[ CAS No. 608-28-6 ] {[proInfo.proName]}

Name: 608-28-6|2-Iodo-1,3-dimethylbenzene|98%
Brand: Ambeed
SKU: A197260
Price: 7.0 USD
Availability: InStock
Rating: 98 (27 reviews)

,{[proInfo.pro_purity]}

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

2D 3D

Structure of 608-28-6 * 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 [ 608-28-6 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 608-28-6 ]

SDS Specification

Alternatived Products of [ 608-28-6 ]

Product Details of [ 608-28-6 ]

CAS No. :	608-28-6	MDL No. :	MFCD00019012
Formula :	C₈H₉I	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QTUGGVBKWIYQSS-UHFFFAOYSA-N
M.W :	232.06	Pubchem ID :	69097
Synonyms :

Calculated chemistry of [ 608-28-6 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.25
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.09
TPSA :	0.0 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.36
Log Po/w (XLOGP3) :	3.95
Log Po/w (WLOGP) :	2.91
Log Po/w (MLOGP) :	3.83
Log Po/w (SILICOS-IT) :	3.74
Consensus Log Po/w :	3.36

Druglikeness

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

Water Solubility

Log S (ESOL) :	-4.26
Solubility :	0.0127 mg/ml ; 0.0000549 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.65
Solubility :	0.0519 mg/ml ; 0.000224 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.13
Solubility :	0.0172 mg/ml ; 0.0000743 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.61

Safety of [ 608-28-6 ]

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

Application In Synthesis of [ 608-28-6 ]

* 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 [ 608-28-6 ]
Downstream synthetic route of [ 608-28-6 ]

[ 608-28-6 ] Synthesis Path-Upstream 1~16

1
[ 608-28-6 ]
[ 443-88-9 ]

Reference： [1] Journal of the American Chemical Society, 2012, vol. 134, # 26, p. 10795 - 10798

2
[ 100379-00-8 ]
[ 608-28-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iodine; potassium carbonate In acetonitrile at 80℃; for 12 h; Inert atmosphere; Schlenk technique; Sealed tube	General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 °Cfor 8–12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a–v

Reference： [1] Synlett, 2014, vol. 25, # 7, p. 995 - 1000

3
[ 87-62-7 ]
[ 608-28-6 ]

Reference： [1] Journal of the American Chemical Society, 1949, vol. 71, p. 1362,1366
[2] Monatshefte fuer Chemie, 1934, vol. 64, p. 361,364, 365[3] Monatshefte fuer Chemie, 1935, vol. 65, p. 6,14
[4] Journal fuer Praktische Chemie (Leipzig), 1900, vol. <2> 61, p. 322
[5] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 6, p. 1679 - 1685
[6] European Journal of Organic Chemistry, 2000, # 14, p. 2663 - 2668
[7] Canadian Journal of Chemistry, 2005, vol. 83, # 3, p. 213 - 219

4
[ 632-46-2 ]
[ 608-28-6 ]

Reference： [1] Journal of the American Chemical Society, 2017, vol. 139, # 33, p. 11527 - 11536

5
[ 82113-65-3 ]
[ 87-62-7 ]
[ 608-28-6 ]

Reference： [1] Heteroatom Chemistry, 2018, vol. 29, # 2,

6
[ 576-22-7 ]
[ 608-28-6 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2001, vol. 11, # 3, p. 327 - 329

7
[ 108-38-3 ]
[ 4214-28-2 ]
[ 608-28-6 ]

Reference： [1] Journal of Organic Chemistry, 1993, vol. 58, # 8, p. 2058 - 2060
[2] Organic Process Research and Development, 2008, vol. 12, # 6, p. 1130 - 1136

8
[ 19230-28-5 ]
[ 21450-64-6 ]
[ 608-28-6 ]
[ 83909-08-4 ]

Reference： [1] Journal of Organic Chemistry, 1990, vol. 55, # 3, p. 881 - 890

9
[ 4102-48-1 ]
[ 108-95-2 ]
[ 608-28-6 ]
[ 1227681-30-2 ]
[ 22445-41-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 12, p. 2185 - 2189

10
[ 116599-63-4 ]
[ 64-19-7 ]
[ 608-28-6 ]
[ 7782-50-5 ]

Reference： [1] Journal of the American Chemical Society, 1959, vol. 81, p. 2374,2376

11
[ 4102-48-1 ]
[ 108-95-2 ]
[ 608-28-6 ]
[ 1227681-30-2 ]
[ 22445-41-6 ]

Reference： [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 12, p. 2185 - 2189

12
[ 608-28-6 ]
[ 2142-76-9 ]

Reference： [1] Journal of the American Chemical Society, 1954, vol. 76, p. 781,783

13
[ 608-28-6 ]
[ 5402-60-8 ]

Reference： [1] Journal of the American Chemical Society, 1960, vol. 82, p. 1349 - 1352

14
[ 608-28-6 ]
[ 124-38-9 ]
[ 62285-58-9 ]

Reference： [1] Journal of the American Chemical Society, 1960, vol. 82, p. 1349 - 1352

15
[ 608-28-6 ]
[ 201230-82-2 ]
[ 62285-58-9 ]
[ 108-38-3 ]
[ 1123-56-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 32, p. 10362 - 10367[2] Angew. Chem., 2018, vol. 130, # 32, p. 10519 - 10524,6

16
[ 608-28-6 ]
[ 87-62-7 ]
[ 74443-35-9 ]

Reference： [1] Journal of the American Chemical Society, 1980, vol. 102, # 8, p. 2773 - 2776

[ 608-28-6 ] Synthesis Path-Downstream 1~88

1
[ 608-28-6 ]
[ 2902-65-0 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium permanganate In water; <i>tert</i>-butyl alcohol at 90℃; for 18h;
	With potassium permanganate

Reference： [1]Yu, Congjun; Patureau, Frederic W. [Angewandte Chemie - International Edition, 2019, vol. 58, # 51, p. 18530 - 18534][Angew. Chem., 2019, # 58, p. 18701 - 18705,5]
[2]Gilman; Stuckwisch [Journal of the American Chemical Society, 1943, vol. 65, p. 1729,1731, 1732]

2
[ 87-62-7 ]
[ 608-28-6 ]

Yield	Reaction Conditions	Operation in experiment
67%		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]Turkish Journal of Chemistry,2020,vol. 44,p. 535 - 542
[2]Journal of the American Chemical Society,1949,vol. 71,p. 1362,1366
[3]Journal fur praktische Chemie (Leipzig 1954),1900,vol. <2> 61,p. 322
[4]Bulletin of the Chemical Society of Japan,1996,vol. 69,p. 1679 - 1685
[5]European Journal of Organic Chemistry,2000,p. 2663 - 2668
[6]Canadian Journal of Chemistry,2005,vol. 83,p. 213 - 219

3
[ 118-72-9 ]
[ 608-28-6 ]
[ 52805-90-0 ]

Reference： [1]Journal of the American Chemical Society,1988,vol. 110,p. 1280
[2]Journal of the Indian Chemical Society,1961,vol. 38,p. 33 - 40

4
[ 608-28-6 ]
[ 108-98-5 ]
[ 54088-93-6 ]

Reference： [1]Tetrahedron Letters,2009,vol. 50,p. 3661 - 3664
[2]Journal of the American Chemical Society,2013,vol. 135,p. 9548 - 9552
[3]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 1385 - 1389
[4]Journal of Organic Chemistry,1974,vol. 39,p. 3173 - 3174

5
[ 608-28-6 ]
[ 87-62-7 ]
[ 74443-35-9 ]

Reference： [1]Journal of the American Chemical Society,1980,vol. 102,p. 2773 - 2776

6
[ 19230-28-5 ]
[ 21450-64-6 ]
[ 608-28-6 ]
[ 83909-08-4 ]

Reference： [1]Journal of Organic Chemistry,1990,vol. 55,p. 881 - 890

7
[ 608-28-6 ]
[ 124-38-9 ]
[ 62285-58-9 ]

Reference： [1]Journal of the American Chemical Society,1960,vol. 82,p. 1349 - 1352

8
[ 608-28-6 ]
copper (I)-cyanide [ No CAS ]
[ 6575-13-9 ]

Reference： [1]Monatshefte fur Chemie,1934,vol. 64,p. 361,364, 365
Monatshefte fuer Chemie,1935,vol. 65,p. 6,14

9
[ 141-32-2 ]
[ 608-28-6 ]
2,6-dimethyl-trans-cinnamic acid n-butyl ester [ No CAS ]

Reference： [1]Organic Letters,2003,vol. 5,p. 3209 - 3212

10
[ 853955-69-8 ]
[ 608-28-6 ]
[ 3976-34-9 ]

Reference： [1]Journal of the American Chemical Society,2005,vol. 127,p. 6952 - 6953

11
[ 608-28-6 ]
[ 958-09-8 ]
N⁶-(2,6-dimethylphenyl)-2'-deoxyadenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium phosphate; copper(l) iodide; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 110℃; for 48h;

Reference： [1]Ran, Chongzhao; Dai, Qing; Harvey, Ronald G. [Journal of Organic Chemistry, 2005, vol. 70, # 9, p. 3724 - 3726]

12
[ 608-28-6 ]
[ 2039-90-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium; diethyl ether / anschliessend Behandeln mit Acetaldehyd 2: activated Al₂O₃ / 270 - 280 °C / 10 Torr

Reference： [1]Schwartzman; Corson [Journal of the American Chemical Society, 1954, vol. 76, p. 781,783]

13
[ 608-28-6 ]
[ 2142-76-9 ]

Reference： [1]Journal of the American Chemical Society,1954,vol. 76,p. 781,783

14
[ 608-28-6 ]
[ 698392-47-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: lithium; diethyl ether / anschliessend Behandeln mit Acetaldehyd 2: activated Al₂O₃ / 270 - 280 °C / 10 Torr 3: KMnO₄; aqueous KOH / Erwaermen des Reaktionsprodukts mit H₂SO₄, Aethanol und Benzol

Reference： [1]Schwartzman; Corson [Journal of the American Chemical Society, 1954, vol. 76, p. 781,783]

15
[ 608-28-6 ]
[ 670-95-1 ]
C₁₇H₁₆N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
39%	With copper; potassium carbonate;18-crown-6 ether; In tetralin; at 180℃; for 68h;	One 250ml flask was charged with 4-phenyl imidazole (7.08g, 49.12mmole), 2-iodo-m- xylene(9.5g, 40.93mmole), copper (5.721g, 90.046mmole); 18-crown-6 (1.081g, 4.09 mmole), K2CO3 (21.49g, 155.53 mmole) and tetrahydronaphthalene (90ml). Reaction was heated to 180 C for 68hrs. Reaction mixture was then filtered through Celite and the filtrate was concentrated to dryness. The residue was subjected to kugelrohr distillation and 4g of ligand was obtained.(39%).
39%	With copper; potassium carbonate;18-crown-6 ether; In tetralin; at 180℃; for 68h;	One 250ml flask was charged with 4-phenyl imidazole (7.08g, 49.12mmole), 2- iodo-m-xylene(9.5g, 40.93mmole), copper (5.721g, 90.046mmole); 18-crown-6 (1.08Ig, 4.09 mmole), K2CO3 (21.49g, 155.53 mmole) and tetrahydronaphthalene (90ml). Reaction was heated to 180 C for 68hrs. Reaction mixture was then filtered through Celite and the filtrate was concentrated to dryness. The residue was subjected to kugelrohr distillation and 4g of ligand was obtained.(39%).

Reference： [1]Patent: WO2008/54584,2008,A1 .Location in patent: Page/Page column 100
[2]Patent: WO2006/121811,2006,A1 .Location in patent: Page/Page column 93

16
2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9-vinyl-9H-purin-6-amine [ No CAS ]
[ 608-28-6 ]
(E)-9-(2,6-dimethylstyryl)-2-chloro-N-(4-(dimethylphosphoryl)phenyl)-9H-purin-6-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine;palladium diacetate; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 110℃;	B) (E)-9-(2,6-dimethylstyryl)-2-chloro-/V-(4-(dimethylphosphoryl)phenyl)-9H-purin-6-amine; To an oven-dried 50 mL round-bottom flask were added 2-chloro-Lambda/-(4-(dimethylphosphoryl)phenyl)- 9-vinyl-9/-/-purin-6-amine (0.32 g, 0.93 mmol ), Pd(OAc)2 (10 mg, 0.05 mmol ), tri-o-tolylphosphine (30 mg, 0.1 mmol ), 2-iodo-m-xylene(0.39 g, 1.67 mmol). The mixture was flushed with Ar and then dissolved in -10 mL anhydrous DMF. DIEA (0.39 g, 2.79 mmol) was then added via syringe. The reaction was stirred at 110 0C overnight. The reaction was diluted with EtOAc and filtered through celite, washed with ample -5 % MeOH/EtOAc, the combined organic layer was washed with water twice, dried over Na2SO4. Final product was purified by silica gel column chromatography (4-8 %MeOH/DCM).

Reference： [1]Patent: WO2007/21937,2007,A2 .Location in patent: Page/Page column 46

17
[ 608-28-6 ]
[ 5720-07-0 ]
4'-methoxy-2,6-dimethyl-biphenyl [ No CAS ]

Reference： [1]Chemical Communications,2006,p. 2495 - 2497
[2]Advanced Synthesis and Catalysis,2011,vol. 353,p. 1889 - 1896

18
[ 6165-69-1 ]
[ 608-28-6 ]
[ 201230-82-2 ]
[ 898771-06-7 ]

Yield	Reaction Conditions	Operation in experiment
64%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate; In chlorobenzene; at 80℃; for 24h;	General procedure: The aryl iodide (1.0 mmol), boronic acid (2.0 mmol), PEPPSI-IPr (0.03 mmol), and Cs2CO3 (3.0 mmol) were placed into a 25 mL round-bottomed flask that was fitted with a reflux condenser. Chlorobenzene (5 mL) was added, and the flask was evacuated and backfilled with CO(g) (three cycles). The mixture was heated to 80 C (oil bath) with stirring for 24 h under a balloon of CO(g). The reaction mixture was filtered through a pad of Celite, washing with EtOAc. The filtrate was washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to afford the desired benzophenone.

Reference： [1]Tetrahedron,2011,vol. 67,p. 4344 - 4351
[2]Organic Letters,2008,vol. 10,p. 5301 - 5304

19
[ 608-28-6 ]
[ 201230-82-2 ]
[ 16419-60-6 ]
[ 14252-17-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate; In 1,4-dioxane; at 140℃; under 3102.97 Torr; for 24h;Pressure reactor;	General procedure: The aryl iodide (1.0 mmol), boronic acid (2.0 mmol), PEPPSI-IPr (0.03 mmol), and Cs2CO3 (2.5 mmol) were placed into a 10 mL glass sleeve fitted with a rubber septum. The sleeve was then evacuated and backfilled with CO(g) three times. Dioxane (5.0 mL) was added, and the mixture was sparged with CO(g) for 2 min. The rubber septum was then removed, and the glass sleeve was quickly sealed in a stainless steel pressure reactor. The reactor was evacuated and backfilled with CO(g) (three cycles, 60 psi). The reactor was heated at 140 C (oil bath) with stirring for 24 h at 60 psi of CO(g). The reaction mixture was filtered through a pad of Celite, washing with EtOAc. The filtrate was washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to afford the product benzophenone.

Reference： [1]Organic Letters,2008,vol. 10,p. 5301 - 5304
[2]Tetrahedron,2011,vol. 67,p. 4344 - 4351

20
[ 608-28-6 ]
[ 201230-82-2 ]
[ 5720-07-0 ]
[ 52629-41-1 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 5301 - 5304
[2]Tetrahedron,2011,vol. 67,p. 4344 - 4351

21
[ 608-28-6 ]
[ 201230-82-2 ]
[ 23112-96-1 ]
[ 1082070-20-9 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate; In chlorobenzene; at 80℃; for 24h;	General procedure: The aryl iodide (1.0 mmol), boronic acid (2.0 mmol), PEPPSI-IPr (0.03 mmol), and Cs2CO3 (3.0 mmol) were placed into a 25 mL round-bottomed flask that was fitted with a reflux condenser. Chlorobenzene (5 mL) was added, and the flask was evacuated and backfilled with CO(g) (three cycles). The mixture was heated to 80 C (oil bath) with stirring for 24 h under a balloon of CO(g). The reaction mixture was filtered through a pad of Celite, washing with EtOAc. The filtrate was washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to afford the desired benzophenone.

Reference： [1]Organic Letters,2008,vol. 10,p. 5301 - 5304
[2]Tetrahedron,2011,vol. 67,p. 4344 - 4351

22
[ 608-28-6 ]
[ 201230-82-2 ]
[ 536-74-3 ]
[ 1082070-24-3 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 5301 - 5304
[2]Tetrahedron,2011,vol. 67,p. 4344 - 4351

23
[ 608-28-6 ]
[ 201230-82-2 ]
[ 768-60-5 ]
[ 1082070-25-4 ]

Reference： [1]Organic Letters,2008,vol. 10,p. 5301 - 5304

24
[ 608-28-6 ]
[ 201230-82-2 ]
[ 98-80-6 ]
[ 1139-60-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate; In 1,4-dioxane; at 140℃; under 3102.97 Torr; for 24h;Pressure reactor;	General procedure: The aryl iodide (1.0 mmol), boronic acid (2.0 mmol), PEPPSI-IPr (0.03 mmol), and Cs2CO3 (2.5 mmol) were placed into a 10 mL glass sleeve fitted with a rubber septum. The sleeve was then evacuated and backfilled with CO(g) three times. Dioxane (5.0 mL) was added, and the mixture was sparged with CO(g) for 2 min. The rubber septum was then removed, and the glass sleeve was quickly sealed in a stainless steel pressure reactor. The reactor was evacuated and backfilled with CO(g) (three cycles, 60 psi). The reactor was heated at 140 C (oil bath) with stirring for 24 h at 60 psi of CO(g). The reaction mixture was filtered through a pad of Celite, washing with EtOAc. The filtrate was washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to afford the product benzophenone.

Reference： [1]Organic Letters,2008,vol. 10,p. 5301 - 5304
[2]Tetrahedron,2011,vol. 67,p. 4344 - 4351

25
[ 608-28-6 ]
[ 536-74-3 ]
[ 180783-48-6 ]

Yield	Reaction Conditions	Operation in experiment
94%	With C20H29Cl2N5O2Pd; potassium carbonate; In ethanol; at 80℃; for 2h;	General procedure: A vial was charged with an aryl halide (0.1 mmol), an aryl or alkylacetylene(0.11 mmol), K2CO3 (0.15 mmol), palladium catalyst (0.05 mol %), and EtOH(2 mL). The mixture was refluxed with stirring for 2 h. After this time, themixture was cooled and CH2Cl2-n-hexane (1:2, 2 mL) and H2O (2 mL) wereadded. The organic layer was separated, filtered through a small amount ofsilica gel and analyzed by GC-MS. The solvent was removed and the residueweighed and analyzed by 1H NMR.
82%	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.
72%	With bis(cyclohexylisocyanide)palladium(II) chloride; potassium carbonate; benzoic acid hydrazide; In ethanol; at 80℃; for 2h;	General procedure: A solution of comple 1 in ethanol with a required concentrationwas added with stirring to a mixture of iodoarene2a-2g (0.3 mmol), phenylacetylene (3, 0.5 mmol),potassium carbonate (0.7 mmol), and ethanol (2 mL). The mixture was heated for 2 h on an oil bath at a bathtemperature of 80C. After cooling to room temperature,the mixture was diluted with 10 mL of waterand extracted with hexane-methylene chloride (5 : 1,2 × 5 mL), and the combined extracts were dried overanhydrous sodium sulfate and analyzed by GC/MS.The solvent was evaporated, and the product wasisolated by silica gel column chromatography usingn-hexane as eluent.The properties of the isolated compounds were inagreement with the data given in [23-27].

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 301 - 305
[2]Synthesis,2013,vol. 45,p. 817 - 829
[3]Tetrahedron Letters,2014,vol. 55,p. 2101 - 2103
[4]Applied Organometallic Chemistry,2016,vol. 30,p. 831 - 834
[5]Journal of Organometallic Chemistry,2018,vol. 860,p. 98 - 105
[6]Chemistry - A European Journal,2013,vol. 19,p. 8144 - 8152
[7]Journal of the American Chemical Society,2009,vol. 131,p. 4917 - 4927
[8]Russian Journal of General Chemistry,2017,vol. 87,p. 1663 - 1666
Zh. Obshch. Khim.,2017,vol. 87,p. 1247 - 1251,5
[9]ACS Catalysis,2019,vol. 9,p. 11640 - 11646
[10]Advanced Synthesis and Catalysis,2009,vol. 351,p. 891 - 902
[11]Chemistry - An Asian Journal,2017,vol. 12,p. 2221 - 2230

26
[ 608-28-6 ]
[ 71759-92-7 ]
[ 1191900-29-4 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium phosphate; C₂₈H₄₇ClN₄P₂Pd In 1,4-dioxane; ethylene glycol at 140℃; for 1h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Bolliger, Jeanne L.; Frech, Christian M. [Advanced Synthesis and Catalysis, 2009, vol. 351, # 6, p. 891 - 902]

27
[ 608-28-6 ]
[ 98-80-6 ]
[ 3976-34-9 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 16346 - 16347
[2]RSC Advances,2016,vol. 6,p. 46864 - 46870
[3]ChemCatChem,2016,vol. 8,p. 1176 - 1184

28
[ 608-28-6 ]
[ 1098106-66-1 ]
[ 1098106-67-2 ]

Yield	Reaction Conditions	Operation in experiment
19%	With triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; at 70℃; for 1.5h;	To a degassed solution of 3-(3-ethynylphenyl)propan-l-ol (11) (0.270 g, 1.7 mmol) and 2-iodo-l,3- dimethylbenzene (0.392 g, 1.7 mmol) in triethylamine (10 mL) was added PdCl2(PPh3)3 (0.036 g, 0.05 mmol) and CuI (0.010 g, 0.05 mmol). The resulting mixture was degassed and stirred under argon at 70 0C for 1.5 h. The reaction mixture was concentrated under reduced pressure and diluted with EtOAc (30 mL). The solution was filtered through filter paper, washed with water (2x20 mL), dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (7 to 60% EtOAc-hexanes gradient) gave (3-((2,6-dimethylphenyl)ethynyl)phenyl)propan-l-ol (12) as a light brown oil. Yield (0.085 g, 19%). This material was taken on to the next synthetic step without further purification

Reference： [1]Patent: WO2009/5794,2009,A2 .Location in patent: Page/Page column 123-124

29
[ 608-28-6 ]
[ 576-26-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(l) iodide; cesium hydroxide; butane-2,3-dione dioxime; In water; dimethyl sulfoxide; at 120℃; for 12h;	General procedure: The appropriate aryl halide (1 mmol), CsOH (3 mmol), andH2O (1 mL) were added over 0.1 h, to a stirred solutionof CuI (19.0 mg, 10 mol%) and Dimethylglyoxime (L6;23.2 mg, 20 mol%) in DMSO (1 mL), and the reactionmixture was stirred at 120 C (aryl iodides) or (aryl bromides).The progress of the reaction was monitored by TLC(EtOAc-hexane). The reaction mixture was then cooled toroom temperature and acidified with 0.5 M HCl (0.5 mL).The resulting mixture was extracted with EtOAc (3×10 mL)and dried (Na2SO4). Evaporation of the solvent gave a residuethat was purified by column chromatography.
76%	With water; ethylene glycol; potassium hydroxide; copper dichloride; In dimethyl sulfoxide; at 120℃; for 24h;Inert atmosphere;	To a test tube containing a magnetic bar was added aryl halide (1.0 mmol), CuCl2 (13.4 mg, 0.1 mmol), KOH (336 mg, 6.0 mmol), ethylene glycol(12 muL, 0.2 mmol), and DMSO/H2O (1.0 mL/0.5 mL). After flushing with argon, the mixture was stirred in a preheated oil bath at 120 C for 24 h. After cooled to ambient temperature, the reaction mixture was distributed in aqueous HCl (5 %) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4, and concentrated under vacuum. The crude product was further purified by column chromatography (EtOAc/n-Hexane) to provide the phenols.
65%	With 2-(N,N-dimethylamino)athanol; potassium hydroxide; silver(l) oxide; In water; dimethyl sulfoxide; at 130℃; for 24h;	To a test tube containing a magnetic rod was added 4-iodotoluene, 1.0 mmol, Cu2O (14.3 mg, 0.1 mmol), KOH (169 mg, 3.0 mmol), 2-dimethylaminoethanol , 0.3 mL, 3.0 mmol) and DMSO / H2O (1.5 mL / 0.5 mL). After flushing with argon, the mixture was stirred at 100 & lt; 0 & gt; C for 24 hours in a preheated oil bath. After cooling to ambient temperature, the reaction mixture was distributed in aqueous HCl (5%) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc / n-Hexane) to give phenol.

Reference： [1]Chemical Communications,2014,vol. 50,p. 9072 - 9075
[2]Synthesis,2010,p. 4268 - 4272
[3]Journal of Organic Chemistry,2013,vol. 78,p. 5804 - 5809
[4]Journal of Chemical Sciences,2018,vol. 130
[5]Bulletin of the Korean Chemical Society,2015,vol. 36,p. 2833 - 2840
[6]Patent: KR2017/91976,2017,A .Location in patent: Paragraph 0058; 0059
[7]European Journal of Organic Chemistry,2014,vol. 2014,p. 315 - 318
[8]European Journal of Organic Chemistry,2014,vol. 2014,p. 315 - 318

30
[ 608-28-6 ]
potassium trimethoxy(trifluoromethyl)boranuide [ No CAS ]
[ 41818-96-6 ]

Yield	Reaction Conditions	Operation in experiment
59%	With copper(l) iodide; 1,10-Phenanthroline In dimethyl sulfoxide at 60℃; for 16h; Inert atmosphere;

Reference： [1]Location in patent: experimental part Knauber, Thomas; Arikan, Fatih; Roeschenthaler, Gerd-Volker; Goossen, Lukas J. [Chemistry - A European Journal, 2011, vol. 17, # 9, p. 2689 - 2697]

31
[ 608-28-6 ]
(1,10-phenanthroline)(trifluoromethyl)copper (I) [ No CAS ]
[ 41818-96-6 ]

Yield	Reaction Conditions	Operation in experiment
87 %Spectr.	In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;

Reference： [1]Morimoto, Hiroyuki; Tsubogo, Tetsu; Litvinas, Nichole D.; Hartwig, John F. [Angewandte Chemie - International Edition, 2011, vol. 50, # 16, p. 3793 - 3798]

32
[ 608-28-6 ]
[ 201230-82-2 ]
[ 1312774-62-1 ]
[ 1082070-23-2 ]

Yield	Reaction Conditions	Operation in experiment
49%	With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride; caesium carbonate; In 1,4-dioxane; at 140℃; under 3102.97 Torr; for 24h;Pressure reactor;	General procedure: The aryl iodide (1.0 mmol), boronic acid (2.0 mmol), PEPPSI-IPr (0.03 mmol), and Cs2CO3 (2.5 mmol) were placed into a 10 mL glass sleeve fitted with a rubber septum. The sleeve was then evacuated and backfilled with CO(g) three times. Dioxane (5.0 mL) was added, and the mixture was sparged with CO(g) for 2 min. The rubber septum was then removed, and the glass sleeve was quickly sealed in a stainless steel pressure reactor. The reactor was evacuated and backfilled with CO(g) (three cycles, 60 psi). The reactor was heated at 140 C (oil bath) with stirring for 24 h at 60 psi of CO(g). The reaction mixture was filtered through a pad of Celite, washing with EtOAc. The filtrate was washed with H2O (20 mL), brine (20 mL), dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to afford the product benzophenone.

