[ CAS No. 1073-67-2 ] {[proInfo.proName]}

Name: 1073-67-2|1-Chloro-4-vinylbenzene|98% (stabilized with TBC)
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SKU: A270085
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3d Animation Molecule Structure of 1073-67-2

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Quality Control of [ 1073-67-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1073-67-2 ]

SDS Specification

Alternatived Products of [ 1073-67-2 ]

Product Details of [ 1073-67-2 ]

CAS No. :	1073-67-2	MDL No. :	MFCD00000632
Formula :	C₈H₇Cl	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KTZVZZJJVJQZHV-UHFFFAOYSA-N
M.W :	138.59	Pubchem ID :	14085
Synonyms :

Calculated chemistry of [ 1073-67-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.54
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.49 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.27
Log Po/w (XLOGP3) :	3.74
Log Po/w (WLOGP) :	2.87
Log Po/w (MLOGP) :	3.44
Log Po/w (SILICOS-IT) :	3.27
Consensus Log Po/w :	3.12

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.48
Solubility :	0.0456 mg/ml ; 0.000329 mol/l
Class :	Soluble
Log S (Ali) :	-3.43
Solubility :	0.0512 mg/ml ; 0.00037 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.43
Solubility :	0.0515 mg/ml ; 0.000372 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.31

Safety of [ 1073-67-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P501-P261-P270-P210-P271-P264-P280-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330-P302+P352+P312-P304+P340+P312-P403+P235	UN#:	N/A
Hazard Statements:	H302+H312+H332-H315-H319-H227	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1073-67-2 ]

* 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 [ 1073-67-2 ]
Downstream synthetic route of [ 1073-67-2 ]

[ 1073-67-2 ] Synthesis Path-Upstream 1~20

1
[ 1073-67-2 ]
[ 2587-00-0 ]
[ 2402-78-0 ]
[ 2788-86-5 ]
[ 2788-86-5 ]

Reference： [1] Organic Letters, 1999, vol. 1, # 13, p. 2077 - 2080

2
[ 54664-52-7 ]
[ 1073-67-2 ]
[ 17422-33-2 ]
[ 52537-00-5 ]
[ 54664-55-0 ]

Reference： [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533

3
[ 93626-92-7 ]
[ 1073-67-2 ]
[ 612-61-3 ]
[ 28446-72-2 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1984, # 7, p. 1569 - 1572

4
[ 1073-67-2 ]
[ 17356-08-0 ]
[ 2103-99-3 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In water at 60℃; for 1 h; Stage #2: for 1 h; Reflux	In a 25 mL reaction flask, add 3 mL of water and 30 μL of Tween,0.5 mmol of chlorostyrene and 0.75 mmol of DBH reacted at 60 °C for 1 h.After the reaction was completed, the water was swirled, 3 mL of ethanol was added, and 0.75 mmol of thiourea was added. The reaction was refluxed for 1 h. After the reaction was completed, ethanol was spin-dried.Ethyl acetate was added to dissolve, and saturated saline solution was added for extraction.The organic phase was concentrated and column chromatography gave 94 mg of a white solid with a yield of 89percent.

Reference： [1] Patent: CN107501204, 2017, A, . Location in patent: Paragraph 0042; 0043; 0044; 0045

5
[ 1073-67-2 ]
[ 2103-99-3 ]

Reference： [1] Patent: CN104262218, 2016, B,
[2] Tetrahedron, 2018, vol. 74, # 27, p. 3602 - 3607

6
[ 1073-67-2 ]
[ 104-86-9 ]

Reference： [1] ChemSusChem, 2018, vol. 11, # 13, p. 2221 - 2228

7
[ 1073-67-2 ]
[ 201230-82-2 ]
[ 6282-88-8 ]
[ 59667-21-9 ]

Reference： [1] Journal of the Chemical Society, Chemical Communications, 1991, # 4, p. 233 - 234

8
[ 1073-67-2 ]
[ 50-00-0 ]
[ 6282-88-8 ]
[ 59667-21-9 ]

Reference： [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 16, p. 4632 - 4636

9
[ 54664-52-7 ]
[ 1073-67-2 ]
[ 17422-33-2 ]
[ 52537-00-5 ]
[ 54664-55-0 ]

Reference： [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533

10
[ 54664-52-7 ]
[ 1073-67-2 ]
[ 17422-33-2 ]
[ 52537-00-5 ]
[ 54664-55-0 ]

Reference： [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533

11
[ 54664-52-7 ]
[ 1073-67-2 ]
[ 54664-55-0 ]
[ 76653-03-7 ]

Reference： [1] Journal of the American Chemical Society, 1981, vol. 103, # 6, p. 1525 - 1533

12
[ 1073-67-2 ]
[ 6529-53-9 ]

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5622 - 5626

13
[ 1073-67-2 ]
[ 6529-53-9 ]
[ 14804-61-6 ]

Reference： [1] Organic and Biomolecular Chemistry, 2016, vol. 14, # 24, p. 5622 - 5626

14
[ 1073-67-2 ]
[ 1130060-55-7 ]
[ 853775-01-6 ]
[ 33892-75-0 ]

Reference： [1] Chemistry Letters, 2009, vol. 38, # 1, p. 40 - 41

15
[ 1073-67-2 ]
[ 80351-58-2 ]
[ 1535-65-5 ]
[ 1421521-00-7 ]

Reference： [1] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952,10
[2] European Journal of Organic Chemistry, 2012, # 30, p. 5943 - 5952

16
[ 1073-67-2 ]
[ 7099-88-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium permanganate; sodium hydroxide In water at 70℃; for 0.5 h;	General procedure: The aryl styrene 0.2mol, 0.4mol sodium hydroxide, water 80mL added to 500mL round bottom flask, heated to 70 ° C, potassium permanganate 0.5mol within 0.5h added in batches after 10min and then reused Ethanol 50mL will notThe reaction of potassium permanganate destruction, the reaction solution was suction filtered, the filtrate was retained, most of the water was distilled off under reduced pressure, the concentrated filtrate was acidified with concentrated hydrochloric acid, and then extracted with dichloromethane to remove the solvent, cooled to give a light The yellow solid was recrystallized from ethanol to give 2-aryl-2-oxoacetic acid.According to General Method 1, 2-(4-chlorophenyl)-2-oxoacetic acid was obtained as a white powder with a yield of 60.0percent.

Reference： [1] Archives of Pharmacal Research, 2010, vol. 33, # 10, p. 1641 - 1649
[2] Patent: CN105949220, 2016, A, . Location in patent: Paragraph 0115; 0116

17
[ 1073-67-2 ]
[ 121-43-7 ]
[ 2156-04-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	Stage #1: With magnesium In tetrahydrofuran Stage #2: at -45 - 20℃; for 3 h;	Vinylphenylboronic acid was prepared according to the procedurein literature [14]. A solution of 4-vinylphenylmagnesiumchloride (prepared from 0.414 g of magnesium powder and2.00 g (14.4 mmol) of 4-chlorostyrene) in 20 mL of anhydrousTHF was added dropwise to a solution of trimethyl borate(2.54 g, 24.5 mmol) in 40 mL of anhydrous THF at −45 °C.Upon addition, the mixture was slowly warmed to room temperature over 3 h and then quenched with 50 mL of 3 M HCl withstirring. The organic layer was set aside, and the aqueous layer was extracted with diethyl ether (2 × 20 mL). The combined organic phases were evaporated until dried and 40 mL of water was added. The reaction mixture was heated until it boils anddecanted. The residual solid was treated with an additional 40 mL of water, heated until it boils, and decanted again. Thesupernatants were combined and allowed to cool to room temperature,then stored at 2 °C for 5 h. Themixture was filtered, andthe filtered white solid was washed with water and dried undervacuum overnight to give 4-vinylphenylboronic acid (1.10 g,52percent): 1H NMR (500 MHz, DMSO-d6) δ 8.03 (br s, 2H), 7.76(d, 2H, J = 8.2 Hz), 7.42 (d, 2H, J = 8.2 Hz), 6.72 (dd, 1H,J = 17.6, 11.1 Hz), 5.87 (d, 1H, J = 17.6 Hz), 5.28 (d, 1H,J = 11.1 Hz).

Reference： [1] Structural Chemistry, 2017, vol. 28, # 2, p. 493 - 500

18
[ 1073-67-2 ]
[ 2156-04-9 ]

Reference： [1] Organometallics, 2011, vol. 30, # 8, p. 2432 - 2452

19
[ 1073-67-2 ]
[ 43189-37-3 ]

Reference： [1] Advanced Synthesis and Catalysis, 2017, vol. 359, # 24, p. 4305 - 4316

20
[ 1073-67-2 ]
[ 191109-51-0 ]

Reference： [1] Tetrahedron, 1997, vol. 53, # 18, p. 6337 - 6350

[ 1073-67-2 ] Synthesis Path-Downstream 1~88

1
[ 1073-67-2 ]
[ 622-98-0 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen; In ethanol; at 20℃; under 760.051 Torr; for 2h;	General procedure: In a typical reaction, 0.015 g of catalyst and 2 mmol of the reactant were taken in 10 mL of ethanol under hydrogen atmosphere. The reaction was monitored by thin-layer chromatography (TLC). After complete disappearance of the starting material, the catalyst was separated by simple filtration and the solvent was removed under reduced pressure to obtain the pure product.
99%Spectr.	With dimethylamine borane; ReBr2(NO)(CH3CN)(PTA)2; In ethanol; at 70℃; for 40h;Inert atmosphere;	General procedure: A solution of the proper olefin substrates (0.5 mmol), dimethylamine-borane (0.25 mmol) and 1 mol% of the rhenium complex (with 10-15 mol% of tBuOK according to Table 3) in the given solvent (0.8e1.0 ml) was stirred for given time at 70 C under nitrogen atmosphere. Upon completion, the reaction mixture was filtered over Celite. The resulting solution was analyzed by 1H NMR spectroscopy. The obtained 1H NMR data of the alkanes were identical to those of the literature [35,49-55]. The yields are listed in Tables 2 and 3.
99.83%Chromat.	With hydrogen; In neat (no solvent); at 20℃; under 7600.51 Torr; for 0.25h;Autoclave; Green chemistry;Catalytic behavior;	General procedure: The hydrogenation reactions were carried out in a 100 mL stainless steel high-pressure batch-type reactor. 20 mmol of the substrates and a certain amount of catalyst samples (1-3 wt%Rh/NZ-CP) were charged into the reactor and the reactor was sealed with 1.0 MPa N2and H2 to remove the air and then, the reactor was then heated up to the desired temperature. After completion of the reaction, the reactor was cooled down to room temperatureand then depressurized. The catalyst was easily isolated from the reaction mixture using centrifuge technique. The composition of reaction mixture was analyzed by GC using an Agilent gas chro-matograph fitted with a FactorFour HP5-MS capillary column. The turnover frequency (TOF) was calculated as the number of molesof reactant consumed per mol of catalyst exposed on surface per hour.

	With hydrogen; In diethyl ether; at 20℃; under 5171.62 Torr; for 2h;Autoclave;	General procedure: 1 mmol of substrate, a suitable amount of Pd-CHCl:TASi02 microcapsules containing 2 x 103 to 1 x 102 mmol Pd, and 5 g of diethylether were transferred to a 25 ml glass-lined autoclave. The autoclave was purged three times with H2 and then pressurized to 100-500 psi. The reactions were held at RT or 60C whilst stirring for the required period of time, followed by centrifugation at 6000 rpm to separate the microcapsules from the reaction mixture. Afterwards, the capsules were washed two times with diethyl ether, dried in an oven at 50C for 2 hours and then used for the next catalytic cycle. Lastly, the reaction contents were obtained by evaporating the solvent, and examined using 1 H NMR and GC to calculate the conversion of the products.
	With basolite C300; Dimethylphenylsilane; In tetrahydrofuran; at 70℃; for 2h;Catalytic behavior;	General procedure: In a typical reaction, 20 mg of Cu3(BTC)2 was added to the reaction flask containing (0.5 mmol) of 1 followed by 0.5 mL of tetrahydrofuran,ethanol (1 mmol) and DMPS (1 mmol). After completion of sequential addition of these reagents, the reaction flask was closed by silicon rubber septum and this reaction mixture was stirred at 70 C for the required time as indicated in Tables 1 and 2. It was observed visually that the reaction mixture turns from blue to brown and returned back to original blue colour after 2 h with the evolution of hydrogen gas. The reaction progress was monitored by GC and after completion of the reaction, the mixture was washed three times with acetone and filtered.Then, the product was analyzed by GC for its purity and selectivity.Conversion was determined by Agilent 7820 A GC using internal standard method. The identical procedure was followed for the reusability experiments except the use of recovered solid catalyst with fresh reactants.

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[9]European Journal of Organic Chemistry,2011,p. 672 - 675
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[11]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 2097 - 2101
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[13]Journal of Organic Chemistry,1963,vol. 28,p. 2347 - 2350
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2
[ 1073-67-2 ]
[ 64-18-6 ]
[ 2019-34-3 ]
[ 938-95-4 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 4739 - 4741
[2]Organic Letters,2017,vol. 19,p. 1748 - 1751

3
[ 1073-67-2 ]
[ 6608-47-5 ]
[ 98821-26-2 ]

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 5045 - 5050

4
[ 1073-67-2 ]
[ 201230-82-2 ]
[ 622-98-0 ]
[ 286964-62-3 ]

Reference： [1]Journal of Organometallic Chemistry,1983,vol. 249,p. 411 - 414

5
[ 1073-67-2 ]
[ 201230-82-2 ]
[ 6282-88-8 ]
[ 59667-21-9 ]

Reference： [1]Journal of the Chemical Society. Chemical communications,1991,p. 233 - 234

6
[ 1073-67-2 ]
[ 17985-72-7 ]
[ 140675-91-8 ]

Reference： [1]Journal of Organometallic Chemistry,1992,vol. 428,p. 1 - 12

7
[ 1073-67-2 ]
[ 622-98-0 ]
[ 3391-10-4 ]

Reference： [1]Journal of Organic Chemistry,1984,vol. 49,p. 1064 - 1071

8
[ 1073-67-2 ]
[ 4251-65-4 ]
[ 2788-86-5 ]

Reference： [1]Journal of the American Chemical Society,1986,vol. 108,p. 2309 - 2320
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[5]ChemCatChem,2013,vol. 5,p. 1092 - 1095

9
[ 1073-67-2 ]
[ 144-62-7 ]
[ 2019-34-3 ]
[ 938-95-4 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 4739 - 4741

10
[ 99-91-2 ]
[ 1073-67-2 ]
[ 622-98-0 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1695 - 1698

11
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[ 1073-67-2 ]
[ 622-98-0 ]
[ 3391-10-4 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions II,1991,p. 1695 - 1698

12
[ 54664-52-7 ]
[ 1073-67-2 ]
[ 54664-55-0 ]
[ 76653-03-7 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1525 - 1533

13
[ 54664-52-7 ]
[ 1073-67-2 ]
[ 17422-33-2 ]
[ 52537-00-5 ]
[ 54664-55-0 ]

Reference： [1]Journal of the American Chemical Society,1981,vol. 103,p. 1525 - 1533

14
[ 84648-20-4 ]
[ 1073-67-2 ]
[ 622-98-0 ]
[ 84648-32-8 ]
[ 84648-27-1 ]
[ 108-90-7 ]

Reference： [1]Journal of Organic Chemistry,1983,vol. 48,p. 955 - 963

15
[ 93626-92-7 ]
[ 1073-67-2 ]
[ 612-61-3 ]
[ 28446-72-2 ]

Reference： [1]Journal of the Chemical Society. Perkin transactions I,1984,p. 1569 - 1572

16
[ 1073-67-2 ]
[ 68-12-2 ]
[ 1791-26-0 ]

Yield	Reaction Conditions	Operation in experiment
		4-Chlorostyrene (35g) was distilled over sodium hydroxide pellets (1.Og) in vacuo. The initially pale brown 4-chlorostyrene turned very dark blue on stirring with the NaOH pellets (due to deprotonation of the 0.10wt% 4-tert-butyl-catechol inhibitor). The inhibitor free 4-chlorostyrene distilled over at a temperature of 41-43.50C at a pressure of 4.10 torr.Magnesium turnings (99.8% pure, 5.5Og, 0.226 moles) were placed into a dry (heat-gun dried under vacuum) 3 -neck 50OmL RB flask attached to a double-layer coil condenser, a 125mL pressure-equalising funnel with a needle valve, a B19 suba-seal and a vacuum-nitrogen manifold and purge- filled with nitrogen. 27.6g (0.199 moles) of freshly distilled inhibitor free 4- chlorostyrene was weighed into a dry 10OmL graduated Schlenk tube. This flask was purge- filled with nitrogen and 10OmL of anhydrous THF was cannula transferred into the flask forming a colourless solution. The 4-chlorostyrene solution was then cannula transferred into the addition funnel. A solution of 1.5mL of ethylbromide in 4mL of anhydrous THF was then added via syringe to the magnesium turning to initiate the reaction. The flask became warm to the touch and the solution coating the magnesium turning started to reflux. The 4-chlorostyrene solution was then added at such a rate as to maintain a gentle reflux over a period of 45 minutes. The grey reaction mixture was then stirred at room temperature for 20 minutes before being brought to reflux for 15 minutes using a heat gun. The reaction mixture was then allowed to cool slowly to room temperature over a period of 1 hour by which time most of the magnesium had reacted to form/7-vinylphenylmagnesium chloride bar a few small shavings.A solution of 17.06mL (0.220 moles) of anhydrous LambdazetaiV'-dimethylformamide in 10OmL of anhydrous tetrahydrofuran was cannula transferred into the 125mL addition funnel and then added dropwise over a period of 1 hour to the previously prepared solution of p- vinylphenylmagnesium chloride (0.199 moles). The temperature was maintained at 2O0C during the addition (higher temperatures resulted in polymer formation and lower yields). The reaction mixture was stirred for 2 hours and then allowed to remain overnight under a nitrogen atmosphere. The reaction mixture was quenched with 20OmL saturated aqueous ammonium chloride solution causing an initial exotherm (up to 450C) and then the precipitation of a voluminous "gelatinous" white solid (magnesium hydroxides). The resultant emulsion was broken by centrifuging aliquots of the mixture at 4000rpm for 3 minutes and the resultant clarified two phase mixture poured into a 50OmL separating funnel and the organic layer partitioned and collected. The remaining aqueous layer was extracted twice with 10OmL of Et2O; the organic extracts were then combined and dried over anhydrous MgSO4. The drying mixture was filtered and the collected solid washed with 2>;<;50mL portions OfEt2O. The filtrate and washings were combined and the solvent was stripped off in vacuo using a rotary evaporator and the residue was distilled in vacuo in the presence of a heaped spatula measure of phenothiazine with two fractions coming over: Fraction 1 (530C at 0.425 torr; v. pale yellow liquid), Fraction 2 (48-5O0C at 0.350 torr; v. pale yellow liquid). Fraction 1 was discarded and fraction 2 retained and a yield taken. Yield: 18.325g (70%, very pale yellow liquid). 1H NMR (CDCl3) 35.46 (d, IH, =C-H), 5.93 (d, IH, =C-H), 6,79 (dd, IH, =C-H), 7.57 (d, 2H, ArH), 7.86 (d, 2H, ArH), 10.01 (s, IH, -CH=O).

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[5]Patent: WO2010/116142,2010,A2 .Location in patent: Page/Page column 58-60
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17
[ 1073-67-2 ]
[ 622-98-0 ]
[ 100-41-4 ]

Reference： [1]Green Chemistry,2015,vol. 17,p. 1408 - 1413
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18
[ 1073-67-2 ]
[ 507-19-7 ]
[ 54512-75-3 ]
1-chloro-4-[6-chloro-1-(2,2-dimethyl-propyl)-hexyl]-benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1998,vol. 120,p. 11822 - 11823

19
[ 110-91-8 ]
[ 1073-67-2 ]
[ 622-98-0 ]
[ 81321-33-7 ]
(E)-N-[2-(4-Chlorophenyl)ethyl]morpholine [ No CAS ]

Reference： [1]Chemistry - A European Journal,1999,vol. 5,p. 1306 - 1319

20
[ 1073-67-2 ]
[ 1012-12-0 ]
[ 61488-89-9 ]

Reference： [1]Pest Management Science,2001,vol. 57,p. 191 - 202

21
[ 1073-67-2 ]
[ 1791-26-0 ]
[ 123524-45-8 ]

Reference： [1]Helvetica Chimica Acta,2002,vol. 85,p. 352 - 387

22
[ 1073-67-2 ]
[ 14070-51-0 ]
[ 917-58-8 ]
[ 75-05-8 ]
2-[2-(4-chlorophenyl)aziridin-1-ylsulfonyl]benzoic acid ethyl ester [ No CAS ]
2-[4-(4-chlorophenyl)-2-methyl-4,5-dihydroimidazol-1-ylsulfonyl]benzoic acid ethyl ester [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3313 - 3315

23
[ 1073-67-2 ]
[ 201230-82-2 ]
[ 2019-34-3 ]
[ 938-95-4 ]

Yield	Reaction Conditions	Operation in experiment
	With water; toluene-4-sulfonic acid; triphenylphosphine; lithium chloride; In butanone; at 114.84℃; under 40504.1 Torr; for 12h;Autoclave;Catalytic behavior; Kinetics;	Carbonylation2 reactions were carried out in a 50 mL Parr autoclave reactor made of Hastelloy C-276 material following a procedure similar to that described previously [8]. For a typical reaction, the solid catalyst and the liquid phase reactants/solvent were charged in the reactor and sealed. The contents were heated to the desired temperature, then CO gas was introduced to the reactor to the desired pressure and the reaction started by switching on the stirring. The consumed CO was made up from a reservoir through a constant pressure regulator. The progress of the reaction was followed by observing the pressure drop in a CO reservoir as a function of time and the reaction was stopped at completion of CO absorption. Afterwards, the reactor was brought to ambient temperature, its content-gas was released and flushed thrice with N2 and liquid phase samples were analyzed for reactant/products composition using HP GC 6890 fitted with a HP-FFAP capillary column (25 m × 0.33 mm × 0.2 mum). GC-MS analyses of the samples were performed using Agilent 5973 N Mass Selective Detector attachment.

Reference： [1]Heterocycles,2004,vol. 63,p. 2797 - 2803
[2]Catalysis Today,2012,vol. 198,p. 154 - 173
[3]Chemical Communications,2018,vol. 54,p. 3967 - 3970

24
[ 623-73-4 ]
[ 1073-67-2 ]
[ 4157-47-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 142 - 159

25
[ 1073-67-2 ]
[ 628-51-3 ]
(+/-)-3-chloro-3-(4-chlorophenyl)propan-1-ol [ No CAS ]

Reference： [1]Synthesis,2006,p. 1427 - 1432

26
[ 1073-67-2 ]
[ 4251-65-4 ]

Yield	Reaction Conditions	Operation in experiment
86%	With ammonium persulfate; Pd(E-2-(benzylthio)-N-{(2-methoxynaphthalene-1-yl)methylene}benzenamine)Cl; 1-butyl-3-methylimidazolium Tetrafluoroborate; In water; at 70℃; for 0.25h;Microwave irradiation;	General procedure: To a homogeneous solution of Pd(II) complex (0.5 mol%) in 10 ml[bmim]BF4eH2O (2:1), substituted styrene (1 mmol) was added,followed by ammonium persulfate (1.5 mmol) as oxidant weretaken in glass tubes, sealed and placed in the cavity of microwaveapparatus. Then set parameters are as follows: microwave irradiationpower 80W, increasing time 5 min, target temperature 70 C,standing time 15 min, standing temperature 70 C. A maximumirradiation power of 80Wand 70 C were applied for 15 min. Afterthe temperature reached 70 C, the instrument was automaticallyadjusted to maintain a constant temperature. After completion of the reaction (monitored through TLC), the reaction mixture wascooled to room temperature then diluted with 2 10 ml water,then extracted with ethyl acetate and dried over Na2SO4. Theresulting solution was concentrated under vacuum. Product wasfurther purified by chromatographic separation with a mixture ofethyl acetate:hexane (1:10)

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 1125 - 1130
[2]Journal of Organometallic Chemistry,2016,vol. 822,p. 20 - 28
[3]Chemical Communications,2012,vol. 48,p. 5497 - 5499
[4]Chemical Communications,2016,vol. 52,p. 335 - 338
[5]Chemistry - A European Journal,2006,vol. 12,p. 949 - 955
[6]Chemical Communications,2011,vol. 47,p. 10963 - 10965
[7]ChemCatChem,2016,vol. 8,p. 2393 - 2400
[8]Journal of the American Chemical Society,2016,vol. 138,p. 12037 - 12040
[9]ACS Catalysis,2017,vol. 7,p. 5225 - 5233

27
[ 1073-67-2 ]
[ 201230-82-2 ]
[ 938-95-4 ]

Reference： [1]Organic Letters,1999,vol. 1,p. 459 - 461
[2]Chemical Communications,2018,vol. 54,p. 3967 - 3970

28
[ 1073-67-2 ]
[ 36603-49-3 ]
[ 3972-65-4 ]
4-tert-butyl-N-(4-(tetrahydro-2H-pyran-2-yloxy)phenyl)-N-(4-vinylphenyl)aniline [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 10354 - 10355

29
[ 1073-67-2 ]
[ 191109-51-0 ]

Reference： [1]Tetrahedron,1997,vol. 53,p. 6337 - 6350

30
[ 1073-67-2 ]
[ 4157-47-5 ]

Reference： [1]Journal of medicinal and pharmaceutical chemistry,1962,vol. 5,p. 1243 - 1265
[2]Monatshefte fur Chemie,2017,vol. 148,p. 2143 - 2153

31
[ 617-86-7 ]
[ 1073-67-2 ]
[ 622-98-0 ]
[ 75476-56-1 ]
(4-chlorophenethyl)triethylsilane [ No CAS ]

Reference： [1]Chemistry - A European Journal,2009,vol. 15,p. 2121 - 2128

32
[ 1073-67-2 ]
[ 373-88-6 ]
(+/-)-1-chloro-4-((trans)-2-(trifluoromethyl)cyclopropyl)benzene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 938 - 941
[2]Journal of the American Chemical Society,2017,vol. 139,p. 5293 - 5296

33
[ 1073-67-2 ]
[ 3038-48-0 ]
(E)-2-(2-(4-chlorostyryl)-6-(trifluoromethyl)phenyl)acetic acid [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2010,vol. 132,p. 14137 - 14151

34
[ 1073-67-2 ]
[ 69655-76-1 ]
octakis[2-(4-chlorophenyl)ethenyl]octasilsesquioxane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%		Example XIIA 5 mL reactor, equipped with a magnetic stirrer, a reflux condenser with an attachment enabling the reaction system to be connected to a vacuum-and-gas line was filled under inert gas with 0.01 g (1.58 10'5 mol) <strong>[69655-76-1]octavinylsilsesquioxane</strong>, followed, in the following order, with 3 mL methylene chloride and 0.015 mL (1.26*10"4 mol) 4- chlorostyrene. The reaction mixture was warmed to 45°C while stirring continuously. Then 0.0009 g (1.26x 10"6 mol) [chlorohydridocarbonylbis(tricyclohexyl- phosphine)ruthenium(II)] was added to the mixture and 5 minutes later 0.0006 g (6.32x 10"6 mol) copper(I) chloride was introduced. The reaction mixture was heated for24 hours at a temperature of 45°C. Then the solvent was subjected to vacuum evaporation and the residue was dissolved in a mixture of hexane and methylene chloride at a ratio by volume of hexane : CH2C12 = 10: 1 and transferred to a silica- packed chromatographic column to purify the product. This produced octakis[2-(4- chlorophenyl)ethenyl]octasilsesquioxane in the form of white powder with a yield of 94percent. Melting range: 300-302°C.lH NMR (C6D6, ppm): delta = 6.44 (d, 8H, J = 19.0 Hz, =CHSi), 6.97 (s, 32H, C6H4-C1),7.53 (d, 8H, J = 19.0 Hz, =CH-Ar)13C NMR (C6D6, ppm): delta = 117.9 (=CHSi), 128.5 (o-C of CeiijCl), 129.2 (m-C of C6H4C1), 135.5 (ipso-C at CI of Q^Cl), 135.7 (ipso-C of C6H4C1), 149.1(=CHAr)29Si NMR (C6D6, ppm): delta = -78.06APPI-MS: m/z ([M+H]+, percent intensity): 1512 (23), 1513 (26), 1514 (57), 1515 (79), 1516 (92), 1517 (95), 1518 (100), 1520 (80), 1521 (65), 1522 (46), 1523 (32), 1524 (20), 1525 (13)

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 887 - 891
[2]Patent: WO2012/23867,2012,A1 .Location in patent: Page/Page column 10-11

35
[ 1073-67-2 ]
[ 373-88-6 ]
(+)-1-chloro-4-(1S,2S)-(2-(trifluoromethyl)cyclopropyl)benzene [ No CAS ]
[ 1276183-95-9 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 1101 - 1104
[2]Journal of the American Chemical Society,2017,vol. 139,p. 5293 - 5296

36
[ 1073-67-2 ]
[ 201230-82-2 ]
[ 622-98-0 ]
[ 286964-62-3 ]
[ 75677-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	With C24H23Cl3P2Pt; hydrogen; tin(ll) chloride; In toluene; at 50℃; under 30003 Torr; for 96h;Autoclave; Inert atmosphere;	In a typical experiment a solution of 0.02 mmol of 7 and 0.04 mmol of tin(II)chloride in 10 mL toluene containing 1 mmol of styrene was transferred under argon into a 100 mL stainless steel autoclave. The reaction vessel was pressurized to 80 bar total pressure (CO/H2 = 1/1) and placed in an oil bath of appropriate temperature and the mixture was stirred with a magnetic stirrer for the appropriate reaction time. The pressure was monitored throughout the reaction. After cooling and venting of the autoclave, the pale yellow solution was removed and immediately analysed by GC.
	With C24H23Cl3P2Pt; hydrogen; tin(ll) chloride; In toluene; at 100℃; under 30003 Torr; for 24h;Autoclave; Inert atmosphere;	In a typical experiment a solution of 0.02 mmol of 7 and 0.04 mmol of tin(II)chloride in 10 mL toluene containing 1 mmol of styrene was transferred under argon into a 100 mL stainless steel autoclave. The reaction vessel was pressurized to 80 bar total pressure (CO/H2 = 1/1) and placed in an oil bath of appropriate temperature and the mixture was stirred with a magnetic stirrer for the appropriate reaction time. The pressure was monitored throughout the reaction. After cooling and venting of the autoclave, the pale yellow solution was removed and immediately analysed by GC.
	With cis-[bis(1-propyl-3-methyl-3-phospholeno)-dichloro-platinum(II)]; hydrogen; tin(ll) chloride; In toluene; at 100℃; under 60006 Torr; for 48h;Inert atmosphere;	General procedure: A solution of 0.01mmol of PtCl2(ligand)2 and 3.8mg (0.02mmol) of tin(II) chloride in 10 mL of toluene containing 0.115 mL (1mmol) of styrene was transferred under argon into a 100 mL stainless steel autoclave. The reaction vessel was pressurized to 80 bar total pressure (CO/H2 = 1/1) and placed in an oil bath of appropriate temperature and the mixture was stirred with a magnetic stirrer. Samples were taken from the mixture and the pressure was monitored throughout the reaction. After cooling and venting of the autoclave, the pale yellow solution was removed and immediately analyzed by GC and chiral GC (on a capillary Cyclodex-column, (S)-2- phenylpropanal was eluted before the (R) enantiomer).

Reference： [1]Journal of Organometallic Chemistry,2011,vol. 696,p. 2234 - 2237
[2]Journal of Organometallic Chemistry,2011,vol. 696,p. 2234 - 2237
[3]Journal of Organometallic Chemistry,2011,vol. 696,p. 3557 - 3563
[4]Heteroatom Chemistry,2011,vol. 22,p. 730 - 736
[5]Chemistry - A European Journal,2013,vol. 19,p. 16906 - 16909

37
[ 1073-67-2 ]
[ 1071-36-9 ]
[ 1592-11-6 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 4470 - 4474

38
[ 1073-67-2 ]
[ 7099-88-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	With potassium permanganate; sodium hydroxide; In water; at 70℃; for 0.5h;	General procedure: The aryl styrene 0.2mol, 0.4mol sodium hydroxide, water 80mL added to 500mL round bottom flask, heated to 70 C, potassium permanganate 0.5mol within 0.5h added in batches after 10min and then reused Ethanol 50mL will notThe reaction of potassium permanganate destruction, the reaction solution was suction filtered, the filtrate was retained, most of the water was distilled off under reduced pressure, the concentrated filtrate was acidified with concentrated hydrochloric acid, and then extracted with dichloromethane to remove the solvent, cooled to give a light The yellow solid was recrystallized from ethanol to give 2-aryl-2-oxoacetic acid.According to General Method 1, 2-(4-chlorophenyl)-2-oxoacetic acid was obtained as a white powder with a yield of 60.0%.

Reference： [1]Archives of Pharmacal Research,2010,vol. 33,p. 1641 - 1649
[2]Patent: CN105949220,2016,A .Location in patent: Paragraph 0115; 0116

39
[ 109-99-9 ]
[ 1073-67-2 ]
[ 3147-55-5 ]
[ 1346678-27-0 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 6456 - 6459

40
[ 1073-67-2 ]
[ 52449-43-1 ]
[ 99-91-2 ]

Reference： [1]Chemistry - A European Journal,2012,vol. 18,p. 1073 - 1076

41
[ 1073-67-2 ]
[ 106-49-0 ]
[ 622-98-0 ]
[ 1572529-88-4 ]
[ 1500603-32-6 ]
[ 99-91-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 2397 - 2403

42
[ 1073-67-2 ]
[ 106-47-8 ]
[ 622-98-0 ]
[ 1572529-86-2 ]
[ 1506289-20-8 ]
[ 99-91-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 2397 - 2403

43
[ 1073-67-2 ]
[ 100-00-5 ]
[ 622-98-0 ]
[ 1572529-86-2 ]
[ 1506289-20-8 ]
[ 99-91-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 2397 - 2403

44
[ 1073-67-2 ]
[ 99-99-0 ]
[ 622-98-0 ]
[ 1572529-88-4 ]
[ 1500603-32-6 ]
[ 99-91-2 ]

Reference： [1]Journal of Organic Chemistry,2014,vol. 79,p. 2397 - 2403

45
[ 1073-67-2 ]
[ 201230-82-2 ]
(R)-2-(4-chlorophenyl)propanal [ No CAS ]
[ 622-98-0 ]
[ 312304-85-1 ]
[ 75677-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 60℃; under 60006 Torr; for 140h;Autoclave; Schlenk technique;	General procedure: In a typical experiment, a solution of PtCl2[(R)-BINAP] (4.5 mg;0.005 mmol) and tin(II) chloride (1.9 mg; 0.01 mmol) in toluene(5 mL) containing styrene derivatives (1a-g, 5a-g) (1.0 mmol) wastransferred under argon into a 100 mL stainless steel autoclave. Thereaction vessel was pressurized to 80 bar total pressure (CO/H2 1:1) and placed in an oil bath of constant temperature. Themixture was stirred with a magnetic stirrer for the given reactiontime. The pressure was monitored throughout the reaction. Aftercooling and venting of the autoclave, the pale yellow solution wasremoved and immediately analyzed by GC-MS and chiral GC.
	With {(R)-binap}PtCl2; hydrogen; tin(ll) chloride; In toluene; at 100℃; under 60006 Torr; for 24h;Autoclave; Schlenk technique;	General procedure: In a typical experiment, a solution of PtCl2[(R)-BINAP] (4.5 mg;0.005 mmol) and tin(II) chloride (1.9 mg; 0.01 mmol) in toluene(5 mL) containing styrene derivatives (1a-g, 5a-g) (1.0 mmol) wastransferred under argon into a 100 mL stainless steel autoclave. Thereaction vessel was pressurized to 80 bar total pressure (CO/H2 1:1) and placed in an oil bath of constant temperature. Themixture was stirred with a magnetic stirrer for the given reactiontime. The pressure was monitored throughout the reaction. Aftercooling and venting of the autoclave, the pale yellow solution wasremoved and immediately analyzed by GC-MS and chiral GC.

Reference： [1]Organometallics,2014,vol. 33,p. 1389 - 1396
[2]Organometallics,2014,vol. 33,p. 1389 - 1396
[3]Journal of Organometallic Chemistry,2016,vol. 824,p. 118 - 123
[4]Journal of Organometallic Chemistry,2016,vol. 824,p. 118 - 123

46
[ 1073-67-2 ]
[ 16078-30-1 ]
(E)-1-(7-(4-chlorostyryl)indolin-1-yl)ethanone [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2014,vol. 9,p. 1257 - 1260

47
[ 1073-67-2 ]
[ 22286-82-4 ]
[ 1629188-45-9 ]

Reference： [1]Advanced Synthesis and Catalysis,2014,vol. 356,p. 1501 - 1508
[2]Journal of the American Chemical Society,2015,vol. 137,p. 3169 - 3172

48
[ 1073-67-2 ]
[ 1482-82-2 ]
[ 64-19-7 ]
2‑(benzylselanyl)‑1‑(4‑chlorophenyl)ethyl acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	With 3-chloro-benzenecarboperoxoic acid; potassium bromide; at 20℃; for 3h;	General procedure: A typical procedure for the catalytic acetoxyselenenylation of alkenes using KBr or NaCl as catalyst includes: In AcOH (AR, 99.5%, 1.5mL), alkene 1a (0.6mmol), diselenide 2a (0.2mmol), KBr (0.08mmol) and mCPBA (0.4mmol) were added successively. The suspension mixture was vigorously stirred at r.t. for 3h. Upon completion, the reaction was quenched by addition of sat. aq Na2S2O3 (2mL), sat. aq Na2CO3 (8mL) and H2O (5mL). The mixture was extracted with CH2Cl2 (3× 5mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified by TLC technique (4:1 (v/v) petroleum ether/ethyl acetate) to furnish 2-acetoxy-1-selenenylation compounds 3a [31] in 90% yield.
70%	With 3-chloro-benzenecarboperoxoic acid; potassium iodide; at 20℃; for 2h;	General procedure: In AcOH (1mL), alkene 1 (0.24mmol), diselenide 2 (0.1mmol), KI (0.02mmol) and m-CPBA (0.1mmol) were added successively. The suspension mixture was vigorously stirred at r. t. for 2h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2mL), basified with sat. aq. Na2CO3 (8mL) and H2O (5mL). The mixture was extracted with CH2Cl2 (3×5mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified on a silica gel plate (4:1 petroleum ether-ethyl acetate) to furnish 2-acetoxy-1-selenenylation compound 3.
70%	With 3-chloro-benzenecarboperoxoic acid; potassium iodide; at 20℃; for 2h;	General procedure: In AcOH (1mL), alkene 1 (0.24mmol), diselenide 2 (0.1mmol), KI (0.02mmol) and m-CPBA (0.1mmol) were added successively. The suspension mixture was vigorously stirred at r. t. for 2h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2mL), basified with sat. aq. Na2CO3 (8mL) and H2O (5mL). The mixture was extracted with CH2Cl2 (3×5mL) and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The residue was then purified on a silica gel plate (4:1 petroleum ether-ethyl acetate) to furnish 2-acetoxy-1-selenenylation compound 3.

