%) at 0 C, maintaining the agitation for one hour. At the end the product was filtered and washed with cold ethanol and dried at 65 C for 12 hours. The product obtained as a white colored solid (compound BL123) had the following characteristics: NMR 1H(300 MHz-DMSO): 9.05 (1H, s), 7.72-7.74 (1H, m), 7.65-7.66 (4H, m), 7.53-7.54 (1H, m), 7.38-7.45 (3H, m), 5.51-5.20 (1H, m) 4.45-4.64 (4H, m). NMR 13C (75MHz-DMSO): 142.1, 136.3, 134.1, 133.6, 133.3, 129.5, 129.2, 128.5, 128.1, 127.9, 125, 2, 125.1, 123,, 119.8, 75.4, 69.7, 51.8; Elementary Analysis calc. for C19H16Cl 2O4 F3N3: C=47.72%, H=3.37%, N=8.79%; obtained: C=48.06%, H=3.44%, N=8.76%.Metting point: 173-176 C.

Reference： [1]Patent: EP2471781,2012,A1 .Location in patent: Page/Page column 11

73
5-(4'-(bromomethyl)biphenyl-3-yl)-1-trityl-1H-tetrazole [ No CAS ]
[ 24155-42-8 ]
C₄₄H₃₄Cl₂N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A 3-way flask equipped with mechanical agitation and reflux condenser was charged with THF (120 mL) and NaH 60% (24 g). To this suspension a solution of 1-(2,4-dichlorophenyl)-2-(1H-imidazole-1-yl) ethanol [1] (0.233 mmol, 60 g in 600 mL of THF) was slowly added and the resulting solution was left under mechanical stirring for 30 min. After this period, the reaction mixture was cooled in an ice bath and to it a solution of 5-(4'-(bromomethyl) biphenyl-3-a)-1-Trityl-1H-tetrazole [2] (0.223 mmol ; 129 g in 650 mL of THF) was slowly added. The addition process being completed, the ice bath was removed and the reaction was brought to reflux for 4 hours. After this period, the reaction mixture was cooled to room temperature and to it 560 mL of water were slowly added. This reaction mixture was extracted with 600 mL of ethyl acetate. The organic phase was separated and extracted with a 5% citric acid (2 x 420 mL) aqueous solution. The aqueous phases were combined and extracted with ethyl acetate (2x 300 mL). The organic phases were combined, dried with MgSO4. The solvent was rotoevaporated and an orange oil was isolated.

Reference： [1]Patent: EP2471781,2012,A1 .Location in patent: Page/Page column 12

74
[ 2631-72-3 ]
[ 24155-42-8 ]

Reference： [1]Polyhedron,2013,vol. 52,p. 106 - 114
[2]European Journal of Medicinal Chemistry,2014,vol. 84,p. 284 - 301
[3]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 1665 - 1674

75
[ 67035-78-3 ]
[ 13692-14-3 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
68%	In acetonitrile;Reflux;	General procedure: Asolution of halohydrins (1.0 equiv.) and ionic liquid 7 (1.0 equiv.)in anhydrous MeCN was refluxed for 10-12 h. The reaction hasbeen monitored by TLC. A 3=4 volume of solvent was removed undervacuum, the residue poured into water and extracted with ethylacetate. The organic phase was dried over anhydrous Na2SO4, distilledoff. The obtained crude product was precipitated in acetone as a white solid. Yield 68% from 11. Yield 40% from 12. M.p. 142-143 C. IR (KBr, cm 1): 1512 (m), 1079 (s), 845 (s), 733 (m). 1HNMR (DMSO-d6, ppm): d = 4.0-4.06 (m, 2 H, 2CH2), 5.06-5.08 (m,1 H, 1CH), 4.16 (d, J = 10.8 Hz, 1 H, OH), 6.03 (d, J = 4 Hz, 1 H, 4CHof the imidazole ring), 6.83 (d, J = 4 Hz, 1 H, 5CH of the imidazolering), 7.03 (s, 1 H, 2CH), 7.42-7.46 (m, 2 H, 5CH, 6CH). 7.59 (s, 1H, 3CH). 13C NMR (DMSO-d6, ppm): d = 137.14 (6C), 136.20 (1C),132.99 (10C), 130.11 (7C), 130.01 (2C), 129.68 (8C), 128.04 (11C),126.12 (9C), 118.44 (3C) 63.88 (5C); 53.22 (4C). Anal. Calc. for C11-H10Cl2N2O (257.12): C, 51.38; H, 3.92; N, 10.89; Found C, 51.39;H, 3.92; N, 10.90%.

Reference： [1]Polyhedron,2013,vol. 52,p. 106 - 114

76
[ 67035-78-3 ]
[ 53066-15-2 ]
[ 24155-42-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	In acetonitrile;Reflux;	General procedure: Asolution of halohydrins (1.0 equiv.) and ionic liquid 7 (1.0 equiv.)in anhydrous MeCN was refluxed for 10-12 h. The reaction hasbeen monitored by TLC. A 3=4 volume of solvent was removed undervacuum, the residue poured into water and extracted with ethylacetate. The organic phase was dried over anhydrous Na2SO4, distilledoff. The obtained crude product was precipitated in acetone as a white solid. Yield 68% from 11. Yield 40% from 12. M.p. 142-143 C. IR (KBr, cm 1): 1512 (m), 1079 (s), 845 (s), 733 (m). 1HNMR (DMSO-d6, ppm): d = 4.0-4.06 (m, 2 H, 2CH2), 5.06-5.08 (m,1 H, 1CH), 4.16 (d, J = 10.8 Hz, 1 H, OH), 6.03 (d, J = 4 Hz, 1 H, 4CHof the imidazole ring), 6.83 (d, J = 4 Hz, 1 H, 5CH of the imidazolering), 7.03 (s, 1 H, 2CH), 7.42-7.46 (m, 2 H, 5CH, 6CH). 7.59 (s, 1H, 3CH). 13C NMR (DMSO-d6, ppm): d = 137.14 (6C), 136.20 (1C),132.99 (10C), 130.11 (7C), 130.01 (2C), 129.68 (8C), 128.04 (11C),126.12 (9C), 118.44 (3C) 63.88 (5C); 53.22 (4C). Anal. Calc. for C11-H10Cl2N2O (257.12): C, 51.38; H, 3.92; N, 10.89; Found C, 51.39;H, 3.92; N, 10.90%.

Reference： [1]Polyhedron,2013,vol. 52,p. 106 - 114

77
[ 24155-42-8 ]
[ 1429399-73-4 ]

Reference： [1]Polyhedron,2013,vol. 52,p. 106 - 114

78
[ 24155-42-8 ]
[ 27523-40-6 ]

Reference： [1]Polyhedron,2013,vol. 52,p. 106 - 114

79
[ 2014-83-7 ]
[ 24155-42-8 ]
isoconazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%		To a suspension of 60% dispersion of NaHin mineral oil (0.25 g, 7.5 mmol) in dry 1,4-dioxane (15 mL) atroom temperature under a nitrogen atmosphere was added dropwisea solution of 13 (1.28 g, 5 mmol) in 1,4-dioxane (20 mL).The reaction mixture was refluxed for 1 h. 1,3-Dichloro-2-(chloromethyl)benzene 14 (1 g, 5 mmol) was added dropwise and refluxedfor 2.5 h. Solvent was removed in vacuum, and after thatthe reaction was quenched with water (100 mL). The aqueous solutionwas extracted with ethyl acetate (3x50 mL), the organicphases were combined, dried over anhydrous Na2SO4, and filtered.The solvent was removed by distillation under reduced pressure,giving a crude reaction mixture that was purified followed by crystallizationfrom acetone to give 1.45 g of ester 10. Yield: 70%. M.p.115-116 C.A solution of base 10 (1.2 g, 2.8 mmol) in acetone (5 mL) wastreated with concentrated (86%) HNO3 (5 mL) followed by stirringfor 12 h. The white solid 15 was filtered and dried over P2O5 in vacuumdesiccator. Yield 1.35 g, 98%. M.p. 203-204 C. IR (KBr, cm 1):1381 (w), 1380 (w), 1510 (m), 1150 (m), 810 (s), 720 (s). 1H NMR(DMSO-d6, ppm): d = 4.40-4.50 (m, 2 H, 1CH), 4.62 (d, J = 10.8 Hz, 2H, -OCH2), 5.12-5.20 (m, 1 H, 2CH), 7.30-7.42 (m, 3 H, phenyl of 2-(2,6-dichlorobenzyloxy)), 7.48-7.59 (m, 2 H, 5CH, 6CH), 7.60 (s, 2 H,4CH, 5CH of the imidazole ring), 7.72 (s, 1 H, 3CH) 9.04 (s, 1 H, 2CHof the imidazole ring), 14.6 (s, 1 H, HNO3). 13C NMR (DMSO-d6,ppm): d = 138.10 (1C), 137.79 (13C), 135.35 (6C), 133.12 (14C, 7C),131.88 (10C), 131.22 (2C), 130.00 (16C), 129.41 (7C), 128.21 (8C),128.16 (15C, 18C) 127.13 (11C), 125.18 (9C), 118.29 (3C), 74.31(5C), 71.80 (12C), 50.99 (4C). Anal. Calc. for C18H15Cl4N3O4(479.14): C, 45.12; H, 3.16; N, 8.77; Found C, 45.40; H, 3.15%.

Reference： [1]Polyhedron,2013,vol. 52,p. 106 - 114

80
[ 24155-42-8 ]
[ 74-88-4 ]
1-(2-(2,4-dichlorophenyl)-2-methoxyethyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%		A suspension of sodium hydride (1.5mmol, 1.5eq) in DMF (5mL) was treated with a solution of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (5, 1mmol, 1eq) in DMF (5mL) at 0C. The resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1.5h. The mixture was cooled to 0C and methyliodide (1mmol, 1eq) was added. The resulting mixture was stirred for 1h at room temperature. The reaction was quenched by addition of water (15mL). The aqueous phase was extracted with ethyl acetate (15mL, three times), the organic was washed with water (15mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography (SiO2, MeOH/ethyl acetate) afforded 6a as an oil in 60% yield. 1H NMR (400MHz, CDCl3): delta 7.48-7.42 (m, 2H), 7.30-7.21 (m, 2H), 7.03 (bs, 1H), 6.92 (s, 1H), 4.78 (dd, 1H, J=7.0, J=2.6Hz), 4.21-4.16 (m, 1H), 4.04-3.97 (m, 1H), 3.25 (s, 3H) ppm.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 84,p. 284 - 301

81
[ 69966-55-8 ]
[ 24155-42-8 ]
[ 1621686-35-8 ]

Yield	Reaction Conditions	Operation in experiment
62%		General procedure: A suspension of sodium hydride (1.5mmol, 1.5eq) in DMF (5mL) was treated with a solution of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethanol (5, 1mmol, 1eq) in DMF (5mL) at 0C. The resulting mixture was stirred under a nitrogen atmosphere at room temperature for 1.5h. The mixture was cooled to 0C and methyliodide (1mmol, 1eq) was added. The resulting mixture was stirred for 1h at room temperature. The reaction was quenched by addition of water (15mL). The aqueous phase was extracted with ethyl acetate (15mL, three times), the organic was washed with water (15mL), dried over Na2SO4 and the solvent was removed in vacuo. Purification by column chromatography (SiO2, MeOH/ethyl acetate) afforded 6a as an oil in 60% yield.

Reference： [1]European Journal of Medicinal Chemistry,2014,vol. 84,p. 284 - 301

82
[ 64728-23-0 ]
[ 24155-42-8 ]
1-(2-(2,4-dichlorophenyl)-2-(3,4-dimethoxyphenethoxy)ethyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		To a solution of alcohol 3 (0.257 g, 1.0 mmol) in anhydrous DMF (3.0 mL) was added NaH (2.0 mmol, 0.048 g, 60% in mineral oil) atroom temperature under nitrogen atmosphere, and the reactionmixture was stirred for 20 min. Then, alkyl halide 4 (0.292 g,1.0 mmol) dissolved in 2 mL of anhydrous DMF was added dropwiseand the reaction mixture was stirred for 24 h at room temperature,at which time TLC indicated the disappearance of thestarting materials. Brine (~40 mL) was added to the reactionmixture, which was washed with EtOAc (3 10 mL). The organiclayer was dried(anhydrous Na2SO4) and the solvent evaporatedunder reduced pressure. Flash column chromatographyafforded the yellow oil 8 (0.282 g, 67%). Rf: 0.77 (EtOAc/Hex 3/7). 1HNMR: (300 MHz, CDCl3) d 7.72 (d, J 1.7 Hz, 1H, N]CHeN),7.57e7.55 (m, 3H), 7.21e6.96 (m, 5H), 5.20 (t, J 3.54 Hz, 1H,CHeO), 4.27 (dd, J 3.1, 13.9 Hz, 1H, CHeO), 4.12 (dd, J 7.0,13.9 Hz, 1H, CH2eN), 3.90 (s, 3H, OCH3), 3.87 (s, 3H, OCH3), 3.45 (s,2H, CH2), 2.62 (t, J 1.8 Hz, 2H, CH2) ppm. 13C NMR: (75.4 MHz,CDCl3) d 148.8 (C), 147.4 (C), 139.7 (C), 137.6 (C), 136.3 (C), 135.7(C), 133.8 (C), 131.8 (C), 130.6 (C), 128.7 (C), 127.4 (C), 122.6 (C), 119.3(C), 111.6 (C), 111.0 (C), 75.0 (CHeO), 69.3 (CH2eO), 55.8 (CH2eN),53.4 (OCH3), 52.7 (OCH3), 36.3 (CH2) ppm. MS [EI] m/z (%): 420(M), 256 (23), 223 (94), 222 (85), 203 (19), 176 (81), 147 (93), 112(96), 91 (58), 84 (100), 63 (43), 51 (90), 41 (59).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 97,p. 275 - 279

83
[ 2417-72-3 ]
[ 24155-42-8 ]
methyl 4-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: To a solution of alcohol 3 (0.257 g, 1.0 mmol) in anhydrous DMF (3.0 mL) was added NaH (2.0 mmol, 0.048 g, 60% in mineral oil) atroom temperature under nitrogen atmosphere, and the reactionmixture was stirred for 20 min. Then, alkyl halide 4 (0.292 g,1.0 mmol) dissolved in 2 mL of anhydrous DMF was added dropwiseand the reaction mixture was stirred for 24 h at room temperature,at which time TLC indicated the disappearance of thestarting materials. Brine (~40 mL) was added to the reactionmixture, which was washed with EtOAc (3 10 mL). The organiclayer was dried(anhydrous Na2SO4) and the solvent evaporatedunder reduced pressure. Flash column chromatographyafforded the yellow oil 8 (0.282 g, 67%).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 97,p. 275 - 279

84
[ 71831-21-5 ]
[ 24155-42-8 ]
(4-((1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)methyl)phenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%		General procedure: To a solution of alcohol 3 (0.257 g, 1.0 mmol) in anhydrous DMF (3.0 mL) was added NaH (2.0 mmol, 0.048 g, 60percent in mineral oil) atroom temperature under nitrogen atmosphere, and the reactionmixture was stirred for 20 min. Then, alkyl halide 4 (0.292 g,1.0 mmol) dissolved in 2 mL of anhydrous DMF was added dropwiseand the reaction mixture was stirred for 24 h at room temperature,at which time TLC indicated the disappearance of thestarting materials. Brine (~40 mL) was added to the reactionmixture, which was washed with EtOAc (3 10 mL). The organiclayer was dried over (anhydrous Na2SO4) and the solvent evaporatedunder reduced pressure. Flash column chromatographyafforded the yellow oil 8 (0.282 g, 67percent).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 97,p. 275 - 279

85
[ 29270-30-2 ]
[ 24155-42-8 ]
2-(2-chlorophenyl)-2-(1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)ethoxy)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%		General procedure: To a solution of alcohol 3 (0.257 g, 1.0 mmol) in anhydrous DMF (3.0 mL) was added NaH (2.0 mmol, 0.048 g, 60% in mineral oil) atroom temperature under nitrogen atmosphere, and the reactionmixture was stirred for 20 min. Then, alkyl halide 4 (0.292 g,1.0 mmol) dissolved in 2 mL of anhydrous DMF was added dropwiseand the reaction mixture was stirred for 24 h at room temperature,at which time TLC indicated the disappearance of thestarting materials. Brine (~40 mL) was added to the reactionmixture, which was washed with EtOAc (3 10 mL). The organiclayer was dried(anhydrous Na2SO4) and the solvent evaporatedunder reduced pressure. Flash column chromatographyafforded the yellow oil 8 (0.282 g, 67%).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 97,p. 275 - 279

