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Quality Control of [ 7291-00-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 7291-00-1 ]

CAS No. :	7291-00-1	MDL No. :	MFCD00522601
Formula :	C₁₀H₁₃NO₂	Boiling Point :	-
Linear Structure Formula :	(CH₃)2NCOC₆H₄(OCH₃)	InChI Key :	-
M.W :	179.22	Pubchem ID :	-
Synonyms :

Safety of [ 7291-00-1 ]

Signal Word:		Class:
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Application In Synthesis of [ 7291-00-1 ]

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

Downstream synthetic route of [ 7291-00-1 ]

[ 7291-00-1 ] Synthesis Path-Downstream 1~22

1
[ 6086-21-1 ]
[ 7291-00-1 ]
(4-Methoxy-phenyl)-(2-methyl-2H-[1,2,4]triazol-3-yl)-methanone [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,1993,vol. 41,p. 1226 - 1231

2
[ 431-47-0 ]
[ 696-62-8 ]
[ 68-12-2 ]
[ 104-92-7 ]
[ 402-52-8 ]
[ 7291-00-1 ]

Reference： [1]Journal of Fluorine Chemistry,2007,vol. 128,p. 1318 - 1325

3
[ 431-47-0 ]
[ 696-62-8 ]
[ 68-12-2 ]
[ 402-52-8 ]
[ 7291-00-1 ]
[ 100-66-3 ]

Reference： [1]Journal of Fluorine Chemistry,2007,vol. 128,p. 1318 - 1325

4
[ 431-47-0 ]
[ 696-62-8 ]
[ 68-12-2 ]
[ 402-52-8 ]
[ 7291-00-1 ]

Reference： [1]Journal of Fluorine Chemistry,2007,vol. 128,p. 1318 - 1325
[2]Journal of Fluorine Chemistry,2007,vol. 128,p. 1318 - 1325

5
[ 431-47-0 ]
[ 696-62-8 ]
[ 68-12-2 ]
[ 402-52-8 ]
[ 7291-00-1 ]
[ 150-78-7 ]

Reference： [1]Journal of Fluorine Chemistry,2007,vol. 128,p. 1318 - 1325
[2]Journal of Fluorine Chemistry,2007,vol. 128,p. 1318 - 1325

6
[ 7291-00-1 ]
[ 24826-74-2 ]

Reference： [1]Tetrahedron Letters,1983,vol. 24,p. 5465 - 5468

7
[ 39774-26-0 ]
[ 7291-00-1 ]
[ 1186034-25-2 ]

Reference： [1]Synthesis,2009,p. 2179 - 2183

8
[ 7291-00-1 ]
[ 874-90-8 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N,N-dimethyl-4-methoxybenzamide With diisobutylaluminium hydride In tetrahydrofuran; hexane at -78℃; for 1.5h; Inert atmosphere; Stage #2: With ammonia; iodine In tetrahydrofuran; hexane; water at 0 - 20℃; Inert atmosphere;	4.2. Typical experimental procedure for the conversion of N,N-dialkyl amides (1) into nitriles (2) General procedure: To a solution of N,N-dimethyl benzamide (298 mg, 2 mmol) in dry THF (4 mL) was added DIBAL-H (1.04 M in hexane, 2.3 mL, 1.2 equiv) at -78 °C. The mixture was stirred for 1.5 h under an argon atmosphere at from -70 °C to -40 °C slowly. Then, aq NH3 (concentration: 28.0-30.0%, 4 mL) and I2 (762 mg, 3.0 equiv) were added at 0 °C, and the reaction mixture was stirred for 2 h at room temperature. Reaction mixture was poured into saturated aq Na2SO3 solution (10 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was dried over Na2SO4. After removal of the solvent under reduced pressure, the residue was purified by short column chromatography on silica gel (eluent: hexane/ethyl acetate=4:1) to afford benzonitrile in 67% yield (138 mg).Most of the present prepared nitriles are commercially available and they are identified with authentic nitrile compounds.

Reference： [1]Location in patent: experimental part Suzuki, Yusuke; Yoshino, Takumi; Moriyama, Katsuhiko; Togo, Hideo [Tetrahedron, 2011, vol. 67, # 21, p. 3809 - 3814]

9
[ 67-56-1 ]
[ 104-92-7 ]
[ 33513-42-7 ]
[ 121-98-2 ]
[ 7291-00-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 73% 2: 8%	Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Stage #3: methanol Further stages;	4.3. Typical procedure for one-pot conversion of aromatic bromides into aromatic methyl esters with DMF General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82% yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.

Reference： [1]Location in patent: experimental part Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo [Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709]

10
[ 104-92-7 ]
[ 64-17-5 ]
[ 33513-42-7 ]
[ 94-30-4 ]
[ 7291-00-1 ]
[ 123-11-5 ]

Yield	Reaction Conditions	Operation in experiment
1: 19% 2: 55% 3: 8%	Stage #1: 1-bromo-4-methoxy-benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran; hexane at -78 - 20℃; for 2h; Stage #3: ethanol Further stages;	4.3. Typical procedure for one-pot conversion of aromatic bromides into aromatic methyl esters with DMF General procedure: n-BuLi (1.67 M solution in hexane, 1.3 mL, 2.2 mmol) was added dropwise into a solution of p-bromoanisole (383 mg, 2.0 mmol) in THF (3 mL) at -78 °C for 30 min. Then, DMF (0.22 mL, 2.2 mmol) was added to the mixture and the obtained mixture was stirred at rt. After 2 h at the same temperature, THF was removed. Then, MeOH (3 mL) was added to the residue and the mixture was stirred at room temperature. After 30 min, I2 (1523 mg, 6 mmol) and K2CO3 (829 mg, 6 mmol) were added at 0 °C and the obtained mixture was stirred for 22 h at rt. The reaction mixture was quenched with satd aq Na2SO3 (5 mL) and was extracted with CHCl3 (3×20 mL). The organic layer was washed with brine and dried over Na2SO4 to provide methyl 4-methoxy-1-benzoate in 82% yield. If necessary, the product was purified by short column chromatography (SiO2:hexane:EtOAc=9:1) to give pure methyl 4-methoxybenzoate as a colorless oil.

Reference： [1]Location in patent: experimental part Ushijima, Sousuke; Moriyama, Katsuhiko; Togo, Hideo [Tetrahedron, 2012, vol. 68, # 24, p. 4701 - 4709]

11
[ 33513-42-7 ]
[ 105-13-5 ]
[ 7291-00-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide In 1,1,2-trichloroethane; water at 90℃; for 12h;	General procedure for the reaction of amides formation General procedure: To a solution of alcohols 1 (0.1 mmol) in TCE (1.0 mL) was added n-Bu4NI (20 mol%) and N, N-disubstituted formamides 2 (0.5 mmol), followed by adding a solution of TBHP (6.0 equiv., 70% aqueous solution). The resulting mixture was stirred at 90 oC until it completed. When the reaction was finished, the reaction mixture was cooled to room temperature and poured into saturated Na2S2O3 solution (3.0 mL), extracted with EtOAc (3×8.0 mL), then washed with saturated brine. The combined organic layers were dried over anhydrous Na2SO4. After removing the solvents in vacuo, the residue was purified by flash column chromatography on silica gel or preparative TLC on GF 254 to afford the desired products 3.
46%	With tert.-butylhydroperoxide In water; toluene at 20 - 80℃; Inert atmosphere;

Reference： [1]Li, Huamin; Xie, Jin; Xue, Qicai; Cheng, Yixiang; Zhu, Chengjian [Tetrahedron Letters, 2012, vol. 53, # 48, p. 6479 - 6482,4]
[2]Mohebali, Haleh; Mahjoub, Ali Reza; Karimi, Meghdad; Heydari, Akbar [Applied Organometallic Chemistry, 2019, vol. 33, # 5]

12
[ 124-40-3 ]
[ 105-13-5 ]
[ 7291-00-1 ]

Yield	Reaction Conditions	Operation in experiment
98%	With oxygen; sodium hydroxide In water at 25℃; for 24h;	General procedure for the amidation using Au/HAP catalyst General procedure: Unless otherwise noted, reactions were carried out as following: a mixture of alcohol 1 (1.00mmol, 2.0 equiv), amine 2 (0.50 mmol), sodium hydroxide (0.50 mmol) and Au/HAP (45 mg, 1.69wt%) were vigorously stirred in 0.5 mL H2O at 40 °C for 24 h under oxygen balloon. After completion of the reaction, the mixture is cooled to room temperature, diluted with ethyl acetate. The catalyst was separated by centrifugation and washed with ethyl acetate (3 x 15.0 mL). The combined organic layer was washed by saturated NaCl solution and dried over anhydrous magnesium sulfate and the solvent was removed under vacuum. The residue was purified by flash chromatography on a short silica gel (eluent: petroleum ether/ethyl acetate = 10:1, 2:1, or 1:1) toafford the corresponding amide 3.
95%	With oxygen; sodium hydroxide In water at 25℃; for 24h; Green chemistry;
78%	With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene In acetonitrile Reflux;	General procedure for the oxidative amidation of aryl alcohol with secondary amine General procedure: To a mixture of aryl alcohol (1.0 mmol), appropriate amine (2.5 mmol) and TBHP (70 wt % in H2O, 8.0 mmol) in acetonitrile (5 mL), was added DIB (0.2 mmol, 20 mol %) at room temperature. The reaction was allowed to stir at reflux temperature for 5-6 h. After the reaction was complete, as indicated by TLC, the mixture was cooled to room temperature. The volatiles were removed under reduced pressure and 10 mL saturated solution of NaHCO3 was added. The mixture was extracted with ethylacetate (310 mL). The combined organic phases were dried with Na2SO4 and evaporated under vacuum. Purification of the residue by column chromatography (petroleum ether/EtOAc) afforded the desired amide.

Reference： [1]Wang, Wentao; Cong, Yu; Zhang, Leilei; Huang, Yanqiang; Wang, Xiaodong; Zhang, Tao [Tetrahedron Letters, 2014, vol. 55, # 1, p. 124 - 127]
[2]Zhang, Leilei; Wang, Wentao; Wang, Aiqin; Cui, Yitao; Yang, Xiaofeng; Huang, Yanqiang; Liu, Xiaoyan; Liu, Wengang; Son, Jin-Young; Oji, Hiroshi; Zhang, Tao [Green Chemistry, 2013, vol. 15, # 10, p. 2680 - 2684]
[3]Sutar, Yogesh B.; Bhagat, Saket B.; Telvekar, Vikas N. [Tetrahedron Letters, 2015, vol. 56, # 48, p. 6768 - 6771]

13
[ 104-93-8 ]
[ 33513-42-7 ]
[ 7291-00-1 ]
[ 3400-22-4 ]

Yield	Reaction Conditions	Operation in experiment
12%; 66%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; zinc dibromide; In acetonitrile; at 80℃; for 16h;	General procedure: Under air, in a 50 mL tube, ZnBr2 (20 mol %), TBAI(10 mol%), and a stirring bar was added. Then toluene (10 mmol), DMF (1 mmol), MeCN(2 mL) and TBHP (6 mmol) were injected by syringe. Then close the tube and keepthe final solution at 80 oC for 16 h. When the reaction wasfinished, the solvent was removed in vacuo, and the residue was purified byflash column (petroleum ether/ethyl acetate). All the products are commerciallyavailable.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 5082 - 5084

14
[ 17985-72-7 ]
[ 7291-00-1 ]
[ 15175-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	In hexane; ethyl acetate; toluene;	Example 22 Reduction of N, N-dimethyl-4-methoxybenzamide A 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the flask, iron complex A (1.0 mg, 0.002 mmol) was admitted as catalyst and dissolved in toluene (0.5 mL). To the solution, <strong>[17985-72-7]1,2-<strong>[17985-72-7]bis(dimethylsilyl)benzene</strong></strong> (475 muL) was added through a syringe, and N,N-dimethyl-4-methoxybenzamide (179 mg, 1.0 mmol) was added. The solution was stirred at 100 C. for 30 minutes. Toluene was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (10/1) as developing solvent, obtaining N,N-dimethyl-4-methoxybenzylamine (159 mg, 0.96 mmol, 96%).

Reference： [1]Patent: US2016/23196,2016,A1

15
[ 7291-00-1 ]
[ 137-07-5 ]
[ 6265-92-5 ]

Yield	Reaction Conditions	Operation in experiment
87%	With Imidazole hydrochloride at 160℃; for 10h; Green chemistry;	2.3 General procedure for the synthesis of benzoxazole derivatives (2b,2d, 2e, 2f, 2i) and benzothiazole derivatives (4e-4k) General procedure: To a mixture of 1a (0.6g, 4.8 mmol, 1equiv), imidazolium chloride (0.25g, 2.4 mmol,0.5equiv) and N,N-dimethylbenzamide (1.43g, 9.6 mmol, 2 equiv) was added. Themixture was stirred at 160°C for 10h. after completion of the reaction. 15ml water was added and the resulting mixture was extracted with 20ml EA thrice, and the combined organic layers were dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography on silica gel using PE/EA as eluent to obtain thepure desired product.

Reference： [1]Tian, Qingqiang; Luo, Wen; Gan, Zongjie; Li, Dan; Dai, Zeshu; Wang, Huajun; Wang, Xuetong; Yuan, Jianyong [Molecules, 2019, vol. 24, # 1]

16
[ 19513-80-5 ]
[ 124-40-3 ]
[ 7291-00-1 ]
[ 90-05-1 ]

Yield	Reaction Conditions	Operation in experiment
78%; 87%	With copper diacetate; In water; dimethyl sulfoxide; at 20℃; for 12h;Sealed tube;	In a 15 mL pressure bottle, 0.125 mmol of <strong>[19513-80-5]1-(4-methoxyphenyl)-2-(2-methoxyphenoxy)ethanone</strong>, 0.0125 mmol of copper acetate, and 0.625 mmol of dimethylamine (40) were added. % aqueous solution), 1 mL of dimethyl sulfoxide was added, replaced with fresh air, sealed, and stirred at room temperature for 12 h. After the reaction was completed, the product was chromatographed, and the yields of amide and phenol were shown in Table 1.

Reference： [1]Patent: CN109836311,2019,A .Location in patent: Paragraph 0046; 0047; 0070; 0072
[2]ChemSusChem,2020

17
[ 7291-00-1 ]
[ 3400-22-4 ]

Reference： [1]Organic Letters,2020,vol. 22,p. 4583 - 4587

18
[ 92409-23-9 ]
[ 124-40-3 ]
[ 7291-00-1 ]
[ 90-05-1 ]

Reference： [1]ChemSusChem,2020,vol. 13,p. 4660 - 4665

19
[ 35812-01-2 ]
[ 7291-00-1 ]
N-((1,1-dioxido-3-oxobenzo[d]isothiazol-2(3H)-yl)methyl)-4-methoxy-N-methylbenzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With lithium tert-butoxide In chlorobenzene at 35℃; Sealed tube; Irradiation; regioselective reaction;

Reference： [1]Pan, Lei; Elmasry, Joseph; Osccorima, Tomas; Cooke, Maria Victoria; Laulhé, Sébastien [Organic Letters, 2021, vol. 23, # 9, p. 3389 - 3393]

20
[ 7291-00-1 ]
[ 20876-99-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium <i>tert</i>-butylate; diphenylphosphane In N,N-dimethyl-formamide at 80℃; for 12h; Sealed tube;

Reference： [1]Pan, Wenjing; Li, Chenchen; Zhu, Haoyin; Li, Fangfang; Li, Tao; Zhao, Wanxiang [Organic and Biomolecular Chemistry, 2021, vol. 19, # 35, p. 7633 - 7640]

21
[ 104-92-7 ]
[ 18503-89-4 ]
[ 7291-00-1 ]

Yield	Reaction Conditions	Operation in experiment
69%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; for 24h;

Reference： [1]Hirata, Shuichi; Osako, Takao; Uozumi, Yasuhiro [Helvetica Chimica Acta, 2021, vol. 104, # 11]

22
[ 623-12-1 ]
[ 18503-89-4 ]
[ 7291-00-1 ]

Yield	Reaction Conditions	Operation in experiment
66%	With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 140℃; for 24h;

Reference： [1]Hirata, Shuichi; Osako, Takao; Uozumi, Yasuhiro [Helvetica Chimica Acta, 2021, vol. 104, # 11]

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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. 7291-00-1 ] {[proInfo.proName]}

Quality Control of [ 7291-00-1 ]

Related Doc. of [ 7291-00-1 ]

Product Details of [ 7291-00-1 ]

Safety of [ 7291-00-1 ]

Application In Synthesis of [ 7291-00-1 ]

[ 7291-00-1 ] Synthesis Path-Downstream 1~22

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry