5400-78-2|1-(3-Nitrophenyl)ethanol| Ambeed

Structure of 5400-78-2

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Quality Control of [ 5400-78-2 ] Purity: 97% SDS Specification

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Product Details of [ 5400-78-2 ]

CAS No. :	5400-78-2
Formula :	C₈H₉NO₃
M.W :	167.16
SMILES Code :	CC(O)C1=CC=CC([N+]([O-])=O)=C1
MDL No. :	MFCD00053608
Boiling Point :	No data available
InChI Key :	FRPQAVXDUWMFCK-UHFFFAOYSA-N
Pubchem ID :	223135

Safety of [ 5400-78-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 5400-78-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	12
Num. arom. heavy atoms	6
Fraction Csp3	0.25
Num. rotatable bonds	2
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	46.2
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	66.05 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.48
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.6
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.32
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.68
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-0.33
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	0.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.12
Solubility	1.26 mg/ml ; 0.00754 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.6
Solubility	0.421 mg/ml ; 0.00252 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.63
Solubility	3.9 mg/ml ; 0.0233 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.18 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	2.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.15

Application In Synthesis of [ 5400-78-2 ]

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

Downstream synthetic route of [ 5400-78-2 ]

[ 5400-78-2 ] Synthesis Path-Downstream 1~35

1
[ 555-31-7 ]
[ 121-89-1 ]
[ 5400-78-2 ]

References: [1]Journal of the American Chemical Society,1949,vol. 71,p. 3622,3623.

2
[ 121-89-1 ]
[ 5400-78-2 ]

Yield	Reaction Conditions	Operation in experiment
98%		General procedure: In a round-bottomed flask (10 mL) equipped with a magneticstirrer, a mixture of nitrobenzene (0.123 g, 1 mmol)and H2O (2 mL) was prepared. Ni2B (0.006 g, 0.05 mmol) was then added and the mixture was stirred for 5 min.NaBH4 (0.095 g, 2.5 mmol) was also added and the resultingmixture was continued to stirring for 3 min at roomtemperature. TLC monitored the progress of the reaction(eluent, n-hexane/Et2O:5/3). After completion of the reaction,aqueous solution of KOH (2 %, 5 mL) was addedand the mixture was stirred for 10 min. The mixture wasextracted with EtOAc (3 × 8 mL) and then dried overanhydrous Na2SO4. Evaporation of the solvent affords thepure liquid aniline in 95 % yield (0.088 g, Table 2, entry 1).
97%	With methanol; sodium tetrahydroborate; at 0 - 20℃; for 1.5h;	Methanol (50 mL) was sequentially added to a 100 mL third product vial, m-nitroacetophenone (6.6g, 40mmol, 1.0eq), cooled to 0 C, Sodium borohydride (2.16 g, 60 mmol, 1.5 eq) was added in portions and reacted at room temperature for 1.5 hours.TLC tracks the end of the reaction. Concentrated methanol,Add 50 mL of water to the system and extract twice with ethyl acetate (30 mL*2),The organic phases were combined, washed twice with saturated brine, and the organic phase was dried over anhydrous sodium sulfate and concentrated to obtain 6.5 g of 1-(3-nitrophenyl)ethanol with a yield of 97%.
96%	With sodium tetrahydroborate; In water; at 60 - 70℃; for 0.1h;Green chemistry;	General procedure: In a round-bottom flask (10 mL) containing 2 mL water, a mixture of nitrobenzene (0.123 g, 1 mmol) and Fe3O4SiO2Cu-Ni-Fe-Cr LDH (10 mg) was prepared and the resulting mixture was stirred for 5 min. Next, NaBH4(0.076 g, 2 mmol) was added and the reaction mixture was stirred magnetically for 3 min under oil bath conditions (60-70 C). TLC monitored the progress of the reaction (eluent, n-hexane/EtOAc: 5/2). After completion of the reduction reaction, the mixture was cooled to the room temperature. EtOAc (3 mL) was then added and the resulting mixture was again stirred for 10 min. The magnetic nanocatalyst was separated by an external magnet followed by extraction with EtOAc (2 × 5 mL). The combined organic layers were dried over anhydrous Na2SO4. Evaporation of the solvent afforded the pure liquid aniline in 95% yield (Table 2, entry 1).

95%	With sodium tetrahydroborate; In methanol; at 0℃; for 1h;	1-(3-Nitrophenyl)ethanol (ID30) To a solution of 1-(3-nitrophenyl)ethanone (ID29, 2.32 g, 14.0 mmol) in MeOH (100 mL) at 0 C. was added NaBH4 (2.20 g, 58.2 mmol) and the resulting mixture was allowed to stir at 0 C. for 1 h. After concentration, the residue was diluted with EtOAc (150 mL) and water (50 mL) and the organic layer was washed with water (50 mL), brine (50 mL), and dried over Na2SO4. After filtration, the filtrate was concentrated and the residue was dried in vacuo to give compound ID30 as a yellowish oil (2.23 g, 95%). 1H NMR (CDCl3, 600 MHz) delta 8.25 (s, 1H), 8.12 (ddd, J=8.4, 1.2, 1.2 Hz, 1H), 7.72 (d, J=7.2 Hz, 1H), 7.52 (dd, J=8.1, 8.1 Hz, 1H), 5.02 (q, J=6.6 Hz, 1H), 2.07 (s, 1H), 1.54 (d, J=6.6 Hz, 3H).
92%	With 2BH4(1-)Zn(2+)Cl2Na2; In acetonitrile; at 20℃; for 0.666667h;	General procedure: In a round-bottomed flask (10 mL), equipped with a magneticstirrer bar, a solution of acetophenone (0.121 g, l mmol) was prepared in CH3CN(3 mL). To this solution, Zn(BH4)2/2NaCl (0.210 g,1 mmol) was added. The resulting mixture was stirred at room temperature for 60 min. The reaction was monitored by TLC(eluent; Hexane/EtOAc: 10/1). After completion of the reaction, distilled water (5 mL) was added to the reaction mixture and stirred for 5 min. The mixture was extracted with CH2Cl2 (3 ×8 mL) and dried over anhydrous Na2SO4. Evaporation of the solvent followed column chromatography of the resulting crude material over silica gel (eluent; Hexane/EtOAc: 10/1) afforded crystals of 1-phenylethanol (0.l1 g, 93 % yield,Table 2, entry 11).
90%	With sodium borohydrid; In ethanol;	EXAMPLE 3 1-(m-Nitrophenyl)ethyl monate A A solution of sodium borohydride (0.4 g, 10 mmol) in ethanol (10 ml) was treated with m-nitroacetophenone (3.3 g, 20 mmol) at 20 C. for 20 mins. The solution was the diluted with aqueous potassium carbonate and extracted with chloroform. The extracts were dried (magnesium sulphate) and evaporated in vacuo to give 1-(m-nitrophenyl)ethanol as an oil (2.9 g, 90%);
	With sodium tetrahydroborate; In ethanol;	a) Synthesis of alpha-methl-3-nitrobenzenemethanol [R1=CH3, X1=X2=H in formula (XVI)] 33 g (199.8 mmol) of 1-(3-nitrophenyl)ethanone [R1=CH3, X1=X2=H in formula (XV)] was weighed and charged into a 500 ml of eggplant type flask, followed by the addition of 120 ml of ethanol. After cooling on an ice water bath, 4.2 g (111 mmol) of NaBH4 was added in portions and the mixture was reacted for 30 minutes under ice cooling bath and for 2 hours at room temperature. The resulting reaction liquid was concentrated by evaporator and the residue was washed with water to quantitatively obtain light brown oil of alpha-methyl-3-nitrobenzene methanol [R1=CH3, X1=X2=H in formula (XVI)].
	With methanol; sodium tetrahydroborate;Cooling with ice;	Preparation of 2-(4-methylpiperazin-1-yl)ethyl {3-[1-(5,6-difluoro-2-oxobenzoxazol-3-yl)ethyl]phenyl}carbamate (?A27?)Step aPreparation of 1-(3-nitrophenyl)ethanol26.4 g (160 mmol) of 1-(3-nitrophenyl)ethanone are suspended in 270 ml of methanol, and 6.1 g (160 mmol) of sodium borohydride are added in portions with ice cooling. The reaction mixture is subsequently stirred for a further 3 h without cooling, diluted with 300 ml of dichloromethane and washed with 3×200 ml of water. The organic phase is dried over sodium sulfate and evaporated to dryness.Product: 26.15 g; HPLC: Rt=3.87 min (method A).
		General procedure: All racemic alcohols except for the (R,S)-1-phenylethanol were prepared using the following procedure: a mixture of ketone (5 mmol) and sodium borohydride (10 mmol) in anhydrous methanol (50 mL) was stirred at room temperature for 30 min. Next, saturated NaHCO3 (50 mL) and CH2Cl2 (100 mL) were introduced, and the mixture was stirred at room temperature for another 10 min. The organic layer was removed, and the aqueous layer was extracted twice with 25 mL CH2Cl2. The combined organic layers were dried over anhydrous Na2SO4 and concentrated to give the corresponding crude alcohols. The crude alcohols were then chromatographed to afford pure products. The 1H NMR spectra of these products were in good agreement with the literature.
67%Chromat.	With sodium hydroxide; In isopropyl alcohol; at 82℃; for 0.75h;	General procedure: In a typical procedure, a 5 mg (0.77 mol%) of RuO2/MWCNT and 80 mg (2 mmol) of NaOH were stirred with 5 mL of i-PrOH taken in an ace pressure tube equipped with a stirring bar. Then the substrate (1 mmol) was added to the stirring solution and then the mixture was heated at 82C. The completion of the reaction was monitored by GC. After the reaction, the catalyst was separated out from the reaction mixture by simple centrifugation and the products and unconverted reactants were analyzed by GC without any purification. Selectivity of the product for each reaction was alsocalculated. Finally, the separated RuO2/MWCNT was washed well with diethyl ether followed by drying in an oven at 60C for 5 h and it was reused for the subsequent transfer hydrogenation of carbonyl compounds to investigate the reusability of the RuO2/MWCNT.
	With sodium tetrahydroborate; In methanol; at 0℃; for 4h;	General procedure: To a solution of the corresponding ketone in methanol (0.60 M) was added sodiumborohydride (0.33 equiv.) and the resulting mixture was stirred for 2 h at 0 C. Afterstirring, additional sodium borohydride (0.33 equiv.) was added to the mixture tocomplete the transformation. After 2 h, water was added to quench the reaction, andthe mixture was extracted with diethyl ether (3 times). The extracts were dried overanhydrous MgSO4, filtered, and concentrated under reduced pressure. The residuewas chromatographed on silica gel to afford desired alcohol.
	With methanol; sodium tetrahydroborate; at 0 - 20℃;	General procedure: Ten mmol of NaBH4 was added to a cooled (0C) solution of 2.5 mmol of each specific substrate(1a-1f, 1m and 1n) in 50 mL of methanol. After stirring for 10 min, the mixture was warmed to room temperature and stirred for another 3-4 h to complete the reduction. After quenching with 2 M HCl topH 7.0, the mixture was extracted with EtOAc (50 mL 3). The organic phases were washed withbrine, dried over Na2SO4, filtered and concentrated in vacuum. The residue was purified by flashchromatography on silica gel (eluent: EtOAc/PE 1:20) to give the racemic alcohol 2a-2f, 2m and 2n(see Supplementary Materials for NMR spectroscopic data).

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[4]Chemistry Letters,1987,p. 181 - 184.
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[6]Dalton Transactions,2013,vol. 42,p. 6513 - 6522.
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[8]Patent: CN110498744,2019,A .Location in patent: Paragraph 0022-0027; 0034-0038; 0045-0049; 0056-0060.
[9]Green Chemistry,2013,vol. 15,p. 629 - 634.
[10]Journal of the Iranian Chemical Society,2018,vol. 15,p. 2821 - 2837.
[11]Tetrahedron Asymmetry,2009,vol. 20,p. 1057 - 1061.
[12]Journal of the Brazilian Chemical Society,2010,vol. 21,p. 1509 - 1516.
[13]Patent: US2016/376238,2016,A1 .Location in patent: Paragraph 0363.
[14]RSC Advances,2014,vol. 4,p. 61077 - 61085.
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3
[ 75-35-4 ]
[ 5400-78-2 ]
[ 21157-26-6 ]

References: [1]Tetrahedron Letters,1968,p. 4979 - 4982.

4
[ 5400-78-2 ]
[ 29067-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid; In water; at 20℃; for 120h;Cooling with ice;	Step bPreparation of 1-(1-bromoethyl)-3-nitrobenzene26.15 g (156 mmol) of <strong>[5400-78-2]1-(3-nitrophenyl)ethanol</strong> are dissolved in 130 ml of glacial acetic acid, and 55 ml (313 mmol) of 33% HBr in glacial acetic acid are added dropwise with ice cooling. The reaction mixture is stirred at room temperature for 5 days. The mixture is subsequently diluted with 300 ml of DCM, washed with 3×200 ml of H2O and 200 ml of saturated NaHCO3 solution, dried over sodium sulfate and evaporated to dryness, and the residue is crystallised from petroleum ether.Product: 30.4 g; HPLC: Rt=5.39 min (method A).

References: [1]Journal of medicinal chemistry,1970,vol. 13,p. 559 - 561.
[2]Patent: US2010/280030,2010,A1 .Location in patent: Page/Page column 22.

5
[ 85-44-9 ]
[ 5400-78-2 ]
[ 125280-36-6 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1989,vol. 25,p. 738 - 740.
Zhurnal Organicheskoi Khimii,1989,vol. 25,p. 823 - 825.

6
[ 5400-78-2 ]
[ 34586-27-1 ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; In dichloromethane; at 0 - 35℃;	Thionyl chloride (162ul, 8.9 mmol) was added dropwise to a solution of l-(3-nitro-phenyl)-ethanol (4.4 mmol) in DCM (50 ml) at 0 0C. The reaction was stirred at room temperature for 2 h. Further thionyl chloride (162 mul, 8.9 mmol) was added and the reaction stirred at 35 0C for 24 h. The mixture was evaporated to give the desired product as a yellow oil. NMR (DMSO) shows 70%, together with 3-nitrostyrene impurity. Used in the next step without further purification.

References: [1]Journal of the American Chemical Society,1983,vol. 105,p. 3967 - 3975.
[2]Journal of Organic Chemistry USSR (English Translation),1971,vol. 7,p. 2238 - 2242.
Zhurnal Organicheskoi Khimii,1971,vol. 7,p. 2157 - 2161.
[3]Patent: WO2009/122180,2009,A1 .Location in patent: Page/Page column 93.

7
[ 5400-78-2 ]
[ 105360-83-6 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 2076 - 2086.

8
[ 5400-78-2 ]
[ 105360-83-6 ]
[ 121-89-1 ]

References: [1]Canadian Journal of Chemistry,1986,vol. 64,p. 2076 - 2086.

9
[ 586-39-0 ]
[ 5400-78-2 ]

References: [1]Journal of Organic Chemistry,1984,vol. 49,p. 1589 - 1594.

10
[ 5400-78-2 ]
[ 17279-31-1 ]
[ 108-24-7 ]
[ 5400-78-2 ]
[ 188016-03-7 ]
[ 103966-64-9 ]

References: [1]Journal of Organic Chemistry USSR (English Translation),1985,vol. 21,p. 1602 - 1606.
Zhurnal Organicheskoi Khimii,1985,vol. 21,p. 1753 - 1758.

11
[ 5400-78-2 ]
[ 76-05-1 ]
[ 82639-02-9 ]

References: [1]Tetrahedron Letters,1981,vol. 22,p. 597 - 600.

12
[ 5400-78-2 ]
[ 16794-67-5 ]
O-<1-(3-nitrophenyl)ethyl> N-(4-chlorobenzoyl)monothiocarbamate [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1994,vol. 59,p. 2650 - 2662.

13
[ 5400-78-2 ]
[ 121-89-1 ]

Yield	Reaction Conditions	Operation in experiment
96%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium tert-butylate; copper(I) triflate; 5-[(2S)-pyrrolidine-2-yl]-1H-tetrazole; In N,N-dimethyl-formamide; at 25℃; for 1.5h;Catalytic behavior;	General procedure: A round-bottom flask was charged with alcohol (2 mmol), CuOTf (0.1 mmol, 0.05 equiv) (S)-5-(pyrrolidin-2-yl)-1H-tetrazole (0.1 mmol, 0.05 equiv), TEMPO (0.1 mmol, 0.05 equiv), t-BuOK (2 mmol, 1 equiv) and DMF (5 ml). The reaction mixture was stirred at 25 C open to air until the completion of the reaction, as monitored by TLC. The mixture was then diluted with CH2Cl2 (20 ml), washed with water, dried over Na2SO4, and evaporated under vacuum to give the crude product, which was purified by column chromatography to give the pure product.
95%	With dihydrogen peroxide; acetic acid; sodium bromide; In water; at 60℃; for 2h;Inert atmosphere;	General procedure: Under nitrogen atmosphere, to a solution of substrate alcohol (0.5 mmol) in aceticacid (1.0 mL) was added a stock-solution of aqueous NaBr solution (1.94 M, 25 muL)and 30% aqueous H2O2 (50 muL, 0.5 mmol). After stirring the mixture for one hour at60 C, additional 30% aqueous H2O2 (50 muL, 0.5 mmol) was added, and stirring wascontinued for another one hour. After cooling, the mixture was poured into a saturatedaqueous NaHCO3 solution (ca. 30 mL) with the aid of CH2Cl2, and resulting mixturewas extracted with CH2Cl2. The combined organic layers were dried over anhydrousMgSO4, filtered and concentrated in vacuo. The residue was chromatographed onsilica gel (flash column or preparative TLC) to afford the corresponding ketone.
90%	With 1-methyl-1H-imidazole; [2,2]bipyridinyl; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; sodium chloride; In neat (no solvent);Milling; Green chemistry;	General procedure: 2,2,6,6-Tetramethylpiperidine 1-oxyl (TEMPO, 9.4 mg,0.06 mmol, 3 mol %), 2,2?-bipyridyl (9,4 mg, 0.06 mmol,3 mol %), [Cu(CN)4]OTf (22.6 mg, 0.06 mmol, 3 mol %) and1-methylimidazole (NMI, 11.5 mg, 11.2 muL, 0.14 mmol,7 mol %) were placed in a zirconia-milling beaker (45 mL)equipped with four balls (two balls × 5 mm , two balls ×12 mm ) of the same material. The jar was sealed and ballmilled for 1 min. Then, benzyl alcohol (216.3 mg, 207 muL,2.0 mmol), NaCl (1.0 g) together with other two zirconia balls(12 mm ) were added and the reaction mixture was subjectedto grinding for further 10 minutes overall (two cycles of5 minutes each). The first milling cycle was followed by a breakof 2 min leaving in the meantime the uncovered jar in open air.The progress of the reaction was monitored by TLC analysis(heptane/AcOEt 9:1 v/v) and GC-MS analysis on an aliquot ofthe crude. Upon completion of the ball milling process, the jarwas opened, the milling balls were removed and the resultingcrude product (adsorbed on NaCl) was then easily transferredinto a separating funnel filled with an aqueous 10% citric acidsolution (20 mL). The aqueous phase was extracted withcyclopentyl methyl ether (or alternatively with AcOEt)(3 × 15 mL). The combined organic fractions were washed withH2O (25 mL) and brine (25 mL), then dried over Na2SO4, andconcentrated in vacuo to give benzaldehyde in high yield (195 mg, 92%) and good purity (>93% by GC analysis). Alternatively, after completion of the reaction, the resulting crudeproduct (adsorbed on NaCl) can be also easily purified by ashort column chromatography on silica gel using heptane/ethylacetate (9:1 v/v) as the eluents to afford pure aldehyde 2b inhigh yield (202 mg, 95%) as a colourless liquid.

87%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; at 75℃; for 1.66667h;	General procedure: A mixture of alcohols (1 mmol) and DBDMH or DCDMH (1-1.5 mmol) in a 10 mL round-bottomed flask sealed with a stopper, was stirred in an oil-bath for the appropriate time and temperature (Table 1) under solvent-free condition. Then, as monitored by TLC (eluent n-hexane/acetone 10:2), hot water (10 mL) was added to mixture and stirred magnetically for 10 min. Then, the solution was extracted with (CH2Cl2/water (2 × 10 mL)) and organic phase dried over anhydrous Na2SO4 (1 g). Evaporation of the solvent gave the corresponding carbonyl compounds. Melting points and spectral data of all products are fully consistent with those previously reported. The structures of the products were confirmed from physical and spectroscopic data such as melting points, 1H NMR and 13C NMR spectra, fully consistent with those previously reported.17,18
70%	With 1-hydroxy-1H-1,2,3-benziodoxathiole 1,3,3-trioxide; Oxone; cetyltrimethylammonim bromide; In water; at 20℃; for 2h;Green chemistry;	General procedure: The alcohol (2 mmol) was added to a solution of IBS (0.02 mmol, 0.01 eq), oxone (2.2 mmol, 1.1 equiv.) and 3 wt% CTAB solution (5 mL). The mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the solution was extracted with CH2Cl2 (3 × 10 mL). The combined organic phase was then filtered through a pad of silica gel and evaporated under vacuum to afford the desired product.
62%	With tert.-butylhydroperoxide; eosin y; In decane; acetonitrile; at 25℃; for 72h;Inert atmosphere; Irradiation; Molecular sieve; Green chemistry;	General procedure: Oven dried round bottom flask was charged with Eosin Y (5 mmol) alcohol (1 mmol) and 3 equiv. of TBHP (5.5 M in decane) in dry ACN. The resulting mixture was degassed for 15 mins, followed by back filling N2, and then irradiated under Blue LED light (12W, 455 nm) at room temperature (25 oC). After reaction completion monitored through TLC, the mixture was diluted with 15 ml of 10% NaHCO3 solution, and extracted with EtOAc (3 × 20 ml). The combined organic extracts were washed with brine (20 ml), dried over Na2SO4, and concentrated on vacuo. Purification of the crude product on silica gel using EtOAc:Hexane as solvent system afforded the desired product.
	With tert.-butylhydroperoxide; copper(l) iodide; oxygen; In neat (no solvent); at 50℃; for 4h;	General procedure: The 1-arylethanol (1 mmol) was added to a mixture of CuI (30 mol%) and TBHP (5-6 M in decane, 2 equiv) in a reaction tube at r.t. under an O2 atm (O2 balloon). The resulting mixture was stirred at 50 C for 3- 8 h (TLC monitoring).

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14
[ 108-22-5 ]
[ 5400-78-2 ]
[ 188016-03-7 ]
[ 103966-64-9 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3285 - 3294.

17
[ 64-17-5 ]
[ 5400-78-2 ]
Raney nickel [ No CAS ]
[ 2454-37-7 ]

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18
[ 64-17-5 ]
[ 5400-78-2 ]
[ 127-09-3 ]
[ 75-07-0 ]
Raney nickel [ No CAS ]
[ 799270-63-6 ]

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19
[ 5400-78-2 ]
[ 2454-37-7 ]

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20
[ 188015-95-4 ]
[ 5400-78-2 ]

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21
[ 108-05-4 ]
[ 5400-78-2 ]
[ 103966-64-9 ]
[ 76116-24-0 ]
[ 103966-65-0 ]

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22
[ 5400-78-2 ]
[ 108-24-7 ]
[ 19759-28-5 ]

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[2]Tetrahedron Asymmetry,2008,vol. 19,p. 1418 - 1423.

23
[ 917-64-6 ]
[ 99-61-6 ]
[ 5400-78-2 ]

References: [1]Bioorganic Chemistry,2005,vol. 33,p. 325 - 337.

24
[ 5400-78-2 ]
[ 76116-24-0 ]

References: [1]Tetrahedron Asymmetry,1996,vol. 7,p. 3285 - 3294.

25
[ 5400-78-2 ]
[ 15482-38-9 ]

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Zhurnal Organicheskoi Khimii,1971,vol. 7,p. 2157 - 2161.

26
[ 5400-78-2 ]
[ 21762-09-4 ]