[ CAS No. 873-76-7 ] {[proInfo.proName]}

Name: 873-76-7|(4-Chlorophenyl)methanol|98%
Brand: Ambeed
SKU: A116380
Price: 5.0 USD
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3d Animation Molecule Structure of 873-76-7

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Quality Control of [ 873-76-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 873-76-7 ]

Product Details of [ 873-76-7 ]

CAS No. :	873-76-7	MDL No. :	MFCD00004652
Formula :	C₇H₇ClO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PTHGDVCPCZKZKR-UHFFFAOYSA-N
M.W :	142.58	Pubchem ID :	13397
Synonyms :

Calculated chemistry of [ 873-76-7 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	37.58
TPSA :	20.23 Å²

Pharmacokinetics

GI absorption :	High
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) :	-5.78 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.92
Log Po/w (XLOGP3) :	1.96
Log Po/w (WLOGP) :	1.68
Log Po/w (MLOGP) :	2.14
Log Po/w (SILICOS-IT) :	2.33
Consensus Log Po/w :	2.01

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.39
Solubility :	0.586 mg/ml ; 0.00411 mol/l
Class :	Soluble
Log S (Ali) :	-2.01
Solubility :	1.39 mg/ml ; 0.00977 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.82
Solubility :	0.217 mg/ml ; 0.00152 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 873-76-7 ]

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 [ 873-76-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 873-76-7 ]
Downstream synthetic route of [ 873-76-7 ]

[ 873-76-7 ] Synthesis Path-Upstream 1~23

1
[ 873-76-7 ]
[ 16687-61-9 ]

Reference： [1] Journal of Chemical Research, 2017, vol. 41, # 1, p. 25 - 29

2
[ 104-88-1 ]
[ 104-86-9 ]
[ 873-76-7 ]

Reference： [1] Organic Letters, 2002, vol. 4, # 12, p. 2055 - 2058
[2] Tetrahedron, 2008, vol. 64, # 7, p. 1213 - 1217

3
[ 873-76-7 ]
[ 104-86-9 ]

Reference： [1] ChemCatChem, 2018, vol. 10, # 9, p. 1993 - 1997
[2] Organic Letters, 2014, vol. 16, # 2, p. 484 - 487
[3] Organic Letters, 2014, vol. 16, # 17, p. 4424 - 4427

4
[ 623-03-0 ]
[ 21913-13-3 ]
[ 104-86-9 ]
[ 873-76-7 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 8, p. 2097 - 2101
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 8, p. 2097 - 2101

5
[ 619-56-7 ]
[ 104-86-9 ]
[ 873-76-7 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1994, vol. 42, # 2, p. 402 - 404

6
[ 873-76-7 ]
[ 25026-34-0 ]

Reference： [1] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350

7
[ 141-97-9 ]
[ 57-13-6 ]
[ 873-76-7 ]
[ 5948-71-0 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: With T₃P; dimethyl sulfoxide In ethyl acetate at 20℃; Inert atmosphere; Green chemistry Stage #2: at 60 - 70℃; Inert atmosphere; Green chemistry	General procedure: To a solution of alcohol (1.0 mmol) in a mixture of solvents ethyl acetate (4 mL) and DMSO (2 mL), was added T3P® (2 mmol, 50 percent solution in ethyl acetate), the resulting reaction mixture was stirred at room temperature for 1-2 h under nitrogen atmosphere. The reaction was monitored by TLC. β-ketoester/β-oxodithioester (1.0 mmol) and urea (1.5 mmol) were added and stirred further 4-6 h at 60-70 °C. After completion of the reaction, solvent was evaporated and mixture was poured into crushed ice. Stirring was continued for several minutes. The solid product was filtered, washed with cold water and recrystallized from ethanol to get pure product.

Reference： [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 32, p. 6994 - 6998
[2] Heterocycles, 2005, vol. 65, # 4, p. 767 - 773
[3] Chemistry Letters, 2014, vol. 43, # 2, p. 178 - 180

8
[ 873-76-7 ]
[ 5948-71-0 ]

Reference： [1] Letters in Organic Chemistry, 2018, vol. 15, # 4, p. 241 - 245

9
[ 873-76-7 ]
[ 790-41-0 ]

Reference： [1] New Journal of Chemistry, 2017, vol. 41, # 3, p. 931 - 939
[2] Tetrahedron Letters, 2017, vol. 58, # 26, p. 2533 - 2536

10
[ 10442-39-4 ]
[ 873-76-7 ]
[ 140-53-4 ]

Reference： [1] Journal of Organic Chemistry, 2004, vol. 69, # 7, p. 2562 - 2564

11
[ 873-76-7 ]
[ 140-53-4 ]

Reference： [1] Bulletin of the Chemical Society of Japan, 2006, vol. 79, # 7, p. 1106 - 1117
[2] Chemistry Letters, 2004, vol. 33, # 9, p. 1192 - 1193
[3] Scientia Pharmaceutica, 2001, vol. 69, # 4, p. 329 - 350

12
[ 106-43-4 ]
[ 2420-26-0 ]
[ 5306-98-9 ]
[ 615-74-7 ]
[ 104-88-1 ]
[ 873-76-7 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 4, p. 551 - 556

13
[ 899426-20-1 ]
[ 16251-45-9 ]
[ 873-76-7 ]

Reference： [1] Chemistry - A European Journal, 2006, vol. 12, # 14, p. 3896 - 3904

14
[ 66230-04-4 ]
[ 1745-18-2 ]
[ 622-98-0 ]
[ 1875-88-3 ]
[ 2012-74-0 ]
[ 23853-78-3 ]
[ 3739-38-6 ]
[ 938-95-4 ]
[ 39515-51-0 ]
[ 873-76-7 ]

Reference： [1] Journal of the Brazilian Chemical Society, 2015, vol. 26, # 9, p. 1831 - 1837

15
[ 873-76-7 ]
[ 874-89-5 ]

Reference： [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 38, p. 10035 - 10039[2] Angew. Chem., 2013, vol. 125, # 38, p. 10219 - 10223

16
[ 873-76-7 ]
[ 874-89-5 ]

Reference： [1] Organometallics, 2013, vol. 32, # 12, p. 3537 - 3543

17
[ 1126-46-1 ]
[ 4068-78-4 ]
[ 22717-55-1 ]
[ 873-76-7 ]

Reference： [1] Organic and Biomolecular Chemistry, 2008, vol. 6, # 7, p. 1251 - 1259

18
[ 873-76-7 ]
[ 73183-34-3 ]
[ 302348-51-2 ]

Reference： [1] RSC Advances, 2018, vol. 8, # 25, p. 13643 - 13648

19
[ 1692-25-7 ]
[ 873-76-7 ]
[ 127406-55-7 ]

Reference： [1] Dalton Transactions, 2014, vol. 43, # 26, p. 10235 - 10247

20
[ 5720-06-9 ]
[ 873-76-7 ]
[ 421553-62-0 ]

Reference： [1] Dalton Transactions, 2014, vol. 43, # 26, p. 10235 - 10247

21
[ 873-76-7 ]
[ 73183-34-3 ]
[ 517920-59-1 ]

Reference： [1] Organic Letters, 2017, vol. 19, # 5, p. 1204 - 1207

22
[ 873-76-7 ]
[ 375854-57-2 ]

Reference： [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 9, p. 1463 - 1467

23
[ 873-76-7 ]
[ 1268524-70-4 ]

Reference： [1] Patent: , 2016, ,

[ 873-76-7 ] Synthesis Path-Downstream 1~88

1
[ 98-86-2 ]
[ 873-76-7 ]
[ 5739-39-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With C16H14IrN2O3; caesium carbonate; In tert-Amyl alcohol; for 6h;Reflux;	Acetophenone (120mg, 1mmol), cat.1 (5.4mg, 0.01mmol, 1.0mol%), cesium carbonate (33mg, 0.1mmol,0.1equiv.), 4- chlorobenzyl alcohol (157mg, 1.1mmol) and tert-amyl alcohol (ImL) were sequentially added to a 5mL round bottomed flask. Anti-After the reaction mixture was refluxed for 6 hours in air, cooled to room temperature. The solvent is removed by rotary evaporation, then purified by column chromatography (developingSolvent: petroleum ether / ethyl acetate) to give the pure title compound Yield: 91%
86%	With potassium tert-butylate; In toluene; at 120℃;Inert atmosphere; Sealed tube;	Under protection of N2, a cobalt catalyst was added to a 100 ml hard glass tube(0.02 mmol, 2 mol%) and potassium tert-butoxide(11.2 mg, 0.10 mmol, 10 mol%),Then 5 ml of toluene was added and the magnet was stirred.Thereafter, 4-chlorobenzyl alcohol (156.2 mg, 1.1 mmol) andBenzophenone (120.0 mg, 1.0 mmol). Seal the glass tube in the oil bathHeat to 120 C and stir overnight. After 24 hours reaction cooled to room temperature,The solvent was distilled off under reduced pressure and the crude product was separated on a silica gel column(Eluent: ethyl acetate / hexane: 1: 5). Yield: 211 mg (86%).
86%	With potassium tert-butylate; In toluene; at 110 - 120℃; for 24h;Inert atmosphere;	Under the protection of N2, add a iron complex catalyst (0.02 mmol, 2 mol%) and potassium tert-butoxide (11.2 mg, 0.10 mmol, 10 mol%) into a 100 ml rigid flask, then add 5 ml of toluene and stir by magnetic . Thereafter, 4-chlorobenzyl alcohol (156.2 mg, 1.1 mmol) and benzophenone (120.0 mg, 1.0 mmol) were added. The flask was heated to reflux (110-120 C) in an oil bath and stirred overnight. After reacting for 24 hours, it was cooled to room temperature, the solvent was distilled under reduced pressure, and the crude product was separated through a silica gel column to obtain 1-phenyl-3- (4-chlorophenyl)-1-acetone. Yield: 211 mg (86%).

