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[ CAS No. 7476-66-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}

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

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3d Animation Molecule Structure of 7476-66-6

Chemical Structure| 7476-66-6

Chemical Structure| 7476-66-6

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Quality Control of [ 7476-66-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7476-66-6 ]

SDS Specification

Alternatived Products of [ 7476-66-6 ]

Product Details of [ 7476-66-6 ]

CAS No. :	7476-66-6	MDL No. :	MFCD00040996
Formula :	C₉H₉ClO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XOIOYHPJZJLTGK-UHFFFAOYSA-N
M.W :	184.62	Pubchem ID :	139032
Synonyms :

Calculated chemistry of [ 7476-66-6 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	47.1
TPSA :	26.3 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) :	-5.52 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.17
Log Po/w (XLOGP3) :	2.69
Log Po/w (WLOGP) :	1.82
Log Po/w (MLOGP) :	2.29
Log Po/w (SILICOS-IT) :	2.37
Consensus Log Po/w :	2.26

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.85
Solubility :	0.26 mg/ml ; 0.00141 mol/l
Class :	Soluble
Log S (Ali) :	-2.89
Solubility :	0.235 mg/ml ; 0.00127 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.14
Solubility :	0.134 mg/ml ; 0.000728 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 7476-66-6 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501	UN#:	3265
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 7476-66-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 7476-66-6 ]

[ 7476-66-6 ] Synthesis Path-Downstream 1~88

1
[ 67-56-1 ]
[ 4755-72-0 ]
[ 7476-66-6 ]

Reference： [1]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1898,vol. 30,p. 506
Chemisches Zentralblatt,1898,vol. 69,p. 917
[2]Justus Liebigs Annalen der Chemie,1883,vol. 220,p. 44

2
[ 4358-87-6 ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,2,3-Benzotriazole; thionyl chloride In dichloromethane at 20℃;
87%	With thionyl chloride In diethyl ether for 24h; Ambient temperature;
62%	With N,N-dimethyl-formamide; 2-Fluorobenzoyl chloride In 1,4-dioxane at 80℃; for 36h; Sealed tube;	General procedure: Entry 5: According to general procedure II (chapter 2.1.2) racemic methyl mandelate (rac-132, 336 mg, 2.00 mmol, 1.0 equiv), DMF (30.9 ilL, 29.2 mg, 0.40 mmol, 20 mol%), dioxane (1 mL, 2 M)and 2-fluoro benzoyl chloride (372 ilL, 490 mg, 3.00 mmol, 1.5 equiv) were combined and allowed to react for 36 h at 80 C. Chromatographic purification of the crude material (540 mg, 232/332 86:14) on silica gel (mass of crude material/Si02 1:9) with Et20/nPen 5:95 gave rise of the chloride rac-232 ascolorless oil (227 mg, 1.23 mmol, 62%).M (C9H9C102) = 184.62 g/mol; rf (Si02, Et20/nPen 5:95) = 0.37; [aID2° = +134.1 (c = 1.48 g/100 mL,CHCI3).

55%	With dmap; triethylamine; p-toluenesulfonyl chloride In dichloromethane at 0 - 15℃; for 12.5h;
	With thionyl chloride
	With pyridine; trichlorophosphate <i>dl</i>-phenylchloroacetic acid methyl ester;
4.9 g	With thionyl chloride for 0.5h; Heating;
	With phosphorus pentachloride In dichloromethane at 20℃; for 2h;
	In dichloromethane; water	1.a a) a) Synthesis of methyl chlorophenylacetate 1 For the synthesis of methyl chlorophenylacetate, 10.0 g (60 mmol) of methyl mandelate are dissolved in 10 ml of dichloromethane and, after addition of 4.79 ml (66 mmol, 1.1 equiv.) of thionyl chloride, warmed to 60° C. The mixture is stirred for 18 hours, the reaction solution is cooled to room temperature, a further 20 ml of dichloromethane are added, and the mixture is extracted twice each with 30 ml of water and saturated NaHCO3 solution. The organic phase is dried over sodium sulfate, and the reaction product is obtained after filtration and removal of the solvent by distillation.
	With thionyl chloride In dichloromethane at 60℃; for 18h;

Reference： [1]Chaudhari, Sachin S.; Akamanchi, Krishnacharya G. [Synlett, 1999, # 11, p. 1763 - 1765]
[2]Sehgal, R. K.; Griffin, G. W. [Liebigs Annalen der Chemie, 1991, # 6, p. 513 - 517]
[3]Current Patent Assignee: UNIVERSITY OF SAARLAND - WO2016/202894, 2016, A1 Location in patent: Page/Page column 51; 127; 131
[4]Location in patent: experimental part Ding, Rui; He, Yong; Wang, Xiao; Xu, Jingli; Chen, Yurong; Feng, Man; Qi, Chuanmin [Molecules, 2011, vol. 16, # 7, p. 5665 - 5673]
[5]Najer et al. [Bulletin de la Societe Chimique de France, 1958, p. 1189,1190]
[6]Wagner-Jauregg [Helvetica Chimica Acta, 1929, vol. 12, p. 63]
[7]Higgins, Stanley D.; Thomas, Barry C. [Journal of the Chemical Society. Perkin transactions I, 1982, p. 235 - 242]
[8]Fabre, Stephanie; Vila, Xavier; Zard, Samir Z. [Chemical Communications, 2006, # 47, p. 4964 - 4966]
[9]Current Patent Assignee: MERCK KGAA - US2007/219246, 2007, A1
[10]Current Patent Assignee: MERCK KGAA - WO2005/108355, 2005, A2 Location in patent: Page/Page column 75-76

3
[ 7476-66-6 ]
[ 104-88-1 ]
[ 132129-97-6 ]

Yield	Reaction Conditions	Operation in experiment
	With methanol; sodium methylate

Reference： [1]Dahn et al. [Helvetica Chimica Acta, 1957, vol. 40, p. 1521,1527]

4
[ 7476-66-6 ]
[ 123-11-5 ]
2,3-epoxy-3-(4-methoxy-phenyl)-2-phenyl-propionic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate

Reference： [1]Myers et al. [Journal of the American Chemical Society, 1955, vol. 77, p. 5655]

5
[ 7476-66-6 ]
[ 100-06-1 ]
[ 101595-39-5 ]

Yield	Reaction Conditions	Operation in experiment
	With copper; zinc; benzene Erwaermen des Reaktionsprodukts mit aethanol. Natronlauge;

Reference： [1]Nieuwland; Daly [Journal of the American Chemical Society, 1931, vol. 53, p. 1842,1843]

6
[ 7476-66-6 ]
[ 100-06-1 ]
3-hydroxy-3-(4-methoxy-phenyl)-2-phenyl-butyric acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper; zinc; benzene

Reference： [1]Nieuwland; Daly [Journal of the American Chemical Society, 1931, vol. 53, p. 1842,1843]

7
[ 67-56-1 ]
[ 2912-62-1 ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine at 20℃; for 3h;
75%	With pyridine
	With pyridine In benzene

In dichloromethane for 48h; Inert atmosphere;

Reference： [1]Haughton, Louise; Williams, Jonathan M. J. [Synthesis, 2001, # 6, p. 943 - 946]
[2]Yamazaki, Yoshimitsu; Yusa, Shiro; Kageyama, Yu-Ichi; Tsue, Hirohito; Hirao, Ken-Ichi; Okuno, Hiroaki [Journal of Fluorine Chemistry, 1996, vol. 79, # 2, p. 167 - 171]
[3]Martin,C.W. et al. [Journal of Organic Chemistry, 1978, vol. 43, p. 1071 - 1076]
[4]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]
[5]Afri, Michal; Gruzman, Arie; Korshin, Edward E.; Leitus, Gregory; Palczewski, Krzysztof; Rothstein, Ayelet; Trifonov, Lena; Viskind, Olga [European Journal of Organic Chemistry, 2021, vol. 2021, # 48, p. 6725 - 6736]

8
[ 7476-66-6 ]
[ 139-02-6 ]
[ 32191-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	With phenol In 1,4-dioxane

Reference： [1]Cast,J. et al. [Journal of the Chemical Society, 1960, p. 3521 - 3527]
[2]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

9
[ 7476-66-6 ]
[ 613-94-5 ]
[ 142068-26-6 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine In methanol

Reference： [1]Hall,J.H.; Wojciechowska,M. [Journal of Organic Chemistry, 1978, vol. 43, # 25, p. 4869 - 4873]

10
[ 7476-66-6 ]
[ 108-98-5 ]
[ 51256-38-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium methylate In methanol

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]

11
[ 7476-66-6 ]
[ 292638-85-8 ]
trans-1,2-Dimethoxycarbonyl-1-phenylcyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In benzene

Reference： [1]McCoy,L.L. [Journal of the American Chemical Society, 1962, vol. 84, p. 2246 - 2249]

12
[ 7476-66-6 ]
[ 80-62-6 ]
[ 71096-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N,N,N,N,N-hexamethylphosphoric triamide

Reference： [1]McCoy,L.L. [Journal of the American Chemical Society, 1962, vol. 84, p. 2246 - 2249]

13
[ 7476-66-6 ]
[ 80-62-6 ]
cis (±)-1-methyl-2-phenylcyclopropane-1,2-dicarboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In toluene

Reference： [1]McCoy,L.L. [Journal of Organic Chemistry, 1960, vol. 25, p. 2078 - 2082]

14
[ 67-56-1 ]
[ 10295-39-3 ]
[ 7476-66-6 ]
[ 142-04-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 76% 2: 56%

Reference： [1]Meilahn, Marcus K.; Pottorf, Richard S. [Journal of Organic Chemistry, 1980, vol. 45, p. 2004 - 2005]

15
[ 52708-32-4 ]
[ 7476-66-6 ]
[4-(3,5-Dimethyl-pyrazol-1-yl)-phenylamino]-phenyl-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 25h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

16
[ 60418-47-5 ]
[ 7476-66-6 ]
[2-(3,5-Dimethyl-pyrazol-1-yl)-phenylamino]-phenyl-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 40h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

17
[ 7476-66-6 ]
[ 76458-19-0 ]
Phenyl-[4-(3,4,5-trimethyl-pyrazol-1-yl)-phenylamino]-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 25h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

18
[ 7476-66-6 ]
[ 86998-86-9 ]
[ 86998-91-6 ]

Yield	Reaction Conditions	Operation in experiment
80%	With pyridine for 2h; steam-bath;

Reference： [1]Talukdar, P. B.; Sengupta, S. K.; Datta, A. K. [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1983, vol. 22, # 3, p. 243 - 248]

19
[ 62054-83-5 ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With chlorine; trimethyl orthoformate In methanol at 0℃; for 0.166667h;

Reference： [1]Higgins, Stanley D.; Thomas, C. Barry [Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1483 - 1488]

20
[ 62054-83-5 ]
[ 7476-66-6 ]
[ 532-27-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 74% 2: 22%	With chlorine In chloroform ice-cooling;

Reference： [1]Higgins, Stanley D.; Thomas, C. Barry [Journal of the Chemical Society. Perkin transactions I, 1983, # 7, p. 1483 - 1488]

21
[ 59950-99-1 ]
[ 7476-66-6 ]
[ 81265-15-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 18% 2: 42%	With trichloroisocyanuric acid; isocyanuric acid In N,N-dimethyl-formamide at 40℃; for 18h;
1: 42% 2: 18%	With trichloroisocyanuric acid In N,N-dimethyl-formamide at 40℃; for 18h;

Reference： [1]Boni, Monica; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 1, p. 156 - 159]
[2]Boni, Monica; Ghelfi, Franco; Pagnoni, Ugo Maria; Pinetti, Adriano [Bulletin of the Chemical Society of Japan, 1994, vol. 67, # 1, p. 156 - 159]

22
[ 7476-66-6 ]
[ 17635-45-9 ]
Phenyl-(4-pyrazol-1-yl-phenylamino)-acetic acid methyl ester [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,1980,vol. 17,p. 1049 - 1051

23
[ 7476-66-6 ]
[ 292638-85-8 ]
cis-1,2-Dimethoxycarbonyl-1-phenylcyclopropane [ No CAS ]
trans-1,2-Dimethoxycarbonyl-1-phenylcyclopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylmethyl potassium In tetrahydrofuran; dimethyl sulfoxide comparative study of reaction with polymer bounded reagents; various cations (Li, Na, K) and solvents (THF, toluene, DMSO, DMF);
	With trityllithium In tetrahydrofuran at 20℃;
	With sodium hydride In benzene at 20℃; Title compound not separated from byproducts;

	With triphenylmethyl potassium In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide at -60℃;
	With sodium hydride In N,N-dimethyl-formamide at 20℃; Title compound not separated from byproducts;

Reference： [1]Artaud, I.; Viout, I. [Tetrahedron Letters, 1981, vol. 22, p. 1009 - 1012]
[2]Artaud, I.; Viout, I. [Tetrahedron Letters, 1981, vol. 22, p. 1009 - 1012]
[3]Nishiyama, Kazuyoshi; Inouye, Yuzo [Agricultural and Biological Chemistry, 1982, vol. 46, # 4, p. 1027 - 1034]
[4]Artaud, I.; Viout, I. [Tetrahedron Letters, 1981, vol. 22, p. 1009 - 1012]
[5]Nishiyama, Kazuyoshi; Inouye, Yuzo [Agricultural and Biological Chemistry, 1982, vol. 46, # 4, p. 1027 - 1034]

24
[ 7476-66-6 ]
[ 586-96-9 ]
[ 83020-38-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	With potassium hydroxide In ethanol; water at 30℃;

Reference： [1]Sehgal, R. K.; Griffin, G. W. [Liebigs Annalen der Chemie, 1991, # 6, p. 513 - 517]

25
[ 7476-66-6 ]
[ 54705-91-8 ]
Phenyl-(2-pyrazol-1-yl-phenylamino)-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate In ethanol at 130℃; for 40h; Yield given;

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

26
[ 7476-66-6 ]
[ 100-52-7 ]
(2R,3R)-und (2S,3S)-3-Hydroxy-2,3-diphenylpropansaeure-methylester [ No CAS ]
α-<Hydroxy(phenyl)methyl>benzenessigsaeure-methylester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With chromium dichloride; lithium iodide In tetrahydrofuran at 55℃; for 2h; Yield given. Yields of byproduct given;

Reference： [1]Wessjohann, Ludger; Gabriel, Tobias [Journal of Organic Chemistry, 1997, vol. 62, # 11, p. 3772 - 3774]

27
[ 7476-66-6 ]
[ 95-48-7 ]
[ 194418-47-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1.) THF, 2.) DMSO; Yield given. Multistep reaction;

Reference： [1]Kirmse, Wolfgang; Konrad, Wolfgang; Oezkir, Ismail S. [Tetrahedron, 1997, vol. 53, # 29, p. 9935 - 9964]

28
[ 40195-27-5 ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
62%	With tris(triphenylphosphine)ruthenium(II) chloride; trifluoromethane sulfonyl chloride In benzene at 120℃; for 7h;

Reference： [1]Kamigata, Nobumasa; Udodaira, Kumiko; Shimizu, Toshio [Phosphorus, Sulfur and Silicon and the Related Elements, 1997, vol. 129, p. 155 - 168]

Yield	Reaction Conditions	Operation in experiment
	With chloroform; phosphorus pentachloride methyl ester of/the/ dextrorotatory phenylchloroacetic acid;
	With phosphorus pentachloride; toluene methyl ester of/the/ dextrorotatory phenylchloroacetic acid;

Yield	Reaction Conditions	Operation in experiment
	With pyridine; trichlorophosphate <d(-)-phenylchloroacetic acid >-methyl ester;

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride levorotatory substance;

32
[ 7476-66-6 ]
[ 140-89-6 ]
[ 921594-06-1 ]

Yield	Reaction Conditions	Operation in experiment
3.10 g	In ethanol at 20℃; for 4h;

Reference： [1]Fabre, Stephanie; Vila, Xavier; Zard, Samir Z. [Chemical Communications, 2006, # 47, p. 4964 - 4966]

33
[ 67-56-1 ]
ethyl 2-chloro-2-phenylacetate [ No CAS ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	at 64℃; for 12h;

Reference： [1]Remme, Nicole; Koschek, Katharina; Schneider, Christoph [Synlett, 2007, # 3, p. 491 - 493]

34
[ 7476-66-6 ]
[ 92548-75-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1.) NaH / 1.) THF, 2.) DMSO 2: 85 percent / LiAlH₄ / diethyl ether 3: 74 percent / pyridine 4: 70 percent / KOH / various solvent(s) / 100 - 200 °C

Reference： [1]Kirmse, Wolfgang; Konrad, Wolfgang; Oezkir, Ismail S. [Tetrahedron, 1997, vol. 53, # 29, p. 9935 - 9964]

35
[ 7476-66-6 ]
[ 194418-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) NaH / 1.) THF, 2.) DMSO 2: 85 percent / LiAlH₄ / diethyl ether

Reference： [1]Kirmse, Wolfgang; Konrad, Wolfgang; Oezkir, Ismail S. [Tetrahedron, 1997, vol. 53, # 29, p. 9935 - 9964]

36
[ 7476-66-6 ]
[ 194418-49-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) NaH / 1.) THF, 2.) DMSO 2: 85 percent / LiAlH₄ / diethyl ether 3: 74 percent / pyridine

Reference： [1]Kirmse, Wolfgang; Konrad, Wolfgang; Oezkir, Ismail S. [Tetrahedron, 1997, vol. 53, # 29, p. 9935 - 9964]

37
[ 7476-66-6 ]
Phenyl-(2-pyrazol-1-yl-phenylamino)-acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. sodium acetate / ethanol / 40 h / 130 °C 2: 10 percent aq. NaOH

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

38
[ 7476-66-6 ]
[ 78786-63-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: aq. sodium acetate / ethanol / 40 h / 130 °C 2: 10 percent aq. NaOH

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

39
[ 7476-66-6 ]
[ 78786-62-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aq. sodium acetate / ethanol / 40 h / 130 °C 2: 10 percent aq. NaOH 3: NaNO₂, 25 percent aq. HCl

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

40
[ 7476-66-6 ]
C₁₇H₁₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aq. sodium acetate / ethanol / 40 h / 130 °C 2: 10 percent aq. NaOH 3: NaNO₂, 25 percent aq. HCl 4: 63 percent / acetic anhydride / 3 h

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

41
[ 7476-66-6 ]
[ 78786-64-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: aq. sodium acetate / ethanol / 40 h / 130 °C 2: 10 percent aq. NaOH 3: NaNO₂, 25 percent aq. HCl / 3 h

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

42
[ 7476-66-6 ]
C₁₉H₁₆N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: aq. sodium acetate / ethanol / 40 h / 130 °C 2: 10 percent aq. NaOH 3: NaNO₂, 25 percent aq. HCl / 3 h 4: 60 percent / acetic anhydride / 3 h

Reference： [1]Havanur; Badami; Puranik [Archiv der Pharmazie, 1981, vol. 314, # 6, p. 503 - 511]

43
MANDELIC ACID [ No CAS ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 5.3 g / dry HCl / 18 h / Heating 2: 4.9 g / thionyl chloride / 0.5 h / Heating

Reference： [1]Higgins, Stanley D.; Thomas, Barry C. [Journal of the Chemical Society. Perkin transactions I, 1982, p. 235 - 242]

44
[ 7476-66-6 ]
[ 15206-55-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 59 percent / KOH / ethanol; H₂O / 30 °C 2: 7 percent / 7 h / Ambient temperature; Irradiation

Reference： [1]Sehgal, R. K.; Griffin, G. W. [Liebigs Annalen der Chemie, 1991, # 6, p. 513 - 517]

45
[ 7476-66-6 ]
[ 83020-39-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 59 percent / KOH / ethanol; H₂O / 30 °C 2: 16 percent / 7 h / Ambient temperature; Irradiation

Reference： [1]Sehgal, R. K.; Griffin, G. W. [Liebigs Annalen der Chemie, 1991, # 6, p. 513 - 517]

46
[ 7476-66-6 ]
[ 76457-95-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

47
[ 7476-66-6 ]
[ 76457-98-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

48
[ 7476-66-6 ]
[ 76458-00-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

49
[ 7476-66-6 ]
[ 76458-03-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH 3: Sodium nitrite, 25percent hydrochloric acid / 3 h / 0 - 5 °C

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

50
[ 7476-66-6 ]
[ 76458-12-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH 3: Sodium nitrite, 25percent hydrochloric acid / 3 h / 0 - 5 °C 4: 60 percent / 3 h / 100 °C

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

51
[ 7476-66-6 ]
[ 76458-06-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH 3: Sodium nitrite, 25percent hydrochloric acid / 3 h / 0 - 5 °C

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

52
[ 7476-66-6 ]
[ 76458-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH 3: Sodium nitrite, 25percent hydrochloric acid / 3 h / 0 - 5 °C

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

53
[ 7476-66-6 ]
[ 76458-15-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH 3: Sodium nitrite, 25percent hydrochloric acid / 3 h / 0 - 5 °C 4: 63 percent / 3 h / 100 °C

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

54
[ 7476-66-6 ]
[ 76458-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: Sodium acetate / ethanol / 25 h / 130 °C 2: 10percent aq. NaOH 3: Sodium nitrite, 25percent hydrochloric acid / 3 h / 0 - 5 °C 4: 70 percent / 3 h / 100 °C

Reference： [1]Havanur; Badami; Puranik [Journal of Heterocyclic Chemistry, 1980, vol. 17, # 5, p. 1049 - 1051]

55
[ 7476-66-6 ]
[ 107416-49-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene 2: hydrochloric acid , aqueous

Reference： [1]Najer et al. [Bulletin de la Societe Chimique de France, 1958, p. 1189,1190]

56
[ 7476-66-6 ]
[ 100390-49-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene 2: hydrochloric acid , aqueous

Reference： [1]Najer et al. [Bulletin de la Societe Chimique de France, 1958, p. 1189,1190]

57
[ 7476-66-6 ]
[ 108897-44-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene 2: aqueous hydrochloric acid

Reference： [1]Najer et al. [Bulletin de la Societe Chimique de France, 1958, p. 1189,1190]

58
[ 7476-66-6 ]
[ 109513-05-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium methylate; methanol 2: methanol. KOH-solution

Reference： [1]Dahn et al. [Helvetica Chimica Acta, 1957, vol. 40, p. 1521,1527]

59
[ 7476-66-6 ]
[ 53876-79-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: ethanol 2: LiAlH₄ 3: H₂O₂ / 4>6Mo₇O₂₄ 4: SOCl₂ 5: Et₃N / benzene 6: Et₃N / benzene 7: H₂O₂ / 4>6Mo₇O₂₄

Reference： [1]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

60
[ 7476-66-6 ]
2-phenyl-2-(phenylthio)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaOMe / methanol 2: LiAlH₄
	Multi-step reaction with 2 steps 1: ethanol 2: LiAlH₄

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]
[2]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

61
[ 7476-66-6 ]
[ 33169-42-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaOMe / methanol 2: LiAlH₄ 3: (oxidation)
	Multi-step reaction with 3 steps 1: ethanol 2: LiAlH₄ 3: H₂O₂ / 4>6Mo₇O₂₄

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]
[2]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

62
[ 7476-66-6 ]
[ 65885-22-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaOMe / methanol 2: LiAlH₄ 3: (oxidation) 4: SOCl₂
	Multi-step reaction with 4 steps 1: ethanol 2: LiAlH₄ 3: H₂O₂ / 4>6Mo₇O₂₄ 4: SOCl₂

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]
[2]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

63
[ 7476-66-6 ]
[ 65885-23-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaOMe / methanol 2: LiAlH₄ 3: (oxidation) 4: PBr₃

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]

64
[ 7476-66-6 ]
[ 65885-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaOMe / methanol 2: LiAlH₄ 3: (oxidation)

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]

65
[ 7476-66-6 ]
[ 49833-39-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: ethanol 2: LiAlH₄ 3: H₂O₂ / 4>6Mo₇O₂₄ 4: SOCl₂ 5: Et₃N / benzene

Reference： [1]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

66
[ 7476-66-6 ]
[ 65885-24-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: NaOMe / methanol 2: LiAlH₄ 3: (oxidation)

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]

67
[ 7476-66-6 ]
[ 29290-75-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: ethanol 2: LiAlH₄ 3: H₂O₂ / 4>6Mo₇O₂₄ 4: SOCl₂ 5: Et₃N / benzene 6: Et₃N / benzene

Reference： [1]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

68
[ 7476-66-6 ]
[ 65885-17-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1: ethanol 2: LiAlH₄ 3: H₂O₂ / 4>6Mo₇O₂₄ 4: SOCl₂ 5: Et₃N / benzene 6: Et₃N / benzene 7: ethanol

Reference： [1]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

69
[ 7476-66-6 ]
[ 53574-80-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: PhOH / dioxane 2: LiAlH₄ / diethyl ether

Reference： [1]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

70
[ 7476-66-6 ]
[ 69333-60-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: PhOH / dioxane 2: LiAlH₄ / diethyl ether 3: Py

Reference： [1]Redman,R.P. et al. [Journal of the Chemical Society. Perkin transactions II, 1978, p. 1135 - 1144]

71
MANDELIC ACID [ No CAS ]
[ 7476-66-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: PCl₅

Reference： [1]Marshall,D.R. et al. [Journal of the Chemical Society. Perkin transactions II, 1977, p. 1914 - 1919]

72
[ 7476-66-6 ]
[ 67859-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Py / methanol 2: aq. Na₂CO₃ / ethanol; CHCl₃

Reference： [1]Hall,J.H.; Wojciechowska,M. [Journal of Organic Chemistry, 1978, vol. 43, # 25, p. 4869 - 4873]

73
[ 7476-66-6 ]
[ 20245-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: methanol / Heating 2: LiAlH₄ / diethyl ether

Reference： [1]Duhamel,L. et al. [Bulletin de la Societe Chimique de France, 1973, p. 2460 - 2466]

74
[ 7476-66-6 ]
[ 106-45-6 ]
[ 32121-42-9 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In dichloromethane for 2h; Heating / reflux;

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2005/108355, 2005, A2 Location in patent: Page/Page column 76

75
[ 109904-37-2 ]
[ 7476-66-6 ]
[ 109904-28-1 ]

Yield	Reaction Conditions	Operation in experiment
86%		5 Methyl alpha (2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl-acetate EXAMPLE 5 Methyl alpha (2-oxo 2,4,5,6,7,7a-hexahydro thieno [3,2-c] 5-pyridyl) phenyl-acetate (in formula I: Y=--OCH3; X=H) (Derivative no. 2) This compound is prepared by the operational method described in Example 4 by alkylation of 5,6,7,7a-tetrahydro 4H-thieno [3,2-c] 2-pyridone (II) with methyl alphachlorophenylacetate (in formula IIIb: R=--CH3; X=H; hal=Cl). The product in hydrobromide form is white crystals, M.P.=205° C. (dec.), yield 86%; IR (KBr): vc =o (ester): 1745 cm-1; vc =o (thiolactone): 1695 cm-1; NMR 1 H in ppm (DMSO-d6): 7.60 (m,5H); 6.57 (s,1H); 5.83 (s,1H); 3.77 (s,3H).

Reference： [1]Current Patent Assignee: SANOFI - US4740510, 1988, A

76
[ 7476-66-6 ]
[ 78767-83-6 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide In acetone	15.a (a) (a) Methyl α-iodophenylacetate Sodium iodide (7.5 g, 0.05 mol) dissolved in analar acetone (25 ml) was stirred at room temperature and to it added methyl α-chlorophenylacetate (9.32 g, 0.05 mol). Stirred for 15 minutes. The precipitate sodium chloride was allowed to settle.

Reference： [1]Current Patent Assignee: GLAXOSMITHKLINE PLC - US4539202, 1985, A

77
[ 7476-66-6 ]
[ 106-45-6 ]
methyl phenyl-p-tolylsulfanylacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In dichloromethane; water	1.b b) b) Synthesis of methyl phenyl-p-tolylsulfanylacetate 2 For the synthesis of methyl phenyl-p-tolylsulfanylacetate, 2.0 g (7.9 mmol) of 1 are dissolved in 10 ml of dichloromethane, 1 equiv. of each of 4-methylthiophenol (7.9 mmol, 0.98 g) and sodium hydroxide (7.9 mmol, 0.32 g) are added, and the mixture is refluxed for 2 hours. The reaction mixture is cooled to room temperature and filtered, and the solvent is distilled off. Water is added to the residue, and the reaction product is extracted with ethyl acetate.

Reference： [1]Current Patent Assignee: MERCK KGAA - US2007/219246, 2007, A1

78
[ 7476-66-6 ]
C₉H₁₂Cl₂MgO₂ [ No CAS ]
[ 1197333-34-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2-chloro-2-phenylethanoate With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; Inert atmosphere; Stage #2: C₉H₁₂Cl₂MgO₂ In tetrahydrofuran at -78 - 0℃; Inert atmosphere; Stage #3: With water; ammonium chloride In tetrahydrofuran

Reference： [1]Location in patent: experimental part Satoh, Tsuyoshi; Kaneta, Hiroaki; Matsushima, Ayako; Yajima, Masanobu [Tetrahedron Letters, 2009, vol. 50, # 46, p. 6280 - 6285]

79
[ 2570-00-5 ]
[ 21210-43-5 ]
[ 7476-66-6 ]
[ 886-38-4 ]

Yield	Reaction Conditions	Operation in experiment
93%	In dichloromethane at 23℃; for 1.08333h; Inert atmosphere;

Reference： [1]Kelly, Brendan D.; Lambert, Tristan H. [Journal of the American Chemical Society, 2009, vol. 131, # 39, p. 13930 - 13931]

80
[ 23535-28-6 ]
[ 7476-66-6 ]
[ 1380490-86-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: bromocyane / dichloromethane / 12 h / 20 °C / Inert atmosphere 2: water; toluene / 6 h / 0 - 20 °C 3: dichloromethane / 12 h / Inert atmosphere; Reflux

Reference： [1]Tayama, Eiji; Sato, Ryota; Takedachi, Keisuke; Iwamoto, Hajime; Hasegawa, Eietsu [Tetrahedron, 2012, vol. 68, # 24, p. 4710 - 4718]

81
methyl α-(N,N-dimethylamino)phenylacetate [ No CAS ]
[ 541-41-3 ]
[ 7476-66-6 ]
[ 1380490-86-7 ]

Yield	Reaction Conditions	Operation in experiment
1: 51% 2: 41 %Spectr.	In dichloromethane for 12h; Inert atmosphere; Reflux;	3.2. Representative procedure for the amine de-alkylation of 1d with ethyl chloroformate General procedure: A solution of 1d (133 mg, 0.607 mmol) in dichloromethane (3.0 mL) was treated with ethyl chloroformate (95%, 73 μL, 0.73 mmol) and refluxed for 12 h under an argon atmosphere. The resulting mixture was cooled at room temperature, and the volatiles were removed by evaporation. Purification of the residue by chromatography on silica gel (hexane/ethyl acetate=5/1 to 3/1 as the eluent) gave 2d (185 mg, 93% yield) as a colorless oil.

Reference： [1]Location in patent: experimental part Tayama, Eiji; Sato, Ryota; Takedachi, Keisuke; Iwamoto, Hajime; Hasegawa, Eietsu [Tetrahedron, 2012, vol. 68, # 24, p. 4710 - 4718]

82
[ 17761-41-0 ]
[ 213339-69-6 ]
[ 7476-66-6 ]
[ 345579-56-8 ]

Yield	Reaction Conditions	Operation in experiment
1: 40% 2: 28%	With [2,2]bipyridinyl; copper(l) iodide In acetonitrile at 20℃; for 12h; Inert atmosphere; Sealed tube;

Reference： [1]Miura, Tomoya; Morimoto, Masao; Murakami, Masahiro [Organic Letters, 2012, vol. 14, # 20, p. 5214 - 5217,4]

83
[ 23328-69-0 ]
[ 213339-69-6 ]
[ 7476-66-6 ]
[ 100609-91-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 80% 2: 10%	With [2,2]bipyridinyl; copper(l) iodide In acetonitrile at 20℃; for 12h; Inert atmosphere; Sealed tube;

Reference： [1]Miura, Tomoya; Morimoto, Masao; Murakami, Masahiro [Organic Letters, 2012, vol. 14, # 20, p. 5214 - 5217,4]

84
[ 23328-69-0 ]
[ 40195-27-5 ]
[ 7476-66-6 ]
[ 100609-91-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 39% 2: 29%	With [2,2]bipyridinyl; copper(l) iodide In acetonitrile at 20℃; for 12.5h; Inert atmosphere; Sealed tube;

Reference： [1]Miura, Tomoya; Morimoto, Masao; Murakami, Masahiro [Organic Letters, 2012, vol. 14, # 20, p. 5214 - 5217,4]

85
[ 23328-69-0 ]
[ 82700-21-8 ]
[ 7476-66-6 ]
[ 100609-91-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 57% 2: 20%	With [2,2]bipyridinyl; copper(l) iodide In acetonitrile at 20℃; for 12.5h; Inert atmosphere; Sealed tube;

Reference： [1]Miura, Tomoya; Morimoto, Masao; Murakami, Masahiro [Organic Letters, 2012, vol. 14, # 20, p. 5214 - 5217,4]

86
[ 22979-35-7 ]
[ 15206-55-0 ]
[ 7476-66-6 ]
[ 81265-15-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine; (Dichloroiodo)benzene In dichloromethane at 20℃; for 1h;

Reference： [1]Tao, Jason; Tran, Richard; Murphy, Graham K. [Journal of the American Chemical Society, 2013, vol. 135, # 44, p. 16312 - 16315]

87
[ 26189-59-3 ]
[ 4358-87-6 ]
[ 7476-66-6 ]
C₁₄H₁₈NO₂⁽¹⁺⁾*Cl^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 43 %Spectr. 2: 57 %Spectr.	In dichloromethane at 20℃; for 3h; Inert atmosphere;	4.6.5. Reaction of methyl mandelate with 2a. Procedure A: 1.13 g (6.8 mmol) methyl mandelate, 1 g (7.5 mmol) 2a, 3 h. As shown by 1H NMR, a 1.35/1 mixture of iminium salt 31 and chloride 30 was obtained after 3 h of reaction at room temperature. When reaction was continued for 12 h, the iminium salt slowly gives the ringopening product 32. The same result was obtained if the reaction was refluxed for 2 h.

Reference： [1]Munyemana, François; George, Isabelle; Devos, Alain; Colens, Alain; Badarau, Eduard; Frisque-Hesbain, Anne-Marie; Loudet, Aurore; Differding, Edmond; Damien, Jean-Marie; Rémion, Jeanine; Van Uytbergen, Jacqueline; Ghosez, Léon [Tetrahedron, 2016, vol. 72, # 3, p. 420 - 430]

88
[ 7476-66-6 ]
[ 393-52-2 ]
[ 4358-87-6 ]
2-methoxy-2-oxo-1-phenylethyl 2-fluorobenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
272 mg	With N,N-dimethyl-formamide In 1,4-dioxane at 80℃; for 36h;

Reference： [1]Huy, Peter H.; Motsch, Sebastian; Kappler, Sarah M. [Angewandte Chemie - International Edition, 2016, vol. 55, # 34, p. 10145 - 10149][Angew. Chem., 2016, vol. 128, # 34, p. 10300 - 10304,5]

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Ghs Precautionary Statements

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

Ghs Hazard Statements

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