[ CAS No. 57641-66-4 ] {[proInfo.proName]}

Name: 57641-66-4|2-(2-Bromoethoxy)ethanol|95%
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SKU: A210583
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Quality Control of [ 57641-66-4 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 57641-66-4 ]

SDS Specification

Alternatived Products of [ 57641-66-4 ]

Product Details of [ 57641-66-4 ]

CAS No. :	57641-66-4	MDL No. :	MFCD20621572
Formula :	C₄H₉BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JTOJLOUPDKBCCH-UHFFFAOYSA-N
M.W :	169.02	Pubchem ID :	11819432
Synonyms :

Calculated chemistry of [ 57641-66-4 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	31.46
TPSA :	29.46 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) :	-7.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.76
Log Po/w (XLOGP3) :	0.15
Log Po/w (WLOGP) :	0.39
Log Po/w (MLOGP) :	0.42
Log Po/w (SILICOS-IT) :	0.83
Consensus Log Po/w :	0.71

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.72
Solubility :	32.3 mg/ml ; 0.191 mol/l
Class :	Very soluble
Log S (Ali) :	-0.33
Solubility :	79.9 mg/ml ; 0.473 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.51
Solubility :	5.22 mg/ml ; 0.0309 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.32

Safety of [ 57641-66-4 ]

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 [ 57641-66-4 ]

* 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 [ 57641-66-4 ]
Downstream synthetic route of [ 57641-66-4 ]

[ 57641-66-4 ] Synthesis Path-Upstream 1~6

1
[ 107-21-1 ]
[ 106-93-4 ]
[ 123-91-1 ]
[ 57641-67-5 ]
[ 57641-66-4 ]
[ 540-51-2 ]

Reference： [1] Annales de Chimie (Cachan, France), 1863, vol. <3>67, p. 272

2
[ 111-46-6 ]
[ 57641-66-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2014, vol. 53, # 48, p. 13196 - 13200[2] Angew. Chem., 2014, vol. 126, # 48, p. 13412 - 13416,5
[3] Journal of Organic Chemistry, 1993, vol. 58, # 27, p. 7694 - 7699
[4] Journal of Medicinal Chemistry, 2012, vol. 55, # 15, p. 6898 - 6915
[5] Angewandte Chemie - International Edition, 2005, vol. 44, # 34, p. 5480 - 5483
[6] Organic and Biomolecular Chemistry, 2008, vol. 6, # 14, p. 2554 - 2559
[7] Patent: WO2009/94242, 2009, A1, . Location in patent: Page/Page column 33

3
[ 75-21-8 ]
[ 540-51-2 ]
[ 57641-67-5 ]
[ 57641-66-4 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 867
[2] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 865

4
[ 75-21-8 ]
[ 540-51-2 ]
[ 57641-66-4 ]

Reference： [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 25, p. 865

5
[ 107-21-1 ]
[ 106-93-4 ]
[ 57641-66-4 ]

Reference： [1] Annales de Chimie (Cachan, France), 1863, vol. <3>67, p. 272

6
[ 107-21-1 ]
[ 106-93-4 ]
[ 123-91-1 ]
[ 57641-67-5 ]
[ 57641-66-4 ]
[ 540-51-2 ]

Reference： [1] Annales de Chimie (Cachan, France), 1863, vol. <3>67, p. 272

[ 57641-66-4 ] Synthesis Path-Downstream 1~35

1
[ 75-21-8 ]
[ 540-51-2 ]
[ 57641-67-5 ]
[ 57641-66-4 ]

Reference： [1]Patent: DE670419,1936,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 25,p. 865

2
[ 75-21-8 ]
[ 540-51-2 ]
[ 57641-66-4 ]

Reference： [1]Patent: DE670419,1936,
Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 25,p. 865

3
[ 107-21-1 ]
[ 106-93-4 ]
[ 123-91-1 ]
[ 57641-67-5 ]
[ 57641-66-4 ]
[ 540-51-2 ]

Reference： [1]Annales de Chimie (Cachan, France),1863,vol. <3>67,p. 272

4
[ 107-21-1 ]
[ 106-93-4 ]
[ 57641-66-4 ]

Reference： [1]Annales de Chimie (Cachan, France),1863,vol. <3>67,p. 272

5
[ 110-87-2 ]
[ 57641-66-4 ]
2-(2'-bromoethoxy)ethyl 2''-tetrahydropyranyl ether [ No CAS ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 7694 - 7699

6
[ 6362-86-3 ]
[ 57641-66-4 ]
2-<2-(2-bromoethoxy)ethoxy>-4-methyl-1,3,2-dioxaphospholane [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1988,vol. 58,p. 676 - 680
Zhurnal Obshchei Khimii,1988,vol. 58,p. 766 - 770

7
[ 57641-66-4 ]
2-Chloro-3-isopropyl-[1,3,2]oxazaphospholidine [ No CAS ]
2-<2-(2-bromoethoxy)ethoxy>-3-isopropyl-1,3,2-oxazaphospholidine [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1988,vol. 58,p. 676 - 680
Zhurnal Obshchei Khimii,1988,vol. 58,p. 766 - 770

8
[ 57641-66-4 ]
[ 6362-87-4 ]
2-<2-(2-bromoethoxy)ethoxy>-4-methyl-1,3,2-dioxaphosphorinane [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1988,vol. 58,p. 676 - 680
Zhurnal Obshchei Khimii,1988,vol. 58,p. 766 - 770

9
[ 57641-66-4 ]
[ 6362-89-6 ]
2-<2-(2-bromoethoxy)ethoxy>-1,3,2-dioxaphosphorinane [ No CAS ]

