[ CAS No. 615-41-8 ] {[proInfo.proName]}

Name: 615-41-8|1-Chloro-2-iodobenzene|98% (stabilized with Copper chip)
Brand: Ambeed
SKU: A223951
Price: 5.0 USD
Availability: InStock
Rating: 91 (29 reviews)

,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 615-41-8

Structure of 615-41-8 * 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 [ 615-41-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 615-41-8 ]

SDS Specification

Alternatived Products of [ 615-41-8 ]

Product Details of [ 615-41-8 ]

CAS No. :	615-41-8	MDL No. :	MFCD00001033
Formula :	C₆H₄ClI	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MPEOPBCQHNWNFB-UHFFFAOYSA-N
M.W :	238.45	Pubchem ID :	11993
Synonyms :

Calculated chemistry of [ 615-41-8 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.17
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.15
Log Po/w (XLOGP3) :	3.71
Log Po/w (WLOGP) :	2.94
Log Po/w (MLOGP) :	3.79
Log Po/w (SILICOS-IT) :	3.51
Consensus Log Po/w :	3.22

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.21
Solubility :	0.0147 mg/ml ; 0.0000616 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.4
Solubility :	0.0947 mg/ml ; 0.000397 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.97
Solubility :	0.0256 mg/ml ; 0.000107 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 615-41-8 ]

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

Application In Synthesis of [ 615-41-8 ]

* 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 [ 615-41-8 ]
Downstream synthetic route of [ 615-41-8 ]

[ 615-41-8 ] Synthesis Path-Upstream 1~10

1
[ 201230-82-2 ]
[ 615-41-8 ]
[ 609-65-4 ]

Reference： [1] Journal of the American Chemical Society, 2013, vol. 135, # 45, p. 16841 - 16844

2
[ 108-90-7 ]
[ 108-95-2 ]
[ 637-87-6 ]
[ 625-99-0 ]
[ 615-41-8 ]

Reference： [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1987, p. 1167 - 1174

3
[ 615-41-8 ]
[ 7697-37-2 ]
[ 683238-59-7 ]
[ 32337-97-6 ]
[ 74534-15-9 ]
[ 41252-96-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 1071,1073

4
[ 615-41-8 ]
[ 873-31-4 ]

Reference： [1] Organic Letters, 2015, vol. 17, # 10, p. 2522 - 2525

5
[ 615-41-8 ]
[ 1906-57-6 ]
[ 7335-25-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With palladium diacetate In 1-methyl-pyrrolidin-2-one at 20 - 140℃; for 24 h; Inert atmosphere	General procedure: An oven-dried Schlenk-tube (10 mL) was charged with Pd source (1 mol percent), and ethyl potassium oxalate (0.75 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL) were added by syringe under a counter flow of argon at room temperature. The reaction vessel was closed and then placed under stirring in a preheated oil bath. The reaction mixture was stirred for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate, and analyzed by gas chromatography.

Reference： [1] Tetrahedron Letters, 2012, vol. 53, # 43, p. 5796 - 5799

6
[ 615-41-8 ]
[ 7697-37-2 ]
[ 683238-59-7 ]
[ 32337-97-6 ]
[ 74534-15-9 ]
[ 41252-96-4 ]

Reference： [1] Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 1071,1073

7
[ 13675-18-8 ]
[ 615-41-8 ]
[ 3900-89-8 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851

8
[ 615-41-8 ]
[ 73183-34-3 ]
[ 870195-94-1 ]

Yield	Reaction Conditions	Operation in experiment
32%	With pyridine; cesium fluoride In dimethyl sulfoxide at 105℃; for 2 h; Inert atmosphere; Schlenk technique	General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv) and bispinacolatodiboron (254 mg, 1 mmol, 2 equiv). Under an argon atmosphere, freshly distilled DMSO (0.4 mL), the appropriate aryl iodide (0.5mmol), and pyridine (0.4 to 1 equiv) were added successively. The reaction mixture was heated to 105 °C and stirred for 2 h under argon.

Reference： [1] Organic Letters, 2016, vol. 18, # 20, p. 5248 - 5251
[2] Synthesis (Germany), 2017, vol. 49, # 21, p. 4759 - 4768

9
[ 615-41-8 ]
[ 870195-94-1 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 4, p. 1842 - 1851

10
[ 615-41-8 ]
[ 1316215-12-9 ]

Reference： [1] Patent: US2015/176076, 2015, A1, . Location in patent: Page/Page column
[2] Patent: US2016/339022, 2016, A1,

[ 615-41-8 ] Synthesis Path-Downstream 1~88

1
[ 615-41-8 ]
[ 90064-46-3 ]
[ 100871-68-9 ]

Reference： [1]Acta Chemica Scandinavica (1947),1958,vol. 12,p. 537,542

2
[ 95-51-2 ]
[ 615-41-8 ]

Yield	Reaction Conditions	Operation in experiment
85%		General procedure: Aniline derivative (2 mmol) was dissolved in 1 ml of 37 % HCl. The mixture was stirred at 0-5 C for 10 min, until the ammonium salt was formed and the aromatic amine disappeared. The progress of the reaction was monitored by TLC [eluent: n-hexane/ethyl acetate (80:20)]. Nitrite ionic liquid (1 mmol) was added to the aniline solution. The reaction mixture was ground mildly for 5-10 min, the diazonium salt was formed.Then, KI (5 mmol, 0.41 g) was added to the mixture and stirring continued for 5-20 min at room temperature (Table 1). The mixture was filtered and washed with distilled water (3 x 8 ml) and ethyl acetate (EtOAc, 15 ml). The residue was extracted with EtOAc (3 9 10 ml) and the combined organic layer was washed with 10 % aqueous solution of Na2SO3 (15 ml) and then it was dried over anhydrous Na2SO4. The solvent was evaporated to afford aryl iodides.
77%		General procedure: To a stirring mixture of glacial acetic acid (0.12 mL, 2.1 mmol) and TBN (0.30 mL, ~2.3mmol)inethanol(10mL), Sac -H (0.37g, 2.0 mmol) was slowly added at low temperature (an ice bath). After 5 min, aniline derivative 1(a-l) (2.0 mmol) was added dropwise over 5 minutes into the mixture. The solvent, t -BuOH, and residue TBN were removed under reduced pressure after consuming of aniline derivatives (monitored by a color test of azo coupling with 2-naphthol). Then, 5 mL of 0.4 M TEAI solution was added into stirring as-obtained intermediate 2(a-l) in one portion at low temperature. After confirmation of substrate consumption by a negative test of azo coupling with 2-naphthol, the boiling water was added to the reaction mixture (15 mL) and the aqueous layer was separated. The organic layer was was hed with aq. 10% sodium sulphite (3 ×5 mL), then dried over Na2 SO4 , filtered, and dried under reduced pressure in a rotary evaporator. The purification was conducted by flash chromatography with n-hexane-EtOAc (9:1,v/v) as eluent.

Reference： [1]Research on Chemical Intermediates,2013,vol. 41,p. 3999 - 4007
[2]Tetrahedron Letters,1998,vol. 39,p. 4533 - 4536
[3]Tetrahedron Letters,1992,vol. 33,p. 3167 - 3168
[4]Turkish Journal of Chemistry,2020,vol. 44,p. 535 - 542
[5]Zeitschrift fur Physikalische Chemie (Leipzig),1930,vol. <B> 10,p. 106,119
[6]Journal of the Chemical Society. Perkin transactions II,1982,p. 1593 - 1598
[7]Bulletin of the Chemical Society of Japan,1997,vol. 70,p. 219 - 224

3
[ 615-41-8 ]
[ 20442-79-9 ]
[ 39655-06-6 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1972,vol. 762,p. 29 - 54

4
[ 201230-82-2 ]
[ 615-41-8 ]
[ 89-98-5 ]

Yield	Reaction Conditions	Operation in experiment
81%	With rhodium(III) chloride trihydrate; hydrogen; triethylamine; triphenylphosphine; In N,N-dimethyl acetamide; at 90℃; under 7500.75 Torr; for 12h;Autoclave;	General procedure: All reactions were carried out in an 80 mL Teflon-lined stainless steel reactor equipped with a magnetic stirring bar. Typically, in a glovebox, the aryl iodides (1.0 mmol), RhI3(0.025 mmol), PPh3 (0.1 mmol), Et3N (1.2 mmol), and DMA (2 mL) were loaded into the reactor. Then, the autoclave was screwed up, charged with CO and H2 to a total pressure of 10 bar (1:1) and transferred to an oil bath preheated at 90 C, which was controlled by a Haake-D3 temperature controller. After completion of the reaction, the reactor was cooled in iced water and the gas carefully vented. The conversion and yield of the aryl iodides and arylaldehydes were determined by GC analysis using dodecane as an internal standard. For yield determination of the other products, the reaction mixture was first analyzed by GC-MS to determine the structures of the aromatic aldehyde products. Then, CH2Cl2 (5 mL) was added to the reaction mixture, after which deionized water (10 mL) was added to extract the solvent DMA for 5 times. The organic layer was dried over anhydrous Na2SO4, concentrated by rotary evaporation and finally purified by column chromatography on silica gel using n-hexane/ethyl acetate as eluent to obtain the pure products and isolated yields.

Reference： [1]Beilstein Journal of Organic Chemistry,2020,vol. 16,p. 645 - 656
[2]Tetrahedron Letters,1990,vol. 31,p. 6887 - 6890

5
[ 615-41-8 ]
[ 292638-85-8 ]
[ 98288-14-3 ]

Yield	Reaction Conditions	Operation in experiment
56%	With 1-methyl-pyrrolidin-2-one; potassium carbonate at 150℃; for 24h;
55%	With IrCl(CO)(PPh₃)3; potassium carbonate In various solvent(s) at 150℃; for 24h;

Reference： [1]Iyer, Suresh; Ramesh, Chinnasamy; Sarkar, Anjana; Wadgaonkar, Prakash P. [Tetrahedron Letters, 1997, vol. 38, # 46, p. 8113 - 8116]
[2]Iyer, Suresh [Journal of Organometallic Chemistry, 1995, vol. 490, # 1-2, p. C27 - C28]

6
[ 615-41-8 ]
[ 292638-85-8 ]
[ 98288-14-3 ]
[ 108-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; triphenylphosphine In various solvent(s) at 130℃; for 24h; Yield given. Yields of byproduct given;

Reference： [1]Kelkar, Ashutosh A. [Tetrahedron Letters, 1996, vol. 37, # 49, p. 8917 - 8920]

7
[ 615-41-8 ]
[ 107-19-7 ]
[ 80151-26-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃; for 18h;Inert atmosphere;	General procedure: A solution of tert-butyl(2-iodophenoxy)dimethylsilane (6a) (0.80 g, 2.39 mmol) and triethylamine (3.35 ml, 23.92 mmol) in DMF (3 ml) was degassed by bubbling argon for 10 min, then propargyl alcohol (0.28 ml, 4.79 mmol) followed by [Pd(PPh3)4] (83 mg, 0.07 mmol) and CuI (27 mg, 0.14 mmol) were added. The reaction mixture was stirred for 7 h at rt, concentrated, diluted with water, and extracted with EtOAc. The organic extract was concentrated under reduced pressure and purified by column chromatography on silica gel (EtOAc in petroleum ether, 1:4) to give the product 7a (0.36 g, 45%) as a yellow oil 1H NMR (300 MHz, CDCl3) delta: 7.37 (dd, J = 7.6, 1.7 Hz, 1H), 7.20 (td, J = 8.1, 1.7 Hz, 1H), 6.90 (td, J = 7.6, 1.1 Hz, 1H), 6.82 (dd, J = 8.1, 1.1 Hz, 1H), 4.50 (d, J = 6.2 Hz, 2H), 1.53 (t, J = 6.2 Hz, 1H), 1.04 (s, 9H), 0.23 (s, 6H). LCMS (ESI) m/z: 263.10 [M+H]+.
95%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 23℃; for 24h;Inert atmosphere;	General procedure: A 100mL flask was charged with Pd(PPh3)Cl2 (70 mg, 0.1 mmol) and CuI (38 mg, 0.2 mmol). After the flask was evacuated and refilled with argon, NEt3 (20 mL) was added and the suspension was stirred at room temperature. A solution of iodobenzene (10a, 2.04 g, 10 mmol) and propargyl alcohol (616 mg, 11 mmol) in NEt3 (10 mL) was added to the suspension. After the reaction was complete (monitored by TLC), the mixture was filtered through a plug of Celite and washed with EtOAc (20 mL x 3). The combined solution was concentrated and purified by column chromatography on silica gel (Hexane/EtOAc 3:1, v/v) to afford 3-phenylprop-2-yn-1-ol (11a, 1.24 g, 94% yield) as a yellow oil.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 4314 - 4329
[2]Tetrahedron,2017,vol. 73,p. 4150 - 4159
[3]Organic Letters,2005,vol. 7,p. 4737 - 4739
[4]Journal of Medicinal Chemistry,1998,vol. 41,p. 2524 - 2536
[5]Journal of Medicinal Chemistry,1998,vol. 41,p. 1084 - 1091
[6]Organic and Biomolecular Chemistry,2016,vol. 14,p. 3878 - 3882
[7]Advanced Synthesis and Catalysis,2016,vol. 358,p. 1571 - 1576
[8]Angewandte Chemie - International Edition,2017,vol. 56,p. 9868 - 9871
Angew. Chem.,2017,vol. 129,p. 10000 - 10003,4
[9]Angewandte Chemie - International Edition,2018,vol. 57,p. 8734 - 8738
Angew. Chem.,2018,vol. 130,p. 8870 - 8874,5
[10]Chemistry - A European Journal,2019,vol. 25,p. 981 - 984
[11]Green Chemistry,2019,vol. 21,p. 509 - 514
[12]Advanced Synthesis and Catalysis,2019,vol. 361,p. 1108 - 1116
[13]Organic Letters,2020,vol. 22,p. 3765 - 3769

8
[ 6324-50-1 ]
[ 615-41-8 ]
[ 62796-65-0 ]

Reference： [1]Chemosphere,1995,vol. 31,p. 2687 - 2705

9
[ 615-41-8 ]
[ 3032-81-3 ]
[ 37680-68-5 ]

Reference： [1]Chemosphere,1995,vol. 31,p. 2687 - 2705

10
[ 615-41-8 ]
[ 64634-61-3 ]
[ 70362-48-0 ]

Reference： [1]Chemosphere,1995,vol. 31,p. 2687 - 2705

11
[ 615-41-8 ]
[ 38411-20-0 ]
[ 70362-45-7 ]

Reference： [1]Chemosphere,1995,vol. 31,p. 2687 - 2705

12
[ 615-41-8 ]
[ 40972-86-9 ]
[ 947683-05-8 ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 5510 - 5512
[2]Journal of Organic Chemistry,2007,vol. 72,p. 5960 - 5967
[3]Chemical Communications,1999,p. 2259 - 2260

13
[ 615-41-8 ]
[ 7697-37-2 ]
[ 683238-59-7 ]
[ 32337-97-6 ]
[ 74534-15-9 ]
[ 41252-96-4 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1936,vol. 55,p. 1071,1073

14
[ 615-41-8 ]
[ 87666-57-7 ]
(2-chloro-phenyl)-[1,1';3',1'']terphenyl-2'-yl-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With palladium diacetate; tri-tert-butyl phosphine; sodium t-butanolate In toluene at 110℃; for 14h;

Reference： [1]Wenderski, Todd; Light, Kenneth M.; Ogrin, Doug; Bott, Simon G.; Harlan, C. Jeff [Tetrahedron Letters, 2004, vol. 45, # 37, p. 6851 - 6853]

15
[ 615-41-8 ]
[ 7390-62-7 ]
8-(2-chloro-phenylsulfanyl)adenine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 3230 - 3232
[2]Journal of Medicinal Chemistry,2015,vol. 58,p. 3922 - 3943

16
[ 615-41-8 ]
[ 107-18-6 ]
[ 157433-36-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrabutyl-ammonium chloride; sodium hydrogencarbonate;palladium diacetate; In N,N-dimethyl-formamide; at 30℃; for 24h;Inert atmosphere;	Example 5: N-{3-(2-chlorophenyl)-l-[(4-methylpiperidin-l-yl)carbonyl]propyl} benzenesulfonamide <n="54"/>A mixture of 2.2 niL (18 mmol) of 2-chloroiodobenzene, 1.8 mL (27 mmol) of allyl alchohol, 81 mg (0.36 mmol) of Pd(OAc)2, 5.3 g (18 mmol) of Bu4NCl, and 3.8 g (45 mmol) of NaHCO3 in 50 mL of DMF is stirred under Ar2 at 30 0C for 24 h. Water is added and the mixture is extracted with EtOAc. The extract is washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (0-50% EtOAc in hexanes) provides 2.2 g (74%) of 3-(2-chlorophenyl)propenal.
40%	With tetrabutyl-ammonium chloride; sodium hydrogencarbonate;palladium diacetate; In N,N-dimethyl-formamide; at 30℃; for 24h;	EXAMPLE 7; Procedures for the Synthesis of 7-Chloro-3-(2-chlorophenethyl)-5-(2-oxo-2,3-dihydro-lH- imidazo[4,5-b]pyridin-6-yl)-lH-benzo[e][l,4]diazepin-2(3H)-one; Beginning with 2-Chloro- iodobenzene and Allyl Alcohol .; Step l 3-(2-Chlorophenyl)propanal. 2-Chloro-iodobenzene (700 mg), allyl alcohol (256 mg, 1.5 eq.), palladium acetate (13 mg, 0.02 eq), sodium bicarbonate (616 mg, 2.5 eq), and tetrabutylammonium chloride (816 mg, 1 eq) were mixed together in anhydrous DMF (12 mL). The mixture was stirred at 30 0C for 24 h, then diluted with water. The crude mixture was extracted into EtOAc 3x, and the organic layer was washed with water twice, then brine, and then dried over sodium sulfate, and concentrated. The residue was purified by chromatography (gradient: 88:12 hexanes:EtOAc to 1: 1 hexanes:EtOAc) delivering the product (200 mg, 40% yield). 1H-NMR (300 MHz, CDCl3) delta 9.80 (s, IH), 7.38 - 7.30 (m, IH), 7.28 - 7.10 (m, 3H), 3.10 - 3.02 (m, 2H), 2.84 - 2.68 (m, 2H).
	With tetrabutyl-ammonium chloride; sodium hydrogencarbonate;palladium diacetate; In N,N-dimethyl-formamide; at 45℃; for 22h;Sealed tube;	Solid tetrabutylammonium chloride (1.2 g, 4.2 mmol) was added to a DMF solution (5.5 mL) Of Pd(OAc)2 (57 mg, 0.1 mmol), NaHCO3 (880 mg, 10.5 mmol), l-chloro-2-iodo-benzene (1.0 g, 4.2 mmol), and allyl alcohol (370 mg, 6.29 mmol) in a sealed tube and the mixture was heated to 45 0C. After 22 h at 45 0C, the solution was cooled to room temperature; water was added, and the aqueous phase was extracted with ether, dried (Na2SO4) and concentrated to give 0.66 g of the title compound that was used in the next step without further purification.

With tetrabutyl-ammonium chloride; sodium hydrogencarbonate;palladium diacetate; In N,N-dimethyl-formamide; at 45℃; for 22h;sealed tube;

Solid tetrabutylammonium chloride (1.2 g, 4.2 mmol) was added to a DMF solution (5.5 mL) Of Pd(OAc)2 (57 mg, 0.1 mmol), NaHCO3 (880 mg, 10.5 mmol), l-chloro-2-iodo-benzene (1.0 g, 4.2 mmol), and allyl alcohol (370 mg, 6.29 mmol) in a sealed tube and the mixture was heated to 45 0C. After 22 h at 45 0C, the solution was cooled to room temperature; water was added, and the aqueous phase was extracted with ether, dried (Na2SO4) and concentrated to give 0.66 g of the title compound that was used in the next step without further purification.

Reference： [1]Organic Letters,2014,vol. 16,p. 4420 - 4423
[2]Journal of the American Chemical Society,2001,vol. 123,p. 12202 - 12206
[3]Chemistry - A European Journal,2018,vol. 24,p. 16516 - 16520
[4]Patent: WO2009/142984,2009,A1 .Location in patent: Page/Page column 51-52
[5]Synthesis,2008,p. 883 - 886
[6]Journal of Heterocyclic Chemistry,2004,vol. 41,p. 941 - 946
[7]Patent: WO2010/121164,2010,A2 .Location in patent: Page/Page column 71-72
[8]Patent: WO2010/45009,2010,A1 .Location in patent: Page/Page column 48
[9]Patent: WO2010/45013,2010,A1 .Location in patent: Page/Page column 29-30
[10]Angewandte Chemie - International Edition,2017,vol. 56,p. 6558 - 6562
Angew. Chem.,2017,vol. 129,p. 6658 - 6662,5

17
[ 615-41-8 ]
[ 536-74-3 ]
[ 10271-57-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; at 30℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: For example, synthesis of 1,2-diphenylethyne, 3a. To an oven-dried 5 mL microwave vessel was added Pd(PPh3)2Cl2 (3.5 mg, 0.005 mmol, 2 mol %) and CuI (1.9 mg, 0.01 mmol, 4 mol %). The vessel was then capped and purged with N2 before addition of Cyrene (0.5 mL, 0.5 M), Et3N (38 muL, 0.275 mmol, 1.1 equiv), iodobenzene (27.9 muL, 0.25 mmol, 1 equiv), and phenylacetylene (28.8 muL, 0.263 mmol, 1.05 equiv). The reaction mixture was heated to 30 C and maintained at this temperature with stirring for 1 h before the vessel was vented, and decapped. The solution was then diluted with EtOAc (10 mL), and washed with water (2× 20 mL) and brine (2 × 20 mL). The organics were then passed through a hydrophobic frit and concentrated under reduced pressure to give a yellow oil, which was purified by flash chromatography (silica gel, 0-5% Et2O in petroleum ether) to afford the title compound as a white solid (44.5 mg, quant.).
94%	With [{Pd(mu-Cl){kappa2-P,C-P(iPr)2(OC6H3-2-Ph)}}2]; triethylamine; In water; at 40℃; for 4h;Inert atmosphere;	Typical procedure: 0.01 ml of a catalyst stock solution (0.05 mol L-1) containing palladacycle 2 (20.0 mg, 2.35 mmol) in 0.47 ml of CH2Cl2 was placed in a Schlenk tube. The solvent was removed in vacuo and 0.2 mmol (1.0 equiv) of the appropriate aryl halide, 0.273 ml (2.0 mmol, 10.0 equiv) Et3N, and 2 ml deoxygenated H2O were added. The mixture was stirred vigorously for 15 min at 40 C. Subsequently, 0.2 mmol (1.0 equiv) of the respective aryl alkyne was added. The reaction mixture was stirred for 4 h at 40 C. Subsequently, 10% HCl (3 ml) and EtOAc (4 ml) were added. The layers were separated and the solvent was removed in vacuo. The residue was purified by flash chromatography using either hexane or hexane/EtOAc 10:1 as eluent to yield the pure product. GC yields are referenced to mesitylene as the internal standard;
94%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; isosorbide dimethyl ether; at 25℃; for 1h;Microwave irradiation; Inert atmosphere;	General procedure: To an oven-dried 5 mL microwave vessel was addedPd(PPh3)2Cl2 (2 mol%), aryl halide (1 equiv.), and alkyne couplingpartner (1.05 equiv.). The vessel was capped and purgedwith N2 before addition of DMI (0.5 mL, 0.5 M), and Et3N (1.1equiv.). The reaction mixture was maintained at room temperature(25 C) with stirring for 1 h before the vessel was ventedand decapped. The solution was then diluted with EtOAc (10mL) and washed with water (2 × 20 mL) and brine (2 × 20 mL).The organics were then passed through a hydrophobic frit andconcentrated under reduced pressure to give a residue, whichwas purified by flash chromatography (silica gel) to afford theproduct.

81%	With 1-Methylpyrrolidine; In water; at 20℃;	General procedure: To a mixture of the PVC-Pd catalyst (20 mg, 6.2 mol %) andiodobenzene (81.6 mg, 0.40 mmol) in H2O (3.0 mL) were addedphenylacetylene (81.7 mg, 0.80 mmol) and NMP (6.0 mmol). The reactionmixture was stirred at room temperature for 3-4 h and filtered. The filtratewas extracted twice with EtOAc (6 mL). The combined EtOAc extracts werewashed with water (4 mL) and brine (2 mL), dried over anhydrous Na2SO4, andconcentrated in vacuo. The resulting residue was chromatographed on silicagel (hexane-EtOAc, 100:1) to give quantitative yield of diphenylacetylene.
81%	With triethylamine; In water; at 80℃; for 24h;	General procedure: A 10 mL round-bottom flask was charged with iodobenzene (4a, 1 mmol, 1 eq.), phenylacetylene (7a, 1.5mmol, 1.5 eq.), triethylamine (3 mmol, 3 eq.), H2O (2 mL), and Pd catalyst (0.01 mmol). The flask was stirred at 80C in air. The reaction was monitored by TLC and GC. After the reaction was complete, the reaction mixture was cooled to room temperature and ethyl acetate (5mL) was added to the flask. Afterward, the catalyst was filtered and washed with water (10 mL) and ethyl acetate (10 mL). The aqueous phase was extracted three times with 30 mL EtOAc. The organic phases were collected together, dried over MgSO4, and filtered. The solvent was then evaporated under reduced pressure. The pure product was obtained via silica gel column chromatography with an eluent of EtOAc and hexane. The resulting product was analyzed by 1H NMR spectroscopy.
80%	With C19H25CuN5(1+)*F6P(1-); potassium carbonate; In N,N-dimethyl-formamide; at 135 - 140℃;Sealed tube;	General procedure: A 20mL scintillation vial was charged with a Teflon stir bar, copper complex (0.1mmol), 76 potassium carbonate (0.75mmol), aryl iodide (0.5mmol), 77 phenylacetylene (0.75mmol) in 5mL non-anhydrous DMF in air. The vial was sealed and placed in an oil bath with pre-adjusted temperature at 135-140C. After the allowed time, the reaction mixture was cooled down, diluted with 25-30mL ethyl acetate, and filtered through a pad of silica gel. The solvent was then removed under vacuum and the residue was purified by column chromatography using mixtures of hexane and ethyl acetate to obtain analytically pure product.
68%	With 1,4-diaza-bicyclo[2.2.2]octane; manganese(III) triacetate dihydrate; at 70℃;Green chemistry;	General procedure: In a 25 mL reaction tube, Mn(OAc)3.2H2O(10 mol%), DABCO (2.5 equiv.) and a stirring bar were added. Then iodobenzene(1 mmol), phenyl acetylene (1 mmol) and PEG-400 were injected by syringe. The reaction tube was closed and transferred to a 70 C oil bath for 19-24 hours. After the reaction completed, cool down the reaction mixture to room temperature. Water (2 mL) was added and the reaction mixture was extracted with ethyl acetate and then concentrated and purified by column chromatography.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 2005 - 2011
[2]ACS Catalysis,2019,vol. 9,p. 11640 - 11646
[3]Israel Journal of Chemistry,2014,vol. 54,p. 371 - 380
[4]Tetrahedron Letters,2011,vol. 52,p. 6355 - 6358
[5]Synlett,2018,vol. 29,p. 2293 - 2297
[6]Tetrahedron,2010,vol. 66,p. 1064 - 1069
[7]Journal of the Iranian Chemical Society,2014,vol. 11,p. 499 - 510
[8]Organic Letters,2008,vol. 10,p. 5281 - 5284
[9]Synlett,2008,p. 1415 - 1417
[10]Tetrahedron Letters,2014,vol. 55,p. 2256 - 2260
[11]Journal of Organometallic Chemistry,2014,vol. 769,p. 80 - 93
[12]Journal of Organometallic Chemistry,2018,vol. 860,p. 98 - 105
[13]Applied Organometallic Chemistry,2015,vol. 29,p. 674 - 677
[14]Tetrahedron Letters,2016,vol. 57,p. 1706 - 1710
[15]RSC Advances,2016,vol. 6,p. 109296 - 109300
[16]Tetrahedron,2005,vol. 61,p. 11311 - 11316
[17]Angewandte Chemie - International Edition,2009,vol. 48,p. 6879 - 6882
Angewandte Chemie,2009,vol. 121,p. 7011 - 7014
[18]Chemical Communications,2011,vol. 47,p. 1042 - 1044
[19]Chemical Communications,2014,vol. 50,p. 2261 - 2264
[20]RSC Advances,2015,vol. 5,p. 37995 - 38000

18
[ 627-27-0 ]
[ 615-41-8 ]
[ 54784-82-6 ]

Yield	Reaction Conditions	Operation in experiment
66%	With lithium acetate; tetrabutyl-ammonium chloride; lithium chloride In N,N-dimethyl-formamide at 40℃; for 28h;
	With lithium acetate; tetrabutyl-ammonium chloride; lithium chloride In N,N-dimethyl-formamide at 40℃; for 28h;

Reference： [1]Toracca, Karen E.; Kuwabe, Shin-Itsu; Buchwald, Stephen L. [Journal of the American Chemical Society, 2000, vol. 122, # 51, p. 12907 - 12908]
[2]Kuwabe; Torraca; Buchwald [Journal of the American Chemical Society, 2001, vol. 123, # 49, p. 12202 - 12206]

19
[ 615-41-8 ]
[ 65386-94-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With oxone; In water; acetonitrile; at 20℃; for 7h;	General procedure: Method a: A mixture of iodoarene 1a-o (1 mmol) and Oxone (2.46 g, 4 mmol) in 4 ml H2O-MeCN solution (3 : 1 v/v) was vigorously stirred until full conversion of substrate. The resulting mixture was poured into 20 ml of water and the precipitate was filtered. The obtained white solids were washed by water (3 x 10 ml) and organic solvent (1 x 10 ml) and dried in vacuum. Most products are partially soluble in water. Method b (Scale-up): The products 2a, 2d, 2e, 2i and 2o were also prepared in a larger scale using 10 mmol of iodoarene.

Reference： [1]Journal of Organic Chemistry,2006,vol. 71,p. 9912 - 9914
[2]Tetrahedron Letters,2016,vol. 57,p. 4254 - 4256
[3]Tetrahedron,2010,vol. 66,p. 5745 - 5752

20
[ 615-41-8 ]
[ 493-08-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 85 percent / tetrabutylammonium chloride; sodium bicarbonate; palladium acetate / dimethylformamide / 22 h / 45 °C 2: 98 percent / sodium borohydride / methanol / 20 °C 3: 87 percent / Pd(OAc)2; Cs₂CO₃; 2-(di-tert-butylphosphanyl)-1,1'-binaphthyl / toluene / 21 h / 65 °C
	Multi-step reaction with 3 steps 1: 85 percent / tetrabutylammonium chloride; sodium bicarbonate; palladium acetate / dimethylformamide / 22 h / 45 °C 2: 98 percent / sodium borohydride / methanol / 20 °C 3: 87 percent / Pd(OAc)2; di-tert-butyl-[2-(1,1'-binaphthyl)]phosphine; Cs₂CO₃ / toluene / 21 h / 65 °C

21
[ 615-41-8 ]
[ 90875-76-6 ]

Reference： [1]Journal of the American Chemical Society,2000,vol. 122,p. 12907 - 12908
[2]Journal of the American Chemical Society,2001,vol. 123,p. 12202 - 12206
[3]Patent: WO2017/96045,2017,A1

22
[ 615-41-8 ]
[ 2358-41-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 55 percent / dimethylformamide 2: 40 percent / CrO₃ / 100 °C 3: 13 percent Chromat_. / tetra-n-butylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

Reference： [1]Beaumont, Andrew J.; Clark, James H. [Journal of Fluorine Chemistry, 1991, vol. 52, # 3, p. 295 - 300]

23
[ 223576-64-5 ]
[ 615-41-8 ]
5-chloro-2-(2-chlorophenyl)benzofuran [ No CAS ]

Reference： [1]Patent: EP1266897,2002,A2 .Location in patent: Page 35

24
[ 615-41-8 ]
tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate [ No CAS ]
[ 864830-05-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 90℃; for 1h; Inert atmosphere;	36.36-1 Step 36-1 tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-carboxylate (309 mg, 1 mmol), 1-chloro-2-iodobenzene (238 mg, 1 mmol), potassium carbonate (207 mg, 1.5 mmol), and bistriphenylphosphinepalladium dichloride (70.2 mg, 0.1 mmol) were added to a mixture of dimethoxyethane and water (2:1 volume ratio) (12 mL), and the resulting mixture was heated at 90°C for 1 hour in a nitrogen atmosphere. A 10% aqueous potassium hydrogen sulfate solution was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by preparative silica gel column chromatography (hexane/ethyl acetate) to give 287.2 mg of tert-butyl 4-(2-chlorophenyl)-3,6-dihydropyridin-1(2H)-carboxylate (yield: 98%). 1H NMR (CDCl3, 400 MHz) δ7.34 - 7.37 (m, 1 H), 7.19 - 7.23 (m, 2 H), 7.15 - 7.18 (m, 1 H), 5.62 - 5.72 (br, 1 H), 4.02 - 4.08 (br, 2 H), 3.60 - 3.66 (bt, 2 H, J = 5.4 Hz), 2.41 - 2.48 (br, 2 H), 1.50 (s, 9 H). LC-MS: r.t. 3.77 min., m/z 238 (M+1-C4H8).
	With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 17h;	25.2 In a nitrogen atmosphere, 1.72 mL of 1-chloro-2-iodobenzene, 5.31 g of potassium carbonate and 474 mg of chloro[1,1'-bis(diphenylphosphino)ferrocene]palladium were added in that order to N,N-dimethylformamide (51 mL) solution of 3.95 g of the compound obtained in the above 1, and stirred at 80°C for 17 hours. Aqueous saturated sodium hydrogencarbonate solution was added to the reaction liquid, extracted with ethyl acetate, and the ethyl acetate layer was washed with saturated saline water and dried with anhydrous sodium sulfate. The solvent was evaporated off under reduced pressure, and the residue was separated and purified through silica gel column chromatography (hexane/ethyl acetate = 90/10) to obtain 1.61 g of the entitled compound as a pale yellow oily substance.

Reference： [1]Current Patent Assignee: OSAKA UNIVERSITY; KYOTO UNIVERSITY; NATIONAL INSTITUTES OF NATURAL SCIENCES - EP3789383, 2021, A1 Location in patent: Paragraph 0306-0307
[2]Current Patent Assignee: MERCK & CO INC - EP1726590, 2006, A1 Location in patent: Page/Page column 62-63

25
[ 82-73-5 ]
[ 615-41-8 ]
[ 74-88-4 ]
8-bromo-4-(2-chlorophenyl)-(2H)phthalazin-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium carbonate; hydrazine hydrate; magnesium In tetrahydrofuran; ethanol; water; ethyl acetate; N,N-dimethyl-formamide	R.59 Reference Example 59 Reference Example 59 Dry tetrahydrofuran (7 ml) was added to a mixture of 2-chloroiodobenzene (1.19 g) and magnesium (146 mg). The mixture was stirred for one hour at 60 °C under argon atmosphere. On the other hand, a solution of 3-bromophthalic anhydride (908 mg) in dry tetrahydrofuran (9 ml) was cooled to -5 °C, to which was added dropwise, under argon atmosphere, the above-mentioned Grignard reagent. The ice bath was removed, and the reaction mixture was warmed up to room temperature. To the reaction mixture was added 1N hydrochloric acid (6 ml), which was stirred for 30 minutes. To the mixture were added ethyl acetate and water. The mixture was shaken and, then left standing to form two layers. The upper layer was subjected to extraction with 0.2N sodium hydroxide (35 ml). The aqueous layer was made acid with hydrochloric acid, which was subjected to extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (anhydrous sodium sulfate) and concentrated under reduced pressure to give a pale yellow solid product (0.80 g). This product was dissolved in DMF (5 ml), to which were added potassium carbonate (970 mg) and methyl iodide (710 mg). The mixture was stirred for 14 hours at room temperature. To the reaction mixture were added ethyl acetate (50 ml) and water (30 ml). The mixture was shaken and, then, left standing to form two layers. The upper layer was washed with water, dried (anhydrous sodium sulfate) and concentrated under reduced pressure to give a colorless oily product. This product was dissolved in ethanol (3 ml), to which was added hydrazine hydrate (50 ml). The mixture was heated for 13 hours under reflux. The reaction mixture was cooled in air. Then, the resulting crystalline precipitate was collected by filtration, washed with a small volume of ethanol and dried to give 8-bromo-4-(2-chlorophenyl)-(2H)phthalazin-1-one (120 mg) as colorless needles.