86
[ 1208-87-3 ]
[ 24155-42-8 ]
α-(2,4-dichlorophenyl)-β,N-imidazolylethyl 4-phenylthiobezyl ether nitrate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.1%		710 g of sodium hydroxide, 511.2 g of 1- (2,4-dichlorophenyl) -2-imidazole ethanol, 1136 ml of water, 5680 ml of toluene and 56.8 g of tetrabutylammonium bromide were placed in a room temperature (25 ° C.) 10L reaction flask, stirring was warmed to 58 ° C, a solution of <strong>[1208-87-3]4-phenylmercaptobenzyl chloride</strong> in toluene (554.1g ? 1130ml) was added dropwise over 1.5 hours. Reaction at 60 ° C 12hour,The layers were separated and the aqueous layer was discarded. The organic layer was washed with saturated aqueous sodium chloride solution three times (250 ml × 1 + 200 ml × 2), washed twice with water (200 ml × 2), dried over anhydrous magnesium sulfate, filtered and the filtrate was reduced in pressure , Temperature 55 ° C) was concentrated to dryness and toluene was recovered to obtain 1250.5 g of an oil. 5680 ml of a mixed solution (ethyl acetate: toluene = 1: 1) was added followed by 1136 ml of a 20percent nitric acid ethyl acetate solution and stirred at 25 ° C 3 hours, filtered, washed, the filter cake was collected, dried under atmospheric pressure at 40 ° C to give a light yellow solid 738g. Yield 71.4percent, HPLC pureDegree: 99.84percent.Into a 5000 ml reaction flask, 2800 ml of anhydrous ethanol, 340 ml of water, and 738 g of crude nitetazole were injected, and the temperature was raised to 60° C. to completely dissolve the solution. The solution was naturally cooled to 25° C., crystallized for 12 hours, filtered, and the filter cake was washed with a little ethyl acetate. , Drying under atmospheric pressure at 45°C gave 628 g of a white solid. Yield: 85.1percent, purity HPLC: 99.97percent.
82.1%		In 1000ml of three necked flask equipped with a stirrer, thermometer, dropping funnel added 25.6g of 1-(2,4-dichlorophenyl)-2-imidazol-ethanol (0.1mol) , 120ml tetrahydrofuran, 40ml water, 6g (0. 15mol) of sodium hydroxide ,1.2g PEG-400 and slowly warmed to reflux. While stirring added drop wise 4-Phenylthio-benzylchloride 30g (0. 12 mol 95percent), completion of the addition in approximately 30min and stirring at constant temperature for 4h,then the reaction was cooled, added 400ml of Diethyl ether, separatedaqueous layer, then aqueous layer was extracted with diethyl ether (200ml X2), combined the organic layer, washed with water , dried over anhydrous sodiumsulfate, filtrate , at the room temperature in filtrate liquid slowy & dropwise added 10ml concentrated nitric acid, precipitate solid, suction filtered,washed with diethyl ether, recrystallized using 95percent of ethanol to obtain white solid 37.3g, yield 82.1percent. mp 136-138oC.
74.7%		At room temperature (25 °C) Sodium hydroxide, 1- (2,4-dichlorophenyl) -2-imidazol ethanol, water, toluene, tetrabutylammonium bromide administered into the reaction flask, heated with stirring to 58 °C 4-phenyl benzyl benzyl chloride in toluene was added dropwise, and the addition was completed in 1.5 h. Insulation reaction 12h, layers were separated aqueous layer was discarded, and the organic layer was washed with a saturated aqueous sodium chloride solution, washed with water, the toluene layer was dried over anhydrous magnesium sulfate, filtered and the filtrate under reduced pressure (pressure of 1330 Pa, a temperature of 55 °C) and concentrated to dryness recovered toluene to give an oil, was added a mixed solvent (ethyl acetate: toluene = 1: 1), added 20percent nitric acid in ethyl acetate solution at room temperature (25 °C) was stirred for 3h crystallization, filtration, water washing, collecting The filter cake was dried under normal pressure at 40 °C to give a pale yellow solid

71.4%

710 g of sodium hydroxide, 511.2 g of 1-(2,4-dichlorophenyl)-2-imidazoleethanol, 1136 ml of water, 5680 ml of toluene and 56.8 of tetrabutylammonium bromide at room temperature (25 °C). g, put into a 10L reaction bottle, stir and heat to 58 °C,A toluene solution of 4-phenylhydrazinobenzyl chloride (554.1 g - 1130 ml) was added dropwise, and the dropwise addition was completed over 1.5 hours. The reaction was carried out at 60 °C for 12 hours, the layers were separated, the aqueous layer was discarded, and the organic layer was washed three times with a saturated aqueous solution of sodium chloride (250 ml X 1 + 200 ml Chi 2).The mixture was washed twice with water (200 ml X 2 ), dried over anhydrous magnesium sulfate, filtered, and the filtrate was evaporated to dryness under reduced pressure (1330 Pa, temperature 55 °C) to yield toluene to give an oil of 1250.5 g. Toluene = 1:1) 5680ml, Further, and then 20percent of nitric acid was added 1136 ml of anethyl ester solution was stirred at 25 °C for 3 hours, filtered, washed with water, and the filter cake was collected and dried at 40 °C to give 738 g of pale yellow solid. The yield was 71.4percent, and the HPLC purity was 99.84percent.

