[ CAS No. 10203-08-4 ] {[proInfo.proName]}

Name: 10203-08-4|3,5-Dichlorobenzaldehyde|98%
Brand: Ambeed
SKU: A455403
Price: 10.0 USD
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Quality Control of [ 10203-08-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 10203-08-4 ]

CAS No. :	10203-08-4	MDL No. :	MFCD00003352
Formula :	C₇H₄Cl₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CASRSOJWLARCRX-UHFFFAOYSA-N
M.W :	175.01	Pubchem ID :	35746
Synonyms :

Calculated chemistry of [ 10203-08-4 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.85
TPSA :	17.07 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) :	-5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.77
Log Po/w (XLOGP3) :	2.64
Log Po/w (WLOGP) :	2.81
Log Po/w (MLOGP) :	2.63
Log Po/w (SILICOS-IT) :	3.26
Consensus Log Po/w :	2.62

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.97
Solubility :	0.189 mg/ml ; 0.00108 mol/l
Class :	Soluble
Log S (Ali) :	-2.65
Solubility :	0.393 mg/ml ; 0.00224 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.57
Solubility :	0.0467 mg/ml ; 0.000267 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.1

Safety of [ 10203-08-4 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	1759
Hazard Statements:	H314	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 10203-08-4 ]

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

Upstream synthesis route of [ 10203-08-4 ]
Downstream synthetic route of [ 10203-08-4 ]

[ 10203-08-4 ] Synthesis Path-Upstream 1~15

1
[ 10203-08-4 ]
[ 3290-06-0 ]

Reference： [1] Monatshefte fuer Chemie, 1933, vol. 62, p. 344,347

2
[ 10203-08-4 ]
[ 60211-57-6 ]
[ 51-36-5 ]

Reference： [1] Monatshefte fuer Chemie, 1933, vol. 62, p. 344,347
[2] Monatshefte fuer Chemie, 1933, vol. 62, p. 344,347

3
[ 25186-47-4 ]
[ 10203-08-4 ]

Yield	Reaction Conditions	Operation in experiment
39.2%	at 105℃; for 0.166667 h;	(1) device: Referring to Figure 2 to determine the connection of the tubular reactor, the pipeline type is:(3a + 3d) DC-channel+ enhanced hybrid round cake rectangular flat pipe,Pipe diameter and volume based on the flow rate and reaction to determine the residence time,Heat transfer medium for thermal oil.(2) 6.06 g of cobalt acetate and 6.06 g of sodium molybdate were dissolved respectively200ml3,5 - dichloro toluene and200ml acetic acid to form a mixed solution,In this case, n (cobalt acetate): n (3,5-dichlorotoluene) = 0.015: 1,6.06 g of sodium bromide was dissolved in 20percent H2O2 to form a H2O2-acetic acid solution, where n (sodium bromide): n (3,5-dichlorotoluene) = 0.015: 1,3,5-dichlorotoluene-acetic acid Solution and andH2O2-acetic acid solution respectively to 8.33ml / min andThe flow rate of 16.67 ml / min was injected into the tubular reactor which was continuously heat-exchanging by the constant current pump, at this time, n (H2O2): n (3,5-dichlorotoluene) = 2:Using the microchannel reactor of Figure 2,The reaction temperature was controlled at 105 ° C and the residence time was 600 s.The outlet was cooled at 0 ° C and the reaction quenched with dichloromethane.After GC analysis, 3,5-dichlorotoluene conversion rate of 60.8percentThe yield of 3,5-dichlorobenzaldehyde was 39.2percent.

Reference： [1] Patent: CN106588606, 2017, A, . Location in patent: Paragraph 0029-0052

4
[ 93033-57-9 ]
[ 10203-08-4 ]

Reference： [1] Synthetic Communications, 1997, vol. 27, # 22, p. 3835 - 3838

5
[ 35515-07-2 ]
[ 10203-08-4 ]

Reference： [1] Organic Syntheses, 2011, vol. 88, p. 427 - 437

6
[ 60211-57-6 ]
[ 10203-08-4 ]

Reference： [1] Tetrahedron, 1993, vol. 49, # 33, p. 7267 - 7276
[2] Organic Letters, 2015, vol. 17, # 20, p. 5048 - 5051

7
[ 89-75-8 ]
[ 10203-08-4 ]

Reference： [1] Chemistry - A European Journal, 2012, vol. 18, # 26, p. 8174 - 8179

8
[ 2905-62-6 ]
[ 10203-08-4 ]

Reference： [1] Journal of the Chemical Society [Section] B: Physical Organic, 1966, p. 1011 - 1015
[2] Organic Syntheses, 2011, vol. 88, p. 427 - 437

9
[ 51-36-5 ]
[ 10203-08-4 ]

Reference： [1] Journal of the Chemical Society [Section] B: Physical Organic, 1966, p. 1011 - 1015

10
[ 7664-93-9 ]
[ 56961-85-4 ]
[ 10203-08-4 ]

Reference： [1] Helvetica Chimica Acta, 1938, vol. 21, p. 1240,1247

11
[ 7732-18-5 ]
[ 10203-08-4 ]

Reference： [1] Monatshefte fuer Chemie, 1933, vol. 62, p. 344,347

12
[ 10203-08-4 ]
[ 14401-72-0 ]

Reference： [1] Chemische Berichte, 1937, vol. 70, p. 916,923

13
[ 10203-08-4 ]
[ 540-69-2 ]
[ 39989-43-0 ]

Reference： [1] Journal of the Karnatak University, 1957, vol. 2, p. 19,26

14
[ 10203-08-4 ]
[ 81290-20-2 ]
[ 130336-16-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 8 h;	Step 1 Method B. l-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (AI2). To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in tetrahydrofuran (THF; 250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25 °C for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with H₂0 and was extracted with ethyl acetate (EtOAc; 3 x). The combined organic extracts were washed with brine, dried over Na₂S0₄, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60percent).

Reference： [1] Patent: WO2014/100163, 2014, A1, . Location in patent: Page/Page column 47

15
[ 10203-08-4 ]
[ 851784-82-2 ]

Reference： [1] Patent: WO2014/18748, 2014, A1,
[2] Patent: WO2014/18748, 2014, A1,

[ 10203-08-4 ] Synthesis Path-Downstream 1~72

1
[ 141-82-2 ]
[ 10203-08-4 ]
[ 20595-53-3 ]

Yield	Reaction Conditions	Operation in experiment
90%	With pyridine; In N,N-dimethyl-formamide; at 30 - 75℃;	A mixture of 3,5-dichlorobenzaldehyde (250.0 g, 1.43 mol), malonic acid (223.0 g, 2.14 mol) and pyridine (250 mL) in DMF (500 mL) was heated at temperatures ranging from 30 C. to 75 C. until the reaction was completed. The mixture was then cooled to 10 to 20 C., and a hydrochloric acid solution (0.6 N, 5 L) was added. The mixture was stirred at 10 to 20 C. for 6 hours and filtered. The filter cake was washed with water, and dried at 40 to 60 C. under vacuum to produce 1 (281 g, 90% yield).
	With piperidine; pyridine; at 90℃;Inert atmosphere;	General procedure: To a stirred solution of malonic acid (10 mmol) in pyridine(5 mL) and piperidine (3-5 drops) the corresponding aldehydes1a-p (8 mmol) were added. The resulting mixture was stirred at 90C for 8-12 h. The progress of the reaction was monitored byTLC analyses which indicated the disappearance of the starting material. After the completion of the reactions the reaction mixture were cooled to ambient temperature and the reaction mixture was neutralized with 1N HCl in ice bath resulting a white solid.This soled was filtered and washed three times with cold water.The recrystallization were done from aqueous ethanol (1:1)afforded the product 2a-p.

Reference： [1]Patent: US2020/197375,2020,A1 .Location in patent: Paragraph 0146
[2]Journal of Medicinal Chemistry,1987,vol. 30,p. 486 - 494
[3]Journal of the Chemical Society,1958,p. 4064,4068
[4]Journal of Medicinal Chemistry,2003,vol. 46,p. 409 - 416
[5]Tetrahedron,2016,vol. 72,p. 7256 - 7262
[6]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5726 - 5732

2
[ 10203-08-4 ]
[ 540-69-2 ]
[ 39989-43-0 ]

Reference： [1]Journal of the Karnatak University,1957,vol. 2,p. 19,26

3
[ 10203-08-4 ]
phenylmagnesium bromide [ No CAS ]
[ 13395-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether

Reference： [1]Lock; Roediger [Chemische Berichte, 1939, vol. 72, p. 861,868]

4
[ 10203-08-4 ]
[ 60211-57-6 ]
[ 51-36-5 ]

Reference： [1]Monatshefte fur Chemie,1933,vol. 62,p. 344,347
[2]Monatshefte fur Chemie,1933,vol. 62,p. 344,347

5
[ 10203-08-4 ]
[ 59178-12-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With sulfuric acid; nitric acid; at 0℃; for 0.5h;	2-Amino-3-(5,7-dichloro-3-methoxy-2H-indazol-2-yl)-2-methylpropionitrile was prepared using a procedure similar to that described in Example 1, part b, except starting from 1-(5,7-dichloro-3-methoxy-2H-indazol-2-yl)propan-2-one. 1-(4,6-dichloro-3-methoxy-2H-indazol-2-yl)propan-2-one was prepared using a procedure similar to that described in Example 116 part a to d except using 3,5-dichloro-2-nitrobenzaldehyde (2.1 g) and decaborane (0.41 g) in part a to yield [2-(tert-butyldimethylsilanyloxy)propyl]-(3,5-dichloro-2-nitrobenzyl)amine (1.2 g, 32%). 3,5-Dichloro-2-nitrobenzaldehyde (2.2 g, 79%) was prepared by nitration of 3,5-dichlorobenzaldehyde (2.2 g) in a mixture of nitric acid (1.5 mL) and sulfuric acid (8 mL) at 0 C. for 30 minutes.
79%	With sulfuric acid; nitric acid; at 0℃; for 0.5h;	2-Amino-3-(5,7-dichloro-3-methoxy-2/-/-indazol-2-yl)-2-methylpropionitrile was prepared using a procedure similar to that described in Example 1 , part b, except starting from 1-(5,7-dichloro -3- methoxy-2/-/-indazol-2-yl)propan-2-one. 1-(4,6-dichloro -3-methoxy-2/-/-indazol-2-yl)propan-2-one was prepared using a procedure similar to that described in Example 105 part a to d except using 3,5- dichloro-2-nitrobenzaldehyde (2.1 g) and decaborane (0.41 g) in part a to yield [2-(tert- butyldimethylsilanyloxy)propyl]-(3,5-dichloro-2-nitrobenzyl)amine (1.2 g, 32%). 3,5-Dichloro-2- nitrobenzaldehyde (2.2 g, 79%) was prepared by nitration of 3,5-dichlorobenzaldehyde (2.2 g) in a mixture of nitric acid (1.5 mL) and sulfuric acid (8 mL) at 00C for 30 minutes.

Reference： [1]Patent: US2010/125089,2010,A1 .Location in patent: Page/Page column 74
[2]Patent: WO2008/144275,2008,A1 .Location in patent: Page/Page column 93
[3]Monatshefte fur Chemie,1933,vol. 63,p. 385,390

6
[ 10203-08-4 ]
[ 108-24-7 ]
[ 20595-53-3 ]

Reference： [1]Monatshefte fur Chemie,1933,vol. 62,p. 344,347

7
[ 10203-08-4 ]
[ 52126-12-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfur tetrafluoride; boron trifluoride

Reference： [1]Rowbotham,J.B. et al. [Canadian Journal of Chemistry, 1974, vol. 52, p. 481 - 488]

8
[ 10203-08-4 ]
[ 598-81-2 ]
[ 65298-12-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1977,vol. 14,p. 1029 - 1033
[2]Journal of Heterocyclic Chemistry,1977,vol. 14,p. 1029 - 1033

9
[ 10203-08-4 ]
[ 598-81-2 ]
[ 65298-12-6 ]

Reference： [1]Journal of Heterocyclic Chemistry,1977,vol. 14,p. 1029 - 1033
[2]Journal of Heterocyclic Chemistry,1977,vol. 14,p. 1029 - 1033

10
[ 542-02-9 ]
[ 10203-08-4 ]
[ 131454-65-4 ]

Yield	Reaction Conditions	Operation in experiment
59%	With methanesulfonic acid at 110℃; for 2.5h;

Reference： [1]Hasegawa; Yanagisawa; Okui; Sato; Hosaka; Chin; Mitsuhashi [Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 12, p. 3180 - 3182]

11
[ 60211-57-6 ]
[ 10203-08-4 ]

Reference： [1]Tetrahedron,1993,vol. 49,p. 7267 - 7276
[2]Organic Letters,2015,vol. 17,p. 5048 - 5051

12
[ 10203-08-4 ]
[ 609-20-1 ]
[ 84562-37-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	In ethanol for 1.5h; Heating;

Reference： [1]Meyer, Walter E.; Tomcufcik, Andrew S.; Chan, Peter S.; Emma, John E. [Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1705 - 1710]

13
[ 10203-08-4 ]
[ 67515-76-8 ]
5-[1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-amino}-pyridine-2-carboxylic acid methyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1980,vol. 23,p. 1405 - 1410

14
[ 10203-08-4 ]
[ 22259-53-6 ]
[1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-(1H-indol-3-ylmethyl)-amine [ No CAS ]

Reference： [1]Archiv der Pharmazie,1994,vol. 327,p. 105 - 114

15
[ 3226-34-4 ]
[ 10203-08-4 ]
[ 15967-33-6 ]

Reference： [1]Monatshefte fur Chemie,1965,vol. 96,p. 1214 - 1223

16
[ 10203-08-4 ]
[ 2892-29-7 ]
[ 15934-91-5 ]

Reference： [1]Monatshefte fur Chemie,1965,vol. 96,p. 1214 - 1223

17
[ 22908-28-7 ]
[ 10203-08-4 ]
[ 56988-31-9 ]

Reference： [1]Journal of Medicinal Chemistry,1975,vol. 18,p. 1011 - 1019

18
[ 10203-08-4 ]
[ 1735-91-7 ]
[ 38635-59-5 ]

Reference： [1]Journal of Medicinal Chemistry,1972,vol. 15,p. 775 - 780

19
[ 10203-08-4 ]
[ 70461-33-5 ]
[ 1026846-16-1 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1293 - 1305

20
[ 59311-67-0 ]
[ 10203-08-4 ]
[1-(3,5-Dichloro-phenyl)-meth-(E)-ylidene]-(2-thiophen-3-yl-ethyl)-amine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 2277 - 2289

21
[ 10203-08-4 ]
[ 27784-76-5 ]
[ 230642-77-0 ]

Yield	Reaction Conditions	Operation in experiment
77%		To a solution of tert-butyldiethylphosphonoacetate (6.94g, 27.5 mmol) in THF (50 ml) at 0C was added slowly sodium hexamethyldisilazide (NaHMDS) (27.5 ml, 27.5 mmol). The resulting solution was warmed to 25C and stirred 30 minutes. After cooling the reaction mixture to 0C, a solution of 3,5-dichlorobenzaldehyde (4.38g, 25 mmol) in THF (25 ml) was slowly added. The reaction mixture was warmed to 25C and stirred overnight. The reaction mixture was poured onto saturated NH4Cl/EtOAc. The aqueous layer was extracted 3 times (X) with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentratedin vacuo. Purification of the crude residue on silica gel (9:1 hexanes-EtOAc) provided 5.19g (77%) of title compound in the form of a white solid.
77%		To a solution of tert-butyldiethylphosphonoacetate (6.94 g, 27.5 mmol) in THF (50 ml) at 0 C. was added slowly sodium hexamethyldisilazide (NaHMDS) (27.5 ml, 27.5 mmol). The resulting solution was warmed to 25 C. and stirred for 30 minutes. After cooling the reaction mixture to 0 C., a solution of 3,5-dichlorobenzaldehyde (4.38 g, 25 mmol) in THF (25 ml) was slowly added. The reaction mixture was warmed to 25 C. and stirred overnight. The reaction mixture was poured onto saturated NH4Cl/EtOAc. The aqueous layer was extracted 3 times with EtOAc. The combined organics were washed with brine, dried over Na2SO4, and concentrated in vacuo. Purification of the crude residue by silica gel chromatography (9:1 hexanes-EtOAc) provided 5.19 g (77%) of title compound in the form of a white solid.

Reference： [1]Journal of Medicinal Chemistry,2001,vol. 44,p. 3302 - 3310
[2]Patent: EP1041980,2005,B1 .Location in patent: Page/Page column 28
[3]Patent: US6887870,2005,B1 .Location in patent: Page/Page column 42

22
[ 10203-08-4 ]
[ 76-05-1 ]
[ 162167-97-7 ]
[1-(3,5-dichlorobenzyl)piperidin-3-yl]methanamine bis(trifluoroacetate) salt [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2004,p. 2723 - 2737

23
[ 10203-08-4 ]
[ 95333-95-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 71 percent / triethylammonium formate 2: 100 percent / H₂O / acetonitrile / 0.5 h / 120 °C / microwave irradiation
	Multi-step reaction with 2 steps 1: pyridine; piperidine / 70 °C 2: H₂ / platinum oxide / aq. ethanol
	Multi-step reaction with 2 steps 1: 69 percent / piperidine / 1.) 100 deg C, 2 h, 2.) 155 deg C, 1 h 2: 95 percent / H₂ / 10 percent Pd/C / tetrahydrofuran / 5 h / 2585.7 Torr

	Multi-step reaction with 2 steps 1: malonic acid / ethanol 2: Pd-C / tetrahydrofuran
	Multi-step reaction with 2 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere 1.2: 2 h / 0 - 20 °C / Inert atmosphere 2.1: 5%-palladium/activated carbon; hydrogen / methanol / 20 °C

Reference： [1]Sharma, Anil K.; Subramani, Amutha V.; Gorman, Christopher B. [Tetrahedron, 2007, vol. 63, # 2, p. 389 - 395]
[2]Musso, David L.; Orr, G. Faye; Cochran, Felicia R.; Kelley, James L.; Selph, Jeffrey L.; Rigdon, Greg C.; Cooper, Barrett R.; Jones, Michael L. [Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 409 - 416]
[3]Kruse; Kaiser; DeWolf Jr.; Frazee; Ross; Wawro; Wise; Flaim; Sawyer; Erickson [Journal of Medicinal Chemistry, 1987, vol. 30, # 3, p. 486 - 494]
[4]Current Patent Assignee: PFIZER INC - US6288120, 2001, B1
[5]Current Patent Assignee: TAIWANJ PHARMACEUTICALS CO LTD - WO2019/108943, 2019, A1

24
[ 10203-08-4 ]
[ 90390-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1 h / 80 °C 2: LiAlH₄ / diethyl ether / 2 h / Heating

Reference： [1]Meindl; Von Angerer; Schonenberger; Ruckdeschel [Journal of Medicinal Chemistry, 1984, vol. 27, # 9, p. 1111 - 1118]

25
[ 10203-08-4 ]
[ 2155-42-2 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1991,vol. 64,p. 2249 - 2254