82%	With C38H36Cl4Ir2N4; caesium carbonate; In tert-Amyl alcohol; for 12h;Reflux;	A mixture of acetophenone (60 mg, 1 mmol),Cat. [Ir] (5.4 mg, 0.005 mmol, 1.0 mol%),Cesium carbonate (33 mg, 0.1 mmol, 0.2 equiv.),4-chlorobenzyl alcohol (86 mg, 0.6 mmol)And tert-amyl alcohol (1 mL) were successively added to a 5 mL round bottom flask.The reaction mixture was refluxed in air for 12 hours,Cool to room temperature.Rotate the solvent to remove the solvent,And then passed through a column chromatography (developing solvent:Petroleum ether / ethyl acetate) to give the pure title compound,Yield: 82%
81%	With C52H43Cl2IrN2P2; sodium hydroxide; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	General procedure: To a solution of Ir(III) complex (0.02 mmol) and base (1.0 mmol) in solution (3 mL) was added the corresponding ketone (1.0 mmol) and alcohol (2.0 mmol) under nitrogen. The reaction mixture was then placed in an oil bath and heated at 110 C for 12 h, cooled and quenched with water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate, then the combined organic layers were washed with water, dried over MgSO4, filtered, and the solvent was removed on a rotary evaporator. The resulting residue was purified by flash chromatography on silica gel using suitable mixtures of hexane/ethyl acetate as eluent. The products were characterized by comparing their m.p., IR and 1 H NMR spectra with those found in the literature [8], [12], [15], [32] and [33].
79%	With [Ru(eta6-p-cymene)Cl2]2; caesium carbonate; 2-((diphenylphosphino)amido)pyridine; In toluene; at 120℃; for 18h;Schlenk technique; Inert atmosphere;	General procedure: Cs2CO3 (0.6 mmol,195.6 mg) and toluene (1 mL) were added to a Schlenk tube under a N2 atmosphere. [RuCl2(eta6-p-cymene)]2 (0.005 mmol, 3.1 mg), L1 (0.01 mmol, 2.8 mg), alcohols (1.1 mmol) and ketones (1.0 mmol) were added in that order and the Schlenk tube was closed and stirred at 120C for 18 h. The reaction mixture was cooled to room temperature, quenched with water and extracted with ethyl acetate (20 mL x 3). The combined extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. The product was purified by column chromatography using petroleum ether/ethyl acetate as eluent to give the corresponding product (Figs. S22-S47 in Supporting Information).

Reference： [1]ACS Catalysis,2020,vol. 10,p. 3640 - 3649
[2]Journal of Organic Chemistry,2018,vol. 83,p. 2875 - 2881
[3]Patent: CN105439787,2016,A .Location in patent: Paragraph 0055; 0056; 0057; 0058; 0059
[4]ChemCatChem,2020,vol. 12,p. 3108 - 3125
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[8]Journal of Organic Chemistry,2015,vol. 80,p. 10769 - 10776
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[10]Dalton Transactions,2019,vol. 48,p. 13989 - 13999
[11]Patent: CN110423190,2019,A .Location in patent: Paragraph 0016
[12]Patent: CN111499503,2020,A .Location in patent: Paragraph 0057-0061
[13]Organic Letters,2019,vol. 21,p. 8065 - 8070
[14]RSC Advances,2013,vol. 3,p. 7739 - 7742
[15]New Journal of Chemistry,2019,vol. 43,p. 14057 - 14065
[16]Journal of Organic Chemistry,2017,vol. 82,p. 1943 - 1950
[17]Patent: CN106478395,2017,A .Location in patent: Paragraph 0034; 0035; 0036; 0037; 0038
[18]Journal of Organometallic Chemistry,2012,vol. 700,p. 214 - 218
[19]Tetrahedron,2017,vol. 73,p. 2374 - 2381
[20]Green Chemistry,2018,vol. 20,p. 2571 - 2577
[21]Journal of Organic Chemistry,2018,vol. 83,p. 3657 - 3668
[22]Synlett,2007,p. 1877 - 1880
[23]European Journal of Organic Chemistry,2008,p. 4908 - 4914
[24]Green Chemistry,2018,vol. 20,p. 4210 - 4216
[25]Journal of the American Chemical Society,1956,vol. 78,p. 4950
[26]Organometallics,2019,vol. 38,p. 654 - 664
[27]New Journal of Chemistry,2020,vol. 44,p. 8697 - 8701

2
[ 873-76-7 ]
[ 622-95-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With phosphorus pentoxide; potassium bromide; In acetonitrile; at 20℃; for 0.416667h;	General procedure: To a mixture of alcohol (1 mmol) and KBr (1.5 mmol, 0.18 g) in acetonitrile (5 mL), P2O5 (1.5 mmol, 0.23 g) was added and the reaction was stirred at room temperature for the time specified in Table 3. After reaction completion (TLC or GC), the reaction mixture was filtered and the residue washed with ethyl acetate (3 × 8 mL). The combined organic layers were washed with water (10 mL) and dried over Na2SO4. The solvent was removed under reduced pressure to afford the corresponding product. If necessary, further purification was performed by column chromatography.
91%	With bromine; In acetonitrile; at 120℃; for 0.0833333h;Microwave irradiation;	General procedure: To a suspension of polymer-bound triphenylphosphine (1.2 mmol) in anhydrous acetonitrile (10 mL) were added iodine (1 mmol) and 1,6-hexanediol diol (1mmol). The reaction mixture was irradiated in microwave reactor at 120 C for 3 min. The reaction mixture was filtered over a filter paper and washed with chloroform.The filtrate was extracted with aqueous sodium thiosulfate solution and dried with anhydrous sodium sulfate.The reafter, solvent was removed under reduced pressure to obtain 6-iodohexan-1-ol (30) in 93%
74%	With phosphorus tribromide; In diethyl ether; at 0 - 20℃; for 22h;	(Step 1) To a solution of p-chlorobenzaldehyde (722 mg, 5.1 mmol) in MeOH (10 mL) was slowly added sodium borohydride (195 mg, 5.15 mmol) at 0 C, and then the mixture was stirred at room temperature for 24 h. The resulting mixture was diluted with water and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and concentrated. Purification of the residue by chromatography on silica gel (hexane/ethyl acetate = 2 : 1 as eluent) afforded p-chlorobenzyl alcohol (16) (0.70 g, 96% yield) as a colorless oil. (Step 2) To a solution of 16 (0.70 g, 4.9 mmol) in dry Et2O (10 mL) was slowly added phosphorus tribromide (0.88 mL, 9.4 mmol) at 0 C, and the mixture was stirred at room temperature for 22 h. The resulting mixture was cooled at 0 C, and quenched with water. The mixture was extracted with ethyl acetate and washed with water, before dried over sodium sulfate. The residue was purified by chromatography on silica gel (hexane as eluent) to obtain p-chlorobenzyl bromide (741 mg, 74% yield) as white solids. 1H NMR (400 MHz, CDCl3) delta 7.50-7.20 (4H, m, Ph), 4.46 (2H, s, CH2); 13C NMR (100 MHz, CDCl3) delta 136.2, 134.2, 130.3, 128.9, 32.4. Spectral data were consistent with those previously reported in the literature.21

