[ CAS No. 643-65-2 ] {[proInfo.proName]}

Name: 643-65-2|3-Methylbenzophenone|98%
Brand: Ambeed
SKU: A312712
Price: 9.0 USD
Availability: InStock
Rating: 95 (26 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

2D 3D

Structure of 643-65-2 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 643-65-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 643-65-2 ]

SDS Specification

Alternatived Products of [ 643-65-2 ]

Product Details of [ 643-65-2 ]

CAS No. :	643-65-2	MDL No. :	MFCD00008535
Formula :	C₁₄H₁₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	URBLVRAVOIVZFJ-UHFFFAOYSA-N
M.W :	196.24	Pubchem ID :	69511
Synonyms :

Calculated chemistry of [ 643-65-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.07
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	61.28
TPSA :	17.07 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.79 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.44
Log Po/w (XLOGP3) :	3.81
Log Po/w (WLOGP) :	3.23
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	3.91
Consensus Log Po/w :	3.33

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.92
Solubility :	0.0238 mg/ml ; 0.000121 mol/l
Class :	Soluble
Log S (Ali) :	-3.86
Solubility :	0.0269 mg/ml ; 0.000137 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.25
Solubility :	0.00109 mg/ml ; 0.00000557 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.42

Safety of [ 643-65-2 ]

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 [ 643-65-2 ]

* 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 [ 643-65-2 ]
Downstream synthetic route of [ 643-65-2 ]

[ 643-65-2 ] Synthesis Path-Upstream 1~1

1
[ 643-65-2 ]
[ 22071-22-3 ]

Reference： [1] Chemical Communications, 2000, # 21, p. 2147 - 2148
[2] Journal of Medicinal Chemistry, 1984, vol. 27, # 12, p. 1682 - 1690

[ 643-65-2 ] Synthesis Path-Downstream 1~41

1
[ 643-65-2 ]
[ 620-47-3 ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 6331 - 6333
[2]Chemical and Pharmaceutical Bulletin,2006,vol. 54,p. 1304 - 1307
[3]Organic Letters,2014,vol. 16,p. 2000 - 2002
[4]Journal of the American Chemical Society,1959,vol. 81,p. 3320
[5]Journal of the American Chemical Society,1959,vol. 81,p. 3320
[6]Journal of the American Chemical Society,1959,vol. 81,p. 3320
[7]Chemische Berichte,1879,vol. 12,p. 2300
[8]Journal of the American Chemical Society,1959,vol. 81,p. 3320
[9]Bulletin of the Chemical Society of Japan,1985,vol. 58,p. 688 - 697
[10]Journal of Medicinal Chemistry,2005,vol. 48,p. 6461 - 6471
[11]Advanced Synthesis and Catalysis,2018,vol. 360,p. 2522 - 2536
[12]Chemical Communications,2019,vol. 55,p. 12968 - 12971

2
[ 643-65-2 ]
[ 22071-24-5 ]

Yield	Reaction Conditions	Operation in experiment
77%	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 75℃; for 6.5h;	Commercially available 3-methylbenzophenone (4.00 g, 20.4 mmol) was dissolved in carbon tetrachloride (100 mL), and N-bromosuccinimide (4.71 g, 26.5 mmol) and 2,2'-azobisisobutyronitrile (1.00 g, 6.09 mmol) was added to the solution, followed by stirring at 75C for 6.5 hours. After the reaction mixture was cooled, the precipitates were filterd out. The filtrate was combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:20) to obtain 3-bromomethylbenzophenone (4.31 g, yield 77%).
66%	With N-Bromosuccinimide; azobisisobutyronitrile; In tetrachloromethane;Reflux;	A solution of phenyl(m-tolyl)methanone (2.0 g omopyrrolidine-2,5-dione (2.0 g, 11 mmol), and (E)-2,2'-(diazene-1,2-diyl)bis(2-methylpropanenitrile) (0.167 g, 1.02 mmol) in CCl4 (60 mL) was refluxed overnight. After cooling to room temperature, the reaction mixture was washed with water (3 x 20 mL), dried, and concentrated under vacuum. The residue was applied to a silica gel column and eluted with ethyl acetate/hexane, 1:20 to give (3-(bromomethyl)phenyl)(phenyl)methanone (1.85 g, 6.73 mmol, 66% yield) as a white solid. LCMS m/z = 274.8 [M+H]+.
32.3%	With bromine; In tetrachloromethane; at 0 - 80℃; for 24.5h;	Intermediate 1 : [3-(Bromomethyl) phenyl] (phenyl) methanoneTo a 1000 mL RB flask fitted with magnetic stirrer, was charged with 375 mL of CCI4. The solvent was cooled to 0 "C and to the stirred solvent was added phenyl-m-to lyl- methanone (15.0 g, 76.45 mmol) followed by the addition of bromine (24.43 g, 152.9 mmol) at 0 and the mixture was allowed to stir at the sam e temperature for 30 minutes. The resulting solution was refluxed at 80 C for 24 h. After completion of the reaction (reaction monitored by TLC), RM was cooled to 10 C and quenc hed with the addition of solid sodium bicarbonate (15 g, 178.57 mmol). The organic layer was washed with saturated sodium bicarbonate solution (300 mL X 2) and saturated brine solution (300 mL). The organic layer was dried over anhydrous Na2S04 and the solvent was removed under reduced pressure to get the product as a white solid (6.8 g, Yield: 32.3 %): H N R (300MHz, CDCI3): delta 7.74- 7.76(m, 2H), 7.71-7.72(t, 2H), 7.51-7.67(m, 2H), 7.40-7.45(m, 3H), 4.46(s, 2H).

	With bromine; In tetrachloromethane;	(b) 39.2 g (0.2 mol) of 3-methylbenzophenone and 38.4 g (0.24 mol) of bromine were stirred at reflux in 1 l of carbon tetrachloride for 8 hours. After distillation of the solvent in a water-jet vacuum the crude product obtained was chromatographed on 500 g of silica gel with hexane and methylene chloride. The thus-purified product was recrystallized from n-hexane. There were thus obtained 21.76 g (40% of theory) of (3-bromomethyl-phenyl)-phenyl-methanone in the form of colourless crystals; MS: 274, 276 (M)+.
	With bromine; In ethylene dibromide;	3-bromomethylbenzophenone is prepared by dissolving 3-methylbenzophenone (95 g.) in ethylene bromide (200 cc.), heating the solution under reflux, and adding a solution of bromine (79 g.) in ethylene bromide (60 cc.) over a period of 3 hours in the presence of ultra-violet light. Heating under reflux is continued for 30 minutes, and the product is concentrated to dryness under reduced pressure (20 mm. Hg) to give 3-bromomethylbenzophenone in the form of an oil in quantitative yield. 3-methylbenzophenone is prepared in accordance with E. Ador and A.A. Rilliet, Ber., 12, 2298 (1879).
6.8 g	With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); In tetrachloromethane; at 80℃; for 0.8h;Inert atmosphere;	The 250 ml three-necked flask was thoroughly dried, passed through a nitrogen gas, and connected to a drying tube, followed by 9.81 g. 5-methylbenzophenone, 150ml of carbon tetrachloride, slowly warm to 80 C, stir reflux, add NBS and AIBN into the flask in three batches.The time interval is 0.8h, It was monitored by TLC until the reaction was completed, naturally cooled to room temperature, washed once with 0.05 mol/L sodium thiosulfate solution, twice with deionized water, filtered, and steamed. It was poured into absolute ethanol and recrystallized and dried to give 6.8 g of white solid.

Reference： [1]Patent: EP1724271,2006,A1 .Location in patent: Page/Page column 64
[2]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 1483 - 1486
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 3892 - 3896
Angew. Chem.,2017,vol. 129,p. 3950 - 3954,5
[4]Patent: WO2017/216726,2017,A1 .Location in patent: Page/Page column 839
[5]Patent: WO2012/11125,2012,A1 .Location in patent: Page/Page column 59; 60
[6]Collection of Czechoslovak Chemical Communications,1968,vol. 33,p. 3213 - 3226
[7]Journal of Medicinal Chemistry,1984,vol. 27,p. 1682 - 1690
[8]Phosphorus and Sulfur and the Related Elements,1988,vol. 35,p. 77 - 82
[9]Organic Letters,2005,vol. 7,p. 3387 - 3389
[10]Phytochemistry,2007,vol. 68,p. 407 - 415
[11]Chemical Communications,2000,p. 2147 - 2148
[12]Journal of Medicinal Chemistry,2007,vol. 50,p. 3420 - 3422
[13]Patent: US6051712,2000,A
[14]Patent: EP485158,1992,A2
[15]Physical Chemistry Chemical Physics,2007,vol. 9,p. 3268 - 3275
[16]Bioorganic and Medicinal Chemistry,2009,vol. 17,p. 4797 - 4805
[17]Journal of Organic Chemistry,2011,vol. 76,p. 3710 - 3719
[18]Patent: CN109305900,2019,A .Location in patent: Paragraph 0025; 0028

3
[ 16444-45-4 ]
[ 643-65-2 ]

Reference： [1]Synthesis,1996,p. 1109 - 1114

4
[ 17933-03-8 ]
[ 98-88-4 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With [Pd(eta(5)-C5H5)Fe(eta(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)]; potassium carbonate; In toluene; at 60℃; for 12h;Inert atmosphere;	General procedure: A reaction vessel was charged with a mixture of phenylboronic acid (0.5 mmol), K2CO3 (1.0 mmol), catalyst 2 (0.5 mol %) in toluene (2.0 mL), and stirred for about 20 min under nitrogen atmosphere. Then benzoic anhydride or benzoyl chloride was then added. The mixture was heated to 60 C and incubated in an oil bath at 60 C for 12 h under nitrogen atmosphere. After the completion of the reaction, the mixture was quenched by 5 mL water and then extracted with ethyl acetate (3×10 mL). The combined organic layer was dried over MgSO4. After removal of the solvent in vacuo, the product was obtained by purifying on preparative TLC, eluting with ethyl acetate/petroleum ether and the yield was calculated based on the phenylboronic acid (the purified products were identified by NMR spectra and comparison of the melting points with the literature data). In the recycle experiment, the residue was subjected to a second run of the acylation reaction by charging with the same substrates (benzoic anhydride or benzoyl chloride, phenylboronic acid, dioxane, and K2CO3) without further addition of cyclopalladated catalyst 2.
84%	With 2C60H80NaO12(2+)*Cl6Pd2(2-); potassium carbonate; triphenylphosphine; In toluene; at 70℃; for 12h;	General procedure: A 5 mL flask charged with benzoyl chloride (1.0 mmol), arylboronic acid (0.5 mmol),K2CO3 (1.0 mmol), complex 1 (0.5 mol%, 3.1 mg), PPh3 (0.01 mmol, 1.3 mg) and toluene (2.0mL) was put into a preheated 70 oC oil bath for an appropriate period of time under air. After thereaction was finished, the reaction mixture was cooled to room temperature, filtered through ashort silica column and washed with ethyl acetate. Then the combined filtrates were concentratedin vacuo and the residue was purified by flash chromatography (eluent: ethylacetate/petroleumether). All the products were known compounds and characterized by comparing mp, 1H NMRand 13C NMR spectra with literature.
82%	With C30H38Cl2N8Pd(2+)*2Cl(1-); sodium carbonate; In water; acetone; at 60℃; for 12h;	General procedure: The catalyst (3.8 mg, 1.0 mol%), Na2CO3 (170 mg, 1.6 mmol), H2O (1.5 mL) and acetone (1.5 mL) was added into a 25 mL schlenk flask, then the reactor was stirred at room temperature for several minutes to dissolve the catalyst and base homogenously. Subsequently, benzoyl chloride (1.0 mmol) and boronic acid (1.2 mmol) were introduced. Then the flask was immersed in an oil bath preheated at 60 C for 12 h. After the reaction was completed, the mixture was extracted with diethyl ether, and the combined organic layer was dried over anhydrous Na2SO4 and was subsequently purified by flash chromatography using silica gel (petroleum ether/ethyl acetate = 20:1) yielding the desired products.