26
[ 10203-08-4 ]
[ 23082-45-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: nitric acid / 0 °C 2: aqueous potassium permanganate solution

Reference： [1]Asinger [Monatshefte fur Chemie, 1933, vol. 63, p. 385,390]

27
[ 10203-08-4 ]
[ 14401-72-0 ]

Reference： [1]Chemische Berichte,1937,vol. 70,p. 916,923

28
[ 10203-08-4 ]
[ 3290-06-0 ]

Reference： [1]Monatshefte fur Chemie,1933,vol. 62,p. 344,347

29
[ 455-19-6 ]
[ 1948-40-9 ]
[ 2973-77-5 ]
[ 10203-08-4 ]
[ 447-61-0 ]
[ 619-21-6 ]
[ 454-89-7 ]
[ 32085-88-4 ]
[ 39943-56-1 ]
[ 83-38-5 ]
[ 619-67-0 ]
[ 100-52-7 ]
[ 619-66-9 ]
[ 38235-71-1 ]
[ 100-63-0 ]
[ 368-78-5 ]
[ 365-34-4 ]
[ 119-67-5 ]
[ 14763-24-7 ]
[ 5326-27-2 ]
[ 74478-58-3 ]
[ 588-64-7 ]
3-(phenyl-hydrazonomethyl)-benzoic acid [ No CAS ]
N-(2,6-Dichloro-phenyl)-N'-[1-(3,5-dichloro-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
N-(2,6-Dichloro-phenyl)-N'-[1-(3,5-difluoro-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
C₁₅H₁₂N₂O₄ [ No CAS ]
N-(3,5-Dichloro-phenyl)-N'-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
N-(3,5-Dichloro-phenyl)-N'-[1-(4-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
C₁₅H₁₂N₂O₄ [ No CAS ]
N-(2,6-Dichloro-phenyl)-N'-[1-(4-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
C₁₅H₁₂N₂O₄ [ No CAS ]
N-(2,6-Dichloro-phenyl)-N'-[1-(3-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
N-(3,5-Dichloro-phenyl)-N'-[1-(3-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
C₁₅H₁₂N₂O₄ [ No CAS ]
C₁₅H₁₂N₂O₄ [ No CAS ]
C₁₅H₁₂N₂O₄ [ No CAS ]
N-(3-Trifluoromethyl-phenyl)-N'-[1-(3-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
N-(2-Trifluoromethyl-phenyl)-N'-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
4-{N'-[1-(3,5-Dibromo-4-hydroxy-phenyl)-meth-(E)-ylidene]-hydrazino}-benzoic acid [ No CAS ]
N-(3-Trifluoromethyl-phenyl)-N'-[1-(2-trifluoromethyl-phenyl)-meth-(E)-ylidene]-hydrazine [ No CAS ]
2,6-dibromo-4-[(3-trifluoromethyl-phenyl)-hydrazonomethyl]-phenol [ No CAS ]
2,6-dibromo-4-[(2-trifluoromethyl-phenyl)-hydrazonomethyl]-phenol [ No CAS ]
4-{N'-[1-(4-Hydroxy-3,5-diiodo-phenyl)-meth-(E)-ylidene]-hydrazino}-benzoic acid [ No CAS ]
3-{N'-[1-(4-Hydroxy-3,5-diiodo-phenyl)-meth-(E)-ylidene]-hydrazino}-benzoic acid [ No CAS ]
2,6-diiodo-4-[(2-trifluoromethyl-phenyl)-hydrazonomethyl]-phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Combinatorial reaction / High throughput screening (HTS);	Libraries were prepared in a single compound per well format. Stock solutions of all aldehydes (0.5 M) and aryloxyamines (0.4 M) were prepared in DMSO. A Gilson 215 Liquid Handler equipped with a 1 mL syringe, 1.1 mL tubing, and a 13 mm I.D. probe was used to distribute all solutions into a 96 well (2 mL volume) polypropylene plate at a rate of 0.3 mL/min. To make 0.5 mL of a 0.1 M solution of each oxime ether, 100 muL (0.05 mmol, 1 eq.) of aldehyde, 156 muL (0.63 mmol, 1.25 eq.) of aryloxyamine, and 244 muL of 0.164 M acetic acid, were distributed to each well of the plate. The plate was covered and agitated for 24 h at room temperature using a dual action shaker. The reactions were diluted to 720 muM in DMSO and analyzed by LC-MS to determine yield, purity, and identity. Compounds were stored frozen at -20 C. after synthesis. Reaction yield was determined using the integrated value of aldehyde that remained in the reaction mixture. Calibration curves of all aldehydes were made and the yield of each oxime ether was calculated assuming all the aldehyde that reacted quantitatively formed oxime ether; i.e. if 5% of aldehyde remained in the reaction mixture the yield of oxime ether would be 95%. Yields ranged from 98-100% and >95% purity in all wells.

Reference： [1]Patent: US2006/178527,2006,A1 .Location in patent: Page/Page column 4

30
[ 455-19-6 ]
[ 1948-40-9 ]
[ 2973-77-5 ]
[ 4846-21-3 ]
[ 10203-08-4 ]
[ 447-61-0 ]
[ 619-21-6 ]
[ 454-89-7 ]
[ 99907-98-9 ]
[ 32085-88-4 ]
[ 83-38-5 ]
[ 100-52-7 ]
[ 619-66-9 ]
[ 160725-42-8 ]
[ 119-67-5 ]
[ 197588-25-3 ]
[ 99907-90-1 ]
[ 75735-31-8 ]
3-(phenoxyimino-methyl)-benzoic acid [ No CAS ]
2-(phenoxyimino-methyl)-benzoic acid [ No CAS ]
4-(phenoxyimino-methyl)-benzoic acid [ No CAS ]
3,5-dibromo-4-hydroxy-benzaldehyde O-phenyl-oxime [ No CAS ]
3,5-difluoro-benzaldehyde O-(3,5-difluoro-phenyl)-oxime [ No CAS ]
3,5-dichloro-benzaldehyde O-(3,5-difluoro-phenyl)-oxime [ No CAS ]
4-[(3,5-dichloro-phenoxyimino)-methyl]-benzoic acid [ No CAS ]
3-[(3,5-dichloro-phenoxyimino)-methyl]-benzoic acid [ No CAS ]
2-trifluoromethyl-benzaldehyde O-(3,5-dichloro-phenyl)-oxime [ No CAS ]
3-trifluoromethyl-benzaldehyde O-(3,5-dichloro-phenyl)-oxime [ No CAS ]
3-[(3-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid [ No CAS ]
3-trifluoromethyl-benzaldehyde O-(3,5-difluoro-phenyl)-oxime [ No CAS ]
2-trifluoromethyl-benzaldehyde O-(3,5-difluoro-phenyl)-oxime [ No CAS ]
4-trifluoromethyl-benzaldehyde O-(3,5-difluoro-phenyl)-oxime [ No CAS ]
4-[(3-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid [ No CAS ]
3-[(2-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid [ No CAS ]
4-trifluoromethyl-benzaldehyde O-(2-trifluoromethyl-phenyl)-oxime [ No CAS ]
3-trifluoromethyl-benzaldehyde O-(2-trifluoromethyl-phenyl)-oxime [ No CAS ]
2-trifluoromethyl-benzaldehyde O-(2-trifluoromethyl-phenyl)-oxime [ No CAS ]
2-[(2-trifluoromethyl-phenoxyimino)-methyl]-benzoic acid [ No CAS ]
3,5-dibromo-4-hydroxy-benzaldehyde O-(3,5-dichloro-phenyl)-oxime [ No CAS ]
2-trifluoromethyl-benzaldehyde O-(3-trifluoromethyl-phenyl)-oxime [ No CAS ]
3,5-dibromo-4-hydroxy-benzaldehyde O-(3-trifluoromethyl-phenyl)-oxime [ No CAS ]
4-hydroxy-3,5-diiodo-benzaldehyde O-(3-trifluoromethyl-phenyl)-oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 98% 2: 98% 3: 98% 4: 98% 5: 98% 6: 98% 7: 98% 8: 98% 9: 98% 10: 98% 11: 98% 12: 98% 13: 98% 14: 98% 15: 98% 16: 98% 17: 98% 18: 98% 19: 98% 20: 98% 21: 98% 22: 98% 23: 98% 24: 98% 25: 98%	With acetic acid In water; dimethyl sulfoxide at 20℃; for 24h; Combinatorial reaction / High throughput screening (HTS);	Libraries were prepared in a single compound per well format. Stock solutions of all aldehydes (0.5 M) and aryloxyamines (0.4 M) were prepared in DMSO. A Gilson 215 Liquid Handler equipped with a 1 mL syringe, 1.1 mL tubing, and a 13 mm I.D. probe was used to distribute all solutions into a 96 well (2 mL volume) polypropylene plate at a rate of 0.3 mL/min. To make 0.5 mL of a 0.1 M solution of each oxime ether, 100 μL (0.05 mmol, 1 eq.) of aldehyde, 156 μL (0.63 mmol, 1.25 eq.) of aryloxyamine, and 244 μL of 0.164 M acetic acid, were distributed to each well of the plate. The plate was covered and agitated for 24 h at room temperature using a dual action shaker. The reactions were diluted to 720 μM in DMSO and analyzed by LC-MS to determine yield, purity, and identity. Compounds were stored frozen at -20° C. after synthesis. Reaction yield was determined using the integrated value of aldehyde that remained in the reaction mixture. Calibration curves of all aldehydes were made and the yield of each oxime ether was calculated assuming all the aldehyde that reacted quantitatively formed oxime ether; i.e. if 5% of aldehyde remained in the reaction mixture the yield of oxime ether would be 95%. Yields ranged from 98-100% and >95% purity in all wells.

Reference： [1]Current Patent Assignee: SCRIPPS RESEARCH - US2006/178527, 2006, A1 Location in patent: Page/Page column 9

31
[ 110-89-4 ]
[ 10203-08-4 ]
[ 20595-53-3 ]

Yield	Reaction Conditions	Operation in experiment
22.9 g (69%)	With pyridine; malonic acid;	EXAMPLE 26 3-(3', 5'-Dichlorophenyl)propyl-2-mercaptoimidazole Reaction of 3,5-dichlorobenzaldehyde (26.9 g, 0.154 mole), malonic acid (24.1 g, 0.232 mole), pyridine (8 ml) and piperidine (0.4 ml) substantially as above yielded 22.9 g (69%) of 3,5-dichlorocinnamic acid as white needles: mp 169-170 (ethanol).
22.9 g (69%)	With pyridine; malonic acid;	A: 3-(3,5-Dichlorophenyl)propenoic acid 3,5-Dichlorobenzaldehyde (0.154 mol), malonic acid (0.232 mol), pyridine (0.0989 mol) and piperidine (0.004 mol) were reacted substantially as described in Example 7B above to obtain 22.9 g (69%) white crystals: mp 171-172 (ethanol)
	With malonic acid; In ethanol;	Step A 3-(3,5-Dichlorophenyl)-acrylic acid. A mixture of 3,5-dichlorobenzaldehyde (15.0 g, 85.7 mmol), malonic acid (12.5 g, 120.2 mmol), and piperidine (5 mL) was heated at 100 C. for 2 h and at 150 C. for 1 h. The reaction was poured onto 3N HCl (200 mL) and the precipitate was removed via filtration. The product was purified by recrystallization (100 mL hot EtOH) to afford 3-(3,5-dichlorophenyl)-acrylic acid (11.5 g). 1H NMR (250 MHz, DMSO-d6) δ 12.6 (bs, 1H), 7.83 (m, 2H), 7.64-7.51 (m, 2H), 6,72 (d, 1H).

With malonic acid; In ethanol;

Step A 3-(3,5-Dichlorophenyl)-acrylic acid A mixture of 3,5-dichlorobenzaldehyde (15.0 g, 85.7 mmol), malonic acid (12.5 g, 120.2 mmol), and piperidine (5 mL) was heated at 100 C. for 2 h and at 150 C. for 1 h. The reaction was poured onto 3N HCl (200 mL) and the precipitate was removed via filtration. The product was purified by recrystallization (100 mL hot EtOH) to afford 3-(3,5-dichlorophenyl)-acrylic acid (11.5 g). 1H NMR (250 MHz, DMSO-d6) δ12.6 (bs, 1H), 7.83 (m, 2H), 7.64-7.51 (m, 2H), 6.72 (d, 1H).

Reference： [1]Patent: US4992459,1991,A
[2]Patent: US4707488,1987,A
[3]Patent: US6288120,2001,B1
[4]Patent: US6344485,2002,B1

32
[ 10203-08-4 ]
[ 6622-92-0 ]
2-[2-(3,5-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	In acetic anhydride;	b) In analogy to example 12b), from <strong>[6622-92-0]2,4-dimethyl-6-hydroxypyrimidine</strong> (2 g, 16.1 mmol) and 3,5-dichloro-benzaldehyde (2.8 g, 16 mmol) in acetic anhydride there was obtained 2-[2-(3,5-dichloro-phenyl)-vinyl]-6-methyl-pyrimidin-4-ol (4.24 g, 93%) as an light-red solid. ISP mass spectrum, m/e: 281.1 (M+1 calculated for C13H10Cl2N2O: 281).

Reference： [1]Patent: US2002/86858,2002,A1

33
[ 10203-08-4 ]
[ 601-75-2 ]
[ 147524-80-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium acetate; In ethanol; water; acetonitrile;	EXAMPLE 19 Preparation of Ethyl 3-amino-3-(3,5-dichlorophenyl)propanoate, TFA 3,5-dichlorobenzaldehyde (1.75 g; 10 mmol) was dissolved in 50 mL ethanol. Ammonium acetate (1.9 g; 25 mmol) and ethyl-hydrogen-malonate (2 mL; 20 mmol) were added to the solution. It was stirred at reflux for 4h. Ethanol was evaporated and the residue was dissolved in 10% acetonitrile/H2 O and it was purified on HPLC. Ethyl 3-amino-3-(3,5-dichlorophenyl)-propanoate was isolated after lyophilization. FAB-MS: (MH+)=282.1.

Reference： [1]Patent: US5220050,1993,A

34
[ 6443-85-2 ]
[ 10203-08-4 ]
[ 584-08-7 ]
trans-2-(pyridin-3-yl)-3-(3,5-dichlorophenyl)-2-propenenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	In ethanol; water;	trans-2 -(3-Pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile To a stirred solution of 400 g (2.3 mole) 3,5-dichlorobenzaldehyde in 11.4 liters absolute ethanol were added 283.5 g (2.4 mole) <strong>[6443-85-2]3-pyridylacetonitrile</strong> and 720.9 g of K2 CO3. Within 2 minutes of the K2 CO3 addition, a solid precipitate formed. The reaction mixture was stirred about 2.5 hours. Water (22.9 liters) was added to the stirred reaction mixture. After stirring for 1 hour, the mixture was filtered and the filter cake was washed with water (10 liters), dried and recrystallized from isopropanol. Five hundred thirty four g (85% yield) of trans-2-(3-pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile were obtained, m.p. 150-151 C.
85%	In ethanol; water;	Example 1A trans-2-(3-Pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile To a stirred solution of 400 g (2.3 mole) 3,5-dichlorobenzaldehyde in 11.4 liters absolute ethanol were added 283.5 g (2.4 mole) <strong>[6443-85-2]3-pyridylacetonitrile</strong> and 720.9 g of K2 CO3. Within 2 minutes of the K2 CO3 addition, a solid precipitate formed. The reaction mixture was stirred about 2.5 hours. Water (22.9 liters) was added to the stirred reaction mixture. After stirring for 1 hour, the mixture was filtered and the filter cake was washed with water (10 liters), dried and recrystallized from isopropanol. Five hundred thirty four g (85% yield) of trans-2-(3-pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile were obtained, m.p. 150-151 C.
	In ethanol;	EXAMPLE 1B Mixture of cis- and trans-2-(3-pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile To a stirred solution of 3.0 g (17.1 mmole) 3,5-dichlorobenzaldehyde in 200 ml absolute ethanol were added 1.83 ml (17.1 mmole) <strong>[6443-85-2]3-pyridylacetonitrile</strong> and 1 equivalent K2 CO3 (2.36 g). The reaction flask was equipped with a reflux condenser and the stirred reaction mixture was refluxed for 2 hours, filtered and concentrated. The resulting residue was purified by flash chromatography on silica gel, eluding with 4:1 hexane/ethyl acetate to give a mixture of cis- and trans-2-(3-pyridyl)-3-(3,5-dichlorophenyl)-2-propenenitrile.

Reference： [1]Patent: US5302606,1994,A
[2]Patent: US5418245,1995,A
[3]Patent: US5302606,1994,A

35
[ 10203-08-4 ]
[ 120-35-4 ]
3-(3,5-Dichloro-benzylamino)-4-methoxy-N-phenyl-benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid;	Example 51 3-(3,5-Dichloro-benzylamino)-4-methoxy-N-phenyl-benzamide Prepared according to the procedure of Example 50 using 3,5-dichloro-benzaldehyde (0.88 g, 5.0 mmol), 3-amino-4-methoxy-N-phenyl-benzamide (1.22 g, 5.0 mmol), acetic acid (0.24 g, 5.3 mmol), and sodium triacetoxyborohydride (1.12 mmol) to afford the product (0.65 g); m.p. 164-165 C. after recrystallization from ethanol. Calculated for C21H18Cl2N2O2: C, 62.86; H, 4.52; N, 6.98. Found: C, 62.58; H, 4.41; N, 6.83.

Reference： [1]Patent: US6268387,2001,B1

36
[ 109-97-7 ]
[ 10203-08-4 ]
[ 3264-82-2 ]
(C₆H₃Cl₂)4C₂₀H₈N₄Ni [ No CAS ]
[Cl₂C₆H₃CC₄H₂NC(O)(C₆H₃Cl₂)(C₄H₂N)]3Ni₃ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 2306 - 2309

37
[ 10203-08-4 ]
[ 645-36-3 ]
[ 1000210-73-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	In toluene; for 2.5h;Reflux;	The 2,2-Diethoxy-ethylamine (1852.5 g; 1.00 equiv; 13.63 moles), 3,5-dichloro-benzaldehyde (2453 g; 1.00 equiv; 13.60 moles), and Toluene (12 L) is charged to a 22 L flask equipped with a Dean Stark trap, condenser, nitrogen inlet, overhead stirring, and thermocouple. The light yellow reaction is warmed to reflux. Solvent begins distilling at 88 C. A total of 650 mL distillate (240 mL of water) is collected. The temperature is increased to 114 C. during the distillation. NMR after 2 hr at reflux shows the product. The heat is shut off after 2.5 hr. The solution is gravity filtered into a carboy through fluted filter paper to remove a few particulates (including a small section of glass tubing, which is most likely from the 3,5-dichloro-benzaldehyde). The filtered solution is concentrated using Buchi flask with the water bath set at 45 C. Once the solvent stops coming over, the temperature is increased to 70 C. with full vacuum and held for 1.5 hr to remove any residual toluene. The weight of (3,5-Dichloro-benzylidene)-(2,2-diethoxy-ethyl)-amine is 4059.3 g (102.9% of theory). Mass Spectrum (LCMS) m/z=291.2) (M+H+)
94%	In ethanol; at 20 - 78℃; for 2h;	[00114] To a glass reactor was charged 3,5-dichlorobenzaldehyde. Absolute ethanol was added to the batch slowly (this addition is mildly exothermic) and agitation started. 2,2- Diethoxyethylamine (1.03 equiv) was slowly added to the batch, keeping the batch temperature at 20-78 C. The batch was then heated to 76-78 C for 2 h. GC-MS analysis indicated reactioncompletion (starting material < 1%). The batch was cooled to ambient temperature for work-up. The batch was concentrated in vacuo to a residue and azeotroped with heptanes (x2). The residue was cooled and held at 0-5 C for 12 h to form a suspension. The solids were collected by filtration and the cake was washed with cold (0-5 C) heptanes, and dried under hot nitrogen (45-5 0 C) to afford Compound 2? as a white solid (94% yield).

Reference： [1]Patent: US2009/221633,2009,A1 .Location in patent: Page/Page column 4; 5
[2]Patent: WO2014/18748,2014,A1 .Location in patent: Paragraph 00113; 00114
[3]Patent: CN111057003,2020,A .Location in patent: Paragraph 0086-0088

38
[ 10203-08-4 ]
[ 4783-68-0 ]
[ 1173294-99-9 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3120 - 3123

39
[ 10203-08-4 ]
[ 100-58-3 ]
[ 13395-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	In diethyl ether Reflux;

Reference： [1]Location in patent: scheme or table Pajouhesh, Hassan; Feng, Zhong-Ping; Ding, Yanbing; Zhang, Lingyun; Pajouhesh, Hossein; Morrison, Jerrie-Lynn; Belardetti, Francesco; Tringham, Elizabeth; Simonson, Eric; Vanderah, Todd W.; Porreca, Frank; Zamponi, Gerald W.; Mitscher, Lester A.; Snutch, Terrance P. [Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 4, p. 1378 - 1383]

40
[ 1169942-85-1 ]
[ 10203-08-4 ]
BF-175 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide With sodium tertiary butoxide In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: 3,5-dichlorobenzaldehyde In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	Preparation of compound BF175: A mixture of compound 3 (560 mg, 1.0 mmol) and sodium tert-butoxide (tBuONa, 288 mg, 3.0 mmol) in DMF (10 mL) was stirred at room temperature under nitrogen for 10 min. To this solution, 3,5-dichlorobenzaldehyde (175 mg, 1.0 mmol) was added and the resulting mixture was stirred at room temperature for 6 h. The reaction mixture was treated with water (20 mL) and neutralized with 1 M HCl, then extracted with EtOAc (3×10 mL), washed with brine, and finally dried with MgSO4. The solvent was evaporated under reduced pressure. The product was purified by silica gel column chromatography (EtOAc/hexane 1:10) to afford a mixture of E/Z BF175 (161 mg, 43%) as a white solid. 1H NMR (400 MHz, CDCl3): 7.82 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.37 (d, J=2.0 Hz, 2H), 7.24 (t, J=1.6 Hz, 1H), 7.11 (d, J=16.4 Hz, 1H), 7.01 (d, J=16.4 Hz, 1H), 1.36 (s, 12H).
43%	Stage #1: 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-3-yl-phenyl)-methyl triphenylphosphonium bromide With sodium tertiary butoxide In N,N-dimethyl-formamide for 0.166667h; Inert atmosphere; Stage #2: 3,5-dichlorobenzaldehyde In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	Preparation of compound BF175: A mixture of compound 3 (560 mg, 1.0 mmol) and sodium tert-butoxide (tBuONa, 288 mg, 3.0 mmol) in DMF (10 mL) was stirred at room temperature under nitrogen for 10 min. To this solution, 3,5-dichlorobenzaldehyde (175 mg, 1.0 mmol) was added and the resulting mixture was stirred at room temperature for 6 h. The reaction mixture was treated with water (20 mL) and neutralized with 1 M HCl, then extracted with EtOAc (3×10 mL), washed with brine, and finally dried with MgSO4. The solvent was evaporated under reduced pressure. The product was purified by silica gel column chromatography (EtOAc/hexane 1:10) to afford a mixture of E/Z BF175 (161 mg, 43%) as a white solid. 1H NMR (400 MHz, CDCl3): 7.82 (d, J=8.0 Hz, 2H), 7.49 (d, J=8.0 Hz, 2H), 7.37 (d, J=2.0 Hz, 2H), 7.24 (t, J=1.6 Hz, 1H), 7.11 (d, J=16.4 Hz, 1H), 7.01 (d, J=16.4 Hz, 1H), 1.36 (s, 12H).
	With potassium-t-butoxide In bromure d'ethyle at 20℃; for 2h;

Reference： [1]Current Patent Assignee: CITY UNIVERSITY OF HONG KONG - US2021/386714, 2021, A1 Location in patent: Paragraph 0078; 0081
[2]Current Patent Assignee: CITY UNIVERSITY OF HONG KONG - US2021/386714, 2021, A1 Location in patent: Paragraph 0078; 0081
[3]Location in patent: scheme or table Das, Bhaskar C.; Zhao, Xiaoping; Tang, Xiang-Ying; Yang, Fajun [Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 18, p. 5638 - 5641]

41
[ 10203-08-4 ]
[ 1025967-78-5 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 203 - 206
[2]Patent: WO2014/18748,2014,A1
[3]Patent: WO2014/18748,2014,A1
[4]Patent: WO2014/18748,2014,A1
[5]Patent: WO2014/18748,2014,A1

42
[ 7025-19-6 ]
[ 10203-08-4 ]
[ 1367579-50-7 ]

Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 352 - 356

43
[ 10203-08-4 ]
[ 81290-20-2 ]
[ 1187989-89-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: 3,5-dichlorobenzaldehyde; (trifluoromethyl)trimethylsilane In tetrahydrofuran at 25℃; for 8h; Stage #2: With hydrogenchloride; water In tetrahydrofuran for 16h;	1.1.B Step 1 Method B. 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (A12); To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in tetrahydrofuran (THF; 250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25° C. for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with H2O and was extracted with ethyl acetate (EtOAc; 3×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%).
60%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 8h;	1.1.B Step 1 Method B. 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (AI2) To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in THF (250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25° C. for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with H2O and was extracted with ethyl acetate (EtOAc; 3×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%).
60%	Stage #1: 3,5-dichlorobenzaldehyde; (trifluoromethyl)trimethylsilane With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 8h; Stage #2: With hydrogenchloride In tetrahydrofuran; water for 16h;	1.1B 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (AI2) To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in tetrahydrofuran (THF; 250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25° C. for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with H2O and was extracted with ethyl acetate (EtOAc; 3*). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%).

60%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 8h;	1.1.B 1-(3,5-dichlorophenyl)-2,2,2-trifluoroethanol (A12) To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in tetrahydrofuran (THF; 250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25 °C for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with H20 and was extracted with ethyl acetate (EtOAc; 3 x). The combined organic extracts were washed with brine, dried over Na2S04, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%).
60%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 8h;	1.1.B Step 1 Method B. 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (AI2) To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in THF (250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of tetrabutylammonium fluoride (TBAF). The reaction mixture was stirred at 25° C. for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N hydrochloric acid (HCl) and then was stirred for 16 h. The reaction mixture was diluted with water and was extracted with ethyl acetate (EtOAc; 3×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%).
60%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 25℃; for 8h;	1.1 Step 1 Method B.1 -(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (Cl) Step 1 Method B. 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (C1) To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in tetrahydrofuran (250 mL) were added trifluoromethyltrimethylsilane (9.8 g, 69 mmol) and a catalytic amount of tetrabutylammonium fluoride. The reaction mixture was stirred at 25° C. for 8 hours. After the reaction was deemed complete by thin layer chromatography, the reaction mixture was diluted with hydrochloric acid (3 N) and then was stirred for 16 hours. The reaction mixture was diluted with water and was extracted with ethyl acetate (3 times). The combined organic extracts were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to afford the title compound as a liquid (8.4 g, 60%).
	With tetrabutyl ammonium fluoride In tetrahydrofuran	1.M Step 1 Method B. Step 1 Method B. 1-(3,5-Dichlorophenyl)-2,2,2-trifluoroethanol (AI2) To a stirred solution of 3,5-dichlorobenzaldehyde (10 g, 57 mmol) in THF (250 mL) were added trifluoromethyltrimethylsilane (9.79 g, 69.2 mmol) and a catalytic amount of TBAF. The reaction mixture was stirred at 25° C. for 8 h. After the reaction was deemed complete by TLC, the reaction mixture was diluted with 3 N HCl and then was stirred for 16 h. The reaction mixture was diluted with water and was extracted with ethyl acetate (EtOAc; 3*). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure to afford the title compound as a liquid (8.41 g, 60%). The following compounds were made in accordance with the procedures disclosed in Step 1 Method A of Example 1 above.

Reference： [1]Current Patent Assignee: CORTEVA INC - US2012/329649, 2012, A1 Location in patent: Page/Page column 25
[2]Current Patent Assignee: CORTEVA INC - US2014/171308, 2014, A1 Location in patent: Paragraph 0192
[3]Current Patent Assignee: CORTEVA INC - US2014/171312, 2014, A1 Location in patent: Paragraph 0187
[4]Current Patent Assignee: CORTEVA INC - WO2014/100206, 2014, A1 Location in patent: Page/Page column 48
[5]Current Patent Assignee: CORTEVA INC - US9211280, 2015, B2 Location in patent: Page/Page column 46
[6]Current Patent Assignee: CORTEVA INC - US2015/353477, 2015, A1 Location in patent: Paragraph 0141
[7]Current Patent Assignee: CORTEVA INC - US2014/171314, 2014, A1 Location in patent: Page/Page column

44
[ 1136-86-3 ]
[ 10203-08-4 ]
[ 1442690-93-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium hydroxide In methanol at 20℃; for 24h;	2.1.1. Preparation of compounds General procedure: Reagents used were obtained commercially from Sigma-Aldrich. Type 1 and 2 chalcones were prepared by aldol condensation of acetophenones (1 mmol) with aldehydes (1 mmol), in methanol (15 mL), KOH (50% v/v), at room temperature with magnetic agitation for 24 h. The volume of KOH varied according to the different inductive and mesomeric effects for the various substituents of the aromatic rings: 2 mL for compounds 2a, 2b and 2c; 40 drops for compounds 2d and 3p; 15 drops for compounds 3d and 3q; 13 drops for compounds 3a, 3h, 3j and 3o; 10 drops for compounds 3b, 3c, 3e, 3f, 3i and 3k; 8 drops for compounds 3n, 3r and 3s; and 5 drops for compounds 3g, 3l and 3m. KOH addition was stopped at the first sign of precipitation. Distilled water and 10% hydrochloric acid were added to the reaction for total precipitation of the compounds, which were then obtained by vacuum filtration and later recrystallized in dichloromethane, with forced precipitation by hexane. The purity of the synthesized compounds was analyzed by thin-layer chromatography (TLC) using Merck silica pre-coated aluminum plates of 200 mm thickness, with several solvent systems of different polarities. Compounds were visualized with ultraviolet light (λ = 254 and 360 nm) and using sulfuric anisaldehyde solution followed by heat application as the developing agent. The chalcones were soluble in dimethyl sulfoxide, acetone, acetyl acetate, chloroform and dichloromethane. Compounds 3a-3o and 3r were previously cited in the literature [6,7,16-21]. Chalcone derivatives 2a, 2b and 2c were previously synthesized by our group [13-15] and 2d, 3p, 3q and 3s are novel compounds.

Reference： [1]Salum, Lívia B.; Altei, Wanessa F.; Chiaradia, Louise D.; Cordeiro, Marlon N.S.; Canevarolo, Rafael R.; Melo, Carolina P.S.; Winter, Evelyn; Mattei, Bruno; Daghestani, Hikmat N.; Santos-Silva, Maria Cláudia; Creczynski-Pasa, Tânia B.; Yunes, Rosendo A.; Yunes, José A.; Andricopulo, Adriano D.; Day, Billy W.; Nunes, Ricardo J.; Vogt, Andreas [European Journal of Medicinal Chemistry, 2013, vol. 63, p. 501 - 510]

45
[ 10203-08-4 ]
[ 21667-62-9 ]
[ 113-00-8 ]
[ 1441962-06-6 ]

Reference： [1]ACS Combinatorial Science,2013,vol. 15,p. 370 - 378

46
[ 67-56-1 ]
[ 10203-08-4 ]
[ 2905-67-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With Oxone; indium(III) triflate; for 2.5h;Reflux;	General procedure: The starting aldehydematerials (1 mmol) were dissolved in MeOH (5 mL),and Oxone (1 mmol) and 10 mol % of In(OTf)3 were added atroom temperature. The reaction mixture was heated at reflux,and was monitored for completion by TLC. After the reactionmixture was filtered, the filtrate was condensed using arotary evaporator. Flash column chromatography on silica gelfurnished the corresponding products, which were confirmedby spectroscopy.

Reference： [1]Chemical and Pharmaceutical Bulletin,2013,vol. 61,p. 870 - 872

47
[ 10203-08-4 ]
[ 73075-47-5 ]

Reference： [1]Patent: WO2014/18748,2014,A1
[2]Patent: CN111057003,2020,A
[3]Patent: CN112500343,2021,A

48
[ 119072-55-8 ]
[ 10203-08-4 ]
[ 74784-70-6 ]
[ 1610451-26-7 ]

Yield	Reaction Conditions	Operation in experiment
46.5%	With toluene-4-sulfonic acid; In methanol; at 20℃; for 2h;Inert atmosphere;	5-(trifluoromethyl)pyridin-2-amine (200 mg, 1.23 mmol, Eq: 1.00), 3,5-dichlorobenzaldehyde (227 mg, 1.3 mmol, Eq: 1.05) and p-toluenesulfonic acid monohydrate (70.4 mg, 370 muiotaetaomicron, Eq: 0.3) were dissolved in MeOH (1.5 mL). The resulting colorless solution was stirred at rt. To this solution was added dropwise 2-isocyano-2-methylpropane (103 mg, 140 mu, 1.23 mmol, Eq: 1.00) and the corresponding yellow solution was stirred for 2h. To the yellow clear solution was added dropwise water until the mixture got turbid. After stirring for a few additional minutes, the product precipitated. The solid was filtered off, washed with MeOH/water (1: 1) and with hexane and the crystals were dried under vacuum to yield a white solid (231 mg, 46.5%). MS: 402 [M]+; 1H-NMR (D6-DMSO): delta 8.91 (s, 1H), 8.30 (d, 2H), 7.73 (d, 1H), 7.57 (t, 1H), 7.49 (d, 1H), 5.05 (s, 1H), 1.07 (s, 9H).

Reference： [1]Patent: WO2014/76021,2014,A1 .Location in patent: Page/Page column 16; 17

49
[ 6310-09-4 ]
[ 10203-08-4 ]
[ 1579254-74-2 ]

Yield	Reaction Conditions	Operation in experiment
67%	With sodium hydroxide; In methanol; at 20℃;	General procedure: A mixture of <strong>[6310-09-4]2-acetyl-5-chlorothiophene</strong> (0.01 mol) and a halogen-substituted benzaldehyde (0.01 mol)was dissolved in methanol (20 mL). Catalytic amount of NaOH was added to the solution drop-wisewith vigorous stirring. The reaction mixture was stirred for about 5-6 h at room temperature. Theresultant crude products were filtered, washed successively with distilled water and recrystallized fromethanol to get corresponding chalcones. Crystals suitable for X-ray diffraction studies were obtainedby the slow evaporation technique using a suitable solvent, (2E)-1-(5-Chlorothiophen-2-yl)-3-(3,5-dichlorophenyl)prop-2-en-1-one (3h): Solvent for growingcrystals: Mixture of acetone, ethanol and ethyl acetate (1:1:1 v/v); Yield: 67%; M.P. 129-131 C;LCMS: m/z = 318 (M++1); Elemental analysis: Calculated for C13H7Cl3OS: C, 49.16%; H, 2.22%;Found: C, 49.13%; H, 2.29%. CCDC No.: 946445.

Reference： [1]Molecules,2013,vol. 18,p. 12707 - 12724

50
[ 10203-08-4 ]
[ 1187989-89-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h / 25 °C 2: sodium tetrahydroborate; sodium hydroxide / methanol / 2 h / 0 - 25 °C

Reference： [1]Current Patent Assignee: CORTEVA INC - WO2014/100163, 2014, A1

51
[ 10203-08-4 ]
malonic [ No CAS ]
[ 20595-53-3 ]

Reference： [1]Letters in drug design and discovery,2015,vol. 12,p. 20 - 28

52
[ 10203-08-4 ]
[ 74-89-5 ]
[ 90390-21-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3,5-dichlorobenzaldehyde; methylamine In methanol at 20℃; for 0.5h; Stage #2: With sodium tetrahydroborate In methanol at 0 - 20℃; for 1h;

Reference： [1]Zhang, Yinan; Zhao, Kevin Tianmeng; Fox, Susan G.; Kim, Jinho; Kirsch, Donald R.; Ferrante, Robert J.; Morimoto, Richard I.; Silverman, Richard B. [Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 5942 - 5949]

53
[ 10203-08-4 ]
[ 139512-70-2 ]
6-chloro-2-(3,5-difluorophenyl)-5-fluoro-1H-benzimidazole [ No CAS ]

Reference： [1]Chemical Biology and Drug Design,2016,vol. 87,p. 57 - 68

54
[ 10203-08-4 ]
[ 13990-04-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: piperidine / dimethyl sulfoxide / 0.33 h / 60 °C / Microwave irradiation; Sealed tube 2: ammonium hydroxide; carbon dioxide / dimethyl sulfoxide / 12 h / 37 °C / pH 10 / Enzymatic reaction

Reference： [1]Parmeggiani, Fabio; Ahmed, Syed T.; Weise, Nicholas J.; Turner, Nicholas J. [Tetrahedron, 2016, vol. 72, # 46, p. 7256 - 7262]

55
[ 10203-08-4 ]
[ 1145-93-3 ]
1,3-dichloro-5-[(1E)-2-(4-methoxyphenyl)ethenyl]benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium methylate In N,N-dimethyl-formamide at 80℃; for 24h;	5 Example 5: Preparation of (E)-1,3-dichloro-5-(4-methoxystyryl)benzene (C43) Sodium methoxide powder (98%, 0.63 g, 11 mmol) was added to a stirred solution of 3,5-dichlorobenzaldehyde (2.0 g, 11 mmol) a nd diethyl 4-methoxybenzylphosphonate (2.0 mL, 11 mmol) in dry /V, N-dimethylformamide (38 ml_) at 23 °C. The resulting heterogeneous dark blue mixture was heated to 80 °C, resulting in a dark brown mixture, and stirred for 24 hours. The cooled reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (3 x 100 mL) . The combined organic layers were diluted with hexane ( 150 mL) and washed with water (300 mL) . The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford the title product as a light brown oil (2.4 g, 75%) : 'H NM R (400 MHz, CDCb) δ 7.44 (m, 2H), 7.34 (d, J = 2 Hz, 2H ), 7.20 (t, J = 2 Hz, 1H), 7.06 (d, J = 16.5 Hz, 1H), 6.91 (m, 2H), 6.82 (d, J = 16.5 Hz, 1H), 3.84 (s, 3H) ; IR (thin film) 2934 (w), 2835 (w), 1724 (w), 1637 (w), 1605 (m), 1581 (m), 1558 (m), 1511 (s) cnr1.
75%	With sodium methylate In N,N-dimethyl-formamide at 23 - 80℃; for 24h;	47 Preparation of (E)-1,3-dichloro-5-(4-methoxystyryl)benzene (C61) Example 47 Preparation of (E)-1,3-dichloro-5-(4-methoxystyryl)benzene (C61) Sodium methoxide powder (98%, 0.63 g, 11 mmol) was added to a stirred solution of 3,5-dichlorobenzaldehyde (2.0 g, 11 mmol) and diethyl 4-methoxybenzylphosphonate (2.0 mL, 11 mmol) in dry N,N-dimethylformamide (38 mL) at 23° C. The resulting heterogeneous dark blue mixture was heated to 80° C., resulting in a dark brown mixture, and stirred for 24 hours. The cooled reaction mixture was diluted with water (500 mL) and extracted with diethyl ether (3*100 mL). The combined organic layers were diluted with hexane (150 mL) and washed with water (300 mL). The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford the title product as a light brown oil (2.4 g, 75%): 1H NMR (400 MHz, CDCl3) δ 7.44 (m, 2H), 7.34 (d, J=2 Hz, 2H), 7.20 (t, J=2 Hz, 1H), 7.06 (d, J=16.5 Hz, 1H), 6.91 (m, 2H), 6.82 (d, J=16.5 Hz, 1H), 3.84 (s, 3H); IR (thin film) 2934 (w), 2835 (w), 1724 (w), 1637 (w), 1605 (m), 1581 (m), 1558 (m), 1511 (s) cm-1.

Reference： [1]Current Patent Assignee: CORTEVA INC - WO2016/168059, 2016, A1 Location in patent: Page/Page column 78
[2]Current Patent Assignee: CORTEVA INC - US2018/98541, 2018, A1 Location in patent: Paragraph 1371-1372

56
[ 10203-08-4 ]
[ 52509-14-5 ]
(Z)-2-(3,5-dichlorostyryl)-1,3-dioxolane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With Tris(3,6-dioxaheptyl)amine; potassium carbonate; In dichloromethane; water; for 20h;Reflux;	Tris(dioxN-3,6-heptyl)amine (27.7 g, 86.0 mmol) was added dropwise to a stirred solution of 3,5-dichlorobenzaldehyde ( 15 g, 86 mmol), and (( 1,3-dioxolan-2-yl)methyl)triphenylphosphonium bromide (36.8 g, 86 mmol) in 1 : 1 dichloromethane/water (400 mL) . To the biphasic mixture was then added potassium carbonate ( 11.85 g, 86 mmol) . The reaction mixture was heated at reflux for a total of 20 hours, cooled, and poured into water (200 mL). The aqueous mixture was extracted with dichloro metha ne (3 x 100 mL) . The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure on a rotary evaporator. Purification by silica gel flash chromatography with a mobile phase of ethyl acetate and hexanes gave (Z)-2-(3,5-dichlorostyryl)-l ,3-dioxolane as a waxy white solid ( 11.2 g, 53%) : NM R (400 MHz, CDCI3) delta 7.37 - 7.18 (m, 3H), 6.65 (d, J = 11.7 Hz, 1 H), 5.80 (dd, J = 11.8, 7.4 Hz, 1 H), 5.43 (dd, J = 7.4, 0.9 Hz, 1H), 4. 18 - 4.02 (m, 2H), 4.03 - 3.87 (m, 2H) ; EIMS m/z 245.

Reference： [1]Patent: WO2016/168059,2016,A1 .Location in patent: Page/Page column 445-446

57
[ 25186-47-4 ]
[ 10203-08-4 ]

Yield	Reaction Conditions	Operation in experiment
39.2%	With sodium molybdate; dihydrogen peroxide; cobalt(II) acetate; acetic acid; sodium bromide; at 105℃; for 0.166667h;	(1) device: Referring to Figure 2 to determine the connection of the tubular reactor, the pipeline type is:(3a + 3d) DC-channel+ enhanced hybrid round cake rectangular flat pipe,Pipe diameter and volume based on the flow rate and reaction to determine the residence time,Heat transfer medium for thermal oil.(2) 6.06 g of cobalt acetate and 6.06 g of sodium molybdate were dissolved respectively200ml3,5 - dichloro toluene and200ml acetic acid to form a mixed solution,In this case, n (cobalt acetate): n (<strong>[25186-47-4]3,5-dichlorotoluene</strong>) = 0.015: 1,6.06 g of sodium bromide was dissolved in 20% H2O2 to form a H2O2-acetic acid solution, where n (sodium bromide): n (<strong>[25186-47-4]3,5-dichlorotoluene</strong>) = 0.015: 1,<strong>[25186-47-4]3,5-dichlorotoluene</strong>-acetic acid Solution and andH2O2-acetic acid solution respectively to 8.33ml / min andThe flow rate of 16.67 ml / min was injected into the tubular reactor which was continuously heat-exchanging by the constant current pump, at this time, n (H2O2): n (<strong>[25186-47-4]3,5-dichlorotoluene</strong>) = 2:Using the microchannel reactor of Figure 2,The reaction temperature was controlled at 105 C and the residence time was 600 s.The outlet was cooled at 0 C and the reaction quenched with dichloromethane.After GC analysis, <strong>[25186-47-4]3,5-dichlorotoluene</strong> conversion rate of 60.8%The yield of 3,5-dichlorobenzaldehyde was 39.2%.

Reference： [1]Patent: CN106588606,2017,A .Location in patent: Paragraph 0029-0052

58
[ 10203-08-4 ]
[ 1986-47-6 ]
(1S*,2R*)-N-(3,5-dichlorobenzyl)-2-phenylcyclopropan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12%		General procedure: Trans-2-phenylcyclopropylamine hydrochloride (1.0 eq.), acetic acid (1.0eq.) and the appropriate aldehyde (0.9 eq.) were dissolved in around bottom flask in 10 mL dry DCE. The reaction mixture was stirred gently at room temperature for 2 h before sodium triacetoxyborohydride (3.0 eq.) was added in small portions to the reaction vessel. The reaction was monitored by TLC and quenched using 10 mL of an aqueous (5%) NaHCO3 solution. The organic layer was separated and the aqueous layer extracted three times with10 mL of DCE. All organic layers were combined, dried over anhydrous Na2SO4, concentrated in vacuo and purified using flash chromatography (silica gel; cyclohexane/ethyl acetate) to give the desired compound.

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 144,p. 52 - 67

59
[ 10203-08-4 ]
[ 1779-49-3 ]
[ 2155-42-2 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 3547 - 3550

60
[ 10203-08-4 ]
[ 591-51-5 ]
[ 13395-70-5 ]

Yield	Reaction Conditions	Operation in experiment
90%	In tetrahydrofuran at -78℃; Inert atmosphere;	Method B5: General procedure: To a solution of aldehyde (1 mmol) in anhydrous THF at -78°C was added a solutionof 2.0 M PhLi (1.1 mmol) in THF. This reaction was allowed to stir at -78°C until completion byTLC (9:1 heptanes/ethyl acetate). The reaction was quenched with water and separated. The aqueous phase was extracted with diethyl ether three times, washed with brine and dried overMgSO4. The organic phase was concentrated and subjected to flash chromatography (9:1heptanes/ethyl acetate).

Reference： [1]Winters, Maria; DuHadaway, James B.; Pham, Khoa N.; Lewis-Ballester, Ariel; Badir, Shorouk; Wai, Jenny; Sheikh, Eesha; Yeh, Syun-Ru; Prendergast, George C.; Muller, Alexander J.; Malachowski, William P. [European Journal of Medicinal Chemistry, 2019, vol. 162, p. 455 - 464]

61
[ 100643-27-4 ]
[ 10203-08-4 ]
[ 126-81-8 ]
C₁₉H₁₈Cl₂N₄O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With MIL-100(Cr)/NHEtN(CH2PO3H2)2; In N,N-dimethyl-formamide; at 100℃; for 0.25h;	General procedure: In a 10 mL round-bottomed flask, a mixture of aldehyde (1 mmol),uracil derivatives (1 mmol), dimedone (1 mmol, 0.14 g) and MIL-100(Cr)/NHEtN(CH2PO3H2)2 (0.01 g) were stirred at 100 C in DMF(5 ml) as solvent. After completion of the reaction as monitored by TLC,the reaction mixture was cooled to room temperature. Then, the catalystwas separated from the solution of reaction mixture by centrifugation(1000 rpm). Then, H2O (5 ml) was added to reaction mixtureto give the solid sediment. The prepared solid was collected by simplefiltration. The crude product was purified by recrystallization fromEtOAc (Scheme 3). The pure products were identified by FT-IR, 1H, 13CNMR and mass spectra.

Reference： [1]Molecular catalysis,2020,vol. 481

62
[ 3470-49-3 ]
[ 10203-08-4 ]
(E)-2-(3,5-dichlorobenzylidene)-5-hydroxy-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium hydroxide; In methanol; at 20℃;	To a solution of 5-hydroxyindanone (Compound 1, 500.0 mg, 3.4 mmol) and 3,5- Dichlorobenz-aldehyde (650.0 mg, 3.7 mol) in MeOH (20 mL) was added iN NaOH (10 mL). The solution was stirred at RT for overnight. The reaction mixture was concentrated. The residue washed with H20 and Ether. The solid was further dried by pressing it on a filter paper to obtain the product as a powder. The product Compound 21c, (E)-2-(3,5- dichlorobenzylidene)-5 -hydroxy-2, 3 -dihydro- 1 H-inden- 1-one, was used without further purification (1.02 g, 98% yield).

Reference： [1]Patent: WO2019/51222,2019,A1 .Location in patent: Paragraph 00320; 00325; 00326; 00327

63
[ 10203-08-4 ]
[ 87189-16-0 ]
1,3-dichloro-5-(2,2-difluorovinyl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triphenylphosphine; In 1-methyl-pyrrolidin-2-one; at 100℃;Sealed tube; Inert atmosphere;	General procedure: An oven-dried 3-neck round-bottomed ask equipped with amagnetic stir bar was charged with aryl aldehyde (1.0 equiv.) andtriphenylphosphine (1.2 or 1.5 equiv.). The system was sealed withthree PFTE septa, and subsequently evacuated and backlled withN2 three times. Dry NMP was added via syringe transfer (PTFE sy-ringe with oven-dried stainless-steel needle), and the system wasimmersed in a preheated 100C oil bath. Once no solid reagentsremained (approximately 2 min of heating), potassium bromodi-uoroacetate (1.5 or 1.8 equiv.) was added portionwise over 0.5 h,with the rate of addition controlling the evolution of CO2 gas. Onceall of the potassium bromodiuoroacetate was added, the solutionwas allowed to stir for 0.5e1 h. Upon completion, the reaction wascooled to room temperature and then quenched with H2O. Subse-quently, Et2O was added to the reaction, and the mixture waswashed with H2O (ve times), and the aqueous layer was back-extracted with Et2O (two times). The combined organic layerswere dried over Na2SO4 and concentrated. The crude material wasdry-packed onto silica gel and then eluted through a plug of silicagel with EtOAc:hexanes (1:1) to remove triphenylphosphine oxide.Subsequently, H2O2 (30% in H2O) was added to the mother liquorand allowed to react for 30 min to oxidize the residual triphenyl-phosphine. The organic layer was washed with H2O (three times),dried over Na2SO4, concentrated, and subjected to normal phaseash chromatography using EtOAc and hexanes.

Reference： [1]Tetrahedron,2019,vol. 75,p. 4325 - 4336

64
[ 10203-08-4 ]
[ 67515-76-8 ]
methyl 5-(3.5-dichlorobenzylamino)pyridine-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With sodium tris(acetoxy)borohydride; trifluoroacetic acid; In 1,2-dichloro-ethane; at 20℃; for 16h;	3.5-dichlorobenzaldehyde (175 mg, 1 mmol),Methyl 5-amino-2-pyridinebenzoate (152 mg, 1 mmol)a solution of 1,2-dichloroethane was added to trifluoroacetic acid (0.1 ml).Sodium triacetoxyborohydride (1.48 g, 7 mmol) was added.The reaction was allowed to react at room temperature for 16 hours, and the reaction was terminated with an ammonium chloride solution.Extracted with ethyl acetate, dried over anhydrous sodiumColumn chromatography gave compound 31A (140 mg, yield 45%).

Reference： [1]Patent: CN104045552,2019,B .Location in patent: Paragraph 0364; 0365; 0366; 0367

65
[ 15317-58-5 ]
[ 10203-08-4 ]
C₁₆H₁₁Cl₂N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With propionic acid; In ethanol; for 2.5h;Reflux;	General procedure: 1H-Indole-3-carboxylate methylester 2 (1.0 mmol-equiv.) was refluxed with hydrazine hydrate(12.5 g, 0.25 M) in appropriate ethanol (30 mL) for 2 h. The progressof the reaction was monitored by TLC. After cooling the reactionmixture to room temperature, the mixtures were filtered to givewhite solid crude products without purification. Next, indolehydrazide(3, 1.0 mmol) in ethanol (30 mL) was added dropwiseinto the appropriate aldehyde (1.5 mmol-equiv.) and a few drops ofpropionic acid; the mixture was stirred and refluxed for 2.5 h. Aftercooling, the precipitates were filtered and washed several times bymethanol to yield the crystal substances 4aeu.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 180,p. 86 - 98

66
[ 15317-58-5 ]
[ 10203-08-4 ]
(E)-1-(4-chlorobenzyl)-N'-(3,5-dichlorobenzylidene)-1H-indole-3-carbohydrazide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 180,p. 86 - 98

67
[ 13679-73-7 ]
[ 10203-08-4 ]
(E)-3-(3,5-dichlorophenyl)-1-(4-methylthiophen-2-yl)prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydroxide; In methanol; water; at 69℃;pH 13 - 14;Cooling with ice; Microwave irradiation;	General procedure: Synthesis of chalcones 3e23. To a solution of appropriatelysubstituted ketone (1.01e7.93 mmol, 0.19e1.05 g) in methanol(25 mL) was added an aqueous solution of 40% sodium hydroxide(methanol/water) until pH 13e14, under stirring and on ice. Then, asolution of appropriately substituted benzaldehyde(2.03e15.86 mmol, 0.28e3.11 g) in methanol was slowly added tothe reaction mixture. The reaction was submitted to successive15 min periods of microwave irradiation of 180W of power, withthe final temperature of 69 C. Total irradiation time 2 he3 h, andwas monitored by TLC. Upon completion, the reaction mixture waspoured into ice and the pH was adjusted to approximately 7 withdiluted hydrochloride acid. For all chalcones, except 4, 10, 12, 19 and20 the resulting residue was filtered, washed with water, and purifiedas described below. For chalcones 4, 11, 12, 19 and 20 theresulting residue was taken in chloroform and further rinsed withwater, dried over anhydrous sodium sulfate, evaporated underreduced pressure and the obtained residue was purified asdescribed below.The structure elucidation of compounds 3e6, 8, 11, 12, and18e23 was established by 1H and 13C NMR techniques and datawere in accordance to the previously reported [51e62]. The structureelucidation of new compounds 7, 9e10, 13e17, and 24e27 wasestablished on basis of HRMS and NMR techniques.

Reference： [1]European Journal of Medicinal Chemistry,2019,vol. 184

68
[ 683-98-7 ]
[ 10203-08-4 ]
methyl 2-(2,6-dichloro-4-formylphenyl)-2,2-difluoroacetate [ No CAS ]
C₁₀H₆Cl₂F₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With fac-tris[2-phenylpyridinato-C²,N]iridium(III); potassium acetate In methanol at 20℃; for 18h; Inert atmosphere; Schlenk technique; Irradiation; Overall yield = 29 percent; Overall yield = 8.2 mg; regioselective reaction;

Reference： [1]Tang, Wei-Ke; Tang, Fei; Xu, Jun; Zhang, Qi; Dai, Jian-Jun; Feng, Yi-Si; Xu, Hua-Jian [Chemical Communications, 2020, vol. 56, # 10, p. 1497 - 1500]

69
[ 10203-08-4 ]
[ 6011-14-9 ]
2-(3,5-dichlorophenyl)aminoacetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%		10 mmol of 3,5-dichlorobenzaldehyde was added to 20 ml of an aqueous solution in which 20 mmol of potassium hydroxide and 10 mmol of aminoacetonitrile hydrochloride were dissolved, then 20 ml of ethanol was added and stirred for one hour. Then, 12 mmol of sodium borohydride was added, and the mixture was stirred overnight at room temperature. After adding hydrochloric acid, the reaction was adjusted to be acidic, extracted with ethyl acetate, the organic phase was separated, washed with saturated brine, separated the organic phase, dried over anhydrous sodium sulfate, and suspending the solvent to obtain the product. (80% yield, yellow solid).

Reference： [1]Patent: CN111057024,2020,A .Location in patent: Paragraph 0194-0197

70
[ 82261-42-5 ]
[ 10203-08-4 ]
N-[(3,5-dichlorophenyl)-methyl]-4-(3-pyridyl)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%	With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 18h;

Reference： [1]Han, Sang Hoon; Goins, Christopher M.; Arya, Tarun; Shin, Woo-Jin; Maw, Joshua; Hooper, Alice; Sonawane, Dhiraj P.; Porter, Matthew R.; Bannister, Breyanne E.; Crouch, Rachel D.; Lindsey, A. Abigail; Lakatos, Gabriella; Martinez, Steven R.; Alvarado, Joseph; Akers, Wendell S.; Wang, Nancy S.; Jung, Jae U.; MacDonald, Jonathan D.; Stauffer, Shaun R. [Journal of Medicinal Chemistry, 2022, vol. 65, # 4, p. 2880 - 2904]

71
[ 10203-08-4 ]
[ 614-16-4 ]
[ 6145-42-2 ]
4-(3,5-dichlorophenyl)-2-(methylamino)-6-phenylpyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2022,vol. 65,p. 2091 - 2106

72
[ 10203-08-4 ]
[ 21667-62-9 ]
[ 6145-42-2 ]
4-(3-chlorophenyl)-6-(3,5-dichlorophenyl)-2-(methylamino)pyrimidine-5-carbonitrile [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2022,vol. 65,p. 2091 - 2106

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Precautionary Statements-General
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Prevention
Code	Phrase
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P222	Do not allow contact with air.
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P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
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Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
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P320
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P321
P322
P330	Rinse mouth.
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P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
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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
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P401
P402	Store in a dry place.
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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
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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. 10203-08-4 ] {[proInfo.proName]}

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[ 10203-08-4 ] Synthesis Path-Upstream 1~15

[ 10203-08-4 ] Synthesis Path-Downstream 1~72

Related Functional Groups of [ 10203-08-4 ]

Aryls

Chlorides

Aldehydes

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[ 10203-08-4 ]