[ CAS No. 71989-96-3 ] {[proInfo.proName]}

Name: 71989-96-3|(2,3,4-Trimethoxyphenyl)methanol|95%
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SKU: A895374
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2D 3D

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COA NMR CNMR HPLC LC-MS

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Product Details of [ 71989-96-3 ]

CAS No. :	71989-96-3	MDL No. :	MFCD00004613
Formula :	C₁₀H₁₄O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DGJVVEVPKPOLEV-UHFFFAOYSA-N
M.W :	198.22	Pubchem ID :	123571
Synonyms :		Chemical Name :	(2,3,4-Trimethoxyphenyl)methanol

Calculated chemistry of [ 71989-96-3 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.4
Num. rotatable bonds :	4
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	52.05
TPSA :	47.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.89 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.4
Log Po/w (XLOGP3) :	0.87
Log Po/w (WLOGP) :	1.05
Log Po/w (MLOGP) :	0.64
Log Po/w (SILICOS-IT) :	1.72
Consensus Log Po/w :	1.34

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.67
Solubility :	4.24 mg/ml ; 0.0214 mol/l
Class :	Very soluble
Log S (Ali) :	-1.46
Solubility :	6.87 mg/ml ; 0.0346 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.62
Solubility :	0.481 mg/ml ; 0.00243 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.8

Safety of [ 71989-96-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 71989-96-3 ]

* 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 [ 71989-96-3 ]
Downstream synthetic route of [ 71989-96-3 ]

[ 71989-96-3 ] Synthesis Path-Upstream 1~1

1
[ 71989-96-3 ]
[ 2103-57-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [CuNi(-OAc)(μ-OH)(μ-OH₂)(bpy)₂](ClO₄)₂; dihydrogen peroxide In water at 70℃; for 2 h;	To a mixture of benzyl alcohol (0.5 mL, 4.64 mmol) and 15percent aqueous hydrogen peroxide(1.1 mL, 4.85 mmol), the catalyst [CuNi(-OAc)(-OH)(-OH2)(bpy)2](BF4)2 (8 mg, 0.01 mmol)was added and stirred at 70 °C for 5 h. The organic and aqueous phase were separated by aseparating funnel and then puried by column chromatography to aord benzaldehyde.The identity of the benzaldehyde was ascertained by comparison with authentic sampleusing IR, 1H NMR, and 13C NMR.
90%	With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; C₁₈H₁₈Mo₂N₄O₁₀; dihydrogen peroxide In acetonitrile at 20 - 70℃; for 3 h;	General procedure: Benzyl alcohol (0.05g, 0.5mmol), was added to a mixture of 15percent H₂O₂ (0.3 g, 8.83mmol), complex [MoO₂)₂(slsch)(H₂O)₂] (0.01g, 0.017mmol) in acetonitrile solution in 50mL round bottom flask. The mixture was first stirred at ambient temperature for 20mins and then the temperature was raised to 70°C for 2h. The crude product was separated by a separating funnel and dried over anhydrous sodium sulfate. The oxidized product was purified by column chromatography to afford benzaldehyde. The isolated product was ascertained by comparison with the authentic sample using ¹H and ¹³C NMR spectroscopies.

Reference： [1] Journal of Coordination Chemistry, 2017, vol. 70, # 15, p. 2722 - 2735
[2] Tetrahedron Letters, 2008, vol. 49, # 28, p. 4339 - 4341
[3] Applied Organometallic Chemistry, 2018, vol. 32, # 4,
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 395 - 402
[5] Inorganic Chemistry Communications, 2017, vol. 86, p. 39 - 43
[6] Tetrahedron Letters, 2013, vol. 54, # 23, p. 2924 - 2928
[7] Organic and Biomolecular Chemistry, 2011, vol. 9, # 14, p. 5211 - 5219
[8] Chemical Science, 2015, vol. 6, # 2, p. 945 - 955
[9] European Journal of Organic Chemistry, 2014, vol. 2014, # 2, p. 395 - 402
[10] ChemistryOpen, 2017, vol. 6, # 1, p. 112 - 120
[11] ChemSusChem, 2017, vol. 10, # 17, p. 3497 - 3505
[12] Journal of Chemistry, 2017, vol. 2017,
[13] RSC Advances, 2017, vol. 7, # 87, p. 55336 - 55349

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	With thionyl chloride In dichloromethane	Ingredients: 2,3,4-Trimethoxybenzylchloride Ingredients: 50.0 g (0.25 mol) 2,3,4-trimethoxybenzylalcohol 800 ml of anhydrous methylene chloride 59.4 g (0.5 mol) of thionylchloride
	With pyridine; thionyl chloride; sulfuric acid In dichloromethane	47.a 47a 47a 2,3,4-Trimethoxybenzyl chloride 5 g (24.47 mmol) of 2,3,4-trimethoxybenzyl alcohol (Aldrich, Steinheim, FRG) are dissolved, under argon, in 13.9 ml of abs. methylene chloride, and this solution is treated with 0.278 ml of pyridine. 3.05 ml of thionyl chloride in 6.94 ml of abs. methylene chloride are added dropwise to this solution, while cooling slightly (ice/water), within the period of 20 min. During this procedure, the internal temperature rises to approximately 18°-23° C. The mixture is left to react subsequently for 45 min and the slightly yellow solution is then poured onto ice/water. After the phases have been separated, the organic phase is washed once each with 1N sulfuric acid and water. After drying over Na2 SO4, and removing the solvent, the oily residue is distilled under HV (b.p.: 93°-95° C./0.07 Torr), and the title compound is obtained. 1 H-NMR (220 MHz, CDCl3): 7.05 (d, 1H); 6.65 (d, 1 H); 4.61 (s, 2H); 3.97 (s, 3H); 3.85 (s, 3H). HPLC: tRet =8.1 min (gradient II).
	With hydrogenchloride In water	81 5-Deoxy-5-[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]-1.4;3.6-dianhydro-L-iditol 2-nitrate (Compound 73) EXAMPLE 81 5-Deoxy-5-[4-(2,3,4-trimethoxybenzyl)piperazin-1-yl]-1.4;3.6-dianhydro-L-iditol 2-nitrate (Compound 73) 5.0 g (4.34 mmols) of 2,3,4-trimethoxybenzyl alcohol was dropwise added to 10 ml of conc. hydrochloric acid under stirring at 0° C. The mixture was stirred at 0° C. for further 5 minutes. After the reaction, water was added to the mixture followed by extraction of the solution with diethyl ether. The diethyl ether layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to afford 4.80 g of 2,3,4-trimethoxybenzyl chloride as a crude product. A mixture of 2.44 g of the crude product of 2,3,4-trimethoxybenzyl chloride described above, 1.73 g (6.67 mmols) of Compound b obtained in Reference Example 2 and 50 ml of methyl ethyl ketone was stirred at room temperature for 4 days.

Yield	Reaction Conditions	Operation in experiment
99%	With phosphorus tribromide In dichloromethane at 0℃; for 2h; Inert atmosphere;
93%	With phosphorus tribromide In diethyl ether at 0 - 20℃; for 1h;
	With phosphorus tribromide In diethyl ether at -10℃; for 1h;

	With pyridine; phosphorus tribromide In toluene at 4℃; for 0.75h;
	With pyridine; phosphorus tribromide In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; toluene	47.i 47i 47i 2,3,4-Trimethoxybenzyl bromide 2.04 g (10 mmol) of 2,3,4-trimethoxybenzyl alcohol in 30 ml of abs. toluene are treated with 0.258 ml (0.32 equivalents) of pyridine, and the solution is cooled down to approximately 4° C. using ice-water. 0.951 ml of phosphorus tribromide in 5 ml of abs. toluene is added dropwise, at this temperature and over the period of 30 min, to this solution, which is left to stir at this temperature for a further 45 min. The reaction mixture is diluted with ether and the whole is poured onto ice-water, with this mixture then being stirred for 5 min. After the phases have been separated, the organic phase is washed, in succession, with water, saline, sat. sodium bicarbonate solution and once again with saline (all being cold). After the organic phase has been dried over sodium sulfate, it is concentrated, and residual solvents are removed from the residue under high vacuum for 1 h. The resulting title compound is subjected, without purification, to further processing. 1 H-NMR (200 MHz; CDCl3)=7.05/d (1H); 6.65/d (1H); 4.55/s (2H); 4.07, 3.88 and 3.85/each s (each 3H).
	With phosphorus tribromide In dichloromethane at 0℃; for 0.5h;	General procedure for the preparation of 4-aminomethyl-3-(substituted benzyloxyimino)pyrrolidine dimesylates (8a-w) General procedure: To a solution of phenylmethanols 5a-w (5 mmol) dissolved in methylene chloride (50 mL) in an ice-water bath was added phosphorus tribromide (5.5 mmol), and the mixture was stirred at the same temperature for 30 min. The mixture was washed with cool water, dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (bromomethyl)benzenes 6aew as offwhite solids or light yellow oils
	With phosphorus tribromide In dichloromethane at 0 - 5℃; for 0.75h;	General procedure: crude product 2a which was then dissolved in anhydrous methylene chloride (50 mL) and cooled to 0-5 ºC by ice bath. To this solution was added dropwise phosphorus tribromide (0.5 mL, 5 mmol) over a period of 15 min and stirred for 0.5 h at the same temperature, and then washed with saturated brine (3 Χ 15 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude compound 3a.
	Stage #1: 2,3,4-trimethoxybenzylalcohol In dichloromethane at -10℃; for 0.166667h; Stage #2: With phosphorus tribromide In dichloromethane at -10℃; for 1.5h;	Synthesis of 1-(bromomethyl)-2,3,4-trimethoxybenzene Synthesis of 1-(bromomethyl)-2,3,4-trimethoxybenzene A solution of (2,3,4-Trimethoxyphenyl)methanol (5.00 g, 25.2 mmol) in dry DCM (35 mL) was stirred at -10° C. in an ice/NaCl bath. After 10 min, phosphorous tribromide (13.65 g, 4.75 mL, 50.5 mmol) was added dropwise by syringe. The reaction was monitored by TLC. After 90 min, the reaction was quenched with cool 10% sodium bicarbonate (50 mL) and washed with diethyl ether (75 mL). The ether extract was washed with 10% NaHCO3 (3*50 mL). The ether extract was dried over MgSO4 and concentrated in vacuo at a low temperature to prevent degradation of the product. The product was obtained as a colourless oil after being placed under high vacuum for not more than 2 h. The product was not purified and further and was used in directly in the following reaction. 1H NMR (CDCl3, 400 MHz) δH ppm: 3.88 (s, 3H, CH3), 3.89 (s, 3H, CH3), 4.04 (s, 3H, CH3), 4.57 (s, 1H, CH2Br), 6.66 (d, J=8.56 Hz, 1H, ArH), 7.07 (d, J=8.56 Hz, 1H, ArH).
	With phosphorus tribromide In dichloromethane at 0℃; for 2h; Inert atmosphere;
	With phosphorus tribromide In dichloromethane at 0 - 20℃; for 1h;

Yield	Reaction Conditions	Operation in experiment
98%	With lithium hydroxide monohydrate; nickel (II) chloride; zinc In N,N-dimethyl-formamide for 2h; Ambient temperature;
98%	With cobalt(II) chloride; zinc In lithium hydroxide monohydrate; N,N-dimethyl-formamide for 1.5h; Ambient temperature;
98%	With sodium tetrahydridoborate In methanol; hexane; ethyl acetate at 0℃; for 0.5h;	1 Step 1: Synthesis of (2,3,4-Trimethoxyphenyl)methanol Step 1: Synthesis of (2,3,4-Trimethoxyphenyl)methanol To a stirred solution of 2,3,4-trimethoxybenzaldehyde (10.50 g, 532 mmol) in methanol (150 mL) was added sodium borohydride (2.65 g, 70 mmol) at 0° C. The progress of the reaction was monitored by Thin Layer Chromatography (TLC) using hexane/ethyl acetate 4:1 as the mobile phase. After 30 min, the reaction was quenched by the addition of water (100 mL). The methanol was removed from the mixture in vacuo. The product was extracted with diethyl ether (1150 mL, 275 mL). The organic extracts were combined, dried over MgSO4 and concentrated to a yield the product as a colourless oil. Yield: 10.25 g (51.71 mmol, 98%). 1H NMR (CDCl3, 400 MHz) δH ppm: 3.88 (s, 3H, CH3), 3.90 (s, 3H, CH3), 3.98 (s, 3H, CH3), 4.64 (d, J=6.12 Hz, 2H, CH2), 6.66 (d, J=8.44 Hz, 1H, ArH), 7.00 (d, J=8.44 Hz, 1H, ArH). 13C NMR (CDCl3, 100.71 MHz) δc ppm: 55.5 (CH3), 60.3 (COH3), 60.7 (CH3), 61.1 (CH3), 122.9 (CH), 126.4 (CH), 141.4 (CH), 141.4 (Q), 151.2 (Q), 152.9 (Q).

[ CAS No. 71989-96-3 ] {[proInfo.proName]}

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