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3057 - 3060
[2]Russian Chemical Bulletin,2004,vol. 53,p. 364 - 369
[3]Organometallics,2014,vol. 33,p. 4131 - 4147
[4]Tetrahedron Letters,2003,vol. 44,p. 271 - 273
[5]Organometallics,2018,vol. 37,p. 1615 - 1626
[6]Tetrahedron,2012,vol. 68,p. 2283 - 2288
[7]Applied Organometallic Chemistry,2018,vol. 32
[8]ARKIVOC,2013,vol. 2013,p. 251 - 271
[9]Russian Chemical Bulletin,1997,vol. 46,p. 1631 - 1632
[10]Tetrahedron Letters,2011,vol. 52,p. 3897 - 3901
[11]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 288 - 296
[12]Tetrahedron,2006,vol. 62,p. 11675 - 11678
[13]Organometallics,2016,vol. 35,p. 3378 - 3387

5
[ 643-65-2 ]
[ 27428-63-3 ]

Yield	Reaction Conditions	Operation in experiment
74.4%	With hydroxylamine hydrochloride; sodium acetate; acetic acid; at 80℃; for 3h;	Intermediate 20: {£, Z)-N-Hydroxy-1-(3-methylphenyl)-1-phenylmethanimineTo a 100 mL RB flask fitted with magnetic stirrer was charged 20 mL of acetic acid. To the stirred solvent was added (3-methylphenyl) (phenyl) methanone (2 g, 10 mmol) and sodium acetate (1.06 g, 1.3 eq). Then it was stirred for 5 min, hydroxylamine hydrochloride (0.89 g, 1.2 eq) was added. The RM heated 80 fo r 3 h. After completion of the reaction (reaction monitored by TLC), RM poured into water (75 mL) and extracted with ethyl acetate (50 mL X 2). The organic layer was washed with saturated brine solution (40 mL), dried over anhydrous Na2S04 and evaporated to dryness and purified by silica gel (100/200 mesh), using petroleum ether (60-80) and ethyl acetate gave title compound (1.6 g, yield: 74.4%); MS (ESI, 120 eV) : m/z = 212.1 (M+H)+; H NMR (300MHz, DMSO-d6): delta 11.27-11.28(d, 1 H), 7.04- 7.48(m, 9H), 2.27-2.33(d, 3H).

Reference： [1]Bioorganic and Medicinal Chemistry,2000,vol. 8,p. 1139 - 1149
[2]Patent: WO2012/11125,2012,A1 .Location in patent: Page/Page column 73-74
[3]Journal of Chemical Research - Part S,2001,p. 446 - 449
[4]Advanced Synthesis and Catalysis,2019,vol. 361,p. 3137 - 3145

6
[ 17933-03-8 ]
[ 93-97-0 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With NHC-Pd(II)-Im; sodium hydrogencarbonate; In water; at 20℃; for 12h;Inert atmosphere;	General procedure: Under N2 atmosphere, NaHCO3 (2.4 mmol), benzoic anhydride 3a (1.5 mmol), phenylboronic acid 2a (0.75 mmol), and H2O were successively added into a Schlenk reaction tube. The mixture was stirred at room temperature for about 10 min. Then NHC-Pd(II)-Im complex 1 (1.0 mol %) was added. The mixture was stirred at room temperature for 12 h and then was diluted with CH2Cl2, washed with saturated brine, dried over anhydrous Na2SO4. The dried organic phase was then filtered, concentrated under reduced pressure and purified by flash column chromatography on silica gel to give the pure product 4a.

Reference： [1]Tetrahedron,2012,vol. 68,p. 5806 - 5809
[2]Applied Organometallic Chemistry,2011,vol. 25,p. 497 - 501
[3]RSC Advances,2014,vol. 4,p. 53885 - 53890
[4]Chemical Communications,2001,p. 2316 - 2317

7
[ 1711-06-4 ]
[ 98-80-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With copper(I) thiophene-2-carboxylate; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0); In diethyl ether; at 20℃; for 1h;Schlenk technique; Inert atmosphere;	General procedure: 4.3.1 Benzophenone (3a) 18 To phenylboronic acid (1a, 244 mg, 2 mmol), CuTC (191 mg, 1 mmol), Pd(dba)2 (29 mg, 0.05 mmol), and PPh3 (26.2 mg, 0.1 mmol), were added dry Et2O (30 mL) and benzoyl chloride (2a, 116 muL, 1 mmol) at rt and the reaction was monitored by GC and TLC. After completion of the reaction, the reaction mixture was passed briefly through a Celite pad. Further, the pad was washed with Et2O (2*10 mL). The combined organics were concentrated with a rotary evaporator to give a viscous oil or solid. The residue was purified by flash column chromatography on silica gel (hexane/EtOAc=9:1, Rf=0.47), benzophenone (3a) (142 mg, 0.78 mmol, 78%) was obtained as a white solid.

Reference： [1]European Journal of Inorganic Chemistry,2017,vol. 2017,p. 288 - 296
[2]Organometallics,2014,vol. 33,p. 4131 - 4147
[3]Tetrahedron Letters,2008,vol. 49,p. 5773 - 5776
[4]Synlett,2005,p. 2309 - 2312
[5]Tetrahedron,2013,vol. 69,p. 2565 - 2571
[6]Organometallics,2018,vol. 37,p. 1615 - 1626
[7]Tetrahedron Letters,2003,vol. 44,p. 271 - 273

8
[ 17264-86-7 ]
[ 23665-09-0 ]
[ 643-65-2 ]

Reference： [1]Organic Letters,2003,vol. 5,p. 4645 - 4648

9
[ 603-33-8 ]
[ 1711-06-4 ]
[ 643-65-2 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 12917 - 12926
[2]Tetrahedron Letters,2009,vol. 50,p. 4268 - 4271
[3]Tetrahedron Letters,2006,vol. 47,p. 6975 - 6978

10
[ 643-65-2 ]
[ 18355-96-9 ]
dimethyl-(4-phenyl-4-m-tolyl-but-3-enyl)-dimethyl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	Stage #1: (3-dimethylaminopropyl)-triphenylphosphoniumbromide With n-butyllithium In tetrahydrofuran; hexane at 0℃; Stage #2: 3-methyl benzophenone In tetrahydrofuran; hexane at 0 - 20℃; Further stages.;

Reference： [1]Hudgens, Debjani P.; Taylor, Catherine; Batts, Timothy W.; Patel, Manoj K.; Brown, Milton L. [Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 24, p. 8366 - 8378]

11
[ 643-65-2 ]
[ 55095-20-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 78 percent / NH₂OH*HCl; Na₂CO₃ / ethanol / 6 h / Heating 2: H₂ / methanol / 2 h / 2250.18 - 3000.24 Torr

Reference： [1]Sasse; Stark; Ligneau; Elz; Reidemeister; Ganellin; Schwartz; Schunack [Bioorganic and Medicinal Chemistry, 2000, vol. 8, # 5, p. 1139 - 1149]

12
[ 201230-82-2 ]
[ 625-95-6 ]
[ 98-80-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium phosphate; nickel dichloride; Trimethylacetic acid; at 80℃; under 760.051 Torr; for 11h;Green chemistry;	General procedure: Into a 25 ml reaction flask was successively added nickel chloride (0.01 mmol), substituted or non-substituted aryliodide (table 1) (0.5 mmol), phenylboronic acid (0.75 mmol), potassium phosphate (1.0 mmol), pivalic acid (0.25 mmol) and polyethylene glycol 400 (2.0 g), and introduce one atmospheric pressure carbon monoxide. The reaction mixture at 80 C react until starting material reaction complete and cool to room temperature, pressure reducing evaporate the solvent column chromatography separation to obtain the product. The experimental results are set out in table 1.
88%	With palladium diacetate; sodium carbonate; In water; at 100℃; under 760.051 Torr; for 7h;Sealed tube; Autoclave; Green chemistry;	General procedure: A 75 mL autoclave equipped with a Teflon liner and a magnetic stirrer bar was charged with Pd(OAc)2 (4.48 mg, 2.0 × 10-2 mmol), L (46.7 mg, 4.0 × 10-2 mmol) and H2O (6 mL) and the mixture was stirred at room temperatures for 0.5 h under N2. Then iodobenzene (113 muL, 1 mmol), phenylboronic acid (134 mg, 1.1 mmol), Na2CO3(106 mg, 1 mmol), and n-decane (0.1 mL, GC internal standard) were added. Once sealed, the autoclave was purged three times with CO, and pressurized to 1 atm of CO. The reaction mixture was stirred at 100 C for 2 h. After reaction, the mixture was extracted with diethyl ether (3 × 5 mL). The combined organic layer was concentrated in vacuo and the product was purified by column chromatography. In the recycling experiment, the aqueous phase containing the catalyst was subjected to a second run by charging it with the same substrates as mentioned above, and the reaction performed under the same conditions.

Reference： [1]Patent: CN103951538,2017,B .Location in patent: Paragraph 0003; 0017; 0020-0026
[2]Catalysis Communications,2015,vol. 71,p. 106 - 110
[3]Journal of Organic Chemistry,2014,vol. 79,p. 1454 - 1460
[4]Chemical Communications,2014,vol. 50,p. 3874 - 3877
[5]European Journal of Organic Chemistry,2009,p. 1585 - 1591
[6]RSC Advances,2014,vol. 4,p. 44312 - 44316
[7]ChemSusChem,2018,vol. 11,p. 3382 - 3387
[8]Applied Organometallic Chemistry,2019,vol. 33

13
[ 21436-44-2 ]
[ 98-80-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With NHC-Pd(II)-Im; sodium hydrogencarbonate; In water; at 50℃; for 12h;Inert atmosphere;	General procedure: Under N2 atmosphere, NaHCO3 (2.4 mmol), benzoic anhydride 3a (1.5 mmol), phenylboronic acid 2a (0.75 mmol), and H2O were successively added into a Schlenk reaction tube. The mixture was stirred at room temperature for about 10 min. Then NHC-Pd(II)-Im complex 1 (1.0 mol %) was added. The mixture was stirred at room temperature for 12 h and then was diluted with CH2Cl2, washed with saturated brine, dried over anhydrous Na2SO4. The dried organic phase was then filtered, concentrated under reduced pressure and purified by flash column chromatography on silica gel to give the pure product 4a.

Reference： [1]Tetrahedron,2012,vol. 68,p. 5806 - 5809

14
[ 620-47-3 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tert.-butylnitrite; oxygen; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In 1,1,2,2-tetrachloroethane; at 130℃; for 8h;Autoclave;	General procedure: A Teflon-lines 316 L stainless steel autoclave (300 mL) equipped with magnetic stirring bar was charged with substituted diarylmethanes 1 (2 mmol), 136.2 mg DDQ (0.6 mmol, 30 mol %), 41.2 mg TBN (0.4 mmol, 20 mol %), 480 mg acetic acid (8 mmol) and 20 mL TeCA. The autoclave was closed and charged with oxygen to 0.3 MPa. Then the autoclave was placed in an oil bath, which was preheated to 130 C. The mixture was then stirred for a certain time until the reaction was completed. The autoclave was taken out from the oil bath, cooled to room temperature and carefully depressurized. The mixture was concentrated under reduced pressure and purified by column chromatography to give the desired diarylketones.

Reference： [1]Tetrahedron,2015,vol. 71,p. 6733 - 6739
[2]Chemistry - A European Journal,2013,vol. 19,p. 5542 - 5545

15
[ 17933-03-8 ]
[ 100-52-7 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium phosphate; 3,3-dimethyl-butan-2-one; C14H10Cl2N2O2Ru; tri tert-butylphosphoniumtetrafluoroborate; In water; toluene; at 100℃; for 24h;	General procedure: In a typical run, an oven-dried 10 mL round bottom flask was charged with a known mole percent of ruthenium catalyst, K3PO4 (1.0 mmol), p-substituted phenylboronic acid (1.25 mmol), ligand (0.05 mmol), arylaldehyde (0.5 mmol) and 2.0 mL toluene and 0.2 mL water as solvent. The flask was placed in a preheated oil bath at required temperature. After the specified time the flask was removed from the oil bath and water (20 mL) added, followed by extraction with ether (4 × 10 mL). The combined organic layers were washed with water (3 × 10 mL), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in hexane and analyzed by GCMS.
88%	With [Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh3)]; caesium carbonate; In toluene; at 110℃; for 12h;	General procedure: Arylboronic acid (1 mmol), aromatic aldehyde (1.5 mmol), Cs2CO3 (3.0 mmol), catalyst (5.0 mol%) and toluene (3.0 ml) were taken in a round-bottom flask. The mixture was then heated under reflux for 12 h under aerobic conditions and monitored by TLC. At the end of the specified time, the reaction mixture was cooled to room temperature, quenched with 1 N HCl (5 ml) and finally extracted with ethyl acetate (2 × 5 ml). The combined extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The residue obtained was subjected to flash chromatography on a silica gel column to purify the desired ketone.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 750,p. 176 - 184
[2]Tetrahedron Letters,2017,vol. 58,p. 405 - 409

16
[ 123026-51-7 ]
[ 5908-41-8 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
55%	With chloro(1,5-cyclooctadiene)rhodium(I) dimer; In para-xylene; at 130℃; for 42h;Schlenk technique; Inert atmosphere;	General procedure: A Schlenk tube was charged with NaBPh4 (2a, 51.5 mg, 0.150 mmol) and [Rh(OH)(cod)]2 (1.4 mg, 3.1 mumol, 6 mol% Rh). The tube was evacuated and backfilled with nitrogen, and then benzoyltrimethylsilane (1a, 17.9 mg, 0.100 mmol) and toluene (1.0 mL) were added via syringe through the septum. The mixture was heated at 90 C for 8 h. The reaction mixture was filtered through a plug of Florisil washing with hexane-AcOEt (5:1), and the filtrate was concentrated. Purification by preparative TLC on silica gel (hexane:AcOEt = 8:1) afforded the title compound (3aa, 17.6 mg, 0.069 mmol, 68%) as a pale yellow oil.

