[ CAS No. 930-62-1 ] {[proInfo.proName]}

Name: 930-62-1|2,4-Dimethylimidazole|96%
Brand: Ambeed
SKU: A416867
Price: 5.0 USD
Availability: InStock
Rating: 92 (40 reviews)

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

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Limited Quantity	USD 15-60
Inaccessible (Haz class 6.1), Domestic	USD 80+
Inaccessible (Haz class 6.1), International	USD 150+
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Quality Control of [ 930-62-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 930-62-1 ]

SDS Specification

Alternatived Products of [ 930-62-1 ]

Product Details of [ 930-62-1 ]

CAS No. :	930-62-1	MDL No. :	MFCD00022365
Formula :	C₅H₈N₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LLPKQRMDOFYSGZ-UHFFFAOYSA-N
M.W :	96.13	Pubchem ID :	70259
Synonyms :

Calculated chemistry of [ 930-62-1 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.4
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	28.52
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.11
Log Po/w (XLOGP3) :	0.86
Log Po/w (WLOGP) :	1.03
Log Po/w (MLOGP) :	-0.06
Log Po/w (SILICOS-IT) :	1.87
Consensus Log Po/w :	0.96

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.51
Solubility :	3.0 mg/ml ; 0.0312 mol/l
Class :	Very soluble
Log S (Ali) :	-1.05
Solubility :	8.65 mg/ml ; 0.09 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.92
Solubility :	1.15 mg/ml ; 0.0119 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.27

Safety of [ 930-62-1 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P261-P280-P305+P351+P338-P310	UN#:	3263
Hazard Statements:	H302-H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 930-62-1 ]

* 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 [ 930-62-1 ]
Downstream synthetic route of [ 930-62-1 ]

[ 930-62-1 ] Synthesis Path-Upstream 1~22

1
[ 52726-31-5 ]
[ 930-62-1 ]

Yield	Reaction Conditions	Operation in experiment
16%	With triethylsilane; palladium 10% on activated carbon In tetrahydrofuran at 20℃; for 24 h; Inert atmosphere	General procedure: A 16 mL vial with a PTFE/silicone septum and a nitrogen-bubbler line was charged with N-benzylbenzimidazole (208.1 mg, 1.0 mmol), Pd/C (10 wt percent, dry powder, reduced) (20 mg) and THF (5 mL). The mixture was treated at rt with triethylsilane (320 µL, 2.0 mmol) and then stirred under nitrogen for 14 h at rt. The mixture was filtered through a 0.45 µM PTFE syringe filter and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (0 to 10percent MeOH/ dichloromethane) to afford benzimidazole as a colorless solid (117.6 mg, 0.996 mmol 99percent). The reactions generally exhibit an induction period of 5 to 30 min as indicated by the initiation of gas release (i.e., bubbling) from the reaction mixture. The use of Pd/C on a dry matrix is imperative as wet Pd/C results in decreased yield or no reaction.

Reference： [1] Tetrahedron Letters, 2015, vol. 56, # 21, p. 2688 - 2690

2
[ 64-19-7 ]
[ 78-90-0 ]
[ 930-62-1 ]
[ 930-62-1 ]

Reference： [1] Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.), 1992, vol. 41, # 4, p. 728 - 734[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1992, # 4, p. 932 - 940

3
[ 96-26-4 ]
[ 75-07-0 ]
[ 930-62-1 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1929, vol. 183, p. 71

4
[ 75-07-0 ]
[ 78-98-8 ]
[ 930-62-1 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1929, vol. 183, p. 71

5
[ 6014-42-2 ]
[ 930-62-1 ]

Reference： [1] Chemische Berichte, 1907, vol. 40, p. 801
[2] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1914, vol. 92, p. 279,281

6
[ 6014-42-2 ]
[ 822-36-6 ]
[ 930-62-1 ]

Reference： [1] Chemische Berichte, 1907, vol. 40, p. 801

7
[ 66675-19-2 ]
[ 108-24-7 ]
[ 930-62-1 ]

Reference： [1] Chemische Berichte, 1922, vol. 55, p. 3708

8
[ 50-99-7 ]
[ 75-07-0 ]
[ 930-62-1 ]

Reference： [1] Chemische Berichte, 1906, vol. 39, p. 3887

9
[ 50-99-7 ]
[ 75-07-0 ]
[ 930-62-1 ]

Reference： [1] Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1929, vol. 183, p. 71

10
[ 592-20-1 ]
[ 75-07-0 ]
[ 930-62-1 ]

Reference： [1] Chemische Berichte, 1935, vol. 68, p. 1953,1956

11
[ 930-61-0 ]
[ 67-66-3 ]
[ 5053-43-0 ]
[ 95-58-9 ]
[ 693-98-1 ]
[ 930-62-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

12
[ 6338-45-0 ]
[ 10447-93-5 ]
[ 930-62-1 ]

Reference： [1] Journal of the Chemical Society, 1903, vol. 83, p. 469
[2] Journal of the Chemical Society, 1910, vol. 97, p. 1820
[3] Chemische Berichte, 1906, vol. 39, p. 3889

13
[ 930-61-0 ]
[ 67-66-3 ]
[ 5053-43-0 ]
[ 4994-86-9 ]
[ 693-98-1 ]
[ 930-62-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

14
[ 930-61-0 ]
[ 67-66-3 ]
[ 4994-86-9 ]
[ 693-98-1 ]
[ 930-62-1 ]
[ 75712-73-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

15
[ 930-61-0 ]
[ 67-66-3 ]
[ 5053-43-0 ]
[ 4994-86-9 ]
[ 693-98-1 ]
[ 930-62-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

16
[ 930-61-0 ]
[ 67-66-3 ]
[ 4994-86-9 ]
[ 693-98-1 ]
[ 930-62-1 ]
[ 75712-73-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1431 - 1435

17
[ 930-61-0 ]
[ 67-66-3 ]
[ 5053-43-0 ]
[ 95-58-9 ]
[ 693-98-1 ]
[ 930-62-1 ]

18
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 75712-74-2 ]
[ 75712-73-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

19
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 38557-72-1 ]
[ 75712-73-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

20
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 75712-74-2 ]
[ 75712-73-1 ]

21
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 38557-72-1 ]
[ 75712-73-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

22
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 38557-72-1 ]
[ 75712-73-1 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1980, p. 1427 - 1430

[ 930-62-1 ] Synthesis Path-Downstream 1~88

1
[ 930-62-1 ]
[ 74-88-4 ]
1,2,3,4-tetramethylimidazolium iodide [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 185,195; dtsch. Ref. S. 256, 259, 260
Chem.Abstr.,1939,p. 4988
[2]Chemistry of Materials,2015,vol. 27,p. 3756 - 3762

2
[ 6014-42-2 ]
[ 822-36-6 ]
[ 930-62-1 ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 801

3
[ 6014-42-2 ]
[ 930-62-1 ]

Reference： [1]Chemische Berichte,1907,vol. 40,p. 801

4
[ 930-61-0 ]
[ 67-66-3 ]
[ 5053-43-0 ]
[ 4994-86-9 ]
[ 693-98-1 ]
[ 930-62-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1431 - 1435

5
[ 930-61-0 ]
[ 67-66-3 ]
[ 5053-43-0 ]
[ 95-58-9 ]
[ 693-98-1 ]
[ 930-62-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1431 - 1435
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 1431 - 1435

6
[ 930-61-0 ]
[ 67-66-3 ]
[ 4994-86-9 ]
[ 693-98-1 ]
[ 930-62-1 ]
[ 75712-73-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1431 - 1435

7
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 38557-72-1 ]
[ 75712-73-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1427 - 1430

8
[ 930-62-1 ]
[ 67-66-3 ]
[ 4472-45-1 ]
[ 95-89-6 ]
[ 75712-74-2 ]
[ 75712-73-1 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 1427 - 1430
[2]Journal of the Chemical Society. Perkin transactions I,1980,p. 1427 - 1430

9
[ 930-62-1 ]
[ 2314-97-8 ]
[ 81769-62-2 ]

Reference： [1]Journal of Organic Chemistry,1982,vol. 47,p. 2867 - 2872

10
[ 930-62-1 ]
[ 446-33-3 ]
[ 102792-10-9 ]
2,5-Dimethyl-1-(3-methyl-4-nitro-phenyl)-1H-imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

11
[ 930-62-1 ]
[ 1635-61-6 ]
[ 131885-68-2 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463

12
[ 930-62-1 ]
[ 7149-80-6 ]
[ 131885-59-1 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463

13
[ 930-62-1 ]
[ 393-09-9 ]
[ 102792-15-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

14
[ 930-62-1 ]
[ 85733-62-6 ]
[ 129057-05-2 ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 2314 - 2327

15
[ 930-62-1 ]
[ 131885-36-4 ]
[ 131885-56-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463

16
[ 930-62-1 ]
[ 75-36-5 ]
[ 52757-00-3 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform; toluene;	EXAMPLE 42 1-Acetyl-2,4-dimethylimidazole A solution of 9.6 g (0.10 M) of 2,4-dimethylimidazole in 50 ml of chloroform and 50 ml of toluene was stirred at room temperature and 3.6 ml (0.05 M) of acetyl chloride was added via syringe over 1 minute. The mixture was stirred at room temperature for 2 hours, then the mixture was filtered to remove insoluble solids, and the filtrate concentrated leaving 6.9 g (100%) of 1-acetyl-2,4-dimethylimidazole as a white crystalline solid: nmr (CDCl3) (delta): 7.00 (s, 1H); 2.68 (s, 3H); 2.57 (s, 3H); 2.21 (s, 3H).
	In chloroform; toluene; at 20℃; for 2h;	Intermediate 2: Step a 1-(2,4-Dimethyl-imidazol-1-yl)-ethanone The title compound was prepared according to the procedure described in J. Org. Chem. 1983, 48, 897: To a solution of 2,4-dimethylimidazole (4.00 g, 41.6 mmol) in toluene/chloroform (1/1, v/v, 50 mL) at room temperature was added acetyl chloride (1.48 mL, 20.8 mmol) dropwise over several minutes. The reaction was stirred at room temperature for 2 hours and filtered. The filtrate was evaporated, ethyl acetate was added and the solution was filtered again. The filtrate was evaporated to give the title compound.
	In chloroform; ethyl acetate; toluene;	Intermediate 18: step a 1-(2,4-Dimethyl-imidazol-1-yl)-ethanone The title compound was prepared according to the procedure described in J. Org. Chem. 1983, 48, 897: To a solution of 2,4-dimethylimidazole (4.00 g, 41.6 mmol) in toluene/chloroform (1/1, v/v, 50 mL) at room temperature was added acetyl chloride (1.48 mL, 20.8 mmol) dropwise over several minutes. The reaction was stirred at room temperature for 2 hours and filtered. The filtrate was evaporated, ethyl acetate was added and the solution was filtered again. The filtrate was evaporated to give the title compound.

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 897 - 898
[2]Patent: US4374843,1983,A
[3]Patent: US2012/129897,2012,A1 .Location in patent: Page/Page column 18
[4]Patent: US2012/302573,2012,A1

17
[ 930-62-1 ]
[ 350-46-9 ]
[ 23309-18-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

18
[ 930-62-1 ]
[ 108857-30-3 ]
[ 108857-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;	Preparation 14 Ethyl N-trifluoroacetyl-N-(2-nitro-5-[2,4-dimethylimidazol-1-yl]benzyl)glycinate STR36 A mixture of 2,4-dimethylimidazole (6.25 g), ethyl N-trifluoroacetyl-N-(5-fluoro-2-nitrobenzyl)glycinate (22.0 g) and sodium carbonate (6.62 g) was stirred and heated at 130 for 2 hours. Volatile material was removed from the cooled mixture in vacuo and the residue was partitioned between ethyl acetate (200 cm3) and water (100 cm3). The organic phase was washed with water (2*25 cm3), dried (MgSO4), and evaporated in vacuo to give an oil which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluding with ethyl acetate:methanol, 1:19. Combination and evaporation of the appropriate fractions gave an oil which crystallized on trituration with ether to afford the title compound, m.p. 172.5-176 (3.1 g). Analysis %: Found: C,50.7; H,4.8; N,12.7; Calculated for C18 H19 F3 N4 O5: C,50.5; H,4.5; N,13.1.

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2042 - 2049
[2]Patent: US4783467,1988,A

19
[ 930-62-1 ]
[ 1615-53-8 ]
[ 85868-83-3 ]

Reference： [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1982,vol. 21,p. 945 - 948

20
[ 930-62-1 ]
[ 433-27-2 ]
1-(2,5-Dimethyl-3H-imidazol-4-yl)-2,2,2-trifluoro-ethanol [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1986,vol. 32,p. 329 - 344

21
[ 64-19-7 ]
[ 78-90-0 ]
[ 930-62-1 ]
[ 930-62-1 ]

Reference： [1]Bull. Russ. Acad. Sci. Div. Chem. Sci. (Engl. Transl.),1992,vol. 41,p. 728 - 734
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1992,p. 932 - 940

22
[ 930-62-1 ]
[ 300552-87-8 ]
[ 474100-17-9 ]

Reference： [1]Journal of Medicinal Chemistry,2002,vol. 45,p. 4398 - 4401

23
[ 912969-57-4 ]
[ 930-62-1 ]
[4-(2,4-dimethyl-imidazol-1-yl)-thiazol-2-yl]-<i>p</i>-tolyl-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776

24
[ 912969-55-2 ]
[ 930-62-1 ]
(4-bromo-phenyl)-[4-(2,4-dimethyl-imidazol-1-yl)-thiazol-2-yl]-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776

25
[ 912969-58-5 ]
[ 930-62-1 ]
(3-bromo-phenyl)-[4-(2,4-dimethyl-imidazol-1-yl)-thiazol-2-yl]-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776

26
[ 912969-59-6 ]
[ 930-62-1 ]
[4-(2,4-dimethyl-imidazol-1-yl)-thiazol-2-yl]-(3-methoxy-phenyl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776

27
[ 912969-56-3 ]
[ 930-62-1 ]
[4-(2,4-dimethyl-imidazol-1-yl)-thiazol-2-yl]-(4-methoxy-phenyl)-amine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5769 - 5776

