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[ CAS No. 25016-01-7 ]

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CAS No. :	25016-01-7	MDL No. :	MFCD00003347
Formula :	C₈H₇BrO₂	Boiling Point :	289.1°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	-
M.W :	215.04 g/mol	Pubchem ID :	90684
Synonyms :

Safety of [ 25016-01-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 25016-01-7 ]

Upstream synthesis route of [ 25016-01-7 ]
Downstream synthetic route of [ 25016-01-7 ]

[ 25016-01-7 ] Synthesis Path-Upstream 1~8

1
[ 25016-01-7 ]
[ 16740-73-1 ]

Reference： [1] Drug Metabolism and Disposition, 2012, vol. 40, # 10, p. 2002 - 2008,7

2
[ 25016-01-7 ]
[ 35431-26-6 ]

Reference： [1] Journal of the American Chemical Society, 2006, vol. 128, # 33, p. 10694 - 10695

3
[ 25016-01-7 ]
[ 7062-40-0 ]

Reference： [1] Journal of Medicinal Chemistry, 1995, vol. 38, # 12, p. 2050 - 2060

4
[ 25016-01-7 ]
[ 80866-82-6 ]

Reference： [1] Patent: JP2005/120047, 2005, A, . Location in patent: Page/Page column 89-90
[2] Journal of Medicinal Chemistry, 2007, vol. 50, # 3, p. 528 - 542
[3] Molecules, 2011, vol. 16, # 9, p. 7458 - 7479
[4] Synlett, 2012, vol. 23, # 8, p. 1205 - 1208
[5] Journal of Medicinal Chemistry, 2005, vol. 48, # 7, p. 2667 - 2677
[6] Journal fuer Praktische Chemie (Leipzig), 1958, vol. <4> 6, p. 170,172
[7] Journal of Medicinal Chemistry, 1995, vol. 38, # 12, p. 2050 - 2060
[8] Tetrahedron Letters, 2006, vol. 47, # 46, p. 8021 - 8024

5
[ 25016-01-7 ]
[ 81224-16-0 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1981, vol. 18, p. 1373 - 1377

6
[ 25016-01-7 ]
[ 144649-99-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	for 15 h; Reflux	5-Bromo-2-methoxybenzaldehyde (20.00 mmol, 4.30 g) was dissolved in formic acid (20 mL) and treated with hydroxylamine hydrochloride (21.00 mmol, 1.45 g) and sodium acetate (26.00 mmol, 2.13 g). The reaction mixture was heated at reflux for 15 hours. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate (250 mL). The organics were washed with saturated sodium bicarbonate solution (2.x.200 mL) and then dried with MgSO₄. The organics were filtered and evaporated under reduced pressure to yield the title compound as a white solid. Yield=4.10 g, 97percent. Analytical LCMS method 2, retention time 6.07 min, M+H=214, 216. ¹H NMR: (CDCl₃) δ: 7.66-7.61 (m, 2H), 6.87 (d, 1H), 3.92 (s, 3H).

Reference： [1] Science China Chemistry, 2015, vol. 58, # 4, p. 747 - 750
[2] Patent: US2009/247519, 2009, A1, . Location in patent: Page/Page column 143
[3] Patent: US2003/18025, 2003, A1,
[4] Patent: US5633376, 1997, A,
[5] Patent: US5159083, 1992, A,

7
[ 25016-01-7 ]
[ 679433-91-1 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 4, p. 715 - 734

8
[ 25016-01-7 ]
[ 166530-78-5 ]

Reference： [1] Synlett, 2016, vol. 27, # 9, p. 1339 - 1343

[ 25016-01-7 ] Synthesis Path-Downstream 1~26

1
[ 7017-52-9 ]
[ 25016-01-7 ]
[ 2476-35-9 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1937,vol. 205,p. 146

2
[ 7017-48-3 ]
[ 108-24-7 ]
[ 25016-01-7 ]
[ 5435-44-9 ]
2,3<i>t</i>-bis-(5-bromo-2-methoxy-phenyl)-acrylic acid [ No CAS ]
5,5'-dibromo-2,2'-dimethoxy-<i>trans</i>-stilbene [ No CAS ]

