[ CAS No. 697-88-1 ] {[proInfo.proName]}

Name: 697-88-1|4-Bromo-2,6-dichloroaniline|97%
Brand: Ambeed
SKU: A321012
Price: 6.0 USD
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2D 3D

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Quality Control of [ 697-88-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 697-88-1 ]

SDS Specification

Alternatived Products of [ 697-88-1 ]

Product Details of [ 697-88-1 ]

CAS No. :	697-88-1	MDL No. :	MFCD00025162
Formula :	C₆H₄BrCl₂N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NPQBZKNXJZARBJ-UHFFFAOYSA-N
M.W :	240.91	Pubchem ID :	69680
Synonyms :

Calculated chemistry of [ 697-88-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	1.0
Molar Refractivity :	48.57
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.11 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.18
Log Po/w (XLOGP3) :	3.75
Log Po/w (WLOGP) :	3.35
Log Po/w (MLOGP) :	3.41
Log Po/w (SILICOS-IT) :	3.1
Consensus Log Po/w :	3.16

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.14
Solubility :	0.0174 mg/ml ; 0.0000724 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.99
Solubility :	0.0247 mg/ml ; 0.000103 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.13
Solubility :	0.0179 mg/ml ; 0.0000743 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.69

Safety of [ 697-88-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 697-88-1 ]

* 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 [ 697-88-1 ]
Downstream synthetic route of [ 697-88-1 ]

[ 697-88-1 ] Synthesis Path-Upstream 1~13

1
[ 697-88-1 ]
[ 99-30-9 ]

Reference： [1] Journal of the Chemical Society, 1907, vol. 91, p. 1553
[2] Journal of the Chemical Society, 1902, vol. 81, p. 494

2
[ 608-31-1 ]
[ 697-88-1 ]

Reference： [1] Synthetic Communications, 2000, vol. 30, # 20, p. 3669 - 3675
[2] Journal of Chemical Research, Synopses, 1997, # 11, p. 432 - 433
[3] Journal of the Chemical Society [Section] C: Organic, 1967, p. 400 - 404
[4] Tetrahedron, 2004, vol. 60, # 48, p. 10967 - 10972
[5] Journal of Chemical Research, 2004, # 10, p. 699 - 701
[6] Russian Journal of Applied Chemistry, 2011, vol. 84, # 10, p. 1748 - 1759

3
[ 106-40-1 ]
[ 697-88-1 ]

Reference： [1] Journal of the American Chemical Society, 2001, vol. 123, # 37, p. 9202 - 9203

4
[ 10468-46-9 ]
[ 697-88-1 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300[2] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 303

5
[ 103-88-8 ]
[ 697-88-1 ]

Reference： [1] Acta Crystallographica Section C: Crystal Structure Communications, 1998, vol. 54, # 12, p. 1974 - 1977

6
[ 13953-09-8 ]
[ 697-88-1 ]

Reference： [1] Acta Crystallographica Section C: Crystal Structure Communications, 1998, vol. 54, # 12, p. 1974 - 1977

7
[ 112160-74-4 ]
[ 106-40-1 ]
[ 697-88-1 ]

Reference： [1] Journal of the Chemical Society, 1907, vol. 91, p. 1553

8
[ 7647-01-0 ]
[ 10468-46-9 ]
[ 697-88-1 ]
[ 38762-41-3 ]
[ 106-40-1 ]
[ 1215-42-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300[2] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 303

9
[ 697-88-1 ]
[ 21928-51-8 ]

Reference： [1] Journal of Organometallic Chemistry, 1973, vol. 61, p. 207 - 218
[2] Tetrahedron, 2008, vol. 64, # 18, p. 4135 - 4142

10
[ 773837-37-9 ]
[ 697-88-1 ]
[ 99835-27-5 ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: With hydrogenchloride; sodium nitrite In water at 0℃; Stage #2: at 70℃; for 0.5 h;	Synthesis of compound 9.2. To a suspension of compound 9.1 (7.0 g, 29 mmol, 1.0 equiv), in water (35 mL) was added cone, hydrochloric acid (14 mL). The suspension was cooled to 0 °C then sodium nitrite (2.2 g, 31.96mmol, 1.1 equiv) in water (7mL) was added dropwise at 0 °C and the reaction mixture was stirred for 30 minutes. In another flask, a solution of copper (I) cyanide (3.11 g, 37.86mmol, 1.2 equiv) and sodium cyanide (2.13 g, 43.5mmol, 1.5 equiv) in water (35mL) was heated to 70°C. The diazonium salt mixture was neutralized by solid sodium bicarbonate and added portion wise to the cyanide mixture at 70°C. The mixture was heated at 70 °C for 30 minutes. Upon completion, the mixture was cooled to room temperature and extracted with toluene. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to obtain the crude material which was purified via flash column chromatography to furnish compound 9.2 (1.6g, 48percent).

Reference： [1] Patent: WO2015/131080, 2015, A1, . Location in patent: Paragraph 00315; 00316

11
[ 697-88-1 ]
[ 108-24-7 ]
[ 13953-09-8 ]

Reference： [1] Journal of Chemical Research, 2004, # 10, p. 699 - 701

12
[ 697-88-1 ]
[ 75-36-5 ]
[ 13953-09-8 ]

Reference： [1] Journal of the Chemical Society, 1907, vol. 91, p. 1553

13
[ 7647-01-0 ]
[ 10468-46-9 ]
[ 697-88-1 ]
[ 38762-41-3 ]
[ 106-40-1 ]
[ 1215-42-5 ]

Reference： [1] Justus Liebigs Annalen der Chemie, 1921, vol. 424, p. 300[2] Justus Liebigs Annalen der Chemie, 1925, vol. 441, p. 303

[ 697-88-1 ] Synthesis Path-Downstream 1~88

1
[ 697-88-1 ]
[ 99-30-9 ]

Reference： [1]Journal of the Chemical Society,1907,vol. 91,p. 1553

2
[ 697-88-1 ]
[ 71756-91-7 ]

Reference： [1]Journal of the Chemical Society,1907,vol. 91,p. 1553

3
[ 10468-46-9 ]
[ 697-88-1 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1921,vol. 424,p. 300
Justus Liebigs Annalen der Chemie,1925,vol. 441,p. 303

4
[ 697-88-1 ]
[ 21928-51-8 ]

Reference： [1]Journal of Organometallic Chemistry,1973,vol. 61,p. 207 - 218
[2]Tetrahedron,2008,vol. 64,p. 4135 - 4142

5
[ 697-88-1 ]
[ 62720-30-3 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1982,p. 1593 - 1598
[2]Tetrahedron,2004,vol. 60,p. 10967 - 10972

6
[ 697-88-1 ]
[ 4523-43-7 ]

Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 3454 - 3456

7
[ 608-31-1 ]
[ 697-88-1 ]

Yield	Reaction Conditions	Operation in experiment
93%	With tetrabutylammomium bromide; copper(ll) bromide; In ethanol; at 25℃;	General procedure: A round bottom flask was charged with Bu4NBr (2 mmol, 0.64 g), EtOH (8 mL) and 2-methylaniline (2 mmol, 0.21 g) followed by CuBr2 (3 mmol, 0.67 g). The resulted mixture was stirred at 25 C. After the completion of the reaction (monitored by TLC), the solvent was evaporated under reduced pressure. To the residue was added ammonium hydroxide (5 mL, 25% w/v) and water (5 mL) with stirring, and the suspension was extracted with DCM(10 mL×4) The organic phase was washed with saturated brine and dried over anhydrous Na2SO4. The product 2b was obtained using flash chromatograph column eluted with PE : EA (5 : 1).

Reference： [1]Synthetic Communications,2000,vol. 30,p. 3669 - 3675
[2]Synthetic Communications,2019,vol. 49,p. 1406 - 1415
[3]Journal of Chemical Research - Part S,1997,p. 432 - 433
[4]Journal of the Chemical Society C: Organic,1967,p. 400 - 404
[5]Tetrahedron,2004,vol. 60,p. 10967 - 10972
[6]Journal of Chemical Research,2004,p. 699 - 701
[7]Russian Journal of Applied Chemistry,2011,vol. 84,p. 1748 - 1759

8
[ 782482-64-8 ]
[ 697-88-1 ]
2-(4-bromo-2,6-dichloro-phenylazo)-2,3-dicyano-4-methyl-pentanoic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

9
[ 697-88-1 ]
[ 52685-35-5 ]
2-(4-bromo-2,6-dichloro-phenylazo)-2,3-dicyano-4,4-dimethyl-pentanoic acid ethyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

10
[ 697-88-1 ]
2-azido-5-bromo-1,3-dichloro-benzene [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

11
[ 24424-99-5 ]
[ 697-88-1 ]
[ 915145-00-5 ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 4398 - 4404

12
[ 697-88-1 ]
[ 915145-01-6 ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 4398 - 4404

13
[ 697-88-1 ]
4-(tert-butoxycarboxamido)-3,5-dichlorobenzoic acid [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2006,p. 4398 - 4404

14
[ 697-88-1 ]
[ 879012-78-9 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

15
[ 697-88-1 ]
[ 879012-77-8 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

16
[ 697-88-1 ]
4-butyl-1-(2,6-dichloro-4-ethynyl-phenyl)-1H-[1,2,3]triazole [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

17
[ 697-88-1 ]
5-butyl-1-(2,6-dichloro-4-ethynyl-phenyl)-1H-[1,2,3]triazole [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

18
[ 697-88-1 ]
5-butyl-1-(2,6-dichloro-4-trimethylsilanylethynyl-phenyl)-1H-[1,2,3]triazole [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

19
[ 697-88-1 ]
4-butyl-1-(2,6-dichloro-4-trimethylsilanylethynyl-phenyl)-1H-[1,2,3]triazole [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

20
[ 697-88-1 ]
5-[4-(4-butyl-[1,2,3]triazol-1-yl)-3,5-dichloro-phenyl]-pent-4-ynoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

21
[ 697-88-1 ]
5-[4-(5-butyl-[1,2,3]triazol-1-yl)-3,5-dichloro-phenyl]-pent-4-ynoic acid methyl ester [ No CAS ]

Reference： [1]Journal of Agricultural and Food Chemistry,2006,vol. 54,p. 1361 - 1372

22
[ 697-88-1 ]
[ 724764-88-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

23
[ 697-88-1 ]
[ 724764-89-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

24
[ 697-88-1 ]
5-amino-1-(2,6-dichloro-4-ethynyl-phenyl)-4-isopropyl-1H-pyrazole-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

25
[ 697-88-1 ]
5-amino-4-tert-butyl-1-(2,6-dichloro-4-ethynyl-phenyl)-1H-pyrazole-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

26
[ 697-88-1 ]
5-amino-1-(2,6-dichloro-4-trimethylsilanylethynyl-phenyl)-4-isopropyl-1H-pyrazole-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

27
[ 697-88-1 ]
5-amino-4-tert-butyl-1-(2,6-dichloro-4-trimethylsilanylethynyl-phenyl)-1H-pyrazole-3-carbonitrile [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 3345 - 3355

28
[ 697-88-1 ]
[ 38444-88-1 ]

Reference： [1]Chemosphere,2001,vol. 45,p. 137 - 143

29
[ 697-88-1 ]
[ 70362-50-4 ]

Reference： [1]Chemosphere,2001,vol. 45,p. 137 - 143

30
[ 697-88-1 ]
5-chloro-N-cyclopropylmethyl-N'-(2,6-dichloro-phenyl)-2-methyl-N-propyl-pyrimidine-4,6-diamine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 331 - 333

31
[ 697-88-1 ]
[ 336194-96-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 331 - 333

32
[ 697-88-1 ]
[ 336194-90-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2001,vol. 11,p. 331 - 333

33
[ 103-88-8 ]
[ 697-88-1 ]

Reference： [1]Acta Crystallographica, Section C: Crystal Structure Communications,1998,vol. 54,p. 1974 - 1977

34
[ 697-88-1 ]
acetic acid-(4-bromo-2,6,N-trichloro-anilide) [ No CAS ]

Reference： [1]Journal of the Chemical Society,1907,vol. 91,p. 1553

35
[ 697-88-1 ]
benzoic acid-(4-bromo-2,6,N-trichloro-anilide) [ No CAS ]

Reference： [1]Journal of the Chemical Society,1904,vol. 85,p. 182

36
[ 697-88-1 ]
[ 51693-89-1 ]

Reference： [1]Journal of Organometallic Chemistry,1973,vol. 61,p. 207 - 218

37
[ 697-88-1 ]
2-(3,4,5-Trichlorphenyl)propan-2-ol [ No CAS ]

Reference： [1]Journal of Organometallic Chemistry,1973,vol. 61,p. 207 - 218

38
[ 344744-11-2 ]
[ 697-88-1 ]
4'-bromo-2',6'-dichloro-2,4-bis-trifluoromethyl-1,3-thiazole-5-carboxanilide [ No CAS ]

Reference： [1]Patent: US6372769,2002,B1 .Location in patent: Page column 5

39
[ 697-88-1 ]
[ 79-06-1 ]
C₉H₈Cl₂N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With triethylamine; tris-(o-tolyl)phosphine;palladium diacetate; In acetonitrile; at 70℃;	Pd (OAc) 2 (186 mg), P (o-Tol) 3 (505 mg), Et3N (1.73 ml), 4-bromo-2,6- dichlorobenzeneamine (2.0 g) and acrylamide (885 mg) were dissolved in MECN (15 ml) and N2 was bubbled through the reaction mixture for at least 20 minutes. Then a cooler was mounted strictly under nitrogen atmosphere. The reaction mixture was heated at 70 C overnight. The reaction mixture was allowed to cool to 20 C and was diluted with CH2CI2 and washed with saturated aqueous NAHC03 (2x) and dried with brine and NA2SO4. The residue was sonicated in diisopropyl ether and filtered off. Yield: 0.55 g of intermediate 18 (30%).

Reference： [1]Patent: WO2004/74266,2004,A1 .Location in patent: Page 49-50

40
[ 1122-99-2 ]
[ 697-88-1 ]
N-(4-bromo-2,6-dichloro-phenyl)-2-cyclopentyl-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With sodium carbonate; In tetrahydrofuran; for 6h;Heating / reflux;	N-(4-Bromo-2,6-dichloro-phenyl)-2-cyclopentyl-acetamide.; 4-Bromo-2,6-dichloroaniline (12.1 g) and cyclopentylacetyl chloride (8.1 g) were dissolved in tetrahydrofuran (100 mL) and sodiumcarbonate (6.4 g) is added, followed by heating to reflux for 6 hours. The reaction mixture was cooled to ambient temperature and filtered and diluted with water (250 ml). After extraction, the combined organic phase was concentrated in vacuo to furnish 14.0 g (80% yield) of the title compound as a white solid. LC-MS (m/z) 352 (MH+); tR = 3.47, (UV, ELSD) 96%, 99%. 1H NMR (500 MHz, DMSOd6): 1.12 (m, 2H), 1.50 (m, 4H)5 1.80 (m, 2H), 2.15 (m, IH), 2.50 (d, 2H), 5.70 (broad s, IH), 7.45 (s, 2H).

Reference： [1]Patent: WO2006/29623,2006,A1 .Location in patent: Page/Page column 54

41
[ 697-88-1 ]
[ 814-68-6 ]
[ 797793-00-1 ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; at 20℃;	REFERENCE EXAMPLE 1 N-(4-bromo-2,6-dichlorophenyl)acrylamide A solution of <strong>[697-88-1](4-bromo-2,6-dichlorophenyl)amine</strong> (4 g) and acryloyl chloride (1.4 mL) in dichloromethane (10 mL) was stirred overnight at room temperature. To the solution were added water and ethyl acetate at 0 degree. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, subsequently, dried over an anhydrous magnesium sulfate and then concentrated. The residue was washed with diisopropylether to give the title compound (1.96 g) having the following physical data. TLC: Rf 0.25 (hexane:ethyl acetate=5:1); NMR(CDCl3): delta 7.55 (s, 2H), 7.11 (br, 1H), 6.51-6.44 (m, 1H), 6.40-6.20 (m, 1H), 5.85 (d, J=10.5 Hz, 1H).

Reference： [1]Patent: US2007/10529,2007,A1 .Location in patent: Page/Page column 23

42
[ 697-88-1 ]
dichloro(1,1'-dimethylsilylenebis{2-ethyl-4-(4-trimethylsilyl-3,5-dichlorophenyl)-4H-azulenyl})hafnium [ No CAS ]
[ 62720-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium iodide; sulfuric acid; sodium thiosulfate; sodium nitrite; In ice-water;	(a) Synthesis of dichloro(1,1'-dimethylsilylenebis{2-ethyl-4-(4-trimethylsilyl-3,5-dichlorophenyl)-4H-azulenyl})hafnium 2,6-Dichloro-4-bromoaniline (15.6 g, 64.8 mmol) was gradually added to concentrated sulfuric acid (40 ml). The mixture was then stirred at room temperature for 20 minutes. The mixture was then cooled to 0 C. To the mixture was then added gradually sodium nitrite (4.9 g, 71.22 mmol). The mixture was then stirred at a temperature of 0 C. to 5 C. for 2.5 hours. The mixture thus obtained was then added to ice-water (200 g). To the mixture was then added an aqueous solution of potassium iodide (12.9 g, 77.76 mmol) at 5 C. The mixture was then allowed to stand at 5 C. for 15 minutes and at room temperature for 1 hour. The mixture was then extracted with diethyl ether. The extract was washed with an aqueous solution of sodium thiosulfate, and then dried over magnesium sulfate. The solvent was then distilled off. The crude product thus obtained was then extracted with hexane (200 ml). The solvent was then distilled off. As a result, a crude product was obtained in an amount of 18.62 g. The crude product was then recrystallized from ethanol (75 ml). As a result, 2,6-dichloro-4-bromoiodobenzene was obtained (14.8 g; yield: 65%). 1H NMR (400 MHz, CDCl3) delta7.51 (s, 2H).

Reference： [1]Patent: US2005/70426,2005,A1

43
[ 697-88-1 ]
[ 292638-85-8 ]
[ 1110767-73-1 ]

Yield	Reaction Conditions	Operation in experiment
		4-Bromo-2,6-dichloroaniline (5, 80 g) was dissolved in acetone (640 mL), and a 48% hydrogen bromide aqueous solution (120 mL) was added, followed by stirring at 0C. A sodium nitrite (32 g) aqueous solution (160 mL) was added dropwise thereto, the mixture was stirred for 30 minutes, and methyl acrylate (200 mL), and water (200 mL) were added, followed by stirring for 1 hour. At room temperature, cuprous oxide (2 g) was added, followed by stirring for 2 hours. The reaction solution was extracted with ethyl acetate, and purified by column chromatography to obtain methyl (E)-3-(4-bromo-2,6-dichlorophenyl)acrylate (48.5 g). Methyl (E)-3-(4-bromo-2,6-dichlorophenyl)acrylate (48.5 g) was dissolved in dichloromethane, an ozone gas was introduced at -70C, and ozone oxidization was performed. To the reaction solution was added dimethyl sulfide (40 mL), and this was extracted with ethyl acetate to obtain 4-bromo-2,6-dichlorobenzaldehyde (6, 37.2 g). NMR (CDCl3) delta ppm: 10.42 (s, 1H), 7.58 (s, 2H)

Reference： [1]Patent: EP2184279,2010,A1 .Location in patent: Page/Page column 19-20

44
[ 697-88-1 ]
[ 536-74-3 ]
[ 1217485-98-7 ]

Reference： [1]Journal of Polymer Science, Part A: Polymer Chemistry,2010,vol. 48,p. 861 - 868

45
[ 2304-94-1 ]
[ 697-88-1 ]
[ 797793-05-6 ]

Yield	Reaction Conditions	Operation in experiment
		REFERENCE EXAMPLE 5 benzyl {3-[(4-bromo-2,6-dichlorophenyl)amino]-3-oxopropyl}carbamate To N-[(benzyloxy)carbonyl]-beta-alanine (2 g) was added thionyl chloride (2 mL). The mixture was stirred for 30 minutes at room temperature and then concentrated. To the residue was added <strong>[697-88-1](4-bromo-2,6-dichlorophenyl)amine</strong> (2 g) and the mixture was stirred for 5 minutes at room temperature. To the reaction mixture was added dichloromethane (10 mL) and the mixture was stirred for 1 hour at room temperature. To the mixture were added water and ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride, subsequently, dried over an anhydrous magnesium sulfate and then concentrated to give the title compound (2.1 g) having the following physical data. TLC: Rf 0.35 (hexane:ethyl acetate=1:1); NMR(CDCl3): delta 7.54 (s, 2H), 7.38-7.30 (m, 5H), 7.15 (br, 1H), 5.35 (br, 1H), 5.10 (s, 2H), 3.62-3.55 (m, 2H), 2.75-2.65 (m, 2H).

Reference： [1]Patent: US2007/10529,2007,A1 .Location in patent: Page/Page column 26

46
[ 697-88-1 ]
[ 407-25-0 ]
C₈H₃BrCl₂F₃NO [ No CAS ]

Reference： [1]Russian Journal of Applied Chemistry,2011,vol. 84,p. 1748 - 1759

47
[ 697-88-1 ]
[ 1378039-78-1 ]
[ 1378040-74-4 ]

Reference： [1]Patent: WO2012/66061,2012,A1 .Location in patent: Page/Page column 224-225

48
[ 697-88-1 ]
[ 73183-34-3 ]
[ 1371630-51-1 ]

Yield	Reaction Conditions	Operation in experiment
39.3%	With sodium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In dimethyl sulfoxide; at 80℃; for 16h;Inert atmosphere;	A solution of <strong>[697-88-1]4-bromo-2,6-dichloroaniline</strong> (1 g, 4.15 mmol) in dimethyl sulfoxide (10 mL) (0.4 M) was added to sodium acetate (1 .022 g, 12.45 mmol) and bis-pinacolato diborane (1 .159 g,4.57 mmol) in a flask under argon. The mixture was degassed with argon. 1 ,1 '-Bis- diphenylphosphine ferrocene palladium(ll) dichloride (0.328 g, 0.415 mmol) was added and the reaction mixture was heated at 802C for 16h. After cooling to room temperature ethyl acetate (50 mL) was added and the reaction mixture was filtered and partitioned between ethyl acetate and a saturated aqueous sodium bicarbonate solution (50 mL). The organic layer was washed with brine (4 X 50 mL), dried sodium sulfate and concentrated in vacuum. The crude product was purified by flash silica column chromatography (heptane/5% ethyl acetate) to give a white solid (470 mg, 39.3%).1 H NMR (400 MHz, CDCI3) delta ppm 7.60 (s, 2 H), 4.67 (s, 2 H), 1 .32 (s, 12 H).

Reference： [1]Patent: WO2012/104305,2012,A1 .Location in patent: Page/Page column 114; 115

49
[ 697-88-1 ]
[ 1371629-38-7 ]

Reference： [1]Patent: WO2012/104305,2012,A1

50
[ 697-88-1 ]
[ 1371630-27-1 ]

Reference： [1]Patent: WO2012/104305,2012,A1

51
[ 108-22-5 ]
[ 697-88-1 ]
[ 1452177-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) oxide; tert.-butylnitrite; In acetonitrile; at 20 - 40℃; for 20h;	Example P2: Preparation of 1-(4-bromo-2,6-dichloro-phenyl)-propan-2-one: In a 50ml three-neck flask equipped with mechanical stirring, cooling funnel, dropping funnel and thermometer under nitrogen at ambient temperature filled with acetonitrile (10 ml), were added cuprous oxide (1.5 g, 0.018 mol), isopropenyl acetate (13.6 ml, 0.125 mol) and tert-butyl nitrite (1.7 ml, 0.0125 mol). The resulting red suspension is stirred for 15min at ambient temperature. A solution of <strong>[697-88-1]4-bromo-2,6-dichloroaniline</strong> (2.0 g, 0.0083 mol), dissolved in acetonitrile (15 ml) was added dropwise over a period of 20 minutes. During the addition, bubbling was observed. The mixture was stirred at 40C for 20 hours. The red crude mixture was passed through celite to remove solid particles and concentrated under reduce pressure to give a brown solid. The residue was dissolved in dichloromethane (120 ml) and washed with water (2 x 50 ml) and brine (40 ml). Organics were dried over sodium sulfate and concentrated under reduced pressure to give crude 1-(4-bromo-2,6-dichloro- phenyl)-propan-2-one (2.3g) as a dark brown oil. 1 H NMR (400MHz, CDCI3): delta 2.25 (s,3H,CH3 ), 4.06(s,2H,CH2), 7.50 (s,2H, Ar-H)
	With copper(I) oxide; tert.-butylnitrite; In acetonitrile; at 20 - 40℃; for 20h;Inert atmosphere;	Example P2: Preparation of 1 -(4-bromo-2,6-dichloro-phenyl)-propan-2-one: In a 50ml three-neck flask equipped with mechanical stirring, cooling funnel, dropping funnel and thermometer under nitrogen at ambient temperature filled with acetonitrile (10 ml), were added cuprous oxide (1 .5 g, 0.018 mol), isopropenyl acetate (13.6 ml, 0.125 mol) and tert-butyl nitrite (1 .7 ml, 0.0125 mol). The resulting red suspension is stirred for 15min at ambient temperature. A solution of <strong>[697-88-1]4-bromo-2,6-dichloroaniline</strong> (2.0 g, 0.0083 mol), dissolved in acetonitrile (15 ml) was added dropwise over a period of 20 minutes. During the addition, bubbling was observed. The mixture was stirred at 40C for 20 hours. The red crude mixture was passed through celite to remove solid particles and concentrated under reduce pressure to give a brown solid. The residue was dissolved in dichloromethane (120 ml) and washed with water (2 x 50 ml) and brine (40 ml). Organics were dried over sodium sulfate and concentrated under reduced pressure to give crude 1 -(4-bromo-2,6-dichloro- phenyl)-propan-2-one (2.3g) as a dark brown oil. 1H NMR (400MHz, CDCI3): delta 2.25 (s,3H,CH3 ), 4.06(s,2H,CH2), 7.50 (s,2H, Ar-H)
		In a 50 ml three-neck flask equipped with mechanical stirring, cooling funnel, dropping funnel and thermometer under nitrogen at ambient temperature filled with acetonitrile (10 ml), were added cuprous oxide (1.5 g, 0.018 mol), isopropenyl acetate (13.6 ml, 0.125 mol) and tert-butyl nitrite (1.7 ml, 0.0125 mol). The resulting red suspension is stirred for 15 min at ambient temperature. A solution of <strong>[697-88-1]4-bromo-2,6-dichloroaniline</strong> (2.0 g, 0.0083 mol), dissolved in acetonitrile (15 ml) was added dropwise over a period of 20 minutes. During the addition, bubbling was observed. The mixture was stirred at 40 C. for 20 hours. The red crude mixture was passed through celite to remove solid particles and concentrated under reduce pressure to give a brown solid. The residue was dissolved in dichloromethane (120 ml) and washed with water (2*50 ml) and brine (40 ml). Organics were dried over sodium sulfate and concentrated under reduced pressure to give crude 1-(4-bromo-2,6-dichloro-phenyl)-propan-2-one (2.3g) as a dark brown oil. 1H NMR (400 MHz, CDCl3): delta 2.25 (s,3H,CH3), 4.06(s,2H,CH2), 7.50 (s,2H, Ar-H)

Reference： [1]Patent: WO2013/127441,2013,A1 .Location in patent: Page/Page column 6-7
[2]Patent: WO2013/127764,2013,A1 .Location in patent: Page/Page column 8-9
[3]Patent: US2015/31919,2015,A1 .Location in patent: Paragraph 0043; 0044; 0045

52
[ 1897-45-6 ]
[ 697-88-1 ]
[ 1416419-83-4 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2013,vol. 61,p. 11929 - 11936

53
[ 697-88-1 ]
[ 766-97-2 ]
[ 1593268-09-7 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2216 - 2219
[2]Organic Letters,2015,vol. 17,p. 2566 - 2566

54
[ 697-88-1 ]
[ 766-97-2 ]
[ 1593268-10-0 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2216 - 2219
[2]Organic Letters,2015,vol. 17,p. 2566 - 2566

55
[ 697-88-1 ]
[ 82102-37-2 ]
[ 766-97-2 ]
[ 1593267-97-0 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2216 - 2219

56
[ 1072315-89-9 ]
[ 697-88-1 ]
[ 766-97-2 ]
[ 1593268-08-6 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2216 - 2219

57
[ 697-88-1 ]
[ 82102-37-2 ]
[ 95-55-6 ]
4-(benzoxazol-2-yl)-2,6-dichloroaniline [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2094 - 2097

58
[ 2631-77-8 ]
[ 697-88-1 ]
2-((4-bromo-2,6-dichlorophenylimino)methyl)-4,6-diiodophenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%	With acetic acid; In ethanol;Reflux;	Schiff base ligand were synthesized by refluxing of 3,5 diiodosalicylaldehyde (0.01M) and <strong>[697-88-1]4-bromo-2,6-dichlorobenzenamine</strong> (0.01 M) in 50ml ethanol on water bath for 4-5 hours inpresence of 2-3 drops of glacial acetic acid. The reaction mixture was kept for overnight, where yellow color precipitate was obtained. It was filtered by whatmann paper, washed with distilled water then alcohol, dried in vacuum dessicator. Pure Schiff base was recrystallized from ethanol. The purity ofligand was checked by TLC.

Reference： [1]Oriental Journal of Chemistry,2014,vol. 30,p. 2049 - 2058

59
[ 697-88-1 ]
[Tb(2-[(4-bromo-2,6-dichlorophenylimino)methyl]-4,6-diiodophenol)₂2H₂O]Cl [ No CAS ]

Reference： [1]Oriental Journal of Chemistry,2014,vol. 30,p. 2049 - 2058

60
[ 697-88-1 ]
[La(2-[(4-bromo-2,6-dichlorophenylimino)methyl]-4,6-diiodophenol)₂2H₂O]Cl [ No CAS ]

Reference： [1]Oriental Journal of Chemistry,2014,vol. 30,p. 2049 - 2058

61
[ 697-88-1 ]
[Pr(2-[(4-bromo-2,6-dichlorophenylimino)methyl]-4,6-diiodophenol)₂2H₂O]Cl [ No CAS ]

Reference： [1]Oriental Journal of Chemistry,2014,vol. 30,p. 2049 - 2058

62
[ 697-88-1 ]
[Nd(2-[(4-bromo-2,6-dichlorophenylimino)methyl]-4,6-diiodophenol)2H₂O₂Cl] [ No CAS ]

Reference： [1]Oriental Journal of Chemistry,2014,vol. 30,p. 2049 - 2058

63
[ 201230-82-2 ]
[ 697-88-1 ]
[ 766-97-2 ]
[ 1593267-97-0 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2566 - 2566
[2]Organic Letters,2019,vol. 21,p. 5775 - 5778

64
[ 697-88-1 ]
[ 1641-69-6 ]
[ 766-97-2 ]
[ 1593268-08-6 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2566 - 2566

65
[ 697-88-1 ]
2-(4-((2-(2,6-dichloro-4-cyanophenyl)-5-oxo-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)amino)phenyl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

66
[ 697-88-1 ]
C₇H₅BrCl₂N₂ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

67
[ 697-88-1 ]
C₁₄H₁₃BrCl₂N₂O₃ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

68
[ 697-88-1 ]
C₁₄H₁₁BrCl₂N₂O₃ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

69
[ 697-88-1 ]
C₁₄H₁₀BrCl₃N₂O₂ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

70
[ 697-88-1 ]
C₂₆H₂₆BrCl₂N₃O₄ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

71
[ 697-88-1 ]
C₂₇H₂₆Cl₂N₄O₄ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

72
[ 697-88-1 ]
C₂₇H₂₄Cl₂N₄O₅ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

73
[ 697-88-1 ]
C₃₄H₃₁Cl₂N₅O₅ [ No CAS ]

Reference： [1]Patent: WO2015/131080,2015,A1

74
[ 1116-98-9 ]
[ 697-88-1 ]
[ 82102-37-2 ]
[ 1395052-09-1 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 1358 - 1366

75
[ 697-88-1 ]
[ 98-80-6 ]
[ 134006-32-9 ]