[ CAS No. 13679-75-9 ] {[proInfo.proName]}

Name: 13679-75-9|2-Propionylthiophene|98%
Brand: Ambeed
SKU: A691949
Price: 11.0 USD
Availability: InStock
Rating: 95 (30 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 13679-75-9

Structure of 13679-75-9 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 13679-75-9 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13679-75-9 ]

SDS Specification

Alternatived Products of [ 13679-75-9 ]

Product Details of [ 13679-75-9 ]

CAS No. :	13679-75-9	MDL No. :	MFCD00005446
Formula :	C₇H₈OS	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MFPZQZZWAMAHOY-UHFFFAOYSA-N
M.W :	140.20	Pubchem ID :	26179
Synonyms :

Calculated chemistry of [ 13679-75-9 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	5
Fraction Csp3 :	0.29
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.32
TPSA :	45.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.85
Log Po/w (XLOGP3) :	1.72
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	1.1
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.03

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.07
Solubility :	1.19 mg/ml ; 0.00847 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	0.723 mg/ml ; 0.00516 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.38
Solubility :	0.584 mg/ml ; 0.00417 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.83

Safety of [ 13679-75-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280	UN#:	N/A
Hazard Statements:	H302-H312-H332	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 13679-75-9 ]

* 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.

Upstream synthesis route of [ 13679-75-9 ]
Downstream synthetic route of [ 13679-75-9 ]

[ 13679-75-9 ] Synthesis Path-Upstream 1~2

1
[ 13679-75-9 ]
[ 7664-93-9 ]
[ 79-84-5 ]
[ 802294-64-0 ]

Reference： [1] Chemische Berichte, 1886, vol. 19, p. 677

2
[ 13679-75-9 ]
[ 19418-11-2 ]

Reference： [1] Chemische Berichte, 1887, vol. 20, p. 518

[ 13679-75-9 ] Synthesis Path-Downstream 1~45

1
[ 188290-36-0 ]
[ 79-03-8 ]
[ 13679-75-9 ]

Yield	Reaction Conditions	Operation in experiment
Ca. 100%	With aluminum (III) chloride; In dichloromethane; at 0℃; for 1.5h;Inert atmosphere;	6.1 Preparation of 2-propionyl thiophene 1g of thiophene was dissolved in 10 mL of anhydrous dichloromethane, added with 1.2 eq of propionylchloride at 0 C under nitrogen, and then with 1.5 eq of anhydrous AlCl3 in batches. The reaction was preformed at 0 C for 1.5 hours, and monitored by TLC. The reaction mixture was treated with an icy 1N HCl under stirring and extracted with dichloromethane. The organic phase was evaporated to dryness to give oily 2-propionylthiophene (1.65g). Yield, about 100%. 1H NMR (CDCl3, 400 MHz): delta 7.70 (d, J= 4.0 Hz, 1H), 7.64 (d, J = 5.0 Hz, 1H), 7.13 (dd, J = 4.0, J = 5.0 Hz, 1H), 2.94 (q, J= 7.2 Hz, 2H), 1.23 (t, J= 7.2 Hz, 3H). ESI-MS m/z: 142.2 [M+H]+.
Ca. 100%	With aluminum (III) chloride; In dichloromethane; at 0℃; for 1.5h;Inert atmosphere;	1 g of thiophene was dissolved in 10 mL of anhydrous dichloromethane, added with 1.2 eq of propionylchloride at 0 C. under nitrogen, and then with 1.5 eq of anhydrous AlCl3 in batches. The reaction was preformed at 0 C. for 1.5 hours, and monitored by TLC. The reaction mixture was treated with an icy 1N HCl under stirring and extracted with dichloromethane. The organic phase was evaporated to dryness to give oily 2-propionylthiophene (1.65 g). Yield, about 100%. 1H NMR (CDCl3, 400 MHz): delta 7.70 (d, J=4.0 Hz, 1H), 7.64 (d, J=5.0 Hz, 1H), 7.13 (dd, J=4.0, J=5.0 Hz, 1H), 2.94 (q, J=7.2 Hz, 2H), 1.23 (t, J=7.2 Hz, 3H). ESI-MS m/z: 142.2 [M+H]+.
81%	With MoO4(AlCl2)2; In neat (no solvent); at 20℃; for 12h;Green chemistry;	General procedure: The Friedel-Crafts acylation of Anisole (1 g, 9.26 mmol)(Aldrich, 99.0%) with propionyl chloride (5 equiv.)(Aldrich, 99.0%) using the prepared MoO4(AlCl22(5 wt%, 10 mg) catalyst was carried out in a magneticallystirred two-necked round bottom flask fitted witha guard tube (CaCl2, activated at 150 C for 2 h. Thepresent reaction mixture stirred at room temperature up tothe completion of reaction. Reaction progress was monitoredby thin layer chromatography (TLC). After completionof the reaction, reaction mixture was filtered andsolid catalyst was separated out. The separated solid catalystcan be recycled in next attempt of Friedel-Craftsacylation reaction. The reaction mixture was washed withdichloromethane (DCM) and water, the same process wasdone triplicate and collected the organic layer. The organiclayer was then dried over anhydrous sodium sulfate andconcentrated on rotary evaporator and crude acylated productwas obtained and purified on column chromatography.

Reference： [1]Patent: EP2848617,2015,A1 .Location in patent: Paragraph 0091; 0092
[2]Patent: US2015/141419,2015,A1 .Location in patent: Paragraph 0151; 0152
[3]Synthetic Communications,2008,vol. 38,p. 255 - 264
[4]Journal of the Indian Chemical Society,2005,vol. 82,p. 398 - 400
[5]Journal of Chemical Research - Part S,2003,p. 694 - 695
[6]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 8243 - 8250
[7]Synlett,2003,p. 247 - 249
[8]Justus Liebigs Annalen der Chemie,1921,vol. 424,p. 22
[9]Journal of the American Chemical Society,1932,vol. 64,p. 451,452 Anm. 10
[10]Chemische Berichte,1886,vol. 19,p. 677
[11]Chemical and pharmaceutical bulletin,1960,vol. 8,p. 1046 - 1050
[12]Organic and Biomolecular Chemistry,2015,vol. 13,p. 11651 - 11656

2
[ 188290-36-0 ]
[ 123-62-6 ]
[ 13679-75-9 ]

Yield	Reaction Conditions	Operation in experiment
96.8%	With phosphorus pentoxide; phosphoric acid; at 95 - 100℃; for 8h;	The mixture of thiophene (1) (34.1 g, 0.405 mol), propionic anhydride (64.6 g, 0.497 mol), phosphoric acid (4 mL) and phosphoric anhydride (0.8 g, 5.633 mmol) was heated under reflux for 8 h. After cooling to room temperature, cold water (100 mL) was added, and stirred at room temperature for 30 min. The mixture was extracted with dichloromethane (3×50 mL). The organic layer was washed with 20% NaOH solution (100 mL), water (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give (2) as yellow oil (54.2 g, 96.8%), (lit.8,9 pale yellow oil). IR (cm-1): 3091, 2979, 2938, 1665, 1518, 1459, 1417, 1356, 1228, 1055, 941, 904, 853, 799, 723, 644, 585; 1H NMR (300 MHz, CDCl3) delta 1.19-1.24 (m, 3H),2.89-2.96 (m, 2H), 7.09-7.12 (m, 1H), 7.59-7.61 (m, 1H), 7.69-7.71(m, 1H); 13C NMR (75 MHz, CDCl3) delta 8.27, 32.28, 127.83, 131.39, 132.97, 143.89, 193.54; MS m/z: 141.0 ([M+H]+, 100%).