Reference： [1]Tetrahedron,2011,vol. 67,p. 4344 - 4351

33
[ 608-28-6 ]
[ 201230-82-2 ]
[ 33675-41-1 ]
[ 1082070-25-4 ]

Yield	Reaction Conditions	Operation in experiment
75%		General procedure: n-BuLi (0.63 mmol, 2.12 M solution in hexanes) was added dropwise to a solution of the alkyne (0.60 mmol) in THF (1.0 mL) at -78 C. The resultant solution was stirred for 30 min, whereupon a solution of ZnBr2 (0.63 mmol) in THF (0.65 mL) was added. The cooling bath was removed, and the solution was warmed to ambient temperature. The aryl iodide (0.30 mmol), PEPPSI-IPr (0.009 mmol), and LiBr (0.90 mmol) were placed into a dry, 10 mL glass sleeve. The sleeve was placed into the metal jacket of the stainless steel pressure reactor, fitted with a rubber septum, and placed under nitrogen. NMP (2 mL) was added, and the mixture was cooled to -78 C, whereupon the previously prepared zinc acetylide solution (2 mL, 0.3 M) was added dropwise. The jacket was removed from the bath, and the pressure reactor was sealed. The reactor was evacuated and backfilled with CO(g) (three cycles, 60 psi). The reactor was heated to 80 C (oil bath) with stirring for 24 h at 60 psi of CO(g). The reaction mixture was diluted with CH2Cl2 (20 mL) and brine (20 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organics were dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to deliver the desired ketone.

Reference： [1]Tetrahedron,2011,vol. 67,p. 4344 - 4351

34
[ 608-28-6 ]
[ 201230-82-2 ]
[ 932-87-6 ]
[ 1082070-24-3 ]

Yield	Reaction Conditions	Operation in experiment
79%		General procedure: n-BuLi (0.63 mmol, 2.12 M solution in hexanes) was added dropwise to a solution of the alkyne (0.60 mmol) in THF (1.0 mL) at -78 C. The resultant solution was stirred for 30 min, whereupon a solution of ZnBr2 (0.63 mmol) in THF (0.65 mL) was added. The cooling bath was removed, and the solution was warmed to ambient temperature. The aryl iodide (0.30 mmol), PEPPSI-IPr (0.009 mmol), and LiBr (0.90 mmol) were placed into a dry, 10 mL glass sleeve. The sleeve was placed into the metal jacket of the stainless steel pressure reactor, fitted with a rubber septum, and placed under nitrogen. NMP (2 mL) was added, and the mixture was cooled to -78 C, whereupon the previously prepared zinc acetylide solution (2 mL, 0.3 M) was added dropwise. The jacket was removed from the bath, and the pressure reactor was sealed. The reactor was evacuated and backfilled with CO(g) (three cycles, 60 psi). The reactor was heated to 80 C (oil bath) with stirring for 24 h at 60 psi of CO(g). The reaction mixture was diluted with CH2Cl2 (20 mL) and brine (20 mL). The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organics were dried (MgSO4), filtered, and concentrated under reduced pressure. The crude residue was purified by flash column chromatography, eluting with the indicated solvent to deliver the desired ketone.

Reference： [1]Tetrahedron,2011,vol. 67,p. 4344 - 4351

35
[ 6342-87-6 ]
[ 608-28-6 ]
[ 1340562-53-9 ]

Reference： [1]Journal of Organic Chemistry,2011,vol. 76,p. 8599 - 8610

36
[ 608-28-6 ]
[ 5779-47-5 ]
[ 1380442-25-0 ]

Yield	Reaction Conditions	Operation in experiment
52%		General procedure: To a reaction tube containing (17alpha-20E)-21-(tri-n-butylstannyl)-19-norpregna-1,3,5(10)20-tetraene-3,17beta-diol, 2a, were added a few crystals of 2,6 di-tert-butyl-4-methylphenol and the substituted phenyl/xylyl iodide. The tube was dried under vacuum for 24 h, then exchanged with argon at least four times. Tetrakis(triphenylphosphine) palladium (0) (0.024 g, 0.02 mmol) and dried, degassed toluene (5 mL) were added and the reaction was heated at 110 C for 6-18 h. After cooling to room temperature, the reactuib mixture was transferred to a flask with ethyl acetate (50 mL), activated charcoal was added, the mixture heated to boiling, and then filtered through a Celite pad. To the filtrate containing the substituted phenyl vinyl estradiol derivative, fluorsil (4-8 g) was added and then mixture was evaporated to dryness. Hexane was then added to the slurry and the mixture was again evaporated to dryness. The substituted phenyl vinyl estradiol was isolated using flash chromatography and characterized by 1H and 13C NMR, elemental analysis

Reference： [1]Steroids,2012,vol. 77,p. 471 - 476

37
[ 608-28-6 ]
[ 443-88-9 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 10795 - 10798

38
[ 3682-71-1 ]
[ 608-28-6 ]
[ 1394164-15-8 ]

Yield	Reaction Conditions	Operation in experiment
40%	With copper(l) iodide; 1,10-Phenanthroline; lithium tert-butoxide; In N,N-dimethyl-formamide; at 110℃; for 15h;Inert atmosphere;	General procedure: A 10-mL glass vessel equipped with J. Young O-ring tap containing a magnetic stirring bar was flame-dried under vacuum and filled with argon after cooling to room temperature. To this tube were added 2-substituted 2H-indazole (1: 0.40 mmol), CuI (7.6 mg, 0.04 mmol), 1,10-phenanthroline (7.2 mg, 0.04 mmol), LiOt-Bu (64 mg, 0.80 mmol), and haloarene (2: 0.80 mmol), followed by DMF (0.5 mL) under a stream of argon. The tube was sealed with O-ring tap, and then heated at 110 C for 15 h in an eight-well reaction block with stirring. After cooling the reaction mixture to room temperature, the mixture was passed through a short pad of Celite (EtOAc). The filtrate was concentrated and the residue was subjected to preparative HPLC (acetonitrile/water as an eluent) to afford the arylated product 3.

Reference： [1]Tetrahedron,2012,vol. 68,p. 7605 - 7612

39
[ 608-28-6 ]
[ 1415312-45-6 ]
[ 1415312-48-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With bis-triphenylphosphine-palladium(II) chloride; cesium fluoride; In methanol; at 120℃; for 0.333333h;Inert atmosphere; Microwave irradiation;	Bis(triphenylphosphine) palladium(II) chloride (12.10 mg, 0.02 mmol) and methanol (2 mL) were added to a stirred suspension of 2-(tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2H-1,2,3-triazole (21, 96 mg, 0.34 mmol), cesium fluoride (157 mg, 1.03 mmol) and 2-iodo-1,3-dimethylbenzene (0.080 mL, 0.34 mmol) , degazed and under argon. The resulting suspension was heated at 120 C for 20 minutes on the microwaves apparatus.The mixture was adsorbed on silica gel with a methanolic solution of ammonia.The crude product was purified by flash chromatography on silica gel eluting with 10 to 30% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford 4-(2,6-dimethylphenyl)-2-(tetrahydro-2H-pyran-2-yl)-2H-1,2,3-triazole (24, 80 mg, 90 %) as a pale colorless gum: UP-LCMS (tR = 0.68 min., purity = 100%), ESI+ m/z, no ion detected; 1H NMR (CDCl3, 500 MHz) delta (ppm) 7.60 (s, 1H), 7.20 (dd, J=7.8 Hz, 1H), 7.10 (d, J=7.6 Hz, 2H), 5.78 (dd, J=8.8, 2.4 Hz, 1H), 4.01 - 4.13 (m, 1H), 3.73 - 3.82 (m, 1H), 2.41 - 2.53 (m, 1H), 2.13 (s, 8H), 1.70 - 1.81 (m, 2H), 1.62 - 1.70 (m, 1H); 13C NMR (CDCl3, 126MHz) delta (ppm) 146.7, 138.2, 135.2, 130.3, 128.9, 127.9, 89.3, 67.7, 29.8, 25.2, 22.1, 21.1; HRMS m/z (ESI+) calculated for C15H19N3O: 174.10257; found: 174.10246 corresponding to M(-C5H8O)+

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6849 - 6852

40
[ 608-28-6 ]
[ 2996-92-1 ]
[ 3976-34-9 ]

Yield	Reaction Conditions	Operation in experiment
61%	With tetrabutyl ammonium fluoride; In water; toluene; at 100℃; for 20h;	General procedure: Catalyst 1a22a (43 mg, 0.1 mol % of supported palladium) was added to a solution of aryl iodide (0.40 mmol, 1.0 equiv), aryltrialkoxysilane (0.80 mmol, 2.0 equiv), TBAF·3H2O (252 mg, 0.8 mmol, 2.0 equiv) in a mixture of toluene (5 mL) and H2O (50 muL). The reaction mixture was heated at 100 C for 20 h. After cooling to rt, 1a was filtered under vacuum on a 0.2 mum membrane. The catalyst was successively washed with toluene (10 mL) and Et2O (10 mL). The combined organic phases were washed with H2O (20 mL), dried with MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash-chromatography on silica gel. Catalyst 1a was dried under vacuum and can directly be used for another Hiyama coupling.

Reference： [1]Tetrahedron,2013,vol. 69,p. 264 - 267

41
[ 608-28-6 ]
[ 1068471-18-0 ]
[ 1206629-43-7 ]

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

42
[ 608-28-6 ]
[ 1068471-18-0 ]
[ 1206629-44-8 ]

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

43
[ 608-28-6 ]
[ 912763-45-2 ]
4-(3-chlorophenyl)-1-(2,6-dimethylphenyl)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In N,N-dimethyl-formamide; at 160℃; for 48h;Inert atmosphere;	A pressure flask was charged with 4-(3-chlorophenyl)-1H-imidazole (10.82 g, 60.6 mmol) and 2-iodo-1,3-dimethylbenzene (16.87 g, 72.7 mmol). The reaction mixture was diluted with DMF (60 mL), and copper(I) iodide (1.1 g, 6.1 mmol), N,N-dimethylethane-1,2-diamine (2.6 mL, 24.2 mmol) and cesium carbonate (23.68 g, 72.7 mmol) were added. After degassing with nitrogen, the reaction mixture was stirred in an oil bath at 160 C for 48 h before being diluted with ethyl acetate and filtered through celite. The filtrate was washed with aqueous LiCl, brine and water. The product was purified by chromatography on silica gel with 0-5% EtOAc in DCM to afford 3.8 g (22%) of 4-(3-chlorophenyl)-1-(2,6-dimethylphenyl)-1H-imidazole. Synthesis of 3-(1-(2,6-dimethylphenyl)-1H-imidazol-4-yl)-N-(3-(1-(2,6-dimethylphenyl)-1H-imidazol-4-yl)phenyl)-N-phenylaniline.

Reference： [1]Patent: EP2574613,2013,A1 .Location in patent: Paragraph 0139

44
[ 608-28-6 ]
[ 107-19-7 ]
[ 1446281-93-1 ]

Yield	Reaction Conditions	Operation in experiment
32%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); diisopropylamine; In tetrahydrofuran; at 50℃;Inert atmosphere; Reflux;	3-(2,6-Dimethylphenyl)prop-2-yn-1 -ol (32). A 500 mL 3-neck flask fitted with a stir- bar, condenser, and Ar inlet was charged with <strong>[608-28-6]2,6-dimethyliodobenzene</strong> (21 .6 g, 93.1 mmol), propargyl alcohol (6.78 g, 7.15 mL, 121 mmol), /'Pr2NH (100 mL), and THF (100 mL). The resultant solution was sparged with Ar for 10 min, then Pd(PPh3) (1 .00 g, 0.93 mmol) and Cul (350 mg, 1 .86 mmol) were added. This mixture was heated at 50 C for 1 .5 hr. HPLC analysis showed the reaction to be incomplete. 8 mL more propargyl alcohol was added and the mixture was heated at reflux overnight. The reaction was still incomplete by HPLC analysis. Another 10 mL propargyl alcohol, 500 mg Pd(PPh3) , and 200 mg Cul were added, and the mixture was refluxed for 6 hr. Another 8 mL portion of propargyl alcohol was then added, and the reaction was continued at reflux overnight. The mixture was then cooled, and the solids were filtered off and rinsed with EtOAc (200 mL). The filtrate was concentrated to a dark oil and partitioned with CH2CI2 (500 mL) and saturated NH4CI (250 mL). The organic phase was washed with saturated aqueous NH CI (250 mL) and brine (200 mL) and filtered through phase separation paper. The solution was then filtered through a plug of silica gel. The silica gel was rinsed with CH2CI2 (1 2 L). The combined filtrate was concentrated to 8.5 g of a brown oil. The crude material was chromatographed on silica gel with the product eluting with 10-12% EtOAc in hexanes. The combined fractions were concentrated in vacuo, taken up in CH2CI2 (200 mL), and washed with 5% aqueous Na2S2O3 (200 mL) then brine (200 mL). The solution was filtered through phase separation paper and concentrated in vacuo to give 5.0 g of 32 as an orange solid (32%). 1H NMR (60 MHz, CDCI3): delta 7.3-6.8 (m, 3H), 4.5 (s, 2H), 2.8 (s, 1 H), 2.4 (s, 6H) ppm. HPLC analysis (5:10:85 H2O:A1 :MeOH) showed a purity of greater than 99% with a retention time of 3.7 min

Reference： [1]Patent: WO2013/101926,2013,A1 .Location in patent: Page/Page column 29-30

45
[ 608-28-6 ]
[ 476004-80-5 ]
[ 1382179-43-2 ]

Reference： [1]Organometallics,2013,vol. 32,p. 4423 - 4430

46
[ 608-28-6 ]
[ 1447710-10-2 ]
[ 1447710-16-8 ]

Yield	Reaction Conditions	Operation in experiment
77%	With allyl(cyclopentadiene)palladium(II); tetrabutylammomium bromide; triphenylphosphine; potassium hydroxide In water; toluene at 80℃; for 10h; Inert atmosphere; Schlenk technique;

Reference： [1]Wakioka, Masayuki; Nakamura, Yuki; Hihara, Yoshihiro; Ozawa, Fumiyuki; Sakaki, Shigeyoshi [Organometallics, 2013, vol. 32, # 15, p. 4423 - 4430]

47
[ 608-28-6 ]
[ 98-80-6 ]
[ 1449510-60-4 ]
[ 101-16-6 ]

Reference： [1]Chemistry - A European Journal,2013,vol. 19,p. 10334 - 10342

48
[ 67-56-1 ]
[ 608-28-6 ]
[ 201230-82-2 ]
[ 14920-81-1 ]
[ 108-38-3 ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 566 - 574

49
[ 67-56-1 ]
[ 608-28-6 ]
[ 201230-82-2 ]
[ 14920-81-1 ]

Reference： [1]Organic Process Research and Development,2008,vol. 12,p. 566 - 574

50
[ 608-28-6 ]
[ 393827-07-1 ]
[ 1565872-69-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tetrabutylammomium bromide; palladium diacetate; triethylamine; 1,3-di-tert-butyl-1H-imidazol-3-ium chloride; In ethanol; water; at 80℃; for 5h;	General procedure: Heck coupling reactions were carried out using aryl iodides (3a-j) (1 mmol), 2-Vinyl-N-Boc-piperidine (2) (1.2 mmol), and Et3N as base (2 mmol) dissolved in 10 ml of aq.ethanol (water/ethanol = 9:1). An appropriate amount of NHC precursor (i) (0.1 mmol), Pd(OAc)2 (0.05 mmol), and TBAB (0.025 mmol) were added to this mixture. The reaction mixture was heated to 80 C for 5 hrs. The coupled product was extracted with DCM (2 x 20 ml). The combined organic layers were dried (anhydrous Na2SO4) and evaporated under reduced pressure to afford a crude product which was subjected to column chromatography to afford pure E-Olefins (4a-j).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1180 - 1183

51
[ 608-28-6 ]
[ 768-60-5 ]
[ 1243249-31-1 ]

Yield	Reaction Conditions	Operation in experiment
90%	With C20H29Cl2N5O2Pd; potassium carbonate; In ethanol; at 80℃; for 2h;	General procedure: A vial was charged with an aryl halide (0.1 mmol), an aryl or alkylacetylene(0.11 mmol), K2CO3 (0.15 mmol), palladium catalyst (0.05 mol %), and EtOH(2 mL). The mixture was refluxed with stirring for 2 h. After this time, themixture was cooled and CH2Cl2-n-hexane (1:2, 2 mL) and H2O (2 mL) wereadded. The organic layer was separated, filtered through a small amount ofsilica gel and analyzed by GC-MS. The solvent was removed and the residueweighed and analyzed by 1H NMR.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 2101 - 2103

52
[ 608-28-6 ]
[ 22871-77-8 ]
[ 147424-62-2 ]

Yield	Reaction Conditions	Operation in experiment
75%	With C₁₈H₃₃P*CuCl; sodium t-butanolate In toluene at 120℃; for 15h; Inert atmosphere; Glovebox;

Reference： [1]Zhou, Yiqing; You, Wei; Smith, Kevin B.; Brown, M. Kevin [Angewandte Chemie - International Edition, 2014, vol. 53, # 13, p. 3475 - 3479][Angew. Chem., 2014, vol. 126, # 13, p. 3543 - 3547,5]

53
[ 608-28-6 ]
[ 501374-30-7 ]
2,6-dimethyl-4'-(trifluoromethyl)-1,1'-biphenyl [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 3475 - 3479
Angew. Chem.,2014,vol. 126,p. 3543 - 3547,5

54
[ 100379-00-8 ]
[ 608-28-6 ]

Yield	Reaction Conditions	Operation in experiment
78%	With iodine; potassium carbonate; In acetonitrile; at 80℃; for 12h;Inert atmosphere; Schlenk technique; Sealed tube;	General procedure: Arylboronic acid 1 (0.5 mmol) and K2CO3 (1 mmol, 138.0mg) were added to a 20 mL Schlenk-tube equipped with amagnetic stir bar. The tube was evacuated twice and backfilledwith N2. MeCN (2 mL) and I2 (0.75 mmol, 191 mg)were added to the tube at r.t. under a stream of N2, and thetube was sealed and placed into a pre-heated oil bath at 80 Cfor 8-12 h. The resulting solution was cooled to r.t. and H2O(10 mL) was added. The aq layer was extracted with EtOAc (3 × 5 mL). For products 2s and 2t, HCl (1 M) was added tothe aq solution until pH 2 before extraction. The combinedorganic phase was dried over anhydrous Na2SO4, filteredand concentrated by rotary evaporation. Purification of theresidue by column chromatography on silica gel providedthe desired product 2a-v

Reference： [1]Synlett,2014,vol. 25,p. 995 - 1000

55
[ 608-28-6 ]
[ 81290-20-2 ]
[ 41818-96-6 ]

Yield	Reaction Conditions	Operation in experiment
27 %Chromat.	With potassium fluoride; copper(l) iodide; 1,10-Phenanthroline; Trimethyl borate In dimethyl sulfoxide at 60℃; for 5h; Inert atmosphere;

Reference： [1]Gonda, Zsombor; Kovacs, Szabolcs; Weber, Csaba; Gati, Tamas; Meszaros, Attila; Kotschy, Andras; Novak, Zoltan [Organic Letters, 2014, vol. 16, # 16, p. 4268 - 4271]

56
[ 504-29-0 ]
[ 608-28-6 ]
[ 376353-22-9 ]

Yield	Reaction Conditions	Operation in experiment
97%	With copper(l) iodide; potassium tert-butylate; In 1,4-dioxane; at 110℃; for 24h;Sealed tube; Inert atmosphere;	General procedure: A 10 mL flask equipped with a Teflon valve was charged with a magnetic stir bar, CuI (2 mg, 1mol%), Heteroarylamine (1.5 mmol), KOtBu (224 mg, 2.0 mmol), solid aryl halides (1.0 mmol). The tube was evacuated and backfilled with argon. Under a counter flow of argon, dioxane (1.5mL), aryl halides (1.0 mmol, if liquid) were added by syringe. The tube was sealed. The reaction mixture was allowed to stir at 110 C (X=I) or 130 C (X= Br) for 24 h. Then the mixture was cooled to room temperature and added 5.0 mL brine. Subsequently, the mixture was extracted with ethyl acetate. The organic layers were collected, dried over Na2SO4, filtered and the solvent was removed under vacuum. The residue was purified by column chromatography on silica gel.

Reference： [1]Tetrahedron Letters,2014,vol. 55,p. 7121 - 7123

57
[ 608-28-6 ]
[ 79606-46-5 ]
C₂₁H₂₇NO [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2015,vol. 54,p. 4665 - 4668
Angew. Chem.,2015,vol. 127,p. 4748 - 4751,4

58
[ 608-28-6 ]
[ 1356364-32-3 ]
2-(3-((2,6-dimethylphenyl)ethynyl)phenyl)benzofuran [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With potassium carbonate; at 20℃; for 1h;	General procedure: The PdNPs were prepared by using a protocol established from ourgroup.4a A freshly prepared solution of PdNPs (5 mL) was taken up in a25-mL round-bottomed flask. To this solution, K2CO3 (0.138 g, 1mmol was added followed by 4-iodoanisole (0.117 g, 0.5 mmol) or 2-iodo-1,3-dimethylbenzene (0.116 g, 0.5 mmol) and 2-(3-ethynylphenyl)benzofuran (0.109 g, 0.5 mmol). Then, the mixture was stirred atr.t. in an open atmosphere. The reaction was monitored by TLC untilcomplete consumption of the starting materials.

Reference： [1]Synthesis,2015,vol. 47,p. 1661 - 1668

59
[ 608-28-6 ]
5-[(2R,6R)-2-(hydroxymethyl)-6-methylmorpholin-4-yl]quinoline-8-carbonitrile [ No CAS ]
5-((2R,6R)-2-((2,6-dimethylphenoxy)methyl)-6-methylmorpholino)quinoline-8-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17.6%	With copper(l) iodide; 1,1'-binaphthyl-2,2'-diamine; caesium carbonate; In dimethyl sulfoxide; at 110℃; for 12h;Microwave irradiation;	ER-886137: In a dry microwave reaction vessel was added cesium carbonate (172.5 mg, 0.529 mmol), copper (I) iodide (33.6 mg, 0.176 mmol), 1,1?-binaphthyl-2,2?-diamine (50.2 mg, 0.177 mmol, 2-iodo-1,3-dimethylbenzene (123 mg, 0.53 mmol) in DMSO (0.3 mL) followed by 13 (50 mg, 0.177 mmol). The reaction mixture was microwaved at 110 C. for 12 h after which time the mixture was directly injected on a reverse-phase preparative HPLC column (Water's X-Bridge C18 19×100 mm column; gradient using 0-50% acetonitrile in water containing 0.05% TFA) for purification eluting with, providing a crude product. The crude product was purified over silica gel (Biotage eluting with a gradient from 25% EtOAc in heptane to 100% EtOAc) to provide ER-886137 (12.1 mg, 0.031 mmol, 17.6% yield) after combining the desired collected fractions, concentration and drying in vacuo.

Reference： [1]Patent: US2015/105370,2015,A1 .Location in patent: Paragraph 0646

60
[ 79-21-0 ]
[ 608-28-6 ]
[ 123084-61-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	In glacial acetic acid at 20℃; for 20h;
69%	With acetic anhydride; glacial acetic acid at -10 - 20℃;
	With glacial acetic acid In 2,2,2-trifluoroethanol at 20℃;

With glacial acetic acid In 2,2,2-trifluoroethanol at 20℃;

Preparation of Aryl(TMP)iodonium(III) Acetate Aryl iodide (30.0 mmol) was dissolved in 2,2,2-trifluoroethanol (TFE,30.0 mL, 1.0 M), and then AcOOH (60.0 mmol, 9% solution in AcOH, 48.8mL) was added to the reaction mixture. After stirring at roomtemperature for overnight, the reaction mixture was concentrated underreduced pressure. Addition of Et2O to the residue generated aprecipitant, which was collected by filtration to afford the corresponding(diacetoxyiodo)arenes. (Diacetoxyiodo)arene (20.0 mmol) was dissolvedin 2,2,2-trifluoroethanol (TFE, 20.0 mL, 1.0 M), and then 1,3,5-trimethoxybenzene (TMP-H, 24.0 mmol, 1.2 equiv, 4.04 g) was added tothe reaction mixture at 0 °C. After stirring at room temperature for 24 h,the reaction mixture was concentrated under reduced pressure. Additionof Et2O to the residue generated a precipitant, which was collected byfiltration to afford the corresponding TMP-iodonium(III) acetate salts

Reference： [1]Miralles; Romero; Fernández; Muñiz [Chemical Communications, 2015, vol. 51, # 74, p. 14068 - 14071]
[2]Haskali, Mohammad B.; Telu, Sanjay; Lee, Yong-Sok; Morse, Cheryl L.; Lu, Shuiyu; Pike, Victor W. [Journal of Organic Chemistry, 2016, vol. 81, # 1, p. 297 - 302]
[3]Kikushima, Kotaro; Miyamoto, Naoki; Watanabe, Kazuma; Koseki, Daichi; Kita, Yasuyuki; Dohi, Toshifumi [Organic Letters, 2022, vol. 24, # 10, p. 1924 - 1928]
[4]Kikushima, Kotaro; Morita, Aki; Elboray, Elghareeb E.; Bae, Taeho; Miyamoto, Naoki; Kita, Yasuyuki; Dohi, Toshifumi [Synthesis, 2022, vol. 54, # 23, p. 5192 - 5202]

61
[ 608-28-6 ]
[ 872-35-5 ]
2-((2,6-dimethylphenyl)thio)-1H-imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	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), 2-mercaptoimidazole/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

62
[ 591-50-4 ]
[ 608-28-6 ]
[ 22040-02-4 ]

Yield	Reaction Conditions	Operation in experiment
82%	With Pd(tris[2-(diphenylphosphino)ethyl]phosphine tetrasulfide)(dibenzylideneacetone); caesium carbonate; In isopropyl alcohol; at 80℃; for 9h;	General procedure: Iodobenzene (1.2 mmol) and [Pd(pp3S4)(dba)] (1 mol %) were stirred in isopropanol (2.5 ml). Alcohol (1 mmol) followed by Cs2CO3 (5 mol %) were added to the above solution in the atmosphere of air. The mixture was heated to 80 C and the progress of the reaction was monitored by TLC. Rest of the procedure is same as described above.

Reference： [1]Journal of Organometallic Chemistry,2015,vol. 781,p. 23 - 34

63
[ 710348-69-9 ]
[ 608-28-6 ]
5-(2,6-dimethylphenyl)-1,3-dihydrobenzimidazol-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
24%	With dichloro[1,1?-bis[bis(1,1-dimethylethyl)phosphino]ferrocene-P,P?]palladium; In 1,4-dioxane; water; at 100.0℃; for 16.0h;Inert atmosphere;	To a so?ution of 5-(4455- tetramethy-1 32-dioxaboroan-2-y)-1 H-benzo[djimidazo-2(3H)-one (ntermediate 28, 100mg 0.38 mmo), potassium phosphate (204 mg, 0.96 mmo), and PdC2(dtbpf) (13 mg0.019 rnrno) in 4:1 dioxane:water (2.0 mL) was added 2,6-dimethyhodobenzene at once(178 mg 0.77 mmo). The mixture was degassed with nitrogen for 10 minutes and then heated at 100 C for 16 h, After cooHg to rt, the reaction mixture was duted wfth water and extracted w[th EtOAc (x 3). The combned organc extracts were dried (Na2SO4), fUtered and concentrated under reduced pressure. Purficaton (FCC, SO2; 0 - 100% EtOAc/hexanes) afforded the tWe compound as a wh[te sod (22 mg, 24% yed). MS(ES): mass cacd. for C15H14N20, 238.1; m/zfound, 239.0 [M+H]. 1H NMR (400 MHz, CD3OD) 5 713- 7.02 (m, 4H), 6.86- 6.80 (m, 1H), 6.76 (dd, J= 80, 1.4 Hz, 1 H), 2.00 (s, 6H).

Reference： [1]Patent: WO2016/176449,2016,A1 .Location in patent: Page/Page column 97; 98
[2]ACS Medicinal Chemistry Letters,2018,vol. 9,p. 821 - 826

64
[ 608-28-6 ]
[ 124-38-9 ]
[ 1123-56-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With carbon supported Pd nanoparticles; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 80℃; under 7500.75 Torr; for 12h;Sealed tube; Green chemistry;	In a 20 ml reactor, place 10 ml acetonitrile, 5mmol 1,3-dimethyl-2-iodobenzene, 15mmol PMHS with weight average molecular weight of 2000, 5.5mmol DBU, 0.01mmol palladium carbon catalyst consisting of a mass ratio of 10: 100 palladium nanoparticles and activated carbon carrier. Seal. Heat to 80 C. Place CO2 to 1MPa. React for 12 hours. The results are as follows: 1,3-dimethyl-2-iodobenzene conversion is 100%; main product is 1,3-dimethyl-2-formylbenzene, yield is 76%.

Reference： [1]Patent: CN104803835,2017,B .Location in patent: Paragraph 0039; 0072; 0073
[2]Organic Letters,2018,vol. 20,p. 5130 - 5134

65
[ 1493-13-6 ]
[ 608-28-6 ]
[ 108-67-8 ]
(2,6-dimethylphenyl)(2,4,6-trimethylphenyl)iodonium triflate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0℃; for 2h;Inert atmosphere; Sealed tube;	General procedure: The reaction was generally performed with 2.0 equivalents of TfOH. m-CPBA (65%active oxidant, 2.6 mmol) and aryl iodide (2.3 mmol) were dissolved in DCM (20 mL)in a sealed tube. The arene (2.6 mmol) was added and the solution was cooled to 0 oC,followed by dropwise addition of TfOH (4.6 mmol), and resulted in a colouredsolution. The reaction mixture was stirred for about 2 h, subsequently concentratedunder vacuum. Et2O was added and the mixture was stirred at room temperature for30 mins to precipitate out an off-white solid.

Reference： [1]Tetrahedron,2017,vol. 73,p. 3591 - 3595

66
[ 608-28-6 ]
[ 766-47-2 ]
[ 1352625-72-9 ]

Yield	Reaction Conditions	Operation in experiment
81%	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.

Reference： [1]Journal of Organometallic Chemistry,2018,vol. 860,p. 98 - 105

67
[ 608-28-6 ]
C₁₈H₁₅N₃O₂ [ No CAS ]
5-(2,6-dimethylphenyl)-4-methyl-N,6-diphenylpyrimidin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33%	With triphenylphosphine; silver carbonate; palladium dichloride; In N,N-dimethyl acetamide; at 155 - 160℃; for 16h;Inert atmosphere; Molecular sieve;	General procedure: A ame-dried tube lled with argon was charge with 2-aminopyrimidine-5-carboxylic acid 2 (0.13 mmol), PdCl2 (5 mol%), PPh3 (10 mol %), Ag2CO3 (0.39 mmol), ArI (0.26 mmol) and 4 Amolecular sieves (100 mg) in DMA (2 mL). The resulting mixturewas stirred at 155e160C for 16 h. After cooling to room temper-ature, the mixture was ltered through Celite pad and washed withEtOAc (25 mL). The ltrate was washed with water (5 mL x 2) andbrine (5 mL), dried over anhydrous MgSO4, ltered, and concen-trated under reduced pressure. The crude product was puried bysilica gel column chromatography (n-hexane/EtOAc 10:1 v/v) toafford the corresponding product.

Reference： [1]Tetrahedron,2018,vol. 74,p. 3843 - 3851

68
[ 608-28-6 ]
[ 16419-60-6 ]
[ 10273-87-7 ]

Yield	Reaction Conditions	Operation in experiment
94%		2,2',6-trimethyl-1,1'-biphenyl (89): To a mixture of Ni-Cat.(0.0125 mmol Nil2+0.025 mmol VIa) and Ar-I 87 (0.036mL, 0.058 g, 0.25 mmol) 1.0 mL of CPME was added. Themixture was stirred for 10 mins. Then the water (0.02 mL,0.02 g, 1.11 mmol) was added. To the mixture, boronic acid88 (0.068 g, 0.5 mmol), bases (0.160 g, 0.75 mmol) wereadded. The reaction mixture was stirred at 105 C. (asmentioned) and aliquot was taken after different time intervalto analyze the data by GC/MS. After that the reactionmixture was filtered through neutral alumina, concentratedunder vacuum, purified by flash chromatography withhexane.1 H NMR (CDC13, 400 MHz): o1.99 (s, 6H), 2.01 (s,3H), 7.05-7.08 (m, lH), 7.14-7.35 (m, 6H); 13C NMR(CDC13, 100 MHz): o19.4, 20.3, 126.0, 126.9, 126.9, 127.2,128.8, 130.0, 135.6, 135.8, 140.5, 141.0.

Reference： [1]Patent: US2018/155375,2018,A1 .Location in patent: Paragraph 0305

69
[ 608-28-6 ]
[ 201230-82-2 ]
[ 1123-56-4 ]

Yield	Reaction Conditions	Operation in experiment
61%	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]Angewandte Chemie - International Edition,2018,vol. 57,p. 10362 - 10367
Angew. Chem.,2018,vol. 130,p. 10519 - 10524,6

70
[ 608-28-6 ]
[ 201230-82-2 ]
[ 62285-58-9 ]
[ 108-38-3 ]
[ 1123-56-4 ]

Reference： [1]Angewandte Chemie - International Edition,2018,vol. 57,p. 10362 - 10367
Angew. Chem.,2018,vol. 130,p. 10519 - 10524,6

71
[ 775351-57-0 ]
[ 608-28-6 ]
4-fluoro-2',6'-dimethyl-[1,1'-biphenyl]-3-carbonitrile [ No CAS ]

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

72
[ 608-28-6 ]
[ 124-38-9 ]
[ 6575-13-9 ]

Yield	Reaction Conditions	Operation in experiment
64%Chromat.	With 1,4-diaza-bicyclo[2.2.2]octane; copper(I) oxide; phenylsilane; ammonia; In 1-methyl-pyrrolidin-2-one; at 130℃; under 2280.15 Torr; for 24h;Sealed tube;	General procedure: Under nitrogen atmosphere, Cu2O (10 mol %), DABCO (25 mol %), and a stirring bar were added into a 10 mL oven-dried sealed glass tube (as shown in Figure S1). Then NMP (0.5 mL), aryl iodides (0.125 mmol, 1.0 equiv.) and PhSiH3 (0.75 mmol, 6 equiv.) were injected by syringe. The tube was then sealed and CO2 (0.67 mmol, 5.4 equiv., 15 mL) as well as NH3 (0.67 mmol, 5.4 equiv., 15 mL) were injected by syringe after N2 was removed under vacuum. Finally, the mixture was stirred for 24 hr in a pre-heated-to-130 C alloyed block. After the reaction was finished, the tube was cooled to room temperature and the pressure was carefully released. The yield of were measured by GC analysis using dodecane as the internal standard or by flash chromatography on silica gel (petroleumether/ethyl acetate).

Reference： [1]Chem,2018,vol. 4,p. 2883 - 2893

73
[ 496-15-1 ]
[ 608-28-6 ]
[ 1745-81-9 ]
C₂₅H₂₇NO [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 4196 - 4202

74
[ 2343-22-8 ]
[ 608-28-6 ]
[ 1745-81-9 ]
C₂₅H₂₆FNO [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 4196 - 4202

75
[ 22190-33-6 ]
[ 608-28-6 ]
[ 1745-81-9 ]
C₂₅H₂₆BrNO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With 2-acetylpyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl-ammonium chloride; sodium carbonate In 1,4-dioxane at 25℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Han, Chunhua; Fu, Zhiyuan; Guo, Songjin; Fang, Xinxin; Lin, Aijun; Yao, Hequan [ACS Catalysis, 2019, vol. 9, # 5, p. 4196 - 4202]

76
[ 62108-16-1 ]
[ 608-28-6 ]
[ 1745-81-9 ]
C₂₆H₂₉NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With 2-acetylpyridine; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tetrabutyl-ammonium chloride; sodium carbonate In 1,4-dioxane at 25℃; for 24h; Inert atmosphere; regioselective reaction;

Reference： [1]Han, Chunhua; Fu, Zhiyuan; Guo, Songjin; Fang, Xinxin; Lin, Aijun; Yao, Hequan [ACS Catalysis, 2019, vol. 9, # 5, p. 4196 - 4202]

77
[ 608-28-6 ]
[ 65826-95-1 ]
[ 1745-81-9 ]
C₂₆H₂₉NO [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 4196 - 4202

78
[ 608-28-6 ]
[ 1745-81-9 ]
[ 177478-49-8 ]
C₂₈H₃₁NO₃ [ No CAS ]

Reference： [1]ACS Catalysis,2019,vol. 9,p. 4196 - 4202

79
[ 4250-81-1 ]
[ 608-28-6 ]
1,3-dimethyl-2-(1-phenylpenta-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-phenyl-1-pentyne 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill with nitrogen repeatedly 10 times, stir at room temperature for 15min, add 0.5mmol of water,Then placed in a reaction dish at 100 C for 16h;After cooling to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, and the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin-layer chromatography to obtain 17.4 mg of the target product as a colorless oil. The yield was 70%.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0028-0031

80
[ 608-28-6 ]
[ 622-76-4 ]
1,3-dimethyl-2-(1-phenylbuta-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-phenyl-1-butyne 0.25 mmol and N, N-dimethylformamide 1 mL were added toIn a 15 mL reaction tube, repeatedly fill 10 times with nitrogen, and stir at room temperature for 15 min.Add 0.5 mmol of water,Then placed in a reaction dish at 100 C for 16h; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin layer chromatography to obtain 7.3mg of the target product. Color oil, 31% yield.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0056-0059

81
[ 608-28-6 ]
[ 1129-65-3 ]
1,3-dimethyl-2-(1-phenylhexyl-1,2-diene-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-phenyl-1-hexyne 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill with nitrogen repeatedly 10 times, stir at room temperature for 15 min, add 0.5 mmol of water, and place in a reaction dish at 100 C for 16 h; cool to room temperature, dilute the reaction solution with ethyl acetate, wash with water, and dry the organic phase with anhydrous Na2SO4 , Filtered, concentrated, and purified by thin layer chromatography to obtain 14.9 mg of the target product as a colorless oil with a yield of 57%.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0060-0063

82
[ 608-28-6 ]
[ 79756-89-1 ]
1,3-dimethyl-2-(1-(p-tolyl)penta-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-methyl-4- (pent-1-yn-1-yl) benzene 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill it repeatedly with nitrogen 10 times, stir at room temperature for 15 min, add 0.5 mmol of water, and place in a reaction dish at 100 C for 16 h; cool to room temperature, dilute the reaction solution with ethyl acetateWash with water, dry the organic phase over anhydrous Na2SO4, filter, and concentrate.Purification by thin layer chromatography gave 13.4 mg of the target product as a colorless oil with a yield of 51%.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0064-0067

83
[ 608-28-6 ]
[ 445424-02-2 ]
2-(1-(4-fluorophenyl)penta-1,2-dien-1-yl)-1,3-dimethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-fluoro-4- (pent-1-yn-1-yl) benzene 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill with nitrogen repeatedly 10 times, stir at room temperature for 15min, add 0.5mmol of water,Then placed in a reaction tray at 100 C for 16 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin-layer chromatography to obtain 14.1 mg of the target product. Color oil, 51% yield.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0068-0071

84
[ 608-28-6 ]
1-(pent-1-yn-1-yl)-4-(trifluoromethyl)benzene [ No CAS ]
1,3-dimethyl-2-(1-(4-(trifluoromethyl)phenyl)penta-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	0.2 mmol of potassium carbonate, 0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol, 18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1- (pent-1-yn-1-yl) -4- (trifluoromethyl) benzene 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube, repeatedly filled with nitrogen 10 times, stirred at room temperature for 15 min, 0.5 mmol of water was added, and then placed in a reaction tray at 100 C. for 16 hours; cooled to room temperature The reaction solution was diluted with ethyl acetate, washed with water, and the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin layer chromatography to obtain 13.6 mg of the target product as a colorless oil with a yield of 43%.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0076-0079

85
[ 608-28-6 ]
N-(4-(pent-1-yn-1-yl)phenyl)acetamide [ No CAS ]
N-(4-(1-(2,6-dimethylphenyl)penta-1,2-dien-1-yl)phenyl)acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,N- (4- (pent-1-yn-1-yl) phenyl) acetamide 0.25 mmolAnd 1 mL of N, N-dimethylformamide into a 15 mL reaction tube,Fill with nitrogen repeatedly 10 times, stir at room temperature for 15min, add 0.5mmol of water,Then placed in a reaction tray at 100 C for 16 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated, and purified by thin layer chromatography to obtain 13.4 mg of the target product. Color oil, 44% yield

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0072-0075

86
[ 608-28-6 ]
[ 1416339-67-7 ]
1,3-dimethyl-2-(1-(m-tolyl)penta-1,2-dien-1-yl)benzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol, 1,3-dimethyl-2-iodobenzene 0.1mmol,1-methyl-3- (pent-1-yn-1-yl) benzene 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill with nitrogen repeatedly 10 times, stir at room temperature for 15min, add 0.5mmol of water,Then placed in a reaction tray at 100 C for 16 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated,Purification by thin layer chromatography gave 15.5 mg of the target product as a colorless oil with a yield of 59%.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0080-0083

87
[ 608-28-6 ]
[ 1417514-18-1 ]
2-(1-(3-fluorophenyl)penta-1,2-dien-1-yl)-1,3-dimethylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
53%	With tris-(dibenzylideneacetone)dipalladium(0); 18-crown-6 ether; 1,3-bis-(diphenylphosphino)propane; potassium carbonate; In water; N,N-dimethyl-formamide; at 100℃; for 16h;Inert atmosphere;	Add 0.2 mmol of potassium carbonate,0.005 mmol of tris (dibenzylideneacetone) dipalladium,1,3-bis (diphenylphosphine) propane 0.02mmol,18-crown-6-ether 0.1mmol,1,3-dimethyl-2-iodobenzene 0.1 mmol,1-fluoro-3- (pent-1-yn-1-yl) benzene 0.25 mmol and1 mL of N, N-dimethylformamide was added to a 15 mL reaction tube,Fill with nitrogen repeatedly 10 times, stir at room temperature for 15min, add 0.5mmol of water,Then placed in a reaction tray at 100 C for 16 hours; cooled to room temperature, the reaction solution was diluted with ethyl acetate, washed with water, the organic phase was dried over anhydrous Na2SO4, filtered, concentrated and purified by thin layer chromatography to obtain 14.1 mg of the target product Colorless oil with 53% yield.

Reference： [1]Organic Letters,2019,vol. 21,p. 7795 - 7798
[2]Patent: CN110256184,2019,A .Location in patent: Paragraph 0084-0087

88
[ 608-28-6 ]
[ 115591-23-6 ]
(E)-5-(2,6-dimethylstyryl)-1,3-diphenyl-1H-1,2,4-triazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
30%	With potassium phosphate; palladium diacetate; In N,N-dimethyl-formamide; at 110℃; for 4h;Inert atmosphere; Sealed tube;	General procedure: A 10 mL 2 dram screwed tube equipped with a magnetic stirring bar was charged with 5-vinyl-1,2,4-triazole (0.17 mmol, 1.0 equiv), an organic halide (0.17 mmol, 1.0 equiv), and K3PO4 (108 mg, 0.32 mmol, 2.0 equiv); then Pd(OAc)2 (1.7 mg, 0.008 mmol) were added, followed by DMF (1.0 mL), which was added to the mixture via syringe at r.t. under argon. The tube was sealed and put into a preheated oil bath at 110 C for 4 h. The mixture was cooled to r.t quenched with H2O (20 mL). The layers were separated and the aqueous layer was extracted with Diethyl Ether (3 × 20 mL). The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was then purified by preparatory TlC [silica gel, EtOAc-PE, 3-7].

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

Same Skeleton Products

Related Products

Historical Records

Related Functional Groups of
[ 608-28-6 ]

Aryls

[ 866996-02-3 ]

4-Ethyl-1-iodo-2-methylbenzene

Similarity: 0.93

[ 90-14-2 ]

1-Iodonaphthalene

Similarity: 0.90

[ 31599-60-7 ]

1-Iodo-2,3-dimethylbenzene

Similarity: 0.87

[ 1285718-21-9 ]

4-Iodo-2,3-dihydro-1H-indene

Similarity: 0.85

[ 25309-64-2 ]

1-Ethyl-4-iodobenzene

Similarity: 0.83

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. 608-28-6 ] {[proInfo.proName]}

Quality Control of [ 608-28-6 ]

Related Doc. of [ 608-28-6 ]

Product Details of [ 608-28-6 ]

Calculated chemistry of [ 608-28-6 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 608-28-6 ]

Application In Synthesis of [ 608-28-6 ]

[ 608-28-6 ] Synthesis Path-Upstream 1~16

[ 608-28-6 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 608-28-6 ]

Aryls

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 608-28-6 ]