[ CAS No. 937-41-7 ]

Name: 937-41-7|Phenyl acrylate|97% (stabilized with BHT)
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Quality Control of [ 937-41-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 937-41-7 ]

Product Details of [ 937-41-7 ]

CAS No. :	937-41-7	MDL No. :	MFCD00048145
Formula :	C₉H₈O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WRAQQYDMVSCOTE-UHFFFAOYSA-N
M.W :	148.16 g/mol	Pubchem ID :	61242
Synonyms :

Calculated chemistry of [ 937-41-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	42.27
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.04
Log Po/w (XLOGP3) :	2.08
Log Po/w (WLOGP) :	1.78
Log Po/w (MLOGP) :	2.16
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	2.02

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.27
Solubility :	0.787 mg/ml ; 0.00531 mol/l
Class :	Soluble
Log S (Ali) :	-2.26
Solubility :	0.811 mg/ml ; 0.00547 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.51
Solubility :	0.456 mg/ml ; 0.00308 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.47

Safety of [ 937-41-7 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P501-P273-P260-P270-P264-P280-P391-P314-P337+P313-P305+P351+P338-P301+P312+P330	UN#:	3082
Hazard Statements:	H302-H319-H372-H410	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 937-41-7 ]

* 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 [ 937-41-7 ]
Downstream synthetic route of [ 937-41-7 ]

[ 937-41-7 ] Synthesis Path-Upstream 1~1

1
[ 937-41-7 ]
[ 6968-35-0 ]

Reference： [1] Journal of the Chemical Society, 1956, p. 1585,1588

[ 937-41-7 ] Synthesis Path-Downstream 1~59

1
[ 110-86-1 ]
[ 24552-27-0 ]
[ 937-41-7 ]

Reference： [1]Skraup; Nieten [Chemische Berichte, 1924, vol. 57, p. 1303]

2
[ 24552-27-0 ]
[ 937-41-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine

Reference： [1]Skraup; Nieten [Chemische Berichte, 1924, vol. 57, p. 1303]

3
[ 79-10-7 ]
[ 108-95-2 ]
[ 937-41-7 ]

Yield	Reaction Conditions	Operation in experiment
78%	With lithium hydroxide monohydrate; di-tert-butyl dicarbonate; magnesium sulfate; at 25℃; for 24h;	General procedure: In a 100 mL capacity eggplant-shaped flask, 10.000 grams (106.26 mmol) of 6 phenol, 7.657 grams (106.26 mmol) of 22 acrylic acid, 23.664 grams (106.26 mmol) of 8 di-t-butyl dicarbonate, 0.046 grams (0.53 mmol, 0.5 mol %) of 23 lithium bromide, and 0.064 grams (0.53 mmol, 0.5 mol %) of 24 magnesium sulfate were added successively. Then, reaction was carried out at 25 C. while the mixture was stirred. Accordingly, 25 phenyl acrylate was produced. The reaction result obtained 24 hours after the start of reaction is shown in Table 4.
35%	With potassium carbonate; 2-chloropyridinium iodide; In dichloromethane; at 20℃; for 4h;	General procedure: To a suspension of 562 mg 2-chloropyridinium iodide (2.2 mmol, 1.1 equiv) and 612 mg potassium carbonate (4.4 mmol, 2.2 equiv) in 20 cm3 dichloromethane, the corresponding acid (2.2 mmol, 1.1 equiv) and the corresponding phenol (2.0 mmol, 1.0 equiv) were added. The reaction was stirred at room temperature for 4 h. Thereaction mixture was then filtered through a silica plug, washed with dichloromethane, and concentrated. The residue was purified by column chromatography to yield the desired product.

Reference： [1]Journal of the Chinese Chemical Society,2014,vol. 61,p. 583 - 588
[2]Patent: US2018/354885,2018,A1 .Location in patent: Paragraph 0071; 0072; 0074
[3]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3281 - 3286
[4]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 295 - 299
[5]Monatshefte fur Chemie,2018,vol. 149,p. 1059 - 1068
[6]Journal of the American Chemical Society,1953,vol. 75,p. 984
[7]Journal of Organometallic Chemistry,1986,vol. 304,p. 301 - 308
[8]Chemical Papers,2015,vol. 69,p. 1598 - 1607

4
[ 814-68-6 ]
[ 108-95-2 ]
[ 937-41-7 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	Example 1; Materials and Laboratory Synthesis of the Monomers of the Present Invention; The well plates and most chemicals used in the monomer syntheses and testing, including the alcoholic precursors, triethylamine (TEA), acryloyl chloride, well plates, and acetonitrile, were purchased from Sigma-Aldrich. The dichloromethane also used in the syntheses was purchased from Pharmacia. The material used for the coating formulations was obtained from Allied Photochemical and is a proprietary formulation. Cytec Specialty Chemicals provided HDODA used in the photo-DSC testing. Albemarle Corporation donated the initiator, 2,2-dimethoxy-2-acetophenone (DMPA) used in the photo-DSC studies. The uncoated, polished stainless steel plates were purchased from Q-Panel Products. Methyl ethyl ketone (MEK) for the double rub solvent resistance test was purchased from The Paint Center. Pap-smear cytology fixative spray was obtained from Andwin Scientific. The E. coli was stained using Hema-diff solution 3:thiazine dye from Anaphth.Each alcohol precursor was dissolved in dichloromethane after adding TEA in slight molar excess. Under a ventilation hood, acryloyl chloride was added dropwise producing hydrogen chloride gas, which was, inpart, consumed by the TEA. The round bottom flask was purged with nitrogen for five seconds and stoppered to provide a nitrogen atmosphere for the reaction to take place. The reaction mixture stirred for 24 hours at room temperature using a magnetic stir bar to allow for complete reaction. TEA?HCl precipitate formed which was removed by suction filtration. Unreacted acryloyl chloride was removed by washing with five milliliters (5 ml) of deionized water five times in a separatory funnel. A rotary evaporator was used to remove any excess dichloromethane. The reaction scheme is shown below (Reaction 1). The structure of each monomer was verified by infrared spectroscopy (IR) and nuclear magnetic resonance (NMR).Furthermore, it is recognized that the industrial synthesis would involve a synthetic scheme involving either: 1) the esterification reaction of acrylic acid with the alcoholic precursor, or 2) the transesterification reaction of methyl acrylate (or similar derivative) with the alcoholic precursor with both procedures requiring an acid catalyst, elevated temperatures, and a vacuum to remove the condensate from the reaction vessel.

Reference： [1]Journal of Agricultural and Food Chemistry,2004,vol. 52,p. 7480 - 7483
[2]Journal of the Chemical Society. Perkin transactions I,1994,p. 407 - 412
[3]Patent: JP2005/112764,2005,A .Location in patent: Page/Page column 6-7
[4]Journal of Organic Chemistry,2015,vol. 80,p. 4638 - 4649
[5]Molecules,2002,vol. 7,p. 721 - 733
[6]Angewandte Chemie - International Edition,2013,vol. 52,p. 5818 - 5821
    Angew. Chem.,2013,vol. 125,p. 5930 - 5933,4
[7]Gazzetta Chimica Italiana,1966,vol. 96,p. 1035 - 1045
[8]Synthetic Communications,1990,vol. 20,p. 1915 - 1921
[9]Journal of the Chemical Society. Perkin transactions II,1983,p. 131 - 134
[10]Tetrahedron,1992,vol. 48,p. 6371 - 6384
[11]Journal of Organic Chemistry,2005,vol. 70,p. 7810 - 7815
[12]Chemical Communications,2008,p. 3798 - 3800
[13]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 731 - 734
[14]Journal of Chemical Research,2010,p. 61 - 67
[15]Patent: US2009/304621,2009,A1 .Location in patent: Page/Page column 11-12
[16]Journal of Organic Chemistry,2012,vol. 77,p. 747 - 753
[17]Angewandte Chemie - International Edition,2015,vol. 54,p. 4246 - 4249
    Angew. Chem.,2015,vol. 127,p. 4320 - 4323
[18]Organic Letters,2015,vol. 17,p. 6090 - 6093
[19]Chemistry - A European Journal,2015,vol. 21,p. 18961 - 18965
[20]Patent: DE570955,
    Fortschr. Teerfarbenfabr. Verw. Industriezweige,vol. 19,p. 374
[21]Chemical Communications,2020,vol. 56,p. 4284 - 4287

5
[ 79-10-7 ]
[ 108-95-2 ]
[ 937-41-7 ]
[ 24552-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	With phosphorus pentachloride In neat (no solvent) 1.) 110-120 deg C, 1 h, 2.) room temp., 2.5 h then 90 deg C, 3 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Mahajan; Araujo [Canadian Journal of Chemistry, 1987, vol. 65, # 1, p. 224 - 225]

6
[ 814-68-6 ]
[ 108-95-2 ]
[ 937-41-7 ]
[ 24552-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	With aluminium trichloride In neat (no solvent) 1.) cooled by tap water, 16 h, 2.) 80 deg C, 4 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
19.4 g	With aluminium trichloride In neat (no solvent) 1.) 80-90 deg C, 3 h, 2.) 100 deg C, 1 h; Yields of byproduct given;

Reference： [1]Mahajan; Araujo [Canadian Journal of Chemistry, 1987, vol. 65, # 1, p. 224 - 225]
[2]Mahajan; Araujo [Canadian Journal of Chemistry, 1987, vol. 65, # 1, p. 224 - 225]

7
[ 500-22-1 ]
[ 937-41-7 ]
2-[(hydroxy)(pyridin-3-yl)methyl]-1-phenoxyprop-2-en-1-one [ No CAS ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 1051 - 1057
[2]Molecules,2002,vol. 7,p. 721 - 733
[3]Tetrahedron Letters,1996,vol. 37,p. 1715 - 1718

8
[ 937-41-7 ]
[ 51608-60-7 ]
phenyl 2-[phenyl-(toluene-4-sulfonylamino)methyl]acrylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 417 - 425
[2]Tetrahedron,2005,vol. 61,p. 12026 - 12032

9
[ 937-41-7 ]
[ 75159-10-3 ]
phenyl 2-[(4-methylphenyl)-(toluene-4-sulfonylamino)methyl]acrylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 417 - 425
[2]Tetrahedron,2005,vol. 61,p. 12026 - 12032

10
[ 937-41-7 ]
[ 357417-22-2 ]
2-[(4-chlorophenyl)-(toluene-4-sulfonylamino)-methyl]-acrylic acid phenyl ester [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 417 - 425
[2]Tetrahedron,2005,vol. 61,p. 12026 - 12032

11
[ 937-41-7 ]
[ 951762-59-7 ]
phenyl 2-[(4-ethylphenyl)-(toluene-4-sulfonylamino)methyl]acrylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 417 - 425
[2]Tetrahedron,2005,vol. 61,p. 12026 - 12032

12
tris(trimethylsilyl)-(2-methylpropenyloxy)-silane [ No CAS ]
[ 937-41-7 ]
3,3-dimethyl-2-(tris-trimethylsilyl-silanyloxy)-cyclobutanecarboxylic acid phenyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3127 - 3129

13
cyclohexylidenemethoxy-tris(trimethylsilyl)-silane [ No CAS ]
[ 937-41-7 ]
1-(tris-trimethylsilyl-silanyloxy)-spiro[4.5]nonane-2-carboxylic acid phenyl ester [ No CAS ]

Reference： [1]Organic Letters,2005,vol. 7,p. 3127 - 3129

14
[ 937-41-7 ]
[ 536-74-3 ]
3-methyl-1H-indene-2-carboxylic acid phenyl ester [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 2891 - 2893

15
[ 937-41-7 ]
[ 5454-45-5 ]
6-ethylsulfanyl-4-oxo-hexanoic acid phenyl ester [ No CAS ]
5-ethylsulfanyl-3-(3-ethylsulfanyl-propionyloxy)-2-methyl-pentanoic acid phenyl ester [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 18012 - 18013

16
[ 937-41-7 ]
[ 98-86-2 ]
3-methyl-1H-indene-2-carboxylic acid phenyl ester [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2006,vol. 45,p. 2766 - 2768

17
[ 937-41-7 ]
[ 7383-70-2 ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 7542 - 7545

18
[ 937-41-7 ]
[ 95605-38-2 ]
[ 7182-38-9 ]

Yield	Reaction Conditions	Operation in experiment
64%	With aluminum (III) chloride

Reference： [1]Location in patent: body text Tao, Yun-Hai; Xu, Hui-Bi; Yang, Xiang-Liang [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 3, p. 731 - 734]

19
[ 767-60-2 ]
[ 937-41-7 ]
C₁₉H₁₆O₂ [ No CAS ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 3504 - 3507

20
[ 937-41-7 ]
[ 18640-74-9 ]
[ 1236376-45-6 ]

Reference： [1]Journal of Organic Chemistry,2010,vol. 75,p. 5421 - 5424

21
[ 1217-89-6 ]
[ 937-41-7 ]
[ 1263090-12-5 ]
[ 1295592-92-5 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of phosphinothiourea 1b (0.02 mmol) in THF (1.0 mL) was added acrylate (0.4 mmol) at 0 C. After 10 min stirring at this temperature, isatin (0.2 mmol) was added. The reaction mixture was stirred at 0 C (monitoring by TLC). Then the resulting solution was concentrated under reduced pressure and the residue was purified by a flash column chromatography on silica gel to afford the desired adducts and the ee values were determined by HPLC analysis with chiral column.

Reference： [1]Chemistry - A European Journal,2010,vol. 16,p. 13617 - 13621
[2]Tetrahedron,2011,vol. 67,p. 2974 - 2978

22
[ 2058-74-4 ]
[ 937-41-7 ]
C₁₈H₁₅NO₄ [ No CAS ]
[ 1295592-75-4 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: To a solution of phosphinothiourea 1b (0.02 mmol) in THF (1.0 mL) was added acrylate (0.4 mmol) at 0 C. After 10 min stirring at this temperature, isatin (0.2 mmol) was added. The reaction mixture was stirred at 0 C (monitoring by TLC). Then the resulting solution was concentrated under reduced pressure and the residue was purified by a flash column chromatography on silica gel to afford the desired adducts and the ee values were determined by HPLC analysis with chiral column.

Reference： [1]Tetrahedron,2011,vol. 67,p. 2974 - 2978

23
[ 1174908-08-7 ]
[ 937-41-7 ]
C₂₀H₂₈O₂Si [ No CAS ]
[ 1303459-41-7 ]

Yield	Reaction Conditions	Operation in experiment
76%	With [Rh(OH)(cod)]2; In toluene; at 80℃; for 24h;Inert atmosphere;	To a solution of [Rh(OH)(cod)]2 (2.3 mg, 0.0050 mmol, 2 mol % of Rh) in toluene (0.5 mL) were added propargylic alcohol 1 (0.50 mmol) and acrylate ester 2 (1.50 mmol, 3 equiv), and the mixture was heated at 80 C for 24 h. The reaction mixture was passed through a pad of silica gel with Et2O, and it was concentrated on a rotary evaporator. The residue was subjected to preparative TLC (silica gel) or flash column chromatography (silica gel) with hexane/ethyl acetate to give product 3.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2185 - 2187

24
[ 4545-20-4 ]
[ 937-41-7 ]
[ 1402416-35-6 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 5338 - 5341,4

25
[ 138853-66-4 ]
[ 937-41-7 ]
[ 1415230-87-3 ]
[ 1415231-03-6 ]

Yield	Reaction Conditions	Operation in experiment
28%; 47%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 24h;	General procedure: 1 (0.5 mmol), alpha, beta-unsaturated carbonyl 2 (1.0 mmol) and DBU (0.1 mmol) were dissolved in CH2Cl2 (2 mL), and then the reaction mixture was stirred at room temperature. After the reaction was completed, the mixture was directly charged onto silica gel and purified through flash chromatography to furnish the corresponding product 3 and 4.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6650 - 6653

26
[ 937-41-7 ]
[ 1412907-25-5 ]
[ 1415230-93-1 ]
[ 1415231-09-2 ]

Yield	Reaction Conditions	Operation in experiment
27%; 48%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20℃; for 24h;	General procedure: 1 (0.5 mmol), alpha, beta-unsaturated carbonyl 2 (1.0 mmol) and DBU (0.1 mmol) were dissolved in CH2Cl2 (2 mL), and then the reaction mixture was stirred at room temperature. After the reaction was completed, the mixture was directly charged onto silica gel and purified through flash chromatography to furnish the corresponding product 3 and 4.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6650 - 6653

27
[ 937-41-7 ]
[ 98-80-6 ]
[ 2757-04-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With C8H20N2O2Pd*2C2H4O2; In N,N-dimethyl-formamide; at 50℃; for 3h;	General procedure: Under air atmosphere, a mixture of olefin (0.5 mmol), arylboronic acid (1.0 mmol), alkoxopalladium complex (4 mg, 2 mol %), oxidant (1.0 mmol) and DMF (1.5 mL) was stirred at 50 C for 3 h. The reaction mixture was cooled to room temperature, and then directly purified by preparative thin layer chromatography on silica gel using petroleum ether/ethyl acetate as an eluent to give desired compounds.

Reference： [1]Tetrahedron,2013,vol. 69,p. 5123 - 5128

28
[ 1271-86-9 ]
[ 937-41-7 ]
C₂₂H₂₃FeNO₂ [ No CAS ]

Reference： [1]Chemical Science,2013,vol. 4,p. 2675 - 2679

29
[ 16078-30-1 ]
[ 937-41-7 ]
[ 1603838-16-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 929 - 933

30
[ 937-41-7 ]
[ 38604-68-1 ]
[ 1604806-84-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 2494 - 2497
[2]Organic and Biomolecular Chemistry,2014,vol. 12,p. 5469 - 5476

31
[ 937-41-7 ]
[ 10354-51-5 ]
[ 1610422-43-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 3142 - 3145

32
[ 421-83-0 ]
[ 937-41-7 ]
phenyl 2-chloro-4,4,4-trifluorobutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With pyridine; copper dichloride; In 1,4-dioxane; at 100℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: CuCl2 (7 mg, 10 mol%), alkene (0.5 mmol), 1,4-dioxane (2 mL), CF3SO2Cl (152 mg, 1.8 eq.) and pyridine (4 mg, 10 mol%) were added into a Schlenk tube under a N2 atmosphere. The reaction mixture was stirred at 100 C for 1 h. After being cooled to room temperature, the solid was removed by filtration and washed with DCM (30 mL). The combined organic solution was evaporated, and the resulting crude product was purified by flash column chromatography to give the products 3 or 4.

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 4246 - 4249
Angew. Chem.,2015,vol. 127,p. 4320 - 4323
[2]Organometallics,2018,vol. 37,p. 3928 - 3935
[3]Journal of Fluorine Chemistry,2018,vol. 215,p. 25 - 31

33
[ 937-41-7 ]
5-nitro-2-((trifluoromethyl)thio)isoindoline-1,3-dione [ No CAS ]
phenyl 3-(5-nitro-1,3-dioxoisoindolin-2-yl)-2-((trifluoromethyl)thio)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 1,4-diaza-bicyclo[2.2.2]octane; In 1,4-dioxane; dichloromethane; at 20℃; for 40h;	N- trifluoromethylthio-4-nitro phthalimide (65.7mg, 0.225mmol), 1- acrylate, phenyl (22.2mg, 0.15mmol), DABCO (8.75mg, 0.075mmol) and di a mixed solution of methylene chloride and 1,4-dioxane: mixture (volume ratio 1 1,0.45mL) was stirred at room temperature for 40 hours.Concentrated under reduced pressure, by column chromatography to give product 1- (4-nitro-phthalimide) -2-trifluoromethylthio - phenyl propionate, 80% isolated yield.

Reference： [1]Organic Letters,2015,vol. 17,p. 6090 - 6093
[2]Patent: CN105523988,2016,A .Location in patent: Paragraph 0153; 0154; 0155; 0156; 0157; 0158

34
[ 88070-48-8 ]
[ 937-41-7 ]
C₁₇H₁₅NO₃ [ No CAS ]

Reference： [1]ACS Catalysis,2016,vol. 6,p. 230 - 234

35
[ 937-41-7 ]
[ 57479-70-6 ]
phenyl 2-(6-chloro-4-methoxy-3-oxo-1,3-dihydroisobenzofuran-1-yl)acetate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2016,vol. 11,p. 356 - 359

36
[ 937-41-7 ]
[ 2926-29-6 ]
phenyl 4,4,4-trifluorobutanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With [4,4?-bis(1,1-dimethylethyl)-2,2?-bipyridine-N1,N1?]bis [3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-N]phenyl-C]iridium(III) hexafluorophosphate; In methanol; at 20 - 25℃; for 24h;Irradiation; Schlenk technique; Inert atmosphere;	The unreacted olefin I-15 was added to a 10 mL Schlenk tube(R1 = phenolic ester, R2 = hydrogen, n = 0) (37.0 mg, 0.25 mmol)Sodium trifluoromethanesulfinate(78.0 mg, 0.50 mmol) and Ir [dF (CF3) ppy] 2 (dtbbpy) PF6 (5.6 mg, 0.005 mmol).After evacuation of argon, 3 mL of solvent (methanol) was added, and the reaction was carried out by stirring the fluorescent lamp with a Schuling tube.Fluorescent wavelength range of visible light, power 36W, the reaction temperature is room temperature, the reaction time is 24 hours.After completion of the reaction, the reaction was quenched by adding water to the system and extracting with ethyl acetate (3 x 10 mL). The organic phase was separated, dried over anhydrous Na2SO4, filtered and the solvent was removed by rotary evaporation.The residue was purified by column chromatography on ethyl acetate / petroleum ether = 1: 20 to give the desired product II-1532 mg in 58% yield.

Reference： [1]Chemical Communications,2016,vol. 52,p. 6371 - 6374
[2]Patent: CN106892800,2017,A .Location in patent: Paragraph 0132; 0133; 0134; 0135; 0136; 0137; 0138

37
[ 937-41-7 ]
[ 107-12-0 ]
phenyl 4-cyanopentanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
52%Spectr.	With C25H42MnNO2P2; In neat (no solvent); at 20℃; for 26h;	A stock solution containing 5 mg / mL (O.Olmmol / mL) of c-[Mn(PNP*tBu)(CO)2] (2) in the particular reaction media (solvent: C6,THF, DCM, or -pentane) was prepared. To 0.5 mL of the stock solution (0.005 mmol catalyst) 1 mmol of nitrile is added followed by the addition of 1 mmol of the specific alpha,beta-unsaturated compound. The mixture stirred at room temperature (-22 C) for the indicated time and quenched by introduction of non-dried -pentane. The yield was determined by integration of lH NMR signals with respect to the suitable standard either toluene for the reaction in THF, dichloromethane, and -pentane, or dioxane for C6 (done before quenching). The products were purified according to the indicated method, isolated yields are reported.

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 6985 - 6997
[2]Patent: WO2017/137984,2017,A1 .Location in patent: Paragraph 00308; 00311

38
[ 937-41-7 ]
[ 6630-33-7 ]
(E)-3-(2-formylphenyl)acrylic acid phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With bis-triphenylphosphine-palladium(II) chloride; triethylamine; In dimethyl sulfoxide; at 100℃; for 15h;Inert atmosphere;	General procedure: A solution of aryl bromide (1mmol, 1equiv), acrylate (2equiv), PdCl2(PPh3)2 (5mol%) and Et3N (5equiv) in DMSO (2mL) under argon was heated at 100C for 15h. Water (10mL) was then added followed by sodium chloride (until saturation) and the reaction mixture was extracted with ethyl acetate (3×15mL). The organic layers were combined and washed with brine, dried over MgSO4, filtered and the solvent was removed under reduced pressure. The residue was purified on a column of silica gel to afford the desired pure coupling product. 4.2.6 (E)-3-(2-Formylphenyl)<strong>[937-41-7]acrylic acid phenyl ester</strong> 11e General Heck procedure using 2-bromobenzaldehyde 16 (185 mg, 1 mmol, 2 equiv) and <strong>[937-41-7]phenyl acrylate</strong> 19e (296 mg, 2 mmol, 2 equiv) affords 11e (86 mg, 0.34 mmol, yield = 34%) as a colorless oil. 1H NMR (300 MHz, CDCl3): delta = 10.20 (s, 1H), 8.65 (d, J = 15.9 Hz, 1H), 7.83-7.72 (m, 1H), 7.65-7.46 (m, 3H), 7.36-7.26 (m, 2H), 7.19-7.06 (m, 3H), 6.48 (d, J = 15.9 Hz, 1H); 13C NMR (75 MHz, CDCl3): delta = 191.8, 164.6, 150.8, 143.1, 136.2, 134.0 (2 signals), 132.8, 130.3, 129.5 (2C), 128.1, 125.9 (2C), 122.2, 121.6; HRMS (ESI+) m/z calcd for C16H13O3 [MH]+ 253.08592, found 253.08644.

Reference： [1]Tetrahedron Asymmetry,2016,vol. 27,p. 980 - 989
[2]Journal of the American Chemical Society,2016,vol. 138,p. 8968 - 8975

39
[ 937-41-7 ]
[ 3912-46-7 ]
bis[9-(2-phenoxycarbonyl-ethyl)fluoren-9-yl]methane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		To 50mL three-necked flask, Bis (fluoren-9-yl) methane(Compound 1) 1.00 g (2.9 mmol), tetrabutylammonium bromide 93 mg (0.29 mmol), 5mL THF were added & under a nitrogen atmosphere, it was stirred at roomtemperature. 50wt / wt% sodium hydroxide aqueous solution 0.40 mL was added andstirred for 15 minutes and then cooled to 3 C in an ice bath. Herein, <strong>[937-41-7]phenylacrylate</strong> 0.945 g (6.38 mmol) was added dropwise over 3 minutes, then agedsubsequently for 2 hours. This reaction solution was neutralized with 3Nhydrochloric acid and the desired compound was extracted with ethyl acetate20mL, then the aqueous and organic phases were separated. Bis [9- (2-phenoxycarbonyl ethyl) fluoren-9-yl] methane (Compound 2) in the organic phasewas determined by HPLC (44% yield).

Reference： [1]Patent: JP2015/199679,2015,A .Location in patent: Paragraph 0149-0151

40
[ 102-09-0 ]
[ 79-10-7 ]
[ 937-41-7 ]

Yield	Reaction Conditions	Operation in experiment
59%	With dmap; oxygen; phenol; at 130 - 140℃; for 9h;	Example 28 In a 50 mL three-neck glass flask equipped with an air inlet, added were 6.5 grams (90 mmol) of acrylic acid, 16.0 grams (75 mmol) of diphenyl carbonate, 0.5 grams (4 mmol) of 4-dimethylaminopyridine as a catalyst, 0.004 grams of phenol as a polymerization inhibitor, and 1.3 grams (7 mmol) of diphenyl ether as an internal standard substance. While air was being blown into the mixture at a rate of 10 mL/min, the mixture was heated to an internal temperature of 130 C. and stirred for 6 hours. Then the mixture was heated to an internal temperature of 140 C. and stirred for 3 hours. As a result, the amount of produced phenyl acrylate was 6.5 grams (44 mmol). The yield of phenyl acrylate relative to diphenyl carbonate was 59%. From the example above, it is found that phenyl ester is obtained efficiently even when the material is changed from methacrylic acid to acrylic acid.
49%	With magnesium monohydroxide; phenol; at 135℃; for 12h;	Three-necked glass flask equipped with an air inlet tube of 50mL,Acrylic acid 12.1g (168mmol), diphenyl carbonate, 12.0g (56mmol), as a catalyst, from the magnesium hydroxide 0.34g (6mmol), a phenol 0.01g, internal standard as a polymerization inhibitor in diphenylWere placed 0.95g (5mmol). While blowing the air at a flow rate of 10mL per minute to the mixed solution, the internal temperature is stirred for 12 hours, heated to 135 haetdayi result, the resulting phenyl-acrylate was 4.1g (28mmol). The yield of the diphenyl carbonate to phenyl acrylate was 49%

Reference： [1]Patent: US2016/244396,2016,A1 .Location in patent: Paragraph 0094-0096
[2]Patent: KR2016/43010,2016,A .Location in patent: Paragraph 0190-0192

41
[ 19012-02-3 ]
[ 937-41-7 ]
phenyl (E)-3-(3-acetyl-1-methyl-1H-indol-2-yl)acrylate [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5496 - 5499

42
1-methyl-4-(3-phenoxyprop-1-ynyl)benzene [ No CAS ]
[ 937-41-7 ]
C₂₅H₂₀O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With dipotassium peroxodisulfate; tetrakis(triphenylphosphine) palladium(0); In acetonitrile; at 50℃; for 10h;Sealed tube;	To the screw-in test tube was added 0.25 mmol of phenyl-p-tolyl propynyl ether,0.35 mmol of <strong>[937-41-7]phenyl acrylate</strong>, 0.050 mmol of tetrakistriphenylphosphine palladium,0.50 mmol potassium persulfate, 2 ml acetonitrile,After the reaction was stirred at 50 C for 10 hours, heating and stirring were stopped, and the mixture was cooled to room temperature. The reaction material was evaporated under reduced pressure to remove the solvent, and then purified by column chromatography.To give 2-H-benzopyran derivatives,The column chromatography eluent used was a mixture of petroleum ether and ethyl acetate in a volume ratio of 25: 1,Yield 86%.

Reference： [1]Patent: CN106243073,2016,A .Location in patent: Paragraph 0104-0112

43
[ 617-86-7 ]
[ 75-91-2 ]
[ 937-41-7 ]
C₁₉H₃₂O₄Si [ No CAS ]

Reference： [1]ACS Catalysis,2017,vol. 7,p. 7120 - 7125

44
[ 937-41-7 ]
[ 52457-01-9 ]
C₁₆H₁₄O₂ [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 1213 - 1217

45
[ 937-41-7 ]
phenyl 2,3-dihydroxypropanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		General procedure: Imidazolium chloride QAS-2 (0.5 mmol) and alkene (5.0 mmol) were mixed in acetone (10 mL) and the mixture was stirred at r.t. for 10 mins. Then the mixture was cooled to 0 C and KMnO4 (6.0 mmol) was added in portions. The resulting mixture was stirred for further 2 h at 0-5 C. TLC indicated complete consumption of the alkene. Aq NaHSO3 (10 mL) was added in one portion to quench the reaction. The mixture was filtered on Celite, washed thoroughly with acetone. The combined filtrate was concentrated under reduced pressure and the residue was extracted with EtOAc (3 × 10 mL). The organic phase was dried (Na2SO4), filtered, and evaporated to dryness. The crude product was purified by column chromatography (silica gel).

Reference： [1]Synthesis,2018,vol. 50,p. 1815 - 1819

46
[ 201230-82-2 ]
[ 937-41-7 ]
[ 146397-87-7 ]
C₁₇H₁₁F₃O₃ [ No CAS ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 5074 - 5077

47
[ 937-41-7 ]
[ 5720-05-8 ]
[ 637-27-4 ]
[ 1104411-64-4 ]

Yield	Reaction Conditions	Operation in experiment
37%; 43%Spectr.	With ruthenium (III) nanoparticles stabilized on linear polystyrene; In water; at 90℃; for 5h;Sealed tube;	General procedure: To a screw-capped vial with a stirring bar were added PSRh(III)NPs (3.0 mg, 2.5 mol% of Rh), 4-methylphenylboronic acid(68.0 mg, 0.5 mmol), butyl acrylate (153.8 mg, 1.2 mmol), and H2O(1 mL). After stirring at 90 C for 5 h, the reaction mixture wascooled to room temperature by immediately immersing the vial inwater (~20 C) for about 10 min. After separating the catalyst andthe aqueous phase by centrifugation, the aqueous phase was decanted.Recovered catalyst was washed with H2O (5 x 3.0 mL) anddiethyl ether (5 x 3.0 mL), which were then added to the aqueousphase. The aqueous phase was extracted eight times with diethylether. The combined organic extracts were dried over MgSO4 andconcentrated under reduced pressure. The productwas analyzed by1H NMR. The recovered catalyst was dried in vacuo and reused.Furthermore, the amount of Rh metal in the aqueous phasedetermined by ICP-AES analysis was 1.6 ppm.

Reference： [1]Journal of Organometallic Chemistry,2018,vol. 873,p. 1 - 7

48
N-methyl-3-cyclohexylthio-1H-indole [ No CAS ]
[ 937-41-7 ]
phenyl (E)-3-(3-(cyclohexylthio)-1-methyl-1H-indol-4-yl)acrylate [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 4898 - 4901

49
[ 96-54-8 ]
[ 937-41-7 ]
(E)-phenyl 3-(1-methyl-1H-pyrrol-2-yl)acrylate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2018,vol. 13,p. 2418 - 2422

50
[ 932-16-1 ]
[ 937-41-7 ]
(E)-phenyl-3-(5-acetyl-1-methyl-1H-pyrrol-2-yl)acrylate [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2018,vol. 13,p. 2418 - 2422

51
[ 1033462-77-9 ]
[ 108-95-2 ]
[ 937-41-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With caesium carbonate; at 25℃; for 3h;	General procedure: 0.226 g (2.4 mmol, manufactured by Kanto Chemical Co., Inc.) of phenol and a compound represented by formula (I) (R1 is CH3, R2 is CH(CH3)2) (0.413 g, 2.4 mmol) were sequentially added, and the reaction was carried out at 80 C. under stirring,Phenyl methacrylate was produced.The reaction results after 7 hours from the start of the reaction are shown in Table 1.

Reference： [1]Patent: JP2018/154619,2018,A .Location in patent: Paragraph 0019; 0020; 0024

52
C₇H₁₀O₄ [ No CAS ]
[ 108-95-2 ]
[ 937-41-7 ]

Yield	Reaction Conditions	Operation in experiment
96%	With caesium carbonate; at 25℃; for 3h;	General procedure: 0.226 g (2.4 mmol, manufactured by Kanto Chemical Co., Inc.) of phenol and a compound represented by formula (I) (R1 is CH3, R2 is CH(CH3)2) (0.413 g, 2.4 mmol) were sequentially added, and the reaction was carried out at 80 C. under stirring,Phenyl methacrylate was produced.The reaction results after 7 hours from the start of the reaction are shown in Table 1.

Reference： [1]Patent: JP2018/154619,2018,A .Location in patent: Paragraph 0019; 0020; 0023

53
[ 591-50-4 ]
[ 937-41-7 ]
[ 2757-04-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 1.5h;Inert atmosphere; Green chemistry;Catalytic behavior;	General procedure: Screening reactions were carried out in 25 mL round bottomflask. Iodobenzene (200 mg, 1 equivalent), methyl acrylate(1.1 equivalents), catalyst (10 mg) and K2CO3 (1.5 equivalent)were taken into a 25 mL round bottom flask. 3 mL ofDMF was added. The reaction was kept under an argon atmosphereat 110 C. Reaction was monitored by TLC. Extractedthe product with diethyl ether and 3 times water work up.Percentage of yield was determined by using gas chromatography.Heck coupling reactions were done in the speciallydesigned reaction flask. Aryl halides (2 g, 1 equivalent),olefins (1.1 equivalents) and base (1.5 equivalents) were takeninto the reaction flask. Catalyst coated cordierite monolithwasput inside the flask. The reaction was kept under an argonatmosphere at 110 C. The reaction was monitored by TLC.After completion of the reaction, the coupled product wasextracted by diethyl ether and washed 3 times with water toremove the solvents and base. Catalyst coated monolith wasremoved from the flask, washed with water to remove solventand base. Then washed with n-hexane to remove organicimpurities and dried in a hot air oven for 2 h at 200 C. Driedcatalyst cartridge was reused for two more substrates of Heckcoupling reactions. The product was isolated using column chromatography.The eluents used were pet ether and ethyl acetate. The ratiowas standardised by usingTLCaccording to the polarity of theproducts. Coupled products were characterized by 1H NMR,13C NMR, IR spectra and mass spectra.

Reference： [1]Journal of Chemical Sciences,2019,vol. 131

54
[ 937-41-7 ]
[ 53554-11-3 ]
phenyl 3-(6-oxodibenzo[d,f][1,3,2]dioxaphosphepin-6-yl)propanoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With triethylamine; In chloroform;Reflux;	General procedure: In a 1000 mL round-bottom flask equipped with condenser and magnetic stirring bar, 1 (210.0 g, 0.90 mol), the appropriate acrylate (0.90 mol) and triethyl amine (11.0 mL, 0.09 mol) were dissolved in chloroform (260 mL). The solution was heated to reflux and stirredat that temperature overnight. After cooling down, water (200 mL) and conc. HCl (7.5 mL) were added to the solution and stirred for 30 min. The organic layer was separated and dried with sodium sulfate. After removing the solvent the product was dried under reduced pressure. The chemical structures are outlined in Schemes 5-10.

Reference： [1]Tetrahedron,2019,vol. 75,p. 1306 - 1310

55
3-allyl-1,5-diphenylpentane-1,5-dione [ No CAS ]
[ 937-41-7 ]
phenyl (E)-7-oxo-5-(2-oxo-2-phenylethyl)-7-phenylhept-2-enoate [ No CAS ]