5471-84-1|1,4-Bis(2-bromoethoxy)benzene| Ambeed

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Structure of 1,4-Bis(2-bromoethoxy)benzene
CAS No.: 5471-84-1

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Quality Control of [ 5471-84-1 ] Purity: 98% SDS Specification

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Product Details of [ 5471-84-1 ]

CAS No. :	5471-84-1
Formula :	C₁₀H₁₂Br₂O₂
M.W :	324.01
SMILES Code :	BrCCOC1=CC=C(OCCBr)C=C1
MDL No. :	MFCD14705063
InChI Key :	ATALLSGKFZVRKF-UHFFFAOYSA-N
Pubchem ID :	231758

Safety of [ 5471-84-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H311-H331-H341
Precautionary Statements:	P201-P202-P261-P264-P270-P271-P280-P302+P352-P304+P340-P308+P313-P310-P330-P361-P403+P233-P405-P501
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 5471-84-1 ]

* 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.

Downstream synthetic route of [ 5471-84-1 ]

[ 5471-84-1 ] Synthesis Path-Downstream 1~35

1
[ 110-89-4 ]
[ 5471-84-1 ]
1,4-bis-(2-piperidino-ethoxy)-benzene [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1943,vol. 63,p. 387,389.
Chem.Abstr.,1951,p. 3350.

2
[ 106-93-4 ]
[ 123-31-9 ]
[ 5471-84-1 ]

Yield	Reaction Conditions	Operation in experiment
21%	With potassium carbonate; In acetone; for 24h;Inert atmosphere; Reflux;	Hydroquinone (10.0g, 91mmol), 1,2-dibromoethane (35mL, 0.41mol) and potassium carbonate (40g, 0.29mol) were added into acetone (150mL), the mixture was refluxed for 24h under N2. After the reaction mixture was cooled down to room temperature, precipitate was removed by filtration. The solvent was removed under reduced pressure and the product was purified by column chromatography (eluent: hexane: dichloromethane=1:1). A white solid was obtained (6.3g, 21%). 1H NMR (400MHz, CDCl3): δ 6.86 (s, 4H), 4.24 (t, 4H, J=6.3Hz), 3.61 (t, 4H, J=6.3Hz). 13C NMR (101MHz, CDCl3): δ 152.81, 116.07, 77.36, 77.04, 76.72, 68.69, 29.30.

References: [1]Organometallics,2011,vol. 30,p. 3732 - 3739.
[2]Chemical Communications,2018,vol. 54,p. 12646 - 12649.
[3]Chinese Chemical Letters,2016,vol. 27,p. 1017 - 1021.
[4]Chemical Communications,2018,vol. 54,p. 12990 - 12993.
[5]Journal of the American Chemical Society,1941,vol. 63,p. 2073,2076, 2077.

3
[ 5471-84-1 ]
[ 109-89-7 ]
[ 106631-39-4 ]

References: [1]Chemistry - A European Journal,2018,vol. 24,p. 15750 - 15755.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1943,vol. 63,p. 387,389.
Chem.Abstr.,1951,p. 3350.

4
[ 104-38-1 ]
[ 5471-84-1 ]

Yield	Reaction Conditions	Operation in experiment
85%	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 20℃; for 4h;Inert atmosphere;	While stirring at 0 C, carbontetrabromide (39.8 g, 120mmol) was slowly added to the dissolved1,4-bis(2-hydroxyethoxy)benzene (10.0 g, 50.4mmol)and triphenylphosphine (31.5 g, 120mmol) in 300mL driedacetonitrile. The clear solution obtained after the reactionmixture was heated to room temperature under the protection ofinert nitrogen was stirred for another 4 h. Then 200mL of coldwater was added to the reaction mixture to obtain a white solid.The white solid was collected by vacuum filtration, washedthoroughly with a 60:40 mixed solvent of V methanol: V water,and recrystallized from methanol to obtain white flake crystals.After vacuum drying, product 1 (13.8 g, 85%) was obtained.
83.4%	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 20℃; for 4h;	The first step is the preparation of the compound (I), i.e., 1,4-bis (2-bromoethoxy) benzene:First of all,Hydroquinone dihydroxyethyl ether (10.0 g, 50 mmol),Triphenylphosphine (31.5 g, 120.0 mmol)And solvent acetonitrile (200 g, 250 mL)Was added to a 500 mL three-necked flask,The reaction system was then placed in an ice bath until the temperature of the reaction system was 0 C,Stir well at 0 C,And then dropping carbon tetrabromide (39.8 g, 120.0 mmol)After completion of the dropwise addition, the reaction system was taken out from the ice bath and naturally slowly raised to room temperature,The reaction system gradually clarifies,Continue to stir 4h,After the reaction system was turned into a suspension,After adding cold water (200 g, 200 mL) to the reaction system,White precipitate appeared in the reaction system,After filtration, the precipitate was obtained,The filtered precipitate was washed three times with 100 mL of a solution (methanol in the solution: water (V / V) = 3: 2)To give the compound (I), i.e., 1,4-bis (2-bromoethoxy) benzene,Finally, the crude product of compound (I) was recrystallized by the methanol recrystallization method,To obtain 13.6 g of the higher purity compound (I)For small white crystals.The yield of the compound (I) was 83.4%
82.7%	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 20℃; for 12h;Inert atmosphere; Cooling with ice;	A solution of 4-bis(2-hydroxyethoxy) benzene (6.0 g 30 mmol) and triphenylphosphine (18.9 g,72.1 mmol) in dry acetonitrile (200 mL) was cooled with an ice bath. Under vigorous stirring, carbon tetrabromide (24.0 g, 72.4 mmol) was slowly added. The mixture was stirred at room temperature for 12 hours. Then cold water (200 mL) was added to the reaction mixture to give white precipitation. The precipitate was collected, washed with methanol/water (3:2, 3 × 100 mL), recrystallized from methanol, and dried under vacuum to afford 1 as white crystals, 82.7% (14.5 g, 24.8mmol).

82.7%	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20℃; for 12h;Cooling with ice;	A solution of 4-bis(2-hydroxyethoxy) benzene (6.0 g,30 mmol) and triphenylphosphine (18.9 g, 72.1 mmol) indry acetonitrile (200 mL) was cooled with an ice bath.Under vigorous stirring, carbon tetrabromide (24.0 g,72.4 mmol) was slowly added. The mixture was stirred atroom temperature for 12 h. Then cold water (200 mL) wasadded to the reaction mixture to give white precipitation. The precipitate was collected, washed with methanol/water(3:2, 3 9 100 mL), recrystallized from methanol, anddried under vacuum to afford 1 as white crystals, 82.7%(14.5 g). 1H NMR (600 MHz, CDCl3): d = 6.86 (s, 4H),4.24 (t, J = 6.3, 4H), 3.61 (t, J = 6.3, 4H) ppm.
80%		1,4-Bis(hydroxyethoxy)benzene (5.00 g, 25.2 mmol) andtriphenylphosphine (15.00 g, 60 mmol) were stirred inCH3CN and cooled to 0 C. Carbon tetrabromide (20.00 g,60 mmol) was slowly added in small portions to a solutionwith stirring while maintaining 0 C. The reaction mixturewas then left to warm to room temperature and theresulting clear solution was stirred for a further 4 h undera nitrogen atmosphere. Cold distilled water (100 ml) wasadded to precipitate a white solid that was collected byvacuum filtration and recrystallised from hot methanol(200 mL). 1,4-Bis(bromoethoxy)benzene was isolated aswhite flake-like crystals following vacuum filtration. Yield:6.54 g (80%); m.p.: 112.7-115.6 C; 1H NMR (400 MHz,CDCl3) δ (ppm): 6.85 (s, 4H, ArH), 4.23 (t, 4H, -CH2O), 3.59(t, 4H, -CH2Br); 13C NMR (90 MHz, CDCl3) δ (ppm): 152.89,116.17, 68.81, 29.19. HRMS (m/z): calcd for C10H12Br2O2·NaC2HO2, 391.9063; found, 391.9195. Note: the molecular ioncould not be detected for this compound and was alwaysobserved as the sodium orthoformate complex.
79.2%	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 20℃; for 24h;	Add hydroquinone dihydroxy ether and triphenylphosphine to acetonitrile (or acetone) in a molar ratio of 1:3, At 0C, add carbon tetrabromide in batches (the molar ratio of hydroquinone dihydroxy ether to carbon tetrabromide is 1:3), and continue stirring for 24h at room temperature It is quenched by adding deionized water, filtered, washed, and separated by column chromatography to obtain 1,4-bis(2-bromoethoxy)benzene as a white powder. It is also possible to add deionized water to quench the reaction, filter with suction and wash with a mixed solution of methanol and water to obtain 1,4-bis(2-bromoethoxy)benzene.
	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 25℃; for 4h;Inert atmosphere;	In a round bottom flask (500 mL), 1,4-di(2-hydroxyethoxy)benzene (5 g, 25 mmol) and triphenylphosphine (15.7 g, 60 mmol) were weighed and dissolved in anhydrous acetonitrile (120 mL), then, while maintaining the temperature at 0 C, carbon tetrabromide (19.9 g, 60 mmol) was slowly added to the above system. Then, the temperature was raised to room temperature at 25 C, and stirred under nitrogen for 4 hours. After completion of the reaction, ice-water (200mL) was added to the system, the product was precipitated, the solid was obtained by filtration and washed 3-4 times with methanol/water (3:2, 3×100 mL), and the crude product was recrystallized from methanol for further purification to give a pure product
	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 0 - 25℃; for 4h;Inert atmosphere;	In a round bottom flask (500 mL), 1,4-bis(2-hydroxyethoxy)benzene (5 g, 25 mmol) and triphenylphosphine (15.7 g, 60 mmol) were weighed and dissolved in anhydrous acetonitrile (120 mL) Then, while maintaining the temperature at 0 C, carbon tetrabromide (19.9 g, 60 mmol) was slowly added to the above system. Then, the temperature was raised to room temperature at 25 C, and stirred under nitrogen for 4 hours. After completion of the reaction, ice water (200 mL) was added to the system to precipitate a product. The solid was obtained by filtration and washed 3-4 times with methanol/water (3:2, 3×100 mL). The crude product was recrystallized from methanol for further purification to give a pure product.
14.5 g	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20℃; for 4h;Cooling with ice;	(1) 10 g of hydroquinone di(2-hydroxyethyl)ether, 31.5 g of triphenylphosphine, and 250 mL of anhydrous acetonitrile were sequentially placed in a round bottom flask.After cooling with an ice water bath, and stirring and stirring, 39.8 g of carbon tetrabromide was added, and the reaction was stirred at room temperature for 4 hours.After the reaction was completed, 200 mL of cold water was added to the mixture to quench the reaction to obtain a white precipitate, which was collected by filtration.It was washed 3 times with an aqueous methanol solution (volume ratio of 3:2), recrystallized from methanol, and dried, white crystals, 14.5 g,
	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20℃; for 4h;	General procedure: Synthesis of tetramer and the following substances according to previously reported procedures.1-3 The raw material 1 (10 g, 50.4 mmol) was added to MeCN (250 ml) under ice bath and then stirred for a few minutes to dissolve the raw material. Triphenylphosphine (31.5 g, 120 mmol) continues to be added to the mixture and stirred for a few minutes. Then, slowly add dropwise carbon tetrabromide (39.8 g, 120 mmol) to the reaction solution, and after stirring for a while, the ice bath is removed and stirred at room temperature for 4 h. The addition of 200 ml water resulted in a precipitate. The precipitate washed by MeOH/H2O (100 ml2, V: V=3:2). Finally wash with methanol (70 ml2) to obtain product 2 as a white solid. The tetramer (3.24 g, 4.15 mmol) was dissolved in trifluoroacetate (35 ml), followed by adding the product 2 (4.59 g, 14.17 mmol). The mixture was stirred for 3 h at 70 after removal of the trifluoroacetate by distillation under reduced pressure. The obtained solid was washed with methanol (300 ml) and acetone (400 ml). The product 3 was obtained as a white solid by vacuum drying (3.52 g, 82%). 1H NMR (600 MHz, DMSO): 6.91 (s, 4H), 5.59 (d, J = 14.4, 2H), 5.51 (d, J = 15.2, 4H), 5.38 (d, J = 9.0, 2H),5.30-5.25 (m, 6H), 4.50-4.40 (m, 4H), 4.25-4.20 (m, 10H), 4.06 (d, J = 15.2, 4H), 3.90-3.80(m, 8H), 1.69 (s, 6H), 1.66 (s, 6H). The product 3 (3.5 g, 2.51 mmol) was dissolved in DMSO (35 ml), followed by adding sodium azide (1.96 g, 30.15 mmol). The mixture was stirred for 12 h at 80. Then pour the reaction solution into water to obtain a precipitate. The precipitate was washed with methanol (350 ml) to obtain product 4 as a white solid (3.10 g, 97%). 1H NMR (600 MHz, DMSO): 6.88 (s, 4H), 5.57 (d,J = 14.6, 2H), 5.47 (d, J = 15.1, 4H), 5.37 (d, J = 8.7, 2H), 5.25 (d, J = 8.7, 2H), 5.24 (d, J =16.1, 4H), 4.25 - 4.20 (m, 4H), 4.14 (d, J = 16.1, 4H), 4.15 - 4.05 (m, 4H), 4.05 (d, J = 14.6,4H), 4.03 (d, J = 15.1, 2H), 3.85-3.75 (m, 4H), 3.55-3.45 (m, 4H), 1.69 (s, 6H), 1.66 (s, 6H). The product 4 (2.5 g, 2.01 mmol) was dissolved in mixed solvent of DMSO and H2O (80 ml and 8 ml), followed by adding triphenylphosphine (4.18 g, 15.94 mmol). The mixture was stirred for 6 h at 80. The reaction solution was adjusted to pH 1 with HCl (6 mol), and then the reaction solution was poured into acetone (400 ml) to obtain a white precipitate. The white precipitate was washed with acetone (300 ml). The white precipitate was dissolved with a minimum amount of water and then acetone (120 ml) was added to obtain a white precipitate which was repeated twice to give a host-2 as a white solid (1.23g, 43%). 1H NMR (600 MHz, D2O): 6.44 (s, 4H),5.58 (d, J = 15.3, 2H), 5.52 (d, J = 15.8, 4H), 5.46 (d, J = 9.2, 2H), 5.28 (d, J = 9.2, 2H), 5.27(d, J = 16.5, 4H), 4.31 (d, J = 15.8, 4H), 4.29 (d, J = 16.5, 4H), 4.13 (d, J = 15.3, 2H), 3.85 -3.75 (m, 4H), 3.65-3.55 (m, 4H), 3.350-3.10 (m, 8H), 1.78 (s, 6H), 1.77 (s, 6H).
	With carbon tetrabromide; triphenylphosphine; In acetonitrile; at 20℃; for 4h;	Add hydroquinone bis(2-hydroxyethyl) ether (1.98 g, 0.01 mol), after the hydroquinone bis(2-hydroxyethyl) ether is completely dissolved, add carbon tetrabromide (13.24 g, 0.04 mol), triphenylphosphine (5.24 g, 0.02 mol), the reaction solution was reacted at room temperature for 4 h. After the reaction is over, add pure water (200 mL) to the reaction solution In the process, a white precipitate is produced, and the precipitate is vacuum filtered to obtain a crude product; the crude product is washed 3 times with methanol/water (volume ratio 3:2), each After 100 mL, the pure product is obtained. Dry in a vacuum drying oven to obtain a white solid, and finally prepare bromobenzene ring side arms

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5
[ 553-26-4 ]
[ 5471-84-1 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2Br^(1-) [ No CAS ]

References: [1]Chemistry - A European Journal,1997,vol. 3,p. 788 - 798.

6
[ 53914-95-7 ]
[ 5471-84-1 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
C₄₀H₄₀N₄O₄⁽⁴⁺⁾*2C₂₈H₄₀O₁₀*2Br^(1-)*2F₆P^(1-) [ No CAS ]

References: [1]Chemistry - A European Journal,1997,vol. 3,p. 788 - 798.

7
[ 5471-84-1 ]
[ 116059-04-2 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
C₄₀H₄₀N₄O₄⁽⁴⁺⁾*2C₃₆H₄₄O₁₀*2Br^(1-)*2F₆P^(1-) [ No CAS ]

References: [1]Chemistry - A European Journal,1997,vol. 3,p. 788 - 798.

8
[ 5471-84-1 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
[ 180137-04-6 ]
C₄₀H₄₀N₄O₄⁽⁴⁺⁾*2C₂₈H₃₆F₄O₁₀*2Br^(1-)*2F₆P^(1-) [ No CAS ]

References: [1]Chemistry - A European Journal,1997,vol. 3,p. 788 - 798.

9
[ 5471-84-1 ]
[ 2150-02-9 ]
2,8,14-Trioxa-5,11-dithia-bicyclo[13.2.2]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene [ No CAS ]
2,8,14,19,25,31-Hexaoxa-5,11,22,28-tetrathia-tricyclo[30.2.2.2^15,18]octatriaconta-1⁽³⁵⁾,15⁽³⁸⁾,16,18⁽³⁷⁾,32⁽³⁶⁾,33-hexaene [ No CAS ]

References: [1]Chemistry - A European Journal,1997,vol. 3,p. 772 - 787.

10
[ 5471-84-1 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
C₄₀H₄₀N₄O₄⁽⁴⁺⁾ [ No CAS ]

References: [1]European Journal of Organic Chemistry,1998,p. 969 - 981.

11
[ 5471-84-1 ]
1,3-bis(2-(4,4'-dipyridinium)ethoxy)benzene dihexafluorophosphate [ No CAS ]
C₄₀H₄₀N₄O₄⁽⁴⁺⁾ [ No CAS ]

References: [1]European Journal of Organic Chemistry,1998,p. 969 - 981.

12
[ 5471-84-1 ]
C₃₄H₃₀N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
C₄₄H₄₂N₄O₄⁽⁴⁺⁾ [ No CAS ]

References: [1]European Journal of Organic Chemistry,1998,p. 969 - 981.

13
[ 5471-84-1 ]
[ 116059-04-2 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
C₃₆H₄₄O₁₀*C₃₆H₄₄O₁₀*C₄₀H₄₀N₄O₄⁽⁴⁺⁾*4PF₆^(1-) [ No CAS ]

References: [1]European Journal of Organic Chemistry,2000,p. 1121 - 1130.

14
[ 5471-84-1 ]
[ 158394-28-6 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
C₅₄H₆₆O₁₅*C₅₄H₆₆O₁₅*C₄₀H₄₀N₄O₄⁽⁴⁺⁾*4PF₆^(1-) [ No CAS ]

References: [1]European Journal of Organic Chemistry,2000,p. 1121 - 1130.

15
[ 5471-84-1 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]
tetra-1,5-naphtho-76-crown-20 [ No CAS ]
C₇₂H₈₈O₂₀*C₄₀H₄₀N₄O₄⁽⁴⁺⁾*4F₆P^(1-) [ No CAS ]

References: [1]European Journal of Organic Chemistry,2000,p. 1121 - 1130.

16
[ 5471-84-1 ]
C₃₀H₂₈N₄O₂⁽²⁺⁾*2F₆P^(1-) [ No CAS ]

References: [1]Chemistry - A European Journal,1997,vol. 3,p. 788 - 798.

17
[ 5471-84-1 ]
[ 121619-22-5 ]
[ 167647-23-6 ]

References: [1]Monatshefte fur Chemie,2008,vol. 139,p. 639 - 645.

18
[ 5471-84-1 ]
[ 150899-11-9 ]
1,4,8,11-tetra(2-bromoethoxy)-13b,13c-dimethyl-5,7,12,13b,13c,14-hexahydro-5a,6a,12a,13a-tetraazabenzo[5,6]azuleno[2,1,8-ija]benzo[f]azulene-6,13-dione [ No CAS ]

References: [1]Monatshefte fur Chemie,2008,vol. 139,p. 639 - 645.

19
[ 5471-84-1 ]
1,4-bis[1-(n-butyl)benzimidazoliumylethoxy]benzene hexafluorophosphate [ No CAS ]

References: [1]Organometallics,2011,vol. 30,p. 3732 - 3739.

20
[ 5471-84-1 ]
1,4-diiodo-2,5-bis-(2-bromoethoxy)benzene [ No CAS ]