Reference： [1]Patent: CN107573288,2018,A .Location in patent: Paragraph 0017; 0025; 0026
[2]Patent: CN102180835,2016,B .Location in patent: Paragraph 0012; 0017; 0018
[3]Patent: CN107652238,2018,A .Location in patent: Paragraph 0028
[4]Patent: CN109096197,2018,A .Location in patent: Paragraph 0036; 0049; 0050; 0051

87
2,4-dichlorobenzyl methanesulfonate [ No CAS ]
[ 24155-42-8 ]
[ 22916-47-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 4288 - 4294

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 24155-42-8 ]

Aryls

[ 67085-11-4 ]

4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol

Similarity: 0.81

[ 41570-61-0 ]

2-(tert-Butylamino)-1-(2-chlorophenyl)ethanol

Similarity: 0.71

[ 1220033-11-3 ]

3-((2,4-Dichlorobenzyl)oxy)pyrrolidine hydrochloride

Similarity: 0.61

[ 1475-13-4 ]

1-(2,4-Dichlorophenyl)ethanol

Similarity: 0.59

[ 59767-13-4 ]

1-(2-(1-(4-Chlorophenyl)-1-phenylethoxy)ethyl)azepane hydrochloride

Similarity: 0.58

Chlorides

[ 67085-11-4 ]

4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol

Similarity: 0.81

[ 41570-61-0 ]

2-(tert-Butylamino)-1-(2-chlorophenyl)ethanol

Similarity: 0.71

[ 1220033-11-3 ]

3-((2,4-Dichlorobenzyl)oxy)pyrrolidine hydrochloride

Similarity: 0.61

[ 1475-13-4 ]

1-(2,4-Dichlorophenyl)ethanol

Similarity: 0.59

[ 59767-13-4 ]

1-(2-(1-(4-Chlorophenyl)-1-phenylethoxy)ethyl)azepane hydrochloride

Similarity: 0.58

Alcohols

[ 67085-11-4 ]

4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol

Similarity: 0.81

[ 41570-61-0 ]

2-(tert-Butylamino)-1-(2-chlorophenyl)ethanol

Similarity: 0.71

[ 1475-13-4 ]

1-(2,4-Dichlorophenyl)ethanol

Similarity: 0.59

[ 39512-49-7 ]

4-(4-Chlorophenyl)piperidin-4-ol

Similarity: 0.58

[ 120466-66-2 ]

(R)-1-(2-Chlorophenyl)ethanol

Similarity: 0.58

Related Parent Nucleus of
[ 24155-42-8 ]

Imidazoles

[ 67085-11-4 ]

4-(4-Chlorophenyl)-1-(1H-imidazol-1-yl)butan-2-ol

Similarity: 0.81

[ 883543-82-6 ]

2-((1H-Imidazol-1-yl)methyl)benzoic acid

Similarity: 0.58

[ 67914-69-6 ]

rel-Ethyl 4-(4-(((2R,4S)-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine-1-carboxylate

Similarity: 0.58

[ 78712-43-3 ]

(E)-3-(4-((1H-Imidazol-1-yl)methyl)phenyl)acrylic acid hydrochloride

Similarity: 0.57

[ 78892-28-1 ]

(2,6-Dimethylphenyl)(1H-imidazol-4-yl)methanol

Similarity: 0.57

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 24155-42-8 ] {[proInfo.proName]}

Quality Control of [ 24155-42-8 ]

Related Doc. of [ 24155-42-8 ]

Product Details of [ 24155-42-8 ]

Calculated chemistry of [ 24155-42-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 24155-42-8 ]

Application In Synthesis of [ 24155-42-8 ]

[ 24155-42-8 ] Synthesis Path-Upstream 1~12

[ 24155-42-8 ] Synthesis Path-Downstream 1~87

Related Functional Groups of [ 24155-42-8 ]

Aryls

Chlorides

Alcohols

Related Parent Nucleus of [ 24155-42-8 ]

Imidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 24155-42-8 ]

Related Parent Nucleus of
[ 24155-42-8 ]