	With phosphorus tribromide; In dichloromethane;	Step 1: 4-chlorobenzyl bromide To a suspension of 4-chlorobenzyl alcohol (14.26 g, 100 mmol) in CH2 Cl2 (40 mL) at ambient temperature was added added dropwise a solution of PBr3 in CH2 Cl2 (1.0M, 32 mL, 32 mmol). The reaction mixture was stirred for 72 hours at ambient temperature and then was poured slowly onto ice. The layers were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-chlorobenzyl bromide (19.76 g) as a colorless solid.
	With phosphorus tribromide; In dichloromethane;	Step 1. 4-chlorobenzyl bromide. To a suspension of 4-chlorobenzyl alcohol (14.26 g, 100 mmol) in CH2 Cl2 (40 mL) at ambient temperature was added added dropwise a solution of PBr3 in CH2 Cl2 (1.0M, 32 mL, 32 mmol). The reaction mixture was stirred for 72 hours at ambient temperature and then was poured slowly onto ice. The layers were separated and the organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give 4-chlorobenzyl bromide (19.76 g) as a colorless solid.
	With hydrogen bromide;	a) 100 ml of HBr (48%) were heated to 90 and treated portionwise with 1.43 g (0.01 mol) of 4-chlorobenzyl alcohol. The mixture was stirred for 1/4 hr. and then cooled to room temperature. The mixture was extracted with ethyl acetate and the organic phase was washed with water and saturated sodium chloride solution and dried over sodium sulfate. 1.82 g (88.6%) of 4-chloro-benzyl bromide were obtained as colorless crystals; m.p. 53-55.
	With hexabromoacetone; triphenylphosphine; In acetonitrile; at 40℃; for 1h;Inert atmosphere;	A mixture of alcohol (1.2 mmol) and triphenylphosphine (1.8 mmol) was stirred in dry acetonitrile (6 mL) for 15 min. Hexabromoacetone (0.6 mmol) was added and the stirring continued at 40 under a nitrogen atmosphere. Conversion of the alcohol into the bromide was followed by 1H NMR analysis on a sample previously quenched with cold water.
	With phosphorus tribromide; In dichloromethane; at 0 - 5℃; for 0.5h;	General procedure: Benzyl alcohols (1 equiv) were taken in RBF and dichloromethane as a solvent. This reaction allowed to stir below 5 C, then added drop by drop phosphorus tribromide (PBr3) (1 equiv). The progress of the reaction was monitored by TLC using ethyl acetate: hexane as a solvent system. After completion of the reaction, the reaction mass was poured on crushed ice. Ethyl acetate was added to the mixture and the organic layer was separated. The aqueous layer was extracted with 3 x 10 mL of ethyl acetate and the combined organic layers were dried over MgSO4. Solvent was removed under reduced pressure, and the benzyl bromides were sufficiently pure to use without further work up.
	With phosphorus tribromide; In diethyl ether; at 0℃; for 0.5h;	General procedure: To a stirred solution of alcohol 2 (1 mmol) in dry ether (10 mL)was added phosphorus tribromide (0.5 mL) dropwise at 0 C and the reaction mixture was stirred for 0.5 h. After completion of thereaction (TLC monitoring), the reaction mixture was carefullypoured over ice, and the aqueous phase was extracted with ether.The combined organic layers werewashed with NaHCO3 and water,followed by brine. Drying over Na2SO4 and evaporation of thesolvents under reduced pressure affords the desired benzyl bromide3 which was used without further purification.
	With N-butyl-4-methylpyridinium bromide; toluene-4-sulfonic acid; at 140℃; for 1h;Green chemistry;	General procedure: A mixture of 5 mmol alcohol, 5 mmol p-toluenesulphonic acid, 5 mmol 1-n-butyl-4-methylpyridinium bromide was heated in an oil bath with constant stirring to different temperatures (Table-2), the progress of the reactions monitored by GC after 0.5, 1.0, 1.5,2.5 and 5 h. In the GC experiments, aliquots of reaction mixture drawn, diluted with 1 mL of diethyl ether, solution filtered and GC recorded. After complete conversion as indicated by GC, 25 mL of n-hexane was added to precipitate out the ionic liquid. The filtrate on evaporation of the solvent afforded the bromides, which could be identified by running GC with authentic sample. Products were examined for their purity by TLC using silica gel plates and n-hexane:petroleum ether (40-60) (9:1) as the eluent.

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3
[ 1878-66-6 ]
[ 52449-43-1 ]
[ 1195-44-4 ]
[ 3395-81-1 ]
[ 104-88-1 ]
[ 873-76-7 ]

Reference： [1]Synthetic Communications,1990,vol. 20,p. 1843 - 1852

4
[ 603-35-0 ]
[ 873-76-7 ]
[ 1530-39-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649

5
[ 74124-79-1 ]
[ 873-76-7 ]
[ 65853-61-4 ]

Yield	Reaction Conditions	Operation in experiment
79.6%	With dmap; In dichloromethane; acetonitrile; at 20℃; for 6h;	Compound <strong>[74124-79-1]N,N'-disuccinimidyl carbonate</strong> 8 (2.5 g, 9.8 mmol) was added to a stirred solution of ^-chlorobenzyl alcohol 9 (1.39 g, 9.7 mmol) and 4- (dimethylamino)pyridine (0.596 g, 4.9 mmol) in a solvent mixture of acetonitrile (15 mL) and dichloromethane (15 mL) at 20 C. After 6 h, the mixture was diluted with water (15 mL) and brine (5 mL). The resulting mixture was extracted with dichloromethane (30 mL) and washed with brine. The extract was dried over Na2S04, and evaporated. A white solid was obtained, which was triturated with ether and filtered. Yield = 2.2 g (79.6 %). NMR (400 MHz, CDC13): delta 7.36 (m, 4H), 5.25 (s, 2H), 2.82 (s, 4H).
78%	With dmap; In dichloromethane; acetonitrile; at 20℃; for 2h;	To a solution of (4-chlorophenyl)methanol (2.00 g, 14.03 mmol) in DCM/MeCN (1 : 1, 20 mL) was added bis(2,5-dioxopyrrolidin-l-yl) carbonate (3.59 g, 14.03 mmol) and DMAP (858 mg, 7.02 mmol) at ice-bath temperature. The reaction mixture was slowly warmed to room temperature. After stirring for 2 hours, the mixture was concentrated under reduced pressure. The residue was dissolved in ethyl acetate, washed with brine, dried over sodium sulfate, and the organic phase was concentrated under reduced pressure. The concentrate was triturated with hexane/ethyl acetate (2: 1, v/v) to afford the compound as a white power (3.10 g, 78%). 1H NMR (400 MHz, CDCI3) delta 7.39-7.33 (m, 4H), 5.28 (s, 2H), 2.84 (s, 4H).
	With dmap; In dichloromethane; acetonitrile; at 20℃; for 2h;	To a stirred solution of of 4-chlorobenzyl alcohol (115 mg, 0.81 mmol) and bis-(2,5-dioxopyrrolidin-1-yl)carbonate (207 mg, 0.81 mmol) in acetonitrile (3.0 mL) and CH2CI2 (3.0 mL) was added 4-dimethylaminopyridine (49 mg, 0.40 mmol) and the mixture was stirred for 2 h at room temperature. N-((3,3-difluoropiperidin-4-yl)methyl)-[1,2,4]triazolo[4,3-a]pyrazin-8-amine trifluoroacetate salt (280 mg, 0.73 mmol) in MeCN (2 mL) and TEA (0.3 mL, 2.2 mmol) were added and the resulting mixture was stirred for 1 hour at room temperature. The mixture was then diluted with ethyl acetate (5 mL) and the organic phase was washed with water, brine, dried over anhydrous Na2504 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel (DCM/MeOH = 50/1) to afford the title compound as a pale yellow powder (190 mg, 59%). MS (ESI) calcd for C19H19C1F2N602: 436.1, 438.1; found: 437.4, 439.4 [M+H]. 1H NMR (400 MHz, CD3OD) 6 9.08 (s, 1H), 7.69 (d, J = 4.8 Hz, 1H), 7.39-7.33 (m, 4H), 7.32 (d, J = 4.8 Hz, 1H), 5.16-5.09 (m, 2H), 4.37-4.26 (m, 1H), 4.19-4.11 (m, 1H), 4.01-3.95 (m, 1H), 3.65-3.57 (m, 1H),3.27-3.07 (m, 1H), 3.07-2.88 (m, 1H), 2.65-2.47 (m, 1H), 1.99-1.91 (m, 1H), 1.63-1.49 (m, 1H).

Reference： [1]Patent: WO2011/75537,2011,A1 .Location in patent: Page/Page column 80
[2]Patent: WO2018/98128,2018,A1 .Location in patent: Paragraph 0412
[3]Chemical and Pharmaceutical Bulletin,1990,vol. 38,p. 110 - 115
[4]Journal of Medicinal Chemistry,2001,vol. 44,p. 4468 - 4474
[5]Patent: WO2016/196513,2016,A1 .Location in patent: Paragraph 0234

6
[ 790-41-0 ]
[ 873-76-7 ]
[ 74-11-3 ]

Reference： [1]Synthesis,1987,p. 647 - 648

7
[ 39416-48-3 ]
[ 873-76-7 ]
C₇H₇ClO*C₅H₅N*Br₃H [ No CAS ]

Reference： [1]Journal of Chemical Research, Miniprint,1995,p. 1734 - 1758

8
C₇H₇ClO*C₅H₅N*Br₃H [ No CAS ]
[ 39416-48-3 ]
[ 873-76-7 ]

Reference： [1]Journal of Chemical Research, Miniprint,1995,p. 1734 - 1758

10
[ 42074-68-0 ]
[ 873-76-7 ]
[ 196814-73-0 ]
(S)-2-(2-Benzoyl-phenylamino)-3-[4-(4-chloro-benzyloxy)-phenyl]-propionic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1998,vol. 41,p. 5037 - 5054

11
[ 34117-90-3 ]
[ 873-76-7 ]
[ 251537-43-6 ]

Reference： [1]Acta poloniae pharmaceutica,1999,vol. 56,p. 201 - 206

12
[ 73152-41-7 ]
[ 144-62-7 ]
[ 873-76-7 ]
1-[4-(4-chloro-benzyloxy)-benzyl]-piperidine; compound with oxalic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2727 - 2736

13
[ 98-85-1 ]
[ 873-76-7 ]
[ 5739-39-9 ]
[ 62056-15-9 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4017 - 4019
[2]Green Chemistry,2010,vol. 12,p. 1362 - 1364
[3]Advanced Synthesis and Catalysis,2011,vol. 353,p. 2078 - 2084
[4]Organic and Biomolecular Chemistry,2016,vol. 14,p. 10988 - 10997
[5]Chemistry - A European Journal,2016,vol. 22,p. 18147 - 18155

14
[ 899426-20-1 ]
[ 16251-45-9 ]
[ 873-76-7 ]
3-methylsulafanyl-3-phenylpropan-1-ol [ No CAS ]

Reference： [1]Chemistry - A European Journal,2006,vol. 12,p. 3896 - 3904

15
[ 120-72-9 ]
[ 873-76-7 ]
[ 53541-89-2 ]
[ 178946-89-9 ]

Reference： [1]Organic Letters,2007,vol. 9,p. 3299 - 3302

16
[ 873-76-7 ]
[ 831-81-2 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 4875 - 4878
[2]Synlett,2014,vol. 25,p. 2928 - 2932

17
[ 873-76-7 ]
[-(CH₂)2-NH-(CH₂)3-N-]-CO₂-CH₂-Wang resin [ No CAS ]
[ 1530-39-8 ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 1007 - 1017

18
[ 873-76-7 ]
[ 1530-39-8 ]

Reference： [1]Journal of Organic Chemistry,1993,vol. 58,p. 5643 - 5649

19
[ 790-41-0 ]
curvularin [ No CAS ]
[ 873-76-7 ]

Reference： [1]Synthesis,1987,p. 647 - 648

20
[ 80875-98-5 ]
[ 873-76-7 ]
(2S,3aS,7aS)-octahydroindole-2-carboxylic acid-4-chlorophenylmethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		2S,3aS,7aS-Octahydroindole-2-carboxylic acid (50 gm) (0.3 mole), 4-chlorobenzyl alcohol (46.37 gm) (0.33 mol), p-toluene sulfonic acid (67.52 gm) (0.35 mol), and toluene (400 ml) were heated to reflux temperature and water removed azeotropically. The contents were cooled and water (100ml) was added and stirred for 15 minutes. The lower aqueous layer was discarded and the toluene was distilled under vacuum at 60C to get an oil. Diisopropyl ether (200 ml) was added to the residue and stirred at room temp. The solids were filtered and the wet cake was added to dichloromethane (500 ml) and aqueous ammonia (60 ml) was added dropwise under stirring. The aqueous phase was separated and the organic phase washed with water till the washings were neutral. Dichloromethane was concentrated at 50C under vacuum to get oil (37.2 gm) which solidifies on standing.

Reference： [1]Patent: WO2005/100317,2005,A1 .Location in patent: Page/Page column 12

21
[ 7758-89-6 ]
[ 66-71-7 ]
[ 873-76-7 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; hydrazine; In toluene;	Following the procedure of Example 2 using hydrazine in toluene (12 ml, 1M), copper (I) chloride (12.5 mg), 1,10-phenanthroline (24 mg), potassium carbonate (0.7 g), and p-chlorobenzyl alcohol (0.36 g). The reaction was stirred at 80 C. and after 2 hours 1 H NMR analysis showed 100% conversion to the title compound.

Reference： [1]Patent: US5912388,1999,A

22
[ 7758-89-6 ]
[ 66-71-7 ]
[ 870-50-8 ]
[ 873-76-7 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
83%	With potassium carbonate; In toluene;	EXAMPLE 18 This Example illustrates the preparation of p-chlorobenzaldehyde. To a mixture of copper (I) chloride (1.98 g) and 1,10-phenanthroline (3.60 g) were added toluene (800 ml) and potassium carbonate (110 g). The resulting mixture was stirred for 30 minutes after which di-tert-butyl azodicarboxylate (4.60 g) and p-chlorobenzylalcohol (57.0 g) were added successively. The mixture was heated to 90 C. and oxygen gas was bubbled in for 1.5 hours. After cooling to room temperature the reaction mixture was diluted with diethyl ether (500 ml) and filtered through a pad of CELITE. The filtrate was washed successively with water (200 ml), 1N aqueous hydrochloric acid (200 ml) and brine (200 ml), dried over magnesium sulphate and evaporated in vacuo. The resulting residue was distilled to provide the title compound (46.5 g, 83% yield).

Reference： [1]Patent: US5912388,1999,A

23
[ 7758-89-6 ]
[ 66-71-7 ]
Å molecular sieves [ No CAS ]
di(tert-butyl) diazodicarboxylate [ No CAS ]
[ 873-76-7 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
99%	In diethyl ether; toluene;	EXAMPLE 17 This Example illustrates the preparation of p-chlorobenzaldehyde. <strong>[7758-89-6]Copper (I) chloride</strong> (10 mg) and 1,10-phenanthroline (18 mg) were suspended in toluene (5 ml). 4 A molecular sieves, di-tert-butyl diazodicarboxylate (0.276 g) and p-chlorobenzylalcohol (0.143 g) were added successively and the resulting mixture was stirred for 12 hours at room temperature whilst oxygen was bubbled in. After dilution with diethyl ether (10 ml), the reaction mixture was filtered and the filtrate evaporated in vacuo to leave the title compound in 99% yield and 100% conversion.

Reference： [1]Patent: US5912388,1999,A

24
[ 7758-89-6 ]
[ 66-71-7 ]
[ 4114-28-7 ]
[ 873-76-7 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium tert-butylate; In toluene;	EXAMPLE 1 This Example illustrates the preparation of p-chlorobenzaldehyde. To a stirred mixture of toluene (12 ml) and copper (I) chloride (12.5 mg) were added 1,10-phenanthroline (24 mg), powdered 4 A sieves (1 g, ex-Fluka, flame-dried), potassium tert-butoxide (0.28 g), 1,2-dicarbethoxyhydrazine (0.11 g) and p-chlorobenzyl alcohol (0.36 g). Oxygen was bubbled into the reaction mixture and the reaction mixture was stirred at 80 C. Ater 45 minutes at 80 C. analysis showed 100% conversion of p-chlorobenzyl alcohol to p-chlorobenzaldehyde.
	With hydrogenchloride; potassium carbonate; In toluene;	EXAMPLE 2 This Example illustrates the preparation of p-chlorobenzaldehyde. To a stirred mixture of toluene (600 ml) and copper (I) chloride (1.24 g) was added 1,10-phenanthroline (2.26 g). A complex was allowed to form, as a black-grey solid, before potassium carbonate (70 g) was added, followed by 1,2-dicarbethoxyhydrazine (11) and then p-chlorobenzyl alcohol (35.6 g). This was heated to 80-90 C. and gentle current of air was added via a sintered inlet. Aliquots of the solution were taken at intervals and analyzed by 1 H NMR spectroscopy. The reaction was judged to be complete at 5 h, and was allowed to cool. The crude reaction mixture was transferred to a 11 separating funnel and dilute hydrochloric acid was added slowly until the aqueous phase was acidic. The aqueous layer was extracted with toluene (2*100 ml); the combined organic layers washed with saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml) and dried (MgSO4). The solvent was evaporated to leave 34.1 g of a sticky black oil; purity of product (1 H NMR~85%). The residue was re-crystallized from ethanol-water (3:1) to give p-chlorobenzaldehyde.
	With potassium tert-butylate; In toluene;	EXAMPLE 15 This Example illustrates the preparation of p-chlorobenzaldehyde. <strong>[7758-89-6]Copper (I) chloride</strong> (12.5 mg) and 1,10-phenanthroline (24 mg) were suspended in toluene (12 ml) in a flask equipped with a Dean and Stark apparatus. 1,2-Dicarbethoxyhydrazine (0.11 g), potassium tert-butoxide (28 mg) and p-chlorobenzylalcohol (0.36 g) were then added to the reaction mixture. Oxygen was bubbled into the mixture and the mixture was stirred at reflux. 1 H NMR analysis of the reaction mixture showed 100% conversion to the title compound after 3 hours.

