Name: 10139-84-1|1-(2,4-Dihydroxy-3-methylphenyl)ethanone|95+%
Brand: Ambeed
SKU: A969493
Rating: 94 (40 reviews)

1
[ 10139-84-1 ]
[ 36889-02-8 ]

Yield	Reaction Conditions	Operation in experiment
57%	With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran for 3h; Reflux;
	With hydrogenchloride; amalgamated zinc
	With hydrogenchloride; acetic acid; zinc at 80 - 85℃; for 1h;

Reference： [1]Milzarek, Tobias M.; Einsiedler, Manuel; Aldemir, Hülya; D'Agostino, Paul M.; Evers, Julia K.; Hertrampf, Gesa; Lamm, Katharina; Malay, Mert; Matura, Anke; Müller, Jonas I.; Gulder, Tobias A. M. [Organic Letters, 2019, vol. 21, # 12, p. 4520 - 4524]
[2]Brown et al. [Journal of the Chemical Society, 1951, p. 2019]
[3]Herron, David K.; Goodson, Theodore; Bollinger, Nancy G.; Swanson-Bean, Dorothy; Wright, Ian G.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 10, p. 1818 - 1828]

2
[ 1056477-06-5 ]
[ 10139-84-1 ]
[ 116719-55-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium carbonate In acetone for 8h; Heating;
60%	With potassium carbonate In acetone for 8h; Heating;
60%	With potassium carbonate In acetone for 12h; Heating;

43%

With potassium carbonate In acetone Heating;

Reference： [1]Soman; Trivedi [Journal of the Indian Chemical Society, 1990, vol. 67, # 12, p. 997 - 999]
[2]Soman, Shubhangi S. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2004, vol. 43, # 3, p. 624 - 628]
[3]Patel, Jagdish M.; Soman, Shubhangi S. [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 945 - 949]
[4]Ahluwalia, V. K.; Adhikari, R.; Singh, R. P. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1988, vol. 27, # 1-12, p. 274 - 276]

3
[ 608-25-3 ]
[ 108-24-7 ]
[ 10139-84-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	With boron trifluoride diethyl etherate at 80℃; for 6h;
95%	Stage #1: 2-methylbenzene-1,3-diol With boron trifluoride diethyl etherate at 70℃; Stage #2: acetic anhydride at 20 - 80℃; for 7h;
85%	Stage #1: 2-methylbenzene-1,3-diol With boron trifluoride diethyl etherate at 70℃; Stage #2: acetic anhydride at 80℃; for 6h;

83%	With boron trifluoride diethyl etherate at 75℃; for 6h;
78%	at 70 - 80℃; for 6h;
73%	With zinc(II) chloride at 150 - 160℃; for 3.5h;	55a A mixture of 2-methyl-benzene-1, 3-diol, acetic anhydride and ZnCl2 was heated at 150- 60°C for 3. 5h, and processed as reported in the literature. (Pearson. D. E. et. al. , Synthesis, 533, 1972 and the references cited therein). The crude was purified using flash chromatography (silica gel, 0-5% CH3CN in chloroform) to obtain the title compound. Yield, 73%; mp, 65-66°C (EtOAc- PE 60-80°C) ; MS (CI) : 195 (M++29), 169 (M++1) ; analysis: C9H10O3 requires C, 65.05 ; H, 6.07 ; found C, 65.44 ; H, 6.62%.
73%	With zinc(II) chloride at 150 - 160℃; for 3.5h;	55.a Example 55a 1-(2,4-Dihydroxy-3-methyl-phenyl)-ethanone A mixture of 2-methyl-benzene-1,3-diol, acetic anhydride and ZnCl2 was heated at 150-60° C. for 3.5 h, and processed as reported in the literature. (Pearson. D. E. et. al., Synthesis, 533, 1972 and the references cited therein). The crude was purified using flash chromatography (silica gel, 0-5% CH3CN in chloroform) to obtain the title compound. Yield, 73%; mp, 65-66° C. (EtOAc-PE 60-80° C.); MS (CI): 195 (M++29), 169 (M++1); analysis: C9H10O3 requires C, 65.05; H, 6.07; found C, 65.44; H, 6.62%.

Reference： [1]Heckrodt, Thilo J.; Mulzer, Johann [Synthesis, 2002, # 13, p. 1857 - 1866]
[2]Li, Ren-Shi; Wang, Xiao-Bing; Hu, Xiao-Jun; Kong, Ling-Yi [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2636 - 2641]
[3]Milzarek, Tobias M.; Einsiedler, Manuel; Aldemir, Hülya; D'Agostino, Paul M.; Evers, Julia K.; Hertrampf, Gesa; Lamm, Katharina; Malay, Mert; Matura, Anke; Müller, Jonas I.; Gulder, Tobias A. M. [Organic Letters, 2019, vol. 21, # 12, p. 4520 - 4524]
[4]Carter, Rachel H.; Garson, Mary J.; Hill, Robert A.; Staunton, James; Sunter, David C. [Journal of the Chemical Society. Perkin transactions I, 1981, p. 471 - 479]
[5]Raphael, Ralph A.; Ravenscroft, Paul [Journal of the Chemical Society. Perkin transactions I, 1988, p. 1823 - 1828]
[6]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - WO2005/35495, 2005, A2 Location in patent: Page/Page column 112
[7]Current Patent Assignee: PIRAMAL ENTERPRISES LIMITED - US7759387, 2010, B2 Location in patent: Page/Page column 97

4
[ 10139-84-1 ]
[ 100-44-7 ]
[ 73640-74-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; potassium iodide In acetone at 56℃;
81%	With potassium carbonate; potassium iodide In acetone for 18h; Heating;

Reference： [1]Gammon, David W.; Hunter, Roger; Wilson, Seanette A. [Tetrahedron, 2005, vol. 61, # 45, p. 10683 - 10688]
[2]Raphael, Ralph A.; Ravenscroft, Paul [Journal of the Chemical Society. Perkin transactions I, 1988, p. 1823 - 1828]

5
[ 95-71-6 ]
[ 64-19-7 ]
[ 10139-84-1 ]

Yield	Reaction Conditions	Operation in experiment
59%	With zinc(II) chloride at 80 - 90℃; for 5h;

Reference： [1]Herron, David K.; Goodson, Theodore; Bollinger, Nancy G.; Swanson-Bean, Dorothy; Wright, Ian G.; et al. [Journal of Medicinal Chemistry, 1992, vol. 35, # 10, p. 1818 - 1828]

6
[ 10139-84-1 ]
[ 75-36-5 ]
[ 144224-86-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With triethylamine In dichloromethane at 0 - 20℃;

Reference： [1]Morris, Joel; Wishka, Donn G.; Lin, Alice H.; Humphrey, William R.; Wiltse, Ann L.; et al. [Journal of Medicinal Chemistry, 1993, vol. 36, # 14, p. 2026 - 2032]

7
[ 10139-84-1 ]
[ 77-78-1 ]
[ 60512-80-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In acetone for 48h; Heating;

Reference： [1]Carter, Rachel H.; Garson, Mary J.; Hill, Robert A.; Staunton, James; Sunter, David C. [Journal of the Chemical Society. Perkin transactions I, 1981, p. 471 - 479]

8
[ 10139-84-1 ]
[ 4407-36-7 ]
[ 112776-93-9 ]

Yield	Reaction Conditions	Operation in experiment
70%	With phosphoric acid In benzene 1) 80-85 deg C, 6h, 2) 12 h;

Reference： [1]Ahluwalia, V. K.; Nayal, Lalita; Kalia, Neelu; Bala, Shashi; Tehim, A. K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1987, vol. 26, # 1-12, p. 384 - 386]

9
[ 110-87-2 ]
[ 10139-84-1 ]
[ 200726-78-9 ]

Yield	Reaction Conditions	Operation in experiment
83%	With toluene-4-sulfonic acid In diethyl ether Ambient temperature;
	With toluene-4-sulfonic acid In diethyl ether at 20℃; for 3h;	2.A 1-[2-hydroxy-3-methyl-4-[(tetrahydro-2H-pyran-2-yl)oxy]] phenyl ethanone A mixture containing 200 g of 1-[2,4-dihydroxy-3-methyl] phenyl ethanone and 1.2 l of ethyl ether is cooled down to 8° C. 200 ml of dihydro-2H-pyran and 1 g of PTSA are added. The reaction medium is left to return to ambient temperature. Agitation is carried out for 3 hours and 253 mg of PTSA is added. The product obtained is poured into 400 ml of a molar aqueous solution of potassium acid phosphate, followed by decanting, washing with water and drying. After evaporation 302.5 g of crude sought product is obtained which is purified thus: the product is diluted in 2 l of methylene chloride, the organic phase is washed with ammonium hydroxide diluted to one tenth, then with brine, dried, filtered and evaporated to dryness. 272.55 g of sought product is obtained.

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]
[2]Current Patent Assignee: ASTRAZENECA PLC - US6350733, 2002, B1 Location in patent: Page column 7-8

10
[ 10139-84-1 ]
[ 106-95-6 ]
[ 77036-77-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In acetone at 20℃; for 32h;

Reference： [1]Jabin, Ivan; Heindel, Ned D.; Rapp, Roben D.; Laskin, Jeffrey D. [Journal of Heterocyclic Chemistry, 2000, vol. 37, # 1, p. 31 - 39]

11
[ 10139-84-1 ]
[ 100-39-0 ]
[ 73640-74-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	Stage #1: 1-(2,4-dihydroxy-3-methylphenyl)ethanone With potassium carbonate; potassium iodide In acetone at 50℃; for 0.5h; Stage #2: benzyl bromide In acetone for 5h; Reflux;
	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 16h;

Reference： [1]Hartmann, Markus; Huber, Jessica; Kramer, Jan S.; Heering, Jan; Pietsch, Larissa; Stark, Holger; Odadzic, Dalibor; Bischoff, Iris; Fürst, Robert; Schröder, Martin; Akutsu, Masato; Chaikuad, Apirat; Dötsch, Volker; Knapp, Stefan; Biondi, Ricardo M.; Rogov, Vladimir V.; Proschak, Ewgenij [Journal of Medicinal Chemistry, 2021, vol. 64, # 7, p. 3720 - 3746]
[2]Chiosis, Gabriela; Rosen, Neal; Sepp-Lorenzino, Laura [Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 7, p. 909 - 913]

12
[ 10139-84-1 ]
[ 77-78-1 ]
[ 69469-91-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate In acetone at 20℃; for 17h;
	With potassium carbonate In acetone Heating;

Reference： [1]Heckrodt, Thilo J.; Mulzer, Johann [Synthesis, 2002, # 13, p. 1857 - 1866]
[2]Soman, Shubhangi S.; Patel; Jethawa, Komal B.; Baloni, Radhika [Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 233 - 236]

13
[ 10139-84-1 ]
[ 75-03-6 ]
[ 536723-94-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With potassium carbonate In acetone for 5h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Carrieri, Antonio; Grossi, Giancarlo; Leoncini, Giuliana; Grazia Signorello, Maria; Carotti, Angelo [Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 1, p. 123 - 138]

14
[ 75-30-9 ]
[ 10139-84-1 ]
[ 714960-83-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	With potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

15
[ 542-69-8 ]
[ 10139-84-1 ]
[ 714960-85-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

16
[ 620-19-9 ]
[ 10139-84-1 ]
[ 714960-90-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

17
[ 10139-84-1 ]
[ 34334-24-2 ]
[ 664376-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate In acetone at 45℃;

Reference： [1]Pinkerton, Anthony B.; Vernier, Jean-Michel; Schaffhauser, Hervé; Rowe, Blake A.; Campbell, Una C.; Rodriguez, Dana E.; Lorrain, Daniel S.; Baccei, Christopher S.; Daggett, Lorrie P.; Bristow, Linda J. [Journal of Medicinal Chemistry, 2004, vol. 47, # 18, p. 4595 - 4599] Pinkerton, Anthony B.; Cube, Rowena V.; Hutchinson, John H.; Rowe, Blake A.; Schaffhauser, Hervé; Zhao, Xiumin; Daggett, Lorrie P.; Vernier, Jean-Michel [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5329 - 5332]

18
[ 10139-84-1 ]
[ 3747-74-8 ]
[ 714961-06-5 ]

Reference： [1]European Journal of Medicinal Chemistry,2004,vol. 39,p. 397 - 409

19
[ 10139-84-1 ]
[ 1822-51-1 ]
[ 714961-04-3 ]

Yield	Reaction Conditions	Operation in experiment
43%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

20
[ 10139-84-1 ]
[ 6959-47-3 ]
[ 714961-00-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

21
[ 10139-84-1 ]
[ 6959-48-4 ]
[ 714961-02-1 ]

Yield	Reaction Conditions	Operation in experiment
41%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

22
[ 10139-84-1 ]
[ 552-45-4 ]
[ 714960-88-0 ]

Yield	Reaction Conditions	Operation in experiment
46%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

23
[ 10139-84-1 ]
[ 104-83-6 ]
[ 714960-94-8 ]

Yield	Reaction Conditions	Operation in experiment
64%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

24
[ 10139-84-1 ]
[ 107-08-4 ]
[ 714960-81-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

25
[ 10139-84-1 ]
[ 38661-81-3 ]
[ 714960-96-0 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

26
[ 10139-84-1 ]
[ 103-63-9 ]
[ 714960-97-1 ]

Yield	Reaction Conditions	Operation in experiment
20%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

27
[ 10139-84-1 ]
[ 824-94-2 ]
[ 714960-92-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

28
[ 10139-84-1 ]
[ 2550-36-9 ]
[ 714960-87-9 ]

Yield	Reaction Conditions	Operation in experiment
18%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

29
[ 10139-84-1 ]
[ 86-52-2 ]
[ 714960-99-3 ]

Yield	Reaction Conditions	Operation in experiment
55%	With potassium hydroxide; potassium carbonate In butanone for 6h; Heating;

Reference： [1]Di Braccio, Mario; Grossi, Giancarlo; Roma, Giorgio; Signorello, Maria Grazia; Leoncini, Giuliana [European Journal of Medicinal Chemistry, 2004, vol. 39, # 5, p. 397 - 409]

30
[ 10139-84-1 ]
[ 86604-75-3 ]
[ 942133-84-8 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium hydroxide; potassium carbonate In butanone for 5h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

31
[ 2373-51-5 ]
[ 10139-84-1 ]
[ 942133-87-1 ]

Yield	Reaction Conditions	Operation in experiment
32%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

32
[ 10139-84-1 ]
[ 3188-13-4 ]
[ 942133-88-2 ]

Yield	Reaction Conditions	Operation in experiment
54%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

33
[ 542-81-4 ]
[ 10139-84-1 ]
[ 942133-89-3 ]

Yield	Reaction Conditions	Operation in experiment
33%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

34
[ 10139-84-1 ]
[ 4584-46-7 ]
1-[4-[2-(dimethylamino)ethoxy]-2-hydroxy-3-methylphenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

35
[ 10139-84-1 ]
[ 869-24-9 ]
1-[4-[2-(diethylamino)ethoxy]-2-hydroxy-3-methylphenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

36
[ 10139-84-1 ]
[ 7250-67-1 ]
1-[2-hydroxy-3-methyl-4-[2-(1-pyrrolidinyl)ethoxy]phenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

37
[ 10139-84-1 ]
[ 2008-75-5 ]
[ 942133-94-0 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

38
[ 10139-84-1 ]
[ 3647-69-6 ]
1-[2-hydroxy-3-methyl-4-(2-morpholinoethoxy)phenyl]ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

39
[ 19853-09-9 ]
[ 10139-84-1 ]
[ 942133-96-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium hydroxide; potassium carbonate In butanone for 5h; Heating;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

40
[ 10139-84-1 ]
[ 66496-82-0 ]
[ 942133-90-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With potassium carbonate In various solvent(s) at 160℃; for 16h;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

41
[ 10139-84-1 ]
[ 622-86-6 ]
[ 942133-97-3 ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium carbonate at 160℃; for 16h;

Reference： [1]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

42
[ 10139-84-1 ]
[ 107-30-2 ]
[ 942133-85-9 ]

Yield	Reaction Conditions	Operation in experiment
94%	With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;	16 4.16 1-(2-Hydroxy-4-(methoxymethoxy))-3-methylacetophenone (25) 1-(2,4-Dihydroxy-3-methylphenyl)ethanone (6.00 g, 36.1 mmol) (24) was dissolved in DCM (110 mL, 0.330 M) to give an orange solution. DIPEA (15.9 mL, 95.5 mmol) was added causing the solution to turn a deep red color. Technical grade MOMCl (5.50 mL) was added, at, which time the solution turned yellow. The solution was allowed to stir at RT for 18 h before being quenched with H2O. The aqueous layer was extracted with DCM (2*30 mL). The organic fractions were washed once each with NaHCO3, brine, then dried over MgSO4 and concentrated. The crude product was purified by Biotage flash column chromatography, eluting with 30% EtOAc-Hexanes on a 100 g cartridge to afford (25) (7.14 g, 34.0 mmol, 94%) as white needles. Mp 47.5-49.5 °C; 1H NMR (300 MHz, CDCl3): δ 7.57 (d, J=9.1 Hz, 1H, H-6), 6.65 (d, J=9.1 Hz, 1H, H-5), 5.26 (s, 2H, OCH2), 3.48 (s, 3H, OCH3), 2.57 (s, 3H, COCH3), 2.13 (s, 3H, CH3); 13C NMR (75 MHz, CDCl3) δ 203.2, 162.5, 161.3, 129.6, 114.8, 105.0, 105.0, 94.2, 56.4, 26.4, 7.8; IR (neat, cm-1): 2969.0, 2918.4, 1607.0, 1254.8, 1069.5, 798.9; Anal. Calcd for C11H14O4: C, 62.85; H, 6.71, found: C, 62.81; H, 6.81; HRMS (EI) (m/z): [(M+H)+] calcd for C11H14O4 210.0892, found, 210.0897.
91%	With potassium carbonate In acetone at 20℃; for 1.5h; Cooling with ice;	6.1.1. 1-(2-Hydroxy-4-(methoxymethoxy)-3-methylphenyl)ethanone (39) Chloromethyl methyl ether (9.14 mL, 120 mmol) was added dropwise into a mixture of 38 (10.0 g, 60.2 mmol) and potassium carbonate (20.8 g, 150 mmol) in anhydrous acetone (60 mL) in an ice-bath. The reaction mixture was then allowed to warm to room temperature and stirred for 1.5 h. The mixture was then filtered, and the filtrate was dissolved in brine and extracted with EtOAc (35 mL). The organic layer was dried in vacuo to provide 39 (13.9 g) as brown oil: 91% yield. 1H NMR δ: 2.14 (3H, s, 3-CH3), 2.56 (3H, s, 1-COCH3), 3.50 (3H, s, 4-OCH2OCH3), 5.27 (2H, s, 4-OCH2OCH3), 6.65 (1H, d, J = 8.7 Hz, 6-H), 7.57 (1H, d, J = 8.7 Hz, 5-H), 12.80 (1H, s, 2-OH). ESI-MS m/z 209 (M+ - 1).
91%	With potassium carbonate In acetone at 20℃; Cooling with ice; chemoselective reaction;	6.5. 1-(2-Hydroxy-4-(methoxymethoxy)-3-methylphenyl)ethanone (46b) Chloromethyl methyl ether (9.14 mL, 120 mmol) was added dropwise into a mixture of 45b (10.0 g, 60.2 mmol) and potassium carbonate (20.8 g, 150 mmol) in anhydrous acetone (60 mL) in an ice-bath. The reaction mixture was allowed to warm to rt and stirred for 1.5 h. The mixture was then filtered, and the filtrate was dissolved in brine and extracted with EtOAc (35 mL). The organic layer was dried in vacuo to provide 46b (13.9 g) as brown oil, 91% yield. 1H NMR δ 2.14 (3H, s, 3-CH3), 2.56 (3H, s, 1-COCH3), 3.50 (3H, s, 4-OCH2OCH3), 5.27 (2H, s, 4-OCH2OCH3), 6.65 (1H, d, J = 8.7 Hz, 6-H), 7.57 (1H, d, J = 8.7 Hz, 5-H), 12.80 (1H, s, 2-OH). ESI MS m/z 209 (M+ - 1).

60%

With potassium hydroxide; potassium carbonate In butanone for 16h; Heating;

Reference： [1]Brandt, Drew R.; Pannone, Kristina M.; Romano, Joseph J.; Casillas, Eduard G. [Tetrahedron, 2013, vol. 69, # 47, p. 9994 - 10002]
[2]Location in patent: experimental part Chen, Ying; Cheng, Ming; Liu, Fa-Qiang; Xia, Peng; Qian, Keduo; Yu, Donglei; Xia, Yi; Yang, Zheng-Yu; Chen, Chin-Ho; Morris-Natschke, Susan L.; Lee, Kuo-Hsiung [European Journal of Medicinal Chemistry, 2011, vol. 46, # 10, p. 4924 - 4936]
[3]Location in patent: experimental part Chen, Ying; Liu, Hong-Rui; Liu, Hong-Shan; Cheng, Ming; Xia, Peng; Qian, Keduo; Wu, Pei-Chi; Lai, Chin-Yu; Xia, Yi; Yang, Zheng-Yu; Morris-Natschke, Susan L.; Lee, Kuo-Hsiung [European Journal of Medicinal Chemistry, 2012, vol. 49, p. 74 - 85]
[4]Roma, Giorgio; Di Braccio, Mario; Grossi, Giancarlo; Piras, Daniela; Leoncini, Giuliana; Bruzzese, Debora; Signorello, Maria Grazia; Fossa, Paola; Mosti, Luisa [Journal of Medicinal Chemistry, 2007, vol. 50, # 12, p. 2886 - 2895]

43
[ 10139-84-1 ]
[ 78-95-5 ]
1-(4-acetyl-3-hydroxy-2-methylphenoxy)-propan-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With potassium carbonate; potassium iodide In acetone for 12h; Heating;

Reference： [1]Patel, Jagdish M.; Soman, Shubhangi S. [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 945 - 949]

44
[ 10139-84-1 ]
[ 70-11-1 ]
2-(4-acetyl-3-hydroxy-2-methylphenoxy)-1-phenyl-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With potassium carbonate In acetone for 12h; Heating;

Reference： [1]Patel, Jagdish M.; Soman, Shubhangi S. [Journal of Heterocyclic Chemistry, 2007, vol. 44, # 4, p. 945 - 949]

45
[ 10139-84-1 ]
[ 103503-16-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 88 percent / potassium carbonate; potassium iodide / acetone / 56 °C 2: 76 percent / sodium hydride / toluene / 2 h / 110 °C 3: 93 percent / sulphuric acid; nitric acid / CHCl₃ / 1 h / 20 °C 4: 86 percent / zinc / 1 h / Heating 5: 87 percent / phosphorus oxychloride; pyridine / tetrahydrofuran / 0.17 h / 66 °C 6: 74 percent / hydrogen / palladium on carbon / tetrahydrofuran; CH₂Cl₂ / 3 h / 20 °C

Reference： [1]Gammon, David W.; Hunter, Roger; Wilson, Seanette A. [Tetrahedron, 2005, vol. 61, # 45, p. 10683 - 10688]

46
[ 10139-84-1 ]
1-(2-hydroxy-3-methyl-4-{4-[4-(2H-tetrazol-5-yl)-phenoxy]-butoxy}-phenyl)-ethanone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: K₂CO₃ / acetone / 45 °C 2: trimethylsilyl azide; Bu₂SnO / toluene / Heating
	Multi-step reaction with 2 steps 1: K₂CO₃ / acetone / 45 °C 2: Me₃SiN₃; Bu₂SnO / toluene / Heating

Reference： [1]Pinkerton, Anthony B.; Cube, Rowena V.; Hutchinson, John H.; Rowe, Blake A.; Schaffhauser, Hervé; Zhao, Xiumin; Daggett, Lorrie P.; Vernier, Jean-Michel [Bioorganic and Medicinal Chemistry Letters, 2004, vol. 14, # 21, p. 5329 - 5332]
[2]Pinkerton, Anthony B.; Vernier, Jean-Michel; Schaffhauser, Hervé; Rowe, Blake A.; Campbell, Una C.; Rodriguez, Dana E.; Lorrain, Daniel S.; Baccei, Christopher S.; Daggett, Lorrie P.; Bristow, Linda J. [Journal of Medicinal Chemistry, 2004, vol. 47, # 18, p. 4595 - 4599]

47
[ 10139-84-1 ]
[ 200727-03-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: 95 percent / TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

48
[ 10139-84-1 ]
5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-5-hydroxy-6-(4-hydroxy-3-{1-[(E)-methoxyimino]-ethyl}-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: 95 percent / TosOH / methanol / Ambient temperature 10: 73 percent / KOAc / ethanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

49
[ 10139-84-1 ]
5-methyl-1H-pyrrol-2-carboxylic acid 3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: 82 percent / DMAP / CH₂Cl₂ / Ambient temperature 9: NH₃ (g) / tetrahydrofuran / Ambient temperature 10: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

50
[ 10139-84-1 ]
[ 200726-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

51
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid-3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-3-[(methylthio)acetyl]-2H-1-benzopyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

52
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid-3'-ester of ethyl 7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: 82 percent / DMAP / CH₂Cl₂ / Ambient temperature 9: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

53
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 5-hydroxy-6-(4-hydroxy-3-methoxycarbamoyl-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: 82 percent / DMAP / CH₂Cl₂ / Ambient temperature 9: pyridine / tetrahydrofuran / Ambient temperature 10: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

54
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid-3'-ester of 2-methylpropyl 7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-4-hydroxy-8-methyl-2-oxo-2H-1-benzopyran-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

55
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid-3'-ester of 7-[(6-deoxy-5-C-methyl-4-O-methyl-alpha-L-lyxo-hexopyranosyl)oxy]-3-(ethoxyacetyl)-4-hydroxy-8-methyl-2H-1-benzopyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

56
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 6-(3-ethoxyoxalyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: TosOH / methanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

57
[ 10139-84-1 ]
5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-6-(3-{ethoxycarbonyl-[(Z)-methoxyimino]-methyl}-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-5-hydroxy-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: TosOH / methanol / Ambient temperature 10: KOAc / ethanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

58
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 6-(3-acetyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

59
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 6-(3-carbamoyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: 82 percent / DMAP / CH₂Cl₂ / Ambient temperature 9: NH₃ (g) / tetrahydrofuran / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

60
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 6-(4-hydroxy-3-methoxycarbamoyl-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 9 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: 82 percent / DMAP / CH₂Cl₂ / Ambient temperature 9: pyridine / tetrahydrofuran / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

61
[ 10139-84-1 ]
[ 200727-68-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: 82 percent / DMAP / CH₂Cl₂ / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

62
[ 10139-84-1 ]
[ 200726-94-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

63
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 6-(4-hydroxy-3-isobutoxycarbonyl-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

64
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 5-hydroxy-6-(4-hydroxy-3-{1-[2-(1H-imidazol-2-ylsulfanyl)-ethoxyimino]-ethyl}-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: 95 percent / TosOH / methanol / Ambient temperature 10: KOAc / ethanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

65
[ 10139-84-1 ]
[ 200726-96-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

66
[ 10139-84-1 ]
5-Methyl-1H-pyrrole-2-carboxylic acid (3R,4S,5R,6R)-5-hydroxy-6-(4-hydroxy-8-methyl-3-{1-[(E)-2-morpholin-4-yl-ethoxyimino]-ethyl}-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 10 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature 9: 95 percent / TosOH / methanol / Ambient temperature 10: KOAc / ethanol / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

67
[ 10139-84-1 ]
5-methyl-1H-pyrrole-2-carboxylic acid 6-(3-ethoxyoxalyl-4-hydroxy-8-methyl-2-oxo-2H-chromen-7-yloxy)-3-methoxy-2,2-dimethyl-5-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1: 83 percent / TosOH / diethyl ether / Ambient temperature 2: 91 percent / NaH / toluene / Heating 3: 55 percent / dimethylformamide / 65 °C 4: 90 percent / HCl / methanol; CH₂Cl₂ / Ambient temperature 5: 54 percent / PPh₃, EtO₂CN=NCO₂Et / CH₂Cl₂ / Ambient temperature 6: 98 percent / TosOH / diethyl ether / Ambient temperature 7: 100 percent / H₂ / 10 percent Pd/C / tetrahydrofuran 8: DMAP / CH₂Cl₂ / Ambient temperature

Reference： [1]Laurin, Patrick; Ferroud, Didier; Klich, Michel; Dupuis-Hamelin, Claudine; Mauvais, Pascale; Lassaigne, Patrice; Bonnefoy, Alain; Musicki, Branislav [Bioorganic and Medicinal Chemistry Letters, 1999, vol. 9, # 14, p. 2079 - 2084]

68
[ 888968-82-9 ]
[ 10139-84-1 ]
5-(3-((4-acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio)-nicotinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: 5-(3-(hydroxymethyl)phenylthio)picolinonitrile; 1-(2,4-dihydroxy-3-methylphenyl)ethanone With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran for 24h; Stage #2: With water In tetrahydrofuran	160 Add triphenylphosphine (5.24 g, 20.0 mmol) and diisopropylazodicarboxylate (4.04 g, 20.0 mmol) to a solution of 5-(3-(hydroxymethyl)phenylthio)mcotinomtrile (4.84 g, 20.0 mmol) and l-(2,4-dihydroxy-3-methylphenyl)ethanone (3.32 g, 20.0 mmol) in THF (100 mL). Stir the reaction for 24 h. Quench the reaction with water and extract with EtOAc. Dry, filter and concentrate. Purify the residue by flash chromatography on silica gel eluting with a mixture of EtOAc and hexanes (15:85 to 20:80) to give an off- white solid. Recrystallize the solid from a mixture of EtOAc and hexanes to afford the title compound (3.94 g, 50%): 1H NMR (CDCl3) δ 2.14 (s, 3 H), 2.57 (s, 3 H), 5.18 (s, 2 H), 6.44 (d, J= 9.0 Hz, 1 H), 7.46-7.49 (m, 3 H), 7.52 (s, 1 H), 7.59 (d, J= 9.0 Hz, 1 H), 7.62-7.63 (m, 1 H), 8.63-8.64 (m, 2 H), 12.78 (s, 1 H).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2006/57860, 2006, A1 Location in patent: Page/Page column 137-138

69
[ 888968-82-9 ]
[ 10139-84-1 ]
5-(3-((4-acetyl-3-hydroxy-2-methylphenoxy)methyl)phenylthio)picolinonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran	166 Add triphenylphosphine (1.84 g, 7.02 mmol) and diisopropylazodicarboxylate (1.42 g, 7.02 mmol) to a solution of 5-(3-(hydroxymethyl)phenylthio)picolinonitrile (1.70 g, 7.02 mmol) and l-(2,4-dihydroxy-3-methylphenyl)ethanone (1.17 g, 7.02 mmol) in THF (35.I mL). Stir overnight. Dilute with, ethyl acetate. Wash the mixture with water and brine. Dry, filter and concentrate to afford the title compound (2.00 g, 73%). Use as is. MS (APCI-neg) m/z (rel intensity): 390 (M+H, 100%).

Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2006/57860, 2006, A1 Location in patent: Page/Page column 139-140

70
[ 5683-33-0 ]
[ 10139-84-1 ]
[ 130737-48-3 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane;	Part A: Preparation of 2'-Hydroxy-3'-methyl-4'-trifluormethanesulfonyloxy-acetophenone. 2',4'-Dihydroxy-3'methyl-acetophenone (11 g, 60.2 mmole) is suspended in 300 ml dichloromethane in a 1000 ml one neck round bottom flask under nitrogen. The suspension is treated successively with pyridine (4.4 ml, 54 mmole) and N,N, dimethylamino-pyridine (730 mg, 6 mmole) and the solution is cooled to 0 C. Triflic anhydride (11 ml, 66.2 mmole), in 1100 ml dichloromethane, is added slowly dropwise to the reaction mixture (30 min). The reaction is stirred for 1 h at room temperature for 1 h and the mixture is washed with 2200 ml 5% hydrochloric acid. The organics are dried over magnesium sulfate and are concentrated in vacuo to a yellow oil. The oil is distilled via kugelrhor under high vacuum (165 C) to provide 16.4 (91%) of triflate as a white solid. Melting Point: 60-64 C.

Reference： [1]Patent: US5703075,1997,A

71
[ 608-25-3 ]
[ 10139-84-1 ]

Yield	Reaction Conditions	Operation in experiment
88.4%	In (2S)-N-methyl-1-phenylpropan-2-amine hydrate	2.1 (1) (1) 2,4-Dihydroxy-3-methylacetophenone A mixture prepared by adding 294 g. of boron trifluoride-acetic acid complex to 124 g. of 2-methyl resorcinol was stirred at 100°-105° C. for 3 hours. The reaction solution was poured into 2 l of ice water and crystals precipitated out were recovered by filtration. The crystals recovered were washed with water and recrystallized from ethanol (150 ml)/water (50 ml) to obtain 146.8 g. (yield: 88.4%) of the subject compound. Melting point: 155°-156° C.

Reference： [1]Current Patent Assignee: EISAI CO LTD; TOKYO GIAPPONE - US4208426, 1980, A

72
[ 10139-84-1 ]
[ 109-70-6 ]
[ 937025-81-5 ]

Yield	Reaction Conditions	Operation in experiment
82%	With potassium carbonate In acetone for 24h; Reflux;	7 4-(3-Chloropropoxy)-3-methyl-2-hydroxyacetophenone 3-methyl-2,4-dihydroxyacetophenone (0.3 g) and potassium carbonate (0.5 g) were refluxed for 30 min in acetone. Then, the flask was cooled and 1-bromo-3-chloro-propane (0.3 ml) was added. Then, the mixture was refluxed for 24 hours. The product was purified on column chromatography by using ethyl acetate/heptane as an eluent (EtOAc/Hept=20/80). Yield 82%.

Reference： [1]Current Patent Assignee: UNIVERSITY OF STRASBOURG; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE - US7880021, 2011, B2 Location in patent: Page/Page column 16

73
[ 10139-84-1 ]
[ 100-39-0 ]
[ 1310708-26-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3h;

Reference： [1]Smith, Marcus J.; Nawrat, Christopher C.; Moody, Christopher J. [Organic Letters, 2011, vol. 13, # 13, p. 3396 - 3398]

74
C₁₃H₉Cl₂Pol [ No CAS ]
[ 10139-84-1 ]
C₂₂H₁₈ClO₃Pol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere; Automated synthesizer; solid phase reaction;	4.1.1. General procedure for the solid-phase synthesis of 2'-hydroxychalcones and flavanones (1-33) General procedure: In a 24 reaction vessels of Büchi Syncore synthesizer a mixtureof 2'-hydroxyacetophenones (10 mmol), DIEA (2 mmol) and 2-chlorotritylchloride resin (1.0-1.5 mmol Cl/g) in anhydrous CH2Cl2/DMF (3:0.5 mL) was stirred at room temperature under nitrogen atmosphere for 48 h to provide the solid-supported acetophenones.These immobilized acetophenones were washed with anhydrous THF (2 × 3 mL), anhydrous MeOH (3 × 3 mL) and anhydrous CH2Cl2 (4 × 3 mL) and dried under vacuum for 24 h. To the solid-supported acetophenones (1 mmol) were added the appropriate benzaldehydes (10 mmol), a solution of 4% NaOH in anhydrous MeOH (2 mmol) and anhydrous THF (3 mL). The reaction mixture was gentle stirred at room temperature under nitrogen atmosphere for 48 h to give the solid-supported chalcones. These immobilized chalcones were washed and dried in the same sequence as the first step described above. The solid-supported chalcones were exposed to 2% TFA in CH2Cl2 at room temperature under nitrogen atmosphere for 30 min. The cleaved 2-chlorotrityl resin was filtered and washed with 2% TFA:CH2Cl2 (2 × 1 mL) and CH2Cl2 (5 × 3 mL) and the solvent was evaporated under reduced pressure. The resulting residue was then purified by flash chromatography cartridges (SiO2, n-hexane:EtOAc) to afford the 2'-hydroxychalcones 1-31 and flavanones 32 and 33.

Reference： [1]Location in patent: experimental part Neves, Marta Perro; Cravo, Sara; Lima, Raquel T.; Vasconcelos, M. Helena; Nascimento, M. São José; Silva, Artur M.S.; Pinto, Madalena; Cidade, Honorina; Corrêa, Arlene G. [Bioorganic and Medicinal Chemistry, 2012, vol. 20, # 1, p. 25 - 33]

75
[ 10139-84-1 ]
[ 98-88-4 ]
[ 100410-78-4 ]

Yield	Reaction Conditions	Operation in experiment
75%	With potassium carbonate In acetone for 8h; Reflux;
71%	With potassium carbonate In acetone for 12h; Reflux;

Reference： [1]Li, Ren-Shi; Wang, Xiao-Bing; Hu, Xiao-Jun; Kong, Ling-Yi [Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 9, p. 2636 - 2641]
[2]Zhao, Gang; Lan, Dengzhe; Qi, Guobao [Chemical Biology and Drug Design, 2017, vol. 90, # 5, p. 778 - 790]

76
[ 64-18-6 ]
[ 13214-66-9 ]
[ 10139-84-1 ]
2-methyl-4-(1-((4-phenylbutyl)amino)ethyl)benzene-1,3-diol formic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	Stage #1: 4-phenyl-1-butylamine; 1-(2,4-dihydroxy-3-methylphenyl)ethanone With sodium triacetoxyborohydride; acetic acid In 1,2-dichloro-ethane at 20℃; Stage #2: formic acid In water; acetonitrile for 0.333333h;

Reference： [1]Reutlinger, Michael; Rodrigues, Tiago; Schneider, Petra; Schneider, Gisbert [Angewandte Chemie - International Edition, 2014, vol. 53, # 16, p. 4244 - 4248][Angew. Chem., 2014, vol. 53-126, # 16, p. 4330 - 4334]

77
[ 104-01-8 ]
[ 10139-84-1 ]
7-hydroxy-3-(4-methoxyphenyl)-4,8-dimethyl-2Hchromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With potassium acetate; acetic anhydride at 135 - 140℃;	7-Hydroxy-3-(4-methoxyphenyl)-4,8-dimethyl-2Hchromen-2-one (1f) A mixture of 2,4-dihydroxy-3-methylacetophenone9 (1.66 g, 10 mmol), 4-methoxyphenylaceticacid (1.66 g, 10 mmol), and KOAc (2.94 g, 30 mmol) inAc2O (20 ml) was stirred and heated at 135-140° for 15-30 h, then poured into cold water (100 ml) and theprecipitate that formed was filtered off. The precipitate wasdissolved in ethanol (20 mmol), treated with H2SO4 (1 ml),and refluxed for 6-8 h. The reaction mixture was pouredinto water (100 ml), the precipitate that formed was filteredoff, dried, and crystallized from a 1:1 DMF-mixture. Yield 2.16 g (73%), light-yellow crystals, mp 280-282°C. IR spectrum, ν, cm-1: 2967, 2930, 1676, 1606,1563, 1348, 1276, 1250, 1097, 1025. 1H NMR spectrum(500 MHz, DMSO-d6), δ, ppm (J, Hz): 2.18 (3H, s) and2.19 (3H, s, 4,8-3); 3.79 (3H, s, 3); 6.88 (1, d,3J = 8.7, H-6); 6.98 (2, d, 3J = 8.6, H-3',5'); 7.20 (2, d,3J = 8.6, H-2',6'); 7.47 (1, d, 3J = 8.7, H-5); 10.34 (1H, s,). 13C NMR spectrum (126 MHz, DMSO-d6), δ, ppm:8.0 (3); 16.4 (3); 55.1 (3); 110.3; 111.8; 112.4;113.4; 121.6; 123.6; 127.0; 131.6; 148.2; 151.7; 158.4;158.6; 160.6. Mass spectrum, m/z (Irel, %): 297 [M+H]+(100). Found, %: C 72.84; H 5.31. C18H16O4. Calculated,%: C 72.96; H 5.44.

Reference： [1]Mrug, Galyna P.; Kondratyuk, Kostyantyn M.; Bondarenko, Svitlana P.; Frasinyuk, Mykhaylo S. [Chemistry of Heterocyclic Compounds, 2016, vol. 52, # 7, p. 460 - 466][Khim. Geterotsikl. Soedin., 2016, vol. 52, # 7, p. 460 - 466,7]

78
[ 10139-84-1 ]
[ 105-58-8 ]
ethyl 3-(2,4-dihydroxy-3-methylphenyl)-3-oxopropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 1-(2,4-dihydroxy-3-methylphenyl)ethanone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 3.3h; Inert atmosphere; Cooling with ice; Stage #2: Diethyl carbonate In tetrahydrofuran at 20℃; Inert atmosphere; Cooling with ice;	4.2. General procedures for syntheses of ethyl 3-(2-hydroxyphenyl)-3-oxopropanoates (1a-1s) General procedure: Under a dry argon atmosphere, lithium bis(trimethylsilyl)amide (1 M, 3 mmol) was cooled 78 C and a mixture of 2-hydroxyacetophenone (136 mg, 1 mmol) in dry THF (2 mL) was added dropwise to the above solution in 20 min. The reaction solution was stirred at 78 C for 1 h and in ice-bath for 2 h, and then a solution of diethyl carbonate (127.4 mg, 1.08 mmol) in dry THF(1 mL) was rapidly added to the above mixture in ice-bath for 3-4 h. Then, the mixture was stirred at room temperature. After 2-hydroxyacetophenone had disappeared completely, the reaction solution poured into a mixture of concentrated HCl (1.5 mL) and ice (20 g). The mixture was extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude products were purified using column chromatography on silica gel to give 1a in good yields, and 1b-1s were prepared with the same method.

Reference： [1]Zhang, Jin; Xue, Wenhao; Wang, Pei; Wang, Tao; Liang, Yong; Zhang, Zunting [Tetrahedron, 2018, vol. 74, # 36, p. 4712 - 4720]

79
[ 10139-84-1 ]
1-(2,4-dihydroxy-3-(hydroxymethyl)phenyl)ethan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With α-ketoglutaric acid; claD; oxygen; iron(II) sulfate; sodium L-ascorbate In aq. buffer at 30℃; for 3h; Enzymatic reaction;

Reference： [1]Doyon, Tyler J.; Perkins, Jonathan C.; Baker Dockrey, Summer A.; Romero, Evan O.; Skinner, Kevin C.; Zimmerman, Paul M.; Narayan, Alison R. H. [Journal of the American Chemical Society, 2019, vol. 141, # 51, p. 20269 - 20277]

80
[ 10139-84-1 ]
[ 122-51-0 ]
7-hydroxy-8-methyl-4H-chromen-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With perchloric acid at 20℃; for 1.5h;

Reference： [1]Zhao, Lanying; Li, Yueshan; Wang, Yujiao; Qiao, Zeen; Miao, Zhuang; Yang, Jiao; Huang, Luyi; Tian, Chenyu; Li, Linli; Chen, Danian; Yang, Shengyong [Journal of Medicinal Chemistry, 2019, vol. 62, # 23, p. 10691 - 10710]

81
[ 10139-84-1 ]
[ 29111-46-4 ]
C₁₇H₁₉N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-1 k-2 (80 mg, 0.48 mmol), H-1 (95.4 mg, 0.578 mmol) were dissolved in DMSO (1.0 mL), and the mixture was stirred at 100° C. for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the precipitated solid was collected by filtration and washed with methylene chloride to give k-2:H-1 (80.4 mg, 0.257 mmol, yield 53%) as a yellow solid.
53%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-1 k-2 (80 mg, 0.48 mmol), H-1 (95.4 mg, 0.578 mmol) were dissolved in DMSO (1.0 mL), and the mixture wasstirred at 100°C for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the precipitated solidwas collected by filtration and washed with methylene chloride to give k-2:H-1 (80.4 mg, 0.257 mmol, yield 53%) as ayellow solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0100
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0123

82
[ 10139-84-1 ]
2-(o-tolylamino)acetohydrazide [ No CAS ]
C₁₈H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
21%	In dimethyl sulfoxide at 100℃; for 19h;	1 Synthesis of k-2:H-2 k-2 (80 mg, 0.48 mmol), H-2 (112 mg, 0.625 mmol) were dissolved in DMSO (1 mL), and the mixture was stirred at 100° C. for 19 hr. The mixture was allowed to cool, distilled water (30 mL), ethyl acetate (30 mL) were added and the mixture was partitioned. The organic layer was washed with saturated brine (30 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by moderate-pressure silica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=10/90-80/20) to give k-2:H-2 (34 mg, 0.10 mmol, yield 21%) as a light yellow solid.
21%	In dimethyl sulfoxide at 100℃; for 19h;	1 Synthesis of k-2:H-2 k-2 (80 mg, 0.48 mmol), H-2 (112 mg, 0.625 mmol) were dissolved in DMSO (1 mL), and the mixture was stirredat 100°C for 19 hr. The mixture was allowed to cool, distilled water (30 mL), ethyl acetate (30 mL) were added and themixture was partitioned. The organic layer was washed with saturated brine (30 mL), dried over anhydrous sodiumsulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by moderate-pressuresilica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=10/90 - 80/20) to give k-2:H-2 (34 mg, 0.10mmol, yield 21%) as a light yellow solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0101
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0124

83
[ 10139-84-1 ]
[ 2371-35-9 ]
C₁₈H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-3 k-2 (80 mg, 0.48 mmol), H-3 (104 mg, 0.578 mmol) were dissolved in DMSO (1 mL), and the mixture was stirred at 100° C. for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the mixture was decantated. The obtained residue was dissolved in methylene chloride (3 mL), hexane (3 mL) was added and the precipitated solid was collected by filtration. The obtained solid was purified by moderate-pressure silica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=50/50-80/20) to give k-2:H-3 (46.9 mg, 0.143 mmol, yield 30%) as a light yellow solid.
30%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-3 k-2 (80 mg, 0.48 mmol), H-3 (104 mg, 0.578 mmol) were dissolved in DMSO (1 mL), and the mixture was stirredat 100°C for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the mixture was decantated.The obtained residue was dissolved in methylene chloride (3 mL), hexane (3 mL) was added and the precipitated solidwas collected by filtration. The obtained solid was purified by moderate-pressure silica gel column chromatography(silica gel 10 g, ethyl acetate/hexane=50/50 - 80/20) to give k-2:H-3 (46.9 mg, 0.143 mmol, yield 30%) as a light yellow solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0102
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0125

84
[ 10139-84-1 ]
[ 2350-99-4 ]
C₁₈H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	In dimethyl sulfoxide at 100℃; for 19h;	1 Synthesis of k-2:H-4 k-2 (80 mg, 0.48 mmol), H-4 (112 mg, 0.625 mmol) were dissolved in DMSO (1 mL), and the mixture was stirred at 100° C. for 19 hr. The mixture was allowed to cool, distilled water (10 mL) was added, the mixture was decantated, and the residue was washed with methylene chloride to give k-2:H-4 (58.7 mg, 0.179 mmol, yield 37%) as a light yellow solid.
37%	In dimethyl sulfoxide at 100℃; for 19h;	1 Synthesis of k-2:H-4 k-2 (80 mg, 0.48 mmol), H-4 (112 mg, 0.625 mmol) were dissolved in DMSO (1 mL), and the mixture was stirredat 100°C for 19 hr. The mixture was allowed to cool, distilled water (10 mL) was added, the mixture was decantated,and the residue was washed with methylene chloride to give k-2:H-4 (58.7 mg, 0.179 mmol, yield 37%) as a light yellowsolid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0103
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0126

85
[ 10139-84-1 ]
[ 710-31-6 ]
C₁₇H₁₈FN₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
23%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-5 k-2 (80 mg, 0.48 mmol), H-5 (106 mg, 0.578 mmol) were dissolved in DMSO (1 mL), and the mixture was stirred at 100° C. for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the mixture was decantated. The obtained residue was dissolved in methylene chloride (3 mL), hexane (1 mL) was added and the precipitated solid was collected by filtration. The obtained solid was purified by moderate-pressure silica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=50/50-80/20) to give k-2:H-5 (36.6 mg, 0.110 mmol, yield 23%) as a white solid.
23%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-5 k-2 (80 mg, 0.48 mmol), H-5 (106 mg, 0.578 mmol) were dissolved in DMSO (1 mL), and the mixture was stirredat 100°C for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the mixture was decantated.The obtained residue was dissolved in methylene chloride (3 mL), hexane (1 mL) was added and the precipitated solidwas collected by filtration. The obtained solid was purified by moderate-pressure silica gel column chromatography(silica gel 10 g, ethyl acetate/hexane=50/50 - 80/20) to give k-2:H-5 (36.6 mg, 0.110 mmol, yield 23%) as a white solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0104
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0127

86
[ 10139-84-1 ]
2-(naphthalen-1-ylamino)acetohydrazide [ No CAS ]
C₂₁H₂₁N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-6 k-2 (100 mg, 0.602 mmol), H-6 (155 mg, 0.722 mmol) were dissolved in DMSO (1 mL), and the mixture was stirred at 100° C. for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the mixture was decantated. The obtained residue was washed with methylene chloride to give k-2:H-6 (59.3 mg, 0.163 mmol, yield 27%) as a light brown solid.
27%	In dimethyl sulfoxide at 100℃; for 15h;	1 Synthesis of k-2:H-6 k-2 (100 mg, 0.602 mmol), H-6 (155 mg, 0.722 mmol) were dissolved in DMSO (1 mL), and the mixture wasstirred at 100°C for 15 hr. The mixture was allowed to cool, distilled water (10 mL) was added and the mixture wasdecantated. The obtained residue was washed with methylene chloride to give k-2:H-6 (59.3 mg, 0.163 mmol, yield27%) as a light brown solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0105
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0128

87
[ 10139-84-1 ]
2-(phenylamino)butanehydrazide [ No CAS ]
C₁₉H₂₃N₃O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	In dimethyl sulfoxide at 100℃; for 17h;	1 Synthesis of k-2:H-7 k-2 (80 mg, 0.48 mmol), H-7 (121 mg, 0.626 mmol) were dissolved in DMSO (0.55 mL), and the mixture was stirred at 100° C. for 17 hr. The mixture was allowed to cool, distilled water (20 mL), ethyl acetate (20 mL) were added and the mixture was partitioned. The organic layer was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by moderate-pressure silica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=5/95-50/50) to give k-2:H-7 (109 mg, 0.319 mmol, yield 66%) as a light yellow solid.
66%	In dimethyl sulfoxide at 100℃; for 17h;	1 Synthesis of k-2:H-7 k-2 (80 mg, 0.48 mmol), H-7 (121 mg, 0.626 mmol) were dissolved in DMSO (0.55 mL), and the mixture wasstirred at 100°C for 17 hr. The mixture was allowed to cool, distilled water (20 mL), ethyl acetate (20 mL) were addedand the mixture was partitioned. The organic layer was washed with saturated brine (20 mL), dried over anhydroussodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by moderatepressuresilica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=5/95 - 50/50) to give k-2:H-7 (109 mg,0.319 mmol, yield 66%) as a light yellow solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0106
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0129

88
[ 10139-84-1 ]
[ 100133-39-9 ]
C₁₉H₂₃N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	In dimethyl sulfoxide at 100℃; for 18h;	1 Synthesis of k-2:H-9 k-2 (100 mg, 0.60 mmol), H-9 (164 mg, 0.784 mmol) were suspended in DMSO (1.2 mL) and the mixture was stirred at 100° C. for 18 hr. The mixture was allowed to cool, distilled water (12 mL), ethyl acetate (20 mL) were added and the mixture was partitioned. The organic layer was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by moderate-pressure silica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=10/90-60/40), and the obtained solid was washed with methylene chloride to give k-2:H-9 (63.1 mg, 0.177 mmol, yield 30%) as a light yellow solid.
30%	In dimethyl sulfoxide at 100℃; for 18h;	1 Synthesis of k-2:H-9 k-2 (100 mg, 0.60 mmol), H-9 (164 mg, 0.784 mmol) were suspended in DMSO (1.2 mL) and the mixture wasstirred at 100°C for 18 hr. The mixture was allowed to cool, distilled water (12 mL), ethyl acetate (20 mL) were addedand the mixture was partitioned. The organic layer was washed with saturated brine (20 mL), dried over anhydroussodium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by moderatepressuresilica gel column chromatography (silica gel 10 g, ethyl acetate/hexane=10/90 - 60/40), and the obtained solidwas washed with methylene chloride to give k-2:H-9 (63.1 mg, 0.177 mmol, yield 30%) as a light yellow solid.

Reference： [1]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - US2020/165194, 2020, A1 Location in patent: Paragraph 0107
[2]Current Patent Assignee: NISSAN CHEMICAL CORPORATION - EP3804707, 2021, A1 Location in patent: Paragraph 0104; 0130

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 -

CAS No. :	10139-84-1	MDL No. :	MFCD00010817
Formula :	C₉H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KMTLZBUHQPQFAV-UHFFFAOYSA-N
M.W :	166.17	Pubchem ID :	592139
Synonyms :

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

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. 10139-84-1 ] {[proInfo.proName]}

Quality Control of [ 10139-84-1 ]

Related Doc. of [ 10139-84-1 ]

Product Details of [ 10139-84-1 ]

Safety of [ 10139-84-1 ]

Application In Synthesis of [ 10139-84-1 ]

[ 10139-84-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of
[ 10139-84-1 ]

Aryls

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

[ CAS No. 10139-84-1 ] {[proInfo.proName]}

Quality Control of [ 10139-84-1 ]

Related Doc. of [ 10139-84-1 ]

Product Details of [ 10139-84-1 ]

Safety of [ 10139-84-1 ]

Application In Synthesis of [ 10139-84-1 ]

[ 10139-84-1 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 10139-84-1 ]

Aryls

Ketones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 10139-84-1 ]