Reference： [1]Current Patent Assignee: TAKEDA PHARMACEUTICAL COMPANY LIMITED - EP825187, 1998, A1

26
[ 615-41-8 ]
[ 104-52-9 ]
K₄[Fe(CN)6]*3H₂O [ No CAS ]
[ 960137-84-2 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 15372 - 15379

27
[ 1029684-37-4 ]
[ 615-41-8 ]
C₁₄H₁₅ClN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; cesium fluoride In N,N-dimethyl-formamide Heating;

Reference： [1]Primas, Nicolas; Mahatsekake, Clément; Bouillon, Alexandre; Lancelot, Jean-Charles; Oliveira Santos, Jana Sopkovà-de; Lohier, Jean-François; Rault, Sylvain [Tetrahedron, 2008, vol. 64, # 20, p. 4596 - 4601]

28
[ 3581-87-1 ]
[ 615-41-8 ]
[ 1050507-09-9 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 140℃; for 24h;	Step A: l-chloro-2-iodobenzene (500 muL, 4.1 mmol) is dissolved in DMF (10 niL), then <strong>[3581-87-1]<strong>[3581-87-1]2-<strong>[3581-87-1]methylthiazol</strong></strong>e</strong> (406 mg, 4.1 mmol), triphenylphosphine (54 mg, 0.20 mmol), cesium carbonate (1.33 g, 4.1 mmol), palladium(II) acetate (92 mg, 0.41 mmol) are added and the mixture is stirred at 140 0C for 24 h. The reaction mixture is diluted with 1 M HCl (10 mL) and extracted into EtOAc (3 x 10 mL). The organic layers are combined and washed with H2O (2 x 20 mL) and brine (10 mL), then dried (MgSO4), filtered, concentrated and purified by silica gel chromatography (EtOAc/hexane, gradient) to give 5-(2-chlorophenyl)-<strong>[3581-87-1]<strong>[3581-87-1]2-<strong>[3581-87-1]methylthiazol</strong></strong>e</strong> 6. 1H- NMR (400 MHz, CDCl3) delta = 7.80 (s, IH), 7.48 (m, 2H), 7.28 (m, 2H), 2.75 (s, 3H). MS calcd. for CI0H9CINS (M+H+) 210.0, found 210.1.

Reference： [1]Patent: WO2008/103501,2008,A1 .Location in patent: Page/Page column 22

29
[ 615-41-8 ]
[ 55-21-0 ]
[ 1020-39-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 110℃; for 48h;Schlenk technique; Inert atmosphere;	General procedure: An oven-dried Schlenk tube was charged with benzamide 1 (0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and aryl iodide 2 (1.0 mol). The tube was evacuated and backfilled with N2 (3 ×), and then DMEDA (0.2 mmol) and anhyd toluene (5.0 mL) were added. The reaction mixture was stirred at 110 C for 48 h. H2O was added and the crude product was extracted with EtOAc. The combined organic phases were washed with brine and H2O, dried (Na2SO4), and concentrated under reduced pressure. The product was purified by silica gel chromatographyto give the desired N-arylated benzamides (Table 2).

Reference： [1]Synlett,2008,p. 1335 - 1340
[2]Synthesis,2018,vol. 50,p. 1090 - 1096
[3]Chemistry - A European Journal,2008,vol. 14,p. 3527 - 3529
[4]Organic and biomolecular chemistry,2014,vol. 12,p. 7478 - 7481

30
[ 615-41-8 ]
[ 106-49-0 ]
[ 4630-20-0 ]

Reference： [1]Synthesis,2009,p. 3493 - 3503

31
[ 52670-38-9 ]
[ 615-41-8 ]
[ 1201632-24-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; diethylamine In N,N-dimethyl-formamide at 50℃; Inert atmosphere;
87%	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); copper (I) iodide; triethylamine at 20℃; Inert atmosphere;	2. Experimental procedure for the Synthesis of 2-((2-bromophenyl)ethynyl)aniline derivatives (S1a-j) General procedure: A 50 mL oven dried round bottom flask was charged with a magnetic stir-bar, Pd(PPh3)2Cl2(0.04 mmol), CuI (0.04 mmol) and 1-bromo-2-iodobenzene(b, 10 mmol). To this was addedtriethylamine (TEA) under the nitrogen atmosphere. Followed by the drop wise addition of 2-ethynylaniline (a, 10 mmol). The resultant reaction mixture was then allowed to stir at roomtemperature for overnight. Once the completion of reaction was confirmed by using TLC, themixture was diluted with ethyl acetate and was filtered through a celite pad and wash with ethylacetate. The organic layer was concentrated under reduced pressure and purified using columnchromatography (PE : EtOAc 8 : 2) giving product 2-((2- bromophenyl)ethynyl)aniline S1.

Reference： [1]Peng, Changlan; Wang, Yong; Liu, Lanying; Wang, Honggen; Zhao, Jiaji; Zhu, Qiang [European Journal of Organic Chemistry, 2010, # 5, p. 818 - 822]
[2]Aoki, Shin; Balachandran, Chandrasekar; Maheswari, Narayanan Uma; Mayakrishnan, Sivakalai; Perumal, Paramasivan T.; Sivaraman, Mahalingam [Synlett, 2022, vol. 33, # 8, p. 785 - 790]

32
[ 615-41-8 ]
[ 25776-12-9 ]
[ 80254-76-8 ]

Reference： [1]Tetrahedron,2010,vol. 66,p. 7633 - 7641

33
[ 615-41-8 ]
[ 71-43-2 ]
[ 92-52-4 ]
[ 84-15-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 29% 2: 40%	With potassium <i>tert</i>-butylate; N,N`-dimethylethylenediamine at 80℃; sealed tube; Inert atmosphere;
1: 28% 2: 22%	With potassium 2-methylbutan-2-olate; N,N`-dimethylethylenediamine at 80℃; for 24h; Inert atmosphere;	4.2. General procedure for direct C-H arylation of benzene with 4-iodoanisole General procedure: A Schlenk tube was charged with t-AmOK (1.5 mmol) under anatmosphere of nitrogen, and the solvent (toluene) was removedunder reduced pressure. Then 4-iodoanisole (117 mg, 0.5 mmol),ligand and benzene (4.0 mL) was added. The resulting mixture was stirred at 80 C for 24 h. After cooling to room temperature, the reaction mixture was quenched with water and extracted with ethyl acetate (10 mL3). The organic layers were combined, dried over Na2SO4 and concentrated under reduced pressure, and then purified by silica gel chromatograph (petroleum ether) to yield the desired product as a white solid.

Reference： [1]Location in patent: scheme or table Liu, Wei; Cao, Hao; Zhang, Hua; Zhang, Heng; Chung, Kin Ho; He, Chuan; Wang, Haibo; Kwong, Fuk Yee; Lei, Aiwen [Journal of the American Chemical Society, 2010, vol. 132, # 47, p. 16737 - 16740]
[2]Liu, Wei; Xu, Lige [Tetrahedron, 2015, vol. 71, # 30, p. 4974 - 4981]

34
[ 747392-34-3 ]
[ 615-41-8 ]
[ 1257871-99-0 ]

Reference： [1]Organic Letters,2010,vol. 12,p. 5692 - 5695

35
[ 615-41-8 ]
[ 95-51-2 ]

Yield	Reaction Conditions	Operation in experiment
74%	With acetamidine hydrochloride; caesium carbonate; In N,N-dimethyl-formamide; at 130℃; for 20h;Inert atmosphere; Green chemistry;	General procedure: A two-necked flask equipped with a magnetic stirring bar was charged with Cs2CO3 (2 or 3 mmol), MCM-41-L-proline-CuI (0.1 mmol), aryl iodide (1.0 mmol), acetamidine hydrochloride (1.2 or 2 mmol) and DMF (3.0 mL) under Ar. The reaction mixture was stirred at 130 or 140 C for 20 h. After being cooled to room temperature, the mixture was diluted with CH2Cl2 (10 mL) and filtered. The catalyst was washed with distilled water (2 × 5 mL) and EtOH (2 × 5 mL) and air dried when reused in the next run. The filtrate was concentrated with the aid of a rotary evaporator and the residue was purified by column chromatography on silica gel using petroleum ether (30-60 C)/ethylacetate (10:1 to 1:1) as eluent to give the desired product 2. All the products 2a-z are known compounds.
38%	With ammonium hydroxide; copper(l) iodide; N,N'-bis(3,5-dimethoxyphenyl)cyclopentane-1,1-dicarboxamide; caesium carbonate; In dimethyl sulfoxide; at 90℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: A 10 mL flask was charged with a magnetic stir bar, CuI (19 mg,10 mol%), L2 (86 mg, 20 mol%), Cs2CO3 (651 mg, 2 mmol) and solid aryl iodides (1.0 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). Under a counter flow of Argon, DMSO (1.0 mL), 1.0 mmol aryl iodides (if liquid), 0.9 mL (12.0 mmol) aqueous ammonia (28%) were added by syringe slowly. The reaction mixture was allowed to stir under argon at room temperature for 24 h. Then the mixture was diluted with 30 ml dichloromethane and passed through a fritted glass filter, the filter cake being further washed with 15 ml dichloromethane, dried over Na2SO4, filtered and the most solvent was removed under vacuum. The residue was purified by column chromatography on silica gel with an eluent of petroleum ether and ethyl acetate.

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 8224 - 8227
[2]Journal of Chemical Research,2017,vol. 41,p. 315 - 320
[3]Journal of Organic Chemistry,2011,vol. 76,p. 2296 - 2300
[4]Chinese Journal of Chemistry,2013,vol. 31,p. 501 - 506
[5]Tetrahedron Letters,2020

36
[ 292638-84-7 ]
[ 615-41-8 ]
[ 1657-52-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With potassium carbonate; In methanol; water; at 60℃; for 3h;	General procedure: In the typical procedure for the Heck coupling reaction, a mixture of iodobenzene (1 mmol), styrene (2 mmol), K2CO3 (5 mmol), and catalyst (0.14 g, Pd-PVP/KIT-6) in methanol-water (3:1) (5 mL) was placed in a round bottom flask. The suspension was stirred at 60 C for 8 h. The progress of reaction was monitored by Thin Layer Chromatography (TLC) using n-hexane/ethyl acetate (9:1) as eluent. After completion of the reaction (monitored by TLC), for the reaction work-up, the catalyst was removed from the reaction mixture by filtration, and then the reaction product was extracted with CH2Cl2 (3*5 mL). The solvent was removed under reduced pressure. The crude product was purified by flash column chromatography (hexane or hexane/ethyl acetate) to afford the desired coupling product (97% isolated yield). The product was identified with 1H NMR, 13C NMR and FT-IR spectroscopy techniques.
89%	With indium(III) chloride; sodium ethanolate; In N,N-dimethyl-formamide; at 140℃; for 24h;	General procedure: The reaction mixture of alkenes 1 (0.3 mmol), aryl iodides 2 (0.45 flask was stirred at 140 C, and monitored periodically by TLC. Upon completion, the reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (3×30 mL). The combined organic layers were washed with water and brine, dried over Na2SO4 and filtered. The solvent was removed under vacuum. The residue was purified by flash column chromatography to afford E-internal olefins 3.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3763 - 3766
[2]Comptes Rendus Chimie,2012,vol. 15,p. 988 - 995
[3]Materials Research Bulletin,2012,vol. 47,p. 160 - 166
[4]Tetrahedron,2013,vol. 69,p. 7925 - 7930

37
[ 615-41-8 ]
[ 137-07-5 ]
[ 92-84-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2-iodochlorobenzene; 2-amino-benzenethiol With ferric citrate In N,N-dimethyl-formamide at 110℃; Green chemistry; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 1h; Green chemistry; regioselective reaction;	Procedure for synthesis of compound (3 and 4) General procedure: 2-aminobenzenethiol (10 g, 80mmol), 3, 4-difluorobenzonitrile (11.12, 80mmol) and ferric citrate (19.59g, 80mmol) were added in DMF (50.00 mL) at 25-30 0C. The reaction mixture was heated to 110°C. Reaction mixture was monitored for the synthesis of compound 3 by TLC. (2ml of reaction mixture was withdrawn and separated in ethylacetate and water. Ethyl acetate solution concentrated and crystallised in isopropyl ether to give compound 3 for characterization). After completion of reaction by TLC, powdered potassium carbonate (16.58 g, 120mmol) was added to the solution and stirred for 1 hr. The mixture was heated to 110°C till completion by TLC. After completion of reaction, the mass was cooled to 25-30 °C. Ethyl acetate (150 mL) and DM water (150 mL) were added. Layers separated. Organic layer washed with water (150 mL), dried over sodium sulfate and concentrated. Isopropyl ether (IPE; 150 mL) was added to the slurry, filtered, washed with IPE. Dried under vacuum at 50 °C (16.84g, 94%).
64%	With copper(l) iodide; potassium carbonate In dimethyl sulfoxide at 120℃; for 48h; Inert atmosphere; regioselective reaction;

Reference： [1]Das, Tonmoy Chitta; Quadri, Syed Aziz Imam; Farooqui, Mazahar [Letters in Organic Chemistry, 2019, vol. 16, # 1, p. 16 - 24]
[2]Location in patent: experimental part Dai, Chuan; Sun, Xiaofei; Tu, Xingzhao; Wu, Li; Zhan, Dan; Zeng, Qingle [Chemical Communications, 2012, vol. 48, # 43, p. 5367 - 5369]

38
[ 934-37-2 ]
[ 615-41-8 ]
[ 1366591-30-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 1688 - 1691

39
[ 615-41-8 ]
[ 1906-57-6 ]
[ 7335-25-3 ]

Yield	Reaction Conditions	Operation in experiment
73%	With palladium diacetate; In 1-methyl-pyrrolidin-2-one; at 20 - 140℃; for 24h;Inert atmosphere;	General procedure: An oven-dried Schlenk-tube (10 mL) was charged with Pd source (1 mol %), and ethyl potassium oxalate (0.75 mmol). The tube was evacuated and backfilled with argon (this procedure was repeated three times). After that, iodobenzene (0.5 mmol) and NMP (1.0 mL) were added by syringe under a counter flow of argon at room temperature. The reaction vessel was closed and then placed under stirring in a preheated oil bath. The reaction mixture was stirred for 24 h. Upon completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate, and analyzed by gas chromatography.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 5796 - 5799

40
[ 615-41-8 ]
[ 4525-65-9 ]
2,4,6-trichlorophenyl 2-chlorobenzoate [ No CAS ]

Reference： [1]Organic Letters,2012,vol. 14,p. 5370 - 5373,4

41
[ 615-41-8 ]
[ 1068471-18-0 ]
[ 1206629-41-5 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 982 - 992

42
[ 615-41-8 ]
[ 1068471-18-0 ]
[ 1206629-42-6 ]

Reference： [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 982 - 992

43
[ 615-41-8 ]
[ 1428881-66-6 ]

Reference： [1]Patent: WO2013/49263,2013,A1

44
[ 2786-51-8 ]
[ 615-41-8 ]
[ 1443355-98-3 ]

Reference： [1]Synthesis,2013,vol. 45,p. 1247 - 1255

45
[ 615-41-8 ]
[ 40972-86-9 ]
[ 1438806-83-7 ]
4-trifluoromethyl-2'-chloro-2,3-dimethoxy-1,1'-biphenyl [ No CAS ]

Reference： [1]Chemical Communications,2013,vol. 49,p. 5510 - 5512

46
[ 844501-71-9 ]
[ 615-41-8 ]
[ 59843-55-9 ]

Yield	Reaction Conditions	Operation in experiment
99%	With caesium carbonate; tetrakis(triphenylphosphine)palladium (0); In 1,4-dioxane; water; at 150℃; for 0.833333h;Sealed tube; Microwave irradiation;	Step 1: 3-(2-Chlorophenyl)-1H-pyrazole A mixture of 1-chloro-2-iodobenzene (0.67 g, 2.8 mmol), <strong>[844501-71-9]3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (1.1 g, 5.6 mmol), tetrakis(triphenylphosphine)palladium(0) (0.65 g, 0.56 mmol), and cesium carbonate (4.6 g, 14 mmol) in 1,4-dioxane (18 mL) and water (2.0 mL) were sealed in a vial and subjected to microwave irradiation at 150 C. for 50 min. The organic solution was separated and concentrated. The residue was purified by column chromatography to give 3-(2-chlorophenyl)-1H-pyrazole (0.50 g, 99%). LCMS (FA): m/z=179 (M+H).

Reference： [1]Patent: US2013/165464,2013,A1 .Location in patent: Paragraph 0974

47
[ 615-41-8 ]
[ 38136-70-8 ]
[ 1454306-33-2 ]

Reference： [1]MedChemComm,2013,vol. 4,p. 1171 - 1174

48
[ 1493-13-6 ]
[ 615-41-8 ]
[ 108-67-8 ]
(2-chlorophenyl)(mesityl)iodonium trifluoromethanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: To a solution of the appropriate iodoarene(9.0 mmol) and mCPBA (85%) 2.5g in dichloromethane (25ml) at 0C was added trifluoromethanesulfonic acid (1.1 mL) dropwise over 2 mins. The ice bath wasthen removed and the reaction stirred for 2 hours at room temperature. It was then cooled to 0C andmesitylene (1.5 ml) was added dropwise over 2 minutes. The reaction was allowed to warm to room temperature and stirred overnight. The solvent was removed in vacuo and diethyl ether added. The resulting solid was filtered and washed on the filter with diethyl ether to give the iodonium triflate as a solid that was dried at 100 omicronC under vacuum for 1 hour.

Reference： [1]Synlett,2014,vol. 25,p. 1419 - 1424
[2]Chemical Communications,2016,vol. 52,p. 4987 - 4990
[3]Organic Letters,2013,vol. 15,p. 5654 - 5657
[4]Advanced Synthesis and Catalysis,2015,vol. 357,p. 371 - 376
[5]Chemistry - A European Journal,2015,vol. 21,p. 16801 - 16806
[6]Organic Letters,2015,vol. 17,p. 4136 - 4139
[7]Journal of Organic Chemistry,2017,vol. 82,p. 11735 - 11741
[8]Letters in Organic Chemistry,2013,vol. 10,p. 541 - 548

49
[ 201230-82-2 ]
[ 615-41-8 ]
[ 609-66-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With 1,4-diaza-bicyclo[2.2.2]octane; N-methoxylamine hydrochloride; sodium iodide; palladium dichloride; In acetonitrile; at 90℃; under 3800.26 Torr; for 8h;Autoclave; Inert atmosphere;	General procedure: To an autoclave (100 mL capacity), were added an arylhalide (1 mmol), methoxylamine hydrochloride (1.2 equiv),DABCO (2 equiv), PdCl2 (10 mol%), NaI (0.2 mmol) and MeCN (15 mL), under an inert atm. The autoclave was flushed three times with CO and then pressurized to 5 atm of CO. The mixture was stirred with a mechanical stirrer (550rpm) at 90 C for 8 h. The reactor was cooled to r.t., degassed carefully, opened and the reaction mixture removed. The reactor vessel was washed with EtOAc (2 × 5 mL) to remove residual product. The mixture was filtered and the filtrate washed with brine (2 × 4 mL), dried over Na2SO4, filtered and the solvent evaporated under vacuum. Purification of the residue was carried out by column chromatography (silicagel, 100-200 mesh, PE-EtOAc) to afford the corresponding product in good to excellent yield.

Reference： [1]Synlett,2014,vol. 25,p. 85 - 88

50
[ 201230-82-2 ]
[ 615-41-8 ]
[ 6638-79-5 ]
[ 289686-74-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With 1,4-diaza-bicyclo[2.2.2]octane; palladium diacetate; sodium carbonate In acetonitrile at 80℃; for 8h; Autoclave; Inert atmosphere;

Reference： [1]Gadge, Sandip T.; Bhanage, Bhalchandra M. [Organic and Biomolecular Chemistry, 2014, vol. 12, # 30, p. 5727 - 5732]

51
[ 615-41-8 ]
[ 42951-39-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: C₃₉H₅₁ClNOPPd; N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; caesium carbonate / toluene / 6 h / 90 °C / Sealed tube; Inert atmosphere 2: 16 h / 90 °C / Sealed tube; Inert atmosphere

Reference： [1]Rotta-Loria, Nicolas L.; Borzenko, Andrey; Alsabeh, Pamela G.; Lavery, Christopher B.; Stradiotto, Mark [Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 100 - 106]

52
[ 111-86-4 ]
[ 615-41-8 ]
[ 67-64-1 ]
[ 42951-39-3 ]

Yield	Reaction Conditions	Operation in experiment
44%	With N-[2-(di(1-adamantyl)phosphino)phenyl]morpholine; C₃₉H₅₁ClNOPPd; caesium carbonate In toluene at 90℃; for 16h;

Reference： [1]Rotta-Loria, Nicolas L.; Borzenko, Andrey; Alsabeh, Pamela G.; Lavery, Christopher B.; Stradiotto, Mark [Advanced Synthesis and Catalysis, 2015, vol. 357, # 1, p. 100 - 106]

53
[ 615-41-8 ]
[ 74-89-5 ]
[ 932-32-1 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 714 - 718

54
[ 615-41-8 ]
[ 1316215-12-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	In dimethyl sulfoxide;	Example 2 Synthesis of 2-((2-chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide (Compound B) Synthesis of Intermediate 2: See synthesis of intermediate 2 in Example 1. Synthesis of Intermediate 3: A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2-iodobenzene (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140° C. Work-up of the reaction gave compound 3 at 93percent yield. Synthesis of Intermediate 4: See synthesis of intermediate 4 in Example 1. Synthesis of Intermediate 6: See synthesis of intermediate 6 in Example 1.
	With nitrogen; potassium carbonate; aniline; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate;	Example 1 Synthesis of 2-((2-chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide (Compound A) Reaction Scheme: Experimental Procedure Synthesis of Intermediate 2: A mixture of aniline (3.7 g, 40 mmol), compound 1 (7.5 g, 40 mmol), and K2CO3 (11 g, 80 mmol) in DMF (100 ml) was degassed and stirred at 120° C. under N2 overnight. The reaction mixture was cooled to r.t. and diluted with EtOAc (200 ml), then washed with saturated brine (200 ml3). The organic layers were separated and dried over Na2SO4, evaporated to dryness and purified by silica gel chromatography (petroleum ethers/EtOAc=10/1) to give the desired product as a white solid (6.2 g, 64percent). Synthesis of Intermediate 3: A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2-iodobenzene (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140° C. Work-up of the reaction gave compound 3 at 93percent yield. Synthesis of Intermediate 4: 2N NaOH (200 ml) was added to a solution of compound 3 (3.0 g, 9.4 mmol) in EtOH (200 ml). The mixture was stirred at 60° C. for 30 min After evaporation of the solvent, the solution was neutralized with 2N HCl to give a white precipitate. The suspension was extracted with EtOAc (2200 ml), and the organic layers were separated, washed with water (2100 ml), brine (2100 ml), and dried over Na2SO4. Removal of the solvent gave a brown solid (2.5 g, 92percent). Synthesis of Intermediate 6: A mixture of compound 4 (2.5 g, 8.58 mmol), compound 5 (2.52 g, 12.87 mmol), HATU (3.91 g, 10.30 mmol), and DIPEA (4.43 g, 34.32 mmol) was stirred at r.t. overnight. After the reaction mixture was filtered, the filtrate was evaporated to dryness and the residue was purified by silica gel chromatography (petroleum ethers/EtOAc=2/1) to give a brown solid (2 g, 54percent). Synthesis of 2-((2-chlorophenyl)(phenyl)amino)-N-(7-(hydroxyamino)-7-oxoheptyl)pyrimidine-5-carboxamide (Compound A):

Reference： [1]Patent: US2015/176076,2015,A1 .Location in patent: Page/Page column
[2]Patent: US2016/339022,2016,A1

55
[ 864172-93-0 ]
[ 615-41-8 ]
C₁₉H₁₆ClN₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	[0240] A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	10411] A mixture of compound 2 (69.2 g, 1 equiv.),1-chioro-2-iodobenzene (135.7 g, 2 equiv.), Li2CO3 (42.04 g,equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 tm) inDMSO (690 ml) was degassed and purged with nitrogen. Theresulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	Synthesis of Intermediate 3 A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.

93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	Synthesis of Intermediate 3: [0166] A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	Synthesis of Intermediate 3 A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 mum) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	Synthesis of Intermediate 3: A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 jim) in DMSO (690 ml) was degassed and purged with nitrogen. The resultingmixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 jim) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140C. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 40℃; for 36h;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 tm)in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. for 36 hours. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 36h;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1equiv. 45 tm) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C for 36 hours. Work-up of the reaction gave compound 3 at 93 %yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), l-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muiotaeta) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muiotaeta) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93 % yield
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2CO3 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muiotaeta) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	10271] A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2CO3 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 am) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93% yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 36h;	Synthesis of Intermediate 3: A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muetaiota) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C for 36 hours. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 36h;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muetaiota) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C for 36 hours. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 36h;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muetaiota) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C for 36 hours. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 36h;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2- iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 muetaiota) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C for 36 hours. Work-up of the reaction gave compound 3 at 93 % yield.
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃; for 36h;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), <strong>[615-41-8]1-chloro-2-iodobenzene</strong> (135.7 g, 2 equiv.), Li2003 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1equiv. 45 .im) in DMSO (690 ml) was degassed and purged with nitrogen. The resultingmixture was stirred at 140 C for 36 hours. Work-up of the reaction gave compound 3 at 93%yield
93%	With lithium carbonate; copper; potassium carbonate; In dimethyl sulfoxide; at 140℃;Inert atmosphere;	A mixture of compound 2 (69.2 g, 1 equiv.), 1-chloro-2~ iodobenzene (135.7 g, 2 equiv.), Li2C03 (42.04 g, 2 equiv.), K2C03 (39.32 g, 1 equiv.), Cu (1 equiv. 45 pm) in DMSO (690 ml) was degassed and purged with nitrogen. The resulting mixture was stirred at 140 C. Work-up of the reaction gave compound 3 at 93 % yield.

Reference： [1]Patent: US2015/99744,2015,A1 .Location in patent: Paragraph 0240
[2]Patent: US2015/105384,2015,A1 .Location in patent: Paragraph 0411
[3]Patent: US2015/105358,2015,A1 .Location in patent: Paragraph 0400
[4]Patent: US2015/119413,2015,A1 .Location in patent: Paragraph 0165-0156
[5]Patent: US2015/105409,2015,A1 .Location in patent: Paragraph 0207
[6]Patent: US2015/105383,2015,A1 .Location in patent: Paragraph 0220
[7]Patent: US2015/150871,2015,A1 .Location in patent: Paragraph 0258
[8]Patent: WO2016/7423,2016,A1 .Location in patent: Page/Page column 38; 39
[9]Patent: WO2016/87950,2016,A1 .Location in patent: Page/Page column 27
[10]Patent: US2016/355486,2016,A1 .Location in patent: Paragraph 0144; 0146
[11]Patent: WO2016/200919,2016,A1 .Location in patent: Page/Page column 21; 22
[12]Patent: WO2017/143237,2017,A1 .Location in patent: Page/Page column 51
[13]Patent: WO2017/184774,2017,A1 .Location in patent: Page/Page column 45; 46
[14]Patent: WO2017/214565,2017,A1 .Location in patent: Paragraph 35; 36
[15]Patent: US2018/36306,2018,A1 .Location in patent: Paragraph 0266; 0270; 0271
[16]Patent: WO2018/81556,2018,A1 .Location in patent: Page/Page column 29-30
[17]Patent: WO2018/98168,2018,A1 .Location in patent: Page/Page column 32
[18]Patent: WO2018/85652,2018,A1 .Location in patent: Page/Page column 31
[19]Patent: WO2018/81585,2018,A1 .Location in patent: Page/Page column 34
[20]Patent: WO2018/98348,2018,A1 .Location in patent: Page/Page column 29; 30
[21]Patent: WO2019/106633,2019,A1 .Location in patent: Page/Page column 27-28

56
[ 615-41-8 ]
[ 1009-07-0 ]
[ 92-39-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With ferrous(II) sulfate heptahydrate; 1,10-Phenanthroline; potassium tert-butylate; In N,N-dimethyl-formamide; at 135℃; for 24h;Schlenk technique; Inert atmosphere;	Add to Schlenk tubeN- (2-mercapto) acetamide(0.3 mmol, 50.1 mg), FeSO47H2O (0.06 mmol, 16.68 mg),1,10-lindolinol (0.06 mmol, 10.8 mg) andPotassium tert-butoxide (1.2 mmol, 134.4 mg)With nitrogen to protect the reaction system (pumping gas three times),1,2-dibromobenzene (0.45 mmol, 105.2 mg) and DMF (2 mL) were added to the reaction system with a syringe,Heated to 135 C,Stirring reaction 24hAfter completion of the reaction, the mixture was cooled to room temperature,20 mL of water was added and extracted three times with ether,The organic phase was washed with water, dried over anhydrous sodium sulfate,Column chromatography to obtain the product10H-phenothiazine. Yield 70%.Using a similar approach,With o-dibromobenzene,O-chlorobenzene,O-chlorobenzene,O-dichlorobenzene was used in place of o-bromobenzene in Example 7,The yields of the product 2-chloro-10H-phenothiazine were 92%, 69%, 85%, 35%, respectively.

Reference： [1]Journal of Organic Chemistry,2015,vol. 80,p. 6128 - 6132
[2]Patent: CN104311508,2017,B .Location in patent: Paragraph 0018; 0019; 0032; 0033

57
[ 615-41-8 ]
[ 89291-23-6 ]
2'-chloro-N,N-dimethyl-(1,1'-biphenyl)-2-amine [ No CAS ]

Reference： [1]Organometallics,2015,vol. 34,p. 381 - 394

58
[ 615-41-8 ]
[ 936-59-4 ]
[ 22966-11-6 ]

Yield	Reaction Conditions	Operation in experiment
81%	With palladium diacetate; potassium carbonate; triphenylphosphine; In N,N-dimethyl-formamide; at 20 - 90℃; under 750.075 Torr; for 16h;Inert atmosphere;	General procedure: A mixture of Pd(OAc)2 (4.5 mg, 0.02 mmol), PPh3 (11.2 mg, 0.04 mmol), iodobenzene (1a) (82 mg, 0.4mmol), <strong>[936-59-4]3-chloropropiophenone</strong> (2a) (87 mg, 0.5 mmol), and K2CO3 (166 mg, 1.2 mmol) in DMF (2.5 mL) was stirred under a N2 atmosphere at room temperature for 10 min, and then heated at 90 C for 16 h. The reaction was then cooled to ambient temperature and diluted with CH2Cl2 (10 mL) before being filtered through a short pad of silica gel. The silica pad was rinsed with DCM (5 mL), and the combined filtrates were washed with brine (15 mL), dried over anhydrous Na2SO4. The solvent was then removed under reduced pressure to give the crude product as a residue, which was purified by silica gel column chromatography eluting with a mixture of petroleum ether (60-90 C)/EtOAc (v/v = 30:1).

Reference： [1]Chinese Journal of Catalysis,2015,vol. 36,p. 78 - 85

59
[ 615-41-8 ]
[ 118633-39-9 ]
[ 1016-78-0 ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 12664 - 12668
Angew. Chem.,2015,vol. 127,p. 12855 - 12859,5

60
[ 5765-65-1 ]
[ 615-41-8 ]
[ 1719-19-3 ]
4-(3-chloro-2-(phenylethynyl)phenyl)morpholine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With norbornene; palladium diacetate; caesium carbonate; triphenylphosphine In 1,4-dioxane at 20 - 100℃; for 18h; Inert atmosphere; Schlenk technique; chemoselective reaction;
72%	With norbornene; palladium diacetate; caesium carbonate; triphenylphosphine In 1,4-dioxane at 100℃; for 18h; Inert atmosphere; Schlenk technique;	4 Example 4 In a dry 25 mL Schlenk reaction tube, add 119 mg of 2-chloroiodobenzene,114mg of benzoyloxymorpholine, 96mg of 2-methyl-4-phenyl-3-butyn-2-ol,11mg of palladium acetate, 26mg of triphenylphosphine, 94mg of norbornene,489mg of cesium carbonate and 2.5mL of 1,4-dioxane. Under the protection of nitrogen,Stir at 100 ° C for 18 hours. After the reaction, cool to room temperature,Directly through the silica gel column (the body of ethyl acetate and petroleum etherThe product ratio is 1:30), 108 mg of product is obtained, the yield is 72%,

Reference： [1]Pan, Shanfei; Ma, Xueji; Zhong, Danni; Chen, Wanzhi; Liu, Miaochang; Wu, Huayue [Advanced Synthesis and Catalysis, 2015, vol. 357, # 14-15, p. 3052 - 3056]
[2]Current Patent Assignee: ZHEJIANG UNIVERSITY - CN104744190, 2016, B Location in patent: Paragraph 0044-0048

61
[ 201230-82-2 ]
[ 615-41-8 ]
[ 780-69-8 ]
[ 5162-03-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With dichloro bis(acetonitrile) palladium(II); cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 80℃; under 760.051 Torr; for 6h;	General procedure: A mixture of aryl silane (0.5 mmol), aryl iodines (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 80oC for 6 h in NMP (5 mL) under CO (1atm). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product (ethyl acetate/hexane).

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 2017 - 2020

62
[ 615-41-8 ]
[ 71-43-2 ]
[ 92-52-4 ]
[ 2051-60-7 ]
[ 84-15-1 ]
[ 2113-51-1 ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 12% 3: 9% 4: 21 %Chromat.	With 6,13,14,21-tetraphenyl-22H-tribenzo[b,g,m]-[14]triphyrin(2.1.1); potassium hydroxide; <i>tert</i>-butyl alcohol at 180℃; for 24h; Darkness;	C-H arylation of benzene with 2-chloroiodobenzene by 1 mol% H(trip), 5 equivalents of KOH, at 180 °C. H(trip) (1.6 mg, 0.0023 mmol), 2-chloroiodobenzene (0.027 mL, 0.22 mmol), KOH (66.1 mg, 1.2 mmol), tBuOH(0.22 mL, 2.3 mmol) were added in benzene (2.0 mL, 23 mmol). The mixture was heated at 180 °C under air for 1 day. After thin layer chromatography analysis ofreaction mixture to confirm complete consumption of 2-chloroiodobenzene, 0.1 mL reaction mixture was purified by column chromatography on silica gel by eluting with 8 mL hexane. 1.0 mg naphthalene (internal standard) was added to the solution after chromatography and the mixture was subjected to GC-MS analysis. 2-chlorobiphenyl,2-iodobiphenyl, biphenyl (21%), chlorobenzene (trace), iodobenzene (trace) and o-terphenyl were obtained according to GC-MS. Then the excess benzene was removed under reduced pressure at room temperature. The crude residue was purified by column chromatography eluting with hexane to afford the 2-chlorobiphenyl3 (2i)(4.9 mg, 0.026 mmol, 12%), 2-iodobiphenyl5 (2k) (5.5 mg, 0.020 mmol, 9%) ando-terphenyl (4) (30.4 mg, 0.13 mmol, 60%). 2-chlorobiphenyl (2i) 1H NMR (400MHz, CDCl3) δ 7.73 (m, 1 H), 7.65 (m, 1 H).7.44-7.21(m, 6 H), 7.21-7.19(m, 1 H).2-iodobiphenyl (2k) 1H NMR (400 MHz, CDCl3) δ 7.96 (d, J = 7.9 Hz, 1 H), 7.45 -7.30 (m, 7 H), 7.06-7.02(m, 1 H).

Reference： [1]Xue, Zhao-Li; Qian, Ying Ying; Chan, Kin Shing [Tetrahedron Letters, 2014, vol. 55, # 45, p. 6180 - 6183]

63
[ 201230-82-2 ]
[ 615-41-8 ]
[ 118-91-2 ]

Yield	Reaction Conditions	Operation in experiment
90%	With water; palladium diacetate; triethylamine; triphenylphosphine; In 1,4-dioxane; at 110℃; under 11251.1 Torr; for 2h;Flow reactor;	General procedure: For a typical reaction, a Vapourtec 2R+ Series was used as the platform with a Vapourtec Gas/Liquid Membrane Reactor to load the carbon monoxide. The HPLC pump were both set at 0.125 mL/min, temperature of the reactor at 110 C, pressure of CO at 15 bar with a back pressure regulator of 250 psi (17.24 bar). The system was left running for 2 h to reach steady state after which time the flow streams were switched to pass from the loops where the substrates and catalysts were loaded. The first loop (5 mL) was filled with a solution of palladium acetate (20 mg, 0.08 mmol), triphenylphosphine (48 mg, 0.168 mmol) in 6 mL of 1,4-dioxane while the second loop (5 mL) was filled with a solution made from the ortho-substituted iodoarene substrate (1.68 mmol), triethylamine (0.272 g, 0.374 mL, 2.69 mmol) and water (0.505 g, 28 mmol) in 5.8 mL of 1,4-dioxane. An Omnifit column filled with 1.71 cm3 (r = 0.33 cm, h = 5.00 cm) of cotton was positioned just before the back pressure regulator to trap any particulate matter formed to avoid blocking of the back pressure regulator. After the substrates were passed through the system, the outlet of the flow stream was directed into a receptacle where the excess carbon monoxide gas was vented off in the fume cupboard. The reaction mixture was then evaporated to dryness, ethyl acetate (25 mL) and sodium carbonate solution (2 M, 10 mL) were added and transferred to a separating funnel. After collecting the aqueous layer, the organic layer was extracted with sodium carbonate solution (2 M, 2 × 10 mL). The combined aqueous layers were acidified by the addition of 2 M HCl solution which was then extracted with ethyl acetate (3 x 25 mL). The organic layer was dried over sodium sulfate, and the solvent evaporated under vacuum to give the crude product as a solid. The crude product was then recrystallised from the appropriate solvent.
74%	With water; potassium carbonate; In acetonitrile; at 100℃; under 3750.38 Torr; for 0.0161111h;	General procedure: A 25 mM solution of iodobenzene (5a) and K2CO3 (2 equiv) in H2O/CH3CN (2:1) was pumped at a flow rate of 1.0 mL/min(contact time: 58 s) through a Phoenix flow reactor systemequipped with two cartridges of 4 (total 500 mg; 0.084 mmolPd). Flow hydroxycarbonylation with CO gas introduced from agas module (10 mL/min) was conducted at 100 C and a systempressure of 5 bar. The resulting solution was collected for 50min (50 mL) and the solvent was removed by evaporation. 2 Naq HCl (10 mL) was added and the resulting solid was collectedby filtration, washed with H2O (3 × 10 mL), and dried undervacuum to give benzoic acid (9a) as a white solid without anyfurther purification.Yield: 125 mg (82%); mp 122 C; 1H NMR(400 MHz, DMSO-d6): delta = 12.96 (br s, 1 H, COOH), 7.93 (d, J = 7.2Hz, 2 H, PhH-2 and PhH-6), 7.62 (t, J = 7.2 Hz, 1 H, PhH-4), 7.49 (t, J =7.2 Hz, 2 H, PhH-3 and PhH-5); 13C NMR (101 MHz, DMSO-d6): delta = 167.32 (COOH), 132.87 (Ph), 130.76 (Ph), 129.26 (Ph),128.57 (Ph); ESI-TOF-MS (neg.): m/z = 121 [M - H]-.

Reference： [1]Beilstein Journal of Organic Chemistry,2016,vol. 12,p. 1503 - 1511
[2]Applied Organometallic Chemistry,2018,vol. 32
[3]Synlett,2019,vol. 30,p. 961 - 966

64
[ 615-41-8 ]
[ 872-35-5 ]
2-((2-chlorophenyl)thio)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; copper; In dimethyl sulfoxide; at 100℃; for 24h;	General procedure: A mixture of Cu0 powder (Sigma-Aldrich, <425mum, 99.5% trace metals basis, 0.095mg, 0.015mmol, 3-mol%), anhydrous K3PO4 (0.75mmol), <strong>[872-35-5]2-mercaptoimidazole</strong>/sulfur-containing azoles (0.5mmol), DMSO (0.2mL) and aryl halide (0.75mmol) were added to a reaction vial and a screw cap was fitted to it. The reaction mixture was stirred under air in a closed system at 100C for 24h. The heterogeneous mixture was subsequently cooled to room temperature and diluted with 4.0mL dichloromethane. The combined organic extracts were dried with anhydrous Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was loaded onto the column using minimal amounts of dichloromethane and was purified by silica-gel column chromatography to afford the S-arylated product. The identity and purity of products was confirmed by 1H and 13C NMR spectroscopic analys.

Reference： [1]Tetrahedron,2016,vol. 72,p. 6646 - 6653

65
[ 615-41-8 ]
[ 73183-34-3 ]
[ 870195-94-1 ]

Yield	Reaction Conditions	Operation in experiment
32%	With pyridine; cesium fluoride; In dimethyl sulfoxide; at 105℃; for 2h;Inert atmosphere; Schlenk technique;	General procedure: An oven-dried Schlenk tube, containing a Teflon-coated magnetic stir bar was charged with CsF (228 mg, 1.5 mmol, 3 equiv) and bispinacolatodiboron (254 mg, 1 mmol, 2 equiv). Under an argon atmosphere, freshly distilled DMSO (0.4 mL), the appropriate aryl iodide (0.5mmol), and pyridine (0.4 to 1 equiv) were added successively. The reaction mixture was heated to 105 C and stirred for 2 h under argon.

Reference： [1]Organic Letters,2016,vol. 18,p. 5248 - 5251
[2]Synthesis,2017,vol. 49,p. 4759 - 4768

66
[ 615-41-8 ]
cyclohexyloxy(iodomethyl)dimethylsilane [ No CAS ]
[ 628692-15-9 ]
C₂₀H₂₇ClN₂O₂Si [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 13999 - 14002

67
[ 615-41-8 ]
[ 797755-11-4 ]
[ 39802-80-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80℃; for 2h; Inert atmosphere; Sealed tube;	21 5.1.19. 3-(2'-chloro-[1,1'-biphenyl]-4-yl)propanoic acid (21) General procedure: A solution of boronate 20 (0.16 g, 0.58 mmol) and 1-chloro-2-iodobenzene (0.14 g, 0.59 mmol) in dioxane (2.4 ml) was degassed by bubbling argon through the mixture for 15 min, then 2 M K2CO3(0.87 ml, 1.74 mmol) and Pd(dppf)Cl2 (21 mg, 0.03 mmol) under argon atmosphere were added. The reaction flask was sealed and stirred for 2 h at 80 C. The mixture was cooled to rt, diluted with saturated NH4Cl solution, extracted with EtOAc, and the organic phase was dried over Na2SO4. The extract was concentrated and the residue was purified by column chromatography on silica gel(MeOH in DCM, 1:20) to give the product 21 (0.14 g, 91%) as a white solid. 1H NMR (300 MHz, CDCl3) d: 10.70 (b s, 1H), 7.53-7.23 (m, 8H), 3.03 (t, J = 7.8 Hz, 2H), 2.76 (t, J = 7.8 Hz, 2H). LCMS(ESI) m/z: 259.04 [M+H]+.

Reference： [1]Bobileva, Olga; Ikaunieks, Martins; Duburs, Gunars; Mandrika, Ilona; Petrovska, Ramona; Klovins, Janis; Loza, Einars [Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 16, p. 4314 - 4329]

68
[ 137-26-8 ]
[ 615-41-8 ]
[ 16906-71-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; copper dichloride; zinc; In dimethyl sulfoxide; at 110℃; for 18h;Sealed tube;	General procedure: CuCl2 (1.4 mg, 0.01 mmol), zinc (powder) (26 mg, 0.4 mmol), DMSO (2.0 mL), K2CO3 (41.4 mg, 0.3 mmol), tetramethylthiuram disulfide (2a, 144 mg, 0.6 mmol), and iodobenzene (1a, 204 mg, 1 mmol) were added to a sealed tube equipped with a septum and magnetic stirring bar, the mixture was stirred at 110 C and monitored (TLC) until consumption of the starting material (about 18 h). The mixture was cooled to r.t., quenched with sat. NH4Cl solution and then extracted with EtOAc. The crude solution was dried (anhyd Na2SO4) and evaporated under vacuum. The residue was purified by flash column chromatography (silica gel, PE/EtOAc 5:1) to give 3a (185 mg, 94%) as a white solid;
65%	With copper acetylacetonate; tetrabutylammomium bromide; sodium carbonate; In water; at 100℃; for 12h;Sealed tube;	General procedure: Aryl iodides (1.0 mmol), tetraalkylthiuram disulfides (1.0 mmol), Cu(acac)2 (0.1mmol), Na2CO3 (1.0 mmol), n-Bu4NBr (0.1 mmol) and H2O (2.0 mL) were taken in a25-ml sealed tube. The reaction mixture was stirred at 100 C for 12 hours. Aftercooling to room temperature, the product was diluted with H2O (5 mL) and extractedwith EtOAc (3×10 mL). The extracts were combined and washed by brine (3×10 mL),dried over MgSO4, filtered, and evaporated, and purified by chromatography on silicagel to obtain the desired products with ethyl acetate/hexane (v/v=1:3 1:10). Theproducts were characterized by their spectral and analytical data and compared withthose of the known compounds.

Reference： [1]Synthesis,2018,vol. 50,p. 1527 - 1534
[2]Organic Letters,2017,vol. 19,p. 5916 - 5919
[3]Synlett,2019,vol. 30,p. 610 - 614

69
[ 3054-95-3 ]
[ 615-41-8 ]
[ 1794-45-2 ]

Reference： [1]European Journal of Medicinal Chemistry,2018,vol. 145,p. 235 - 251

70
[ 201230-82-2 ]
[ 615-41-8 ]
[ 71-43-2 ]
[ 5162-03-8 ]

Yield	Reaction Conditions	Operation in experiment
79%	With bis(eta3-allyl-mu-chloropalladium(II)); silver trifluoromethanesulfonate; In 1,2-dichloro-ethane; at 100℃; under 3040.2 Torr; for 24h;Inert atmosphere; Sealed tube; Glovebox; Schlenk technique; Green chemistry;	General procedure: Under an inert nitrogen atmosphere, silver triflate (386 mg,1.5 mmol) was transferred to a Teflon sealed thick-walled 50 ml glass reaction vessel equipped with a stir bar, followed by aryl iodide (1.0 mmol), arene (2.0 mmol), DCE (4 ml) and then a freshly prepared stock solution of [Pd(allyl)Cl]2 (0.2 mg, 5 × 10-4 mmol). The vessel was closed, removed from the glovebox, evacuated and backfilled with carbon monoxide three times, and finally pressurized with 4 atm carbon monoxide. After heating at 100 C for 24 h with stirring, the reaction was cooled to room temperature and carbon monoxide was released. The reaction mixture was filtered through Celite, eluting with dichloromethane. Saturated NaHCO3 was added and the aqueous layer was extracted with dichloromethane. The combined organic layers were concentrated in vacuo and the residue was purified by column chromatography (silica gel, gradient hexane/ethyl acetate 0 to 20%) to afford the pure ketone product.

Reference： [1]Nature Chemistry,2018,vol. 10,p. 193 - 199

71
[ 824-75-9 ]
[ 615-41-8 ]
[ 838-55-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; N,N`-dimethylethylenediamine; In toluene; at 110℃; for 48h;Schlenk technique; Inert atmosphere;	General procedure: An oven-dried Schlenk tube was charged with benzamide 1 (0.5 mmol), K2CO3 (207 mg, 1.5 mmol) and aryl iodide 2 (1.0 mol). The tube was evacuated and backfilled with N2 (3 ×), and then DMEDA (0.2 mmol) and anhyd toluene (5.0 mL) were added. The reaction mixture was stirred at 110 C for 48 h. H2O was added and the crude product was extracted with EtOAc. The combined organic phases were washed with brine and H2O, dried (Na2SO4), and concentrated under reduced pressure. The product was purified by silica gel chromatographyto give the desired N-arylated benzamides (Table 2).

Reference： [1]Synthesis,2018,vol. 50,p. 1090 - 1096

72
[ 615-41-8 ]
[ 870195-94-1 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1842 - 1851

73
[ 615-41-8 ]
[ 269410-07-3 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 1842 - 1851

74
[ 615-41-8 ]
[ 829-85-6 ]
[ 35035-62-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium acetate In N,N-dimethyl acetamide at 130℃; for 3h; Schlenk technique; Inert atmosphere;	17 2.3. General procedure for C-P coupling reaction of various aryliodides with diphenylphosphine General procedure: MCM-41-3N-Pd(0) (21mg, 0.01mmol), KOAc (1.5mmol) and aryl iodide 1 (1.0mmol) (if solid) were placed in an oven-dried 20mL Schlenk tube, the reaction vessel was evacuated and filled with argon for three times. Then aryl iodide 1 (1.0mmol) (if liquid), diphenylphosphine (1.2mmol) and DMAc (1mL) were added with a syringe under a counter flow of argon. The reaction mixture was stirred at 130°C for 3h. After completion of the reaction, the mixture was cooled to room temperature and diluted with CH2Cl2 (20mL) and filtered. The MCM-41-3N-Pd(0) catalyst was washed with distilled water (2×5mL) and ethanol (2×5mL), and reused in the next run. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel to provide the product 2.
75%	With caesium carbonate In toluene at 115℃; for 24h; Inert atmosphere;

Reference： [1]Xu, Zhaotao; Wang, Pingping; Chen, Qiurong; Cai, Mingzhong [Journal of Organometallic Chemistry, 2018, vol. 866, p. 50 - 58]
[2]Fang, Zhiqiang; Cai, Mingzhong; Lin, Yang; Zhao, Hong [Applied Organometallic Chemistry, 2018, vol. 32, # 8]

75
[ 680596-79-6 ]
[ 615-41-8 ]
8-(2-chlorophenyl)-1,4-dioxaspiro[4.5]dec-7-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; at 90℃;	To a solution of 1-chloro-2-iodobenzene (13.4 g, 56 mmoL) in 1, 4-dioxane (200 mL) was added 4, 4, 5, 5-tetramethyl-2- (1, 4-dioxaspiro [4.5] dec-7-en-8-yl) -1, 3, 2-dioxaborolane (15 g, 56 mmol), Pd (dppf) 2Cl2 (4.1 g, 5.6 mmol) and Cs2CO3 (27.6 g, 85 mmol) and the mixture was heated at 90 overnight. After evaporated the solvent under reduced pressure, the residue was added with water (100 mL), extracted with ethyl acetate (100 mL). The organic layer was dried, concentrated and purified by column chromatography (PE: EA=100: 1) to give product as an oil (10.3 g in 73% yield). 1H NMR (CDCl3) deltaH 7.35-7.33 (m, 1H), 7.21-7.16 (m, 3H), 5.59-5.57 (m, 1H), 4.05-4.01 (m, 4H), 2.57-2.54 (m, 2H), 2.46-2.45 (m, 2H), 1.91 (t, J =4.0 Hz, 2H). [M+H] +=251.1.

Reference： [1]Patent: WO2018/54365,2018,A1 .Location in patent: Paragraph 0564; 0565

76
[ 18599-22-9 ]
[ 615-41-8 ]
4-(2-chlorophenyl)-3,3,4,4-tetrafluorobut-1-ene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%		General procedure: In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, were added iodobenzene (3a, 0.40 mL, 3.6 mmol) and Cu2O (0.027 g, 0.18 mmol), and a DMF solution of 2-Zn (0.60 M, 1.0 mL, 0.6 mmol). The whole was heated up at 100 C and stirred at that temperature for 24 h. After cooling to room temperature, the resultant was filtered through a short pad of silica gel using hexane as an eluent. The filtrate was concentrated in vacuo to give the crude materials, which was purified by silica gel column chromatography using hexanes as an eluent, leading to the corresponding compound 4a (0.036 g, 0.17 mmol) in 29% isolated yield as a colorless oil.

Reference： [1]Beilstein Journal of Organic Chemistry,2018,vol. 14,p. 2375 - 2383

77
[ 775351-57-0 ]
[ 615-41-8 ]
[ 1093965-11-7 ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 9513 - 9533

78
[ 7150-72-3 ]
[ 615-41-8 ]
[ 928628-26-6 ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 4147 - 4153

79
[ 1912-45-4 ]
[ 615-41-8 ]
2-(5-chloro-1-(2-chlorophenyl)-1H-indol-3-yl)acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(I) oxide; potassium phosphate In N,N-dimethyl-formamide at 130℃; for 16h; Sealed tube;	Synthesis of 2-(5-chloro-l -(2-chlorophenyl)-l H-indol-3-yl)acetic acid (Intermediate for A43) To 5-chloroindole-3-acetic acid (0.1 g, 0.478 mmol) in DMF (0.5 mL) was added Cu20 (0.478 mmol, 6.8 mg), 17.6 mg), K3PO4 (0.956 mmol, 101 mg) and 1 -chloro-2- iodobenzene (0.718 mmol, 170.6 mg). The mixture was sealed and heated to 130 °C. After stirring for 16 h the reaction was complete. The mixture was filtered and carried forward without further purification. LCMS for C16H11CINO2 calculated 320 [M+H+]; found 320.

Reference： [1]Current Patent Assignee: UNIVERSITY OF CALIFORNIA; KEZAR LIFE SCIENCES - WO2019/46668, 2019, A1 Location in patent: Paragraph 00184

80
[ 615-41-8 ]
tert-butyl 4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate [ No CAS ]
[ 864830-05-7 ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In N,N-dimethyl-formamide at 110℃;	A solution of 1 -chloro-2-iodobenzene (5.0 g, 21.1 mmol) in DMF (150 ml.) was degassed and then filled with argon tert- Butyl 4-(4,4,5,5-tetramethyl- 1 ,3-dioxolan-2-yl)-5,6- dihydropyridine-1 (2/-/)-carboxylate (7.13 g, 23.0 mmol), Pd(dppf)CI2 (1.7 g, 2.1 mmol) and potassium carbonate (8.69 g, 63.0 mmol) were added. The reaction mixture was stirred overnight at 1 10°C and then cooled to ambient temperature. The mixture was poured into water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous Na2S04 and concentrated under reduced pressure. Purification by flash column chromatography on silica gel (ethyl acetate/hexanes = 1 :9 to 1 :4) provided tert- Butyl 4-(2-chlorophenyl)-5,6-dihydropyridine-1 (2/-/)-carboxylate. 1 H NMR (400 MHz, CDCI3): d 7.37 (m, 1 H), 7.18 (m, 3H), 5.67 (m, 1 H), 4.06 (m, 2H), 3.64 (m, 2H), 2.46 (br s, 2H), 1 .51 (s, 9H).

Reference： [1]Current Patent Assignee: KEZAR LIFE SCIENCES - WO2019/178510, 2019, A1 Location in patent: Paragraph 00175

81
[ 615-41-8 ]
[ 100129-35-9 ]

Reference： [1]Patent: WO2019/178510,2019,A1

82
[ 381-98-6 ]
[ 615-41-8 ]
(E)-3-(2-chlorophenyl)-2-(trifluoromethyl)acrylic acid [ No CAS ]
(Z)-3-(2-chlorophenyl)-2-(trifluoromethyl)acrylic acid [ No CAS ]

Reference： [1]Advanced synthesis and catalysis,2020,vol. 362,p. 949 - 954

83
[ 272-24-2 ]
[ 615-41-8 ]
6-(2-chlorophenyl)thieno[2,3-d]pyrimidine [ No CAS ]

Reference： [1]Organic Letters,2020,vol. 22,p. 1547 - 1551

84
[ 624-92-0 ]
[ 615-41-8 ]
[ 17733-22-1 ]

Yield	Reaction Conditions	Operation in experiment
48%	With tetrabutylammomium bromide; copper(II) acetate monohydrate; potassium hydroxide In water at 100℃; for 12h; Sealed tube;	(Het)aryl Methyl Sulfides; General Procedure General procedure: A 25-mL sealable tube was charged with the appropriate aryliodide or bromide (1.0 mmol), dimethyl disulfide (1.2 mmol),Cu(OAc)2·H2O (0.1 mmol), KOH (2.0 mmol), TBAB (0.05 mmol),and H2O (2.0 mL). The mixture was stirred at 100 °C (130 °C forbromides) for 12 h under air then cooled to r.t. The mixture wasdiluted with H2O (5 mL) and extracted with EtOAc (4 × 10 mL).The extracts were combined, washed with brine (3 × 10 mL),dried (MgSO4), filtered, and concentrated. The residue was purifiedby chromatography [silica gel, EtOAc-hexane (1:30 to1:100)].

Reference： [1]Wang, Ying-Yu; Wu, Xiang-Mei; Yang, Ming-Hua [Synlett, 2020]

85
[ 16807-11-7 ]
[ 615-41-8 ]
bromo-6-chloro-phenyl-9H-carbazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With copper(l) iodide; sodium carbonate In N,N-dimethyl-formamide at 120℃; for 4h;	5 Synthesis intermediate (Au-053-a): Put 1-chloro-2-iodobenzene (26.64g, 1.1eq), 1-bromocarbazole (25g, 1eq), sodium tert-butoxide (48.81g, 5eq) and a small amount of cuprous iodide into a single-necked bottle, add 250 mL of DMF was reacted at 120°C for 4 hours.After the reaction solution was evaporated to dryness in a vacuum, it was washed with dichloromethane, and then the solid that could not be completely dissolved was filtered out.The filtrate was spin-dried, and the silica gel column was used for separation and purification to obtain a white solid intermediate (Au-053-a) with a yield of 92%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112940016, 2021, A Location in patent: Paragraph 0254-0256

86
[ 615-41-8 ]
[ 26088-68-6 ]
9-(2-chlorophenyl)-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.8%	With copper(l) iodide; N,N`-dimethylethylenediamine In toluene at 130℃; Inert atmosphere;	20.2 Step 2: Preparation of 9-(2-chlorophenyl)-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid ethyl ester Dissolve (200mg, 0.823mmol) and 1-chloro-2-iodobenzene (235mg, 0.988mmol) in toluene (6mL), add cuprous iodide (15.6mg, 0.0823mmol), potassium phosphate (349mg, 1.65mmol) ) And dimethylethylenediamine (14.5mg, 0.165mmol). The reaction mixture was stirred overnight at 130°C under the protection of argon. After the reaction solution was cooled to room temperature, water (10 mL) was added, and the mixture was extracted with ethyl acetate (10 mL×2). The combined organic phase was washed with brine (10 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain a crude product. After separation and purification by column chromatography (silica gel, petroleum ether: ethyl acetate = 10:1), the target compound (200 mg, yield 68.8%, white solid) was obtained.

Reference： [1]Current Patent Assignee: SHANGHAI HUIQI BIOMEDICAL TECH; FUKANG SHANGHAI HEALTH TECH - CN113121527, 2021, A Location in patent: Paragraph 0280; 0284-0285

87
[ 615-41-8 ]
[ 626-40-4 ]
C₁₈H₁₁Br₂Cl₂N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; sodium butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene for 6h; Reflux;	1 1. Synthesis of Compound A-1 A toluene (400 mL) solution of 3,5-dibromoaniline (20 g), 1-chloro-2-iodobenzene (57 g), sodium butoxide (23 g), Pd2(dba)3 (1.5 g), and PH(tBu)3/BF4 (1.8 g) was heated to reflux for 6 hours using oil bath heating. After cooling to room temperature, the reaction solution was poured into water. The target product was extracted with ethyl acetate, dried over magnesium sulfate, and then concentrated under reduced pressure. The resulting mixture was purified by silica gel chromatography to obtain Intermediate 1 (13.5 g, yield: 36%).

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2021/202861, 2021, A1 Location in patent: Paragraph 0156; 0157

88
[ 615-41-8 ]
[ 2210-24-4 ]
C₁₅H₁₄ClNOSe [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93.4%	Stage #1: 2-iodochlorobenzene With selenium powder; magnesium In tetrahydrofuran for 1h; Milling; Stage #2: N-acryloylaniline In tetrahydrofuran Milling;	11-12 Example 11 Magnesium bars (5eq., 1.0mmol, 24mg), selenium powder (5eq., 1.0mmol, 79mg), 1-chloro-2-iodobenzene (7.5eq., 1.5mmol, 185uL) were added to a stainless steel jar (10mL) ), the diameter of the ball milling medium is 10mm, add 1ml of THF, tighten the stainless steel pot, and place it on a ball mill for grinding (Retsch MM 400, 60min, 30Hz); After grinding for 60 min, the stainless steel jar was opened in the air, N-phenylacrylamide (1 eq., 0.2 mmol, 29.4 mg) was added, the stainless steel jar was tightened, and the jar was placed on a ball mill for grinding (Retsch MM 400, 15 min, 5 Hz) , After grinding, the mixture was eluted from silica gel with EA, and the solvent was evaporated under reduced pressure to remove the solvent, and 63.4 mg of pure product was obtained by flash column chromatography (SiO2, petroleum ether/ethyl acetate, 5:1-10:1). Yield 93.4%. (method 1)

Reference： [1]Current Patent Assignee: UNIV XI AN JIAOTONG - CN114213300, 2022, A Location in patent: Paragraph 0076-0082

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. 615-41-8 ] {[proInfo.proName]}

Quality Control of [ 615-41-8 ]

Related Doc. of [ 615-41-8 ]

Product Details of [ 615-41-8 ]

Calculated chemistry of [ 615-41-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 615-41-8 ]

Application In Synthesis of [ 615-41-8 ]

[ 615-41-8 ] Synthesis Path-Upstream 1~10

[ 615-41-8 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry