104190-22-9|1-(2-Ethynylphenyl)ethanone| Ambeed

CAS No. :	104190-22-9
Formula :	C₁₀H₈O
M.W :	144.17
SMILES Code :	CC(C1=CC=CC=C1C#C)=O
MDL No. :	MFCD18207358
InChI Key :	YQXSJPABBZMARN-UHFFFAOYSA-N
Pubchem ID :	582213

Safety of [ 104190-22-9 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H312-H332
Precautionary Statements:	P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P403+P233-P501

Application In Synthesis of [ 104190-22-9 ]

* 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 [ 104190-22-9 ]

[ 104190-22-9 ] Synthesis Path-Downstream 1~54

1
[ 104190-22-9 ]
[ 153093-72-2 ]

References: [1]Liebigs Annalen der Chemie,1993,p. 1009 - 1016.
[2]Journal of Organic Chemistry,2018,vol. 83,p. 7799 - 7813.
[3]Advanced Synthesis and Catalysis,2021,vol. 363,p. 4024 - 4032.

2
[ 69739-34-0 ]
[ 104190-22-9 ]
tert-Butyl-[1-(2-ethynyl-phenyl)-vinyloxy]-dimethyl-silane [ No CAS ]

References: [1]Tetrahedron Letters,2001,vol. 42,p. 5809 - 5812.

3
[ 111-34-2 ]
[ 104190-22-9 ]
(+/-)-(1RS,3SR,3aSR,5SR,9bSR)-3,5-methano-5-methyl-1-propyl-1,3,3a,9b-tetrahydrofuro[3,4-c]isochromene [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2709 - 2716.
[2]Journal of the American Chemical Society,2001,vol. 123,p. 5814 - 5815.

4
[ 2678-54-8 ]
[ 104190-22-9 ]
(+/-)-(1RS,3SR,3aSR,5SR,9bSR)-1,5-dimethyl-3-ethoxy-3,5-methano-1,3,3a,9b-tetrahydrofuro[3,4-c]isochromene [ No CAS ]

References: [1]Journal of the American Chemical Society,2005,vol. 127,p. 2709 - 2716.
[2]Journal of the American Chemical Society,2001,vol. 123,p. 5814 - 5815.

5
[ 104190-22-9 ]
[ 704-00-7 ]

References: [1]Journal of the American Chemical Society,2001,vol. 123,p. 5814 - 5815.

6
[ 67-56-1 ]
[ 201230-82-2 ]
[ 104190-22-9 ]
(Z)-3-methoxy-1-[(methoxycarbonyl)methylene]-3-methyl-1,3-dihydroisobenzofuran [ No CAS ]
(E)-3-methoxy-1-[(methoxycarbonyl)methylene]-3-methyl-1,3-dihydroisobenzofuran [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 574 - 585.

7
[ 67-56-1 ]
[ 201230-82-2 ]
[ 104190-22-9 ]
dimethyl 2-(2-dimethoxymethylphenyl)-but-2-enedioate [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 574 - 585.

8
[ 201230-82-2 ]
[ 67-63-0 ]
[ 104190-22-9 ]
(Z)-3-isopropoxy-1-[(isopropoxycarbonyl)methylene]-3-methyl-1,3-dihydroisobenzofuran [ No CAS ]
(E)-3-isopropoxy-1-[(isopropoxycarbonyl)methylene]-3-methyl-1,3-dihydroisobenzofuran [ No CAS ]

References: [1]European Journal of Organic Chemistry,2004,p. 574 - 585.

9
[ 104190-22-9 ]
[ 153093-73-3 ]

References: [1]Liebigs Annalen der Chemie,1993,p. 1009 - 1016.

10
[ 104190-22-9 ]
8,9,12,13-tetradehydro-6,7-dihydro-5H-benzoundecen-5-one [ No CAS ]

References: [1]Liebigs Annalen der Chemie,1993,p. 1009 - 1016.

11
[ 104190-22-9 ]
[ 153093-74-4 ]

References: [1]Liebigs Annalen der Chemie,1993,p. 1009 - 1016.

12
[ 1156005-30-9 ]
[ 104190-22-9 ]
22,25-bis{2-(2-acetylphenyl)-1-ethynyl}-1,20-dioxa[7.7]paracyclophane [ No CAS ]
22,25-bis{2-(2-acetylphenyl)-1-ethynyl}-1,20-dioxa[7.7]paracyclophane [ No CAS ]

References: [1]Chemical Communications,2009,p. 1870 - 1872.

13
[ 917-64-6 ]
[ 104190-22-9 ]
2-(2-ethynyl-phenyl)-propan-2-ol [ No CAS ]

References: [1]Organic Letters,2009,vol. 11,p. 5350 - 5353.

14
1-(2-((trimethylsilyl)ethynyl)phenyl)ethanone [ No CAS ]
[ 104190-22-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With potassium carbonate; In methanol; at 20℃; for 3h;	To an eggplant flask was added 1-(2-((trimethylsilyl)ethynyl)phenyl)ethan-1-one (5.83g, 0.027mol), potassium carbonate (0.37g, 0.0027mol) and methanol , and stirred at room temperature for 3 hours. After the reaction was completed, it was quenched by adding saturated ammonium chloride solution, extracted with dichloromethane, washed with water, dried over sodium sulfate, and concentrated to obtain 1-(2-ethynylphenyl)ethan-1-one with a yield of 99%.

References: [1]Patent: CN114133336,2022,A .Location in patent: Paragraph 0081; 0085.
[2]Organic Letters,2014,vol. 16,p. 5588 - 5591.
[3]Journal of Organic Chemistry,2015,vol. 80,p. 11360 - 11368.
[4]Organic Letters,2009,vol. 11,p. 5350 - 5353.
[5]Chemical Communications,2013,vol. 49,p. 11320 - 11322.
[6]Journal of Organic Chemistry,2018,vol. 83,p. 7799 - 7813.
[7]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3612 - 3618.
[8]Advanced Synthesis and Catalysis,2021,vol. 363,p. 4024 - 4032.
[9]Chinese Journal of Chemistry,2022,vol. 40,p. 46 - 52.

15
[ 3607-17-8 ]
[ 104190-22-9 ]
[ 1309565-92-1 ]

References: [1]Organic Letters,2011,vol. 13,p. 3190 - 3193.

16
[ 104190-22-9 ]
[ 1309565-80-7 ]

References: [1]Organic Letters,2011,vol. 13,p. 3190 - 3193.

17
[ 104190-22-9 ]
C₁₇H₂₂O₂ [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14787 - 14790.

18
[ 104190-22-9 ]
[ 149-73-5 ]
o-ethynylacetophenone [ No CAS ]

References: [1]Chemistry - A European Journal,2013,vol. 19,p. 14787 - 14790.

19
[ 589-87-7 ]
[ 104190-22-9 ]
1-(2-((4-bromophenyl)ethynyl)phenyl)ethan-1-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.

20
[ 625-95-6 ]
[ 104190-22-9 ]
1-{2-[2-(3-methylphenyl)ethynyl]phenyl}ethan-1-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.

21
[ 19099-56-0 ]
[ 104190-22-9 ]
C₁₉H₁₈O [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.

22
[ 591-18-4 ]
[ 104190-22-9 ]
1-(2-((3-bromophenyl)ethynyl)phenyl)ethan-1-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3612 - 3618.

23
[ 31599-61-8 ]
[ 104190-22-9 ]
C₁₈H₁₆O [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.

24
[ 22445-41-6 ]
[ 104190-22-9 ]
1-(2-((3,5-dimethylphenyl)ethynyl)phenyl)ethan-1-one [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.

25
[ 25245-27-6 ]
[ 104190-22-9 ]
C₁₈H₁₆O₃ [ No CAS ]

References: [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 13284 - 13288.
Angew. Chem.,2013,vol. 125,p. 13526 - 13530,5.

26
[ 124-38-9 ]
[ 104190-22-9 ]
[ 74-88-4 ]
[ 1487303-55-8 ]
methyl (E)-2-[3-methyleneisobenzofuran-1(3H)-ylidene]acetate [ No CAS ]

References: [1]Chemical Communications,2013,vol. 49,p. 11320 - 11322.

27
[ 2142-69-0 ]
[ 104190-22-9 ]

References: [1]Chemical Communications,2013,vol. 49,p. 11320 - 11322.
[2]Journal of Organic Chemistry,2015,vol. 80,p. 11360 - 11368.
[3]Journal of Organic Chemistry,2018,vol. 83,p. 7799 - 7813.
[4]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3612 - 3618.
[5]Advanced Synthesis and Catalysis,2021,vol. 363,p. 4024 - 4032.

28
[ 624-31-7 ]
[ 104190-22-9 ]
[ 1262832-17-6 ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 11360 - 11368.

29
[ 619-44-3 ]
[ 104190-22-9 ]
methyl 4-((2-acetylphenyl)ethynyl)benzoate [ No CAS ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 11360 - 11368.

30
[ 90-14-2 ]
[ 104190-22-9 ]
1-{2-[2-(naphthalen-1-yl)ethynyl]phenyl}ethan-1-one [ No CAS ]

References: [1]Journal of Organic Chemistry,2015,vol. 80,p. 11360 - 11368.

31
[ 62-53-3 ]
[ 104190-22-9 ]
[ 90-30-2 ]

References: [1]Journal of Organic Chemistry,2016,vol. 81,p. 1696 - 1703.

32
[ 2142-70-3 ]
[ 104190-22-9 ]

References: [1]Organic Letters,2014,vol. 16,p. 5588 - 5591.

33
[ 104190-22-9 ]
C₁₈H₁₉NO₄S [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 5588 - 5591.

34
[ 941-55-9 ]
[ 104190-22-9 ]
C₁₇H₁₅N₃O₃S [ No CAS ]

References: [1]Organic Letters,2014,vol. 16,p. 5588 - 5591.

35
[ 78331-59-6 ]
[ 104190-22-9 ]
C₂₀H₂₄O₅ [ No CAS ]

References: [1]Chemical Science,2016,vol. 7,p. 4134 - 4139.

36
1-(2-((triisopropylsilyl)ethynyl)phenyl)ethan-1-one [ No CAS ]
[ 104190-22-9 ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 13003 - 13011.

37
[ 696-62-8 ]
[ 104190-22-9 ]
[ 745825-75-6 ]

References: [1]Journal of Organic Chemistry,2017,vol. 82,p. 13003 - 13011.
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3612 - 3618.
[3]Chinese Journal of Chemistry,2022,vol. 40,p. 46 - 52.

38
[ 593-56-6 ]
[ 104190-22-9 ]
C₁₁H₁₁NO [ No CAS ]
C₁₁H₁₁NO [ No CAS ]

References: [1]Chemistry - A European Journal,2018,vol. 24,p. 9530 - 9534.

39
[ 615-43-0 ]
[ 104190-22-9 ]
1-(2-((2-aminophenyl)ethynyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 5h;Inert atmosphere;	General procedure: To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield.

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136.
[2]Dyes and Pigments,2019,vol. 160,p. 58 - 63.
[3]Chinese Journal of Chemistry,2022,vol. 40,p. 46 - 52.

40
[ 29289-13-2 ]
[ 104190-22-9 ]
7-hydroxy-2,7-dimethylindazolo[2,3-b]isoquinolin-12(7H)-one [ No CAS ]

References: [1]Dyes and Pigments,2019,vol. 160,p. 58 - 63.
[2]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136.

41
[ 29289-13-2 ]
[ 104190-22-9 ]
1-(2-((2-amino-5-methylphenyl)ethynyl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 5h;Inert atmosphere;	General procedure: To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield.

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136.
[2]Dyes and Pigments,2019,vol. 160,p. 58 - 63.

42
[ 63069-48-7 ]
[ 104190-22-9 ]
2-chloro-7-hydroxy-7-methylindazolo[2,3-b]isoquinolin-12(7H)-one [ No CAS ]

References: [1]Dyes and Pigments,2019,vol. 160,p. 58 - 63.
[2]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136.

43
[ 63069-48-7 ]
[ 104190-22-9 ]
1-(2-((2-amino-5-chlorophenyl)ethynyl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 5h;Inert atmosphere;	General procedure: To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield.

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136.
[2]Dyes and Pigments,2019,vol. 160,p. 58 - 63.

44
[ 104190-22-9 ]
[ 163444-17-5 ]
1-(2-((2-amino-5-(trifluoromethyl)phenyl)ethynyl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 5h;Inert atmosphere;	General procedure: To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield.

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 9125 - 9136.
[2]Dyes and Pigments,2019,vol. 160,p. 58 - 63.

45
[ 104190-22-9 ]
[ 128318-63-8 ]
1-(2-((2-amino-5-tert-butylphenyl)ethynyl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 5h;Inert atmosphere;	To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield. Yellow solid, mp 91.0-92.0 C. IR ν (KBr, cm-1) 3477,3363, 1682, 1558, 1413, 1334, 1306, 1242, 1201, 1071, 1016, 891,741. 1H NMR (400 MHz, CDCl3) δ (ppm) 7.84-7.82 (m,1H, Ar-H),7.70-7.68 (m, 1H, Ar-H), 7.52-7.48 (m, 1H, Ar-H), 7.40-7.36 (m, 2H,2×Ar-H), 7.21 (dd, J=8.5, 2.3 Hz, 1H, Ar-H), 6.71 (d, J=8.5 Hz,1H, Ar-H), 4.61 (s, 2H, NH2), 2.68 (s, 3H, CH3), 1.29 (s, 9H, 3×CH3).13C NMR (101 MHz, CDCl3) δ 198.9, 147.2, 140.3, 138.3, 134.2, 131.9,129.8, 128.6, 127.9, 127.5, 122.7, 114.4, 106.9, 94.0, 92.6, 34.0, 31.5,28.9. HRMS (TOF MS CI+) calculated for C20H22NO+ [M+H+]+:292.1701, found 292.1696.

References: [1]Dyes and Pigments,2019,vol. 160,p. 58 - 63.

46
[ 216393-67-8 ]
[ 104190-22-9 ]
2-chloro-4-fluoro-7-hydroxy-7-methylindazolo[2,3-b]isoquinolin-12(7H)-one [ No CAS ]

References: [1]Dyes and Pigments,2019,vol. 160,p. 58 - 63.

47
[ 216393-67-8 ]
[ 104190-22-9 ]
1-(2-((2-amino-5-chloro-3-fluorophenyl)ethynyl)phenyl)ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 20℃; for 5h;Inert atmosphere;	General procedure: To a 50 mL oven-dried flask containing a magnetic stirring bar, Pd(PPh3)2Cl2 (14.0 mg, 0.02 mmol, 1.0 mol %), CuI (2.0 mg, 0.01 mmol, 0.5 mol %), 4-(tert-butyl)-2-iodoaniline (550.0 mg, 2.0 mmol), 2 (317.0 mg,2.2 mmol) [26], and Et3N (10 mL) were added in sequence under argon atmosphere at room temperature. The resulting reaction mixture was stirred for 5 h, then the reaction mixture was filtered through a shortpad of celite, and the solid was washed with EtOAc (20 mL). The combined organic phase was concentrated under reduced pressure, andthe residue was purified by column chromatography on silica gel(eluent: petroleum ether/ethyl acetate=10:1) to afford pure product4c in 75% yield.

References: [1]Dyes and Pigments,2019,vol. 160,p. 58 - 63.

48
[ 593-56-6 ]
[ 104190-22-9 ]
C₁₁H₁₁NO [ No CAS ]