[ CAS No. 1195-44-4 ] {[proInfo.proName]}

Name: 1195-44-4|1-Chloro-4-(methoxymethyl)benzene|95%
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Quality Control of [ 1195-44-4 ]

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Product Details of [ 1195-44-4 ]

CAS No. :	1195-44-4	MDL No. :	MFCD22054452
Formula :	C₈H₉ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YOZIDEHIYNEGMS-UHFFFAOYSA-N
M.W :	156.61	Pubchem ID :	11983955
Synonyms :

Safety of [ 1195-44-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1195-44-4 ]

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

Downstream synthetic route of [ 1195-44-4 ]

[ 1195-44-4 ] Synthesis Path-Downstream 1~50

1
[ 1195-44-4 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
86%	With nitric acid In dichloromethane at 20℃; for 1h;
	With tetrachloromethane; bromine Irradiation;
	With Cu(NO₃)2-SiO₂ In 2,2,4-trimethylpentane for 1h; Heating; Yield given;

89.2 - 91 %Chromat.	With sodium bromate; acetic acid at 80 - 90℃; for 1.5 - 8h;	10; 16 In the same manner as in Example 3, the operation was conducted, except that 0.63 g (4 mmols) of p-chlorobenzyl methyl ether was used in place of m-methoxybenzyl alcohol and also 0.2g (1.35 mmols) of sodium bromate was used. With respect to the components in the reaction solution, the intended p-chlorobenzaldehyde was produced in an area ratio, as determined by gas chromatography, of 91.0%.Example 3 (An embodiment of the invention described in the above embodiment [1]): Production of m-methoxybenzaldehyde In a 15 ml test tube type reaction vessel equipped with a magnetic stirrer and a reflux condenser, 0.55 g (4 mmols) of m-methoxybenzyl alcohol, 0.18 g (1.2 mmols) of sodium bromate and 2 ml (34.8 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 90°C for 1.5 hours. Along with the progress of the reaction, a small amount of bromine was produced. After the completion of the reaction, bromine completely disappeared.Example 16 (An embodiment of the invention described in the above embodiment [1]): Production of p-chlorobenzaldehyde In a 100 ml four-necked flask equipped with a magnetic stirrer, a reflux condenser and a thermometer, 31.3 g (200 mmols) of p-chlorobenzyl methyl ether, 10.0 g (67 mmols) of sodium bromate and 40 ml (696 mmols) of acetic acid were charged, and then the resultant mixture was stirred at 75°C for 8 hours. With the processing of the reaction, a small amount of bromine was produced and the temperature of the reaction solution was raised to 80°C. After the completion of the reaction, bromine completely disappeared. After recovering 28 m of acetic acid under reduced pressure, the resulting reaction solution was cooled to room temperature and 100 ml of water was added. An aqueous 24% sodium hydroxide solution was added by several portions so as not to raise the liquid temperature until the pH is adjusted to 11 or higher. The resulting product was extracted twice with 100 ml of ethyl acetate and the ethyl acetate phase was washed with saturated saline. The ethyl acetate phase was dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure to obtain 29.0 g of a solid. With respect to the components in the solid, the intended p-chlorobenzaldehyde was produced in an area ratio, as determined by gas chromatography, of 89.2%.
	With tert.-butylnitrite; oxygen; 2,3-dicyano-5,6-dichloro-p-benzoquinone In monoethylene glycol diethyl ether at 140℃; for 3.5h;

Reference： [1]Strazzolini, Paolo; Runcio, Antonio [European Journal of Organic Chemistry, 2003, # 3, p. 526 - 536]
[2]Markees [Journal of Organic Chemistry, 1958, vol. 23, p. 1490]
[3]Nishiguchi, Takeshi; Bougauchi, Masahiro [Journal of Organic Chemistry, 1990, vol. 55, # 21, p. 5606 - 5609]
[4]Current Patent Assignee: KUMIAI CHEMICAL INDUSTRY CO LTD - EP1661877, 2006, A1 Location in patent: Page/Page column 13; 15-16
[5]Location in patent: scheme or table Shen, Zhenlu; Dai, Jialiang; Xiong, Jie; He, Xijun; Mo, Weimin; Hu, Baoxiang; Sun, Nan; Hu, Xinquan [Advanced Synthesis and Catalysis, 2011, vol. 353, # 16, p. 3031 - 3038]

2
[ 124-41-4 ]
[ 104-83-6 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
65%

Reference： [1]Imrie, C.; Modro, T. A.; Rohwer, E. R.; Wagener, C. C. P. [Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5643 - 5649]
[2]Markees [Journal of Organic Chemistry, 1958, vol. 23, p. 1490] Mamedow et al. [Zhurnal Obshchei Khimii, 1964, vol. 34, p. 3583,3585; engl. Ausg. S. 3632, 3634] Gilman; McNinch [Journal of Organic Chemistry, 1961, vol. 26, p. 3723,3728]

3
[ 67-66-3 ]
[ 1195-44-4 ]
1-Chloro-4-(2,2-dichloro-2-methoxy-ethyl)-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; 2,4,6-tri-tert-butylphenoxol; benzyltrimethylammonium chloride In dichloromethane for 6h; Heating;

Reference： [1]Goh,S.-H. et al. [Australian Journal of Chemistry, 1975, vol. 28, p. 381 - 384]

4
[ 110-05-4 ]
[ 1195-44-4 ]
[ 22089-62-9 ]

Reference： [1]Goh,S.H. [Journal of Organic Chemistry, 1972, vol. 37, p. 3098 - 3101]

5
[ 1195-44-4 ]
[ 26434-37-7 ]

Yield	Reaction Conditions	Operation in experiment
	With di-tert-butyl peroxide

Reference： [1]Huang,R.L. et al. [Journal of the Chemical Society C: Organic, 1969, p. 2522 - 2527]

6
[ 1195-44-4 ]
1,2-dimethoxy-1,2-di(4-chlorophenyl)ethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-tert-butyl peroxide

Reference： [1]Huang,R.L. et al. [Journal of the Chemical Society C: Organic, 1969, p. 2522 - 2527]

7
[ 1878-66-6 ]
[ 52449-43-1 ]
[ 1195-44-4 ]
[ 3395-81-1 ]
[ 104-88-1 ]
[ 873-76-7 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 1843 - 1852

8
[ 67-56-1 ]
[ 106-43-4 ]
[ 1195-44-4 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; tetraethylammonium tosylate 1.) electrochemical anodic oxidation, AcOH, 2.) RT, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Nishiguchi, Ikuzo; Hirashima, Tsuneaki [Journal of Organic Chemistry, 1985, vol. 50, # 4, p. 539 - 541]

9
[ 67-56-1 ]
[ 130774-55-9 ]
[ 34642-42-7 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	With 2,6-dimethylpyridine at 32℃;

Reference： [1]Braverman, Samuel; Manor, Haim [Phosphorus, Sulfur and Silicon and the Related Elements, 1990, vol. 53, # 1-4, p. 357 - 365]

10
[ 67-56-1 ]
[ 17876-99-2 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
72%	With tetraethylammonium tosylate electrolysis, undivided cell, carbon rod electrodes;

Reference： [1]Yoshida, Jun-ichi; Murata, Toshiki; Isoe, Sachihiko [Tetrahedron Letters, 1986, vol. 27, # 29, p. 3373 - 3376]

11
[ 106-39-8 ]
[ 27490-32-0 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	In N,N,N,N,N,N-hexamethylphosphoric triamide at 80℃; for 20h;

Reference： [1]Kosugi, Masanori; Sumiya, Takashi; Ogata, Toshimi; Sano, Hiroshi; Migita, Toshihiko [Chemistry Letters, 1984, p. 1225 - 1226]

12
[ 691-38-3 ]
4-Chloro-benzyl-diazene [ No CAS ]
[ 1195-44-4 ]
1-Chloro-4-((1R,2R)-2-isopropyl-3-methyl-cyclopropyl)-benzene [ No CAS ]
1-Chloro-4-((1R,2S)-2-isopropyl-3-methyl-cyclopropyl)-benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With methanol In 1,4-dioxane at 10℃; Irradiation; Yield given. Yields of byproduct given;

Reference： [1]Tomoika, H.; Ozaki, Y.; Izawa, Y [Tetrahedron, 1985, vol. 41, # 21, p. 4987 - 4994]

13
[ 106-43-4 ]
[ 1195-44-4 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrafluoroborate; sulfuric acid 1.) electrochemical anodic oxidation, AcOH, MeOH, 2.) RT, 3 h; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Nishiguchi, Ikuzo; Hirashima, Tsuneaki [Journal of Organic Chemistry, 1985, vol. 50, # 4, p. 539 - 541]

14
[ 1195-44-4 ]
[ 1126-46-1 ]
[ 74-11-3 ]

Yield	Reaction Conditions	Operation in experiment
	With ruthenium tetroxide In water; acetone at 30℃;

Reference： [1]Bakke, Jan M.; Froehaug, Astrid E. [Acta Chemica Scandinavica, 1995, vol. 49, # 8, p. 615 - 622]

15
[ 873-76-7 ]
[ 74-88-4 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: para-Chlorobenzyl alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.25h; Inert atmosphere; Stage #2: methyl iodide In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere;
82%	With potassium hydroxide In dimethyl sulfoxide at 20℃;	1 Example 1; Protection of 4-chlorobenzyl alcohol; Dimethyl sulfoxide (300 mL) was placed into a 1 L round bottom flask under argon. The KOH (78.7 g, 1402 mmol) was then added and this was stirred for 15 minutes until most of the KOH dissolved. The 4-chlorobenzyl alcohol (50 g, 350.65 mmol) and then iodomethane (99.5 g, 701.3 mmol) were then added. The reaction was stirred at room temperature under argon overnight. Cyclohexane (300 mL) was then added and this was stirred for 1 hour. The layers were separated and the cyclohexane was washed twice with 50% brine solution. The organic layer was collected, dried (MgSO4) and concentrated in vacuo to give a yellowish oil, which was purified by distillation to give a clear and colorless oil in 82% yield.
	With sodium hydride In tetrahydrofuran for 2h; Ambient temperature;

Reference： [1]Finney, Laura C.; Mitchell, Lorna J.; Moody, Christopher J. [Green Chemistry, 2018, vol. 20, # 10, p. 2242 - 2249]
[2]Current Patent Assignee: XEROX CORP - US2008/255389, 2008, A1 Location in patent: Page/Page column 10
[3]Bakke, Jan M.; Froehaug, Astrid E. [Acta Chemica Scandinavica, 1995, vol. 49, # 8, p. 615 - 622]

16
[ 67-56-1 ]
[ 65622-34-6 ]
[ 106-43-4 ]
[ 1195-44-4 ]
[ 5216-35-3 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,3,5-trimethyl-benzene; 1-Cyanonaphthalene In acetonitrile at 20℃; Irradiation; other 4,4'-disubstituted dibenzyl ketones; var. donor-acceptor systems;

Reference： [1]Ishiguro, Katsuya; Nakano, Tomoharu; Shibata, Hiroki; Sawaki, Yasuhiko [Journal of the American Chemical Society, 1996, vol. 118, # 31, p. 7255 - 7264]

17
[ 6214-19-3 ]
[ 60812-71-7 ]
[ 1195-44-4 ]
[ 6140-09-6 ]

Yield	Reaction Conditions	Operation in experiment
	In dimethylsulfoxide-d6 at 30.3℃;

Reference： [1]Fountain; White, Robert D.; Patel, Kamlesh D.; New, Dallas G.; Xu, YuBo; Cassely, Aaron J. [Journal of Organic Chemistry, 1996, vol. 61, # 26, p. 9434 - 9436]

18
[ 1195-44-4 ]
[ 630-19-3 ]
[ 6013-94-1 ]
1-(4-Methoxymethyl-phenyl)-2,2-dimethyl-propan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With naphthalene; lithium 1.) THF, -80 deg C, 4 h, 2.) THF, 10 min; Yield given. Multistep reaction. Yields of byproduct given;

Reference： [1]Azzena, Ugo; Carta, Simonetta; Melloni, Giovanni; Sechi, Alessandra [Tetrahedron, 1997, vol. 53, # 47, p. 16205 - 16212]

19
[ 1195-44-4 ]
C₈H₈⁽²⁾HClO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With water-d2; sec.-butyllithium 1.) THF, cyclohexane, -80 deg C, 4 h, 2.) THF, cyclohexane, 10 min; Yield given. Multistep reaction;

Reference： [1]Azzena, Ugo; Pilo, Luciano; Sechi, Alessandra [Tetrahedron, 1998, vol. 54, # 40, p. 12389 - 12398]

20
[ 1195-44-4 ]
[ 100-52-7 ]
1-(4-chlorophenyl)-2-hydroxy-2-phenylethyl methyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sec.-butyllithium 1.) THF, cyclohexane, -80 deg C, 4 h, 2.) THF, cyclohexane, 10 min; Yield given. Multistep reaction;

Reference： [1]Azzena, Ugo; Pilo, Luciano; Sechi, Alessandra [Tetrahedron, 1998, vol. 54, # 40, p. 12389 - 12398]

21
[ 1195-44-4 ]
[ 630-19-3 ]
1-(4-chlorophenyl)-2-hydroxy-3,3-dimethylbutyl methyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sec.-butyllithium 1.) THF, cyclohexane, -80 deg C, 4 h, 2.) THF, cyclohexane, 10 min; Yield given. Multistep reaction;

Reference： [1]Azzena, Ugo; Pilo, Luciano; Sechi, Alessandra [Tetrahedron, 1998, vol. 54, # 40, p. 12389 - 12398]

22
[ 56-23-5 ]
[ 1195-44-4 ]
[ 7726-95-6 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	Irradiation;

Reference： [1]Markees [Journal of Organic Chemistry, 1958, vol. 23, p. 1490]

23
[ 1445-45-0 ]
[ 873-76-7 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
80%	With iodine at 20℃; for 0.583333h;

Reference： [1]Kumar; Anjaneyulu; Joyasawal, Sipak; Pawan Chakravarthy; Naveen Kumar; Yadav [Journal of the Indian Chemical Society, 2007, vol. 84, # 2, p. 189 - 192]

24
[ 873-76-7 ]
[ 149-73-5 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With iodine at 20℃; for 0.5h;

Reference： [1]Kumar; Anjaneyulu; Joyasawal, Sipak; Pawan Chakravarthy; Naveen Kumar; Yadav [Journal of the Indian Chemical Society, 2007, vol. 84, # 2, p. 189 - 192]

25
[ 873-76-7 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: SOCl₂ 2: 65 percent

Reference： [1]Imrie, C.; Modro, T. A.; Rohwer, E. R.; Wagener, C. C. P. [Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5643 - 5649]

26
[ 74-11-3 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LAH 2: SOCl₂ 3: 65 percent

Reference： [1]Imrie, C.; Modro, T. A.; Rohwer, E. R.; Wagener, C. C. P. [Journal of Organic Chemistry, 1993, vol. 58, # 21, p. 5643 - 5649]

27
[ 1195-44-4 ]
[ 104-88-1 ]
[ 623-03-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bromate; ammonia In water at 90℃; for 4h;	20 Into a 15 ml, test tube-shaped reactor equipped with a magnetic stirrer and a reflux condenser were added 0.31 g (2 mmol) of p-chlorobenzyl methyl ether, 0.31 g (2.2 mmol) of p-chlorobenzaldehyde, 0.33 g (2.2 mmol) of sodium bromate, 2 ml (34.8 mmol) of acetic acid and 0.4 g (5.9 mmol) of 25% aqueous ammonia, followed by stirring at 90°C for 4 hours. The reaction mixture contained, as a product, 94.7% (in terms of areal ratio of gas chromatography) of p-chlorobenzonitrle, and p-chlorobenzyl methyl ether remained by 4.1%. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of p-chlorobenzonitrile was confirmed to be 137.

Reference： [1]Current Patent Assignee: KUMIAI CHEMICAL INDUSTRY CO LTD - EP1555257, 2005, A1 Location in patent: Page/Page column 29

28
[ 1195-44-4 ]
[ 623-03-0 ]
[ 1126-46-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bromate; ammonia; water at 90℃; for 15h;	13 An operation was conducted in the same manner as in Example 8 except that p-nitrobenzaldehyde was replaced by 0.31 g (2 mmol) of p-chlorobenzyl methyl ether and 25% aqueous ammonia was used by 0.31 g (4.6 mmol). The reaction mixture contained, as components, 94.0% (in terms of areal ratio of gas chromatography) of p-chlorobenzonitrile, 2.3% of p-chlorobenzyl methyl ether and 3.7% of methyl p-chlorobenzoate. Gas mass chromatography (GC-MS) was conducted and the molecular ion peak [M+] of p-chlorobenzonitrile was confirmed to be 137.

Reference： [1]Current Patent Assignee: KUMIAI CHEMICAL INDUSTRY CO LTD - EP1555257, 2005, A1 Location in patent: Page/Page column 27

29
[ 67-56-1 ]
[ 104-83-6 ]
[ 1195-44-4 ]
[ 873-76-7 ]

Yield	Reaction Conditions	Operation in experiment
	In water; acetonitrile at 75℃;

Reference： [1]Bentley, T. William; Koo, In Sun; Choi, Hojune; Llewellyn, Gareth [Journal of Physical Organic Chemistry, 2008, vol. 21, # 3, p. 251 - 256]

30
[ 1195-44-4 ]
[ 62-53-3 ]
[ 918962-75-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium t-butanolate In toluene at 110℃; for 3h;	1 Buchwald Reaction: To a 500 mL 3-necked round bottom flask equipped with a mechanical stirrer, argon inlet, thermometer and reflux condenser was placed (1,3-diisopropylimidazol-2-ylidene)(3-chloropyridyl) palladium(II) dichloride (2.19 g, 3.2 mmol) and was dissolved in toluene (50 mL) under argon. Then aniline (10 g, 107.4 mmol), the protected 4-chlorobenzyl alcohol (50.30 g, 322.2 mmol) and then sodium tert-butoxide (20.6 g, 214.8 mmol) were added. The reaction was stirred under argon at 110° C. until the reaction was complete, usually 3 hours. The reaction was then cooled and then washed twice with a 50% aqueous brine solution. The organic layer was collected, dried (MgSO4) and then treated with 20 g each of an acidified clay and alumina at 100° C. for 30 minutes. The solids were filtered and the filtrate was concentrated under reduced pressure to produce a light yellow oil in 75% yield. NMR confirmed that the desired triarylamine, 4-(methoxymethyl)-N-(4-(methoxymethyl)phenyl)-N-phenylaniline was obtained.

Reference： [1]Current Patent Assignee: XEROX CORP - US2008/255389, 2008, A1 Location in patent: Page/Page column 10

31
[ 1195-44-4 ]
[ 122-39-4 ]
[ 937729-45-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium t-butanolate In xylene at 130℃;	2 Example 2 To a 500 mL 3-necked round bottom flask equipped with a mechanical stirrer, argon inlet, thermometer and reflux condenser was placed palladium acetate (0.398 g, 1.773 mmol), cytop-216 (0.493 g, 1.773 mmol) and was dissolved in xylene (150 mL) under argon. Then diphenylamine (10 g, 59.1 mmol), the protected 4-bromobenzyl alcohol (14.26 g, 70.9 mmol) and then sodium tert-butoxide (8.52 g, 89 mmol) were added. The reaction was stirred under argon at 130° C. until the reaction was complete. The reaction was then cooled and then washed twice with a 50% aqueous brine solution. The organic layer was collected, dried (MgSO4) and then treated with 30 g each of an acidified clay and alumina at 100° C. for 30 minutes. The solids were filtered and the filtrate was concentrated under reduced pressure to produce an off white solid in good yield. NMR would confirm that the desired triarylamine 4-(methoxymethyl)-N,N-diphenylaniline was obtained.

Reference： [1]Current Patent Assignee: XEROX CORP - US2008/255389, 2008, A1 Location in patent: Page/Page column 10

32
[ 31469-15-5 ]
[ 1195-44-4 ]
[ 14305-27-2 ]

Yield	Reaction Conditions	Operation in experiment
99 %Spectr.	Stage #1: 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene; 4-chlorobenzyl methyl ether With indium(III) bromide; trimethylsilyl bromide In dichloromethane at 20℃; for 2h; Stage #2: With water; sodium hydrogencarbonate Saturated solution;

Reference： [1]Location in patent: experimental part Nishimoto, Yoshihiro; Saito, Takahiro; Yasuda, Makoto; Baba, Akio [Tetrahedron, 2009, vol. 65, # 28, p. 5462 - 5471]

33
[ 1195-44-4 ]
[ 3753-18-2 ]

Yield	Reaction Conditions	Operation in experiment
	With zinc In 1-methyl-pyrrolidin-2-one at 20 - 70℃; Inert atmosphere;	15 To a glass reaction container equipped with a cooling apparatus, 15.3 mg of nickel bromide, 19.2 mg of 5-trimethylsilyl-2,2'-bipyridine and 91.6 mg of zinc powder were added in an atmosphere of nitrogen at room temperature. To the obtained mixture, 109. 6 mg of 1-chloro-4-(methoxymethyl) benzene and 5 mL of N-methyl-2-pyrrolidone were added. The obtained mixture was reacted at 70°C for 2 hours to obtain a reaction mixture containing 4,4'-bis(methoxymethyl)biphenyl. The yield of 4,4'-bis(methoxymethyl)biphenyl was 67.8 mg.
	With zinc In 1-methyl-pyrrolidin-2-one at 20 - 70℃; Inert atmosphere;	19 To a glass reaction container equipped with a cooling apparatus, 15.3 mg of nickel bromide, 25.2 mg of 5,5'-bis(trimethylsilyl)-2,2'-bipyridine and 91.6 mg of zinc powder were added under an atmosphere of nitrogen at room temperature. To the obtained mixture, 109.6 mg of 1-chloro-4-(methoxymethyl)benzene and 5 mL of N-methyl-2-pyrrolidone were added at room temperature. The obtained mixture was reacted at 70°C for 2 hours to obtain a reaction mixture containing 4,4'-bis(methoxymethyl)biphenyl. The yield of 4,4'-bis(methoxymethyl)biphenyl was 63.0 mg.

Reference： [1]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - EP2172470, 2010, A1 Location in patent: Page/Page column 43
[2]Current Patent Assignee: SUMITOMO CHEMICAL COMPANY LIMITED; Sumitomo Chemical (w/o Dongwoo Fine-Chem) - EP2192124, 2010, A1 Location in patent: Page/Page column 44

34
[ 67-56-1 ]
[ 622-95-7 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With iron(II) sulfate at 75℃; for 12h;
	With N-doped reduced graphene oxide (MR-60) at 80℃; for 12h; Green chemistry;

Reference： [1]Location in patent: experimental part Joshi, Girdhar; Adimurthy, Subbarayappa [Synthetic Communications, 2011, vol. 41, # 5, p. 720 - 728]
[2]Singh, Ajay K.; Basavaraju; Sharma, Siddharth; Jang, Seungwook; Park, Chan Pil; Kim, Dong-Pyo [Green Chemistry, 2014, vol. 16, # 6, p. 3024 - 3030]

35
[ 16881-77-9 ]
[ 104-88-1 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: (dimethoxy)methylsilane; 4-chlorobenzaldehyde With dicarbonyl(pentamethylcyclopentadienyl)(4-methoxyphenyl)iron In dichloromethane for 4h; Inert atmosphere; Irradiation; Schlenk technique; Stage #2: With sodium hydroxide In methanol; water Inert atmosphere; Schlenk technique;	General procedure for the reaction of aromatic aldehydes and analytical data General procedure: In a Schlenk tube under 1 atm of argon, a solution of the substrate (2 mmol, 1 equiv), the precatalyst (0.04 mmol, 0.02 equiv), and the silane (3 mmol, 1.5 equiv) in methylene chloride (15 mL) was irradiated for 4h. After removal of the solvent, methanol (5 mL) and aqueous NaOH solution (2.5 M, 5 mL) were added and the resulting suspension was stirred overnight. Neutralization with aqueous HCl solution (2 M, 30 mL) and brine (20 mL) followed by standard workup gave the desired products as pure yellow oils.

Reference： [1]Argouarch, Gilles; Grelaud, Guillaume; Roisnel, Thierry; Humphrey, Mark G.; Paul, Frédéric [Tetrahedron Letters, 2012, vol. 53, # 37, p. 5015 - 5018]

36
[ 1195-44-4 ]
[ 16002-63-4 ]
[ 7364-23-0 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: 4-chlorobenzyl methyl ether With 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 80℃; for 3h; Inert atmosphere; Stage #2: phenylmagnesium iodide In diethyl ether; 1,2-dichloro-ethane at -20℃; for 3h; Inert atmosphere;
54%	Stage #1: 4-chlorobenzyl methyl ether With 2-azatricyclo[3.3.1.1^3,7]decan-2-ol; [bis-(trifluoroacetoxy)iodo]benzene In 1,2-dichloro-ethane at 50℃; for 15h; Inert atmosphere; Stage #2: phenylmagnesium iodide With 2-azatricyclo[3.3.1.1^3,7]decan-2-ol; [bis-(trifluoroacetoxy)iodo]benzene In diethyl ether; 1,2-dichloro-ethane at -30℃; for 3h; Inert atmosphere;

Reference： [1]Muramatsu, Wataru; Nakano, Kimihiro [Organic Letters, 2014, vol. 16, # 7, p. 2042 - 2045]
[2]Muramatsu, Wataru; Nakano, Kimihiro [Organic Letters, 2015, vol. 17, # 6, p. 1549 - 1552]

37
[ 1195-44-4 ]
[ 106-54-7 ]
[ 6310-31-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With di-tert-butyl peroxide In neat (no solvent) at 120℃; for 24h; Sealed tube;

Reference： [1]Feng; Lv; Lu; Cai [Organic and Biomolecular Chemistry, 2015, vol. 13, # 3, p. 677 - 681]

38
[ 616-38-6 ]
[ 873-76-7 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
78%	With N-butyl-4-methylpyridinium bromide at 170℃; for 2h; Inert atmosphere; Ionic liquid; Green chemistry; chemoselective reaction;	11 4.3. Selective O-methylation of phenols and benzyl alcohol General procedure: A mixture of 1 mmol phenols or benzyl alcohols, 1 mL DMC and 1 mmol of IL was taken in a 10 mL RBF fitted with a reflux condenser and placed in an oil bath. The reaction mixture was heated to 170 °C under nitrogen atmosphere for reaction time indicated in Table 2. On completion of reaction, as monitored by TLC using ethyl acetate and petroleum ether (60-80 °C) as eluent, the crude product was extracted with diethyl ether (5 mL × 3), the ether extract washed with water,dried with anhydrous Na2SO4 and solvent removed by evaporation.The crude product obtained was purified by column chromatography on silica gel column and ethyl acetate-petroleum ether as eluent.

Reference： [1]Das, Pranab Jyoti; Das, Jupitara [Journal of Molecular Liquids, 2015, vol. 209, p. 94 - 98]

39
[ 3395-81-1 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
89%	With C₁₈H₄BCl₃F₈; hydrogen In tetrahydrofuran at 55℃; for 12h;

Reference： [1]Bakos, Mária; Gyömöre, Ádám; Domján, Attila; Soós, Tibor [Angewandte Chemie - International Edition, 2017, vol. 56, # 19, p. 5217 - 5221][Angew. Chem., 2017, vol. 129, # 19, p. 5301 - 5305]

40
[ 104-88-1 ]
[ 149-73-5 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With C₁₈H₄BCl₃F₈; hydrogen In tetrahydrofuran at 55℃; for 84h;

41
[ 1195-44-4 ]
[ 111409-79-1 ]
C₁₉H₂₉ClOSi [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	With silver (II) carbonate; silver hexafluoroantimonate; dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; lithium acetate In 1,2-dichloro-ethane at 100℃; for 20h;

Reference： [1]Tan, Eric; Quinonero, Ophélie; Elena De Orbe; Echavarren, Antonio M. [ACS Catalysis, 2018, vol. 8, # 3, p. 2166 - 2172]

42
[ 1195-44-4 ]
[ 1126-46-1 ]

Yield	Reaction Conditions	Operation in experiment
72%	With oxygen In water at 25℃; for 12h; Irradiation; Green chemistry;
60%	With copper(II) choride dihydrate; oxygen; hydroquinone at 30℃; for 16h; Sealed tube; Irradiation; Green chemistry;

Reference： [1]Jiang, Li-Ya; Ming, Jing-Jing; Wang, Lian-Yue; Jiang, Yuan-Yuan; Ren, Lan-Hui; Wang, Zi-Cheng; Cheng, Wen-Chen [Green Chemistry, 2020, vol. 22, # 4, p. 1156 - 1163]
[2]Finney, Laura C.; Mitchell, Lorna J.; Moody, Christopher J. [Green Chemistry, 2018, vol. 20, # 10, p. 2242 - 2249]

43
[ 1195-44-4 ]
[ 292638-85-8 ]
(E)-methyl 3-(4-acetylphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With C₅₀H₅₈Cl₂N₆Pd; triethylamine; calcium chloride In water; N,N-dimethyl-formamide at 90℃; for 3h;	4.2. Heck-Mizoroki coupling reactions General procedure: A 25 mL RB flask was charged with chloroarene (1.00 mmol),methyl acrylate (0.130 g, 1.50 mmol), triethylamine (0.152 g,1.50 mmol), and DMF (5 mL). A DMF solution of catalysts (0.1,0.01, and 0.001 mol %, Table 1; 0.01 mol %, Table 2) was added tothe aforementioned solution via the syringe. The flask was fittedto a water condenser capped with anhydrous CaCl2 guard tubeand the contents in the flask were simultaneously stirred andheated at 90 C for 3 h. The reaction mixture was cooled and subsequentlypoured into distilled water (300 mL). The product wasextracted with EtOAc (5 50 mL). The organic layer was dried overanhydrous sodium sulfate and concentrated under vacuum to giveoil. The oil was purified by column chromatography on silica gel(n-hexane/EtOAc, 10/0 ?8/2, v/v) to afford coupling products inyields indicated in Tables 1 and 2.

Reference： [1]Elumalai, Palani; Ujjval, Rishabh; Nethaji, Munirathinam; Thirupathi, Natesan [Polyhedron, 2018, vol. 151, p. 313 - 322]

44
[ 1195-44-4 ]
[ 623-03-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; ammonium acetate; oxygen; nitric acid In acetic acid at 50℃; for 20h; Autoclave;	Conversion of Benzyl Ethers into Aryl Nitriles; GeneralProcedure General procedure: The reactions were carried out a ~40 mL, Teflon-lined, stainlesssteelautoclave. AcOH (2 mL), TEMPO (0.25 mmol), HNO3 (0.25mmol), the appropriate benzylic methyl ether (0.5 mmol), andNH4OAc (1.5 mmol) were added sequentially to the autoclave.Subsequently, the autoclave was pressurized to 1 MPa with O2,and the reaction mixture was heated with magnetic stirring at50 °C for 20 h, then cooled to r.t. The mixture was then dilutedwith Et2O (15 mL) and H2O (5 mL), and adjusted to pH 7-8 with2 M aq NaOH. The two layers were separated, and the aqueouslayer was extracted with Et2O (3 × 15 mL). The organic layerswere combined, dried (Na2SO4), filtered, and concentrated to avolume of approximately 3 mL in a rotary evaporator. GC analysisof the concentrated organic phase, with biphenyl or 1,2,4,5-tetramethylbenzene as internal standard, provided the GC yieldof the product. The crude product in the concentrated organicphase from another parallel experiment was purified bycolumn chromatography [silica gel (200-300 mesh), EtOAc-PE].

Reference： [1]Tian, Xinzhe; Ren, Yun-Lai; Ren, Fangping; Cheng, Xinqiang; Zhao, Shuang; Wang, Jianji [Synlett, 2018, vol. 29, # 18, p. 2444 - 2448]

45
[ 1195-44-4 ]
[ 74-11-3 ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,10-ethyliden-3-octyl-7-trifluoromethylalloxazinium chloride; oxygen; trifluoroacetic acid In acetonitrile at 40℃; for 16h; Molecular sieve; Irradiation;

Reference： [1]Zelenka, Jan; Svobodová, Eva; Tarábek, Ján; Hoskovcová, Irena; Boguschová, Veronika; Bailly, Sarah; Sikorski, Marek; Roithová, Jana; Cibulka, Radek [Organic Letters, 2019, vol. 21, # 1, p. 114 - 119]

46
[ 1195-44-4 ]
[ 100-47-0 ]
[ 65608-83-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With iron(III) perchlorate hydrate In neat (no solvent) at 100℃; for 2h;	Typical experimental procedure for the reaction of nitriles and methyl ethers General procedure: A mixture of nitriles (5 mmol), methyl ethers (6 mmol) and Fe(ClO4)3·H2O (5%mol) was placed in a round bottom flask. Then the reaction mixture was heated at 100 °C for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), 10 ml water was added into reaction system and extracted with ethyl acetate (3 × 20 ml). The organic layers were collected, combined, washed with water (3 × 20 ml), dried over anhydrous Na2SO4, and concentrated under vacuum. The pure products (1a-1k and 2a-2p) were obtained by directly passing through a silica gel (200-300 mesh) column using petroleum ether/ethyl acetate (10:1-5:1).

Reference： [1]Yin, Guibo; Yan, Bin; Chen, Junqing; Ji, Min [Journal of the Iranian Chemical Society, 2019, vol. 16, # 6, p. 1355 - 1363]

47
[ 1195-44-4 ]
[ 62-53-3 ]
[ 6265-91-4 ]

Yield	Reaction Conditions	Operation in experiment
77%	With tert.-butylhydroperoxide; sulfur; potassium iodide In water; dimethyl sulfoxide at 130℃; for 24h; Sealed tube;

Reference： [1]Zhang, Jie; Zhao, Xin; Liu, Ping; Sun, Peipei [Journal of Organic Chemistry, 2019, vol. 84, # 19, p. 12596 - 12605]

48
[ 106-39-8 ]
[ 107-30-2 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: bromochlorobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: chloromethyl methyl ether In tetrahydrofuran at -78 - 0℃; for 2h;	General procedure: General procedure: n-BuLi (1.2 mmol) was added to a THF (6 ml) solution ofaryl bromide (1 mmol) at -78C. After stirring for 1 h at same temperature, a THF solution of MOM-Cl or BOM-Cl (1.1 mmolin 4 ml dry THF) was added dropwise to it. Stirring was continuedfor another 1 h at same temperature and slowlywarmed to 0C over another 1 h and quenched with saturatedaqueous ammonium chloride solution. The organic layerwas separated and aqueous layer was extracted with diethylether. The combined organic layer was dried (Na2SO4) andevaporated. Column chromatographic purification gave thedesired product.

Reference： [1]Panda, Biswajit [Journal of the Indian Chemical Society, 2018, vol. 95, # 8, p. 981 - 985]

49
[ 993-07-7 ]
[ 201230-82-2 ]
C₁₀H₁₁ClO₃ [ No CAS ]
[ 1195-44-4 ]
(2-(4-chlorophenyl)-2-methoxyethoxy)trimethylsilane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 80 %Chromat. 2: 11 %Chromat.	With dicobalt octacarbonyl In benzene at 5℃; for 24h;	General Procedure for the Co2(CO)8-Catalyzed Reactionof Acetals with Hydrosilane and Carbon Monoxide General procedure: In a10-mL reaction flask with an efficient condenser (dry ice/CH3OH) was placed Co2(CO)8 (0.1mmol, 34 mg), after theflask was flashed with CO (1 atm from a stock balloon),HSiMe3 (25mmol, 2.9 mL) was added using a pressure syringeat 25 °C.34 After 5min, benzene (5 mL) and octanal dimethylacetal(8a) (2.5mmol, 435 mg) were added and the mixturewas stirred at 25 °C (bath temperature, under reflux of HSiMe3)for 6 days under CO (1 atm). GC analysis showed that [(2-methoxynonyl)oxy]trimethylsilane (9a) was formed in 86%yield. Kugelrohr distillation (110120°C/10 Torr) gave essentiallypure 9a (410 mg, 67% yield). An analytical sample wasobtained by preparative GC purification (Silicone OV-1)

Reference： [1]Chatani, Naoto; Fujii, Satoru; Kido, Yoichi; Nakayama, Yasuhide; Kajikawa, Yasuteru; Tokuhisa, Hideo; Fukumoto, Yoshiya; Murai, Shinji [Bulletin of the Chemical Society of Japan, 2021, vol. 94, # 1, p. 81 - 90]

50
[ 67-56-1 ]
[ 104-88-1 ]
[ 1195-44-4 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dicobalt octacarbonyl; Tributylphosphine oxide; carbon monoxide; hydrogen In toluene at 120℃; for 24h; Sealed tube; Autoclave; Green chemistry; chemoselective reaction;

Reference： [1]Beller, Matthias; Delolo, Fábio G.; Fessler, Johannes; Gusevskaya, Elena V.; Junge, Kathrin; Neumann, Helfried; dos Santos, Eduardo N. [Chemistry - A European Journal, 2022, vol. 28, # 11]

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P272	Contaminated work clothing should not be allowed out of the workplace.
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Response
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P321
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P332	IF SKIN irritation occurs:
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P337	If eye irritation persists:
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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.
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P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
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P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
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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.
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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

[ CAS No. 1195-44-4 ] {[proInfo.proName]}

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[ 1195-44-4 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 1195-44-4 ]

Aryls

Chlorides

Ethers

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[ 1195-44-4 ]