Reference： [1]Journal of Organometallic Chemistry,2014,vol. 765,p. 64 - 67

17
[ 14635-91-7 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
61%	With oxygen; copper diacetate; potassium carbonate; aniline; In dimethyl sulfoxide; at 120℃;Schlenk technique; Sealed tube;	General procedure: An oven-dried Schlenk tube was charged with a magnetic stir-bar, 1,2-diarylalkynes 1 (0.5mmol), aniline (0.6mmol), K2CO3 (0.5mmol), Cu(OAc)2 (0.075mmol), DMSO (3mL), The tube was sealed, and oxygen was purged through syringe. Reaction was stirred at 120C for 16-18h. After the reaction was finished, the reaction mixture was diluted in 30mL ethyl acetate, filtered on Celite pad. The organic portion was washed with a saturated solution of brine (8mL), saturated NH4Cl (8mL), a saturated solution of brine (8mL), dried (Na2SO4) and concentrated in vacuum, and the resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate) to afford the desired products 2.

Reference： [1]RSC Advances,2015,vol. 5,p. 690 - 693
[2]Tetrahedron,2015,vol. 71,p. 1045 - 1049

18
[ 557-93-7 ]
[ 643-65-2 ]
2-methyl-1-phenyl-1-(m-tolyl)prop-2-en-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: 2-bromoprop-1-ene With iodine; magnesium In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: 3-methyl benzophenone In tetrahydrofuran at 0 - 20℃; Inert atmosphere;

Reference： [1]Bunescu, Ala; WangDr, Qian; Zhu, Jieping [Angewandte Chemie - International Edition, 2015, vol. 54, # 10, p. 3132 - 3135][Angew. Chem., 2015, vol. 127, # 10, p. 3175 - 3178,4][Angewandte Chemie, 2015, vol. 127, # 10, p. 3175 - 3178,4]

19
[ 100-52-7 ]
[ 253342-48-2 ]
[ 643-65-2 ]

Reference： [1]Chemistry - A European Journal,2015,vol. 21,p. 8741 - 8744

20
[ 21436-44-2 ]
potassium phenyltrifluoborate [ No CAS ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
45%	With copper(l) iodide; tris(triphenylphosphine)rhodium(l) chloride; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; at 120℃; for 2h;	General procedure: A reaction vessel was charged with a mixture of a benzoic anhydride (or an aryl carboxylic anhydride) (0.30 mmol), potassium aryltrifluoroborate (or potassium phenyltrifluoroborate) (0.60 mmol), K2CO3 (0.60 mmol), CuI (0.30 mmol), RhCl(PPh3)3 (0.003 mmol, 1.0 mol %) and xylene (1.5 mL). The mixture was heated to 120 C and stirred for 2 h. After the completion of the reaction, the mixture was quenched with 5 mL of water, and then extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over magnesium sulfate. After removal of the solvent in vacuo, the product was isolated by column chromatography. Ethyl acetate/petroleum ether was used for elution and the yield was calculated based on the amount of aryl benzoic anhydride (the purified products were identified by NMR spectra).

Reference： [1]Tetrahedron,2015,vol. 71,p. 4635 - 4639

21
potassium trifluoro(3-methylphenyl)borate [ No CAS ]
[ 93-97-0 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(l) iodide; tris(triphenylphosphine)rhodium(l) chloride; potassium carbonate; In 5,5-dimethyl-1,3-cyclohexadiene; at 120℃; for 2h;	General procedure: A reaction vessel was charged with a mixture of a benzoic anhydride (or an aryl carboxylic anhydride) (0.30 mmol), potassium aryltrifluoroborate (or potassium phenyltrifluoroborate) (0.60 mmol), K2CO3 (0.60 mmol), CuI (0.30 mmol), RhCl(PPh3)3 (0.003 mmol, 1.0 mol %) and xylene (1.5 mL). The mixture was heated to 120 C and stirred for 2 h. After the completion of the reaction, the mixture was quenched with 5 mL of water, and then extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over magnesium sulfate. After removal of the solvent in vacuo, the product was isolated by column chromatography. Ethyl acetate/petroleum ether was used for elution and the yield was calculated based on the amount of aryl benzoic anhydride (the purified products were identified by NMR spectra).

Reference： [1]Tetrahedron,2015,vol. 71,p. 4635 - 4639

22
[ 22071-15-4 ]
[ 87-41-2 ]
[ 85-44-9 ]
[ 119-61-9 ]
[ 13020-57-0 ]
[ 63444-57-5 ]
[ 643-65-2 ]
[ 57872-48-7 ]
[ 66067-43-4 ]
[ 32388-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	With dihydrogen peroxide; iron(II); In water; at 20℃;pH 2.0;	General procedure: For the Fenton degradation experiment, 10 mL of a Milli Q water sample acidified at pH 2 with 100 muL H2SO4 0.5 mol/L containing 200 ng of each studied anti-inflammatory drug (diclofenac sodium, ibuprofen and ketoprofen) was placed into a 50 mL brown glass bottle. Immediately, 500 muL of Fe2+solution (1 mg/mL Fe2+) and 200 muL of H2O2 (30%) were added into the brown bottle which was kept under magnetic stirring and room temperature for different time intervals in order to perform the degradation process. Because the catalyst (Fe2+) and the oxidant (H2O2) are consumed very fast, these were refreshed at each 30 minutes in the same amounts as it was described previously. To study the Fenton oxidative process efficiency over the selected drugs, different experiments at 30, 60 and 120 minutes were performed. After each Fenton oxidative experiment, the degradation by-products of NAIDs were extracted with organic solvent and analyzed by GC×GC-qMS.

Reference： [1]Revue Roumaine de Chimie,2014,vol. 59,p. 1021 - 1027

23
[ 625-95-6 ]
[ 639-58-7 ]
[ 199620-14-9 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; nickel dibromide; In N,N-dimethyl-formamide; at 100℃; for 2h;	General procedure: 4-Iodotoluene (1.0 mmol, 0.21 g) was added to a flask equipped with Ph3SnCl (0.4 mmol, 0.15 g), NiBr2 (16.0 mol%, 0.034 g), K2CO3 (3.0 mmol, 0.29 g), and Cr(CO)6 (1.0 mmol, 0.22 g) in DMF (3.0 mL) and the resulting mixture was heated in an oil bath at 100 C and stirred for 2.7 h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to room temperature, then H2O (10 mL) was added and the mixture was transferred to a separatory funnel. The aqueous phase was further washed with EtOAc (3×10 mL) and the combined organic phases were dried over anhydrous Na2SO4 and then filtered. Column chromatography of the obtained residue on silica gel (n-hexane/EtOAc=20:1) gave the desired ketone in 89% yield (0.11 g) (Table4, entry 2).

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 794,p. 282 - 287

24
[ 1037-92-9 ]
[ 625-95-6 ]
[ 199620-14-9 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
70%	With potassium carbonate; nickel dibromide; In N,N-dimethyl-formamide; at 100℃; for 2.3h;	General procedure: 4-Iodotoluene (1.0 mmol, 0.21 g) was added to a flask equipped with Ph3SnCl (0.4 mmol, 0.15 g), NiBr2 (16.0 mol%, 0.034 g), K2CO3 (3.0 mmol, 0.29 g), and Cr(CO)6 (1.0 mmol, 0.22 g) in DMF (3.0 mL) and the resulting mixture was heated in an oil bath at 100 C and stirred for 2.7h. Progress of the reaction was monitored by TLC. After completion, the reaction mixture was cooled to room temperature, then H2O (10 mL) was added and the mixture was transferred to a separatory funnel. The aqueous phase was further washed with EtOAc (3×10 mL) and the combined organic phases were dried over anhydrous Na2SO4 and then filtered. Column chromatography of the obtained residue on silica gel (n-hexane/EtOAc=20:1) gave the desired ketone in 89% yield (0.11 g) (Table4, entry 2).

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 794,p. 282 - 287

25
[ 201230-82-2 ]
[ 625-95-6 ]
[ 603-33-8 ]
[ 643-93-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
66%	With potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 3h; Green chemistry;

Reference： [1]Hao, Wenyan; Liu, Haiyi; Yin, Lin; Cai, Mingzhong [Journal of Organic Chemistry, 2016, vol. 81, # 10, p. 4244 - 4251]

26
[ 99-94-5 ]
[ 611-73-4 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
55%		Was added 0.0136g (0.1mmol) p-toluic acid, 0.0450g (0.3mmol) of benzoyl formic acid in 10mL pressure reaction tube, 0.0033g (0.01mmol) palladium trifluoroacetate, 0.0689g (0.25mmol) silver carbonate , 0.0164g (0.2mmol) of anhydrous sodium acetate, ImL ethylene glycol dimethyl ether, the reaction mixture was stirred under a sealed condition 150 deg.] C 28 hours, cooled to room temperature after completion of the reaction, was added 0.0159g (0.2mmol) CuO, 0.2mL N, N- dimethylformamide, stirred under confined conditions 150 28 hours the reaction, by column chromatography on silica gel catalyst was removed by filtration and the salts, by thin layer chromatography to give 3-methyl benzophenone, which The yield was 55%, and structural characterization data are as follows:

Reference： [1]Patent: CN105418393,2016,A .Location in patent: Paragraph 0013; 0014; 0015; 0016; 0017

27
[ 643-65-2 ]
[ 350-57-2 ]
1-(3-methylphenyl)-1-phenyl-2,2,3,3-tetrafluoro-3-phenoxypropan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hexamethylsilazane; In toluene; at 20℃; for 0.25h;Inert atmosphere;	General procedure: A three necked RB flask (25 mL) with a dropping funnel, an air condenser and inlet and outlet tubes for dry N2 gas was cooled to -10 C with ice salt mixture. One of the benzophenones (2 mmol) was dissolved in 2 mL of DMF and transferred under nitrogen atmosphere. 1a, 1b or 2 (4 mmol) was dissolved in 1 mL of DMF and added. A very slow stream of nitrogen was maintained in the case of reactions with 1b. KHMDS (0.798 g, 4 mmol) dissolved in 2 mL of DMF was added drop wise over a 5 min period while the contents were kept stirred. Different colour change occurred in all cases (violet in case of benzophenone) in the beginning but got discharged slowly. After about 15 min, water (3 mL), dil. H2SO4 (1 mL) and ether (10 mL) were added in that sequence. The contents were stirred at -10 C for 5 min, brought to RT, the layers separated, water layer extracted with 2 x 10 mL of ether, all the organic layers combined, washed with dil. Sodium bicarbonate till it was faintly acidic to pH paper and dried over anhydrous sodium sulfate. Upon evaporation of the solvent the crude mixture was chromatographed on silica gel using hexane-benzene. Isolated percentage yield of individual product isgiven in Table 1. 4.2. Reaction of benzophenones with 1a, 1b or 2 and KHMDS in THF or toluene The above procedure was followed except that THF or toluene replaced (in volume quantity) DMF. The reaction was done at RT using a water bath as heat sink. Reaction was quenched with dil. H2SO4 10 min after the base was added. Extraction procedure similar to the one adopted in Section 4.1 was followed. The crude product contained only excess of 1a or 1b which was removed by evacuation at 1 mm Hg for 30 min keeping the temperature of flask at 90 C (water bath). The products obtained were practically pure (>99% by GC).

Reference： [1]Journal of Fluorine Chemistry,2015,vol. 169,p. 38 - 49

28
[ 643-65-2 ]
[ 96-22-0 ]
2-ethyl-1-(3-methylphenyl)-1-phenyl-1,2-butanediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With lanthanum; iodine; In tetrahydrofuran; at 25℃; for 3h;Inert atmosphere;	General procedure: Lanthanum powder (1.5mmol, 208mg) was placed in a two-necked flask. The diaryl ketone (1.0mmol), iodine (0.3mmol, 76mg), electrophile (1.0 or 2.0 mmol), and THF (5mL) were added to the flask, and the mixture was stirred at 25C or 67C for 3h under nitrogen atmosphere. After the reaction, aqHCl (1M) was added to the reaction mixture, and the resulting solution was extracted with diisopropyl ether (five times). The organic layer was dried over MgSO4. The resulting mixture was filtered, and the organic solvent was removed under reduced pressure. Purification of the residue by column chromatography on silica gel afforded the corresponding coupling products. Products (2-ethyl-1,1-diphenyl-1,2-butanediol (3a),19 1-(diphenylhydroxymethyl)cyclohexanol (3j),4b,19 1,1,2-triphenyl-1,2-propanediol (3k),19 2-methyl-1,1-diphenyl-1,2-butanediol (3m),19 2-hydroxy-1,2,2-triphenylethanone (5a),4b 1-hydroxy-1,1,3-triphenylpropan-2-one (5b),4b 1-hydroxy-1,1-diphenyloctan-2-one (5c),4b,20 1-hydroxy-1,1-diphenyl-2-(4-methylphenyl)ethanone (5d),21 2-hydroxy-2,2-diphenyl-1-(2-naphthyl)-1-ethanone (5e),22 and 1-hydroxy-1,1-diphenyl-2-propanone (5f)23) were characterized by comparison of their spectra data (1H and 13C NMR and IR) to those of authentic samples.

Reference： [1]Tetrahedron,2015,vol. 71,p. 1287 - 1291

29
[ 368-47-8 ]
[ 1711-06-4 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
64%	With tri-tert-butyl phosphine; palladium diacetate; cesium fluoride; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: To a screw-capped vial in a glovebox, Pd(OAc)2 (0.020 mmol, 4.5 mg), PtBu3 (0.0800 mmol, 16.2 mg), CsF (1.400 mmol, 212.7 mg), and xylene (0.4 mL) were added in that order. The vial was then sealed and removed from the glovebox, an acyl chloride (0.4 mmol) and an aryltrifluorosilane (1.2 mmol) were successively added to the vial. The mixture was heated at 140 C for 24 h. After the reaction, the resultant mixture was filtered through a pad of silica gel (2 g, eluent; EtOAc). After removal of the volatile materials by rotary evaporation, the filtrate was analyzed by GC (n-decane as a internal standard) or NMR (1,1,2,2-tetrachloroethane as a internal standard). The crude material was purified by silica gel column chromatography (eluent; hexane:EtOAc = 99:1).

Reference： [1]Chemistry Letters,2016,vol. 45,p. 790 - 792

30
[ 13688-77-2 ]
[ 98-88-4 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
51%	With tri-tert-butyl phosphine; palladium diacetate; cesium fluoride; In 5,5-dimethyl-1,3-cyclohexadiene; at 140℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: To a screw-capped vial in a glovebox, Pd(OAc)2 (0.020 mmol, 4.5 mg), PtBu3 (0.0800 mmol, 16.2 mg), CsF (1.400 mmol, 212.7 mg), and xylene (0.4 mL) were added in that order. The vial was then sealed and removed from the glovebox, an acyl chloride (0.4 mmol) and an aryltrifluorosilane (1.2 mmol) were successively added to the vial. The mixture was heated at 140 C for 24 h. After the reaction, the resultant mixture was filtered through a pad of silica gel (2 g, eluent; EtOAc). After removal of the volatile materials by rotary evaporation, the filtrate was analyzed by GC (n-decane as a internal standard) or NMR (1,1,2,2-tetrachloroethane as a internal standard). The crude material was purified by silica gel column chromatography (eluent; hexane:EtOAc = 99:1).

Reference： [1]Chemistry Letters,2016,vol. 45,p. 790 - 792

31
[ 37952-93-5 ]
[ 17933-03-8 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
82%	With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II); at 70 - 80℃; for 5.5h;Inert atmosphere; Ionic liquid;	General procedure: An oven dried RB flask equipped with magnetic stirrer bar was charged with the IL solvent (BMIM)BF4 or (BMIM)PF6 (5-7 mL), and NBSac (1 mmol), and the mixture was stirred at r.t. under nitrogen atmosphere for 15-20 minutes. The reaction mixture was then charged with the boronic acid (2 mmol) and Pd(OAc)2 or NiCl2(dppp) (5 mol%) and basic-IL [PAIM][NTf2] (2 mmol). The reaction mixture was heated gently under stirring at 70-80 C, while monitoring the progress of the reaction TLC. Upon completion, the reaction mixture was cooled to r.t. and the products were extracted 4 times with hexane/ethyl acetate (80:20). The solvent was removed under vacuum and the crude product was chromatographed with hexane/ethyl acetate (70:30) mixture to afford pure compounds.

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 3876 - 3880
[2]Tetrahedron Letters,2020,vol. 61

32
[ 620-23-5 ]
[ 98-80-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With [Pd(2-((1-naphthalenyl)methylene)-N-phenylhydrazinecarbothioamide)Cl(PPh3)]; caesium carbonate; In toluene; at 110℃; for 12h;	General procedure: Arylboronic acid (1 mmol), aromatic aldehyde (1.5 mmol), Cs2CO3 (3.0 mmol), catalyst (5.0 mol%) and toluene (3.0 ml) were taken in a round-bottom flask. The mixture was then heated under reflux for 12 h under aerobic conditions and monitored by TLC. At the end of the specified time, the reaction mixture was cooled to room temperature, quenched with 1 N HCl (5 ml) and finally extracted with ethyl acetate (2 × 5 ml). The combined extracts were dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The residue obtained was subjected to flash chromatography on a silica gel column to purify the desired ketone.

Reference： [1]Applied Organometallic Chemistry,2017,vol. 31
[2]Tetrahedron Letters,2017,vol. 58,p. 405 - 409

33
[ 884-09-3 ]
[ 17933-03-8 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
72%	With copper(l) iodide; silver carbonate; In N,N-dimethyl-formamide; at 120℃; for 15h;	General procedure: Thiolester (0.25 mmol), arylboronic acids (0.375 mmol), CuI (20 mol%, 10 mg), Ag2CO3 (5 mol%, 4 mg) and DMF (3 ml) were taken in a 25 ml round bottomed flask. The reaction mixture was heated at 120 C for 8-24 h. The reaction monitored using TLC. Upon completion, the reaction mixture was diluted with water and extracted with DCM (3x10 ml). The combined organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. The resulting ketone was purified was purified using silica gel column chromatography (EtOAc and petroleum ether 60-80 C).

Reference： [1]Tetrahedron Letters,2017,vol. 58,p. 2751 - 2756

34
[ 1438894-51-9 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In water; chlorobenzene; at 130℃; for 2h;	In a reactor having a magneton, phenyl m-tolylmethanol acetate (formula (1-3), 0.48 g, 2 mmol) was added,DDQ (0.45 g, 2 mmol), H2O (0.29 g, 16 mmol) and chlorobenzene (8 ml)The reaction was stirred at 130 C,TLC monitoring,Reaction 2h,The reaction solution was analyzed by gas chromatography (GC), the conversion was 100%The product selectivity was 99%.The reaction solution was evaporated under reduced pressure,Over silica gel column,A mixture of ethyl acetate and petroleum ether in a volume ratio of 1: 200 was used as the eluent,The eluate containing the target compound was collected,The solvent was distilled off and dried to obtain 0.38 g of phenyl m-tolylmethanone,The separation yield of phenyl m-tolylmethanone was 97%.

Reference： [1]Patent: CN105037115,2017,B .Location in patent: Paragraph 0035; 0036
[2]Patent: CN104987273,2016,B .Location in patent: Paragraph 0033-0036

35
[ 108-86-1 ]
[ 201230-82-2 ]
[ 17933-03-8 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 120℃; under 760.051 Torr;Sealed tube;	General procedure: General procedure: a 50 mL ask equipped with a magnetic stir bar was charged with aryboronic acid (1 mmol, 1 equiv), aromatic halides (1.2 mmol, 1.2 equiv), catalyst (2 mol%), base (2 mmol, 2 equiv), DMF (5 mL) solution under CO (1 atm) atmosphere, along with sealed the reaction flask by a rubber stopper and CO was injected into it with a stainless steel gas flowmeter. The mixture was then stirred at 120 C forthe indicated time (SI, Fig. S1). After being allowed to cool to roomtemperature, the reaction mixture was diluted with 5 mL water and extracted with diethyl ether (3 × 5 mL). The organic phases werecombined, and the volatile components were evaporated in a rotaryevaporator. The residue was puried by column chromatography onsilica gel.

Reference： [1]Catalysis Communications,2017,vol. 101,p. 10 - 14

36
di(m-tolyl)borinic acid [ No CAS ]
[ 10533-83-2 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; potassium carbonate; In tetrahydrofuran; at 65℃; for 12h;Inert atmosphere; Schlenk technique;	General procedure: Under a N2 atmosphere, to a 10 mL dry flask were added amide (0.5 mmol), diarylborinic acid (1.0 mmol), (IPr)PdCl2(3-chloropydine) (1 mol%), K2CO3 (1.5mmol), and THF (4 mL). The mixture was stirred at 65C for a given time or monitored by TLC until the starting material was completely consumed. The reaction mixture was diluted with CH2Cl2 (15 mL), followed by washing with H2O (2×10 mL).The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure to give crude product, which was purified by column chromatography on silica gel to afford product.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 2299 - 2301

37
[ 55095-20-0 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: dichloromethane / 0.17 h / 0 - 20 °C 2: 2,4,6-triphenylpyrylium tetrafluoroborate / 8 h / 35 °C / Irradiation

Reference： [1]Wang, Hongyu; Man, Yunquan; Wang, Kaiye; Wan, Xiuyan; Tong, Lili; Li, Na; Tang, Bo [Chemical Communications, 2018, vol. 54, # 78, p. 10989 - 10992]

38
[ 643-65-2 ]
[ 1779-49-3 ]
[ 4333-70-4 ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 6143 - 6150
[2]Organic Letters,2019,vol. 21,p. 6285 - 6288
[3]Polyhedron,2020,vol. 180

39
[ 625-95-6 ]
[ 639-58-7 ]
[ 199620-15-0 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
89%	With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 5.2h;	General procedure for carbonylative Stille couplingof aryl iodides with Mo(CO)6 using MCNTs(at)(A-V)-silica-Pd catalyst General procedure: MCNTs(at)(A-V)-silica-Pd (1.5% mol%) was added to a mixtureof aryl iodide (1 mmol), Mo(CO)6 (1 mmol), Cs2CO3(1.5 mmol), Ph3SnCl(0.4 mmol) in DMF (3 mL) in a flask,and the reaction was stirred at 100 °C for an appropriatetime under atmospheric pressure. Then, the reaction wascooled down to room temperature followed by separation ofthe catalyst by an external magnet. The mixture was washedwith 10 mL water, and the crude product was isolated usingEtOAc (3 × 10 mL). The organic phases were combined anddried over Na2SO4,evaporated, and purified by column chromatographyon silica gel (n-hexane/EtOAc) to deliver thedesired ketone in high yields.

Reference： [1]Etemadi-Davan, Elham; Khalili, Dariush; Banazadeh, Ali Reza; Sadri, Ghazal; Arshad, Pourya [Journal of the Iranian Chemical Society, 2021, vol. 18, # 8, p. 1891 - 1903]

40
[ 591-50-4 ]
[ 124-38-9 ]
[ 17933-03-8 ]
[ 643-93-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 74.8% 2: 12.4%	With potassium carbonate; triethylamine In water; N,N-dimethyl-formamide for 6h; Irradiation;

Reference： [1]Fu, Shanshan; Guo, Guang-Chen; Guo, Song; Lu, Tong-Bu; Yao, Shuang; Yuan, Wenjuan; Zhang, Zhi-Ming [Journal of the American Chemical Society, 2021, vol. 143, # 49, p. 20792 - 20801]

41
[ 124-38-9 ]
[ 625-95-6 ]
[ 98-80-6 ]
[ 643-93-6 ]
[ 643-65-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 82.8% 2: 7.2%	With potassium carbonate; triethylamine In water; N,N-dimethyl-formamide for 6h; Irradiation;

Same Skeleton Products

Related Products

Historical Records

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

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

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. 643-65-2 ] {[proInfo.proName]}

Quality Control of [ 643-65-2 ]

Related Doc. of [ 643-65-2 ]

Product Details of [ 643-65-2 ]

Calculated chemistry of [ 643-65-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 643-65-2 ]

Application In Synthesis of [ 643-65-2 ]

[ 643-65-2 ] Synthesis Path-Upstream 1~1

[ 643-65-2 ] Synthesis Path-Downstream 1~41

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry