[ CAS No. 54932-72-8 ] {[proInfo.proName]}

Name: 54932-72-8|4-Bromo-1-chloro-2-methylbenzene|98%
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SKU: A237569
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2D 3D

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Quality Control of [ 54932-72-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 54932-72-8 ]

Product Details of [ 54932-72-8 ]

CAS No. :	54932-72-8	MDL No. :	MFCD00018503
Formula :	C₇H₆BrCl	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OZFQMHJKAODEON-UHFFFAOYSA-N
M.W :	205.48	Pubchem ID :	609899
Synonyms :

Calculated chemistry of [ 54932-72-8 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.12
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
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) :	-4.69 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.46
Log Po/w (XLOGP3) :	4.03
Log Po/w (WLOGP) :	3.41
Log Po/w (MLOGP) :	3.95
Log Po/w (SILICOS-IT) :	3.62
Consensus Log Po/w :	3.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.15
Solubility :	0.0147 mg/ml ; 0.0000714 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.73
Solubility :	0.038 mg/ml ; 0.000185 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.26
Solubility :	0.0113 mg/ml ; 0.0000552 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.43

Safety of [ 54932-72-8 ]

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

Application In Synthesis of [ 54932-72-8 ]

* 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 [ 54932-72-8 ]
Downstream synthetic route of [ 54932-72-8 ]

[ 54932-72-8 ] Synthesis Path-Upstream 1~15

1
[ 54932-72-8 ]
[ 4387-31-9 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647

2
[ 54932-72-8 ]
[ 21900-52-7 ]

Reference： [1] Journal of the Chemical Society, 1904, vol. 85, p. 1269

3
[ 54932-72-8 ]
[ 21739-92-4 ]

Reference： [1] Journal of Organic Chemistry, 1957, vol. 22, p. 1096
[2] Journal of the Chemical Society, 1904, vol. 85, p. 1269

4
[ 54932-72-8 ]
[ 68-12-2 ]
[ 101349-71-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1997, vol. 40, # 11, p. 1634 - 1647

5
[ 95-49-8 ]
[ 89794-02-5 ]
[ 54932-72-8 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1063 - 1066

6
[ 583-75-5 ]
[ 54932-72-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogenchloride; copper(l) chloride; sodium nitrite In 1,4-dioxane; water at -5 - 80℃; for 3.5 h;	11.7 g (63.2 mmol) of 4-bromo-2-methylaniline was added to 45 ml (6 mol / L) hydrochloric acid solution and stirred well to make the salt.The resulting solution was placed in an ice-salt bath, cooled to below -5 ° C, and about 20percent sodium nitrite solution (4.8 g, 69.5 mmol, 20 ml) was slowly added dropwise to maintain the temperature below 0 ° C.Drop, add 12ml of 1,4-dioxane, stir well.The above diazonium salt solution was slowly added to a 3 mol / L hydrochloric acid solution (20 ml) of cuprous chloride (6.7 g, 66.4 mmol) in an ice-water bath and stirred vigorously. After completion of the dropwise addition, the mixture was stirred at room temperature for 0.5 h, To 80 ° C for 3 h.Cooled, extracted with dichloromethane (75 ml * 2) and the extract was saturated with NaHCO₃(150 ml), water (150 ml) and saturated brine (100 ml * 2), dried over anhydrous sodium sulfate overnight and concentrated under reduced pressure to give 11.2 g (yield 87percent) of reddish brown liquid.
87%	Stage #1: With hydrogenchloride; sodium nitrite In water at -5 - 0℃; for 3 h; Large scale Stage #2: With copper(l) chloride In water at 60℃; for 3 h; Large scale	Take 4-bromo-2-methylaniline 184kg, dissolved in 600kg concentrated hydrochloric acid, cooled to -5°C in an ice bath, and add sodium nitrite dropwise.Aqueous solution (sodium nitrite 68kg + ice water 200kg), 1h drip, control temperature does not exceed 0 °C in the dropping process, after the completion of the dropping, the reaction below -5 °C 2h, after the reaction is completed,In the reaction system, 120 kg of cuprous chloride was added, and the system was slowly heated to 60 degrees for 3 hours. After the reaction was completed, 400 kg of ethyl acetate was added to the system for extraction, washed with water until neutral, dried over anhydrous sodium sulfate, and the ethyl acetate was recovered under reduced pressure. Distillation under reduced pressure gave a yellow liquid, 176 kg, with a yield of 87percent.

Reference： [1] Patent: CN104478670, 2016, B, . Location in patent: Paragraph 0027-0028
[2] Patent: CN107652276, 2018, A, . Location in patent: Paragraph 0015; 0017

7
[ 95-49-8 ]
[ 89794-02-5 ]
[ 54932-72-8 ]

Reference： [1] Tetrahedron Letters, 2013, vol. 54, # 9, p. 1063 - 1066

8
[ 95-53-4 ]
[ 54932-72-8 ]

Reference： [1] Patent: CN104478670, 2016, B,
[2] Patent: CN107652276, 2018, A,

9
[ 95-49-8 ]
[ 54932-72-8 ]

Reference： [1] Journal of the Indian Chemical Society, 1934, vol. 11, p. 293
[2] Journal of the Chemical Society, 1914, vol. 105, p. 1910
[3] Journal of the Indian Chemical Society, 1934, vol. 11, p. 293

10
[ 591-17-3 ]
[ 54932-72-8 ]

Reference： [1] Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical and Analytical Chemistry, 1993, vol. 32, # 8, p. 717 - 720

11
[ 24106-05-6 ]
[ 54932-72-8 ]

Reference： [1] Journal of the Indian Chemical Society, 1959, vol. 36, p. 329,333

12
[ 99-52-5 ]
[ 54932-72-8 ]

Reference： [1] Journal of the Chemical Society, 1904, vol. 85, p. 1269

13
[ 95-49-8 ]
[ 7664-93-9 ]
[ 7726-95-6 ]
[ 64-19-7 ]
[ 54932-72-8 ]

Reference： [1] Journal of the Indian Chemical Society, 1934, vol. 11, p. 293

14
[ 95-49-8 ]
[ 7726-95-6 ]
[ 7697-37-2 ]
[ 64-19-7 ]
[ 54932-72-8 ]

Reference： [1] Journal of the Indian Chemical Society, 1934, vol. 11, p. 293

15
[ 54932-72-8 ]
[ 915095-89-5 ]

Reference： [1] Patent: CN107652276, 2018, A,

[ 54932-72-8 ] Synthesis Path-Downstream 1~88

1
[ 95-49-8 ]
[ 54932-72-8 ]

Reference： [1]Journal of the Indian Chemical Society,1934,vol. 11,p. 293
[2]Journal of the Chemical Society,1914,vol. 105,p. 1910
[3]Journal of the Indian Chemical Society,1934,vol. 11,p. 293

2
[ 24106-05-6 ]
[ 54932-72-8 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 329,333

3
[ 54932-72-8 ]
[ 84388-50-1 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 329,333

4
[ 54932-72-8 ]
[ 21739-92-4 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 1096
[2]Journal of the Chemical Society,1904,vol. 85,p. 1269

5
[ 591-17-3 ]
[ 54932-72-8 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1993,vol. 32,p. 717 - 720

6
[ 54932-72-8 ]
[ 68-12-2 ]
[ 101349-71-7 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

7
[ 54932-72-8 ]
[ 149965-41-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With N-Bromosuccinimide; dibenzoyl peroxide; In acetonitrile; at 90℃;	To a solution of 4-bromo-1 -chloro-2-methyl-benzene (30 g, 146 mmol) and benzoyl peroxide (0.71 g, 3 mmol) in acetonitrile (70 mL) was added N-bromosuccinimide (28.6 g, 161 mmol) at 90C and the mixture was stirred overnight. The solution was evaporated under reduced pressure and the crude material was purified onsilica gel to give 4-bromo-2-(bromomethyl)-1 - chloro-benzene as a white solid (40.3 g, 95% yield).
92%	With N-Bromosuccinimide; dibenzoyl peroxide; In chloroform; at 70℃; for 4h;Large scale;	Take <strong>[54932-72-8]4-bromo-2-methylchlorobenzene</strong> 100kg, dissolved in 300kg of chloroform, add 90kg of NBS, add BPO 6kg, heat up to 70 C reflux reaction 4h, after the reaction is completed, cooled to room temperature, filtered, the filtrate decompression recovery of chloroform, petroleum Ethyl ether: Ethyl acetate (1:1) was recrystallized to give 128 kg of a white solid with a yield of 92%.
72%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In chloroform; for 5h;Reflux;	A solution of 4.1 g (20 mmol) of <strong>[54932-72-8]5-bromo-2-chlorotoluene</strong>, 0.66 g (4 mmol) of 2,2-azobisisobutyronitrile, 3.9 g (22 mmol) of N-bromosuccinimide and 20 ml of chloroform Dry two bottles, reflux 5h.(100 ml), dried over anhydrous sodium sulfate, filtered, concentrated under reduced pressure, and the residue was recrystallized from ethanol to give 4.1 g of needle-like crystals (100 ml), washed with water (100 ml) (Yield 72%).

~ 65%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 2h;Heating / reflux;	N-bromosuccinimide (1.1 equiv.) and benzoylperoxide (0.002 equiv.) were added to a sol. of <strong>[54932-72-8]2-chloro-5-bromotoluene</strong> in CCl4 (5 mL/mmol) and the mixture refluxed for 2 h. After complete conversion (thin-film chromatography), the reaction mixture was cooled, filtered and washed with chloroform. The organic phase was evaporated to low bulk in a vacuum and the raw product purified by column chromatography (5% EE in hexane) (yield approx. 65%).
31.3%	With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane; for 5h;Reflux;	Reference Example 27 [Step a] To a solution of compound 1 (2.00 g, 9.80 mmol) in carbon tetrachloride (50.0 mL) were added N-bromosuccinimide (1.92 g, 10.7 mmol) and benzoyl peroxide (24.0 mg, 99.1 mumol) at room temperature, and the mixture was stirred with heating under reflux for 5 hr. The reaction solution was filtered through celite, and the obtained filtrate was concentrated and the residue was purified by silica gel chromatography to give compound 2 (867 mg, 31.3%). 1H-NMR (400 MHz, CDCl3)delta: 4.52(2H, s), 7.26(1H, d, J=8.7Hz), 7.38(1H, dd, J=8.7, 2.6Hz), 7.58(1H, d, J=2.6Hz).
	With N-Bromosuccinimide;dibenzoyl peroxide; In tetrachloromethane; for 4h;Reflux;	A mixture of 4-bromo-l-chloro-2-methylbenzene (5.Og, 24.0 mmol), N- bromosuccinimide (4.4 g, 25.0 mmol), and benzoyl peroxide (700 mg, 2.9 mmol) in anhydrous carbon tetrachloride (85 mL) was stirred at reflux for 4 hours. Dichloromethane (50 mL) was added. The mixture was extracted with 1 N NaOH (1 x 150 mL) and brine (1 x 150 mL). The organic extract was recovered, dried over MgSO4, filtered, evaporated, and dried in vacuo. The crude product was purified by flash chromatography (0-5% EtOAc/hexanes), affording 4-bromo-2-(bromomethyl)- 1-chlorobenzene (4.76 g, 70% yield). The product was used without further purification.

Reference： [1]Patent: WO2014/207052,2014,A1 .Location in patent: Page/Page column 107
[2]Patent: CN107652276,2018,A .Location in patent: Paragraph 0015; 0018
[3]Patent: CN104478670,2016,B .Location in patent: Paragraph 0029-0030
[4]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582
[5]Patent: US2009/69320,2009,A1 .Location in patent: Page/Page column 77; 78
[6]Patent: EP3135667,2017,A1 .Location in patent: Paragraph 0476-0477
[7]Journal of the Chemical Society. Perkin transactions I,1997,p. 2903 - 2909
[8]Patent: WO2010/132999,2010,A1 .Location in patent: Page/Page column 110

8
[ 54932-72-8 ]
[ 179894-93-0 ]
5-(4-Chloro-3-methyl-phenyl)-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 291 - 302

9
[ 54932-72-8 ]
[ 179895-41-1 ]
5-(4-Chloro-3-methyl-phenyl)-9-fluoro-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 303 - 310
[2]Journal of Medicinal Chemistry,1998,vol. 41,p. 2779 - 2785

10
[ 54932-72-8 ]
[ 179895-43-3 ]
9-Chloro-5-(4-chloro-3-methyl-phenyl)-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysen-5-ol [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 303 - 310

11
[ 54932-72-8 ]
[ 179895-47-7 ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2779 - 2785

12
[ 54932-72-8 ]
5-(4-Chloro-3-methyl-phenyl)-9-fluoro-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2779 - 2785

13
[ 54932-72-8 ]
5-(4-Chloro-3-methyl-phenyl)-9-fluoro-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 2779 - 2785

14
[ 54932-72-8 ]
(5-Bromo-2-chloro-benzyl)-triphenyl-phosphonium; bromide [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2903 - 2909

15
[ 54932-72-8 ]
(Z)-1-(5-Bromo-2-chlorophenyl)-2-(2-naphthyl)ethene [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2903 - 2909

16
[ 54932-72-8 ]
(E)-1-(5-Bromo-2-chlorophenyl)-2-(2-naphthyl)ethene [ No CAS ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1997,p. 2903 - 2909

17
[ 54932-72-8 ]
4-Chloro-N-(4-methanesulfonyl-phenyl)-3-methyl-benzamidine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

18
[ 54932-72-8 ]
2-(4-chloro-3-methylphenyl)-1-[4-(methylsulfonyl)phenyl]-4-trifluoromethyl-1H-imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

19
[ 54932-72-8 ]
[ 1026380-36-8 ]

Reference： [1]Journal of Medicinal Chemistry,1997,vol. 40,p. 1634 - 1647

20
[ 54932-72-8 ]
[ 40487-46-5 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 329,333

21
[ 54932-72-8 ]
[ 21900-52-7 ]

Reference： [1]Journal of the Chemical Society,1904,vol. 85,p. 1269

22
[ 54932-72-8 ]
[ 40487-49-8 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 329,333

23
[ 54932-72-8 ]
5-bromo-2-chloro-benzoic acid menthyl ester [ No CAS ]

Reference： [1]Journal of the Chemical Society,1904,vol. 85,p. 1269

24
[ 54932-72-8 ]
[ 99513-78-7 ]

Reference： [1]Journal of the Indian Chemical Society,1959,vol. 36,p. 329,333

25
[ 54932-72-8 ]
[ 98-80-6 ]
[ 19482-09-8 ]

Yield	Reaction Conditions	Operation in experiment
	With tetrabutylammomium bromide; potassium carbonate;palladium diacetate; In water;	(1) A mixture of 5.00 g (24.3 mmol) of <strong>[54932-72-8]5-bromo-2-chlorotoluene</strong>, 3.56 g (29.2 mmol) of dihydroxyphenylborane, 546mg (2.43 mmol) of palladium acetate (II), 9.41 g (29.2 mmol) of tetrabutylammonium bromide, 8.40 g (60.8 mmol) of potassium carbonate and 50 ml of water was stirred for 5 hours at 80 C. under nitrogen flow. The reaction solution was filtrated through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane) to obtain 3.92 g of 4-chloro-3-methylbiphenyl. 1H-NMR (CDCl3, TMS) delta (ppm): 7.30-7.60 (8H, m), 2.44 (3H, s)

Reference： [1]Patent: US2003/119670,2003,A1

26
[ 34241-39-9 ]
[ 54932-72-8 ]
[ 251085-86-6 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In methanol; tetrachloromethane; water; N,N-dimethyl-formamide;	Reference Example 5 Preparation of methyl N-(5-bromo-2-chlorobenzyl)carbamate (Compound II-b) A mixture comprising 10.0 g of <strong>[54932-72-8]5-bromo-2-chlorotoluene</strong>, 8.7 g of N-bromosuccinimide, 0.3 g of 2,2'-azobisisobutyronitrile and 60 ml of carbon tetrachloride, was refluxed under heating for 3 hours and, after cooling to room temperature, filtered and concentrated. A mixture comprising the obtained crude product, 5.9 g of potassium cyanate, 10 ml of methanol and 50 ml of N,N-dimethylformamide, was stirred at 100 C. for 2 hours. To this reaction mixture, water was added, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with isopropanol to obtain 6.8 g of methyl N-(5-bromo-2-chlorobenzyl)carbamate as white crystals.

Reference： [1]Patent: US6313071,2001,B1

27
[ 54932-72-8 ]
[ 14394-70-8 ]
(4-chloro-3-methyl-phenyl)-(2-chloro-5-methyl-pyrimidin-4-yl)-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 160℃; for 0.333333h;Microwave irradiation;	[0422] A mixture of 2-chloro-5-methyl-pyrimidin-4-ylamine (0.34 g, 2.34 mmol), 4- bromo-l-chloro-2-methyl-benzene (0.58 g, 2.8 ?1), Pd2(dba)3 (0.21 g, 0.23 mmol), Xantphos (0.47 g, 0.47 mmol) and cesium carbonate (2.3 g, 7 mmol) were suspended in <n="201"/>dioxane (9 mL) microwaved at 160 0C for 20 min. The reaction mixture was cooled to room temperature and centrifuged down. Solvents were then decanted and evaporated. Resulting residue was purified by flash chromatography on silica gel to afford title compound as yellow solids (0.24 g, 38%).

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 199-200

28
[ 936092-38-5 ]
[ 54932-72-8 ]
N₂-(4-(2-(pyrrolidin-1-yl)ethoxy)phenyl)-N₄-(4-chloro-3-methylphenyl)-5-methylpyrimidine-2,4-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; for 4h;Heating / reflux;	[0144] To a solution of the above-described intermediate 11 (80 mg, 0.25 mmol) in 1,4- dioxane (20 mL) was added 4-bromo-l-chloro-2-methylbenzene (63 mg, 0.30 mmol), Cs2CO3 (326 mg, 1.0 mmol), Pd2(dba)3 (18 mg, 0.02 mmol), and 4,5-bis(diphenylphosphino)- 9,9-dimethyxanthene (Xant Phos, 36 mg, 0.06 mmol). The mixture was heated under reflux for 4 h under Ar. The solid was filtered off. The solvent was removed in vacuo. The crude product was purified by HPLC and afforded the title compound XXIX (17.5 mg, 15%) as a yellow solid. 1H NMR (500 MHz, DMSO-d6): 1.85-1.89 (m, 2H); 1.96-2.01 (m, 2H); 2.12 (s, 3H); 2.25 (s, 3H); 3.04-3.08 (m, 2H); 3.51-3.55 (m, 4H); 4.32 (br, 2H); 6.91 (br, 2H); 7.04 (br, IH); 7.31 (br, IH); 7.41 (br, 2H); 7.58 (s, IH); 7.89 (br, IH); 9.75 (s, IH); 10.54 (s, IH); 11.13 (br, IH). MS (EI): 438.1.

Reference： [1]Patent: WO2007/53452,2007,A1 .Location in patent: Page/Page column 93

29
[ 54932-72-8 ]
[ 75336-86-6 ]
[ 1095543-73-9 ]

Yield	Reaction Conditions	Operation in experiment
77%	With sodium t-butanolate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In toluene; at 100℃; for 1h;Inert atmosphere;	Example 1] Synthesis of compound (I-40) a) Synthesis compound 3 [Show Image] [Show Image] Under the nitrogen atmosphere, toluene (7.5 ml) was added to a commercially available compound 2 (1.50 g, 7.30 mmol), a commercially available compound 1 (1.50 g, 7-30 mmol), and sodium tert-butoxide (842 mg, 8.76 mmol) were added, and the system was degassed, and replaced with nitrogen. Xantphos (127 mg, 0.22 mmol) and Pd2(dba)3 (67 mg, 0.67 mmol) were added to react them at 100C for 1 hour. Toluene (8 ml) was added to dilute the reaction, and this was filtered using Celite. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform-methanol) to obtain a compound 3 (1.27 g, yield 77%). 1H-NMR (CDCl3 / TMS) deltappm: 1.13 (d, J = 6.2Hz, 3H), 1.57 (s, 1H), 2.28-2.37 (m, 1H), 2.35 (s, 3H), 2.67 (dt, J = 3.5, 11.6Hz, 1H), 2.92-3.15 (m, 3H), 3.46 (d, J = 11.6Hz, 2H), 6.69 (dd, J = 8.9, 2.7Hz, 1H), 6.78 (d, J = 2.7Hz, 1H), 7.19 (d, J = 8.9Hz, 1H).

Reference： [1]Patent: EP2184272,2010,A1 .Location in patent: Page/Page column 29-30

30
[ 54932-72-8 ]
[ 163765-44-4 ]
[ 1121771-09-2 ]

Yield	Reaction Conditions	Operation in experiment
53%	With sodium t-butanolate;palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80℃; for 1h;Inert atmosphere;	Example 2] Synthesis of compound (I-41) a) Synthesis of compound 7 [Show Image] Under the nitrogen atmosphere, toluene (7.5 ml) was added to a compound 2 (1.50 g, 7.30 mmol), a commercially available compound 6 (1.46 g, 7.30 mmol), and sodium tert-butoxide (1.05 g, 10.9 mmol) were added, and the system was degassed, and replaced with nitrogen. BINAP (68.2 mg, 0.11 mmol), and palladium acetate (16.4 mg, 0.07 mmol) were added to react them at 80C for 1 hour. After cooling, a solvent was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain a compound 7 (1.26 g, yield 53%). 1H-NMR (CDCl3 / TMS) deltappm: 0.97 (d, J = 6.4Hz, 3H), 1.48 (s, 9H), 2.33 (s, 3H), 3.00-3.40 (m, 4H), 3.68-4.05 (m, 3H), 6.67 (dd, J = 8.9, 2.7Hz, 1H), 6.75 (d, J = 2.7Hz, 1H), 7.20 (d, J = 8.9Hz, 1H).

Reference： [1]Patent: EP2184272,2010,A1 .Location in patent: Page/Page column 31

31
[ 1232692-92-0 ]
[ 54932-72-8 ]
[ 1232693-07-0 ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 8270 - 8272
[2]Advanced Synthesis and Catalysis,2011,vol. 353,p. 1285 - 1305

32
[ 532-24-1 ]
[ 54932-72-8 ]
(+/-)-3-(4-chloro-3-methyl-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%		Method B (+/-)-3-(4-Chloro-3-methylphenyl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene hydrochloric acid salt A mixture of <strong>[54932-72-8]5-bromo-2-chlorotoluene</strong> (10.0 g, 48.7 mmol) in diethylether (100 ml) was cooled to -700C followed by addition of buthyllithium (21.4 ml, 2.5 M) at -700C. The mixture was stirred at room temperature for 1 h followed by addition of tropinone (6.77 EPO <DP n="17"/>g, 48.7 mmol) at -700C, solved in THF. The mixture was stirred at -700C for 1 h. The mixture was allowed to warm to room temperature. The mixture was made acidic by adding aqueous hydrochloric acid (1 M). The acidic aqueous phase was washed with diethylether (50 ml). The mixture was made alkaline by adding aqueous sodium hydroxide followed by extraction with diethylether (3 x 50 ml). Yield of intermediate (+)- 3-(4-chloro-3-methyl-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol 11.6 g (90%). A mixture of (+/-)-3-(4-chloro-3-methyl-phenyl)-8-methyl-8-aza-bicyclo[3.2.1]octan-3-ol (7.5 g, 28.2 mmol) and aqueous hydrogen chloride (37%) was stirred at reflux for 1 h. The mixture was allowed to cool to room temperature and was made alkaline by adding concentrated aqueous ammonia. Yield 6.0 g (86%). The hydrochloric salt was precipitated. Mp 177-179C.

Reference： [1]Patent: WO2007/25978,2007,A1 .Location in patent: Page/Page column 15-16

33
[ 54932-72-8 ]
(1R,5S)-2-(3'-methyl-1',2',4'-oxadiazol-5'-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene [ No CAS ]
3β-(4-chloro-3-methylphenyl)-2α-(3'-methyl-1',2',4'-oxadiazol-5-yl)tropane [ No CAS ]
3α-(4-chloro-3-methylphenyl)-2α-(3'-methyl-1',2',4'-oxadiazol-5-yl)tropane [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 8345 - 8353

34
[ 1297549-70-2 ]
[ 54932-72-8 ]
[ 1297552-00-1 ]

Yield	Reaction Conditions	Operation in experiment
		Example 172AEthyl(3R)-2-(4-chloro-3-methylphenyl)-4,4,4-trifluoro-3-methylbutanoate (Diastereomer Mixture); 29.2 ml (29.2 mmol) of a 1 M solution of lithium hexamethyldisilazide in toluene were cooled to -10 C., and a solution of 4.30 g (23.4 mmol) of ethyl(3R)-4,4,4-trifluoro-3-methylbutanoate in 26 ml of abs. toluene was added dropwise. The mixture was stirred for 10 min At -10 C., a solution, prepared beforehand, of 5.0 g (19.5 mmol, 80% pure) of <strong>[54932-72-8]5-bromo-2-chlorotoluene</strong>, 131 mg (0.58 mmol) of palladium(II) acetate and 483 mg (1.23 mmol) of 2-dicyclohexyl-phosphino-2'-(N,N-dimethylamino)biphenyl in 26 ml of abs. toluene was then added dropwise. The resulting reaction mixture was initially stirred at RT for 1 h and then at 80 C. for 4 h. After cooling, the mixture was diluted with ethyl acetate, washed twice with sat. aqueous sodium bicarbonate solution and once with sat. sodium chloride solution, dried over sodium sulphate and concentrated under reduced pressure. This gave 7.80 g of the title compound as a crude product which was directly reacted further.LC-MS (Method 4): Rt=1.55 min; m/z=309 (M+H)+.

Reference： [1]Patent: US2011/130445,2011,A1 .Location in patent: Page/Page column 70-71

35
[ 1232692-92-0 ]
[ 54932-72-8 ]
[ 1232693-31-0 ]

Reference： [1]Advanced Synthesis and Catalysis,2011,vol. 353,p. 1285 - 1305

36
[ 54932-72-8 ]
[ 126317-99-5 ]
[ 1313602-87-7 ]

Reference： [1]Journal of Medicinal Chemistry,2011,vol. 54,p. 5031 - 5047

37
[ 59843-69-5 ]
[ 54932-72-8 ]
[ 1067197-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With salicylaldehyde-oxime; caesium carbonate; copper(II) oxide; In N,N-dimethyl-formamide; at 140℃;	A mixture of 3-(3-chlorophenyl)-1H-pyrazole (5.3 g, 29.8 mmol) (prepared according to the method given in European Patent Publication EP 538156), salicylaldoxime (0.58 g, 4.25 mmol), <strong>[54932-72-8]5-bromo-2-chlorotoluene</strong> (2.8 g, 21.3 mmol), copper oxide (0.15 g, 1.06 mmol) and cesium carbonate (11.8 g, 36.2 mmol) in 20 mL of Af N-dimethylformamide was heated at 140 C overnight and then allowed to cool to room temperature. The resulting suspension was filtered and the filtrate was concentrated under reduce pressure. The resulting residue was purified by medium pressure liquid chromatography (2 to 10% gradient of ethyl acetate in hexanes as eluant) to give the title compound as a white solid (1.4 g). 1H NMR (CDCl3): 5 7.92-7.30 (m, 8H), 6.78 (s, 1H), 2.46 (s, 3H)

Reference： [1]Patent: WO2008/124092,2008,A2 .Location in patent: Page/Page column 52

38
[ 54932-72-8 ]
[ 1067197-26-5 ]

Reference： [1]Patent: WO2008/124092,2008,A2

39
[ 54932-72-8 ]
[ 1067196-86-4 ]

Reference： [1]Patent: WO2008/124092,2008,A2

40
[ 95-49-8 ]
[ 89794-02-5 ]
[ 54932-72-8 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In 1,2-dichloro-ethane; at 60℃; for 15h;Sealed tube;	General procedure: NBS (1.0 mmol) and catalyst 1 (0.1 or 1 mol % Au based on the substrate) were weighted into a 10 mL sealed vessel, and then DCE (2 mL) and the substrate (1.0 mmol) were added. The reaction was stirred at the required temperature for the specified time. After reaction, the catalyst was removed with a magnet, and the solution was concentrated under reduced pressure and purified by column chromatography.

Reference： [1]Tetrahedron Letters,2013,vol. 54,p. 1063 - 1066

41
[ 1373046-69-5 ]
[ 54932-72-8 ]
tert-butyl 1-(4-chloro-3-methylphenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		5-Bromo-2-chlorotoluene (CAS 54932-72-8, 483 iL, 3.64 mmcl) was dissolved in THF (8.1 mL) and cooled to -78C under argon atmosphere. n-Butyl lithium (2.5 M in hexane, 1.53 mL, 3.83 mmol) was added. After 15 mm tert-butyl 1-(methoxy(methyl)amino)-3,3-dimethyl-1- oxobutan-2-ylcarbamate (Example 43a, 500 mg, 1.82 mmol) dissolved in THE (8.1 mL) wasadded to the mixture. The mixture was stirred at -78C for 1 h before the mixture was quenched by adding saturated aqueous NH4CI. Extraction with ethyl acetate, drying of the organic layer over Mg504 and evaporation gave tert-butyl 1-(4-chloro-3-methylphenyl)-3,3- dimethyl-1-oxobutan-2-ylcarbamate (427 mg, 69%).MS (ESI) m/z 340.2 [M+H]

Reference： [1]Patent: WO2014/184235,2014,A1 .Location in patent: Page/Page column 135

42
[ 54932-72-8 ]
3-[(5-bromo-2-chloro-phenyl)methyl]oxazolidin-2-one [ No CAS ]

Reference： [1]Patent: WO2014/207052,2014,A1

43
[ 54932-72-8 ]
3-[(5-acetyl-2-chloro-phenyl)methyl]oxazolidin-2-one [ No CAS ]

Reference： [1]Patent: WO2014/207052,2014,A1

44
[ 54932-72-8 ]
3-[[2-chloro-5-[(E)-N-[(3,4-dichlorophenyl)methoxy]-C-methyl-carbonimidoyl]phenyl]methyl]oxazolidin-2-one [ No CAS ]

Reference： [1]Patent: WO2014/207052,2014,A1

45
[ 54932-72-8 ]
1-methyl-4-(3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-pyrazole [ No CAS ]

Reference： [1]Patent: US2016/16951,2016,A1

46
[ 54932-72-8 ]
8-(2-methyl-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-1,6-naphthyridin-2-ol [ No CAS ]

Reference： [1]Patent: US2016/16951,2016,A1

47
[ 54932-72-8 ]
2-chloro-8-(2-methyl-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-1,6-naphthyridine [ No CAS ]

Reference： [1]Patent: US2016/16951,2016,A1

48
[ 54932-72-8 ]
8-(2-methyl-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-1,6-naphthyridine-2-carbonitrile [ No CAS ]

Reference： [1]Patent: US2016/16951,2016,A1

49
[ 54932-72-8 ]
8-(2-methyl-4-(1-methyl-1H-pyrazol-4-yl)phenyl)-1,6-naphthyridine-2-carboxamide [ No CAS ]

Reference： [1]Patent: US2016/16951,2016,A1

50
[ 54932-72-8 ]
[ 761446-44-0 ]
4-(4-chloro-3-methylphenyl)-1-methyl-1H-pyrazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In tetrahydrofuran; water; at 120℃; for 1h;Microwave irradiation;	a. 4-(4-chloro-3-methylphenyl)-1-methyl-1H-pyrazole A mixture of <strong>[54932-72-8]2-chloro-5-bromotoluene</strong> (305 mg, 1.48 mmol), 1-methylpyrazole-4-boronic acid pinacol ester (315 mg, 1.51 mmol), Pd(dppf)Cl2 (130 mg, 0.16 mmol), and K2CO3 (400 mg, 2.89 mmol) in a mixture of THF (4 mL) and water (1.2 mL) was heated at 120 C. for 1 h under microwave irradiation. The reaction mixture was concentrated in vacuo and purified by Biotage (SNAP 25 g column, cyclohexane/EtOAc 90/10->50/50) to give the title compound as a brown oil (215 mg, 70%).

Reference： [1]Patent: US2016/16951,2016,A1 .Location in patent: Paragraph 0267; 0268

51
[ 627-19-0 ]
[ 54932-72-8 ]
1-chloro-2-methyl-4-(pent-1-yn-1-yl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 2977 - 2980

52
[ 627-19-0 ]
[ 54932-72-8 ]
(Z)-1-(4-chloro-3-methylphenyl)-2-cyanopent-1-en-1-yl trifluoromethanesulfonate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 2977 - 2980

53
[ 54932-72-8 ]
[ 177-11-7 ]
8-(4-chloro-3-methylphenyl)-1,4-dioxa-8-azaspiro[4.5]decane [ No CAS ]

Reference： [1]Patent: WO2016/31255,2016,A1 .Location in patent: Page/Page column 152; 153

54
[ 54932-72-8 ]
[ 177-11-7 ]
1-(4-chloro-3-methylphenyl)piperidin-4-one [ No CAS ]

Reference： [1]Patent: WO2016/31255,2016,A1

55
[ 54932-72-8 ]
4-bromo-2-(bromomethyl)-1-chlorobenzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

56
[ 54932-72-8 ]
C₁₇H₁₉ClO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

57
[ 54932-72-8 ]
C₁₅H₁₃ClO₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

58
[ 54932-72-8 ]
C₂₁H₂₇ClO₂Si [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

59
[ 54932-72-8 ]
C₂₇H₃₂BrClO₂Si [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

60
[ 54932-72-8 ]
C₄₈H₆₀Cl₂O₄Si₂ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582
[2]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

61
[ 54932-72-8 ]
C₆₀H₈₈Cl₂O₄Si₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582
[2]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

62
[ 54932-72-8 ]
C₆₀H₈₈Cl₂O₄Si₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582
[2]Journal of the American Chemical Society,2016,vol. 138,p. 6577 - 6582

63
[ 54932-72-8 ]
9b-(4-chloro-3-methyl-phenyl)-2,3-dihydro-1H-imidazo[2,1-a]isoindol-5-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1356 - 1359

64
[ 54932-72-8 ]
9b-(4-chloro-3-methyl-phenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1356 - 1359

65
[ 54932-72-8 ]
9b-(4-chloro-3-methyl-phenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one [ No CAS ]
9b-(4-chloro-3-methyl-phenyl)-1-(3,4-difluorobenzoyl)-2,3-dihydroimidazo[2,1-a]isoindol-5-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1356 - 1359

66
[ 85-44-9 ]
[ 54932-72-8 ]
[ 141123-11-7 ]

Yield	Reaction Conditions	Operation in experiment
50.4%		To a stirring solution of <strong>[54932-72-8]4-bromo-1-chloro-2-methyl-benzene</strong> 5 (4.92mL, 37.1mmol) in THF (75mL) cooled to -78C was added n-butyllithium (14.9mL, 37.1mmol) dropwise. The solution was stirred at -78C for 30min and then was added to a stirring solution of phthalic anhydride 6 (5.00g, 33.8mmol) in THF (90mL) at -78C. The reaction was stirred at -78C for 2h before being quenched with 1N HCl (100mL). The solution was allowed to warm to rt, the layers were separated and the aqueous layer was extracted with EtOAc (3×100mL). The combined organic layers were passed through a phase separator and concentrated. The crude material was purified using Teledyne ISCO Combi-Flash system (solid loading, 40G column, 40-80% EtOAc, 20min run) to give 2-(4-chloro-3-methyl-benzoyl)benzoic acid 7 (4.67g, 50.4% yield) as a white solid. 1H NMR (400MHz, CDCl3) delta (ppm): 8.10 (d, J=7.8Hz, 1H), 7.68 (dt, J=7.6, 1.2Hz, 1H), 7.64-7.62 (m, 1H), 7.59 (dt, J=7.9, 1.2Hz, 1H), 7.44 (dd, J=8.2, 2.2Hz, 1H), 7

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 1356 - 1359

67
[ 54932-72-8 ]
C₈H₅BrClN [ No CAS ]

Reference： [1]Patent: EP3135667,2017,A1

68
[ 54932-72-8 ]
5-bromo-2-chlorophenylacetic acid [ No CAS ]

Reference： [1]Patent: EP3135667,2017,A1

69
[ 54932-72-8 ]
C₉H₈BrClO₂ [ No CAS ]

Reference： [1]Patent: EP3135667,2017,A1

70
[ 583-75-5 ]
[ 54932-72-8 ]

Yield	Reaction Conditions	Operation in experiment
87%	With hydrogenchloride; copper(l) chloride; sodium nitrite; In 1,4-dioxane; water; at -5 - 80℃; for 3.5h;	11.7 g (63.2 mmol) of 4-bromo-2-methylaniline was added to 45 ml (6 mol / L) hydrochloric acid solution and stirred well to make the salt.The resulting solution was placed in an ice-salt bath, cooled to below -5 C, and about 20% sodium nitrite solution (4.8 g, 69.5 mmol, 20 ml) was slowly added dropwise to maintain the temperature below 0 C.Drop, add 12ml of 1,4-dioxane, stir well.The above diazonium salt solution was slowly added to a 3 mol / L hydrochloric acid solution (20 ml) of cuprous chloride (6.7 g, 66.4 mmol) in an ice-water bath and stirred vigorously. After completion of the dropwise addition, the mixture was stirred at room temperature for 0.5 h, To 80 C for 3 h.Cooled, extracted with dichloromethane (75 ml * 2) and the extract was saturated with NaHCO3(150 ml), water (150 ml) and saturated brine (100 ml * 2), dried over anhydrous sodium sulfate overnight and concentrated under reduced pressure to give 11.2 g (yield 87%) of reddish brown liquid.
87%		Take 4-bromo-2-methylaniline 184kg, dissolved in 600kg concentrated hydrochloric acid, cooled to -5C in an ice bath, and add sodium nitrite dropwise.Aqueous solution (sodium nitrite 68kg + ice water 200kg), 1h drip, control temperature does not exceed 0 C in the dropping process, after the completion of the dropping, the reaction below -5 C 2h, after the reaction is completed,In the reaction system, 120 kg of cuprous chloride was added, and the system was slowly heated to 60 degrees for 3 hours. After the reaction was completed, 400 kg of ethyl acetate was added to the system for extraction, washed with water until neutral, dried over anhydrous sodium sulfate, and the ethyl acetate was recovered under reduced pressure. Distillation under reduced pressure gave a yellow liquid, 176 kg, with a yield of 87%.

Reference： [1]Patent: CN104478670,2016,B .Location in patent: Paragraph 0027-0028
[2]Patent: CN107652276,2018,A .Location in patent: Paragraph 0015; 0017

71
[ 95-53-4 ]
[ 54932-72-8 ]

Reference： [1]Patent: CN104478670,2016,B
[2]Patent: CN107652276,2018,A

72
[ 54932-72-8 ]
tert-butyl 4-[2-(2-methyl-4-bromophenylmercapto)phenyl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: CN107513048,2017,A

73
[ 54932-72-8 ]
tert-butyl 4-[2-(2-methyl-4-trideuteromethylphenylmercapto)phenyl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: CN107513048,2017,A
[2]Patent: CN107513048,2017,A

74
[ 54932-72-8 ]
4-[2-(2-methyl-4-trideuteromethylphenylmercapto)phenyl]piperazine hydrobromide [ No CAS ]

Reference： [1]Patent: CN107513048,2017,A
[2]Patent: CN107513048,2017,A

75
[ 54932-72-8 ]
1-[2-(2-methyl-4-bromophenylmercapto)phenyl]piperazine [ No CAS ]

Reference： [1]Patent: CN107513048,2017,A

76
[ 54932-72-8 ]
[ 137-07-5 ]
2-(2-methyl-4-bromo-phenylmercapto)aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
83.2%	With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; In water; at 130℃; for 18h;Inert atmosphere;	Under argon, a 250 mL three-necked flask was charged with 19.7 g of <strong>[54932-72-8]2-chloro-5-bromotoluene</strong> (I), 11.7 g of o-aminothiophenol (n), 0.5 g of cuprous chloride, 36.5 g of tetramethylethylenediamine and 50 mL of water,Mechanical stirring, oil bath 130 C, the reaction 18 h.The reaction mixture was cooled to room temperature, extracted with 50 1111> 3 ethyl acetate, 12.5 mL * 3 aqueous ammonia and extracted with 25 mL * 3 purified water three times. The combined ethyl acetate phases were washed with 50 mL of purified water and 15 mL of aqueous ammonia, Brine, dried over anhydrous sodium sulfate. The dried ethyl acetate layer was dried, after adding 25 mL of petroleum ether dissolved, rapidly cooled to -5--10 C under stirring, and accompanied by a large amount of solid precipitation, vacuum filtration, the filter cake with petroleum ether leaching wash. The filter cake was collected and dried under reduced pressure at 40 C to give 2- (2-methyl-4-bromo-phenylmercapto) aniline(1Pi) 16.39 g, yield 83.2%, purity 90.1%.

Reference： [1]Patent: CN107513048,2017,A .Location in patent: Paragraph 0019; 0029

77
[ 54932-72-8 ]
[ 186550-13-0 ]
C₁₆H₂₃ClN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.4%		Nitrogen gas was purged through a stirred solution of 5-bromo-2-chiorotoluene (452 muIota, 3.41 mmol) in 1 ,4-dioxane (15 ml) for 30 mins. 2,2'-Bis(diphenylphosphino)-1 , 1 '- binaphthyl (212 mg, 0.34 mmol), Pd(OAc)2 (153 mg, 0.68 mmol) and Cs2C03 (2.22 g, 6.81 mmol) were then added. The stirred solution was then purged of nitrogen for a further 30 min after which 1-Boc-3-aminopyrrolidine (745 muIota, 4.09 mmol) was added and solution stirred at reflux for 48 h under N2. The solvent was then evaporated in vacuo and the crude residue dissolved in EtOAc (40 ml) which was then washed with water (2 x 30 ml), brine (2 chi 30 ml), dried with Na2S04, filtered and concentrated. The crude residue was then purified by column chromatography (100% CyHex to 10% EtOAc/CyHex) to obtain WIN-321 -142-01 as a solid (111 mg, 10.4%).1H NMR (CDCI3): delta 7.13 (d, J 8.4 Hz, 1H), 6.48 (d, J 2.6 Hz, 1H), 6.39 (dd, J 8.58, 2.86 Hz, 1H), 3.99 (br. s., 1H), 3.79-3.57 (m, 2H), 3.56-3.38 (m, 2H), 3.31 -3.14 (m, 1H), 2.30 (s, 3H), 2.10 - 2.26 (m, 1 H), 1.96 - 1.79 (m, 1 H), 1.47 (s, 9H). MS, m/z = 255 (100) [M-56], 257 (30).

Reference： [1]Patent: WO2017/219083,2017,A1 .Location in patent: Page/Page column 76; 77

78
[ 54932-72-8 ]
[ 1279691-36-9 ]

Reference： [1]Patent: CN107652276,2018,A

79
[ 54932-72-8 ]
[ 864070-44-0 ]

Reference： [1]Patent: CN107652276,2018,A

80
[ 110-89-4 ]
[ 1013-88-3 ]
[ 54932-72-8 ]
C₂₅H₂₆N₂ [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 2301 - 2305

81
1-(3,5-difluorophenyl)-1H-1,2,4-triazol-3-amine [ No CAS ]
[ 54932-72-8 ]
N-(4-chloro-3-methylphenyl)-1-(3,5-difluorophenyl)-1,2,4-triazol-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With [2-(di-tert-butylphosphino)-2?,4?,6?-triisopropyl-1,1?-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; In 1,4-dioxane; tert-butyl alcohol; at 90℃; for 3h;	1-(3,5-difluorophenyl)-1,2,4-triazol-3-amine (2.95 g, 15.04 mmol), <strong>[54932-72-8]4-bromo-1-chloro-2-methyl-benzene</strong> (4 mL, 30.17 mmol), sodium tert-butoxide (3.15 g, 32.78 mmol) and chloro(2-di-t-butylphosphino-2',4',6'-tri-i-propyl-1,1'-biphenyl)[2- (2-aminoethyl)phenyl]palladium(II) (/-BuXPhos Palladacycle) (460 mg, 0.6227 mmol) were slurried into dry tert-butanol (40 mL) and dry 1,4-dioxane (12 mL) and purged with nitrogen for approximately 5 minutes. The slurry was stirred at 90C for 3 hours in a parr bottle with a Qian cap. The reaction mixture was cooled to room temperature and poured into 500 mL of water. The precipitate was filtered and washed with additional water (approximately 250 mL) and methanol (200 mL), then dried under high vacuum at 50C overnight to yield N-(4-chloro-3-methyl-phenyl)-1-(3,5-difluorophenyl)-1,2,4-triazol-3- amine (4.05 g, 75%). MR (300 MHz, OMSO-de) delta 9.69 (s, 1H), 9.19 (s, 1H), 7.73 - 7.60 (m, 2H), 7.60 - 7.50 (m, 2H), 7.35 - 7.19 (m, 2H), 2.31 (s, 3H) ppm. ESI-MS m/z calc. 320.06403, found 321.11 (M+l)+; Retention time: 1.01 minutes.

Reference： [1]Patent: WO2018/106646,2018,A1 .Location in patent: Paragraph 00437

82
[ 54932-72-8 ]
[ 57260-71-6 ]
tert-butyl 4-(4-chloro-3-methylphenyl)piperazine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; sodium t-butanolate; In toluene; at 60℃;	<strong>[54932-72-8]4-bromo-1-chloro-2-methylbenzene</strong> (1.5 g, 7.30 mmol), tert-butyl piperazine-1-carboxylate (1.36 g, 7.30 mmol), Tris(dibenzylideneacetone)dipalladium(0) (69 mg, 0.07 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (91 mg, 0.15 mmol) and sodium tert- butoxide (982 mg, 10.22 mmol) were dissolved in toluene (15 mL), and the reaction mixture was stirred overnight at 60C. The reaction mixture was filtrated, diluted with water and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04, filtrated and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford the compound of Reference Example 10 (1.91 g, 84%). 1H-NMR (CDCl3) delta: 7.18 (1H, d, J = 8.5 Hz), 6.76 (1H, s), 6.67 (1H, d, J = 8.5 Hz), 3.57- 3.53 (4H, m), 3.08-3.04 (4H, m), 2.31 (3H, s), 1.46 (9H, s).
44 mg	With tris-(dibenzylideneacetone)dipalladium(0); potassium tert-butylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In 1,4-dioxane; at 100℃; for 3h;	Step 1: A solution of compound X-a-1 (90 g, 0.438 mol), N-Boc-piperazine (114 g, 0.613 mol), pd2(dba)3 (4.0 g, 0.004 mol), BINAP (5.1 g, 0.008 mol) and potassium tert-butoxide (98 g, 0.876 mol) in 1,4-dioxane (1 L) was heated to 100 C. and stirred for 3 h. The mixture was poured into water, filtered over celite and washed with ethyl acetate. The filtrate was extracted by ethyl acetate (1L*2), the organic layers were combined, washed with saturated brine (500 mL), dried over anhydrous sodium sulfate and concentrated, the residue was recrystallized from ethanol to give 44 g of solid compound X-a-2. ESI-MS [M+H]+: 311.2.

Reference： [1]Patent: WO2018/129411,2018,A1 .Location in patent: Paragraph 00224
[2]Patent: US2020/48209,2020,A1 .Location in patent: Page/Page column 0355-0356

83
[ 54932-72-8 ]
[ 57260-71-6 ]
tert-butyl 4-[3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate [ No CAS ]

Reference： [1]Patent: WO2018/129411,2018,A1

84
[ 54932-72-8 ]
[ 55-21-0 ]
N-(4-chloro-3-methylphenyl)benzamide [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 6112 - 6116

85
[ 54932-72-8 ]
C₂₂H₂₄Cl₂FN₃O₃S*(x)ClH [ No CAS ]

Reference： [1]Patent: US2020/48209,2020,A1

86
[ 54932-72-8 ]
(x)BrH*C₂₂H₂₄Cl₂FN₃O₃S [ No CAS ]

Reference： [1]Patent: US2020/48209,2020,A1

87
[ 54932-72-8 ]
(x)CH₄O₃S*C₂₂H₂₄Cl₂FN₃O₃S [ No CAS ]

Reference： [1]Patent: US2020/48209,2020,A1

88
[ 54932-72-8 ]
C₂₂H₂₄Cl₂FN₃O₃S*C₄H₄O₄ [ No CAS ]

Reference： [1]Patent: US2020/48209,2020,A1

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P378
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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.
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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.
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Physical hazards
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H200	Unstable explosive
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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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
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H271	May cause fire or explosion; strong oxidizer
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H290	May be corrosive to metals
Health hazards
Code	Phrase
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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
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H331	Toxic if inhaled
H332	Harmful if inhaled
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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. 54932-72-8 ] {[proInfo.proName]}

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[ 54932-72-8 ] Synthesis Path-Upstream 1~15

[ 54932-72-8 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 54932-72-8 ]

Aryls

Bromides

Chlorides

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[ 54932-72-8 ]