Reference： [1]Patent: US5912388,1999,A
[2]Patent: US5912388,1999,A
[3]Patent: US5912388,1999,A

25
[ 7758-89-6 ]
diethyl diazodicarboxylate [ No CAS ]
[ 873-76-7 ]
[ 104-88-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In toluene;	EXAMPLE 16 This Example illustrates the preparation of p-chlorobenzaldehyde. <strong>[7758-89-6]Copper (I) chloride</strong> (12.5 mg) and 1,10-phenantliroline (24 mg) were suspended in toluene (12 ml). Potassium carbonate (0.7 g), diethyl diazodicarboxylate (0.11 g) and p-chlorobenzylalcohol (0.36 g) were added sequentially to the reaction mixture. Oxygen was bubbled into the mixture and the mixture was stirred at reflux. 1 H NMR analysis of the reaction mixture showed 100% conversion to the title compound after 0.5 hours.

Reference： [1]Patent: US5912388,1999,A

26
[ 63624-48-6 ]
[ 85-81-4 ]
[ 52824-29-0 ]
[ 68-12-2 ]
[ 873-76-7 ]
[ 63624-56-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; hydrazine hydrate; hydroquinone;aluminum nickel; In ethanol; toluene;	A. 8-Amino-2-(4-chlorobenzyloxy)-6-methoxyquinoline. 6-Methoxy-8-nitroquinoline was converted into 2-chloro-<strong>[85-81-4]6-methoxy-8-nitroquinoline</strong>: K. Mislow and J. B. Koepfli, J. Amer. Chem. Soc., 68, 1553 (1946); R. E. Lyle, et al., J. Org. Chem., 37, 3967 (1972). A mixture of 48 g (0.2 mole) of 2-chloro-<strong>[85-81-4]6-methoxy-8-nitroquinoline</strong>, 42.78 g (0.3 mole) of 4-chlorobenzyl alcohol, 27.6 g (0.2 mole) of anhydrous potassium carbonate, and 200 ml N,N-dimethyl formamide was heated under nitrogen at ca. 155-160 for 18 hr. The mixture was cooled, diluted with ice water, stirred, collected, and washed with water. The crude solid was leached with a little 95% ethanol at 70 and then recrystallized from that solvent. A 84% yield of 2-(4-chlorobenzyloxy)-<strong>[85-81-4]6-methoxy-8-nitroquinoline</strong> resulted; mp 129.5-133.5. The foregoing nitro compound (34.48 g, 0.1 mole), 500 ml of a 1:1 mixture (v/v) of toluene and ethanol, 10 g wet Raney nickel, and 50 ml 85% hydrazine hydrate was refluxed for 6 hr. Thereafter, the condenser was placed for distillation and heated until vapors at the still-head were alkaline. A small amount of hydroquinone was added, and the hot mixture filtered. The filtrates were concentrated in vacuo, leached with a little warm ethanol, then crystallized from ethanol (charcoal). The 8-amino-2-(4-chlorobenzyloxy)-6-methoxyquinoline was obtained in 97% yield; mp 123.5-125.

Reference： [1]Patent: US4167638,1979,A

27
[ 5451-09-2 ]
[ 873-76-7 ]
[ 396078-83-4 ]

Yield	Reaction Conditions	Operation in experiment
0.56 g (32%)		4-Chlorobenzyl 5-amino-4-oxopentanoate Hydrochloride [Compound 19] From 4-chlorobenzyl alcohol (5.0 g; 35 mmol) and <strong>[5451-09-2]5-amino-4-oxopentanoic acid hydrochloride</strong> (1.0 g; 6.0 mmol). The reaction was complete after 24 h at 100 C. The yield was 0.56 g (32%). Mp 127-129 C. 1H NMR (200 MHz; DMSO-d6): delta 2.65 (2H, t, J=5.8 Hz), 2.89 (2H, t, J=6.0 Hz), 3.99 (2H, br s), 5.11 (2H, s), 7.44 (4H, s), 8.56 (3H, br s). 13C NMR (50 MHz; DMSO-d6): delta 27.1, 34.3, 46.5, 64.7, 128.4, 129.7, 132.6, 135.1, 171.8, 202.5.

Reference： [1]Patent: US2004/106679,2004,A1

28
[ 1126-46-1 ]
[ 4068-78-4 ]
[ 22717-55-1 ]
[ 873-76-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 1251 - 1259

29
[ 592-35-8 ]
[ 873-76-7 ]
[ 1158827-11-2 ]

Reference： [1]Tetrahedron,2009,vol. 65,p. 3624 - 3628

30
[ 1121-76-2 ]
[ 873-76-7 ]
[ 924311-88-6 ]

Yield	Reaction Conditions	Operation in experiment
66%		A solution of (4-chloropheny)methanol (49.5 g, 347 mmol) inTHF (200 mL) was added dropwise to a suspension of NaH (60%oil dispersion, 16.7 g, 419 mmol) in THF (200 mL) at 0 C. Afterthe mixture was stirred at 0 C for 30 min, 4 (45.0 g, 347 mmol)was added portionwise to the reaction mixture. After completionof the addition, the mixture was stirred at rt for 5 h. The mixturewas quenched with water (400 mL) at 0 C and extracted withEtOAc/THF (1:1) four times. The organic layers were combined,passed through NH-silica gel pad (EtOAc/MeOH) and concentrated.The filtrate was concentrated, and the residual solid was washedwith IPE and dried to give the title compound (54.3 g, 66%) as abrown solid. 1H NMR (400 MHz, CDCl3) d 5.17 (2H, s), 7.08 (2H,d, J = 6.9 Hz), 7.48 (4H, s), 8.10 (2H, d, J = 7.0 Hz). MS (ESI/APCI)m/z 236.0 [M+H]+.
47%		4-Chlorobenzylalcohol (5.0 g, 35 mmol) was dissolved in DMF (25 mL) and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After stirring for 30 minutes, 4-chloropyridine-iV-oxide (2.27 g, 17.5 mmol) was added and the reaction mixture was heated for 1 h at 120 0C. Upon cooling, the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5chi), dried and concentrated. Purification by flash column chromatography (12 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 25 mL/min) provided the title compound (1.9 g, 47%) as an orange solid: 1H NMR (300 MHz, CDCl3) delta 8.11 (d, J = 7.7 Hz, 2H), 7.40 (d, J= 8.6 Hz, 2H), 7.34 (d, J= 8.6 Hz, 2H), 6.86 (d, J= 7.7 Hz, 2H), 5.06 (s, 2H).
40%	With Tris(3,6-dioxaheptyl)amine; potassium carbonate; potassium hydroxide; In toluene; for 3h;Reflux;	4-(4-Chloro-benzyloxy)-py?dine-N-oxide: To a suspension of powdered potassium hydroxide (7.60 g, 136 mmol) and potassium carbonate (4.70 g, 34.1 mmol) in dry toluene were added (4-chloro-phenyl)-methanol (7.26 g, 50.9 mmol), 4-chloropyridinc-N-oxide (4.39 g, 34.0 mmol) and TDA-I (1.10 mL, 3.44 mmol). After the mixture was heated at reflux for 3 hours, the organic layer was separated and dried over anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified through a silica gel column to give 4-(4-chloro-benzyloxy)-pyridine-N-oxide in 40% yield as light yellowish solid. 1H NMR (CDCl1) 5: 8.13 (m, 2H), 7.37 (m, 4H), 6.85 (m, 2H), 5.06 (s, 2H); ESMS m/e: 235.9 (M+H)+.

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 1116 - 1139
[2]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 2504 - 2518
[3]Patent: WO2009/89482,2009,A1 .Location in patent: Page/Page column 83
[4]Patent: WO2009/120655,2009,A1 .Location in patent: Page/Page column 32-33
[5]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 5851 - 5856

31
[ 32675-71-1 ]
[ 873-76-7 ]
[ 1194630-02-8 ]

Reference： [1]Angewandte Chemie - International Edition,2009,vol. 48,p. 7025 - 7029
Angewandte Chemie,2009,vol. 121,p. 7159 - 7163

32
[ 1312588-22-9 ]
[ 108-67-8 ]
[ 93-58-3 ]
[ 5779-95-3 ]
[ 2446-51-7 ]
[ 27129-87-9 ]
[ 64583-55-7 ]
[ 2745-54-2 ]
[ 20386-93-0 ]
[ 104-88-1 ]
[ 55-21-0 ]
[ 873-76-7 ]

Reference： [1]Organic and Biomolecular Chemistry,2011,vol. 9,p. 4116 - 4126

33
[ 109-12-6 ]
[ 873-76-7 ]
[ 23676-57-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With C41H36AsClN3OPRuS; potassium hydroxide; In toluene; at 100℃; for 12h;	General procedure: Amine/sulfonamide (1mmol), alcohol (1mmol), catalyst (0.5mol %), KOH (50mol %) and toluene (2mL) were placed in a 25mL round bottomed flask and stirred on a preheated oil bath (100C) for 12h. Upon completion (as monitored by TLC), the reaction mixture was cooled at ambient temperature, H2O (3mL) was added and the organic layer was extracted with CH2Cl2. The organic extract was separated, dried, and concentrated. The desired product was purified by column chromatography with n-hexane/EtOAc as eluent.
95%	With C51H40Cl2N2O3P2Ru; potassium hydroxide; In toluene; at 120℃; for 14h;	General procedure: 0.5 mol% ruthenium(II) catalyst was stirred with 4 mmol ofKOH in toluene. To this mixture, 2 mmol of alcohol and 2 mmolof amine were added and the temperature was raised up to120 C. The progress of the reactions was monitored using TLC.As soon as the reaction was completed, the mixture was cooledto room temperature and added 3 mL of distilled water. The combinedmixture was extracted with CH2Cl2 and dried by addingmagnesium sulfate. The crude product was purified by columnchromatography (n-hexane/EtOAc) and characterized by 1H NMRspectral analyses. The 1H NMR data obtained for the catalytic productswere compared with literature [19].

Reference： [1]Dalton Transactions,2014,vol. 43,p. 7889 - 7902
[2]RSC Advances,2015,vol. 5,p. 11405 - 11422
[3]Journal of Organometallic Chemistry,2015,vol. 791,p. 130 - 140
[4]Inorganica Chimica Acta,2015,vol. 427,p. 203 - 210
[5]Journal of Organic Chemistry,2013,vol. 78,p. 6775 - 6781
[6]Green Chemistry,2015,vol. 17,p. 3260 - 3265
[7]Journal of Organic Chemistry,2020,vol. 85,p. 7125 - 7135
[8]Advanced Synthesis and Catalysis,2013,vol. 355,p. 73 - 80
[9]Organic Letters,2011,vol. 13,p. 6184 - 6187

34
[ 68-12-2 ]
[ 873-76-7 ]
[ 14062-80-7 ]

Yield	Reaction Conditions	Operation in experiment
87%	With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide; In 1,1,2-trichloroethane; water; at 90℃; for 12h;	General procedure: To a solution of alcohols 1 (0.1 mmol) in TCE (1.0 mL) was added n-Bu4NI (20 mol%) and N, N-disubstituted formamides 2 (0.5 mmol), followed by adding a solution of TBHP (6.0 equiv., 70% aqueous solution). The resulting mixture was stirred at 90 oC until it completed. When the reaction was finished, the reaction mixture was cooled to room temperature and poured into saturated Na2S2O3 solution (3.0 mL), extracted with EtOAc (3×8.0 mL), then washed with saturated brine. The combined organic layers were dried over anhydrous Na2SO4. After removing the solvents in vacuo, the residue was purified by flash column chromatography on silica gel or preparative TLC on GF 254 to afford the desired products 3.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 6479 - 6482,4
[2]Chemistry - A European Journal,2012,vol. 18,p. 9793 - 9797
[3]Applied Organometallic Chemistry,2019,vol. 33
[4]Inorganic Chemistry,2017,vol. 56,p. 10596 - 10608

35
[ 1006-39-9 ]
[ 873-76-7 ]
[ 1401031-99-9 ]

Yield	Reaction Conditions	Operation in experiment
67%	With di-tert-butyl peroxide; copper(l) chloride; at 120℃; for 6h;	General procedure: 2'-Bromoacetophenone (1a) (100.0 mg, 0.5mmol), benzyl alcohol (5a) (325.0mg,1.5mmol), CuCl (5.0mg, 0.05mmol), DTBP (365.0mg, 1.25 mmol), and 25% aqueous ammonia (0.5 mL) were placed in a thick-walled Pyrex screw-captube(25mL), and the tube was capped and the mixture heated in an oil bath at 120 C with stirring for 6 h. After the reaction mixture was cooled to room temperature, the workup and isolation of the products were essentially similar to the procedure above-mentioned. Compound 3a was obtained as white solid in 65% (71.5 mg, 0.33 mmol), and the GC analysis of the reaction mixture disclosed the formation of 3a in 66% GC yield.

Reference： [1]Tetrahedron,2012,vol. 68,p. 9364 - 9370

36
[ 873-76-7 ]
[ 837-18-3 ]

Reference： [1]Chinese Journal of Chemistry,2012,vol. 30,p. 2322 - 2332,11

37
[ 120-72-9 ]
[ 873-76-7 ]
[ 178946-89-9 ]

Reference： [1]Letters in Organic Chemistry,2013,vol. 10,p. 111 - 117
[2]Synlett,2012,vol. 23,p. 2975 - 2979
[3]European Journal of Organic Chemistry,2013,p. 6344 - 6354

38
[ 6318-74-7 ]
[ 873-76-7 ]
N-(4-chlorobenzyl)-4,5-diphenylthiazol-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With C39H34CuN3P2S; potassium hydroxide; In toluene; at 100℃; for 12h;	General procedure: In a 25 mL round bottomed flask were placed 0.1 mol % of copper(I) catalyst, 1 mmol of alcohol, 1 mmol of amine, 0.2 mmol of KOH and 2 mL of toluene. The reaction flask was heated at 100 C for 12 h in an oil bath. Upon completion (as monitored by TLC), the reaction mixture was cooled at ambient temperature, H2O (3 mL) was added and the organic layer was extracted with CH2Cl2 (3 10 mL). The combined organic layers were dried with magnesium sulphate and concentrated. The crude product was purified by column chromatography (ethyl acetate/hexane). Reported isolated yields are an average of two runs

Reference： [1]Inorganica Chimica Acta,2017,vol. 464,p. 88 - 93
[2]Journal of Organic Chemistry,2013,vol. 78,p. 6775 - 6781

39
[ 4249-72-3 ]
[ 873-76-7 ]
[ 5739-39-9 ]

Reference： [1]ChemCatChem,2013,vol. 5,p. 2170 - 2173

40
potassium cyanide [ No CAS ]
[ 873-76-7 ]
[ 874-89-5 ]

Reference： [1]Organometallics,2013,vol. 32,p. 3537 - 3543

41
potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
[ 873-76-7 ]
[ 874-89-5 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 10035 - 10039
Angew. Chem.,2013,vol. 125,p. 10219 - 10223

42
[ 98-85-1 ]
[ 873-76-7 ]
[ 5739-39-9 ]

Yield	Reaction Conditions	Operation in experiment
88%		DL-1-phenylethanol (122 mg, 1.0 mmol), cat. [Ir] (5.3 mg, 0.01 mmol, 1 mol%) and tert-amyl alcohol (1 mL) were successively added to a 5 mL round bottom flask. The reaction mixture was refluxed in air for 6 hours and then cooled to room temperature. Then, cesium carbonate (33 mg, 0.1 mmol, 0.1 equiv.) And 4-chlorobenzyl alcohol (157 mg, 1.1 mmol) were added, refluxed in air for 6 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and then the title compound was obtained by column chromatography (developing solvent: petroleum ether / ethyl acetate) in a yield of 88%
75%	With [Co(N,N'-bis(alpha-pyridyl)-2,6-diaminopyridine)Cl2]; sodium hydroxide; In toluene; at 120℃; for 24h;Inert atmosphere; Molecular sieve; Schlenk technique;	General procedure: Under an N2 atmosphere, a mixture of secondary alcohol (0.5 mmol), primary alcohol (0.6 mmol), 1a (5 mol %), NaOH (0.1 mmol), 4 A molecular sieve (0.6 g), and toluene (1.5 mL) was added into a 25 mL Schlenk tube equipped with a stirring bar. The mixture was heated to 120 C under a slow and steady N2 flow for 24 h. After cooling to ambient temperature, 6 mL water was added and the aqueous solution extracted with ethyl acetate (3 x 5 mL). The combined extracts were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The crude product purified on a short flash chromatography column.

Reference： [1]RSC Advances,2016,vol. 6,p. 24164 - 24174
[2]Advanced Synthesis and Catalysis,2013,vol. 355,p. 3077 - 3080
[3]ChemSusChem,2019,vol. 12,p. 4693 - 4699
[4]ACS Catalysis,2014,vol. 4,p. 3910 - 3918
[5]Patent: CN106478325,2017,A .Location in patent: Paragraph 0063; 0064; 0065; 0066; 0067
[6]ChemSusChem,2013,vol. 6,p. 604 - 608
[7]Organic and Biomolecular Chemistry,2019,vol. 17,p. 3567 - 3574
[8]ChemSusChem,2020,vol. 13,p. 2557 - 2563
[9]Tetrahedron,2019,vol. 75
[10]Journal of Organic Chemistry,2018,vol. 83,p. 2875 - 2881
[11]ACS Catalysis,2018,vol. 8,p. 10300 - 10305
[12]Organic and Biomolecular Chemistry,2017,vol. 15,p. 3466 - 3471

43
[ 117570-53-3 ]
[ 873-76-7 ]
[ 1415113-23-3 ]

Reference： [1]MedChemComm,2014,vol. 5,p. 512 - 520

44
[ 3470-50-6 ]
[ 873-76-7 ]
[ 88628-47-1 ]

Yield	Reaction Conditions	Operation in experiment
78%	With potassium carbonate; In acetone; for 6h;Reflux;	General procedure: <strong>[3470-50-6]6-Hydroxy-1-tetralone</strong> (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70 mmol). The reaction was treated with an appropriately substituted arylalkyl bromide (2.035 mmol) and heated under reflux for 6 h. The reaction progress was monitored using silica gel TLC with ethyl acetate:petroleum ether (1:2) as mobile phase. Upon completion, the reaction was filtered through a pad of celite and concentrated in vacuo. The crude thus obtained was purified by recrystallization from cyclohexane.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 2758 - 2763

45
[ 5720-07-0 ]
[ 873-76-7 ]
[ 52988-34-8 ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 10235 - 10247

46
[ 5720-06-9 ]
[ 873-76-7 ]
[ 421553-62-0 ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 10235 - 10247

47
[ 1692-25-7 ]
[ 873-76-7 ]
[ 127406-55-7 ]

Reference： [1]Dalton Transactions,2014,vol. 43,p. 10235 - 10247

48
[ 2002-24-6 ]
[ 873-76-7 ]
[ 7400-54-6 ]

Reference： [1]Tetrahedron,2014,vol. 70,p. 5093 - 5099

49
[ 108-86-1 ]
[ 873-76-7 ]
[ 831-81-2 ]

Reference： [1]Chemical Science,2015,vol. 6,p. 1115 - 1119

50
[ 38980-96-0 ]
[ 873-76-7 ]
2-(4-chlorophenyl)-4,6-bis(4-(trifluoromethyl)phenyl)-1,3,5-triazine [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 6723 - 6727

51
[ 66230-04-4 ]
[ 1745-18-2 ]
[ 622-98-0 ]
[ 1875-88-3 ]
[ 2012-74-0 ]
[ 23853-78-3 ]
[ 3739-38-6 ]
[ 938-95-4 ]
[ 39515-51-0 ]
[ 873-76-7 ]
methyl N-hydroxybenzene carboximidoate [ No CAS ]

Reference： [1]Journal of the Brazilian Chemical Society,2015,vol. 26,p. 1831 - 1837

52
[ 5754-35-8 ]
[ 873-76-7 ]
C₁₂H₁₇NO₃ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 11942 - 11945

53
[ 873-76-7 ]
[ 100-51-6 ]
[ 178946-89-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With lithium perchlorate; In acetonitrile; at 20℃;Electrochemical reaction;	General procedure: A 40 cm3 acetonitrile solution of alcohols 1a-1i(1 mmol) in LiClO4 (0.05 g) was electrolyzed at the2.0 V versus SCE. After completion of the electro-oxidationof alcohols to their corresponding aldehydes,indoles 2a, 2b (2 mmol) were added and electrolyzed at-0.9 V versus SCE. In the two mentioned stages, electrosynthesisreactions were done in an undivided cellequipped with graphite rods as the cathode and Pt-anodeat room temperature. The electrolysis was terminatedwhen the current decreased by more than 95 %. Amagnetic stirrer was employed during the electrolysis.The process was interrupted several times during theelectrolysis and the graphite rod was washed in acetonein order to reactivate it. After completion of the electrocondensation,the solvent was evaporated and theresulting crude product was purified by preparative thinlayerchromatography on silica gel (eluent: n-hexane-EtOAc, 4:1) to afford 3,30-di(indolyl)methanes 3a-3k.All the products were characterized by comparison oftheir melting points and also spectroscopic data (IR, 1HNMR and mass spectra) with those of the authenticsamples in literature

Reference： [1]Monatshefte fur Chemie,2015,vol. 146,p. 2021 - 2027

54
[ 98-86-2 ]
[ 873-76-7 ]
[ 5739-39-9 ]
[ 62056-15-9 ]

Reference： [1]Applied Organometallic Chemistry,2019,vol. 33
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 14483 - 14486
Angew. Chem.,2015,vol. 127,p. 14691 - 14694,4

55
[ 124-40-3 ]
[ 873-76-7 ]
[ 14062-80-7 ]

Yield	Reaction Conditions	Operation in experiment
88%	With tert.-butylhydroperoxide; [bis(acetoxy)iodo]benzene; In acetonitrile;Reflux;	General procedure: To a mixture of aryl alcohol (1.0 mmol), appropriate amine (2.5 mmol) and TBHP (70 wt % in H2O, 8.0 mmol) in acetonitrile (5 mL), was added DIB (0.2 mmol, 20 mol %) at room temperature. The reaction was allowed to stir at reflux temperature for 5-6 h. After the reaction was complete, as indicated by TLC, the mixture was cooled to room temperature. The volatiles were removed under reduced pressure and 10 mL saturated solution of NaHCO3 was added. The mixture was extracted with ethylacetate (310 mL). The combined organic phases were dried with Na2SO4 and evaporated under vacuum. Purification of the residue by column chromatography (petroleum ether/EtOAc) afforded the desired amide.

Reference： [1]Tetrahedron Letters,2015,vol. 56,p. 6768 - 6771

56
[ 873-76-7 ]
[ 19500-02-8 ]
(E)-N-(4-chlorobenzylidene)-3-methoxy-2-methylaniline [ No CAS ]

Reference： [1]Green Chemistry,2016,vol. 18,p. 3232 - 3238

57
[ 1532-71-4 ]
[ 873-76-7 ]
[ 16576-24-2 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With ammonium cerium (IV) nitrate; bis(tricyclohexylphosphine)nickel(II) dichloride; 2,2-bis(hydroxymethyl)propionic acid; strontium nitrate; cadmium(II) acetate; In ethylene glycol; at 70℃; for 8h;Inert atmosphere;	Under room temperature, the nitrogen atmosphere, to the proper amount of organic solvent glycol, by adding 100mmol compounds represented by the following general formula (I) compound, 150mmol aboving (II) compound, 12mmol catalyst NiCl 2 (PCy 3) 2, 200mmol oxidant ammonium ceric nitrate, 175mmol alkali DMPA and 15mmol promoter (for 3mmol cadmium acetate and 12mmol strontium nitrate of mixture), then heating to 70 °C, and at this temperature the stirring reaction 8 hours; After the reaction, the reaction solution is filtered, adjusted to neutral pH value of the filtrate, saturated salt water is then used to fully wash, then adding ethyl acetate extraction 2-3 time, combined with the phase, drying anhydrous sodium sulfate, concentrated under reduced pressure, the resulting residue over silica gel column chromatography, so as to the acetone and volume ratio of the mixed solution of petroleum ether eluviation, so as to obtain the compound of formula (III), the yield is 95.4percent.

