[ CAS No. 19676-64-3 ] {[proInfo.proName]}

Name: 19676-64-3|2,3,4-Trimethoxyphenol|97%
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Quality Control of [ 19676-64-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 19676-64-3 ]

SDS Specification

Alternatived Products of [ 19676-64-3 ]

Product Details of [ 19676-64-3 ]

CAS No. :	19676-64-3	MDL No. :	MFCD00068804
Formula :	C₉H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OLUNIGWWQYXBJA-UHFFFAOYSA-N
M.W :	184.19	Pubchem ID :	603577
Synonyms :

Calculated chemistry of [ 19676-64-3 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	47.94
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) :	-6.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.24
Log Po/w (XLOGP3) :	0.94
Log Po/w (WLOGP) :	1.42
Log Po/w (MLOGP) :	0.6
Log Po/w (SILICOS-IT) :	1.36
Consensus Log Po/w :	1.31

Druglikeness

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

Water Solubility

Log S (ESOL) :	-1.72
Solubility :	3.53 mg/ml ; 0.0192 mol/l
Class :	Very soluble
Log S (Ali) :	-1.53
Solubility :	5.4 mg/ml ; 0.0293 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.21
Solubility :	1.15 mg/ml ; 0.00622 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.66

Safety of [ 19676-64-3 ]

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

Application In Synthesis of [ 19676-64-3 ]

* 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 [ 19676-64-3 ]
Downstream synthetic route of [ 19676-64-3 ]

[ 19676-64-3 ] Synthesis Path-Upstream 1~2

1
[ 2103-57-3 ]
[ 19676-64-3 ]
[ 573-11-5 ]

Reference： [1] Chemische Berichte, 1940, vol. 73, p. 795,802

2
[ 67-66-3 ]
[ 10028-15-6 ]
[ 2103-57-3 ]
[ 19676-64-3 ]
[ 573-11-5 ]

Reference： [1] Chemische Berichte, 1940, vol. 73, p. 795,802

[ 19676-64-3 ] Synthesis Path-Downstream 1~88

1
[ 50-00-0 ]
[ 19676-64-3 ]
[ 39068-88-7 ]

Reference： [1]Journal of Chemical Research,2009,p. 186 - 187
[2]Chemical and pharmaceutical bulletin,1980,vol. 28,p. 1648 - 1650

2
[ 634-36-6 ]
[ 19676-64-3 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium peroxymonosulfate; In d(4)-methanol; water-d2; at 20℃; for 5h;	General procedure: To an NMR tube, 8.4 mg (50 µmoles) of 1 and 2.2 mg (30 µmoles) of tBuOH (used as an internal standard) in a 750 µL solution of 10% (v/v) d3-ACN in D2O were added. A 1H-NMR spectrum was recorded as a zero point (time = 0). A stock solution of 400 mM Oxone in 10% (v/v) d3-ACN in D2O was prepared and a 250 µL aliquot of the Oxone solution was added to the NMR tube to initiate the reaction. The reaction was followed by 1H-NMR spectroscopy over the course of 5 hrs at room temperature. The yields reported were based on the integration of aromatic peaks against the internal standard. This procedure was repeated for each of the different mol equivalents of Oxone, for the different cosolvents, and substrates.

Reference： [1]Journal of Organic Chemistry,1985,vol. 50,p. 1766 - 1768
[2]Chemical Communications,2011,vol. 47,p. 2868 - 2870
[3]Tetrahedron Letters,2013,vol. 54,p. 2344 - 2347
[4]Organic Process Research and Development,2019,vol. 23,p. 595 - 602

3
[ 13909-73-4 ]
[ 19676-64-3 ]

Reference： [1]Tetrahedron,1980,vol. 36,p. 123 - 129
[2]Synthesis,1989,p. 167 - 172
[3]Bulletin de la Societe Chimique de France,1970,p. 3617 - 3624

4
[ 19676-64-3 ]
[ 3117-02-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium peroxymonosulfate; In [D3]acetonitrile; water-d2; at 20℃; for 5h;	General procedure: To an NMR tube, 8.4 mg (50 µmoles) of 1 and 2.2 mg (30 µmoles) of tBuOH (used as an internal standard) in a 750 µL solution of 10% (v/v) d3-ACN in D2O were added. A 1H-NMR spectrum was recorded as a zero point (time = 0). A stock solution of 400 mM Oxone in 10% (v/v) d3-ACN in D2O was prepared and a 250 µL aliquot of the Oxone solution was added to the NMR tube to initiate the reaction. The reaction was followed by 1H-NMR spectroscopy over the course of 5 hrs at room temperature. The yields reported were based on the integration of aromatic peaks against the internal standard. This procedure was repeated for each of the different mol equivalents of Oxone, for the different cosolvents, and substrates.
4.7 g	With ammonium cerium (IV) nitrate; In water; at 20℃; for 1.5h;	A solution of 2,3,4-trimethoybenzaldehyde 12 (9.78 g, 49.8 mmol) in CH2Cl2 (22 mL) was added slowly to a solution of m-CPBA (77 wt%, 12.1 g, 54.0 mmol) in CH2Cl2 (88 mL) at 0 C and the mixture allowed to warm to rt and stirred for 3 h. Saturated aqueous NaHCO3 (100 mL) was then added and the layers separated. The organic phase was washed with 10% (w/v) aqueous Na2S2O3, dried over Na2SO4 and evaporated to provide crude formate ester 13 as a yellow oil. This residue was re-dissolved in MeOH (50 mL), 10% (w/v) aqueous NaOH (50 mL) was added and the mixture stirred at rt for 16 h. The reaction was then acidified to PH 1 using 6.0 M aqueous HCl and diluted with CH2Cl2. The layers were separated and the aqueous phase extracted with CH2Cl2 (4x). The combined organic fraction were dried over MgSO4 and evaporated to provide the crude phenol 14 as orange oil. The material was carried forward without further purification. A solution of ceric ammonium nitrate (71.3 g, 13 mmol) in H2O (65 mL) was added to a flask charged with silica gel (150 g). CH2Cl2 (600 mL) was added, followed by a solution of the above crude product 14 in CH2Cl2 (50 mL) and the mixture stirred at rt for 1.5 h. The silica was then removed by suction filtration, rinsing with CH2Cl2. The layers of the filtrate were separated and the aqueous phase extracted with CH2Cl2 (2x). The combined organic fractions were evaporated. The residue was purified by flash column chromatography (EtOAc / petroleum ether = 1 / 20) to provide 15 as an orange solid (4.70 g, 28.0 mmol, 56 % over three steps from 12). 1H NMR (400 MHz, CDCl3) δ 7.12 (s, 1H), 4.07 (s, 3H), 4.01 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 181.5, 176.5, 145.6, 144.6, 135.7, 135.3, 61.6, 61.3. MS (ESI): m/z 169.2 [M+H]+

Reference： [1]Synthetic Communications,1985,vol. 15,p. 515 - 520
[2]Angewandte Chemie - International Edition,2015,vol. 54,p. 3792 - 3796
Angew. Chem.,2015,vol. 127,p. 3863 - 3867,5
[3]Organic and Biomolecular Chemistry,2017,vol. 15,p. 9903 - 9909
[4]Acta Chimica Hungarica,1985,vol. 120,p. 163 - 166
[5]Journal fur praktische Chemie (Leipzig 1954),1985,vol. 327,p. 808 - 822
[6]Tetrahedron Letters,2013,vol. 54,p. 2344 - 2347
[7]Organic Letters,2018,vol. 20,p. 1597 - 1599
[8]Bioorganic Chemistry,2019,vol. 89

5
[ 30225-80-0 ]
[ 19676-64-3 ]

Reference： [1]Bulletin de la Societe Chimique de France,1970,p. 3617 - 3624
[2]Synthesis,1989,p. 167 - 172

6
[ 19676-64-3 ]
[ 107-30-2 ]
[ 104202-37-1 ]

Reference： [1]Journal fur praktische Chemie (Leipzig 1954),1985,vol. 327,p. 808 - 822

7
[ 19676-64-3 ]
[ 77-78-1 ]
[ 21450-56-6 ]

Yield	Reaction Conditions	Operation in experiment
42 g	With potassium carbonate; In acetone; for 20h;Reflux;	To a solution of <strong>[19676-64-3]2,3,4-trimethoxyphenol</strong> (71g, 0.38mol), K2CO3 (50g, 0.36mol) in acetone (400mL) at room temperature was added dimethvl sulfate (53g, 0.42mol) in 15min. The reaction mixture was stirred and refluxed for 20h, and the solvent was evaporated followed by the addition of water (400mL). The mixture was simply stirred for 15min and allowed to stand at room temperature for 4h. The crude crystalline product formed and was collected, washed with water and purified by recrystallization from MeOH to afford 1,2,3,4-tetramethoxybenzene 45 (42g) as white solid. Total yield (from step 1 to 3): 70.6%. Mp 85.8-86.1C (lit [70]. mp 87-87.5C). TLC: Rf=0.75 (1:5 EtOAc/hexanes). 1H NMR (600MHz, Chloroform-d) δ 6.58 (s, 2H), 3.90 (s, 6H), 3.82 (s, 6H). 13C NMR (151MHz, Chloroform-d) δ 147.91, 143.52, 106.53, 61.33, 56.52. HRMS (+ESI) 199.0968 [M+ H]+, 221.0788 [M+ Na]+ (calcd. for C10H15O4+ 199.0965 and C10H14O4Na+ 221.0784).

Reference： [1]Tetrahedron,1980,vol. 36,p. 123 - 129
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640
[3]Australian Journal of Chemistry,2000,vol. 53,p. 749 - 754
[4]Heterocycles,1982,vol. 19,p. 691 - 695
[5]Bulletin de la Societe Chimique de France,1970,p. 3617 - 3624
[6]Journal of the Chemical Society. Perkin transactions I,1987,p. 2017 - 2022
[7]European Journal of Medicinal Chemistry,2019,vol. 183

8
[ 41038-42-0 ]
[ 19676-64-3 ]

Reference： [1]Journal of Organic Chemistry,1986,vol. 51,p. 5436 - 5439

9
[ 30225-82-2 ]
[ 19676-64-3 ]

Yield	Reaction Conditions	Operation in experiment
2.22 g	With sodium hydroxide; In methanol; at 0℃; for 1.5h;	To a stirred solution of 2,3,4-trimethoxybenzaldehyde (3.0 g, 15.3 mmol) in DCM (60 mL) was added a solution of mCPBA (3.26 g, 18.9 mmol) dissolved in DCM (60 mL). After 5 h, the solvent was concentrated to half its volume and filtered to remove the precipitated m-chlorobenzoic acid. The filtrate was then washed with 5% aq. NaHCO3, water and sat. NaCl. The solvent was subsequently removed under reduced pressure to afford an oily residue. This was re-dissolved in methanol (30 mL) and 2.5M aq. NaOH (25 mL) was added to the solution at 0 C. After 1.5 h, the reaction was acidified with 2M aq. HCl and the product was isolated by extraction with ether (320 mL). The combined organic layers were dried under sodium sulphate, filtered and concentrated to an oil. This was purified by flash column chromatography (stationary phase: silica gel; mobile phase: hexane/ethyl acetate 2:1). All homogenous fractions were collected and the solvent was removed in vacuo to afford 13.1 as a yellow solid (2.22 g, 79%). The phenol 13.1 (1.5 g, 8.15 mmol) was re-dissolved in acetone (40 mL) and K2CO3 (5.0 g, 36.2 mmol) was subsequently added followed by ethyl bromoacetate (2 mL, 17.3 mmol). The reaction was refluxed for 12 h. On completion, the solvent was concentrated in vacuo and a solution of sat. NaCl (40 mL) was added. The product was extracted using diethyl ether (330 mL), dried under sodium sulphate, filtered and concentrated to an oil. It was purified by flash column chromatography (stationary phase: silica gel; mobile phase: hexane/ethyl acetate 5:1). All homogenous fractions were collected and the solvent was removed in vacuo to afford 13.2 as a yellow oil (1.67 g, 76%).
	With sodium hydroxide; In methanol; water; at 0 - 20℃; for 16h;	A solution of 2,3,4-trimethoybenzaldehyde 12 (9.78 g, 49.8 mmol) in CH2Cl2 (22 mL) was added slowly to a solution of m-CPBA (77 wt%, 12.1 g, 54.0 mmol) in CH2Cl2 (88 mL) at 0 C and the mixture allowed to warm to rt and stirred for 3 h. Saturated aqueous NaHCO3 (100 mL) was then added and the layers separated. The organic phase was washed with 10% (w/v) aqueous Na2S2O3, dried over Na2SO4 and evaporated to provide crude formate ester 13 as a yellow oil. This residue was re-dissolved in MeOH (50 mL), 10% (w/v) aqueous NaOH (50 mL) was added and the mixture stirred at rt for 16 h. The reaction was then acidified to PH 1 using 6.0 M aqueous HCl and diluted with CH2Cl2. The layers were separated and the aqueous phase extracted with CH2Cl2 (4x). The combined organic fraction were dried over MgSO4 and evaporated to provide the crude phenol 14 as orange oil. The material was carried forward without further purification. A solution of ceric ammonium nitrate (71.3 g, 13 mmol) in H2O (65 mL) was added to a flask charged with silica gel (150 g). CH2Cl2 (600 mL) was added, followed by a solution of the above crude product 14 in CH2Cl2 (50 mL) and the mixture stirred at rt for 1.5 h. The silica was then removed by suction filtration, rinsing with CH2Cl2. The layers of the filtrate were separated and the aqueous phase extracted with CH2Cl2 (2x). The combined organic fractions were evaporated. The residue was purified by flash column chromatography (EtOAc / petroleum ether = 1 / 20) to provide 15 as an orange solid (4.70 g, 28.0 mmol, 56 % over three steps from 12
71 g	With sodium hydroxide; In water; at 0 - 40℃; for 2h;	Crude 2,3,4-trimethoxyphenyl formate (73g) was added to methanol (120mL) and treated with aq. 10% NaOH (300mL) at 0C. The resulting homogeneous solution was stirred and allowed to warm to 40C for 2h and determined to be complete by TLC. Methanol was distilled out completely from the reaction mixture under reduced pressure. The residue was added to H2O (200mL), acidified with 3N HCI and extracted with DCM (3×150mL). The organic layer was washed with H2O (2×200mL), dried over Na2SO4, filtered and concentrated completely under reduced pressure to yield 2,3,4-trimethoxyphenol (71g) as a white solid (wet). TLC: Rf=0.50 (1:5 EtOAc/hexanes). This material was used for the subsequent reaction without further purification.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 3759 - 3763
[2]Tetrahedron,2005,vol. 61,p. 10061 - 10072
[3]Bulletin de la Societe Chimique de France,1970,p. 3617 - 3624
[4]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640
[5]Chemical Communications,2011,vol. 47,p. 2868 - 2870
[6]Patent: US2015/18566,2015,A1 .Location in patent: Paragraph 0413; 0414; 0415
[7]Organic Letters,2018,vol. 20,p. 1597 - 1599
[8]Organic Process Research and Development,2019,vol. 23,p. 595 - 602
[9]Bioorganic Chemistry,2019,vol. 89
[10]European Journal of Medicinal Chemistry,2019,vol. 183
[11]Tetrahedron,2022

10
[ 19676-64-3 ]
Q₄FA₁₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640

11
[ 19676-64-3 ]
Q₄FA₁₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640

12
[ 19676-64-3 ]
Q₄FA₁₅ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640

13
[ 19676-64-3 ]
Q₄FA₁₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640

14
[ 19676-64-3 ]
Q₄FA₁₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640

15
[ 19676-64-3 ]
[ 25245-39-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2637 - 2640
[2]Tetrahedron,1980,vol. 36,p. 123 - 129

16
[ 19676-64-3 ]
[ 857674-57-8 ]

Reference： [1]Organic Letters,2005,vol. 7,p. 2417 - 2420
[2]Journal of Natural Products,2014,vol. 77,p. 1817 - 1824
[3]Tetrahedron,2022

17
[ 19676-64-3 ]
2-(4,5-dimethoxy-3,6-dioxo-cyclohexa-1,4-dienyl)-benzoic acid [ No CAS ]