28
[ 870694-43-2 ]
[ 930-62-1 ]
1-(5-bromopyridin-2-yl)-2-(2,4-dimethyl-1H-imidazol-1-yl)ethanone [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4868 - 4881

29
[ 930-62-1 ]
[ 76-83-5 ]
[ 23593-69-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With triethylamine; In dichloromethane; at 20℃;	Intermediate 27: 2,4-Dimethyl-1-trityl-1H-imidazole; A solution of trityl chloride (15 g, 55 mmol) in dichloromethane (50 mL) was added drop wise over 45 minutes to a solution of 2,4-dimethyl imidazole (5 g, 52 mmol) in a mixture of dichloromethane (100 mL) and triethylamine (11.3 mL, 81 mmol) at room temperature. The mixture was stirred over night, then quenched with methanol (4 mL) and stirred for additional 30 minutes. The solvent was evaporated, the residue taken up in toluene (600 mL), washed with potassium phosphate buffer (pH 7, 1M, 2x 200 mL) and with water (200 mL). The organic phase was diluted with dichloromethane (200 mL), dried over sodium sulfate, and concentrated under reduced pressure to -100 mL. Hexanes (100 mL) were added and the precipitated was collected by filtration and washed with hexanes (2x 50 mL) to give 14.76 g (84 %) of the product as a colourless solid. ¹H-NMR (CDCl3) 5: 1.62 (s, 3H); 2.16 (s, 3H); 6.40 (s, 2H); 7.10-7.40 (m, 15H).
84%	With triethylamine; In dichloromethane; at 20℃;	Intermediate 25: 2,4-Dimethyl-1-trityl-1H-imidazole; A solution of trityl chloride (15 g, 55 mmol) in dichloromethane (50 mL) was added drop wise over 45 minutes to a solution of 2,4-dimethyl imidazole (5 g, 52 mmol) in a mixture of dichloromethane (100 mL) and triethylamine (11.3 mL, 81 mmol) at room temperature. The mixture was stirred over night, then quenched with methanol (4 mL) and stirred for additional 30 minutes. The solvent was evaporated, the residue taken up in toluene (600 mL), washed with potassium phosphate buffer (pH 7, 1M, 2x 200 mL) and with water (200 mL). The organic phase was diluted with dichloromethane (200 mL), dried over sodium sulfate, and concentrated under reduced pressure to -100 mL. Hexanes (100 mL) were added and the precipitated was collected by filtration and washed with hexanes (2x 50 mL) to give 14.76 g (84 %) of the product as a colourless solid. (at)H-NMR (CDCl3) 8: 1.62 (s, 3H) ; 2.16 (s, 3H) ; 6.40 (s, 2H) ; 7.10-7.40 (m, 15H).

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 4868 - 4881
[2]Patent: WO2005/116022,2005,A1 .Location in patent: Page/Page column 64
[3]Patent: WO2005/116023,2005,A1 .Location in patent: Page/Page column 63-64

30
[ 930-62-1 ]
C₁₃H₂₃N₂O₃⁽¹⁺⁾*(CF₃SO₂)2N^(1-) [ No CAS ]

Reference： [1]Tetrahedron Letters,2004,vol. 45,p. 9455 - 9459

31
[ 930-62-1 ]
[ 102791-91-3 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

32
[ 930-62-1 ]
[ 118111-98-1 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

33
[ 930-62-1 ]
[ 102791-45-7 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

34
[ 930-62-1 ]
[ 102791-55-9 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

35
[ 930-62-1 ]
[ 102791-47-9 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

36
[ 930-62-1 ]
[ 102792-18-7 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

37
[ 930-62-1 ]
[ 118111-94-7 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

38
[ 930-62-1 ]
[ 118111-93-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

39
[ 930-62-1 ]
[ 102791-97-9 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

40
[ 930-62-1 ]
[ 102792-24-5 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

41
[ 930-62-1 ]
[ 118111-97-0 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

42
[ 930-62-1 ]
[ 102792-17-6 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

43
[ 930-62-1 ]
[ 108857-19-8 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2042 - 2049

44
[ 930-62-1 ]
[ 102792-29-0 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

45
[ 930-62-1 ]
[ 108857-11-0 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2042 - 2049

46
[ 930-62-1 ]
(E)-N-[4-(2,4-Dimethyl-imidazol-1-yl)-2-trifluoromethyl-phenyl]-3-ethoxy-acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

47
[ 930-62-1 ]
[ 108857-32-5 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 2042 - 2049

48
[ 930-62-1 ]
[ 102792-03-0 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

49
[ 930-62-1 ]
[ 108857-39-2 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

50
[ 930-62-1 ]
[ 108857-38-1 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

51
[ 930-62-1 ]
[ 102791-84-4 ]

Reference： [1]Journal of Medicinal Chemistry,1989,vol. 32,p. 575 - 583

52
[ 930-62-1 ]
[ 131886-03-8 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463

53
[ 930-62-1 ]
5-(2,4-Dimethyl-imidazol-1-yl)-7-methyl-2-pyridin-4-yl-1H-benzoimidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 4455 - 4463

54
[ 930-62-1 ]
[ 56536-44-8 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 897 - 898
[2]Patent: US2012/129897,2012,A1
[3]Patent: US2012/302573,2012,A1

55
[ 930-62-1 ]
1,3,4-trimethyl-2-<i>trans</i>(?)-styryl-imidazolium; iodide [ No CAS ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1939,vol. 59,p. 185,195; dtsch. Ref. S. 256, 259, 260
Chem.Abstr.,1939,p. 4988

56
[ 930-62-1 ]
[ 221164-86-9 ]
[ 221164-94-9 ]

Yield	Reaction Conditions	Operation in experiment
		1H-NMR(CDCl3,delta):1.47(3H,t,J=7.3 Hz),1.53(3H,t,J=7.3 Hz), 2.24(6H,s),4.23(3H,s),4.56(2H,q,J=7.3 Hz),4.66(2H,q,J=7.3 Hz), 6.66(1H,s),8.10(1H,s),8.44(1H,s).

Reference： [1]Patent: US6348461,2002,B1 .Location in patent: Page column 86

57
[ 930-62-1 ]
[ 1735-54-2 ]
[ 677704-68-6 ]

Reference： [1]Patent: WO2004/29038,2004,A1 .Location in patent: Page 37

58
[ 930-62-1 ]
[ 367-67-9 ]
C₁₂H₁₀F₃N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 120℃; for 36h;	A mixture of 2-bromo-5-nitrobenzotrifuoride (Lancaster Synthesis, GmbH; 6.0 g, 22 [MMOL)] and 2, 4-dimethylimidazole (10.6, 110 [MMOL)] is heated at [120C] for 36 hours under an argon atmosphere. The mixture is then cooled and the residue is treated with water (150 mL) and extracted with ethyl acetate (3 x 80 mL). The combined extracts are washed (brine), dried (MgSO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography (silica gel, eluent ethyl acetate) to afford 1- [[4-NITRO-2- (TRIFLUOROMETHYL) PHENYL]-1 H-IMIDAZOLE] as yellow crystalline solid. This product is dissolved in ethanol (290 mL) and hydrogenated at atmospheric pressure over Raney nickel (1. 15 g) at [25C.] The calculated amount of hydrogen is taken up in 14 hours. The mixture is then filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by recrystallisation from ether-hexane to give the title compound as a crystalline solid, m. p. [163-164C.]

