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Quality Control of [ 10160-87-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 10160-87-9 ]

SDS Specification

Alternatived Products of [ 10160-87-9 ]

Product Details of [ 10160-87-9 ]

CAS No. :	10160-87-9	MDL No. :	MFCD00009237
Formula :	C₇H₁₂O₂	Boiling Point :	No data available
Linear Structure Formula :	HCCCH(OC₂H₅)₂	InChI Key :	RGUXEWWHSQGVRZ-UHFFFAOYSA-N
M.W :	128.17	Pubchem ID :	66285
Synonyms :

Calculated chemistry of [ 10160-87-9 ] Expand+

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.71
Num. rotatable bonds :	4
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.1
TPSA :	18.46 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.28
Log Po/w (XLOGP3) :	0.91
Log Po/w (WLOGP) :	1.1
Log Po/w (MLOGP) :	1.22
Log Po/w (SILICOS-IT) :	1.15
Consensus Log Po/w :	1.33

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.94
Solubility :	14.6 mg/ml ; 0.114 mol/l
Class :	Very soluble
Log S (Ali) :	-0.88
Solubility :	16.8 mg/ml ; 0.131 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.04
Solubility :	11.8 mg/ml ; 0.0918 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.28

Safety of [ 10160-87-9 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P261-P305+P351+P338	UN#:	1993
Hazard Statements:	H225-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 10160-87-9 ]

* 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 [ 10160-87-9 ]

[ 10160-87-9 ] Synthesis Path-Downstream 1~6

1
[ 40263-57-8 ]
[ 10160-87-9 ]
[ 108444-31-1 ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 70℃; for 14h;Inert atmosphere;	A mixture of <strong>[40263-57-8]2-iodo-3-hydroxypyridine</strong> (1 g, 4.5 mmol, 1.0 eq), 3,3-diethoxyprop-1-yne (754.0 mg, 5.9 mmol,1.3 eq), TEA (4.1 g, 41 mmol, 9.0 eq), CuT (172 mg, 905 imol, 0.2 eq) and Pd(PPh3)2C12 (318mg, 453 imol, 0.1 eq) in 10 mL of THF was degassed and purged with N2 three times. The mixture was stirred at 70 C for 14 hours under N2 atmosphere. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography (Si02, eluting with petroleum ether: ethyl acetate = 100:1 to 2:1) to afford 820 mg of 2-(diethoxymethyl)furo[3,2- bjpyridine (3.7 mmol, 82% yield) as yellow oil.
	With copper(l) iodide; triethylamine;bis-triphenylphosphine-palladium(II) chloride; In N,N-dimethyl-formamide; for 17h;	2-Iodo-3-pyridinol (24 mmol), triethylamine (1.0 eq), 3,3-diethoxy-1-propyne (1.0 eq), bis(triphenylphosphine)palladium (II) chloride (0.02 eq), and copper(I) iodide (0.04 eq) were combined in DMF (14 mL) and allowed to stir for 17 hours. The mixture was diluted with ethyl acetate (100 mL) and filtered through a Celite pad. The filtrate was washed with saturated sodium bicarbonate (2*50 mls), dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ 1.28 (t, J=7.1 Hz, 6H), 3.70 (q, J=7.1 Hz, 4H), 5.68 (s, 1H), 7.05 (s, 1H), 7.23 (dd, J=8.5, 4.8 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 8.57 (br, 1H). MS (DCI/NH3) m/z 222 (M+H)+.
	With copper(l) iodide;bis-triphenylphosphine-palladium(II) chloride; for 17h;	[2-IODO-3-PYRIDINOL] (24 mmol), triethylamine (1.0 [EQ),] 3, [3-DIETHOXY-1-PROPYNE] (1.0 eq), bis (triphenylphosphine) palladium [(II)] chloride (0.02 [EQ),] and copper [(I)] iodide (0.04 eq) were combined in DMF (14 mL) and allowed to stir for 17 hours. The mixture was diluted with ethyl acetate (100 mL) and filtered through a Celite pad. The filtrate was washed with saturated sodium bicarbonate (2x50mls), dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further [PURIFICATION.'H] NMR [(CDC13,] [400MHZ)] [5] 1.28 (t, J=7. [1HZ,] 6H), 3.70 (q, J=7. [1HZ,] 4H), 5.68 (s, 1H), 7.05 (s, [1H),] 7.23 (dd, J=8.5, 4.8Hz, [1H),] 7.77 (d, J=8. 5Hz, 1H), 8.57 (br, 1H). MS (DCI/NH3) [M/Z] 222 (M+H) [+.]

Reference： [1]Synthesis,1986,p. 749 - 751
[2]Patent: WO2018/119395,2018,A1 .Location in patent: Page/Page column 184
[3]Patent: US2006/172995,2006,A1 .Location in patent: Page/Page column 56
[4]Patent: WO2003/101994,2003,A1 .Location in patent: Page 92-93

2
[ 10160-87-9 ]
[ 211029-67-3 ]
[ 853685-76-4 ]

Yield	Reaction Conditions	Operation in experiment
		2-(Diethoxymethyl)-1H-pyrrolo[3,2-c]pyridine-1-carboxylic acid 1,1-dimethylethyl ester, 8b-1 (Scheme 3, step h) Heat a solution of (3-iodo-pyridin-4-yl)carbamic acid 1,1-dimethylethyl ester (13.3 g, 41.56 mmol, Darnbrough, Shelley; Mervic, Miljenko; Condon, Stephen M.; Burns, Christopher J. Synthetic Communications (2001) 31(21), 3273-3280), 3,3-diethoxy-1-propyne (5.96 ml, 41.56 mmole), triethylamine (23 ml, 166 mmol), dichlorobis(triphenyl-phospine)palladium(II) (1.46 g, 2.08 mmol) and copper iodide (237 mg, 1.25 mmol) in dry DMF under argon to 90 C. for 3 h. Allow the reaction mixture to cool to 70 C. and add DBU (12.5 ml, 83.12 mmol). Stir the reaction at 70 C. for 3 h and then stir at room temperature overnight. Pour the reaction mixture into EtOAc, wash with water (2*) and brine, dry over MgSO4, filter and concentrate to give the title compound as an oil. Purify the oil by flash chromatography (silica, elute with 10-20% EtOAc/n-heptane) to provide 9.8 g of the title compound as a clear oil, tlc (silica, 30% EtOAc/heptane, Rf=0.30).

Reference： [1]Patent: US2005/131012,2005,A1 .Location in patent: Page/Page column 11; 20

3
[ 40263-57-8 ]
bis(triphenylphosphine)palladium(II) dichloride [ No CAS ]
[ 10160-87-9 ]
[ 108444-31-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;copper(I) iodide; In N,N-dimethyl-formamide;	EXAMPLE 35a 2-(diethoxymethyl)furo[3,2-b]pyridine 2-Iodo-3-pyridinol (24 mmol), triethylamine (1.0 eq), 3,3-diethoxy-1-propyne (1.0 eq), bis(triphenylphosphine)palladium (II) chloride (0.02 eq), and copper(I) iodide (0.04 eq) were combined in DMF (14 mL) and allowed to stir for 17 hours. The mixture was diluted with ethyl acetate (100 mL) and filtered through a Celite pad. The filtrate was washed with saturated sodium bicarbonate (2*50 mls), dried over anhydrous magnesium sulfate, filtered, and the filtrate concentrated under reduced pressure to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) δ1.28 (t, J=7.1 Hz, 6H), 3.70 (q, J=7.1 Hz, 4H), 5.68 (s, 1H), 7.05 (s, 1H), 7.23 (dd, J=8.5, 4.8 Hz, 1H), 7.77 (d, J=8.5 Hz, 1H), 8.57 (br, 1H). MS (DCI/NH3) m/z 222 (M+H)+.

Reference： [1]Patent: US2004/2488,2004,A1

4
[ 10160-87-9 ]
[ 6214-35-3 ]
[ 1188414-01-8 ]

Yield	Reaction Conditions	Operation in experiment
75%	With copper(l) iodide; palladium 10% on activated carbon; triethylamine; triphenylphosphine; In 1,4-dioxane; at 25 - 80℃; for 3.5h;Inert atmosphere;	General procedure: (a) The reaction was performed in a bigger scale using 100 mg of 10% Pd/C (0.092 mmol), PPh3 (0.37 mmol), CuI (0.184 mmol), Et3N (10.68 mmol), compound 1a (3.56 mmol), and acetylenic compound 2a (5.32 mmol) in 1,4-dioxane (20.0 mL). After stirring at 80 C for 3 h under nitrogen the mixture was cooled to room temperature. The Pd/C was filtered off and washed with water (2 10 mL), acetone (2 10 mL), and EtOAc (2 10 mL). Then the catalyst was collected, dried at 100 C in an oven, and reused for the next run. The co-catalyst CuI along with PPh3 was added in every repeated run. (b) General method for the preparation of 3: A mixture of compound 1 (0.89 mmol), 10% Pd/C (0.023 mmol), PPh3 (0.092 mmol), CuI (0.046 mmol), and Et3N (2.67 mmol) in 1,4-dioxane (5.0 mL) was stirred at 25 C for 30 min under nitrogen. The acetylenic compound 2 (1.33 mmol) was added slowly with stirring. The mixture was then stirred at 80 C for 3 h, cooled to room temperature, diluted with EtOAc (30 mL), and filtered through celite. The filtrate was collected and concentrated. The residue was purified by column chromatography (2-15% EtOAc/hexane) to afford the desired product

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 2151 - 2155
[2]Advanced Synthesis and Catalysis,2009,vol. 351,p. 779 - 788

5
[ 10160-87-9 ]
[ 4181-20-8 ]
C₃₉H₄₅NO₆ [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2015,vol. 3,p. 7345 - 7355

6
[ 10160-87-9 ]
[ 2296-23-3 ]
3-(3,3-diethoxyprop-1-yn-1-yl)-4-hydroxybenzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;	Reference Example 33-1 3-(3,3-Diethoxyprop-1-yn-1-yl)-4-hydroxybenzonitrile In a nitrogen atmosphere, <strong>[2296-23-3]4-hydroxy-3-iodobenzonitrile</strong> (600 mg, 2.5 mmol), 3,3-diethoxypropyne (388 muL, 2.7 mmol), triethylamine (374 muL, 2.7 mmol), copper(I) iodide (19 mg, 0.10 mmol), and bis(triphenylphosphine)palladium (II) dichloride (34 mg, 0.048 mmol) were dissolved in DMF (2.5 mL), and the solution was stirred for 16 hours at room temperature. Water was added to the reaction liquid, the mixture was stirred for a while, and then the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and was dried over anhydrous sodium sulfate. Insoluble materials were filtered, and then the solvent was distilled off under reduced pressure. A residue thus obtained was purified by silica gel column chromatography (hexane:ethyl acetate) (concentration gradient: 29% to 50%), and thus the title compound (brown oily material, 356 mg, 59%) was obtained. 1H NMR(CDCl3, 400MHz):delta=1.28(t, 6H, J=7Hz), 3.6-3.8(m, 4H), 5.67(s, 1H), 6.87(s, 1H), 7.57(s, 2H), 7.9-8.0(m, 1H).

Reference： [1]Patent: EP3404021,2018,A1 .Location in patent: Paragraph 0194

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