Reference： [1]Journal of Chemical Research,2013,vol. 37,p. 406 - 408
[2]New Journal of Chemistry,2017,vol. 41,p. 14871 - 14875
[3]Journal of Organic Chemistry,2012,vol. 77,p. 7512 - 7525
[4]Journal of Organic Chemistry,1948,vol. 13,p. 409,412
[5]Journal of the American Chemical Society,1947,vol. 69,p. 3093,3095
[6]Bulletin of the Chemical Society of Japan,1982,vol. 55,p. 957 - 958
[7]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 2546 - 2550

3
[ 13679-75-9 ]
[ 60100-09-6 ]
[ 6315-55-5 ]
[ 39204-58-5 ]

Yield	Reaction Conditions	Operation in experiment
	at 180℃; Erhitzen mit wss. Natronlauge auf 130;
	anschliessend mit wss. NaOH erhitzen;

Reference： [1]Blicke; Burckhalter [Journal of the American Chemical Society, 1942, vol. 64, p. 477,479] Hill; Loev [Journal of Organic Chemistry, 1973, vol. 38, p. 2102]
[2]Blicke; Burckhalter [Journal of the American Chemical Society, 1942, vol. 64, p. 477,479]

4
[ 13679-75-9 ]
[ 1551-27-5 ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethylsilane; trifluoroacetic acid; at 0 - 20℃;	6.2 Preparation of 2-n-propylthiophene 2-propionylthiophene (1.5g) was dissolved in trifluoroacetic acid (10 mL) at 0 C, added with 4 eq of triethyl silane, and stirred at room temperature overnight. Purification by column chromatography gave 2-n-propylthiophene. Yield, 92%. 1H NMR (CDCl3, 400 MHz): delta 7.10 (d, J = 4.0 Hz, 1H), 6,91 (dd, J= 4.0, J = 5.0 Hz, 1H), 6,78 (d, J= 5.0 Hz, 1H), 2.79 (t, J= 7.4 Hz, 2H), 1.69(m, 2H), 0.90(t, J = 7.4 Hz, 3H). ESI-MS m/z: 127.0 [M+H]+.
92%	With triethylsilane; trifluoroacetic acid; at 0 - 20℃;	2-propionylthiophene (1.5 g) was dissolved in trifluoroacetic acid (10 mL) at 0 C., added with 4 eq of triethyl silane, and stirred at room temperature overnight. Purification by column chromatography gave 2-n-propylthiophene. Yield, 92%. 1H NMR (CDCl3, 400 MHz): delta 7.10 (d, J=4.0 Hz, 1H), 6.91 (dd, J=4.0, J=5.0 Hz, 1H), 6.78 (d, J=5.0 Hz, 1H), 2.79 (t, J=7.4 Hz, 2H), 1.69 (m, 2H), 0.90 (t, J=7.4 Hz, 3H). ESI-MS m/z: 127.0 [M+H]+.
	With potassium hydroxide; hydrazine; In ethylene glycol;	A. Preparation of 2-(n-propyl)thiophene Ethylene glycol (150 ml) and potassium hydroxide (25 g as 85% aqueous solution) were combined and heated to about 80 C. to dissolve the potassium hydroxide. Hydrazine (15 ml) was added followed by 1-(2-thienyl)-1-propanone (15 g, 107 mmole) The mixture was heated to reflux at about 200 C. for three hours. Additional ethylene glycol was added and product was collected in a Dean Stark trap. The ethylene glycol layer was separated from the product layer which was a yellow liquid. The product liquid was distilled in vacuo (about 5 mm Hg) at 35-37 C. to provide 2-(n-propyl)thiophene (7.45 g). PMR (CDCl3) 7.1 (d, J=5 Hz, 1H), 6.9 (t, J=3,5 Hz, 1H), 6.8 (d, 3 Hz, 1H), 2.8 (t, J=10 Hz, 2H), 1.7 (m, 2H), 1.0 (t, J=9 Hz, 3H).

Reference： [1]Patent: EP2848617,2015,A1 .Location in patent: Paragraph 0093; 0094
[2]Patent: US2015/141419,2015,A1 .Location in patent: Paragraph 0153; 0154
[3]Justus Liebigs Annalen der Chemie,1921,vol. 424,p. 22
[4]Journal of the American Chemical Society,1951,vol. 73,p. 5240,5241
[5]Journal of Organic Chemistry,1949,vol. 14,p. 638,639
[6]Journal of Medicinal Chemistry,1992,vol. 35,p. 3012 - 3016
[7]Patent: US5302724,1994,A

5
[ 13679-75-9 ]
[ 6315-55-5 ]
[ 39204-58-5 ]

Yield	Reaction Conditions	Operation in experiment
	With formamide at 180℃; anschliessendes Erwaermen mit wss. Natronlauge;

Reference： [1]Blicke; Burckhalter [Journal of the American Chemical Society, 1942, vol. 64, p. 477,479] Hill; Loev [Journal of Organic Chemistry, 1973, vol. 38, p. 2102]

6
[ 13679-75-9 ]
[ 2835-77-0 ]
[ 20364-70-9 ]

Yield	Reaction Conditions	Operation in experiment
73%	With indium(III) chloride; at 100℃; for 24h;	2-Aminobenzophenone (1.972 g, lOmmol), 1-(2-thienyl)-1-propanone (1.402 g, lOmmol), anhydrous indium trichloride (0.221 g, 2 mmo 1), without solvent, placed in oil bath at 100 C for 24 hours, quenched with water, ethyl acetate extraction, anhydrous sodium sulfate drying. The residue was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 20/1, v / v) as a white solid in 73% yield. Melting point: 116-118. (D, J = 8.0 Hz, lH), 7.60 (ddd, J = 7.2, & lt; RTI ID = 0.0 & gt; (M, 2H), 7.38-7.30 (m, 2H), 7.28-7.26 (m, 2 Hz), 7.13 (m, (1, 5, 127.6, 126.2, 19.2;HRMS (ESI) calcd for C20H16NS (Mu + Eta): 302.0995, Found: 302.0998

Reference： [1]Organic Letters,2015,vol. 17,p. 2816 - 2819
[2]Patent: CN104817496,2017,B .Location in patent: Paragraph 0065
[3]Zeitschrift fur Chemie,1968,vol. 8,p. 179

7
[ 13679-75-9 ]
[ 23229-69-8 ]

Yield	Reaction Conditions	Operation in experiment
	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃;	A soluble leaving group unit for production of the specific compound of the present invention was synthesized with reference to Chem. Mater. 16, 4783 (2004) and J. Am. Chem. Soc. 126, 1596 (2006), according to Schemes 2 to 5.