Reference： [1]Journal of general chemistry of the USSR,1988,vol. 58,p. 676 - 680
Zhurnal Obshchei Khimii,1988,vol. 58,p. 766 - 770

10
[ 111-46-6 ]
[ 57641-66-4 ]

Yield	Reaction Conditions	Operation in experiment
12%		A solution of 2,2'-oxydiethanol (25 g, 236 mmol) in DCM (250 mL) was treated with triphenylphosphine (30.9 g, 1 18 mmol) and the solution was stirred at room temperature for 30 min. Carbon tetrabromide (39.1 g, 1 18 mmol) was added to the solution dropwise over 60 min. then mixture was stirred at 20 C overnight. The mixture was evaporated and purified by chromatography (silica gel, 0.2-0.33% EtOAc in pet. ether) to afford the desired product (5.0 g; 12%) as a colorless oil. LCMS m/z 192.9 and 190.8 (M+Na)+, 170.9 and 168.8 (M+H)+
	With phosphorus tribromide; at 180℃; for 0.0833333h;Sealed tube; microwave irradiation;	Step A: 2-f2-bromoethoxy)ethanol. Phosphorus tribromide (1.19 mL, 12.6 mmol) was dissolved in diethylene glycol (10.0 mL, 105 mmol) at 0 0C, placed in a sealed tube and heated in a microwave oven at 180 0C for 5 minutes. The mixture was cooled and purified by column chromatography on silica gel, eluting with 0- 100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CDCI3) delta 2.36 (br s, IH), 3.48 (t, J= 6.0 Hz, 2H), 3.61 (t, J- 4.5 Hz, 2H), 3.73 (q, J= 4.5 Hz, 2H), 3.80 (t, J= 6.0 Hz, 2H).

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 13196 - 13200
Angew. Chem.,2014,vol. 126,p. 13412 - 13416,5
[2]Journal of Organic Chemistry,1993,vol. 58,p. 7694 - 7699
[3]Journal of Medicinal Chemistry,2012,vol. 55,p. 6898 - 6915
[4]Angewandte Chemie - International Edition,2005,vol. 44,p. 5480 - 5483
[5]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2554 - 2559
[6]Patent: WO2019/53617,2019,A1 .Location in patent: Page/Page column 177
[7]Patent: WO2009/94242,2009,A1 .Location in patent: Page/Page column 33

11
[ 57641-66-4 ]
[ 125500-66-5 ]
3-butyryl-4-(4-fluoro-2-methylphenylamino)-8-(2-(2-hydroxyethoxy)ethoxy)quinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2748 - 2762

12
[ 57641-66-4 ]
[ 125500-46-1 ]
3-butyryl-4-(2-methylphenylamino)-8-(2-(2-hydroxyethoxy)ethoxy)quinoline [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1995,vol. 38,p. 2748 - 2762

13
[ 57641-66-4 ]
[ 1182-65-6 ]
[ 337954-83-3 ]

Reference： [1]Molecular Crystals and Liquid Crystals Science and Technology, Section A: Molecular Crystals and Liquid Crystals,2002,vol. 381,p. 33 - 41

14
[ 57641-66-4 ]
[ 18162-48-6 ]
(2-(2-bromoethoxy)ethoxy)(tert-butyl)dimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; for 6h;	To a solution of <strong>[57641-66-4]2-(2-bromoethoxy)ethanol</strong> (2.4 g) and teri-butyldimethylchlorosilane (2.4 g) in NN-dimethyl formamide (14.3 mL) was added NN-diisopropylethylamine (6.2 mL), and the reaction was allowed to stir for 6 hours. The reaction was diluted with ethyl acetate, water and brine. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with water then brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was purified by normal phase MPLC on a Teledyne Isco CombiFlash Rf+ 80 g gold silica gel column eluting with 0-15% ethyl acetate in heptanes to give the title compound. NMR (500 MHz, CDC13) delta ppm 3.84-3.80 (m, 2H), 3.79-3.75 (m, 2H), 3.60-3.56 (m, 2H), 3.48-3.43 (m, 2H), 0.90 (s, 9H), 0.07 (s, 6H).

Reference： [1]Angewandte Chemie - International Edition,2005,vol. 44,p. 5480 - 5483
[2]Patent: WO2019/35927,2019,A1 .Location in patent: Paragraph 00913; 00914

15
[ 57641-66-4 ]
[ 4163-65-9 ]
2-[2-(2-bromo-ethoxy)-ethoxy]-O-2',3',4',6'-tetraacetyl-α-D-mannose [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2558 - 2567

16
[ 57641-66-4 ]
[ 4163-60-4 ]
2-[2-(2-bromo-ethoxy)-ethoxy]-O-2',3',4',6'-tetraacetyl-β-D-galactose [ No CAS ]
2-[2-(2-bromo-ethoxy)-ethoxy]-O-2',3',4',6'-tetraacetyl-α-D-galactose [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 2558 - 2567

17
[ 104162-47-2 ]
[ 57641-66-4 ]
[ 1050547-56-2 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2554 - 2559

18
[ 57641-66-4 ]
[ 1050547-47-1 ]
[ 1050547-63-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2554 - 2559

19
[ 57641-66-4 ]
[ 188949-14-6 ]
[ 1050547-65-3 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2554 - 2559

20
[ 57641-66-4 ]
[ 1050547-50-6 ]
[ 1050547-67-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 2554 - 2559

21
[ 371-41-5 ]
[ 57641-66-4 ]
[ 162398-65-4 ]