[ CAS No. 104-38-1 ] {[proInfo.proName]}

Name: 104-38-1|1,4-Bis(2-hydroxyethoxy)benzene|95%
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3d Animation Molecule Structure of 104-38-1

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Quality Control of [ 104-38-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 104-38-1 ]

SDS Specification

Alternatived Products of [ 104-38-1 ]

Product Details of [ 104-38-1 ]

CAS No. :	104-38-1	MDL No. :	MFCD00002861
Formula :	C₁₀H₁₄O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WTPYFJNYAMXZJG-UHFFFAOYSA-N
M.W :	198.22	Pubchem ID :	66912
Synonyms :

Calculated chemistry of [ 104-38-1 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	6
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	51.36
TPSA :	58.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-7.19 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.01
Log Po/w (XLOGP3) :	0.45
Log Po/w (WLOGP) :	0.43
Log Po/w (MLOGP) :	0.37
Log Po/w (SILICOS-IT) :	1.31
Consensus Log Po/w :	0.91

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.27
Solubility :	10.6 mg/ml ; 0.0533 mol/l
Class :	Very soluble
Log S (Ali) :	-1.26
Solubility :	11.0 mg/ml ; 0.0555 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.35
Solubility :	0.881 mg/ml ; 0.00445 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.55

Safety of [ 104-38-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P273-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H412	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 104-38-1 ]

* 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 [ 104-38-1 ]
Downstream synthetic route of [ 104-38-1 ]

[ 104-38-1 ] Synthesis Path-Upstream 1~1

1
[ 104-38-1 ]
[ 81926-24-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 6, p. 1003 - 1010

[ 104-38-1 ] Synthesis Path-Downstream 1~87

1
[ 141-97-9 ]
[ 104-38-1 ]
[ 98682-96-3 ]

Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 5777 - 5779

2
[ 104-38-1 ]
[ 5471-84-1 ]

Yield	Reaction Conditions	Operation in experiment
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) delta (ppm): 6.85 (s, 4H, ArH), 4.23 (t, 4H, -CH2O), 3.59(t, 4H, -CH2Br); 13C NMR (90 MHz, CDCl3) delta (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.
	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), <strong>[104-38-1]1,4-bis(2-hydroxyethoxy)benzene</strong> (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).

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3
[ 67-56-1 ]
[ 104-38-1 ]
[ 55426-93-2 ]

Reference： [1]Tetrahedron Letters,1988,vol. 29,p. 163 - 166

4
[ 134940-43-5 ]
[ 104-38-1 ]
[ 134881-64-4 ]

Reference： [1]Angewandte Chemie,1991,vol. 103,p. 1058 - 1061

5
[ 124-63-0 ]
[ 104-38-1 ]
[ 133633-40-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 3454 - 3457
[2]Tetrahedron Letters,2006,vol. 47,p. 3095 - 3098
[3]Chemistry - A European Journal,2011,vol. 17,p. 816 - 825
[4]European Journal of Inorganic Chemistry,2011,p. 479 - 488
[5]Organic Letters,2018,vol. 20,p. 4745 - 4748

6
[ 104-38-1 ]
[ 98-59-9 ]
[ 943857-84-9 ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 543 - 575
[2]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 4587 - 4594
[4]Chemical Communications,2014,vol. 50,p. 1540 - 1542

7
[ 104-38-1 ]
C₇₂H₈₄N₂O₁₀ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870

8
[ 104-38-1 ]
C₇₂H₈₃N₃O₁₂ [ No CAS ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870

9
[ 104-38-1 ]
[ 943857-85-0 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870
[2]Chemical Communications,2014,vol. 50,p. 1540 - 1542

10
[ 104-38-1 ]
[ 943857-83-8 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870
[2]Chemical Communications,2014,vol. 50,p. 1540 - 1542

11
[ 104-38-1 ]
[ 943857-86-1 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870

12
[ 104-38-1 ]
[ 943857-87-2 ]

Reference： [1]Chemistry - A European Journal,2007,vol. 13,p. 3861 - 3870

13
[ 104-38-1 ]
[ 888721-91-3 ]

Yield	Reaction Conditions	Operation in experiment
87%	With carbon tetraiodide; triphenylphosphine; In acetonitrile; at 0 - 20℃; for 3h;Inert atmosphere;	Carbon tetraiodide (12.24 g, 24 mmol) was slowly added in small portions to a solution of <strong>[104-38-1]1,4-bis(2-hydroxyethoxy)benzene</strong> (1) (2.38 g, 12 mmol) and triphenylphosphine (6.30 g, 12 mmol) in 100 mL of dry acetonitrile at 0 C. Then, the reaction mixture was stirred at room temperature, and the resulting clear solution was stirred for another 3 h under Ar. 100 g of ice was added to the reaction mixture, where 1,4-bis(2-iodoethoxy)benzene slowly precipitated as a white solid. The product was collected by vacuum filtration, thoroughly washed with cold methanol/water, 60:40. The white flake-like crystals were dried in desiccator (4.37 g, 87 %). M.P.: 92 oC. 1H-NMR (400 MHz, chloroform-d, room temperature) delta (ppm): 6.92 (s, 4H), 4.33 (t, J = 5.2 Hz, 4H), 3.52 (t, J = 5.7 Hz, 4H). 13C-NMR (100 MHz) delta (ppm): 150.38, 116.10, 75.18, 4.32.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 1958 - 1962
[2]Medicinal Chemistry Research,2020,vol. 29,p. 1077 - 1083
[3]Tetrahedron Letters,2006,vol. 47,p. 3095 - 3098

14
[ 104-38-1 ]
[ 888721-95-7 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3095 - 3098

15
[ 104-38-1 ]
4,4'-(1,4-phenylenedioxo)bis[2-(dimethylsulfanylidene)butanal] [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3095 - 3098

16
[ 104-38-1 ]
4,4'-(1,4-phenylenedioxo)bis[2-(methylthio)butanal] bis(N,N-dimethylhydrazone) [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 3095 - 3098

17
[ 104-38-1 ]
[ 819805-54-4 ]

Reference： [1]Chemistry Letters,2004,vol. 33,p. 1418 - 1419

18
[ 104-38-1 ]
[ 847050-59-3 ]

Reference： [1]Dalton Transactions,2005,p. 359 - 364

19
[ 104-38-1 ]
[ 577993-09-0 ]

Reference： [1]Chemistry Letters,2003,vol. 32,p. 516 - 517

20
[ 104-38-1 ]
[ 81926-24-1 ]