[ CAS No. 2206-43-1 ] {[proInfo.proName]}

Name: 2206-43-1|4-Methoxyisophthalic acid|98%
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Product Details of [ 2206-43-1 ]

CAS No. :	2206-43-1	MDL No. :	MFCD06208422
Formula :	C₉H₈O₅	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JIICYHFLIOGGHE-UHFFFAOYSA-N
M.W :	196.16	Pubchem ID :	75152
Synonyms :

Safety of [ 2206-43-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 2206-43-1 ]

* 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 [ 2206-43-1 ]

[ 2206-43-1 ] Synthesis Path-Downstream 1~57

1
[ 908094-01-9 ]
[ 2206-43-1 ]
[ 22955-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	With diethyl ether

Reference： [1]Kawano [Chemical and pharmaceutical bulletin, 1959, vol. 7, p. 698,700] Sprengling; Freeman [Journal of the American Chemical Society, 1950, vol. 72, p. 1982,1983]
[2]Bonner,W.A.; De Graw,J.I. [Tetrahedron, 1962, vol. 18, p. 1295 - 1309]

2
[ 60736-71-2 ]
[ 2206-43-1 ]

Reference： [1]Izvestiya Akademii Nauk Armyanskoi SSR, Nauki o Zemle,1955,vol. 8,p. 29,33
Chem.Abstr.,1956,p. 11982
[2]Journal of Organic Chemistry,1951,vol. 16,p. 457,458

3
[ 52577-09-0 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate
	Multi-step reaction with 2 steps 1: aqueous HNO₃ 2: aqueous potassium permanganate solution
	Multi-step reaction with 3 steps 1: aqueous H₂SO₄ 2: Na₂Cr₂O₇; aqueous H₂SO₄ 3: aqueous potassium permanganate solution

With potassium hydroxide; potassium permanganate

Reference： [1]Quelet; Allard [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1937, vol. 205, p. 238]
[2]Reichert; Auf dem Kampe [Archiv der Pharmazie, 1939, vol. 277, p. 261,266]
[3]Reichert; Auf dem Kampe [Archiv der Pharmazie, 1939, vol. 277, p. 261,266]
[4]Location in patent: body text Novikova; Kilimenchuk; Yarkova; Meshkova; Topilova [Russian Journal of Applied Chemistry, 2008, vol. 81, # 9, p. 1602 - 1607]

4
[ 6738-23-4 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
49.56%	With potassium permanganate; In water; at 70 - 80℃;	To a solution the 1-methoxy-2,4-dimethyl benzene (4)(2.41 g, 17.72 mmol) in H2O at 70 C was added potassiumpermanganate (22.40 g, 0.14 mol). The reaction wasallowed to warm to 80 C until the disappearance of compound(4). Then the mixture was filtered and the solidwashed with dichloromethane (CH2Cl2) (2 × 20 mL). Theorganic layer was washed with brine (20 mL) and dried overMgSO4. The resulting solution was recovered undervacuum to give 4-methoxy-1,3-phthalic acid (5) (1.72 g,yield 49.56%).

Reference： [1]Medicinal Chemistry Research,2019,vol. 28,p. 1413 - 1424
[2]Chemische Berichte,1878,vol. 11,p. 900
Chemische Berichte,1880,vol. 13,p. 1554

5
[ 6880-04-2 ]
[ 2206-43-1 ]

Reference： [1]Chemische Berichte,1879,vol. 12,p. 818,821

6
[ 25045-36-7 ]
[ 2206-43-1 ]

Reference： [1]Chemische Berichte,1879,vol. 12,p. 818,821

7
[ 25445-34-5 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate
	With potassium permanganate
	With potassium permanganate

Reference： [1]Quelet; Anglade [Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1936, vol. 203, p. 262][Bulletin de la Societe Chimique de France, 1936, vol. <5> 3, p. 2200]
[2]Liu, Xiu Jie; Shi, Xin Xin; Zhong, Yong Liang; Liu, Ning; Liu, Kai [Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 21, p. 6591 - 6595,5]
[3]Xiu-jie, Liu; Chao-qing, Wang; Jie, Meng; xin-xin, Shi; ya-nan, Yan; Xu-guang, Liu [Medicinal Chemistry Research, 2018, vol. 27, # 2, p. 488 - 496] Liu, Xiujie; Wang, Yan; Liu, Lili; Chen, Guangling [Medicinal Chemistry Research, 2018, vol. 27, # 8, p. 1971 - 1983]

8
[ 2206-43-1 ]
[ 636-46-4 ]

Reference： [1]Chemische Berichte,1878,vol. 11,p. 900
Chemische Berichte,1880,vol. 13,p. 1554
[2]Chemische Berichte,1879,vol. 12,p. 818,821
[3]Chemische Berichte,1879,vol. 12,p. 818,821

9
[ 2206-43-1 ]
[ 13235-60-4 ]

Yield	Reaction Conditions	Operation in experiment
98.78%	With thionyl chloride at 80℃; for 8h;	Synthesis of 4-methoxy-1,3-benzene dichloride (6) 4-Methoxy-1,3-phthalic acid (5) (1.00 g, 5.10 mmol) wasdissolved in excess quantity of thionyl chloride (10 mL) andallowed to reflux for 8 h at 80 °C. The excess of thionylchloride was recovered under vacuum to give 4-methoxy-1,3-benzenedichloride (6) (1.17 g, yield 98.78%).
68.7%	With thionyl chloride; N,N-dimethyl-formamide
	With thionyl chloride

	With thionyl chloride
	With thionyl chloride for 5h; Reflux;	1.4 4-methoxyisophthalic acid (1.0 g, 5.1 mmol) and thionyl chloride (8 mL) were added to the round bottom flask. After refluxing for 5 h, the excess of thionyl chloride was distilled off under reduced pressure and treated with toluene 15 mL) was removed twice to remove the residual thionyl chloride to give 4-methoxyisophthaloyl chloride, add anhydrous CH2Cl2(15 mL) was dissolved and allowed to stand.
	With thionyl chloride
	With thionyl chloride In N,N-dimethyl-formamide at 80℃; for 6h;	4 Example 4 Synthesis of Picotamide (4) Add 2.3g of 4-methoxyisophthalic acid, 20mL of thionyl chloride, a few drops of N, N-After dimethylformamide, heat to reflux under stirring at 80C.The upper part of the spherical condenser is connected to a gas recovery device to remove the acid gasPass into the sodium hydroxide aqueous solution.After refluxing for 6 hours, the 4-methoxyisophthalic acid reaction was complete.Rotary evaporation to remove thionyl chloride,A viscous 4-methoxyisophthaloyl chloride substrate was obtained in a single-neck bottle.2.83g (26mmol) 3-aminomethylpyridine, 1.5g(26mmol) iron powder was placed in 50mL anhydrous toluene.Dissolve the viscous substrate in 10mL of anhydrous toluene, and slowly drip it under ice bathA toluene solution of 3-aminomethylpyridine.During the dropping process, bubbles were generated in the reaction liquid, accompanied by solid precipitation.DripAfter finishing, continue to stir under ice bath for 30 minutes and then change to room temperature stirring.The reaction solution gradually changed from dark black to white milkTurbid liquid.After stirring for 2 hours, the reaction was complete.After filtering, the filtrate was washed with saturated sodium bicarbonate solution and distilled water. Sodium sulfatedry.Sodium sulfate was removed by filtration, and toluene was removed under reduced pressure to obtain 4.17 g of light yellow solid.Light yellow crude product is recrystallized in ethanol3.94g white solid (87% yield, 99% purity).

Reference： [1]Chen, Guangling; Wang, Chaoqing; Zhang, Zhihao; Liu, Xiujie [Medicinal Chemistry Research, 2019, vol. 28, # 9, p. 1413 - 1424]
[2]Location in patent: body text Novikova; Kilimenchuk; Yarkova; Meshkova; Topilova [Russian Journal of Applied Chemistry, 2008, vol. 81, # 9, p. 1602 - 1607]
[3]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]
[4]Liu, Xiu Jie; Shi, Xin Xin; Zhong, Yong Liang; Liu, Ning; Liu, Kai [Bioorganic and medicinal chemistry letters, 2012, vol. 22, # 21, p. 6591 - 6595,5]
[5]Current Patent Assignee: ANHUI UNIVERSITY OF CHINESE MEDICINE; HEFEI YIGONG MEDICINE - CN103664804, 2016, B Location in patent: Paragraph 0030; 0041; 0042
[6]Xiu-jie, Liu; Chao-qing, Wang; Jie, Meng; xin-xin, Shi; ya-nan, Yan; Xu-guang, Liu [Medicinal Chemistry Research, 2018, vol. 27, # 2, p. 488 - 496]
[7]Current Patent Assignee: CHANGZHOU VOCATIONAL INSTITUTE OF ENGINEERING - CN112159347, 2021, A Location in patent: Paragraph 0027; 0036-0038

10
[ 7083-19-4 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate

Reference： [1]Gray; Bonner [Journal of the American Chemical Society, 1948, vol. 70, p. 1249,1250]

11
[ 15471-26-8 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium permanganate

Reference： [1]Sprengling; Freeman [Journal of the American Chemical Society, 1950, vol. 72, p. 1982,1983]

12
[ 124-38-9 ]
[ 38474-03-2 ]
[ 2206-43-1 ]
[ 1951-38-8 ]

Reference： [1]Tetrahedron,1990,vol. 46,p. 861 - 884

13
[ 7722-84-1 ]
[ 548-19-6 ]
[ 2206-43-1 ]
[ 100-09-4 ]

Reference： [1]Baker et al. [Journal of the Chemical Society, 1963, p. 1477,1487]

14
[ 106-44-5 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 2 percent Chromat_. / 15 h / 176 °C 2: 20.6 percent Chromat_. / 72 h / 170 °C 3: 86 percent / potassium carbonate / acetone / 4 h / Heating 4: potassium permanganate, sodium hydroxide / H₂O / 3 h / Heating
	Multi-step reaction with 3 steps 1: 48 percent Chromat_. / 15 h / 176 °C 2: 86 percent / potassium carbonate / acetone / 4 h / Heating 3: potassium permanganate, sodium hydroxide / H₂O / 3 h / Heating

Reference： [1]Pinhey, John T.; Xuan, Phan Thanh [Australian Journal of Chemistry, 1988, vol. 41, # 1, p. 69 - 80]
[2]Pinhey, John T.; Xuan, Phan Thanh [Australian Journal of Chemistry, 1988, vol. 41, # 1, p. 69 - 80]

15
[ 70347-04-5 ]
[ 2206-43-1 ]

Reference： [1]Chemische Berichte,1879,vol. 12,p. 818,821

16
[ 76646-42-9 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Na₂Cr₂O₇; aqueous H₂SO₄ 2: aqueous potassium permanganate solution

Reference： [1]Reichert; Auf dem Kampe [Archiv der Pharmazie, 1939, vol. 277, p. 261,266]

17
[ 100-66-3 ]
[ 2206-43-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 10 - 12 °C / Einleiten von HCl, zuletzt bei 60grad 2: aqueous potassium permanganate solution
	Multi-step reaction with 2 steps 1: hydrogenchloride / benzene 2: potassium permanganate
	Multi-step reaction with 2 steps 1: hydrogenchloride / toluene 2: potassium permanganate

18
[ 2206-43-1 ]
[ 22955-73-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

19
[ 2206-43-1 ]
[ 16357-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

20
[ 2206-43-1 ]
4-methoxy-isophthalic acid bis-(2-diethylamino-ethyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

21
[ 2206-43-1 ]
4-methoxy-isophthalic acid bis-(3-diethylamino-propyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

22
[ 2206-43-1 ]
4-methoxy-isophthalic acid bis-(2-dipropylamino-ethyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

23
[ 2206-43-1 ]
4-methoxy-isophthalic acid bis-(3-dipropylamino-propyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

24
[ 2206-43-1 ]
4-methoxy-isophthalic acid bis-(2-dibutylamino-ethyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

25
[ 2206-43-1 ]
4-methoxy-isophthalic acid bis-(3-dibutylamino-propyl ester) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: benzene

Reference： [1]Fosdick; Fancher [Journal of the American Chemical Society, 1941, vol. 63, p. 1278]

26
[ 7664-93-9 ]
[ 2206-43-1 ]
[ 479579-02-7 ]

Yield	Reaction Conditions	Operation in experiment
52 g (91%)	With sodium bicarbonate In methanol; ice-water; water	1 Methyl 4-Methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate (Formula 4) EXAMPLE 1 Methyl 4-Methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate (Formula 4) To 50 g of 4-methoxy-1,3-benzenedicarboxylic acid (formula 2) dissolved in 400 ml of methanol there were added 18 ml of concentrated sulphuric acid, d 1.84, and the mixture was boiled at reflux for 7 hours. The mixture was poured into 600 ml of ice-water. The precipitated 4-methoxy-1,3-benzenedicarboxylic acid dimethyl ester (formula 3) was collected, washed by suspending in a solution of sodium hydrogen carbonate and then in water, and dried, yielding 52 g (91%) of compound 4 as a white solid, m.p. 96-97° C. It showed in 1-NMR in DMSO-d6 δ 3.84 (s, 3H, COOMe); 3.95 (s, 3H, PhOMe); 3.96 (s, 3H, COOMe); 7.28 (d, 1H, Ha), 8.1 (dd, 1H, Hb); 8.2 (d, 1H, Hc).

Reference： [1]Current Patent Assignee: Casagrande, Cesare - US6525078, 2003, B1

27
[ 7664-93-9 ]
[ 2206-43-1 ]
[ 28045-71-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium bicarbonate In methanol	3 4-Methoxy-N1-4-trans-hydroxycyclohexyl-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide (Formula 6) EXAMPLE 3 4-Methoxy-N1-4-trans-hydroxycyclohexyl-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide (Formula 6) 4-Methoxy-1,3-benzenedicarboxylic acid 3-monomethyl ester (formula 7) was prepared by adding at 20° C. under stirring 12 ml of concentrated sulphuric acid, d 1.84, to a suspension of 50 g of 4-methoxyisophthalic acid in 400 ml of methanol; stirring was then continued for 1 hour and then the mixture was poured into ice-water (400 ml). The precipitate was collected and stirred with a saturated solution of sodium hydrogen carbonate; the insoluble residue (15 g) was constituted by 4-methoxy-1,3-benzenedicarboxylic acid dimethyl ester.
	With sodium bicarbonate In methanol	3 4-Methoxy-N1-4- trans -hydroxycyclohexyl-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide (formula 6) Example 3 4-Methoxy-N1-4- trans -hydroxycyclohexyl-N3-(3-pyridinylmethyl)-1,3-benzenedicarboxamide (formula 6) 4-Methoxy-1,3-benzenedicarboxylic acid 3-monomethyl ester (formula 7) was prepared by adding at 20 °C under stirring 12 ml of concentrated sulphuric acid, d 1.84, to a suspension of 50 g of 4-methoxyisophthalic acid in 400 ml of methanol; stirring was then continued for 1 hour and then the mixture was poured into ice-water (400 ml). The precipitate was collected and stirred with a saturated solution of sodium hydrogen carbonate; the insoluble residue (15 g) was constituted by 4-methoxy-1,3-benzenedicarboxylic acid dimethyl ester.

Reference： [1]Current Patent Assignee: Casagrande, Cesare - US6525078, 2003, B1
[2]Current Patent Assignee: Casagrande, Cesare - EP1270558, 2003, A1

28
[ 7664-93-9 ]
[ 2206-43-1 ]
[ 479579-02-7 ]
[ 22955-73-3 ]

Yield	Reaction Conditions	Operation in experiment
52 g (91%)	In methanol; ice-water	1 Methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate (formula 4) Example 1 Methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate (formula 4) To 50 g of 4-methoxy-1,3-benzenedicarboxylic acid (formula 2) dissolved in 400 ml of methanol there were added 18 ml of concentrated sulphuric acid, d 1.84, and the mixture was boiled at reflux for 7 hours. The mixture was poured into 600 ml of ice-water. The precipitated 4-methoxy-1,3-benzenedicarboxylic acid dimethyl ester (formula 3) was collected, washed by suspending in a solution of sodium hydrogen carbonate and then in water, and dried, yielding 52 g (91%) of compound 4 as a white solid, m.p. 96-97°C. It showed in 1-NMRin DMSO-d6δ 3.84 (s, 3H, COOMe);3.95 (s, 3H, PhOMe);3.96 (s, 3H,COOMe);7.28 (d, 1H, Ha); 8.1 (dd, 1H, Hb); 8.2 (d. 1H, Hc) It was then dissolved in 150 ml of 3-pyridinylmethylamine and heated at 70°C for 40 hours. Thereafter most of the excess amine was recovered by distillation in a vacuum. The residue was mixed with ice-water, acidified (pH 5) with diluted hydrochloric acid and extracted with chloroform. The extracts were dried with anhydrous sodium sulphate and evaporated, and the residue was taken up with light petroleum, b.p. 70-80°C, yielding 43.8 g(63 %) of methyl 4-methoxy-3-(3-pyridinylmethylaminocarbonyl)benzoate (formula 4) as a white solid, the 1H-NMR spectrum of which in CDCl3showed signals at δ 3.91 (s, 3H, COOMe),4.03 (s, 3H, PhOMe),4.72 (d, 2H, PyCH2); 7.05 (d, 1H,Ha); 7.31 (m, 1H, Hb,Py); 7.74 (m, 1H, Hc,Py); 8.1 (broad t, 1H, CONH); 8.19 (dd, 1H, Hb); 8.55 (broad m, 1H, Ha,Py); 8.62 (broad m, 1H, Hd,Py); 8.9 (d, 1H,Hc).

Reference： [1]Current Patent Assignee: Casagrande, Cesare - EP1270558, 2003, A1

29
[ 2206-43-1 ]
[ 1029440-58-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: thionyl chloride 2: pyridine / tetrahydrofuran / 8 h / 20 °C