Reference： [1]Patent: WO2004/5281,2004,A1 .Location in patent: Page 57

59
[ 930-62-1 ]
[ 89-75-8 ]
[ 309283-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 5.33333h;Heating / reflux;	1. Preparation of 1-(2,4-dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one. A solution of 2,4-dichlorobenzoyl chloride (7.24 M) in dichloromethane (25 ml) was added dropwise over 20 minutes to a stirred solution of 2,4-dimethylimidazole (0.80 M) in dichloromethane (75 ml) and N,N-diisopropylethylamine (Huenig's base) (34 ml). The reaction mixture was cooled during the addition using a water bath. The reaction mixture was then heated to reflux for 5 hours. The reaction can turn a darker color. The product was stripped of solvent under reduced pressure, and the resulting solid was dried in vacuo for one hour. To the dry solid (described above) was added a solution (2:1 v/v, 120 ml) of gla. acetic acid and aq. con. HCl. The mixture was then stirred at reflux for ca. 90 min. The acetic acid was removed via rotary evaporator. Upon cooling, distilled water (200 ml) and toluene (100 ml) were added to the solid residue, which was vigorously stirred for 30 min. The solids were filtered, rinsed with 50 ml distilled water, and discarded. The filtrate was transferred to a separatory funnel. After the organic layer was discarded, the aqueous layer was washed with toluene (2×100 ml). The aqueous layer was transferred to a large beaker (2 L) and diluted with isopropyl ether (50 ml). The stirred mixture was basified (pH 7-8) by careful addition of sodium bicarbonate which leads to the formation of a sticky white solid. Dichloromethane (200 ml) was added and stirring continued for 10 min. The organic layer was separated and the aqueous layer was again extracted with dichloromethane (100 ml). The organic layers were combined and washed with sat. aq. NaHCO3 (100 ml), distilled water (100 ml), brine (100 ml), dried with Na2SO4, filtered, concentrated, and dried in vacuo giving 1-(2,4-dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one in 46% yield.

Reference： [1]Patent: US2005/54663,2005,A1 .Location in patent: Page/Page column 19

60
[ 930-62-1 ]
[ 141699-59-4 ]
4-(2,4-dimethyl-imidazol-1-yl)-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6%	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 100℃; for 72h;	A suspension of 2,4-dimethylimidazole (5.16 g), tert-butyl 4-[(methylsulfonyl)oxy]piperidine-1-carboxylate (10 g) and potassium carbonate (4.95 g) in DMF (80 mL) was stirred at 100C for 72 hours. The reaction mixture was concentrated under reduced pressure. The residue was diluted with water and ethyl acetate. An organic layer was separated, washed with saturated sodium hydrogencarbonate, and then dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure. The residue was purified with a silica gel column (dichloromethane/methanol/aqueous ammonia = 100/3.5/0.5 to 100/10/1) to obtain the title compound (0.58 g, 6%) as a yellow oil. NMR (300 MHz, CDCl3) delta: 1.43 (9H, s), 1.66-1.92 (3H, m), 2.16 (3H, s), 2.37 (3H, s), 2.77-2.85 (2H, m), 3.79-3.91 (2H, m), 4.26 (2H, m), 6.55 (1H, s).

Reference： [1]Patent: EP1564213,2005,A1 .Location in patent: Page/Page column 31

61
[ 930-62-1 ]
[ 631897-38-6 ]

Yield	Reaction Conditions	Operation in experiment
74%	With N-iodo-succinimide; In acetonitrile; at 80℃; for 16h;	Compound 5.5. 5-Iodo-2,4-dimethyl-lH-imidazole. NIS (14. Og, 62.4mmol) was added portion-wise to a solution of 2,4-dimethyl-lH-imidazole (5.00 g, 52.0 mmol) in acetonitrile (100 mL). The mixture was heated at 80 C for 16 hours, then cooled to room temperature. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (300 mL) and water (80 mL). The organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL), dried (MgS04) and concentrated under reduced pressure. The residue was purified with by silica gel column chromatography (hexanes:EtOAc 1 : 1 to 10% MeOH in EtOAc) to yield the title compound as a light yellow solid (8.56 g, 74%). m/z (ES+) 223(M+H)+. NMR (400 MHz, CDC13) delta 9.69 (br s, 1H),
74%	With N-iodo-succinimide; In acetonitrile; at 80℃; for 16h;	Compound 5.5. 5-Iodo-2,4-dimethyl-lH-imidazole. NIS (14.0g, 62.4mmol) was added portion-wise to a solution of 2,4-dimethyl- lH-imidazole (5.00 g, 52.0 mmol) in acetonitrile (100 mL). The mixture was heated at 80 C for 16 hours, then cooled to room temperature. The solvent was removed under reduced pressure and the residue was partitioned between EtOAc (300 mL) and water (80 mL). The organic layer was washed with saturated sodium thiosulfate (50 mL), brine (50 mL), dried (MgS04) and concentrated under reduced pressure. The residue was purified with by silica gel column chromatography (hexanes:EtOAc 1 : 1 to 10% MeOH in EtOAc) to yield the title compound as a light yellow solid (8.56 g, 74%). m/z (ES+) 223(M+H)+. NMR (400 MHz, CDC13) delta 9.69 (br s, 1H), 2.38 (s, 3H), 2.19 (s, 3H)
44%	With N-iodo-succinimide; In acetonitrile; for 16h;Heating / reflux;	Example B; 5-Iodo-2,4-dimethyl-1H-imidazole; In this example of the compound XIX, R2 is methyl, R4 is methyl, and X is chloro. Nevertheless it is understood that the person skilled in the art would be able to prepare other compounds of formula XIX, wherein R2 and R(at) are other than methyl, and X is other than chloro, using the method used for in the following example:; <strong>[930-62-1]2,4-Dimethylimidazole</strong> (5.0g, 52 mmol) was suspended in 100 ml Acetonitrile and N- Iodosuccinimide (14.0g, 62.4 mmol) was added. The reaction mixture was stirred at reflux for 16 hours, then evaporated and decolorized with sat NaHS03- solution. Water was added and extracted two times with 100 ml ethyl acetate. The organic layers were washed with Brine, dried with sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel (dichloromethane/methanol 9:1). The desired product was obtained as a light brown solid (5.10 g, 44%), MS: m/e = 223.0 (M+H+).

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 72
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 86; 87
[3]Patent: WO2005/118568,2005,A1 .Location in patent: Page/Page column 39-40

62
[ 930-62-1 ]
[ 89-75-8 ]
[ 252953-85-8 ]

Yield	Reaction Conditions	Operation in experiment
46%	With sodium hydrogencarbonate; In dichloromethane; water; toluene;	1. Preparation of 1-(2,4-dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one. A solution of 2,4-dichlorobenzoyl chloride (7.24 M) in dichloromethane (25 ml) was added dropwise over 20 minutes to a stirred solution of 2,4-dimethylimidazole (0.80 M) in dichloromethane (75 ml) and N,N-diisopropylethylamine (Huenig's base) (34 ml). The reaction mixture was cooled during the addition using a water bath. The reaction mixture was then heated to reflux for 5 hours. The reaction can turn a darker color. The product was stripped of solvent under reduced pressure, and the resulting solid was dried in vacuo for one hour. To the dry solid (described above) was added a solution (2:1 v/v, 120 ml) of gla. acetic acid and aq. con. HCl. The mixture was then stirred at reflux for ca. 90 min. The acetic acid was removed via rotary evaporator. Upon cooling, distilled water (200 ml) and toluene (100 ml) were added to the solid residue, which was vigorously stirred for 30 min. The solids were filtered, rinsed with 50 ml distilled water, and discarded. The filtrate was transferred to a separatory funnel. After the organic layer was discarded, the aqueous layer was washed with toluene (2*100 ml). The aqueous layer was transferred to a large beaker (2 L) and diluted with isopropyl ether (50 ml). The stirred mixture was basified (pH 7-8) by careful addition of sodium bicarbonate which leads to the formation of a sticky white solid. Dichloromethane (200 ml) was added and stirring continued for 10 min. The organic layer was separated and the aqueous layer was again extracted with dichloromethane (100 ml). The organic layers were combined and washed with sat. aq. NaHCO3 (100 ml), distilled water (100 ml), brine (100 ml), dried with Na2SO4, filtered, concentrated, and dried in vacuo giving 1-(2,4-dichlorophenyl)-2-(4-methylimidazol -2-yl)ethan-1-one in 46% yield.

Reference： [1]Patent: US2002/156087,2002,A1

63
[ 930-62-1 ]
[ 540-51-2 ]
[ 3716-08-3 ]
[ 3715-99-9 ]

Yield	Reaction Conditions	Operation in experiment
29%	With hydrogenchloride; In N,N-dimethyl-formamide; mineral oil;	The starting material was prepared as follows: <strong>[930-62-1]2,4-Dimethylimidazole</strong> (1.5 g, 15.6 mmol) was added in portions to a suspension of sodium hydride (936 mg of a 60% suspension in mineral oil, 23 mmol) in DMF (8 ml) and the mixture was stirred for 30 minutes at ambient temperature. 2-Bromoethanol (1.66 ml, 23 mmol) was added and the mixture stirred at 100 C. for 16 hours. The solvent was removed by evaporation and concentrated hydrochloric acid (1 ml) was added to the residue. The resulting solid was triturated with methylene chloride, collected by filtration and dried under vacuum. The solid was purified by column chromatography on neutral alumina eluding with methylene chloride/methanol (97/3) and then column chromatography eluding with methylene chloride/methanol (93/7 followed by 90/10) to give a 75/25 mixture of 2-(2,4-dimethylimidazol-1-yl)ethanol and 2-(2,5-dimethylimidazol-1-yl)ethanol (650 mg, 29%). MS-ESI: 140 [MH]+

Reference： [1]Patent: US5962458,1999,A

64
[ 5460-29-7 ]
[ 930-62-1 ]
N-[3-(2,4-dimethylimidazol-1-yl)propyl]phthalimide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide;	1) In a similar manner to Example A, a mixture of 2,4-dimethylimidazole (24.0 g) was added to a suspension of sodium hydride (10.0 g, 60% dispersion) in DMF (300 ml). After stirring for. 1.5 hours, DMF (80 ml) was added followed by a slurry of N-(3-bromopropyl)phthalimide (63.8 g) in DMF (100 ml). The mixture was reacted and worked up as in Example A and the residue triturated with petroleum ether b.p. 60-80 C. and then with ether. The residue was recrystallized from ethyl acetate to give N-[3-(2,4-dimethylimidazol-1-yl)propyl]phthalimide, m.p. 191-122 C. 1 H nmr indicated the presence of approximately 10% of N-[3-(2,5-dimethylimidazol-1-yl)propyl]phthalimide.

Reference： [1]Patent: US5547972,1996,A

65
[ 930-62-1 ]
[ 35375-74-7 ]
8-(2,4-Dimethyl-1H-imidazol-1-yl)-7-trifluoromethyl[1,2,4]triazolo[4,3-a]quinoxaline-1,4(2H,5H)-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		a. 8-(2,4-Dimethyl-1H-imidazol-1-yl)-7-trifluoromethyl[1,2,4]triazolo-[4,3-a]quinoxaline-1,4(2H,5H)-dione The title compound was prepared from 4-amino-2-chloro-5-nitrobenzotrifluoride and 2,4-dimethylimidazole by a method analogous to the method described in example 4. M.p.>330 C. 1 H-NMR (DMSO-d6): delta2.02 (s, 3H), 2.11 (s, 3H), 6.91 (s, 1H), 7.69 (s, 1H), 8.44 (s, 1H), 12.15 (br.s, 1H), 13.15 (br. s, 1H). MS (m/e): 364 (M+, 100%).

Reference： [1]Patent: US5532236,1996,A

66
[ 930-62-1 ]
[ 7732-18-5 ]
[ 49780-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; sulfuric acid; nitric acid; urea;	A. Sulfuric acid (30 ml, 0.56 mole) was added dropwise to 2,4-dimethylimidazole (10 g, 0.104 mole), and urea (6.24 g, 0.104 mole), in a 1 l. flask cooled in ice. This was followed by the addition of fuming nitric acid (30 ml, 0.72 mole). When all had been added, the flask was heated at 200 C. for 1-2 minutes, whereupon a vigorous reaction ensued, necessitating the removal of the heat. When the reaction subsided, heating is continued for 10 minutes. The flask was then allowed to cool, and the reaction mixture was added to 300 ml of H2 O. The solution was adjusted to pH 5 with aqueous sodium hydroxide (about 40 g of sodium hydroxide was required). The resulting precipitate was filtered off and dried in vacuum to give 9.9 g of 2,4-dimethyl-5-nitroimidazole.

Reference： [1]Patent: US4678799,1987,A

67
[ 930-62-1 ]
[ 446-33-3 ]
[ 102792-10-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In N-methyl-acetamide;	PREPARATION 39 1-(3-Methyl-4-nitrophenyl)-2,4-dimethylimidazole STR118 A mixture of 5-fluoro-2-nitrotoluene (10.3 g), 2,4-dimethylimidazole (6.36 g) and sodium carbonate (7.5 g) was heated with stirring in dimethylformamide (40 cm3) at 130 for 40 hours. The cooled mixture was then concentrated in vacuo, the residue was acidified to pH1 with 4M hydrochloric acid, and the resulting solution was extracted with chloroform (225 cm3) to remove any neutral material. The combined aqueous phases were basified to pH10 with 2.5M sodium hydroxide solution and the mixture was extracted with chloroform (3250 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluding with methanol:ethyl acetate, 1:19. Combination and evaporation of appropriate fractions afforded a solid (8.4 g) which was recrystallized from ethyl acetate to give 1-(3-methyl-4-nitrophenyl)-2,4-dimethylimidazole, m.p. 135.5-138. Analysis %: Found: C, 62.0; H, 5.7; N, 17.9; Calculated for C12 H13 N3 O2: C, 62.3; H, 5.7; N, 18.2.
	With sodium carbonate; In N-methyl-acetamide;	Preparation 38 1-(3-Methyl-4-nitrophenyl)-2,4-dimethylimidazole STR53 A mixture of 3-fluoro-6-nitrotoluene (10.3 g), 2,4-dimethyl-imidazole (6.36 g) and sodium carbonate (7.5 g) was heated with stirring in dimethylformamide (40 cm3) at 130 for 40 hours. The cooled mixture was then concentrated in vacuo, the residue was acidified to pH1 with 4M hydrochloric acid, and the resulting solution was extracted with chloroform (225 cm3) to remove any neutral material. The combined aqueous phases were basified to pH10 with 2.5M sodium hydroxide solution and the mixture was extracted with chloroform (3250 cm3). The combined and dried (MgSO4) organic extracts were concentrated in vacuo to give a solid which was chromatogrpahed on silica (Merck "MK 60.9385" [Trade Mark]) eluding with methanol:ethyl acetate, 1:19. Combination and evaporation of appropriate fractions afforded a solid (8.4 g) which was recrystallized from ethyl acetate to give 1-(3-methyl-4-nitrophenyl)-2,4-dimethylimidazole, m.p. 135.5-138. Analysis %: Found: C,62.0; H,5.7; N,17.9; Calculated for C12 H13 N3 O2: C,62.3; H,5.7; N,18.2.

Reference： [1]Patent: US4728653,1988,A
[2]Patent: US4783467,1988,A

68
[ 50-00-0 ]
[ 930-62-1 ]
[ 108-94-1 ]
[ 942588-31-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; at 75℃; for 10h;	The mixture of 2,4-dimethylimidazole (9.61 g, 0.1 mol), cyclohexanone (20.7 ml, 0.2 mol), paraformaldehyde (3.2 g, 0.107 mol) and acetic acid (40 ml) was heated at 75 0C for 10 hours. The obtained solution was concentrated in vacuo. To the residue water (25 ml) and dichloromethane (150 ml) was added, and the pH was adjusted to 10 with aqueous sodium hydroxide solution. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. The crude residue was purified by column chromatography on silica gel (Kieselgel 60, eluent: chloroform : methanol = 9:1) to obtain the title compound (4.1 g) (MS: M+= 208.3).Applying the above procedure the following compounds were prepared: e.g. 2- (piperidin-l-ylmethyl)-cyclohexanone, 2-(imidazol-l-ylmethyl)-cyclopentanone, 2- (morpholin-4-ylmethyl)-cyclohexanone.

Reference： [1]Patent: WO2007/72089,2007,A1 .Location in patent: Page/Page column 21

69
[ 930-62-1 ]
[ 870-24-6 ]
[ 279237-85-3 ]
[ 279236-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetrabutylammonium sulfate; In acetonitrile; for 48h;Heating / reflux;	PREPARATIVE EXAMPLE 51. A mixture of 2-chloroethylamine hydrochloride (7.66 g, 66 mmol), 2,4- dimethylimidazole (5.88 g, 61 mmol), tetrabutyl ammonium sulfate (0.83 g, 2.5 mmol), solid NaOH (8.81 g, 220 mmol) and anhydrous acetonitrile (80 mL) Is stirred at reflux for 48 h under N2- The mixture is filtered, concentrated in vacuo and purified by flash column chromatography (silica gel) using 2% MeOH-CH2Cl2 saturated with aqueous ammonium hydroxide to give the title compound.

Reference： [1]Patent: WO2007/84498,2007,A1 .Location in patent: Page/Page column 189

70
[ 930-62-1 ]
[ 60121-78-0 ]
1-[4-(4-chloro-phenyl)-piperazin-1-yl]-2-(2,4-dimethyl-imidazol-1-yl)-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium sulfate; In Ki; N,N-dimethyl-formamide;	Synthesis of 1-[4-(4-Chloro-phenyl)-piperazin-1-yl]-2-(2,4-dimethyl-imidazol-1-yl)-ethanone 2,4-dimethylimidazole (0.633 g, 0.7 mmol) was taken up in dry DMF (15 mL) and dry potassium carbonate (340 mg) and KI (20 mg) was added and the reaction mixture was stirred at room temperature for 1 h under nitrogen. 2-Chloro-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone (200 mg, 1.1 mmol) in DMF (5 mL) was then added to the mixture through a syringe. The reaction was then heated at 140 C. for 14 h, cooled and quenched with water and extracted with ethyl acetate. Drying of the organic layer with Na2SO4 followed by concentration gave material that was purified on a silica gel column (CHCl3/MeOH) delta 1H NMR (300 MHz, CDCl3) delta 7.25 (d, 2H), 6.80 (d, 2H), 6.53 (s, 1H), 4.62 (s, 2H), 3.78 (br, 2H), 3.59 (br, 2H), 3.21 (br, 4H), 2.31 (s, 3H), 2.17 (s, 1H).
		[0327] 2,4-dimethylimidazole (0.633g, 0.7mmol) was taken up in dry DMF (15ml) and dry potassium carbonate (340mg) and KI (20mg) was added and the reaction mixture was stirred at room temperature for 1h under nitrogen. 2-Chloro-1-[4-(4-chloro-phenyl)-piperazin-1-yl]-ethanone (200mg, 1.1 MMOL)] in DMF (5ml) was then added to the mixture through a syringe. The reaction was then heated at 140C for 14h, cooled and quenched with water and extracted with ethyl acetate. Drying of the organic layer with [NA2S04] followed by concentration gave material that was purified on a silica gel column (CHCl3/MeOH) :1H NMR (300 MHz, CDCl3) : delta 7.25 (d, 2H), 6.80 (d, 2H), 6.53 (s, 1H), 4.62 (s, 2H), 3.78 (br, 2H), 3.59 (br, 2H), 3.21 (br, 4H), 2.31 (s, 3H), 2.17 (s, 1H).

Reference： [1]Patent: US2004/162282,2004,A1
[2]Patent: WO2003/105853,2003,A1 .Location in patent: Page 134

71
[ 930-62-1 ]
[ 13820-81-0 ]
[ 7550-35-8 ]
pentamminecobalt(III)(2,4-dimethyl-3H-imidazole)*2H₂O [ No CAS ]

Reference： [1]Journal of the Chemical Society, Dalton Transactions,1991,p. 3031 - 3042

72
[ 930-62-1 ]
[(η(5)-pentamethylcyclopentadienyl)RuCl]4 [ No CAS ]
potassium hydride [ No CAS ]
[ 318245-89-5 ]

Reference： [1]Organometallics,2000,vol. 19,p. 5263 - 5265

73
[ 930-62-1 ]
[(η(5)-pentamethylcyclopentadienyl)RuCl]4 [ No CAS ]
potassium hydride [ No CAS ]
[ 318245-89-5 ]
[(2,4-dimethylimidazolato)Ru(C₅Me₅)]3 [ No CAS ]

Reference： [1]Organometallics,2000,vol. 19,p. 5263 - 5265

74
[ 930-62-1 ]
Re₄H₄*12CO=(ReH(CO)3)4 [ No CAS ]
[H₄Re₃(CO)9(2,4-dimethylimidazole)](-)[2,4-dimethylimidazolium](+) [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1995,vol. 490,p. 111 - 116

75
[ 930-62-1 ]
[ 7646-78-8 ]
[ 195719-85-8 ]

Reference： [1]Russian Journal of Coordination Chemistry,1997,vol. 23,p. 543 - 549

76
[ 930-62-1 ]
tin(ll) chloride [ No CAS ]
[ 195719-80-3 ]

Reference： [1]Russian Journal of Coordination Chemistry,1997,vol. 23,p. 543 - 549

77
iron(III) protoporphyrin IX dimethyl ester chloride [ No CAS ]
[ 930-62-1 ]
[Fe(protoporphyrin IX dimethylester)(2,4-dimethylimidazole)2]Cl [ No CAS ]

Reference： [1]Inorganica Chimica Acta,1979,vol. 36,p. L421

78
[ 930-62-1 ]
[ 870-24-6 ]
[ 279237-85-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In acetonitrile; for 24h;Heating / reflux;	Synthesis of 2-imidazol-1 -yl-ethylamine derivatives by lambda/-alkylation of disubstituted imidazoles [general procedure (GP9)]Sodium hydroxide (180 mmol; powder) and tetrabutylammonium hydrogensulfate (1.80 mmol) were successively added to a solution of the respective imidazole derivative (45.00 mmol) in MeCN (100 ml). After 30 min., 2-chloroethylamine hydrochloride (54.00 mmol) <n="74"/>was added and the reaction mixture was stirred for 24h at reflux. The obtained suspension was filtered and the filtrate was concentrated in vacuo to give a crude oil which was used without further purification.2-(2,4-dimethyl-imidazol-1-yl)-ethylamine Prepared by lambda/-alkylation of 2, 4-dimethyl-1 /-/-imidazole according to the previously described general procedure (GP9).1H-NMR (CDCI3; 300 MHz): delta = 6.50 (s; 1 H), 3.76 (t, J = 6.2 Hz, 2H), 2.91 (t, J = 6.2 Hz, 2H), 2.28 (s, 3H), 2.09 (s, 3H).

Reference： [1]Patent: WO2008/78291,2008,A1 .Location in patent: Page/Page column 72-73

79
[ 930-62-1 ]
[ 5292-43-3 ]
[ 942204-60-6 ]
[ 942204-59-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In N,N-dimethyl-formamide; at 20℃; for 0.25h;	A solution of 2,4-dimethylimidazole (8-40 g; 87.38 mmol) in dry DMF (250 mL) was treated with potassium tert-butoxide (9.806 g; 87.38 mmol). The mixture was stirred at ambient temperature until homogenous. tert-Butyl bromoacetate (15.29 mL; 104.9 mmol) was added dropwise. The solution was stirred for 15 min, then diluted with isopropyl acetate (400 mL) and washed with pH7 phosphate buffer (3×250 mL). The organic was dried over MgSO4, filtered and evaporated to an oil. The crude product (consisting of the two title compounds) was chromatographed over silica gel (0% to 10% MeOH/CH2Cl2; linear gradient). All fractions containing the two products were combined. The residue was rechromatographed on Chiralcel OD stationary phase (Daicel Chemical Industries Ltd., Chiralcel Technologies Inc.; 10% ethanol/heptane; lambda=220 nM). The more mobile 2,5 isomer and less mobile 2,4 isomer were obtained.500 MHz 1H NMR (CDCl3): (2,4 isomer) delta 6.49 (s, 1H), 4.39 (s, 2H), 2.24 (s, 3H), 2.17 (s, 3H), 1.42 (s, 9H); (2,5 isomer) delta 6.67 (s, 1H), 4.41 (s, 2H), 2.35 (s, 3H), 2.15 (s, 3H), 1.48 (s, 9H).
		Example 2; Step A 2,4-dimethyI-l/7-imidazol-l-yIacetic acid teri-butyl ester and 2,5-dimethyl-l/*r-imidazol-l- ylacetic acid tert-butyl ester; A solution of 2,4-dimethylimidazole (8.4Og; 87.38mmol) in dry DMF (25OmL) was treated with potassium ter/-butoxide (9.806g; 87.38mmol). The mixture was stirred at ambient temperature until homogenous. tert-Buty bromoacetate (15.29mL; 104.9mmo.) was added dropwise. The solution was stirred for 15min, then diluted with isopropyl acetate (40OmL) and washed with pH7 phosphate buffer (3x250mL). The organic was dried over MgStheta4, filtered and evaporated to an oil. The crude product(consisting of the two title compounds) was chromatographed over silica gel (0% to 10% MeOH/CH2Cl2; linear gradient). All fractions containing the two products were combined. The residue was rechromatographed on Chiralcel OD stationary phase (Daicel Chemical Industries Ltd., Chiralcel Technologies Inc.; 10%etha?o I/heptane; lambda=220nM). The more mobile 2,5 isomer and less mobile 2,4 isomer were obtained. lHNMR (CDCl3): (2,4 isomer) delta 6.49 (s, IH), 4.39 (s, 2H), 2.24 (s,3H), 2.17 (s, 3H), 1.42 (s, 9H); (2,5 isomer) delta 6.67 (s, IH), 4.41 (s, 2H), 2.35 (s, 3H), 2.15 (s, 3H), 1.48 (s, 9H).

Reference： [1]Patent: US2009/30012,2009,A1 .Location in patent: Page/Page column 17
[2]Patent: WO2007/70433,2007,A2 .Location in patent: Page/Page column 34

80
[ 930-62-1 ]
[ 1042443-53-7 ]
[ 1042443-37-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 3405 - 3411

81
[ 930-62-1 ]
[ 1095274-77-3 ]
[ 1095274-78-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 4,7-dimethoxy-1,10-phenanthroline; caesium carbonate;copper(I) oxide; In propyl cyanide; at 80℃;	Copper oxide (0.045 g, 0.316 mmol), 4,7-bis(methyloxy)-1 ,10-phenanthroline (0.228 g, 0.948 mmol), polyethylene glycol (1.248 g, 11.76 mmol), cesium carbonate (2.88 g, 8.84 mmol), 2,4-dimethyl-1 H-imidazole (0.729 g, 7.58 mmol) and 1 ,1-dimethylethyl3-chloro-5-iodobenzoate (D53, 2.139 g, 6.32 mmol) were transferred into a dried round-bottomed flask vial and capped with a rubber septum. The flask was then evacuated and backfilled with argon - this process was repeated several times. Butyronitrile (3.12 ml.) was then added and the mixture was stirred at 80 0C overnight during which time the reaction had evaporated to dryness. Further butyronitrile (3.12 ml.) was added and the mixture stirred at 80 0C over the weekend.The mixture was diluted with dichloromethane and then filtered through celite. The filtrate was concentrated in vacuo and the resulting crude material (2.8 g) was purified by flash chromatography with a gradient of 0 - 100% ethyl acetate in hexane to afford the title compound as a white solid.LC/MS (ES+ve): [M+H]+ at m/z 307, 309 (C16H19CIN2O2 requires [M+H]+ at m/z 307, 309)

Reference： [1]Patent: WO2009/819,2008,A1 .Location in patent: Page/Page column 63

82
3-(4-bromophenyl)-1,4-diazaspiro[4.4]non-3-en-2-one [ No CAS ]
[ 930-62-1 ]
[ 1132817-81-2 ]

Yield	Reaction Conditions	Operation in experiment
	With bis(2,2,6,6-tetramethyl-3,5-heptanedionato)copper(II); potassium tert-butylate; In N,N-dimethyl-formamide; at 20 - 120℃; for 184.08h;	A stirred solution of 3-(4-bromophenyl)-1 ,4-diazaspiro[4.4]non-3-en-2-one (D3) (770 mg2,4-dimethyl-1 H-imidazole (379 mg, 3.94 mmol) and copper bis(2,2,6,6-tetramethyl- 3,5-heptanedionate) (337 mg, 0.788 mmol) in DMF (3 ml) at room temperature, under argon was treated with potassium tert-butoxide (1179 mg, 10.51 mmol). After stirring at room temperature for 5 min, the mixture was heated to 12O0C and this temperature was maintained for 16 h. Further batches of the imidazole (379 mg) and copper bis(2, 2,6,6- tetramethyl-3,5-heptanedionate) (337 mg) were added and heating was continued for 7 days. The reaction mixture was cooled and diluted with saturated aqueous sodium bicarbonate solution (100 ml) and ethyl acetate (100 ml). After mixing, the mixture was filtered through Kieselghur. The ethyl acetate layer was separated and the aqueous phase re-extracted with ethyl acetate (50 ml). The combined organics were dried <n="50"/>(MgSO4) and evaporated. The residue was applied in MeOH to an SCX column (10 g). After washing with MeOH the product was eluted with 2M NH3-MeOH. Evaporation afforded a brown gum. Chromatography (1 Og isolute column, 0-2% MeOH-DCM) afforded, after solvent removal, material (250 mg) consistent with presence of 2 isomers in approx 9:1 ratio with the major component subsequently confirmed (by 1H NMR nOe studies at the final product stage) as the title compound.Mass Spectrum (Electrospray LC/MS): Found 309 (MH+). Ci8H20N4O requires 308. Ret. time 1.02 min

Reference： [1]Patent: WO2009/34061,2009,A1 .Location in patent: Page/Page column 48-49

83
[ 930-62-1 ]
[ 1842-63-3 ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 9375 - 9386

84
[ 930-62-1 ]
[ 75-11-6 ]
C₁₃H₂₂N₄⁽²⁺⁾*2I^(1-) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 9375 - 9386

85
[ 624-28-2 ]
[ 930-62-1 ]
[ 1217273-65-8 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In N,N-dimethyl-formamide; at 100℃;Inert atmosphere;	2,5-Dibromopyridine (1.2 g; 5.0 mmol) and 2,4-dimethyl-1H-imidazole (0.5 g; 5.0 mmol) were dissolved in 10 mL of DMF. PdCl2(dppf).CH2Cl2 (20 mg; 0.025 mmol) was added, followed by ButOK (0.56 g; 5.0 mmol). The reaction mixture was degassed under Ar for 30 min. and then heated at 100 C. overnight. After cooling to r.t., the mixture was filtered through Celite and washed with EtOAc (50 mL). The filtrate was washed with 10% NH4Cl and brine, dried (Na2SO4) and concentrated. The residue was purified by preparative TLC (3% MeOH/DCM) and the product was obtained as a white solid. 1H NMR (400 MHz, CDCl3, ppm): 8.62 (d, J=2.0 Hz, 1H); 7.97 (dd, J=8.0, 2.0 Hz, 1H); 7.23 (d, J=8.0 Hz, 1H); 7.01 (s, 1H); 2.65 (s, 3H); 2.30 (s, 3H). MS (m/z): 254 [M+H].

Reference： [1]Patent: US2010/69441,2010,A1 .Location in patent: Page/Page column 33-34

86
[ 930-62-1 ]
bis(4-(dimethylamino)phenyl)methylium tetrafluoroborate [ No CAS ]
BF₄^(1-)*C₂₂H₂₈N₄*H⁽¹⁺⁾ [ No CAS ]
BF₄^(1-)*C₂₂H₂₈N₄*H⁽¹⁺⁾ [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2010,vol. 8,p. 1929 - 1935

87
[ 66-27-3 ]
[ 930-62-1 ]
[ 1739-81-7 ]
[ 1842-63-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetone; at 20℃; for 16h;Inert atmosphere;	A solution of <strong>[66-27-3]methyl mesylate</strong> (25.4 mL, 300 mmol) in acetone (50 mL) was added dropwise to a stirred mixture of 2,4-dimethylimidazole (25.00 g, 260 mmol), potassium carbonate (55.20 g, 400 mmol) and acetone (500 mL). Stirring under argon was then continued at room temperature for 16 hours. The resulting solid was filtered off, and the solvent was removed under reduced pressure. The residue was triturated with THF (200 mL) to give crystalline product (59-3) (14.47 g, 25% yield).The filtrate was treated with activated charcoal, filtered through a layer of Celite, and the solvent was removed under reduced pressure. Upon storage of the residue at room temperature, some crystalswere formed, and these crystals were separated, washed with THF and dried in a vacuum oven to give1,2,4-trimethylimidazole (59-1) (4.01 g, 14% yield). Concentration of the filtrate gave a mixture of isomeric imidazoles (59-1) and (59-2) (12.19 g, 43% yield).

Reference： [1]Patent: WO2018/161025,2018,A1 .Location in patent: Page/Page column 16; 17

88
[ 258515-65-0 ]
[ 930-62-1 ]
C₁₉H₂₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With copper(l) iodide; potassium tert-butylate; (1S,2S)-N,N'-dimethyl-1,2-diaminocyclohexane; In 1-methyl-pyrrolidin-2-one; at 160℃;Inert atmosphere;	1. A mixture of 1 (Key Organics, 15 g, 48.08 mmol), 2,4-dimethyl-lH-imidazole (13.8 g, 144.23 mmol), (S,S)-N,N'-dimethyl-l,2-diaminocyclohexane (1.37 g, 9.62 mmol), t-BuOK (16.15 g, 144.23 mmol) and Cul (4.58 g, 24.04 mmol) in NuMuRho (150 mL) was stirred at 160 C overnight under 2. The mixture was cooled to RT, sat. aq. NaHCC (50 mL) and B0C2O (26.2 g, 120 mmol) were added and the resulting mixture was stirred at RT overnight. The mixture was concentrated, and the residue was purified by chromatography on silica gel to give a material which was purified by Prep-HPLC to give 2 (6 g, 38% yield) as a pale-yellow oil. MS (ESI): mass calcd. for C19H25N3O2 327.43, m/z found 327.9 [M+H]+.

Reference： [1]Patent: WO2019/79519,2019,A1 .Location in patent: Page/Page column 35

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