Reference： [1]Journal of the Chemical Society,1946,p. 567,571

3
[ 939-79-7 ]
[ 25016-01-7 ]
5'-bromo-2-nitro-2'-methoxy-<i>trans</i>-stilbene-carbonitrile-⁽⁴⁾ [ No CAS ]

Reference： [1]Journal of the Chemical Society,1946,p. 567,571

4
[ 1071-36-9 ]
[ 25016-01-7 ]
3<i>t</i>-(5-bromo-2-methoxy-phenyl)-2-cyano-acrylic acid [ No CAS ]

Reference： [1]Journal of the Chemical Society,1953,p. 119,121

5
[ 25016-01-7 ]
[ 80866-82-6 ]

Reference： [1]Patent: JP2005/120047,2005,A .Location in patent: Page/Page column 89-90
[2]Journal of Medicinal Chemistry,2007,vol. 50,p. 528 - 542
[3]Molecules,2011,vol. 16,p. 7458 - 7479
[4]Synlett,2012,vol. 23,p. 1205 - 1208
[5]Journal of Medicinal Chemistry,2005,vol. 48,p. 2667 - 2677
[6]Journal fur praktische Chemie (Leipzig 1954),1958,vol. <4> 6,p. 170,172
[7]Journal of Medicinal Chemistry,1995,vol. 38,p. 2050 - 2060
[8]Tetrahedron Letters,2006,vol. 47,p. 8021 - 8024

6
[ 25016-01-7 ]
[ 2476-35-9 ]

Yield	Reaction Conditions	Operation in experiment
49%	With potassium permanganate; In acetone; at 5 - 30℃;	Example 3 Synthesis of 5-bromo-2-methoxybenzoic acid To a solution of 5-bromo-2-methoxybenzaldehyde (20 g, 93.0 mmol) in acetone (100 mL) was added potassium permanganate (KMnO4) (14.7 g, 93.0 mmol) in small portions at 5 C. during 2 h. The resulted mixture was stirred at room temperature for overnight, and then the mixture was filtered. The filtrate was adjusted pH=1 by using hydrochloric acid (5 M), the yellow solid was filtered and dried under vacuum to afford 5-bromo-2-methoxybenzoic acid (10.5 g, yield: 49%). m/z: [M-H]- 228.9
37%		Suspend commercially available 5-bromo-2-methoxybenzaldehyde (100 g, 465 mmol) in acetone (700 mL) and water (1100 mL) and stir at 5 C. Treat with potassium pennanganate (88.2 g, 558 mmol) in portions over a 2 h period. Remove ice bath and stir at room temperature for about 20 h. Filter mixture through a pad of filtering agent and acidify filtrate to about pH = 1 with 5 N hydrochloric acid. Filter precipitate, air dry, redissolve in dichloromethane (300 mL), dry (magnesium sulfate), filter-, and concentrate to give the title compound as a yellow solid (40.0 g, 37% yield). ¹H NMR (CDCl3) No. 10.7 (br s, 1H), 8.28 (d, J = 2.6 Hz, 1H), 7.66 (dd, J = 8.8,2.6 Hz, 1H), 6.96 (d, J = 8.8 Hz, 1H), 4.08 (s, 3H) ; MS (ES) : m/z = 212
	With aldehyde; permanganate(VII) ion;	Method A; This biphenylic compound was prepared by means of a Suzuki cross-coupling reaction catalysed by Pd(0) from the corresponding boronic acid and a bromine or iodine derivative. First of all, the bromoderivative ethyl 5-bromo-2-methoxybenzoate was prepared. This was obtained in two-step synthesis from the commercial aldehyde, 5-bromo-o-anisaldehyde, which is first treated with a permanganate solution to obtain the corresponding carboxylic acid and then esterified by in situ formation of the corresponding acid chloride by reaction with thionyl chloride and reaction with ethanol. Suzuki's reaction: 1.15 ml (2.29 mmol, 2 eq) of a 2 N aqueous solution of sodium carbonate and 17 mg (0.111 mmol, 0.096 eq) of the Pd(0) catalyst, tetrakis(triphenyl)phosphine palladium (0), and lastly, 300 mg (1.16 mmol) of the bromoderivative (ethyl 5-bromo-2-methoxybenzoate) were added to a solution in dioxane of 190 mg (1.21 mmol, 1 eq) of 2,4-difluorophenylboronic acid. It was heated under reflux for 2 hr. It was left to cool and the catalyst was filtered through a silica gel column. It was diluted with dichloromethane and extracted with water. After the usual work-up, 330 mg of a high purity (95% by HPLC) crude was obtained.

Reference： [1]Liebigs Annalen der Chemie,1989,p. 863 - 882
[2]Patent: US2017/37038,2017,A1 .Location in patent: Paragraph 0121; 0122 0123
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 5233 - 5238
[4]Patent: WO2005/100301,2005,A1 .Location in patent: Page/Page column 35-36
[5]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6819 - 6829
[6]Journal of Organic Chemistry,1960,vol. 25,p. 1016 - 1020
[7]Journal of labelled compounds and radiopharmaceuticals,2003,vol. 46,p. S161 - S161
[8]Patent: EP1679299,2006,A1 .Location in patent: Page/Page column 10-11

7
[ 67-56-1 ]
[ 135-02-4 ]
[ 21702-84-1 ]
[ 7120-41-4 ]
[ 25016-01-7 ]

Reference： [1]Synthetic Communications,2002,vol. 32,p. 2275 - 2286

8
[ 21702-84-1 ]
[ 68-12-2 ]
[ 25016-01-7 ]

Reference： [1]Tetrahedron,2005,vol. 61,p. 6590 - 6595

9
[ 25016-01-7 ]
[ 19063-55-9 ]

Reference： [1]Synthetic Communications,1999,vol. 29,p. 929 - 936
[2]Chemical Communications,2011,vol. 47,p. 2679 - 2681

10
[ 25016-01-7 ]
[ 81224-16-0 ]

Reference： [1]Journal of Heterocyclic Chemistry,1981,vol. 18,p. 1373 - 1377

11
[ 25016-01-7 ]
[ 144649-99-0 ]

Yield	Reaction Conditions	Operation in experiment
97%	With formic acid; hydroxylamine hydrochloride; sodium acetate; for 15h;Reflux;	5-Bromo-2-methoxybenzaldehyde (20.00 mmol, 4.30 g) was dissolved in formic acid (20 mL) and treated with hydroxylamine hydrochloride (21.00 mmol, 1.45 g) and sodium acetate (26.00 mmol, 2.13 g). The reaction mixture was heated at reflux for 15 hours. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate (250 mL). The organics were washed with saturated sodium bicarbonate solution (2.x.200 mL) and then dried with MgSO4. The organics were filtered and evaporated under reduced pressure to yield the title compound as a white solid. Yield=4.10 g, 97percent. Analytical LCMS method 2, retention time 6.07 min, M+H=214, 216. 1H NMR: (CDCl3) delta: 7.66-7.61 (m, 2H), 6.87 (d, 1H), 3.92 (s, 3H).
	With sodium hydroxide; formic acid; hydroxylamine hydrochloride; sodium formate;	EXAMPLE I A mixture of 6.45 g 5-bromo-o-anisaldehyde, 2.2 g of hydroxylamine hydrochloride, 4.1 g of sodium formate and 20 mL formic acid were heated at 100° C. with stirring for 1 h. The reaction mixture was poured onto ice water and the mixture was made basic by the careful addition of 50percent sodium hydroxide. The product was extracted with ether, the ether extracts were dried over magnesium sulfate and the solvent was removed in vacuo. The residue was crystallized from ether/hexane to afford 5-bromo-2-methoxybenzonitrile.
	With sodium hydroxide; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; acetic acid;	EXAMPLE I STR31 A mixture of 5-Bromo-o-anisaldehyde (6.45 g), hydroxylamine hydrochloride (2.2 g), sodium acetate (4.1 g) and acetic acid (20 mL) was heated at 100° C. with stirring for 1 h. Acetic anhydride was added (20 mL) and the mixture was refluxed for 8 h. The reaction mixture was poured onto ice water and the mixture was made basic by the careful addition of 50percent sodium hydroxide. The product was extracted with ether, the ether extracts were dried over magnesium sulfate and the solvent was removed in vacuo. The residue was crystallized from ether/hexane to afford 5-Bromo-2-methoxy-benzonitrile.

With sodium hydroxide; hydroxylamine hydrochloride; sodium acetate; acetic anhydride; acetic acid;

EXAMPLE I STR21 A mixture of 5-Bromo-o-anisaldehyde (6.45 g), hydroxylamine hydrochloride (2.2 g), sodium acetate (4.1 g) and acetic acid (20 mL) was heated at 100° C. with stirring for 1 h. Acetic anhydride was added (20 mL) and the mixture was refluxed for 8 h. The reaction mixture was poured onto ice water and the mixture was made basic by the careful addition of 50percent sodium hydroxide. The product was extracted with ether, the ether extracts were dried over magnesium sulfate and the sovent was removed in vacuo. The residue was crystallized from ether/hexane to afford 5-Bromo-2-methoxybenzonitrile.

Reference： [1]Science China Chemistry,2015,vol. 58,p. 747 - 750
[2]Patent: US2009/247519,2009,A1 .Location in patent: Page/Page column 143
[3]Patent: US2003/18025,2003,A1
[4]Patent: US5633376,1997,A
[5]Patent: US5159083,1992,A

12
[ 4885-02-3 ]
[ 323-09-1 ]
7-fluoro-1-naphthaldehyde [ No CAS ]
[ 25016-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	titanium tetrachloride; In dichloromethane;	PREPARATION 19 7-Fluoro-1-naphthaldehyde and 2-Fluoro-1-naphthaldehyde By the method of Preparation 1, <strong>[323-09-1]2-fluoronaphthalene</strong> (10 g., 0.068 mole) in 200 ml. of methylene chloride was reacted with titanium tetrachloride (25.5 g., 14.7 ml. 0.136 mole) and 1,1-dichloromethyl methyl ether (10.1 g., 0.088 mole). The resulting crude product (11 g.) was first recrystallized from hexane to yield 7-fluoro-1-naphthaldehyde [2.5 g., m.p. 95-96 C., Rf 0.25 (1:1 chloroform:hexane)].

Reference： [1]Patent: US4367234,1983,A

13
[ 109-97-7 ]
[ 25016-01-7 ]
[ 5736-88-9 ]
Por(Br) [ No CAS ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 6350 - 6362

14
[ 588-96-5 ]
[ 25016-01-7 ]
[ 1221506-20-2 ]

Reference： [1]Journal of Medicinal Chemistry,2010,vol. 53,p. 3247 - 3261

15
[ 7504-94-1 ]
[ 25016-01-7 ]
[ 1333991-76-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5266 - 5269

16
[ 25016-01-7 ]
[ 16740-73-1 ]

Reference： [1]Drug Metabolism and Disposition,2012,vol. 40,p. 2002 - 2008,7

17
[ 184970-28-3 ]
[ 25016-01-7 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 3402 - 3410

18
[ 80866-82-6 ]
[ 25016-01-7 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In dimethyl sulfoxide; ethyl acetate; at 0 - 20℃;Inert atmosphere;	General procedure: To a solution of alcohol (2mmol) in DMSO (2 mL), was added at 0 C T3P (1.0 mmol, 50 % solution in ethyl acetate) and the resulting reaction mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC, after the completion of the reaction, the solvent was removed under reduced pressure.The crude product was taken in toluene, was added 3 A molecular sieves (200 mg), amine 1 (1.0 mmol) acetic acid (0.5 equiv)was added and stirred further for 1-2 h. After completion ofthe reaction, the mixture was diluted with water (20 mL) and neutralized with 10 % NaHCO3 solution. The product was extracted with ethyl acetate (10 mL) and the combined organic phase was washed with water (10 mL) and brine solution. The organic phase was dried over anhydrous Na2SO4. The solvent was dried under reduced pressure to afford a crude product, (3a-3q) which was purified on silica gel using ethyl acetate and petroleum ether.

Reference： [1]RSC Advances,2014,vol. 4,p. 48777 - 48782
[2]Asian Journal of Chemistry,2019,vol. 31,p. 403 - 409

19
[ 95-23-8 ]
[ 25016-01-7 ]
(E)-5-((5-bromo-2-methoxybenzylidene)amino)-1H-benzo[d]imidazol-2(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With acetic acid; In isopropyl alcohol;Reflux; Inert atmosphere;	5-Bromo-2-methoxybenzaldehyde (0.1 g, 0.47 mmol), 5-Amino-2-benzimidazolinone (0.06 g, 0.39 mmol), and isopropyl alcohol (2 mL) were stirred at room temperature under N2. Acetic acid (0.07 mL) was added drop-wise, and the mixture was refluxed overnight. The reaction mixture was filtered, washed with CH2Cl2, MeOH, and dried to give 4 (0.12 g, 0.35 mmol, 90.3%) as a light brown powder. 1H NMR (DMSO, 300 MHz) delta 10.69 (s, 2H), 8.79 (s, 1H), 8.07 (s, 1H), 7.65 (d, 1H, J=7.8 Hz), 7.15 (d, 1H, J=7.8 Hz), 6.93 (s, 1H), 6.99-6.83 (m, 2H), 3.90 (s, 3H); 13C NMR (DMSO, 500 MHz) delta 158.86, 156.24, 151.83, 145.29, 135.39, 131.17, 129.55, 129.27, 126.92, 115.51, 115.35, 113.21, 109.42, 101.79, 56.92. Rf=0.44 (CH2Cl2/MeOH 9:1)
90.3%	With acetic acid; In isopropyl alcohol;Inert atmosphere; Reflux;	5-bromo-2-methoxybenzaldehyde (0.1g, 0.47mmol), 5-amino-2-benzimidazolyl BBIT (0.06g, 0.39mmol) and isopropyl alcohol (2mL) and N2was stirred at room temperature It was.Followed by dropwise addition of acetic acid (0.07mL) and the mixture was refluxed overnight and the mixture.Filtering the reaction mixture, CH2Cl2, dried, washed with MeOH, the compound as a light brown powder4was obtained (0.12g, 0.35mmol, 90.3%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 4659 - 4663
[2]Patent: KR101639289,2016,B1 .Location in patent: Paragraph 0147-0150

20
[ 25016-01-7 ]
[ 166530-78-5 ]

Yield	Reaction Conditions	Operation in experiment
		A solution of 5-bromo-2-methoxybenzaldehyde 11 (1 g, 4.65 mmol) and hydroxylaminehydrochloride (388 mg, 5.58 mmol) in ethanol (2.8 mL) was stirred for 1 h at room temperature.Subsequently, hydrochloric acid (12 M, 1.6 mL, 18.6 mmol) and zinc dust (760 mg, 11.62 mmol)slowly were added to the solution and the mixture was stirred at room temperature for 15 min. Asolution of ammonia (30%, 2.8 mL) and sodium hydroxide (6 M, 2.8 mL) was added dropwise tothe resulting slurry, and the mixture was stirred at room temperature for 15 min. Then, theresultant solution was extracted with CH2Cl2, dried over anhydrous sodium sulfate, and filtered.The solvent was removed under vacuum to afford the crude benzyl amine. The residue wasdissolved in CH2Cl2 (20 mL) which was then followed by the addition of Boc2O (1.52 g, 7.0mmol) and Et3N (710 mg, 7.0 mmol) at rt, the mixture was stirred for 2 h. After completion ofthe reaction, water was added into it, organic phase was separated and aqueous layer wasextracted with CH2Cl2 (3 × 20 mL). Organic phases were combined, washed with brine, driedover anhyd.Na2SO4 and concentrated to get crude boc-amine, which was then purified by columnchromatography (100-200 mesh size) using ethyl acetate:pet ether (1:9) as an eluent to affordpure boc-protected benzyl amine 12 (1.47 g).

Reference： [1]Synlett,2016,vol. 27,p. 1339 - 1343

21
[ 220210-56-0 ]
[ 25016-01-7 ]
3'-formyl-4'-methoxybiphenyl-3-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 692 - 696

22
[ 850568-54-6 ]
[ 25016-01-7 ]
3'-formyl-4'-methoxybiphenyl-4-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 692 - 696

23
[ 4481-62-3 ]
[ 25016-01-7 ]
2-(5-bromo-2-methoxybenzylidene)betulonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%		General procedure: To synthesize compounds 15a-o, compound 7 (1 equiv) was dissolved in dry THF and NaH (1.2 equiv) was added to it at 0C. After 10min, respective aldehyde (1.5 equiv) was added to reaction mixture. The reaction mixture was stirred at room temperature for 1.5-2h till the completion (monitored by TLC analysis) [25]. Workup of the reaction was done by diluting the reaction mixture with ice-cold water and extracting it with ethyl acetate (3 times). The combined organic layers were dried over sodium sulphate and concentrated on rotavapour. The crude product obtained was purified by column chromatography on silica gel 60-120 mesh with EtoAc: hexane (1: 10) as the eluent to afford the desired pure products 15a-o in 90-93% yield. The spectral data of all the derivatives 15a-o are given below.

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 135,p. 517 - 530

24
[ 1073-39-8 ]
[ 25016-01-7 ]
(5-bromo-2-methoxyphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		To a mixture of <strong>[1073-39-8]3-bromobicyclo[4.2.0]octa-1,3,5-triene</strong> (80 g, 437.05 mmol, 1.05 equiv) in THF (800 mL) was added n-BuLi (2.5M in hexane, 180 mL, 1.10 equiv) dropwise at -78C, and the reaction mixture was stirred at - 78C for 30 min. 5-Bromo-2-methoxybenzaldehyde (89.5 g, 416.19 mmol, 1.00 equiv) in THF (800 mL) was then added to the solution dropwise at -78C. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (10: 1 PE/EA) to yield (5-bromo-2- methoxyphenyl)(1,2-dihydrocyclobutabenzen-4-yl)methanol as a colorless oil.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 1182 - 1187
[2]Patent: WO2018/89449,2018,A1 .Location in patent: Page/Page column 67

25
[ 1994-13-4 ]
[ 25016-01-7 ]
3,3′-((5′′-bromo-2′′-methoxyphenyl)methylene)bis(6-fluoro-4-hydroxy-2H-chromen-2-one) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With tetraethylammonium bromide; In water; for 2h;Reflux;	General procedure: 6-Fluoro-4-hydroxy /6-chloro-4-hydroxy /4-hydroxy coumarin(1 mmol), and a variety of aromatic aldehydes (0.5 mmol), as well as 10 mol% of tetraethylammonium bromide (TEAB) were dissolved indistilled water (15 mL) in a 100 mL round-bottommed flask. The reactionmixture was refluxed for 2 h. Periodic TLC was taken to check theprogress of reaction. Resulting precipitates were filtered, and washedwith distilled water. This afforded products 1-44 in high yields.

Reference： [1]Bioorganic Chemistry,2019,vol. 91

26
[ 25016-01-7 ]
[ 41100-52-1 ]
(1R,3R,5S,7R)-N-(5-bromo-2-methoxybenzyl)-3,5-dimethyladamantan-1-amine [ No CAS ]

Reference： [1]ACS Medicinal Chemistry Letters,2019,vol. 10,p. 1140 - 1147

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere