[ CAS No. 54550-36-6 ] {[proInfo.proName]}

Name: 54550-36-6|1-Bromo-2-(2-ethoxyethoxy)ethane|98% stab. with potassium carbonate
Brand: Ambeed
SKU: A387447
Price: 18.0 USD
Availability: InStock
Rating: 96 (27 reviews)

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 54550-36-6 * 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 [ 54550-36-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 54550-36-6 ]

SDS Specification

Alternatived Products of [ 54550-36-6 ]

Product Details of [ 54550-36-6 ]

CAS No. :	54550-36-6	MDL No. :	MFCD00051920
Formula :	C₆H₁₃BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UEDIWIFQWRXXJG-UHFFFAOYSA-N
M.W :	197.07	Pubchem ID :	7015324
Synonyms :

Safety of [ 54550-36-6 ]

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 [ 54550-36-6 ]

* 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.

Downstream synthetic route of [ 54550-36-6 ]

[ 54550-36-6 ] Synthesis Path-Downstream 1~88

1
[ 111-90-0 ]
[ 54550-36-6 ]

Reference： [1]Journal of Pharmacology and Experimental Therapeutics,2006,vol. 318,p. 1307 - 1314
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 5217 - 5226
[3]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083
[4]Journal of the American Chemical Society,1941,vol. 63,p. 2779

2
[ 54550-36-6 ]
[ 1066-26-8 ]
[ 110469-22-2 ]

Reference： [1]Journal of the American Chemical Society,1937,vol. 59,p. 213

3
[ 54550-36-6 ]
[ 17356-08-0 ]
[ 88778-22-7 ]

Reference： [1]Journal of the American Chemical Society,1947,vol. 69,p. 2672

4
[ 54550-36-6 ]
[ 119-36-8 ]
2-[2-(2-ethoxy-ethoxy)-ethoxy]-benzoic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1952,vol. 74,p. 1821,1823

5
[ 54550-36-6 ]
[ 1074-82-4 ]
[ 23702-87-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 944 - 950
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 1069 - 1077

6
[ 54550-36-6 ]
C₄₄H₄₈O₄ [ No CAS ]
C₆₈H₉₆O₁₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,1993,vol. 34,p. 1971 - 1974

7
[ 54550-36-6 ]
[ 641-74-7 ]
[ 121693-39-8 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1988,vol. 37,p. 528 - 533
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988,p. 627 - 632

8
[ 54550-36-6 ]
[ 641-74-7 ]
[ 121693-39-8 ]
[ 121693-48-9 ]

Reference： [1]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1988,vol. 37,p. 533 - 537
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988,p. 632 - 637
[2]Bulletin of the Academy of Sciences of the USSR Division of Chemical Science,1988,vol. 37,p. 533 - 537
Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1988,p. 632 - 637

9
[ 111-46-6 ]
[ 54550-36-6 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 944 - 950
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 1069 - 1077

10
[ 54550-36-6 ]
[ 215181-67-2 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

11
[ 54550-36-6 ]
[ 6361-05-3 ]
ethyl 2-diphenylphosphinoyl-5,8-dioxadecanoate [ No CAS ]

Reference： [1]Russian Journal of General Chemistry,1994,vol. 64,p. 1451 - 1455
Zhurnal Obshchei Khimii,1994,vol. 64,p. 1629 - 1633

12
[ 54550-36-6 ]
[ 288302-12-5 ]
5,11,17,23-Tetra-tert-butyl-2,14-bis(1,4,7-trioxanonyl)calix[4]arene [ No CAS ]

Reference： [1]Collection of Czechoslovak Chemical Communications,1998,vol. 63,p. 2009 - 2014

13
[ 54550-36-6 ]
[ 16433-88-8 ]
2,7-dibromo-9-(3,6-dioxaoctyl)fluorene [ No CAS ]

Reference： [1]Chemical Communications,2001,p. 2426 - 2427

14
[ 27970-32-7 ]
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methyloxazolidinium bromide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

15
[ 109-02-4 ]
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methylmorpholinium bromide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

16
[ 616-47-7 ]
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methylimidazolium bromide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

17
[ 6086-21-1 ]
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methyltriazolium bromide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

18
[ 54550-36-6 ]
[ 20662-53-7 ]
1-{1-[2-(2-ethoxyethoxy)ethyl]piperidin-4-yl}-1,3-dihydro-2H-benzimidazol-2-one trifluoroacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With potassium carbonate; In acetonitrile; at 50℃; for 48h;	Example 3. 1-{1-[2-(2-ethoxyethoxy)ethyl]piperidin-4-yl}-1,3-dihydro-2H- benzimidazol-2-one; The mixture of 1-piperidin-4-yl-1,3-dihydro-2/-/-benzimidazol-2-one (100 mg, 0.46 mmol), potassium carbonate (250 mg, 1.81 mmol) and 1 -bromo-2-(2- ethoxyethoxy)ethane (0.1 ml_, 0.64 mmol) in acetonitrile (15 mL) was heated at 50 0C for 48 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved diluted in dichloromethane, washed with water and dried. The crude product was purified by prep LCMS (acetonitrile/water) to provide the pure compound as its TFA salt (39%). 1H NMR (400 MHz, CHLOROFORM-D): δ ppm 1.16 (t, J=7.03 Hz, 3 H), 1.95 (d, J=13.28 Hz, 2 H), 2.83 - 3.09 (m, 4 H), 3.26 - 3.39 (m, 2 H), 3.49 (q, J=7.03 Hz, 2 H), 3.52 - 3.59 (m, 2 H), 3.58 - 3.68 (m, 2 H), 3.78 - 4.02 (m, 4 H), 4.52 - 4.75 (m, 1 H), 6.84 - 7.15 (m, 3 H), 7.41 (d, J=7.03 Hz, 1 H), 10.16 (s, 1 H). MS: 334.0 (M+1).

Reference： [1]Patent: WO2007/142584,2007,A1 .Location in patent: Page/Page column 24

19
1-adamantan-1-yl-3-(5-hydroxypentyl)urea [ No CAS ]
[ 54550-36-6 ]
adamantan-1-yl-3-{5-[2-(2-ethoxyethoxy)ethoxy]pentyl}urea [ No CAS ]

Reference： [1]Journal of Pharmacology and Experimental Therapeutics,2006,vol. 318,p. 1307 - 1314

20
[ 178907-19-2 ]
[ 54550-36-6 ]
C₁₇H₂₃Cl₂N₃O₆S [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4599 - 4603

21
[ 54550-36-6 ]
[ 75178-90-4 ]
C₁₆H₃₃NO₅ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5217 - 5226

22
[ 885009-83-6 ]
[ 54550-36-6 ]
1-adamantan-1-yl-3-{4-[2-(2-ethoxyethoxy)ethoxy]cyclohexyl}urea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5217 - 5226

23
1-(adamantan-1-yl)-3-(3-hydroxyphenyl)urea [ No CAS ]
[ 54550-36-6 ]
C₂₃H₃₄N₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5217 - 5226

24
[ 676140-69-5 ]
[ 54550-36-6 ]
C₂₃H₃₄N₂O₄ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5217 - 5226

25
[ 852240-75-6 ]
[ 54550-36-6 ]
1-(adamantan-1-yl)-3-(5-(2-(2-ethoxyethoxy)ethoxy)pentyl)urea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 5217 - 5226

26
[ 54550-36-6 ]
[ 23702-88-7 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 944 - 950
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 1069 - 1077
[2]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

27
[ 54550-36-6 ]
[ 79688-28-1 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 944 - 950
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 1069 - 1077

28
[ 54550-36-6 ]
[ 79688-29-2 ]

Reference： [1]Journal of Organic Chemistry USSR (English Translation),1981,vol. 17,p. 944 - 950
Zhurnal Organicheskoi Khimii,1981,vol. 17,p. 1069 - 1077

29
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methylimidazolium bis(trifluoromethanesulfonyl)amide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

30
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methyltriazolium bis(trifluoromethanesulfonyl)amide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

31
[ 54550-36-6 ]
N-2-(2-ethoxyethoxy)ethyl-N-methyloxazolidinium bis(trifluoromethanesulfonyl)amide [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2004,vol. 2,p. 2728 - 2734

32
[ 54550-36-6 ]
[ 399037-02-6 ]

Reference： [1]Chemical Communications,2001,p. 2426 - 2427

33
[ 54550-36-6 ]
[ 1026538-44-2 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

34
[ 54550-36-6 ]
[ 162933-15-5 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

35
[ 54550-36-6 ]
[ 162933-10-0 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

36
[ 54550-36-6 ]
[ 162933-17-7 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

37
[ 54550-36-6 ]
1-<5-<(4,5-diphenyl-1H-imidazol-2-yl)thio>pentyl>-1-<2-(2-ethoxyethoxy)ethyl>-3-(1-methylethyl)urea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

38
[ 54550-36-6 ]
[ 162933-13-3 ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

39
[ 54550-36-6 ]
1-<5-<<4,5-bis<4-(methylthio)phenyl>-1H-imidazol-2-yl>thio>pentyl>-1-<2-(2-ethoxyethoxy)ethyl>-3-(1-methylethyl)urea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

40
[ 54550-36-6 ]
3-(2,4-difluorophenyl)-1-<5-<(4,5-diphenyl-1H-imidazol-2-yl)thio>pentyl>-1-<2-(2-ethoxyethoxy)ethyl>urea [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 1067 - 1083

41
[ 60-29-7 ]
[ 54550-36-6 ]
[ 403-01-0 ]
[ 584-08-7 ]
[ 117420-32-3 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetonitrile;	PART A -- Preparation of methyl 3-fluoro-4-[2-(2-ethoxyethoxy)-ethoxy]-benzoate. Into a 500-ml, round-bottom flask equipped with a magnetic stirrer, heating mantle and condenser were placed 5.7 g (33.5 mmol) <strong>[403-01-0]methyl 3-fluoro-4-hydroxybenzoate</strong>, 8.5 g (43.2 mmol) 1-bromo-2-(2-ethoxyethoxy)-ethane, 23.2 g of powdered anhydrous potassium carbonate and 350 ml acetonitrile. After stirring the reaction mixture under reflux for four hours, TLC analysis showed that none of the phenolic starting material remained. Three hundred ml of the acetonitrile was then distilled off and 300 ml dichloromethane was added. The reaction mixture was filtered through Celite and the solids were washed thoroughly with dichloromethane. Evaporation of the filtrate yielded product in the form of a yellow oil. Purification by flash chromatography on silica gel with 4percent ethyl ether in dichloromethane, followed by low temperature recrystallization from pentane, yielded 0.55 g of white crystals, 89percent, m.p. 33-36.5°C. The structure was confirmed by infrared, nuclear magnetic resonance and mass spectral analyses.

Reference： [1]Patent: EP258578,1993,B1

42
[ 54550-36-6 ]
[ 19812-93-2 ]
[ 117420-28-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile;	PART A -- Preparation of 4-[2-(2-ethoxyethoxy)ethoxy]-4'-cyanobiphenyl . To 0.975 g (five millimoles) of 4-hydroxy-4'-cyanobiphenyl dissolved with 1.08 g (5.5 millimoles) of 1-bromo 2-(2-ethoxyethoxy)ethane in 25 ml. of acetonitrile, 1.4 g (ten millimoles) of finely ground potassium carbonate were added. The reaction mixture was refluxed overnight. Thin layer chromatographic analysis indicated total conversion. The reaction mixture was cooled and filtered and the product was washed with acetonitrile and evaporated to a white solid. The product was recrystallized from isopropanol and dried in vacuo to two grams (93% yield) of a compound having the following formula structure:

Reference： [1]Patent: EP258578,1993,B1

43
[ 54550-36-6 ]
[ 25162-00-9 ]
(S)-1-[2-(2-ethoxy-ethoxy)-ethyl]-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	In acetic acid; for 72h;Heating / reflux;	To a stirred solution of (S)-nicotine (0.67 g, 4.1 mmol) in AcOH (20 ml) was added 1-bromo-2-(2-ethoxy-ethoxy)-ethane (1.97 g, 10.0 mmol).The mixture was heated at reflux for 3 days. AcOH was evaporated and the residue was dissolved in CHCl3.The mixture was washed with saturated aqueous NaHCO3, water and brine successively and dried.Evaporation of the solvent followed by titration with ether afforded 0.56 g (38%) of (S)-1-[2-(2-ethoxy-ethoxy)-ethyl]-3-(1-methyl-pyrrolidin-2-yl)-pyridinium bromide (NONB-3O6O) as a brown oil. 1H NMR (300 MHz, CDCl3) δ 9.65 (1H, d, J=6.0 Hz), 9.26 (1H, s), 8.44 (1H, d, J=7.8 Hz), 7.99 (1H, dd, J=7.8, 6.0 Hz), 5.27 (2H, t, J=4.8 Hz), 4.06 (2H, t, J=4.8 Hz), 3.64 (2H, m), 3.41-3.60 (5H, m), 3.26 (1H, m), 2.43 (2H, m), 2.25 (3H, s), 1.91 (2H, m), 1.60 (1H, m), 1.16 (3H, t, J=6.9 Hz); 13C NMR (75 MHz, CDCl3) δ 145.87, 144.40*2, 144.02, 127.85, 70.83, 69.72, 69.57, 67.17, 66.77, 61.41, 56.91, 40.67, 36.02, 23.41, 15.47; Anal. Calcd for C16H27BrN2.0.5H2O: C, 52.18; H, 7.66; N, 7.61. Found: C, 52.22; H, 7.68; N, 7.50.

Reference： [1]Patent: US2003/225142,2003,A1 .Location in patent: Page 13

44
[ 54550-36-6 ]
[ 1692-25-7 ]
[ 725251-83-2 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); bis(N-methylimidazol-2-yl)methane; In N,N-dimethyl acetamide; at 80℃; for 2h;	Examples 19 to 36 The process of Example 1 is repeated in a similar manner except that 0.40 mmol of boron compound as listed in Table 3 is used in place of p-methoxyphenylboronic acid and that 0.30 mmol of the organic halide compound as shown in Table 3 is used in place of 1-bromooctane, and each solvent as shown in Table 3 is used in place of N,N-dimethylacetamide, thereby the desired compounds as listed in Table 3 are obtained.

Reference： [1]Patent: EP1439157,2004,A2 .Location in patent: Page 12-16

45
[ 725251-81-0 ]
[ 54550-36-6 ]
[ 725251-84-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); bis(N-methylimidazol-2-yl)methane; In 1,2-dimethoxyethane; at 80℃; for 2h;	Examples 19 to 36 The process of Example 1 is repeated in a similar manner except that 0.40 mmol of boron compound as listed in Table 3 is used in place of p-methoxyphenylboronic acid and that 0.30 mmol of the organic halide compound as shown in Table 3 is used in place of 1-bromooctane, and each solvent as shown in Table 3 is used in place of N,N-dimethylacetamide, thereby the desired compounds as listed in Table 3 are obtained.

Reference： [1]Patent: EP1439157,2004,A2 .Location in patent: Page 12-16

46
[ 54550-36-6 ]
[ 55499-43-9 ]
[ 725251-82-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;bis(1,5-cyclooctadiene)nickel (0); bis(N-methylimidazol-2-yl)methane; In N,N-dimethyl acetamide; at 80℃; for 2h;	Examples 19 to 36 The process of Example 1 is repeated in a similar manner except that 0.40 mmol of boron compound as listed in Table 3 is used in place of p-methoxyphenylboronic acid and that 0.30 mmol of the organic halide compound as shown in Table 3 is used in place of 1-bromooctane, and each solvent as shown in Table 3 is used in place of N,N-dimethylacetamide, thereby the desired compounds as listed in Table 3 are obtained.

Reference： [1]Patent: EP1439157,2004,A2 .Location in patent: Page 12-16

47
[ 54550-36-6 ]
[ 226908-20-9 ]
6-Amino-9-benzyl-8-hydroxy-2-[2-(2-ethoxyethoxy)ethyl]thio}purine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With potassium carbonate; In N-methyl-acetamide;	Example 76 6-Amino-9-benzyl-8-hydroxy-2-[2-(2-ethoxyethoxy)ethyl]thio}purine Crude 6-amino-9-benzyl-8-hydroxy-2-mercaptopurine (470 mg, 1.7 mmol) was suspended in dimethylformamide (100 ml). To the suspension were added potassium carbonate (350 mg, 2.5 mmol) and 1-ethoxy-2-(2-bromoethoxy)ethane (505 mg, 2.6 mmol) in order. The mixture was stirred at room temperature for 2 hours. The solvent was removed in vacuo, and the residue was purified by silica gel chromatography (1% methanol/chloroform) to give the subject compound (147 mg, yield 22%). 1H-NMR (DMSO-d6) δ: 10.11 (1H, s), 7.31 (5H, m), 6.54 (2H, br s), 4.88 (2H, s), 3.58 (2H, t, J=6.9 Hz), 3.51-3.36 (6H, m), 3.18 (2H, t, J=6.9 Hz), 1.07 (3H, t, J=6.9 Hz).

Reference： [1]Patent: US6329381,2001,B1

48
[ 54550-36-6 ]
[ 871024-78-1 ]

Yield	Reaction Conditions	Operation in experiment
		(i) Production of 4-chloro-5-[2-(2-ethoxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidine To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (300 mg) in N,N-dimethylformamide (2.0 mL) was added cesium carbonate (728 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (496 mg), and the mixture was stirred at room temperature for 20 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (20 mLx3). The organic layer was washed with saturated brine (20 mLx3) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (silica gel, eluent:hexane/ethyl acetate=9/1 → 0/10). The object fraction was concentrated under reduced pressure and dried to give the title compound (440 mg) as a colorless transparent oil. 1H-NMR (CDCl3) δ 1.17 (3H, t, J= 7.1 Hz), 3.40-3.58 (6H, m), 3.87 (2H, t, J= 5.1 Hz), 4.69 (2H, t, J= 5.1 Hz), 6.70 (1H, d, J= 3.3 Hz), 7.63 (1H, d, J= 3.3 Hz), 8.69 (1H, s).

Reference： [1]Patent: EP1752457,2007,A1 .Location in patent: Page/Page column 133

49
[ 54550-36-6 ]
[ 131786-61-3 ]
C₁₈H₂₃NO₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In acetonitrile; at 180℃; for 0.25h;Microwave irradiation;	EXAMPLE 25 - General procedure 17 (GP 17) (based on general scheme 7 and 8); 4-{4-[2-(2-Ethoxy-ethoxy)-ethoxy]-5-methyl-thiazol-2-yl}-benzoic acid (compound of formula 64); [0236] Methyl 4-(4-hydroxy-5-methyl-l,3-thiazol-2-yl)benzenecarboxylate (0.2 mmol, 50 mg), l-(2-bromoethoxy)-2-ethoxyethane (0.4 mmol, 79 mg), potassium carbonate (0.4 mmol, 60 mg), potassium iodide (0.2 mmol, 33 mg) was transferred to a MW vial and 1 mL of CH3CN was added. The vial was capped and the mixture was irradiated for 15 min at 180 0C. The vial was decapped and lithium hydroxide monohydrate (0.5 mmol, 21 mg) and 0.3 mL H2O were added and the vial was irradiated for 7 min at 160 C. The reaction mixture EPO <DP n="67"/>was transferred to a hydromatrix that was pretreated with water and extracted with EtOAc. The filtrate was collected and concentrated in vacuo, and 20 mg of the concentrate was purified by prep LC/MS yielding the title compound (2 mg). LC/MS: Purity (UVMS): 100/96.

Reference： [1]Patent: WO2007/9083,2007,A2 .Location in patent: Page/Page column 65-66

50
[ 54550-36-6 ]
[ 40501-41-5 ]
[ 1198567-49-5 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 5231 - 5234

51
[ 54176-27-1 ]
[ 54550-36-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 5231 - 5234

52
[ 71637-34-8 ]
[ 54550-36-6 ]
[ 1167988-08-0 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 9158 - 9159

53
[ 54550-36-6 ]
[ 1236764-70-7 ]
[ 1236766-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 100℃; for 4h;	Example 1483-[4-(2-Cyclopropylethoxy)phenyl]-2-[2-(2-ethoxyethoxy)ethyl]sulfanyl}-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; A mixture of 3-[4-(2-cyclopropylethoxy)phenyl]-2-thioxo-1,2,3, 5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (300 mg) obtained in Example 15, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (197 mg), sodium iodide (149 mg), a 1 M aqueous solution of sodium hydrogen carbonate (1 ml) and N,N-dimethylformamide (20 ml) was stirred for 4 hours at 100 C., and then was concentrated under reduced pressure. Ethyl acetate and water were added to the residue, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography, and then was recrystallized from a mixed solvent of ethyl acetate/hexane. Thus, the title compound (311 mg) was obtained as a white solid.1H NMR (300 MHz, DMSO-d6) δ ppm 0.12-0.18 (2H, m), 0.43-0.49 (2H, m), 0.80-0.95 (1H, m), 1.06 (3H, t, J=6.8 Hz), 1.67 (2H, q, J=6.8 Hz), 3.24 (2H, t, J=6.5 Hz), 3.35-3.47 (4H, m), 3.47-3.53 (2H, m), 3.60 (2H, t, J=6.4 Hz), 4.10 (2H, t, J=6.6 Hz), 6.35 (1H, d, J=2.4 Hz), 7.06 (2H, d, J=8.9 Hz), 7.24 (2H, d, J=8.9 Hz), 7.38 (1H, t, J=2.4 Hz), 12.10 (1H, br. s.).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 100

54
[ 54550-36-6 ]
[ 1236764-71-8 ]
[ 1236766-16-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 90℃; for 4h;	Example 1522-[2-(2-Ethoxyethoxy)ethyl]sulfanyl}-3-{4-[(2,2,2-trifluoroethoxy)methyl]phenyl}-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; A mixture of 2-thioxo-3-{4-[(2,2,2-trifluoroethoxy)methyl]phenyl}-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (250 mg) obtained in Example 16, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (197 mg), sodium iodide (149 mg), a 1 M aqueous solution of sodium hydrogen carbonate (840 μl) and N,N-dimethylformamide (10 ml) was stirred for 4 hours at 90 C., cooled to room temperature, and then concentrated under reduced pressure. Ethyl acetate and water were added to the residue, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography, and then was recrystallized from diisopropyl ether, and thus the title compound (187 mg) was obtained as a white solid.1H NMR (300 MHz, DMSO-d6) δ ppm 1.06 (3H, t, J=7.0 Hz), 3.25 (2H, t, J=6.4 Hz), 3.34-3.46 (4H, m), 3.47-3.53 (2H, m), 3.60 (2H, t, J=6.4 Hz), 4.20 (2H, q, J=9.2 Hz), 4.77 (2H, s), 6.37 (1H, d, J=2.7 Hz), 7.35-7.40 (3H, m), 7.51 (2H, d, J=8.3 Hz), 12.15 (1H, br. s.).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 101

55
[ 54550-36-6 ]
[ 1236764-72-9 ]
[ 1236766-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 90℃; for 4h;	Example 1613-[4-(Cyclopropylmethoxy)-3-methylphenyl]-2-[2-(2-ethoxyethoxy)ethyl]sulfanyl}-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; A mixture of 3-[4-(cyclopropylmethoxy)-3-methylphenyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (230 mg) obtained in Example 17, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (197 mg), sodium iodide (149 mg), a 1 M aqueous solution of sodium hydrogen carbonate (840 μl) and N,N-dimethylformamide (20 ml) was stirred for 4 hours at 90 C., cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography, and then was recrystallized from a mixed solvent of ethyl acetate/diisopropyl ether. Thus, the title compound (182 mg) was obtained as a white solid.1H NMR (300 MHz, DMSO-d6) δ ppm 0.34-0.41 (2H, m), 0.56-0.64 (2H, m), 1.06 (3H, t, J=7.0 Hz), 1.20-1.36 (1H, m), 2.20 (3H, s), 3.23 (2H, t, J=6.4 Hz), 3.34-3.47 (4H, m), 3.47-3.53 (2H, m), 3.60 (2H, t, J=6.6 Hz), 3.84-3.98 (2H, m), 6.34 (1H, d, J=3.0 Hz), 6.96-7.05 (1H, m), 7.05-7.13 (2H, m), 7.37 (1H, d, J=2.7 Hz), 12.09 (1H, s).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 104

56
[ 54550-36-6 ]
[ 1236764-73-0 ]
[ 1236766-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 90℃; for 4h;	Example 1633-[3-Chloro-4-(cyclopropylmethoxy)phenyl]-2-[2-(2-ethoxyethoxy)ethyl]sulfanyl}-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; A mixture of 3-[3-chloro-4-(cyclopropylmethoxy)phenyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (243 mg) obtained in Example 18, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (197 mg), sodium iodide (149 mg), a 1 M aqueous solution of sodium hydrogen carbonate (840 μl) and N,N-dimethylformamide (20 ml) was stirred for 4 hours at 90 C., cooled to room temperature, and then concentrated under reduced pressure. Water was added to the residue, and then the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by chromatography, and then was recrystallized from a mixed solvent of ethyl acetate/diisopropyl ether. Thus, the title compound (158 mg) was obtained as a white solid.1H NMR (300 MHz, DMSO-d6) δ ppm 0.36-0.42 (2H, m), 0.59-0.66 (2H, m), 1.06(3H, t, J=7.0 Hz), 1.23-1.38 (1H, m), 3.25 (2H, t, J=6.4 Hz), 3.35-3.46 (4H, m), 3.48-3.53 (2H, m), 3.61 (2H, t, J=6.4 Hz), 3.95-4.07 (2H, m), 6.35 (1H, d, J=2.7 Hz), 7.24 (1H, d, J=8.7 Hz), 7.30 (1H, dd, J=8.7, 2.3 Hz), 7.39 (1H, d, J=2.7 Hz), 7.53 (1H, d, J=2.3 Hz), 12.14 (1H, br. s.).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 104-105

57
[ 54550-36-6 ]
[ 1236764-56-9 ]
[ 1236765-42-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 100℃; for 2h;	Example 792-[2-(2-Ethoxyethoxy)ethyl]sulfanyl}-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; A 1 M aqueous solution of sodium hydrogen carbonate (1.0 ml) was added to a mixture of 2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,5 -tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (341 mg) obtained by the method of Example 2, or a method pursuant to thereto, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (197 mg), sodium iodide (150 mg) and N,N-dimethylformamide (10 ml), and the resulting mixture was stirred for 2 hours at 100 C. The reaction mixture was returned to room temperature, and then the solvent was distilled off under reduced pressure. The residue was diluted with ethyl acetate, and the dilution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by chromatography, and then was recrystallized from a mixed solvent of ethyl acetate/hexane. Thus, the title compound (272 mg) was obtained as a white powder.1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.19 (3H, t, J=7.1 Hz), 3.36 (2H, t, J=6.6 Hz), 3.51 (2H, d, J=7.1 Hz), 3.54-3.60 (2H, m), 3.61-3.67 (2H, m), 3.75 (2H, t, J=6.6 Hz), 4.41 (2H, q, J=8.0 Hz), 6.43 (1H, d, J=2.3 Hz), 7.03-7.12 (2H, m), 7.20-7.30 (3H, m), 9.61 (1H, br. s.).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 78

58
[ 54550-36-6 ]
[ 1236764-60-5 ]
[ 1236766-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 100℃; for 15h;	Example 1423-[4-(Cyclopropylmethoxy)phenyl]-2-[2-(2-ethoxyethoxy)ethyl]sulfanyl}-3,5-dihydro-4H-pyrrolo[3,2-d]pyrimidin-4-one; A 1 M aqueous solution of sodium hydrogen carbonate (0.64 ml) was added to a mixture of 3-[4-(cyclopropylmethoxy)phenyl]-2-thioxo-1,2,3,5-tetrahydro-4H-pyrrolo[3,2-d]pyrimidin-4-one (200 mg) obtained by the method of Example 6, or a method pursuant to thereto, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (126 mg), sodium iodide (96 mg) and N,N-dimethylformamide (10 ml), and the resulting mixture was stirred for 15 hours at 100 C. The reaction mixture was returned to room temperature, and then was diluted with ethyl acetate. The dilution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by chromatography, and then was recrystallized from a mixed solvent of ethyl acetate/hexane. Thus, the title compound (183 mg) was obtained as a white powder.1H NMR (300 MHz, DMSO-d6) δ ppm 0.32-0.39 (2H, m), 0.56-0.64 (2H, m), 1.06 (3H, t, J=7.0 Hz), 1.22-1.30 (1H, m), 3.23 (2H, t, J=6.4 Hz), 3.35-3.53 (6H, m), 3.60 (2H, t, J=6.4 Hz), 3.89 (2H, d, J=6.8 Hz), 6.35 (1H, d, J=2.8 Hz), 7.04 (2H, d, J=8.9 Hz), 7.23 (2H, d, J=8.9 Hz), 7.38 (1H, d, J=2.8 Hz), 12.12 (1H, s).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 98

59
[ 54550-36-6 ]
[ 1236764-86-5 ]
[ 1236766-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; sodium iodide; In water; N,N-dimethyl-formamide; at 100℃; for 2h;	Example 1922-[2-(2-Ethoxyethoxy)ethyl]sulfanyl}-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one; A 1 M aqueous solution of sodium hydrogen carbonate (0.44 ml) was added to a mixture of 2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one (150 mg) obtained by the method of Example 26, or a method pursuant to thereto, <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (130 mg), sodium iodide (66 mg) and N,N-dimethylformamide (5 ml), and the resulting mixture was stirred for 2 hours at 100 C. The reaction mixture was returned to room temperature, and then was diluted with ethyl acetate. The dilution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by chromatography, and then was recrystallized from a mixed solvent of ethyl acetate/hexane. Thus, the title compound (128 mg) was obtained as a white powder.1H NMR (300 MHz, DMSO-d6) δ ppm 1.06 (3H, t), 3.25 (2H, t, J=6.4 Hz), 3.34-3.47 (4H, m), 3.47-3.54 (2H, m), 3.61 (2H, t, J=6.4 Hz), 4.86 (2H, q, J=8.7 Hz), 6.43 (1H, d, J=3.4 Hz), 6.98 (1H, d, J=3.4 Hz), 7.18 (2H, d, J=8.7 Hz), 7.30 (2H, d, J=8.7 Hz), 11.89 (1H, br. s.).

Reference： [1]Patent: US2010/190747,2010,A1 .Location in patent: Page/Page column 114

60
[ 54550-36-6 ]
disodium maleonitriledithiolato [ No CAS ]
[ 1360897-05-7 ]

Yield	Reaction Conditions	Operation in experiment
86%	In ethanol; at 20℃; for 72h;	2-(2-Ethoxyethoxy)ethyl bromide (1.00 mL, 6.68 mmol) dissolved in 1 mL of ethanol was added to dimercaptomaleonitrile disodium salt (1, 500 mg, 2.69 mmol) in anhydrous ethanol (20 mL) and stirred at room temperature for another 72 h. After the solvent was evaporated, the residual oil was chromatographed (n-hexane/ethyl acetate, 7:5, v/v) to give 3 as yellow oil (869 mg, 86%): Rf (n-hexane/ethyl acetate, 7:5, v/v) = 0.36. 1H NMR (400 MHz, CDCl3): δ 3.76 (t, 4H, 3J = 6 Hz), 3.64 (m, 4H), 3.58 (m, 4H), 3.52 (q, 4H, 3J = 7 Hz, 2× CH2CH3), 3.32 (t, 4H, 3J = 6 Hz), 1.21 (t, 6H, 3J = 7 Hz, 2× CH3). 13C NMR (100 MHz, CDCl3): δ 121.2, 112.1, 70.7, 69.7, 69.5, 66.7, 34.8, 15.1. MS (ES): m/z 397 [M+Na]+. Anal. Calcd. for C16H26N2O4S2: C, 51.31; H, 7.00; N, 7.48; S, 17.12. Found: C, 51.26; H, 7.22; N, 7.55; S, 17.16.

Reference： [1]Journal of Fluorine Chemistry,2012,vol. 135,p. 265 - 271

61
[ 54550-36-6 ]
{3,4,5-tris-[2-(2-ethoxyethoxy)ethyloxy]phenyl}methanol [ No CAS ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

62
[ 54550-36-6 ]
[ 1376712-00-3 ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

63
[ 54550-36-6 ]
[ 1376712-01-4 ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

64
[ 54550-36-6 ]
[ 1376712-02-5 ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

65
[ 54550-36-6 ]
[ 1376712-03-6 ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

66
[ 54550-36-6 ]
[ 1376711-93-1 ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

67
[ 54550-36-6 ]
[ 99-24-1 ]
C₂₆H₄₄O₁₁ [ No CAS ]

Reference： [1]Macromolecules,2012,vol. 45,p. 4540 - 4549

68
[ 54550-36-6 ]
[ 16433-88-8 ]
[ 399037-06-0 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrabutylammomium bromide; sodium hydroxide; In water; toluene; at 80℃; for 16h;Inert atmosphere;	The 2,7-dibromofluorene (2g, 6.21 mmol), <strong>[54550-36-6]1-bromo-2-(2-ethoxyethoxy)ethane</strong> (3.04 g, 15.5 mmol), tetrabutylammonium bromide (0.1 g, 0.3 mmol), sodium hydroxide (25 g, 625 mmol) were dissolved in the mixture solvent of toluene (50ml) water (25 mL) under nitrogen, and the mixture was stirred for 16 h at 80 C. Extracted with DCM, washed with brine and dried over by Na 2 SO4. The solvent was removed in vacuo, and the residue was separated with flash PE: EA = 8: 1) to give the expected product. Yield: 6.33 g (93%). 1H NMR (600 MHz, CDCl3): 1.15 (5.8H, t, J=7.02 Hz), 2.35 (3.9H, d, J=14.83 Hz), 2.78 (3.9H, d, J=14.83 Hz), 3.20 (3.7H, d, J=5.04 Hz), 3.33 (3.2H, d, J=3.42 Hz), 3.34 (3.3H, d, J=4.44 Hz), 3.42 (4.0H, q, J=7.02 Hz), 7.46 (0.8H, d, J=1.68 Hz), 7.47 (1.3H, d, J=1.62 Hz), 7.54 (1.9H, d, J=1.62 Hz).

Reference： [1]Chinese Chemical Letters,2020,vol. 31,p. 119 - 124
[2]Journal of Materials Chemistry,2012,vol. 22,p. 15490 - 15494
[3]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 916 - 923

69
[ 54550-36-6 ]
[ 1400703-89-0 ]
[ 1400705-13-6 ]

Yield	Reaction Conditions	Operation in experiment
55%	With triethylamine; sodium iodide; In N,N-dimethyl-formamide; at 120℃; for 0.333333h;microwave irradiation;	A mixture of (S)-2-({2-[3-(3-Hydroxy-phenyl)-propylamino]-4,6-dimethyl-pyrimidine-5- carbonyl}-amino)-3-[(thiophene-2-carbonyl)-amino]-propionic acid (0.20g, 0.40mmol), l-(2- bromoethoxy)-2-ethoxyethane (0.32g, 1.6mmol), sodium iodide (0.24g, 1.6mmol) and triethylamine (0.16g, 1.6mmol) in DMF (3ml) was microwaved at 120C for 20 minutes. The mixture was diluted with EtOAc (50ml), washed with brine, dried over Na2S04, filtered, concentrated in the presence of silica gel and chromatographed (50-100% EtOAc in hexane) to give the title compound (135.4mg, 55% yield). MS m/e 614.2 (M+H+).

Reference： [1]Patent: WO2012/123467,2012,A1 .Location in patent: Page/Page column 121

70
[ 54550-36-6 ]
[ 1421600-34-1 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 916 - 923

71
[ 54550-36-6 ]
[ 1421600-35-2 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2013,vol. 51,p. 916 - 923

72
[ 54550-36-6 ]
[ 513-42-8 ]
[ 1439378-31-0 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2262 - 2266

73
[ 54550-36-6 ]
[ 1439378-48-9 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2262 - 2266

74
[ 54550-36-6 ]
[ 1439378-32-1 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2262 - 2266

75
[ 54550-36-6 ]
[ 1439378-29-6 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2262 - 2266

76
[ 54550-36-6 ]
[ 1439378-35-4 ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2262 - 2266

77
[ 54550-36-6 ]
[ 4733-50-0 ]
[ 1456891-13-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium carbonate; In N,N-dimethyl-formamide; at 70℃; for 24h;Inert atmosphere;	2-(2-Ethoxyethoxy)ethyl bromide (1.96 mL, 12.90 mmol) and anhydrousK2CO3 (1.04 g, 10.40 mmol) were added to a well-stirred slurryof <strong>[4733-50-0]3,6-dihydroxy-1,2-benzenedicarbonitrile</strong> (830 mg, 5.20 mmol) inDMF (15 mL) and heated at 70 C for 24 h. After cooling to room temperature,the reaction contents were poured intowater and icemixture(100 mL) and left for 2 h. The resulting precipitate was isolated by filtration,washed three timeswith distilledwater (3 × 100 mL) and crystallizedfromethanol (50 mL) to give honey colored crystals (2) (1.63 g,80%). M.p. = 70-71 C. Rf (CH2Cl2 10:1) 0.77. UV-Vis (CH2Cl2) lambdamax[nm] (log epsilon): 346 (3.85). 1H NMR (400 MHz, pyridine-d5) delta: 7.42(s, 2H), 4.26 (t, 3J = 4.5 Hz, 4H), 3.83 (t, 3J = 4.5 Hz, 4H), 3.71 (t, 3J =4.5 Hz, m, 4H), 3.56 (t, 3J = 4.5 Hz, 4H), 3.42 (q, 3 J =7.0 Hz, 1H), 1.11(t, 3 J = 7.0 Hz, 6H).1H NMR (400 MHz, DMSO-d6) delta: 7.63 (s, 2H), 4.30(t, 3J = 4.5 Hz, 4H), 3.77 (t, 3J = 5.0 Hz, 4H), 3.58-3.61 (m, 4H), 3.52-3.60 (m, 4H), 3.46-3.49 (m, 4H), 3.41 (q, 3J=7.0 Hz, 4H), 1.08(t, 3J = 7.5 Hz, 6H). 13C NMR (100 MHz, pyridine-d5) delta: 155.7,120.2, 114.1, 105.0, 71.3, 70.4, 70.2, 69.5, 66.5, 15.5. 13C NMR (100 MHz,DMSO-d6) delta: 155.0, 120.8, 113.5, 103.0, 70.1, 69.6, 69.2, 68.6, 66.5, 15.0(graphical presentation of signal-structure allocation - SupplementaryData). MS (ESI): m/z 393.434 [M + H]+. Anal. Cal. for C20H28N2O6: C,61.21; H, 7.19; N, 7.14. Found: C, 61.12; H, 7.06; N, 7.11. Crystal data for2, CCDC 927434.

Reference： [1]Journal of Inorganic Biochemistry,2013,vol. 127,p. 62 - 72
[2]Journal of Inorganic Biochemistry,2016,vol. 155,p. 76 - 81

78
[ 54550-36-6 ]
[ 123-08-0 ]
[ 1618679-20-1 ]

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 5471 - 5478

79
[ 54550-36-6 ]
[ 123-08-0 ]
[ 117420-31-2 ]

Reference： [1]Journal of Materials Chemistry C,2014,vol. 2,p. 5471 - 5478

80
[ 54550-36-6 ]
7-(5,5-dimethyl-1,3-dioxan-2-yl)-N,N-diphenyl-9H-fluoren-2-amine [ No CAS ]
7-(5,5-dimethyl-1,3-dioxan-2-yl)-9-(2-(2-ethoxyethoxy)ethyl)-N,N-diphenyl-9H-fluoren-2-amine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 10716 - 10725

81
[ 54550-36-6 ]
3-bromo-5-[2-(2-ethoxyethoxy)ethoxy]benzaldehyde [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 1685 - 1688

82
[ 54550-36-6 ]
3-[2-(2-ethoxyethoxy)ethoxy]-5-[2-(trimethylsilyl)ethynyl]benzaldehyde [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 1685 - 1688

83
[ 54550-36-6 ]
{5,15-bis{3-[2-(2-ethoxyethoxy)ethoxy]-5-[2-(trimethylsilyl)ethynyl]phenyl}-10,20-diphehylporphininato}zinc(II) [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 1685 - 1688

84
[ 54550-36-6 ]
[ 626-41-5 ]
1,3-dibromo-5-[2-(2-ethoxyethoxy)ethoxy]benzene [ No CAS ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 1685 - 1688

85
[ 54550-36-6 ]
[ 6674-22-2 ]
C₁₅H₂₉N₂O₂⁽¹⁺⁾*Br^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In ethyl acetate; at 20℃; for 24h;	1,8-diazabicyclo[5.4.0]undec-7-ene(lOmmol) was dissolved in 20 mL of ethyl acetate and slowly added dropwise at room temperature2- (2-ethoxyethoxy) ethyl bromide (lOmmol) was added and the reaction was stirred at room temperature for 24 hours, To generate a transparent liquid.The solvent was removed with a rotary evaporator, washed several times with anhydrous ether, dried under vacuum at 120 C for 24 hours, and the product was liquid at room temperature

Reference： [1]Patent: CN104130263,2016,B .Location in patent: Paragraph 0025-0027

86
[ 101-53-1 ]
[ 54550-36-6 ]
C₁₉H₂₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		A 2-neck round-bottomed flask was charged with acetonitrile (630 milliliters) and potassium carbonate (165 grams, 1.194 moles). The mixture was stirred and 4-benzylphenol (76.5 grams, 415 millimoles) was added. The mixture was heated to reflux under nitrogen for 3 hours, then allowed to cool down. 2-(2-Ethoxyethoxy)ethyl bromide (100 grams, 507 millimoles) and additional acetonitrile (150 milliliters) were added. The mixture was reheated to reflux and maintained for 48 hours. After the reaction mixture was cooled down, it was filtered and the precipitate was washed with methylene chloride. The combined filtrate was concentrated and diluted with methylene chloride. The solution was washed with potassium hydroxide aqueous solution (3 moles/liter), hydrogen chloride solution (3 moles/liter) twice and distilled water sequentially. The organic phase was dried over magnesium sulfate, and evaporated under vacuum to remove the solvent. The crude product was purified by vacuum distillation using a Kugelrohr apparatus. The final product was determined by 1H NMR, 13C NMR and GC. Yields: 86.4 g (69%). 1H NMR (CDCl3): delta 7.27-6.83 (m, 9H, Ph), 3.91 (s, 2H, PhCH2Ph-), 4.10, 3.84, 3.70, 3.61 (t, 2H each, -OCH2CH2OCH2CH2OCH2CH3), 3.53 (q, 2H, -OCH2CH3), 1.21 (t, 3H, -CH3). 13C NMR (CDCl3): delta 157.3, 141.7, 133.6, 130.0, 128.9, 128.5, 126.1, 114.1 (Ph), 71.0, 70.0, 69.9, 67.6, 66.8 (-OCH2CH2OCH2CH2OCH2CH3), 41.2 (PhCH2Ph-), 15.3 (-CH3).

Reference： [1]Patent: US2017/137735,2017,A1 .Location in patent: Paragraph 0164

87
[ 54550-36-6 ]
[ 4105-21-9 ]
3-[2-(2-ethoxyethoxy)ethyl]thio}-2-phenylimidazo[1,2-a]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With N,N,N,N,-tetramethylethylenediamine; sulfur; In acetonitrile; at 100℃; for 24h;	specifically includes the following steps: the above compound of the formula (1a) and the sulfur powder and the compound of the formula (2o) are reacted in a molar ratio of 1:2:3 under the conditions of the alkali TMEDA and the solvent CH3CN, and the molar equivalent of the alkali TMEDA is 1 eq of the compound of formula (1a), wherein the amount of the compound of formula (1a) is 0.2 mmoL and the solvent CH3CN is 2 mL, which is added in turn to a 10 mL reaction tube, and the reaction is stirred at 100 C. for 24 hours; after the reaction is completed, the mixture is cooled and mixed. The solution was diluted with AcOEt and then washed with water. The resulting organic phase was dried over anhydrous sodium sulfate, suction filtered, and the filtrate was removed by rotary evaporation. The residue was subjected to silica gel column chromatography and eluted with petroleum ether/ethyl acetate. TLC test. The product-containing effluent was combined, and the solvent was distilled off on a rotary evaporator and dried in vacuo to give a yellow liquid which was a compound of the formula (22) with a yield of 62%.

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 533 - 543
[2]Patent: CN107759586,2018,A .Location in patent: Paragraph 0132-0135

88
[ 54550-36-6 ]
2-(4-(7-bromo-9,9-bis(2-(2-ethoxyethoxy)ethyl)-9H-fluoren-2-yl)phenyl)ethan-1-ol [ No CAS ]

Reference： [1]Chinese Chemical Letters,2020,vol. 31,p. 119 - 124

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 54550-36-6 ]

Aliphatic Chain Hydrocarbons

[ 957205-14-0 ]

14-Bromo-3,6,9,12-tetraoxatetradecan-1-ol

Similarity: 1.00

[ 57641-66-4 ]

2-(2-Bromoethoxy)ethanol

Similarity: 1.00

[ 72593-77-2 ]

Diethylene Glycol 2-Bromoethyl Methyl Ether

Similarity: 1.00

[ 31255-10-4 ]

1,2-Bis(2-bromoethoxy)ethane

Similarity: 1.00

[ 54149-17-6 ]

1-Bromo-2-(2-methoxyethoxy)ethane

Similarity: 1.00

Bromides

[ 57602-02-5 ]

1,14-Dibromo-3,6,9,12-tetraoxatetradecane

Similarity: 1.00

[ 57641-66-4 ]

2-(2-Bromoethoxy)ethanol

Similarity: 1.00

[ 57641-67-5 ]

2-(2-(2-Bromoethoxy)ethoxy)ethanol

Similarity: 1.00

[ 72593-77-2 ]

Diethylene Glycol 2-Bromoethyl Methyl Ether

Similarity: 1.00

[ 31255-10-4 ]

1,2-Bis(2-bromoethoxy)ethane

Similarity: 1.00

Ethers

[ 57602-02-5 ]

1,14-Dibromo-3,6,9,12-tetraoxatetradecane

Similarity: 1.00

[ 57641-66-4 ]

2-(2-Bromoethoxy)ethanol

Similarity: 1.00

[ 57641-67-5 ]

2-(2-(2-Bromoethoxy)ethoxy)ethanol

Similarity: 1.00

[ 72593-77-2 ]

Diethylene Glycol 2-Bromoethyl Methyl Ether

Similarity: 1.00

[ 31255-10-4 ]

1,2-Bis(2-bromoethoxy)ethane

Similarity: 1.00

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. 54550-36-6 ] {[proInfo.proName]}

Quality Control of [ 54550-36-6 ]

Related Doc. of [ 54550-36-6 ]

Product Details of [ 54550-36-6 ]

Safety of [ 54550-36-6 ]

Application In Synthesis of [ 54550-36-6 ]

[ 54550-36-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 54550-36-6 ]

Aliphatic Chain Hydrocarbons

Bromides

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 54550-36-6 ]