Reference： [1]Patent: CN105481768,2016,A .Location in patent: Paragraph 0039; 0040; 0041; 0042; 0043

58
[ 873-76-7 ]
[ 1268524-70-4 ]

Reference： [1]Patent: ,2016,

59
[ 873-76-7 ]
[ 50508-66-2 ]

Reference： [1]Patent: ,2016,

60
[ 1115-70-4 ]
[ 873-76-7 ]
[ 43153-46-4 ]

Reference： [1]New Journal of Chemistry,2016,vol. 40,p. 8225 - 8228

61
[ 536-74-3 ]
[ 873-76-7 ]
[ 5739-39-9 ]

Yield	Reaction Conditions	Operation in experiment
87%		The [(IPr) AuCl] (6mg, 0.01mmol, 1mol%), AgOTf (2.6mg, 0.01mmol, 1mol%), phenylacetylene (102mg, 1mmol), 1,4- dioxane (1ml) and water (36ul, 2equiv.) were successively added to 5ml microwave tube.After the reaction mixture was microwaved at 120 reactor for one hour, cooled to room temperature.Thereto was added [Cp * IrCl2]2(8mg, 0.01mmol, 1mol%), potassium tert-butoxide (34mg, 0.3mmol, 0.3equiv.), 4- chlorobenzyl alcohol (171mg, 1.2mmol).After the reaction mixture was microwaved at 130 reactor and then reacted for 2 hours, cooled to room temperature.Filtered, and solvent was removed by rotary evaporation, then purified by column chromatography (developing solvent: petroleum ether / ethyl acetate) to give the pure title compound Yield: 87%

Reference： [1]Patent: CN104557500,2016,B .Location in patent: Paragraph 0056; 0057; 0058; 0059

62
[ 17672-21-8 ]
[ 873-76-7 ]
C₁₅H₁₄ClNO₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 295 - 298

63
[ 674792-04-2 ]
[ 873-76-7 ]
tert-butyl (R)-4-(4-chlorobenzoyl)-2-isopropylpiperazine-1-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 10688 - 10697

64
[ 657-36-3 ]
[ 873-76-7 ]
(4-chlorophenyl)(4-(trifluoromethyl)piperidin-1-yl)methanone [ No CAS ]
[ 74-11-3 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 10688 - 10697

65
[ 657-36-3 ]
[ 873-76-7 ]
(4-chlorophenyl)(4-(trifluoromethyl)piperidin-1-yl)methanone [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 10688 - 10697

66
[ 873-76-7 ]
[ 138007-24-6 ]
tert-butyl 1-(4-chlorobenzoyl)piperidine-4-carboxylate [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 10688 - 10697

67
[ 873-76-7 ]
[ 16687-61-9 ]

Reference： [1]Journal of Chemical Research,2017,vol. 41,p. 25 - 29

68
[ 873-76-7 ]
[ 790-41-0 ]

Reference： [1]New Journal of Chemistry,2017,vol. 41,p. 931 - 939
[2]Tetrahedron Letters,2017,vol. 58,p. 2533 - 2536

69
[ 873-76-7 ]
[ 73183-34-3 ]
[ 517920-59-1 ]

Reference： [1]Organic Letters,2017,vol. 19,p. 1204 - 1207

70
[ 873-76-7 ]
[ 19641-29-3 ]

Reference： [1]Green Chemistry,2017,vol. 19,p. 2501 - 2505

71
[ 15754-51-5 ]
[ 873-76-7 ]
bis(4-methoxyphenyl)oxophosphinyl(4-chlorophenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dipotassium peroxodisulfate; In acetone; at 20℃;	(1) 4-Chlorobenzyl alcohol (0.114 g, 0.8 mmol) was added to the reaction flask,(4-methoxyphenyl) phosphine oxide (0.314 g, 1.2 mmol)Potassium persulfate (0.648 g, 2.4 mmol) and acetone (2 mL)Room temperature reaction; (2) TLC tracking reaction until complete; (3) The crude product obtained after the completion of the reaction was separated by column chromatography (dichloromethane: methanol = 40: 1) to give the desired product(Yield 87%).

Reference： [1]Patent: CN106496268,2017,A .Location in patent: Paragraph 0017

72
[ 14188-94-4 ]
[ 873-76-7 ]
5-acetyl-2-(4-chlorobenzoyl)pyridine 1-oxide [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2017,vol. 2017,p. 4786 - 4793

73
[ 2942-14-5 ]
[ 873-76-7 ]
[ 1242320-83-7 ]

Reference： [1]Applied Organometallic Chemistry,2018,vol. 32

74
[ 873-76-7 ]
[ 1972-28-7 ]
diethyl 1-(4-chlorobenzoyl)hydrazine-1,2-dicarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tert.-butylhydroperoxide; copper(II) oxide; In acetonitrile; at 80℃; for 6h;Inert atmosphere;	General procedure: The appropriate dialkyl azodicarboxylate (1.5 mmol) was addedto a stirred mixture of CuO nanoparticles (10 mol%) and a benzylicalcohol (0.75 mmol) in MeCN (0.5 mL) under argon. A 30%solution of t-BuOOH (2 equiv) was added dropwise, and themixture was stirred at 80 C for 6 h. When the benzaldehydegenerated in situ had been consumed (TLC; decolorization ofthe azodicarboxylate was also observed), the mixture wastreated with NaBH4 (0.5 mmol, 20 mg) in MeOH (0.5 mL). After 5min, the reaction was quenched with aq NH4Cl (1 mL) and brine(1 mL). The cooled mixture was centrifuged to separate the catalystthen extracted with EtOAc (2 × 20 mL). The extracts weredried (MgSO4), filtered, and concentrated in vacuo to give acrude product that was purified by column chromatography[silica gel, EtOAc-hexanes (1:4)].

Reference： [1]Tetrahedron,2018,vol. 74,p. 3858 - 3870
[2]Synlett,2018,vol. 29,p. 189 - 192

75
[ 873-76-7 ]
[ 73183-34-3 ]
[ 302348-51-2 ]

Reference： [1]RSC Advances,2018,vol. 8,p. 13643 - 13648

76
[ 15411-43-5 ]
[ 873-76-7 ]
C₁₅H₁₂ClN [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 10401 - 10406

77
[ 61964-08-7 ]
[ 873-76-7 ]
C₁₅H₁₂ClNO [ No CAS ]

Reference： [1]ACS Catalysis,2018,vol. 8,p. 10401 - 10406

78
[ 591-50-4 ]
[ 873-76-7 ]
[ 831-81-2 ]

Reference： [1]Organic Letters,2018,vol. 20,p. 7846 - 7850

79
[ 104-88-1 ]
[ 75-05-8 ]
[ 69957-83-1 ]
[ 873-76-7 ]

Reference： [1]Green Chemistry,2019,vol. 21,p. 300 - 306

80
[ 105-45-3 ]
[ 873-76-7 ]
[ 73257-49-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With ammonium hydroxide; hydrogen bromide; dimethyl sulfoxide; In water; at 75℃; for 2.53333h;	General procedure: A mixture of HBr (48% aq., 1 mmol) in DMSO (1 mL) was stirred for 2 min at 75 C. Then, benzylic alcohol (1 mmol), alkyl acetoacetate (2 mmol), and ammonium hydroxide (1.5 mmol) were added to the reaction mixture and stirring was continued at 75 C for 2.5 h. The completion of reaction was followed by TLC. After the reaction was complete, the reaction mixture was cooled to ambient temperature, quenched by addition of water (2 mL), and stirring was continued for 10 min at ambient temperature. The resulting precipitate was filtered, washed with water, dried, and recrystallized from ethanol to afford the pure product 4.

Reference： [1]Tetrahedron Letters,2018,vol. 59,p. 4102 - 4106

81
[ 14062-80-7 ]
[ 873-76-7 ]

Reference： [1]Angewandte Chemie - International Edition,2019,vol. 58,p. 4992 - 4997
Angew. Chem.,2019,vol. 131,p. 5046 - 5051,6

82
[ 1375008-18-6 ]
[ 873-76-7 ]
[ 49562-28-9 ]

Reference： [1]European Journal of Organic Chemistry,2019,vol. 2019,p. 4832 - 4843

83
[ 66003-78-9 ]
[ 873-76-7 ]
[ 19962-25-5 ]

Reference： [1]Chemistry - An Asian Journal,2019,vol. 14,p. 3370 - 3379

84
[ 590-92-1 ]
[ 873-76-7 ]
4-chlorobenzyl 3-bromopropanoate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 17117 - 17124

85
[ 104-88-1 ]
[ 98-86-2 ]
[ 5739-39-9 ]
[ 873-76-7 ]

Reference： [1]Chemistry - A European Journal,2019,vol. 25,p. 16225 - 16229

86
[ 873-76-7 ]
[ 73257-49-5 ]

Reference： [1]New Journal of Chemistry,2020,vol. 44,p. 1508 - 1516

87
[ 98-86-2 ]
[ 873-76-7 ]
[ 956-04-7 ]
[ 5739-39-9 ]

Reference： [1]ACS Catalysis,2020,vol. 10,p. 3640 - 3649

88
[ 1885-32-1 ]
[ 873-76-7 ]
[ 1361458-50-5 ]

Reference： [1]RSC Advances,2021,vol. 11,p. 17721 - 17726

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Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P222	Do not allow contact with air.
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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. 873-76-7 ] {[proInfo.proName]}

Quality Control of [ 873-76-7 ]

Related Doc. of [ 873-76-7 ]

Product Details of [ 873-76-7 ]

Calculated chemistry of [ 873-76-7 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 873-76-7 ]

Application In Synthesis of [ 873-76-7 ]

[ 873-76-7 ] Synthesis Path-Upstream 1~23

[ 873-76-7 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 873-76-7 ]

Aryls

Chlorides

Alcohols

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 873-76-7 ]