Reference： [1]Chemische Berichte,1994,vol. 127,p. 359 - 366
[2]Patent: WO2009/128559,2009,A1 .Location in patent: Page/Page column 37
[3]Synthesis,2009,p. 2413 - 2417
[4]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2540 - 2546

8
[ 13679-75-9 ]
[ 75815-46-2 ]

Yield	Reaction Conditions	Operation in experiment
95.9%	With phenyltrimethylammonium tribromide; In dichloromethane; for 12h;Reflux;	PTT (37.6 g, 0.1 mol) was added to a solution of compound 2 (14 g, 0.1 mol) in dichloromethane (150 mL) and the mixture was heated under reflux for 12 h. After cooling to room temperature, the reaction mixture was neutralised with aqueous potassium carbonate solution and extracted with dichloromethane (3×50 mL). The organic layer was washed with water (100 mL) and brine (100 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give (3) as pale yellow oil (21.1g, 95.9%), (lit.14 pale yellow oil). IR (cm-1): 3103, 2978, 2925, 2862, 1664, 1517, 1441, 1413, 1376, 1355, 1246, 1167, 1064, 985, 942, 903, 855, 724, 648, 585, 566, 538; 1H NMR (300 MHz, CDCl3) delta 1.84-1.94 (m, 3H), 5.12-5.18 (m, 1H), 7.14-7.17 (m, 1H), 7.68-7.70 (m, 1H), 7.83-7.85 (m, 1H); 13C NMR (75 MHz, CDCl3) delta 20.27, 42.42, 128.23, 133.02, 134.81, 140.76, 186.73; MS m/z: 219.0 ([M-H]+, 100%), 221.0 ([M+H]+, 100%).
	With hydrogen bromide; bromine; acetic acid; In water; at 0 - 20℃; for 2.5h;	Example 1 : This example illustrates the preparation of 3-chloro-6-methyl-5-thiophen-2-yl-4- (2,4,6-trifluorophenyl)-pyridazine (Compound No.l.h.198); a) Preparation of 2-bromo-<strong>[13679-75-9]1-thiophen-2-yl-propan-1-one</strong>; Bromine (3.7 ml) is added to the mixture of 1-(2-thienyl)-1 -propane (10 g), 0.1 ml of hydrobromic acid (48 % solution) and 80 ml of acetic acid at 0 0C under a nitrogen atmosphere. Subsequently, the mixture is stirred for 2.5 h at room temperature. The reaction mixture is evaporated under reduced pressure. 2-Bromo-<strong>[13679-75-9]1-thiophen-2-yl-propan-1-one</strong> is obtained as a brown oil, which is used in the next step without further purification.

Reference： [1]Journal of Chemical Research,2013,vol. 37,p. 406 - 408
[2]Tetrahedron Letters,1981,vol. 22,p. 4305 - 4308
[3]Angewandte Chemie - International Edition,2009,vol. 48,p. 154 - 156
[4]Journal of Medicinal Chemistry,2009,vol. 52,p. 6768 - 6781
[5]Patent: WO2013/55949,2013,A2 .Location in patent: Page/Page column 36
[6]Organic Letters,2017,vol. 19,p. 2548 - 2551
[7]Patent: WO2008/9406,2008,A1 .Location in patent: Page/Page column 16

9
[ 13679-75-9 ]
[ 36155-78-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bromine;aluminum (III) chloride; In chloroform; at 20℃; for 17h;	EXAMPLE 112; Preparation of 2-Amino-5-(3bromophenyl)-5-[5-(2-ethyl-[1,3]dioxolan-2-yl)-thiophen-3-yl]-3-methyl-3,5-dihydro-imidazol-4-one; Step a); A stirred suspension of aluminum trichloride (6.27 g, 47.1 mmol) in chloroform at room temperature was treated sequentially with 2-(1-propionyl)thiophene (3.00 g, 21.4 mmol) and bromine (3.60 g, 22.4 mmol), stirred for 17 h, poured into iced water and diluted with methylene chloride. The phases were separated and the aqueous phase was extracted with methylene chloride. The extracts and the organic phase were combined, washed with water and brine, dried over sodium sulfate and concentrated to afford 2 (5.51 g, 117%) as a dark orange oil: 1H NMR (300 MHz, CDCl3) delta 7.59 (d, J=1.1 Hz, 1H), 7.51 (d, J=1.1 Hz, 1H), 2.91 (q, J=7.3 Hz, 2H), 1.23 (t, J=7.3 Hz, 3H); ESI MS m/z 219 [C7H7BrOS+H]+.
	With bromine;AlCl3; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform;	1d. 1-(4-Bromo-2-thienyl)-1-propanone A 47.3 g (338 mmol) sample of 1-(2-thienyl)-1-propanone (Aldrich) was dissolved in 225 mL of CHCl3 and 101.3 g (760 mmol) of AlCl3 was added with stirring. To this mixture was added a solution of bromine (57.5 g, 360 mmol) in 375 mL of CHCl3. The mixture was stirred at room temperature over night then poured into 500 mL of ice water. The organic layer was separated, washed with water (2*200 mL), dried over MgSO4, filtered and evaporated to yield 81 g of the crude title compound, which was taken directly to the next step. mp 40-41 C.; MS: 158 (M+H)+, 236 (M+NH4)+; NMR (CDCl3) delta: 1.22 (t, 3H, J=7.5 Hz), 2.91 (q, 2H, J=7.5Hz), 7.51 (d, 1H), 7.60 (d, 1H). IR (KBr): 2960, 1670, 1400, 1220 cm-1.

Reference： [1]Patent: US2007/4786,2007,A1 .Location in patent: Page/Page column 39-40
[2]Journal of Organic Chemistry,1997,vol. 62,p. 2782 - 2785
[3]Patent: US5659037,1997,A
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5164 - 5170

10
[ 393148-57-7 ]
[ 13679-75-9 ]

Reference： [1]Catalysis science and technology,2019,vol. 9,p. 6327 - 6334
[2]Chemistry - A European Journal,2019,vol. 25,p. 7820 - 7825
[3]Chemistry - A European Journal,2018,vol. 24,p. 4043 - 4049
[4]Journal of the American Chemical Society,2005,vol. 127,p. 6172 - 6173

11
[ 23229-69-8 ]
[ 13679-75-9 ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 1695 - 1698
[2]Canadian Journal of Chemistry,2005,vol. 83,p. 702 - 710
[3]Organic Letters,2010,vol. 12,p. 2214 - 2217
[4]Chinese Journal of Chemistry,2012,vol. 30,p. 1289 - 1294

12
[ 13679-75-9 ]
[ 1972-28-7 ]
C₁₃H₁₈N₂O₅S [ No CAS ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3671 - 3674

13
[ 13679-75-9 ]
[ 19418-11-2 ]

Reference： [1]Chemische Berichte,1887,vol. 20,p. 518

14
[ 13679-75-9 ]
[ 32412-47-8 ]

Yield	Reaction Conditions	Operation in experiment
20%	With nitric acid; acetic anhydride; acetic acid; at 0 - 20℃; for 5.5h;	To a stirred solution of 1-(2-THIENYL)-1-PROPANONE (3g) in acetic anhydride (6ML) at 0C was added dropwise a solution of fuming nitric acid in acetic acid (2ml in 10MI). After 30min, the reaction was warmed to room temperature and let stir for 5hrs where a solid precipitated out. Ice was added to the reaction and the solid was filtered. The solid was purified by flash column chromatography (HEX/CH2CI2, 3: 1 and 2: 1) to yield 800mg of desired product (20%).
20%	With nitric acid; In acetic anhydride; acetic acid; at 0 - 20℃; for 5.5h;	To a stirred solution of l-(2-thienyl)-l-propanone (3 g) in acetic anhydride (6 ml) at 0 C. was added dropwise a solution of fuming nitric acid in acetic acid (2 ml in 10 ml). After 30 min, the reaction was warmed to room temperature and let stir for 5 hrs where a solid precipitated out. Ice was added to the reaction and the solid was filtered. The solid was purified by flash column chromatography (Hex/CH2Cl2, 3:1 and 2:1) to yield 800 mg of desired product (20%).
20%	With nitric acid; In acetic acid; at 0 - 20℃; for 5.5h;	To a stirred solution of 1-(2-thienyl)-1-propanone (3 g) in acetic anhydride (6 ml) at 0 C. was added dropwise a solution of fuming nitric acid in acetic acid (2 ml in 10 ml). After 30 min, the reaction was warmed to room temperature and let stir for 5 hrs where a solid precipitated out. Ice was added to the reaction and the solid was filtered. The solid was purified by flash column chromatography (Hex/CH2Cl2, 3:1 and 2:1) to yield 800 mg of desired product (20%).

20%	With nitric acid; acetic anhydride; In acetic acid; at 0 - 20℃; for 5.5h;	PREPARATIVE EXAMPLE 13.28; Step A; To a stirred solution of 1-(2-thienyl)-1-propanone (3g) in acetic anhydride (6ml) at 0C was added dropwise a solution of fuming nitric acid in acetic acid (2ml in 10ml). After 30min, the reaction was warmed to room temperature and let stir for 5hrs where a solid precipitated out. Ice was added to the reaction and the solid was filtered. The solid was purified by flash column chromatography (Hex/CH2CI2, 3: 1 and 2: 1) to yield 800mg of desired product (20%).
20%	With nitric acid; acetic anhydride; acetic acid; at 0 - 20℃; for 5.5h;	To a stirred solution of 1-(2-thienyl)-1-propanone (3g) in acetic anhydride (6ml) at 0C was added dropwise a solution of fuming nitric acid in acetic acid (2ml in 10ml). After 30min, the reaction was warmed to room temperature and let stir for 5hrs where a solid precipitated out. Ice was added to the reaction and the solid was filtered. The solid was purified by flash column chromatography (Hex/CH2CI2, 3: 1 and 2: 1) to yield 800mg of desired product (20%).

Reference： [1]Patent: WO2004/33440,2004,A1 .Location in patent: Page 193
[2]Patent: US2004/147559,2004,A1 .Location in patent: Page 95
[3]Patent: US2004/106794,2004,A1 .Location in patent: Page 97-98
[4]Patent: WO2005/66147,2005,A1 .Location in patent: Page/Page column 165
[5]Patent: WO2005/68460,2005,A1 .Location in patent: Page/Page column 168

15
[ 13679-75-9 ]
[ 75815-46-2 ]
chloroform-petrol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In tetrachloromethane	2 2-(2-Bromopropionyl)thiophene PREPARATION 2 2-(2-Bromopropionyl)thiophene An ice cold solution of 2-propionylthiophene (1.40 g) in carbon tetrachloride (25 ml) was treated with a solution of bromine (0.54 ml) in carbon tetrachloride (20 ml) over 5 mins. The resulting solution was then stirred at room temperature. After 1.5 h the mixture was evaporated to an amber oil (2.17 g). A portion of the oil (600 mg) was subjected to preparative thin-layer chromatography on silica developing with chloroform-petrol (b.p. 60°-80° C.) (1:4) (4 runs) and gave an amber oil, the title bromide (410 mg), λmax (EtOH) 272.5 nm (ε7,910), 294 nm (ε8,340), νmax (CS2) 1658, 713 cm-1.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4650800, 1987, A

16
[ 13679-75-9 ]
sodium hyposulfite [ No CAS ]
[ 75815-46-2 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine In 1,4-dioxane; water	11.a (a) (a) 2-Bromo-1-(2-thienyl)-1-propanone To a solution of 20 g (14110-3 mol) of 2-propionyl-thiophene in 20 ml of anhydrous dioxan were added, in 75 min. at room-temperature and while stirring, 22.8 g (14210 -3 mol) of bromine. The reaction became exothermic and the medium was stirred for a further 2 hours at room-temperature. After that, 40 ml of water containing sodium hyposulphite was slowly added. After extraction with ethyl ether, the organic phases were washed with saline water, dried on sodium sulphate and heated to dryness under vacuum. In this manner, 31.10 g of 2-bromo-1-(2-thienyl)-1-propanone were obtained titrating 89.3% in G.P.C. namely a molar yield of 89.9%.

Reference： [1]Current Patent Assignee: SANOFI; INDUSTRIA CHIMICA PRODOTTI FRANCIS - US4675419, 1987, A

17
[ 13679-75-9 ]
[ 95-92-1 ]
ethyl 3-methyl-2,4-dioxo-4-(thiophen-2-yl)butanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium; In ethanol; water;	EXAMPLE 9 (RS)-2-Amino-3-[3-carboxy-5-(2-thienyl)isoxazol-4-yl]propionic acid, hydrate, 9a. To a cooled solution of sodium (4.1 g, 0.18 mol) in EtOH (100 mL) was added diethyl oxalate (24 mL, 0.18 mol). 1-(2-Thienyl)-1-propanone (20 mL, 0.16 mol) in EtOH (10 mL) was added to the cold solution over 15 min and the resulting mixture was stirred at 0 C for 2 h followed by 16 h at 22 C. The mixture was concentrated in vacuoand the residue was dissolved in water (400 mL). The aqueous phase was acidified with 1 M HCl to pH 3-4 and extracted with CH2Cl2(3 x 300 mL). The combined organic phases were dried (MgSO4) and concentrated in vacuo. Flash chromatography (silica gel, eluent: n-heptane/ethyl acetate = 3:1) gave ethyl 2,4-dioxo-3-methyl-4-(2-thienyl)butyrate (20.5 g, 53%).

Reference： [1]Journal of Fluorine Chemistry,2014,vol. 167,p. 184 - 191
[2]Patent: EP994107,2000,A1

18
[ 13679-75-9 ]
[ 95-92-1 ]
lithium ethyl 3-methyl-2,4-dioxo-4-thiophen-2-yl-butanonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		To a magnetically stirred solution of lithium bis(trimethylsilyl)amide (46.7 mL, 46.7 mmol) in diethyl ether (55 mL) was added a solution of 1-(2-thienyl)-1-propanone (6.0 g, 42.53 mmol) in diethyl ether (30 mL) at -78 C. After the mixture was stirred at the same temperature for an additional 45 minutes, diethyl oxalate (6.9 mL, 51.03 mmol) was added to the mixture. The reaction mixture was allowed to warm to room temperature and stirred for another 16 hours. The precipitate was filtered, washed with diethyl ether, and dried under vacuum to afford Intermediate I(a), i.e., a lithium salt of ethyl 3-methyl-2,4-dioxo-4-thiophen-2-yl-butanonate (6.14 g, 62%)

Reference： [1]Patent: US2008/90810,2008,A1 .Location in patent: Page/Page column 11

19
[ 13679-75-9 ]
[ 42416-71-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydroxylamine hydrochloride; sodium acetate; In methanol; at 20℃; for 20h;	Hydroxylamine hydrochloride (3.2 g, 46.3 mmol) and sodium acetate (3.8 g, 46.3 mmol) were added to 20 mL of methanol and the resulting white slurry was stirred at room temperature for 30 min. l-(Thiophen-2-yl)propan-l-one (5.9 g, 42.1 mmol) was added and the mixture was stirred at room temperature for 20 hours. Water (20 mL) was added and the product was extracted with EtOAc and the organic layer was washed with saturated NaHCO3 solution and dried over MgSO4. The solvent was evaporated in vacuo to give 6.3 g of the title compound. MS: (+) m/z 156.32 (M+l)

Reference： [1]Patent: WO2009/73669,2009,A1 .Location in patent: Page/Page column 90
[2]Organic Letters,2010,vol. 12,p. 2214 - 2217
[3]Journal of Organic Chemistry,2012,vol. 77,p. 7512 - 7525
[4]Chemistry - A European Journal,2017,vol. 23,p. 1779 - 1783

20
[ 13679-75-9 ]
[ 131213-83-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With ammonium iodide; RhH(CO)(PPh3)3; C52H58N4P2; isopropyl alcohol; potassium hydroxide; at 45℃; for 42h;	General procedure: Chiral macrocycles 1 and 2 were synthesized using the same procedure we previously reported [25]. Under air atmosphere, the complex RhH(CO)(PPh3)3 (9.2 mg, 0.01 mmol), (R, R, R', R')-2 (8.0 mg,0.01 mmol), and NH4I (22.0 mg, 0.15 mmol) were placed in a tube equipped with a Teflon-coated magnetic stirring bar. Then, iPrOH was added and the mixture was stirred at 65 C for 30 min. Next, an appropriate amount of KOH/iPrOH solution was added, and the mixture was continually stirred for another 10 min. Later, ketone was introduced, and the mixture was stirred at the desired temperature for the required reaction time. At the end of experiment, the reaction products were determined by GC using a chiral CP-Chiralsil-Dex CB column.

Reference： [1]Journal of the American Chemical Society,2014,vol. 136,p. 4031 - 4039
[2]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2540 - 2546
[3]Synthesis,2009,p. 2413 - 2417
[4]Catalysis Communications,2019,vol. 119,p. 153 - 158

21
[ 13679-75-9 ]
[ 623-00-7 ]
[ 1286260-92-1 ]

Yield	Reaction Conditions	Operation in experiment
12%	With PdCl(C3H5)(1,4-bis(diphenylphosphino)butane); potassium acetate; In pentan-1-ol; at 150℃; for 20h;Inert atmosphere;	General procedure: In a typical experiment, the aryl bromide (1 mmol), heteroaromatic derivative (2 mmol), KOAc (0.196 g, 2 mmol) and PdCl(C3H5)(dppb)17 (0.012 g, 0.02 mmol) were dissolved in pentan-1-ol or 3-methylbutanol (5 mL) (see tables) in a Schlenk tube under an argon atmosphere. The reaction mixture was stirred at 150 for 20 h. The solvent was removed in vacuo, then the crude mixture was purified by silica gel column chromatography.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 1383 - 1387

22
N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride [ No CAS ]
(4-hydroxy-1-methyl-4-thiophen-2-yl-piperidin-3-yl)-thiophen-2-yl-methanone [ No CAS ]
[ 13679-75-9 ]
[ 116539-55-0 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2260 - 2264
Angew. Chem.,

23
N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride [ No CAS ]
[ 13679-75-9 ]
[ 116539-55-0 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 2260 - 2264
Angew. Chem.,

24
[ 13679-75-9 ]
[ 39859-36-4 ]
6-bromo-3-methyl-4-phenyl-2-(thiophen-2-yl)quinoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With indium(III) chloride; at 100℃; for 24h;	2-amino-5-bromobenzophenone (2.761 g, 10 mmol), 1- (2'-thienyl) -1-propanone (1.402 g, lOmmol), anhydrous indium trichloride 0.22 lg, 2 mmol) was added to the oil bath at 100 C for 24 hours without solvent, quenched with water, extracted with ethyl acetate and dried over anhydrous sodium sulfate. The residue was purified by column chromatography (eluent: petroleum ether: ethyl acetate = 20/1, ¥ 8) to give a white solid in 72% yield. Melting point: 189-191 (11; (^ 111): 1576,1494,1351.111-1; 111 Li 1? (400 Mu zeta, CDC13, ppm) delta 7 ? 97 (d, J = 8.8 Hz, 1H (M, 3 H), 7.52-7.48 (m, 2H), 7.45 (d, J = 1.6), 7 ? 68 (dd, J = 8 · 8, 1.6 Hz, 1H) (100 MHz, CDCl3, ppm) delta153 · 8,147 (d, J = 8.4Hz, 2H), 7.15 (dd, J = 4.4Hz, 1H), 2.40 (s, 3H) 6,145.04,137.2,132,131.2,129.5,129.1,128.5,128.4,128.3,128.2,127.7,127.4,120.6,19.3; HRMS (ESI) calcd for C20Hi5NBrS (Mu + Eta): 380.0103, Found: 380.0098

Reference： [1]Organic Letters,2015,vol. 17,p. 2816 - 2819
[2]Patent: CN104817496,2017,B .Location in patent: Paragraph 0066

25
[ 13679-75-9 ]
[ 762-04-9 ]
diethyl 1-oxo-1-(thiophen-2-yl)propan-2-yl phosphate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With di-iodine pentaoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 80℃; for 48h;	General procedure: In a sealed tube (25mL),ketones 1 (0.25 mmol), H-phosphonates 2 (0.75 mmol), I2O5(0.25 mmol), DBU (0.25 mmol), and CH3CN (2 mL) were added. Thereaction vesselwas allowed to stir at 80 C for 48 h. After the reaction,the solution was concentrated in vacuum. The resulting mixture purifiedby flash column chromatography using amixture of petroleumether and ethyl acetate as eluent to give the desired product 3.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6901 - 6906

26
[ 13679-75-9 ]
[ 108-24-7 ]
(Z)-1-(thiophen-2-yl)prop-1-en-1-yl acetate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6897 - 6902
[2]Organic Letters,2015,vol. 17,p. 4918 - 4921

27
[ 13679-75-9 ]
[ 55368-42-8 ]
2-(4-bromophenyl)-4-(thiophen-2-yl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In N,N-dimethyl-formamide; at 120℃; for 12h;Sealed tube;	Weigh 0.3 mmol of 4-bromobenzamidine hydrochloride (0.0707 g)0.75 mmol of 2-acetylthiophene (0.1052 g),0.03 mmol of ferrous sulfate heptahydrate (0.0083 g), 0.03 mmol of 1,1,10-phenanthroline (0.0054 g), tetramethylpiperidineNitrogen oxide (TEMPO) (0.0563 g) was added to a 10 mL tube of test tubes and 2 mL of N, N-dimethylformamide (DMF) was addedAnd the mixture was sealed and sealed at 120 C for 12 hours. After the reaction, the reaction solution was successively passed through water, ethyl acetate, anhydrous sulfurSodium sulfate and column chromatography (column chromatography separation conditions: the stationary phase of 300 ~ 400 mesh silica gel, the mobile phase ethyl acetate(A) and petroleum ether (B), the mobile phase change program (A: B) is 1: 50 ? 1: 20, 0.0751 g of the reaction product (white solidbody). According to the characterization data, the obtained reaction produces pure 2- (4-bromophenyl) -4- (2-thienyl) pyrimidine (purity>95%), the structure is as follows:The product yield was calculated and 79%.

Reference： [1]Patent: CN106496127,2017,A .Location in patent: Paragraph 0239; 0240; 0241; 0242; 0243; 0244; 0245
[2]Journal of Organic Chemistry,2017,vol. 82,p. 1145 - 1154

28
[ 13679-75-9 ]
[ 149-30-4 ]
1-(benzo[d]thiazol-2-ylthio)-3-(2-thienyl)propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With dipotassium peroxodisulfate; potassium iodide; In dimethyl sulfoxide; at 20℃; for 24h;Schlenk technique;	A mixture of 1.0 mmol of 1- (2-thienyl) -1-propanone,0.5 mmol of mercaptobenzothiazole,20 mol% of potassium iodide,0.3 mmol of potassium persulfate, 1 ml of DMSO was added to the Schlenk tube under an air atmosphere and stirred at room temperature for 24 hours Time. After completion of the reaction, the separation and purification gave 2- (benzo [d] thiazol-2-ylthio) -1- (2-thienyl) acetone in 67% isolated yield. The product was identified by 1H, 13C NMR.

Reference： [1]Patent: CN106986843,2017,A .Location in patent: Paragraph 0031; 0032

29
[ 13679-75-9 ]
[ 529-23-7 ]
[ 127118-99-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In toluene; at 120℃; for 14h;Inert atmosphere; Sealed tube;	To a 15 mL reaction tube was added 1a (0.5 mmol, 60.5 mg)Toluene (3 mL),Cu (OAc) 2 (0.05 mmol, 9.1 mg),(0.1 mmol, 15.6 mg), TEMPO (1 mmol, 156.2 mg) and 2 g (0.6 mmol, 74.7 [mu] L).After vacuuming the reaction tube, the reaction tube is sealed,And the reaction was stirred in an oil bath at 120 C for 14 h.Stop the reaction,15 mL of dichloromethane was added,Then washed successively with water and saturated NaCl solution, and the organic phase was dried over anhydrous MgSO4.filter,Spin dry,Separation by silica gel column (petroleum ether / ethyl acetate = 5/1)The target product 3k (89.6 mg, 75%) was obtained.

Reference： [1]Patent: CN106749238,2017,A .Location in patent: Paragraph 0102; 0103; 0104

30
[ 13679-75-9 ]
[ 536-74-3 ]
[ 1312799-32-8 ]

Yield	Reaction Conditions	Operation in experiment
37%	With tert.-butylhydroperoxide; copper acetylacetonate; In chlorobenzene; at 120℃; for 12h;	A 0.4 mmol of 1-(2-thienyl)-1-propanone, 0.2 mmol of phenylacetylene, an appropriate amount of Copper(II) acetylacetonate , appropriate amount of Oxidizing agent , 1 ml of chlorobenzene in the air environment by adding SchlenkTube,The reaction was stirred at 120 oC for 12 hours.After the reaction is over,Separation and purification gave 2-benzoyloxy-1'-(2'-thienyl)-1'-acetone in 37% isolated yield.

Reference： [1]Patent: CN107011162,2017,A .Location in patent: Paragraph 0043
[2]New Journal of Chemistry,2018,vol. 42,p. 1581 - 1584

31
[ 13679-75-9 ]
[ 14290-11-0 ]
(1,3-diphenyl-1H-pyrazol-4-yl)(thiophen-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%		Was added 1i (0.6mmol, 84mg) in 15mL pressure tube, a Cu (OAc)2(0.1 mmol, 18 mg of), bpy(0.05 mmol, 8mg), the TEMPO (0.5 mmol, 78 mg) and chlorobenzene (3mL), evacuated After the vacuum was purged with nitrogen, the reaction tube was sealed andplaced in an oil bath at 120 C for 10 h.Then, 2a (0.5 mmol, 112 mg) was added to the reaction system andstirring was continued for 4 hin an air atmosphereat 120 C in an oil bath.The reaction was quenched with 10 mL of water and extracted with ethyl acetate (10 mL x 3). Theorganic phase was washed successively with water and saturated brine and dried over anhydrous sodium sulfate.Filtration, spin drying, separation on silica gel (petroleum ether / ethylacetate = 20/1)gavewhite solid product 3i (135 mg, 82%).

Reference： [1]Patent: CN107089950,2017,A .Location in patent: Paragraph 0046; 0047; 0048

32
[ 13679-75-9 ]
[ 23652-90-6 ]
[2-methyl-6-(thiophen-2-yl)pyridin-3-yl](phenyl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In N,N-dimethyl-formamide; at 120℃; for 20h;Sealed tube;	2a (0.5 mmol, 80.6 mg) was added to a 15 mL reaction tube containing N, N-dimethylformamide (2 mL),After dissolving with stirring, add 1 l (0.6 mmol, 84.1 mg),Cu (OAc) 2 (0.05mmol, 9.1mg),2,2'-bipyridine (0.1 mmol, 15.6 mg)And TEMPO (0.5 mmol, 78.1 mg),The reaction tube was sealed in the presence of air, and then the reaction was stirred in a 120 C. oil bath for 20 h.After the reaction, the reaction tube was cooled to room temperature, and water was added to quench the reaction.After extraction with ethyl acetate (8 mL × 3), the organic phase was washed with water and saturated brine in this order, and dried over anhydrous sodium sulfate.Filtration, spin-drying, and separation through a silica gel column (petroleum ether / ethyl acetate = 20/1)3l (114 mg, 82%) of the product was obtained as a yellow solid.

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 11230 - 11237
[2]Patent: CN107602452,2020,B .Location in patent: Paragraph 0076-0078

33
[ 13679-75-9 ]
[ 33831-72-0 ]
ethyl 2-phenyl-6-(thiophen-2-yl)nicotinate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In N,N-dimethyl-formamide; at 120℃; for 20h;Sealed tube;	1e (0.6 mmol, 84.1 mg), 2a (0.5 mmol, 95.6 mg), and Cu(OAc) were successively added to a 15 mL reaction tube2(0.05 mmol, 9.1 mg), 2,2'-bipyridine (0.1 mmol, 15.6 mg), TEMPO (0.5 mmol, 78.1 mg) and N,N-dimethylformamide (2 mL) in the presence of air The reaction tube was sealed and then placed in a 120C oil bath and stirred for 20 h.After completion of the reaction, the reaction mixture was quenched with water, extracted with ethyl acetate (8 mL×3), and the organic phase was washed with water and saturated brine in that order and dried over anhydrous sodium sulfate.Filtration, spin-drying, and column chromatography on silica gel (petroleum ether/ethyl acetate = 20/1) gave pale pink liquid product 3e (111 mg, 72%)

Reference： [1]Journal of Organic Chemistry,2017,vol. 82,p. 11230 - 11237
[2]Patent: CN107739332,2018,A .Location in patent: Paragraph 0036-0038

34
[ 13679-75-9 ]
[ 2835-77-0 ]
(4-phenylquinolin-3-yl)(thiophen-2-yl)methanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper diacetate; In toluene; at 120℃; for 36h;Inert atmosphere; Sealed tube;	To a 15 mL reaction tube was added 1a (0.5 mmol, 98.5 mg), toluene (3 mL)Cu (OAc) 2 (0.05 mmol,9.1 mg),2,2'-bipyridine (0.1 mmol, 15.6 mg), TEMPO (1 mmol, 156.2 mg) and 2d (0.6 mmol, 74.7 [mu] L). After the vacuum was purged with nitrogen, the reaction tube was sealed and placed in an oil bath at 120 C for 36 h. The reaction was stopped, 15 mL of dichloromethane was added, followed by washing with water and saturated NaCl solution successively, and the organic phase was dried over anhydrous MgSO4. Filter, spin dry,Separation by silica gel column (petroleum ether / ethyl acetate = 5/1)The target product 3f (141.8 mg, 90%) was obtained.

Reference： [1]Patent: CN106749020,2017,A .Location in patent: Paragraph 0071; 0072; 0073

35
[ 118-90-1 ]
[ 13679-75-9 ]
C₁₅H₁₄O₃S [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 4777 - 4782

36
[ 13679-75-9 ]
[ 67-56-1 ]
[ 36448-60-9 ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 6440 - 6445
[2]Angewandte Chemie - International Edition,2019,vol. 58,p. 775 - 779
Angew. Chem.,2019,vol. 131,p. 785 - 789,5

37
[ 13679-75-9 ]
[ 69626-39-7 ]
[ 100-46-9 ]
C₂₄H₂₁NOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	In 1,4-dioxane; at 120℃; under 760.051 Torr; for 12h;Inert atmosphere;	In the reaction tube by sequentially adding a 1 a (0.5 mmol, 72 mg), 2 a (0.6 mmol, 66 mul), 3 b (0.6 mmol, 83 mg) and 1, 4 - dioxane (3 ml), nitrogen (1 atm) atmosphere at 120 C stirring reaction 12 h. Then turns on lathe does solvent, too separating by silica gel column (petroleum ether/ethyl acetate=20/1) to be orange oily product 4 v (58 mg, 31%).

Reference： [1]Patent: CN108395380,2018,A .Location in patent: Paragraph 0105-0107

38
[ 13679-75-9 ]
[ 946122-05-0 ]
C₁₄H₈BrNOS [ No CAS ]

Reference： [1]RSC Advances,2018,vol. 8,p. 31455 - 31464

39
[ 13679-75-9 ]
[ 100-52-7 ]
[ 100-01-6 ]
(2S,3S)-2-methyl-3-((4-nitrophenyl)amino)-3-phenyl-1-(thiophen-2-yl)propan-1-one [ No CAS ]
2-methyl-3-((4-nitrophenyl)amino)-3-phenyl-1-(thiophen-2-yl)propan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With (S)-3,3'-bis(2,4,6-tri-iso-propylphenyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate; In chloroform; at 20℃; for 48h;Inert atmosphere;	General procedure: A solution of aniline 3 (0.25mmol), aldehyde 4 (0.25mmol), ketone 2 (1.25mmol, 5 equiv) and 1h (9.4mg, 0.0125mmol, 0.05 equiv) in CHCl3 (2.5mL) was stirred at rt for 48h. The reaction mixture was quenched with aqueous saturated NaHCO3 solution (10mL) and extracted with CH2Cl2 (3×10mL). The combined organic phases were washed with brine, dried over Na2SO4, filtered and the filtrate was concentrated in vacuo. Purification of the crude reaction mixture by flash column chromatography on silica gel (petroleum ether/EtOAc) afforded the three-component adduct 5

Reference： [1]Tetrahedron,2018,vol. 74,p. 5143 - 5149

40
[ 1072-97-5 ]
[ 13679-75-9 ]
(E)-3-((5-bromopyridin-2-yl)amino)-1-(thiophen-2-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper(I) oxide; tert.-butylhydroperoxide; 2,2,6,6-tetramethyl-piperidine-N-oxyl; In toluene; at 60℃; under 760.051 Torr; for 20h;Schlenk technique;	In an atmospheric oxygen atmosphere,1-(2-Thienyl)-1-propanone 1e (70.2 mg, 0.50 mmol) was sequentially added to a 15 mL Schlenk reaction tube.2-amino-5-bromopyridine 2e (69.2 mg, 0.40 mmol),Cuprous oxide (21.3 mg, 0.17 mmol),Tert-butyl hydroperoxide (182.2 mg, 2.0 mmol),2,2,6,6-tetramethylpiperidine oxide (1.6 mg, 0.01 mmol)And toluene (toluene, 2.0mL),The reaction was carried out at 60 C for 20 h,After the reaction is completed, it is cooled to room temperature.After suction filtration through diatomaceous earth,Concentration gave the crude product.The crude product was separated by chromatography on a prepared silica gel plate.The developing agent or eluent is petroleum ether and ethyl acetate.The volume ratio of petroleum ether to ethyl acetate is 50:1,Get product(E)-3-((5-bromopyridin-2-yl)amino)-1-(thiophen-2-yl)prop-2-en-1-one (3e),The product is a pale yellow solid.Product yield is 76%(100.0 mg).

Reference： [1]Patent: CN109796399,2019,A .Location in patent: Paragraph 0098-0104
[2]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3886 - 3892

41
[ 13679-75-9 ]
[ 164461-18-1 ]
3-(pyrene-1-yl)-1-(thiophene-2-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With copper(I) oxide; tert.-butylhydroperoxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In toluene; at 130℃; for 8h;Schlenk technique;	Under a one-pressure oxygen atmosphere, 2-propionylthiophene 1d (70.1 mg, 0.50 mmol), 1-pyreneboronic acid 2d (61.1 mg, 0.50 mmol), and cuprous oxide (7.0 mg, 0.05) were sequentially added to a 15 mL Schlenk reaction tube. mmol), tert-butyl hydroperoxide (182.2 mg, 2.0 mmol), 2,2,6,6-tetramethylpiperidine oxide (1.6 mg, 0.01 mmol) and toluene (toluene, 3.0 mL) at 130 The reaction was performed at 8 C for 8 hours. After the reaction, the reaction mixture was cooled to room temperature, filtered through celite, and concentrated to obtain a crude product. The crude product was separated by chromatography using a prepared silica gel plate. The developing agent or eluent was petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate was 50: 1. The product (E) -3- ( 3A, 3A-1-fluoren-1-yl) -1- (thien-2-yl) prop-2-en-1-one (3d), the product was a pale yellow solid, and the product yield was 50% (84.5mg ).

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3886 - 3892
[2]Patent: CN110194713,2019,A .Location in patent: Paragraph 0089-0095

42
[ 13679-75-9 ]
[ 13331-23-2 ]
[ 42811-86-9 ]

Yield	Reaction Conditions	Operation in experiment
59%	With copper(I) oxide; tert.-butylhydroperoxide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In toluene; at 60℃; for 20h;Schlenk technique;	Under an atmospheric oxygen atmosphere,To a 15 mL Schlenk reaction tube, 1- (2-thienyl) -1-acetone 1e (70.2 mg, 0.50 mmol),2-furan boronic acid 2e (44.7 mg, 0.40 mmol),Cuprous oxide (21.3mg, 0.17mmol),Tert-butyl hydroperoxide (182.2 mg, 2.0 mmol), 2,2,6,6-tetramethylpiperidine oxide (1.6 mg, 0.01 mmol) and toluene (toluene, 2.0 mL) were performed at 60 C. After 20h reaction, the reaction was cooled to room temperature, filtered through celite, and concentrated to obtain the crude product.The crude product was separated by chromatography using a prepared silica gel plate. The developing solvent or eluent was petroleum ether and ethyl acetate, and the volume ratio of petroleum ether and ethyl acetate was 20: 1. The product (E) -3- ( Furan-2-yl) -1- (thien-2-yl) prop-2-en-1-one (3e). The product was a pale yellow solid with a yield of 59% (60.2 mg).

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3886 - 3892
[2]Patent: CN110194713,2019,A .Location in patent: Paragraph 0096-0102

43
[ 552331-00-7 ]
[ 13679-75-9 ]
(E)-3-((4-iodopyridin-2-yl)amino)-1-(thiophen-2-yl)prop-2-en-1-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3886 - 3892

44
C₁₇H₂₉N₃O₇S [ No CAS ]
[ 4229-91-8 ]
[ 13679-75-9 ]
[ 54244-74-5 ]
[ 54411-07-3 ]
2-butyl-5-ethyl-thiophene [ No CAS ]
2-butyl-5-propylthiophene [ No CAS ]
2-sec-butyl-5-(1-methylbutyl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. phosphate buffer at 140℃; for 2h; Sealed tube;	2.2. Model reactions General procedure: The amounts of reactants used were GSH (0.30 mmol), glucose(0.30 mmol), and aldehyde (0.70 mmol, each). The reactants were weighed according to the respective systems and dissolved in 5 mL of phosphate buffer (0.2 M, pH 6.5) in a 15-mL pressure resistant tube.Then the tubes were sealed and heated at 140 °C while stirring for 0.16, 0.25, 0.5, 1, 2, 3, or 4 h. Two replicates were performed.

Reference： [1]Wang, Tianze; Zhen, Dawei; Tan, Jia; Xie, Jianchun; Cheng, Jie; Zhao, Jian [Food Chemistry, 2020, vol. 305]

45
C₂₂H₃₇N₅O₉S₂ [ No CAS ]
[ 4229-91-8 ]
[ 13679-75-9 ]
[ 54244-74-5 ]
[ 54411-07-3 ]
2-butyl-5-ethyl-thiophene [ No CAS ]
2-butyl-5-propylthiophene [ No CAS ]
2-sec-butyl-5-(1-methylbutyl)thiophene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In aq. phosphate buffer at 140℃; for 2h; Sealed tube;	2.2. Model reactions General procedure: The amounts of reactants used were GSH (0.30 mmol), glucose(0.30 mmol), and aldehyde (0.70 mmol, each). The reactants were weighed according to the respective systems and dissolved in 5 mL of phosphate buffer (0.2 M, pH 6.5) in a 15-mL pressure resistant tube.Then the tubes were sealed and heated at 140 °C while stirring for 0.16, 0.25, 0.5, 1, 2, 3, or 4 h. Two replicates were performed.

Reference： [1]Wang, Tianze; Zhen, Dawei; Tan, Jia; Xie, Jianchun; Cheng, Jie; Zhao, Jian [Food Chemistry, 2020, vol. 305]

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 13679-75-9 ]

Ketones

[ 59303-13-8 ]

1-(5-Methylthiophen-2-yl)propan-1-one

Similarity: 1.00

[ 832737-24-3 ]

1-(5-Propylthiophen-2-yl)ethanone

Similarity: 0.98

[ 79852-26-9 ]

1-(5-Methylthiophen-2-yl)butan-1-one

Similarity: 0.96

[ 30711-40-1 ]

1-(Thiophen-2-yl)heptan-1-one

Similarity: 0.96

[ 5333-83-5 ]

1-(Thiophen-2-yl)butan-1-one

Similarity: 0.96

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 13679-75-9 ] {[proInfo.proName]}

Quality Control of [ 13679-75-9 ]

Related Doc. of [ 13679-75-9 ]

Product Details of [ 13679-75-9 ]

Calculated chemistry of [ 13679-75-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 13679-75-9 ]

Application In Synthesis of [ 13679-75-9 ]

[ 13679-75-9 ] Synthesis Path-Upstream 1~2

[ 13679-75-9 ] Synthesis Path-Downstream 1~45

Related Functional Groups of [ 13679-75-9 ]

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 13679-75-9 ]