70%

With iodine; In acetonitrile; at 20℃; for 16h;

General procedure: in MeCN (1.0 mL), alkene 1(0.24 mmol), diselenide 2 (0.1 mmol), carboxylic acid3 (2.0 mL), and I2(0.1 mmol) were added successively.The mixture was vigorously stirred at r.t. for 16 h. Upon completion, the reaction was quenched by addition of sat.aq Na2S2O3(2 mL), basified with sat. aq Na2CO3(8 mL)and H2O(5 mL). The mixture was extracted with CH2Cl2(3 × 5 mL), and the combined organic phase was dried over anhydrous Na2SO4,filtered, and concentrated under reduced pressure. The residue was then purified on a silica gel plate(4:1 petroleum ether:ethyl acetate) to furnish 2-acyloxy-1-selenenylation compounds 4.

Reference： [1]Chinese Chemical Letters,2015,vol. 26,p. 1117 - 1120
[2]Journal of Organometallic Chemistry,2015,vol. 776,p. 117 - 122
[3]Journal of Organometallic Chemistry,2015,vol. 776,p. 117 - 122
[4]Chemical Papers,2018,vol. 72,p. 2745 - 2752
[5]Helvetica Chimica Acta,2017,vol. 100

49
[ 1073-67-2 ]
[ 1889-71-0 ]
2,5-bis(4-chlorophenyl)-4-phenyl-2,3-dihydrofuran [ No CAS ]
C₂₂H₁₄Cl₂O [ No CAS ]

Reference： [1]Organic Letters,2014,vol. 16,p. 5446 - 5449

50
[ 1073-67-2 ]
[ 50-00-0 ]
[ 6282-88-8 ]
[ 59667-21-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 4632 - 4636

51
[ 1073-67-2 ]
[ 1864-94-4 ]
phenyl p-chloro-3-phenylpropionate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3544 - 3547

52
[ 1073-67-2 ]
[ 1864-94-4 ]
phenyl 2-(4-chlorophenyl)propanoate [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 3544 - 3547

53
[ 1073-67-2 ]
[ 369-57-3 ]
[ 1889-71-0 ]

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 7739 - 7745

54
[ 1073-67-2 ]
[ 6919-61-5 ]
(E)-2-(4-chlorostyryl)-N-methylbenzamide [ No CAS ]

Reference： [1]Chemistry - An Asian Journal,2015,vol. 10,p. 1505 - 1512

55
[ 1073-67-2 ]
[ 52898-49-4 ]
[ 1402849-83-5 ]

Reference： [1]Chemistry - An Asian Journal,2015,vol. 10,p. 1505 - 1512

56
[ 1073-67-2 ]
[ 354-38-1 ]
N-[1-(4-chlorophenyl)-2-iodoethyl]-2,2,2-trifluoroacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With tert-butylhypochlorite; sodium iodide; In acetonitrile; at -10℃; for 24h;Inert atmosphere; Darkness;	General procedure: To a solution of <strong>[354-38-1]trifluoroacetamide</strong> (2.00 g,18 mmol), NaI (7.95 g, 53 mmol) and styrene (2.05 mL, 18 mmol) in CH3CN (80 mL) t-BuOCl (6.10 mL, 53 mmol) was added dropwise in argon atmosphere in the dark and cooling to 10 C . The mixture was stirred for one day, the solvent removed under reduced pressure, the residue dissolved in diethyl ether (80 mL), washed with aqueous Na2S2O3 and dried over CaCl2. The solvent was removed in vacuum. Purification of the residue (5.57 g) by separation from resinification products on silica column with successive elution with hexane, ether-hexane (1:1) and ether recovered <strong>[354-38-1]trifluoroacetamide</strong> (0.4 g) and gave the title compound (9) (4.80 g, 79%), which was crystallized from methylene chloride. Colorless crystals, mp 109 C . gammamax (KBr) 3324, 3088, 3035, 2972,2951, 2913, 1699, 1553, 1496, 1455, 1365, 1216, 1182, 1076, 999, 885,804, 762, 729, 702, 655, 599, 573, 498 cm-1; deltaH (CDCl3), ppm: 7.45-7.35 (2H,m,CH), 7.33-7.26 (3H, m, CH), 7.00 (1H,d, J 5.5 Hz,NH), 5.14 (1H, ddd, J 7.1, 5.9, 5.5 Hz,CH), 3.58 (1H, dd, J 10.7, 5.9 Hz, CHB), 3.54 (1H, dd, J 10.7, 7.1 Hz, CHA); deltaC (CDCl3), ppm: 157.0 (q, J 37.6 Hz,C=O), 138.1 (Ci), 129.5 (Cm), 129.2 (Cp), 126.5 (Co), 116.0 (CF3, J 288.5 Hz), 54.9 (CHNH) 8.7 (ICH2).19F NMR, deltaF, ppm: 75.36. Anal. Calcd: C, 35.01; H, 2.64; N, 4.08; I 36.99; F 16.61. C10H9F3INO.Found: C, 35.02; H, 2.53; N, 3.98; I 37.10; F 16.56.

Reference： [1]Tetrahedron,2015,vol. 71,p. 8669 - 8675
[2]Journal of Molecular Structure,2017,vol. 1141,p. 351 - 356

57
[ 1073-67-2 ]
[ 3749-51-7 ]
C₁₄H₁₂ClNO₂ [ No CAS ]

Reference： [1]RSC Advances,2015,vol. 5,p. 78958 - 78961

58
[ 14345-97-2 ]
[ 1073-67-2 ]
C₁₃H₁₀Cl₂S [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 3115 - 3118

59
[ 1073-67-2 ]
[ 27257-15-4 ]
(E)-3-(4-chlorostyryl)-1-methyl-1H-pyrrolo[2,3-b]pyridine [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 900 - 903

60
[ 1073-67-2 ]
[ 71098-88-9 ]
[ 20469-61-8 ]
4-methoxy-2,3,6-trimethyl-1-[1-(4-chlorophenyl)-2-(phenylseleno)ethyl]benzene [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 912 - 915

61
[ 1073-67-2 ]
[ 3994-50-1 ]
(E)-5-(4-chlorostyryl)-1-methyl-4-nitro-1H-pyrazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 689 - 698

62
[ 873-73-4 ]
[ 1073-67-2 ]
[ 622-98-0 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 3627 - 3630
[2]New Journal of Chemistry,2019,vol. 43,p. 16583 - 16594

63
[ 1073-67-2 ]
[ 3038-48-0 ]
C₁₇H₁₂ClF₃O₂ [ No CAS ]

Reference： [1]Organic Syntheses,2016,vol. 92,p. 58 - 75

64
[ 1073-67-2 ]
[ 1482-82-2 ]
2-(benzylselanyl)-1-(4-chlorophenyl)ethanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With water; iodine; In ethyl acetate; at 20℃; for 12h;	General procedure: Alkenes 1 (0.24 mmol), diselenides 2 (0.10 mmol) and I2 (0.10 mmol) were added successively to MeCN/H2O (v/v, 1/1) (3 mL). The mixture was vigorously stirred at r. t. for 12 h. Upon completion, the reaction was quenched by addition of sat. aq. Na2S2O3 (2 mL),sat. aq. Na2CO3 (2 mL) and H2O (5 mL), respectively. The mixture was extracted with CH2Cl2 (3×5 mL) and the combined organic phase was dried over anhydrous Na2SO4,filtered, and concentrated under reduced pressure. The residue was then purified on a silica gel plate (4:1 petroleum ether-ethyl acetate) to furnish products 3.

Reference： [1]Chinese Chemical Letters,2018,vol. 29,p. 479 - 481
[2]Helvetica Chimica Acta,2016,vol. 99,p. 654 - 658

65
[ 1073-67-2 ]
[ 1864-94-4 ]
phenyl p-chloro-3-phenylpropionate [ No CAS ]
(R)-2-(p-chlorophenyl)propionic acid phenyl ester [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 5456 - 5459

66
[ 1073-67-2 ]
[ 1864-94-4 ]
(R)-2-(p-chlorophenyl)propionic acid phenyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	With (R)-((4,4?-bi-1,3-benzodioxole)-5,5?-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; palladium diacetate; In hexane; at 50℃; for 48h;Inert atmosphere; Sealed tube;	(R) -DTBM-SEGPHOS represents a chiral ligand, and HCOOPh stands for <strong>[1864-94-4]phenyl formate</strong>.Under the argon atmosphere, palladium acetate (0.025 mmol, 0.0056 g), chiral ligand (R) -DTBM-SEGPHOS (0.05 mmol, 0.059 g), 0.5 mL of n-hexane, p-chlorostyrene having the formula 3-f (0.5 mmol, 0.0693 g) and <strong>[1864-94-4]phenyl formate</strong> (1.5 mmol, 0.1832 g). Tighten the cap seal to adjust the heating plate temperature to 50 C. 48 hours After cooling, the mixture was cooled to room temperature and column chromatography (petroleum ether: ethyl acetate in a volume ratio of 100: 1) gave 0.1147 g The color liquid (R) -2- (p-chlorophenyl) propionate (see structure 4-f as described in the above reaction) yield 88% Linear ratio> 20: 1, enantiomeric excess 94%, HPLC conditions: chiral OJ-H column, n-hexane: isopropanol volume ratio of 90:10, flow rate: 1.0 mL / min, absorption Wavelength: 204nm.

Reference： [1]Patent: CN106431919,2017,A .Location in patent: Paragraph 0052; 0053; 0054; 0055; 0056

67
[ 1073-67-2 ]
[ 1950-68-1 ]
[ 130188-84-0 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tert.-butylhydroperoxide; tetrabutylammomium bromide; oxygen; In acetonitrile; at 60℃; under 760.051 Torr;Schlenk technique; Green chemistry;	General procedure: n-Bu4NBr (16.1 mg, 0.1 mmol) and TBHP (tert-butylhydroperoxide,46.0 mg, 1.0 mmol) were added to a solutionof styrene (1a, 52.0 mg, 0.5 mmol) and benzenesulfonohydrazide(2a, 94.6 mg, 0.55 mmol) in acetonitrile (2.0mL). The mixture was stirred at 60 C for 8.0 h in a Schlenktube and a balloon filled with O2 was attached to the sidearm. The reaction was monitored by TLC before it wasquenched with water (10 mL) and extracted with dichloromethane(5×3 mL). The extracted organics were dried overanhydrous sodium sulfate and the solvent was removed underreduced pressure. The residue was purified by flash silicagel column chromatography using ethyl acetate/petroleumether (1:6) as eluent to give the desired compound 3aas a white solid (252.0 mg, 84%).

Reference： [1]Science China Chemistry,2017,vol. 60,p. 353 - 357

68
[ 1073-67-2 ]
[ 136-85-6 ]
[ 1666-13-3 ]
C₂₁H₁₈ClN₃Se [ No CAS ]
C₂₁H₁₈ClN₃Se [ No CAS ]

Reference： [1]RSC Advances,2017,vol. 7,p. 15709 - 15714

69
[ 1892-22-4 ]
[ 1073-67-2 ]
C₁₄H₁₈N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
20 g		11.4 g of alpha-aminopentylactam was dissolved in 100 m of anhydrous tetrahydrofuran,Add 2.4 g of metal sodium,After 30 min reaction,16 g of p-vinylbenzene chloride was dissolved in 10 ml of anhydrous tetrahydrofuran,Was added dropwise to the above solution,30min drop finished.After the reaction was continued for 60 min,Steamed to remove the solvent after adding chloroform dissolved,The organic phase was washed three times with deionized water,Add anhydrous potassium carbonate for drying.After drying the solvent,20 g Compound 1 was obtained.

Reference： [1]Patent: CN106588754,2017,A .Location in patent: Paragraph 0066; 0067

70
[ 1073-67-2 ]
[ 373-88-6 ]
(+)-1-chloro-4-(1S,2S)-(2-(trifluoromethyl)cyclopropyl)benzene [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 5293 - 5296

71
[ 1073-67-2 ]
[ 20035-08-9 ]
1-chloro-4-[(E)-2-(ethylsulfonyl)ethenyl]benzene [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 2179 - 2185

72
[ 1073-67-2 ]
[ 100-63-0 ]
[ 1889-71-0 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 2941 - 2944

73
[ 1073-67-2 ]
[ 1950-68-1 ]
1-(4-chlorophenyl)-2-((4-methoxyphenyl)sulfonyl)ethan-1-one oxime [ No CAS ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 5794 - 5799

74
[ 1073-67-2 ]
[ 43189-37-3 ]

Reference： [1]Advanced Synthesis and Catalysis,2017,vol. 359,p. 4305 - 4316

75
[ 1073-67-2 ]
[ 4387-36-4 ]
[ 62100-12-3 ]

Yield	Reaction Conditions	Operation in experiment
88.2%	With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In N,N-dimethyl acetamide; at 110℃; for 20h;	S1: The reaction formula of this step is as follows.The specific reaction operation is: at room temperature,Adding 100 mmol of the compound of the above formula (III) to an appropriate amount of the organic solvent N,N-dimethylacetamide (DMA),175 mmol of the above compound of formula (IV), 0.6 mmol of palladium acetate,125 mmol of tetra-n-butylammonium bromide and 175 mmol of sodium carbonate, and then the temperature was raised to 110 C with stirring.And stirring the reaction at this temperature for 20 hours;After the reaction was completed, the reaction mixture was poured into a sufficient amount of ethyl acetate.After washing with saturated brine, the organic layer and the aqueous layer were separated.After the aqueous layer is sufficiently extracted with ethyl acetate,The organic layers are combined (ie, the organic layer washed with saturated brine and the organic layer obtained by ethyl acetate extraction).Dry with anhydrous Na2SO4 and distill under reduced pressure.The residue was eluted by flash column chromatography (a mixture of petroleum ether and ethyl acetate in a volume ratio of 8:1).The eluent was collected and evaporated to remove the eluent.Thus obtaining a compound of the above formula (II) as a white solid in a yield of 88.2%
88.2%	With tetrabutylammomium bromide; palladium diacetate; sodium carbonate; In N,N-dimethyl acetamide; at 20 - 110℃; for 20h;	The specific reaction operation is:100 mmol of the compound of the above formula (II), 175 mmol of the compound of the above formula (III), 0.6 mmol of palladium acetate, and an appropriate amount of the organic solvent N,N-dimethylacetamide (DMA) were added at room temperature.125 mmol of tetra-n-butylammonium bromide and 175 mmol of sodium carbonate,Then stir to raise the temperature to 110 C,And stirring the reaction at this temperature for 20 hours;After the reaction was completed, the reaction mixture was poured into a sufficient amount of ethyl acetate.After washing with saturated brine,The organic layer and the aqueous layer were separated, and the aqueous layer was sufficiently extracted with ethyl acetate.The combined organic layers (i.e., the organic layer washed with saturated brine and organic layer extracted from ethyl acetate) were dried over anhydrous Na2SO?The residue was eluted by flash column chromatography (a mixture of petroleum ether and ethyl acetate in a ratio of 8:1 as eluent).The eluent was collected and evaporated to remove the eluent.Thereby obtaining a compound of the above formula (I) as a white solidThe yield was 88.2%.
88.2%	With tetrabutylammomium bromide; palladium diacetate; In N,N-dimethyl acetamide; at 20 - 110℃; for 20h;	S1:100 mmol of the compound of the above formula (1), 175 mmol of the compound of the above formula (2), 0.6 mmol of palladium acetate, and an appropriate amount of the organic solvent N,N-dimethylacetamide (DMA) were added at room temperature.125 mmol of tetra-n-butylammonium bromide and 175 mmol of sodium carbonate, and then the temperature was raised to 110 C with stirring, and the reaction was stirred at this temperature for 20 hours;After the reaction was completed, the reaction mixture was poured into a sufficient amount of ethyl acetate, and then washed with saturated brine, and the organic layer and aqueous layer were separated, and the aqueous layer was extracted with ethyl acetate. The organic layer and the organic layer obtained by ethyl acetate extraction were dried over anhydrous Na 2 SO 4 and evaporated under reduced pressure. The elution is carried out, the eluent is collected and the eluent is removed by evaporation.Thus obtaining a compound of the above formula (3) as a white solid in a yield of 88.2%;

Reference： [1]Patent: CN108250162,2018,A .Location in patent: Paragraph 0114; 0115-0118; 0136; 0145; 0156; 0161
[2]Patent: CN108250103,2018,A .Location in patent: Paragraph 0057-0060; 0064-0069; 0072; 0075-0078; 0081; 0084
[3]Patent: CN108329290,2018,A .Location in patent: Paragraph 0118; 0120; 0122; 0123

76
[ 1073-67-2 ]
[ 101166-65-8 ]
[ 23665-09-0 ]
C₂₂H₃₁ClOSi [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 9801 - 9805

77
[ 1073-67-2 ]
[ 932-16-1 ]
(E)-1-(5-(4-chlorostyryl)-1-methyl-1H-pyrrol-2-yl)ethanone [ No CAS ]

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

78
[ 1073-67-2 ]
[ 6971-74-0 ]
(E)-N-Ts-3-(4-chlorobenzylidene)isoindolin-1-one [ No CAS ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7869 - 7874

79
[ 1073-67-2 ]
[ 622-98-0 ]
[ 5121-74-4 ]

Reference： [1]Catalysis science and technology,

80
[ 1073-67-2 ]
[ 68-12-2 ]
[ 14062-80-7 ]

Reference： [1]Applied Organometallic Chemistry,2019,vol. 33

81
[ 1073-67-2 ]
[ 381-98-6 ]
1-chloro-4-((1E,3E)-5,5,5-trifluoropenta-1,3-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
41%	With dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer; silver(I) acetate; In 1-methyl-pyrrolidin-2-one; at 120℃; for 6h;Inert atmosphere;	General procedure: Amixture of styrene (6a) (2 mmol, 208 mg), alpha-trifluoromethylacrylic acid (2) (0.5mmol, 70 mg), [Cp*RhCl2]2 (0.005 mmol, 3 mg), AgOAc (1 mmol, 167 mg) and1-methylnaphthalene (ca. 40 mg) as internal standard was stirred in NMP (2.5ml) under argon at 120 C for 6h. Then the reaction mixture was diluted byethyl acetate (30 ml). The organic layer was washed by 1 N HCl (30 ml), water30 (ml), and brine (30 ml) and dried over Na2SO4. After evaporation of thesolvents under vacuum, product 7a (101 mg, 93%) was isolated by columnchromatography on silica gel using hexane/EtOAc/AcOH=90/9/1 (v/v/v) as eluent.

Reference： [1]Chemistry Letters,2019,vol. 48,p. 461 - 464

82
[ 1073-67-2 ]
[ 13322-90-2 ]
C₂₈H₂₃ClO₅ [ No CAS ]

Reference： [1]Organic Letters,2019,vol. 21,p. 3038 - 3042

83
[ 1073-67-2 ]
[ 598-94-7 ]
4-(4-chlorophenyl)-N,N-dimethyl-4,5-dihydrooxazol-2-amine [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 11676 - 11680
Angew. Chem.,2019,vol. 131,p. 11802 - 11806,5

84
[ 1073-67-2 ]
[ 580-19-8 ]
[ 65-85-0 ]
C₂₄H₁₅ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetrakis(triphenylphosphine) palladium(0); triethylamine; In 1,4-dioxane; at 100℃; for 8h;	At room temperature, 610 mg (5 mmol) of benzoic acid 1a, 832 mg (6 mmol) of p-chlorostyrene 2b, and 721 mg (5 mmol) of <strong>[580-19-8]7-aminoquinoline</strong> 3a were added to a 25 mL round-bottomed flask, and then 578 mg (0.5 mmol) were sequentially added. Tetratriphenylphosphine palladium, 15 mL of 1,4-dioxane, and 1010 mg (10 mmol) of triethylamine were stirred at 100 C for 8 hours. After the reaction was completed, 15 mL of a saturated sodium chloride aqueous solution was added to the system, and extracted three times with 10 mL of ethyl acetate. The organic phases were combined, dried over anhydrous sodium sulfate, and the solvent was distilled off. Silica gel column chromatography of 200-300 mesh 4f pure product was obtained (1608 mg, yield 84%, pale yellow solid).

Reference： [1]Patent: CN110194760,2019,A .Location in patent: Paragraph 0047-0051

85
[ 1073-67-2 ]
[ 13436-48-1 ]
(E)-3-(4-chlorostyryl)-1-methyl-1H-indazole [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2020,vol. 85,p. 1009 - 1021

86
[ 1073-67-2 ]
[ 14062-05-6 ]
[ 40807-08-7 ]

Yield	Reaction Conditions	Operation in experiment
80%	With N-iodo-succinimide; triethylamine; In tetrahydrofuran; at 20℃; for 0.0833333h;	General procedure: To a stirred solution of phenylethene (1a, 52 mg, 0.5 mmol) and TsNHNHTs (4a, 170 mg, 0.5 mmol) in THF (2 mL) was sequentially added Et3N (152 mg, 1.5 mmol) and NIS (237 mg, 1 mmol) at room temperature. The release of N2 and the color change from orange to deep brown were observed immediately. Five minutes later, the reaction was quenched by adding saturated aqueous solution of Na2S2O3 (10 mL). The mixture was extracted by EtOAc (3 x 10 mL) and the combined organic layers were dried over Na2SO4. After the solvent was removed on a rotavapor, the residue was purified by a fresh chromatography (10% EtOAc in PE).

Reference： [1]Tetrahedron,2020,vol. 76

87
[ 1073-67-2 ]
[ 94-97-3 ]
1-(2-bromo-1-(4-chlorophenyl)ethyl)-5-chloro-1H-benzo[d][1,2,3]triazole [ No CAS ]
2-(2-bromo-1-(4-chlorophenyl)ethyl)-5-chloro-2H-benzo[d][1,2,3]triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%; 28%		General procedure: Styrene (1.0 equiv.) in anhydrous dichloromethane (5 mL) and NBS (2.0 equiv.) was taken into RB and reaction mixture was stirred at room temperature. After 30 min benzotriazole (2.0 equiv) dissolved in anhydrous DCM was added drop wise to the reaction mixture. After the completion of reaction as monitored by TLC, solvent was evaporated under vacuum. The reaction mixture was extracted with ethyl acetate and washed with hypo and brine solution. The organic layer obtained was dried over sodium sulphate, filtered and then evaporated under reduced pressure. Further purification was done by using flash column chromatography (SiO2).

Reference： [1]Tetrahedron,2020

88
[ 1073-67-2 ]
[ 64-18-6 ]
[ 201230-82-2 ]
[ 6282-88-8 ]
C₁₀H₁₁ClO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With bis(1,5-cyclooctadiene)diiridium(I) dichloride; 1,10-Phenanthroline; triethylamine; In 1,2-dichloro-ethane; at 120℃; under 3750.38 - 22502.3 Torr; for 16h;Autoclave; Sealed tube;	General procedure: In a typical experiment, [Ir(COD)Cl]2 (0.025mmol), L1 (0.05mmol) (or the other ligand) were mixed with styrene (5mmol, or the other olefin), FA (25mmol), Et3N (0.125mol if required) and DCE (2mL, or the other solvent). The mixture was added in a 50mL sealed Teflon-lined stainless steel autoclave which was purged with CO (0.5MPa) for three times and then pressured by CO to 3.0MPa. Then the reaction mixture was stirred vigorously at appointed temperature for some time. Upon completion, the autoclave was cooled down to room temperature and slowly depressurized. The solution was analyzed by GC to determine the conversions (n-dodecane as internal standard) and the selectivities (normalization method), and the products were further identified by GC-mass spectrometry.

Reference： [1]Journal of Catalysis,2020,vol. 385,p. 183 - 193

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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. 1073-67-2 ] {[proInfo.proName]}

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[ 1073-67-2 ] Synthesis Path-Upstream 1~20

[ 1073-67-2 ] Synthesis Path-Downstream 1~88

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