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Quality Control of [ 34046-43-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 34046-43-0 ]

Product Details of [ 34046-43-0 ]

CAS No. :	34046-43-0	MDL No. :	MFCD09743805
Formula :	C₁₀H₁₀O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IQYZISJXVKSMNW-UHFFFAOYSA-N
M.W :	178.19	Pubchem ID :	10943020
Synonyms :

Safety of [ 34046-43-0 ]

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

Application In Synthesis of [ 34046-43-0 ]

* 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 [ 34046-43-0 ]
Downstream synthetic route of [ 34046-43-0 ]

[ 34046-43-0 ] Synthesis Path-Upstream 1~12

1
[ 75-03-6 ]
[ 119-67-5 ]
[ 34046-43-0 ]

Reference： [1] Heterocycles, 2009, vol. 78, # 9, p. 2209 - 2216
[2] Journal of Organic Chemistry, 1971, vol. 36, # 19, p. 2740 - 2743
[3] Patent: US5190942, 1993, A,
[4] Organic Letters, 2012, vol. 14, # 14, p. 3748 - 3751
[5] Tetrahedron, 2013, vol. 69, # 15, p. 3287 - 3292
[6] Patent: WO2016/100157, 2016, A2, . Location in patent: Page/Page column 45
[7] Patent: WO2016/89721, 2016, A1, . Location in patent: Page/Page column 35
[8] Patent: WO2016/100161, 2016, A1, . Location in patent: Page/Page column 46
[9] Patent: WO2016/85783, 2016, A1, . Location in patent: Page/Page column 43

2
[ 64-67-5 ]
[ 119-67-5 ]
[ 34046-43-0 ]

Reference： [1] Synthesis, 1985, # 1, p. 40 - 45
[2] Organic Letters, 2001, vol. 3, # 22, p. 3487 - 3490
[3] Patent: US4846873, 1989, A,

3
[ 88674-90-2 ]
[ 34046-43-0 ]

Reference： [1] Organic Preparations and Procedures International, 1996, vol. 28, # 5, p. 622 - 627
[2] Tetrahedron Letters, 1990, vol. 31, # 47, p. 6781 - 6784

4
[ 64-17-5 ]
[ 119-67-5 ]
[ 34046-43-0 ]

Reference： [1] European Journal of Organic Chemistry, 2009, # 18, p. 3011 - 3021

5
[ 15226-74-1 ]
[ 64-17-5 ]
[ 6630-33-7 ]
[ 34046-43-0 ]

Reference： [1] New Journal of Chemistry, 2013, vol. 37, # 10, p. 3050 - 3056

6
[ 27332-37-2 ]
[ 34046-43-0 ]

Reference： [1] Heterocycles, 1981, vol. 15, # 2, p. 985 - 991

7
[ 64-17-5 ]
[ 643-79-8 ]
[ 16824-02-5 ]
[ 34046-43-0 ]

Reference： [1] Tetrahedron, 2015, vol. 71, # 49, p. 9264 - 9270

8
[ 368-39-8 ]
[ 119-67-5 ]
[ 34046-43-0 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1992, # 10, p. 1223 - 1228

9
[ 6525-45-7 ]
[ 34046-43-0 ]

Reference： [1] Journal of Organic Chemistry, 1981, vol. 46, # 3, p. 602 - 607

10
[ 119-67-5 ]
[ 34046-43-0 ]

Reference： [1] Monatshefte fuer Chemie, 1904, vol. 25, p. 497

11
[ 70760-53-1 ]
[ 34046-43-0 ]
[ 119-67-5 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1991, vol. 39, # 3, p. 545 - 548

12
[ 27332-37-2 ]
[ 34046-43-0 ]
[ 93-89-0 ]
[ 6287-86-1 ]
[ 101-97-3 ]
[ 141-05-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1993, vol. 41, # 12, p. 2187 - 2189

[ 34046-43-0 ] Synthesis Path-Downstream 1~6

1
[ 75-03-6 ]
[ 119-67-5 ]
[ 34046-43-0 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;
79%	With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 4h;	1 Ethyl 2-formylbenzoate 1a o-carboxybenzaldehyde (1.5g, 10 mmol) was weighed into a 100 mL three-necked flask, 69 cesium carbonate (6.5g, 20 mmol) and 20 ml of 70 N,N-dimethylformamide (DMF) were added, and 71 ethyl iodide (4.68 g, 30 mmol) was added with electromagnetic-stirring and heated to 70 °C for 4 h. The reaction was monitored by TLC until the end of the reaction, and the heating was stopped. 20 mL of 60 water was added to the reaction flask. The reaction mixture was extracted for three times with dichloromethane and water. The organic phases were pooled and dried over anhydrous sodium sulfate and suction-filtered, and the filtrate was evaporated to dryness and purified through silica gel column chromatography to give a colorless transparent 72 liquid (1.4 g, yield 79%). 1H NMR (400 MHz, DMSO-d6, ppm): δ 10.41 (s, 1H), 7.92-7.90 (m, 1H), 7.88-7.85 (m, 1H), 7.81-7.77 (m, 2H), 4.40 (q, J = 7.2 Hz, 2H), 1.34 (t, J = 7.2 Hz, 3H). LC-MS (ESI) calcd for C10H10O3 [M+H]+ 179.06, found 179.10.
68%	With potassium carbonate In N,N-dimethyl-formamide at 20℃;

	With potassium carbonate In butanone
	With sodium hydrogencarbonate In <i>N</i>-methyl-acetamide	A A. A. 2-formylbenzoic acid, ethyl ester 2-Carboxybenzaldehyde (2.018g, 13.4 mmol, 1.0 eq.) was combined with sodium bicarbonate (2.258 g, 26.9 mmol, 2.0 eq.) and iodoethane (2.15 ml, 26.9 mmol, 2.0 eq.) in dimethylformamide (13.4 ml, 1M) and stirred at room temperature for 16 hours. The reaction was diluted with water (25 ml) and extracted with ether: hexane (1:1, 3X20 ml). The combined organic extracts were washed with aqueous 10% sodium bisulfite (1X25 ml), water (1X25 ml) and aqueous saturated sodium chloride (1X25 ml), dried over sodium sulfate, filtered through magnesium sulfate and concentrated. The residue was chromatographed on Merck silica gel (20 g) eluding with hexane: ether (14:1) to provide the title A compound (1.485 g).
	With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;
	With potassium carbonate In N,N-dimethyl-formamide for 4h; Reflux;	6 2.2.1. Representative procedure A: synthesis of alkyl 2-formylbenzoate General procedure: Iodomethane (0.6 mL, 9.5 mmol) was added to a stirred solution of 2-formylbenzoic acid (0.765 g, 5.1 mmol) andpotassium carbonate (0.387 g, 2.8 mmol) in DMF (4 mL). The reactionmixture was refluxed for 4 h, diluted with water (8 mL), andextracted with DCM. The combined organic phases were washedwith 1 N HCl (4 mL), saturated aqueous NaHCO3 (4 mL), and driedover Na2SO4. After filtration and evaporation of the solvents invacuum, the crude product was purified by column chromatographyon silica gel
	With potassium carbonate In acetone at 70℃;	1 Step 1: ethyl 2-formylbenzoate (P1) To a suspension of 2-formylbenzoic acid (34.5 g, 0.23 mol) and K2C03 (65.1 g, 0.47 mol) in acetone (500 mL) was added EtI (72 g, 0.46 mol). The resulting mixture was stirred at 70 °C overnight. After cooled to RT, the mixture was filtered and the filtrate was concentrated in vacuo to give the title compound which was used without further purification.LRMS m/z (M+H) 179.2 found, 179.2 required.
	With potassium carbonate In acetone at 70℃;	1 Step 1: ethyl 2-formylbenzoate (C1) To a suspension of 2-formylbenzoic acid (34.5 g, 0.23 mol) and K2CO3 (65.1 g, 0.47 mol) in acetone (500 mL) was added EtI (72 g, 0.46 mol). The resulting mixture was stirred at 70 oC overnight. After cooled to RT, the mixture was filtered and the filtrate was concentrated in vacuo to give the title compound as an oil which was used without further purification. LRMS m/z (M+H) 179.2 found, 179.2 required.
	With potassium carbonate In acetone at 70℃;	1 Step 1: ethyl 2-formylbenzoate (PI) Intermediate P Step 1: ethyl 2-formylbenzoate (PI) To a suspension of 2-formylbenzoic acid (34.5 g, 0.23 mol) and K2C03 (65.1 g, 0.47 mol) in acetone (500 mL) was added EtI (72 g, 0.46 mol). The resulting mixture was stirred at 70 °C overnight. After cooled to RT, the mixture was filtered and the filtrate was concentrated in vacuo to give the title compound which was used without further purification. LRMS m/z (M+H) 179.2 found, 179.2 required.
	With potassium carbonate In acetone at 70℃;	1 Step 1: ethyl 2-formylbenzoate (J 1) To a suspension of 2-formylbenzoic acid (34.5 g, 0.23 mol) and K2C03 (65.1 g, 0.47mol) in acetone (500 mL) was added EtI (72 g, 0.46 mol). The resulting mixture was stirred at 70°C overnight. After cooling to room temperature, the mixture was filtered and the filtrate was concentrated in vacuo to give J1 as an oil which was used without further purification. LRMS mlz (M+H) 179.2 found, 179.2 required.

Reference： [1]Location in patent: scheme or table Aoyama, Atsushi; Aoyama, Hiroshi; Makishima, Makoto; Hashimoto, Yuichi; Miyachi, Hiroyuki [Heterocycles, 2009, vol. 78, # 9, p. 2209 - 2216]
[2]Current Patent Assignee: EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY - EP3459937, 2019, A1 Location in patent: Paragraph 0099-0100
[3]Iyori, Yasuaki; Takahashi, Kenjiro; Yamazaki, Ken; Ano, Yusuke; Chatani, Naoto [Chemical Communications, 2019, vol. 55, # 90, p. 13610 - 13613]
[4]Newman,M.S.; ud Din,Z. [Journal of Organic Chemistry, 1971, vol. 36, # 19, p. 2740 - 2743]
[5]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO - US5190942, 1993, A
[6]Mirabdolbaghi, Roya; Dudding, Travis [Organic Letters, 2012, vol. 14, # 14, p. 3748 - 3751]
[7]Mirabdolbaghi, Roya; Dudding, Travis [Tetrahedron, 2013, vol. 69, # 15, p. 3287 - 3292]
[8]Current Patent Assignee: MERCK & CO INC - WO2016/100157, 2016, A2 Location in patent: Page/Page column 45
[9]Current Patent Assignee: MERCK & CO INC - WO2016/89721, 2016, A1 Location in patent: Page/Page column 35
[10]Current Patent Assignee: MERCK & CO INC - WO2016/100161, 2016, A1 Location in patent: Page/Page column 46
[11]Current Patent Assignee: MERCK & CO INC - WO2016/85783, 2016, A1 Location in patent: Page/Page column 43

2
[ 6525-45-7 ]
[ 34046-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: FeCl₃ / CH₂Cl₂ / Heating 2: 1) Et₃SiH, 2) H₂O / 1) CH₂Cl₂, reflux, 2) heating

Reference： [1]Fry, James L.; Ott, Roger A. [Journal of Organic Chemistry, 1981, vol. 46, # 3, p. 602 - 607]

3
[ 62240-37-3 ]
[ 34046-43-0 ]
[ 817554-52-2 ]

Reference： [1]European Journal of Organic Chemistry,2009,p. 3011 - 3021

4
[ 34046-43-0 ]
[ 23308-83-0 ]
[ 90011-52-2 ]

Yield	Reaction Conditions	Operation in experiment
60%	With sodium ethanolate In dichloromethane at 20℃;

Reference： [1]Location in patent: scheme or table Aoyama, Atsushi; Aoyama, Hiroshi; Makishima, Makoto; Hashimoto, Yuichi; Miyachi, Hiroyuki [Heterocycles, 2009, vol. 78, # 9, p. 2209 - 2216]

5
[ 34046-43-0 ]
[ 2551-83-9 ]
(R)-3-allylisobenzofuran-1(3H)-one [ No CAS ]
[ 24282-29-9 ]

Yield	Reaction Conditions	Operation in experiment
58%	With silver fluoride; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In methanol; at -20℃; for 5h;	General procedure: Representative procedure C: synthesis of substituted (R)-3-allylisobenzofuran-1(3H)-one A round-bottomed flask wrapped in aluminum foil was charged with AgF (7.75 mg, 0.061 mmol), (R)-BINAP (22.8 g, 0.035 mmol), anhydrous MeOH (0.2 mL), and stirred for 10 min at room temperature. The mixture was cooled to -20 C (dry ice/xylene bath) followed by dropwise addition of methyl 2-formylbenzoate 7a (100 mg, 0.61 mmol) and <strong>[2551-83-9]allyltrimethoxysilane</strong> (154 muL, 0.91 mmol). After 4 h, the reaction mixture was quenched with a mixture of 1 N HCl (3 mL) and KF (ca. 0.3 g) and stirred for 30 min. The resulting precipitate was filtered and the filtrate was dried over MgSO4. After evaporation of the solvents in vacuum, the crude product was purified by column chromatography on silica gel (n-hexane/EtOAc: 1/1) to yield 8a as a colorless oil

Reference： [1]Tetrahedron,2013,vol. 69,p. 3287 - 3292

6
[ 34046-43-0 ]
[ 96145-98-1 ]
ethyl (Z)-2-((5-oxo-1-phenyl-3-(trifluoromethyl)-1,5-dihydro-4H-pyrazol-4-ylidene)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	at 160℃; for 0.25h;	General procedure: 3a (141mg, 0.5mmol) and benzaldehyde (106mg, 0.75mmol) were placed in a microwave-proof glass tube and heated for 15 min at 160C in a commercial microwave apparatus. The reaction was cooled to room temperature. The reaction product was precipitated by addition of ethyl acetate and hexane, collected by filtration, and recrystallized from hexane and ethyl acetate. The title compound was obtained as an orange solid (93mg, 0.30mmol, 59%).

Reference： [1]Bioorganic and Medicinal Chemistry,2018,vol. 26,p. 2973 - 2983

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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. 34046-43-0 ] {[proInfo.proName]}

Quality Control of [ 34046-43-0 ]

Related Doc. of [ 34046-43-0 ]

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Application In Synthesis of [ 34046-43-0 ]

[ 34046-43-0 ] Synthesis Path-Upstream 1~12

[ 34046-43-0 ] Synthesis Path-Downstream 1~6

Related Functional Groups of [ 34046-43-0 ]

Aryls

Aldehydes

Esters

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[ 34046-43-0 ]