[ CAS No. 2150-41-6 ] {[proInfo.proName]}

Name: 2150-41-6|Methyl 2,4-dimethoxybenzoate|98%
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Product Details of [ 2150-41-6 ]

CAS No. :	2150-41-6	MDL No. :	MFCD00070649
Formula :	C₁₀H₁₂O₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	IHIJFZWLGPEYPJ-UHFFFAOYSA-N
M.W :	196.20	Pubchem ID :	137451
Synonyms :

Safety of [ 2150-41-6 ]

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 [ 2150-41-6 ]

* 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 [ 2150-41-6 ]
Downstream synthetic route of [ 2150-41-6 ]

[ 2150-41-6 ] Synthesis Path-Upstream 1~8

1
[ 67-56-1 ]
[ 91-52-1 ]
[ 7314-44-5 ]
[ 2150-41-6 ]

Reference： [1] Synthesis, 2011, # 9, p. 1375 - 1382

2
[ 2150-41-6 ]
[ 5446-02-6 ]

Reference： [1] Journal of Chemical Research, 2010, # 4, p. 222 - 227

3
[ 2150-47-2 ]
[ 74-88-4 ]
[ 2150-41-6 ]
[ 5446-02-6 ]

Reference： [1] Asian Journal of Chemistry, 2014, vol. 26, # 3, p. 702 - 708

4
[ 99-50-3 ]
[ 89-86-1 ]
[ 149-91-7 ]
[ 99-10-5 ]
[ 303-38-8 ]
[ 490-79-9 ]
[ 99-06-9 ]
[ 69-72-7 ]
[ 74-88-4 ]
[ 99-96-7 ]
[ 2150-41-6 ]
[ 606-45-1 ]
[ 5368-81-0 ]
[ 121-98-2 ]
[ 2150-38-1 ]
[ 1916-07-0 ]
[ 2150-42-7 ]
[ 2150-40-5 ]
[ 2150-37-0 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 14, p. 1694 - 1697

5
[ 865-33-8 ]
[ 106614-28-2 ]
[ 128272-26-4 ]
[ 2150-41-6 ]
[ 204707-42-6 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044

6
[ 124-41-4 ]
[ 106614-28-2 ]
[ 128272-26-4 ]
[ 2150-41-6 ]
[ 204707-42-6 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044

7
[ 865-33-8 ]
[ 106614-28-2 ]
[ 128272-26-4 ]
[ 2150-41-6 ]
[ 204707-42-6 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044

8
[ 124-41-4 ]
[ 106614-28-2 ]
[ 128272-26-4 ]
[ 2150-41-6 ]
[ 204707-42-6 ]

Reference： [1] Tetrahedron Letters, 2010, vol. 51, # 23, p. 3041 - 3044

[ 2150-41-6 ] Synthesis Path-Downstream 1~56

1
[ 90-24-4 ]
[ 2150-41-6 ]
[ 65612-84-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	Stage #1: 2-hydroxy-4,6-dimethoxyacetophenone With lithium hexamethyldisilazane In tetrahydrofuran at -78 - -10℃; for 2h; Inert atmosphere; Stage #2: methyl 2, 4-dimethoxybenzoate With N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran for 24h; Inert atmosphere; Reflux;	1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(2,4-dimethoxyphenyl)propane-1,3-dione (10) In a 200-mL two-necked round-bottomed flask equipped with a magnetic stirring bar, a rubber septum,and an argon balloon was placed LHMDS in THF (39 mL, 51.0 mmol, 1.3 M) at -78 oC, and to it wasadded 12 (2.00 g, 10.2 mmol) in THF (51 mL). After the mixture was stirred for 1 h at -78 oC and warmedto -10 oC for 1 h, to it were added methyl 2,4-dimethoxybenzoate 11 (2.00 g, 10.2 mmol) in THF (51 mL)and TMEDA (7.6 mL, 51.0 mmol), and the whole mixture was heated at reflux for 24 h. The reaction wasquenched reversely by pouring the solution into ice water and 2N HCl (50 mL), and the mixture wasextracted with CHCl3 (20 mL x 3). The combined extracts were washed with sat. NaCl aq. (30 mL) anddried over anhydrous Na2SO4, and concentrated in vacuo to give a crude product, which was purified bysilica gel column chromatography (n-hexane/EtOAc = 4 / 1) to give the title compound 10 (3.15 g, 86%).Yield 86%, keto : enol = 48:52; Yellow solid; mp 108-109 ; 1H NMR (500 MHz, CDCl3) δ3.59 (s,1.44H), 3.77 (s, 1.44H), 3.80 (s, 1.44H), 3.81 (s, 1.56H), 3.86 (s, 1.44H), 3.86 (s, 1.56H), 3.89 (s, 1.56H),3.94 (s, 1.56H), 4.51 (s, 0.96H), 5.86 (d, J = 2.5 Hz, 0.48H), 5.97 (d, J = 2.5 Hz, 0.52H), 6.07 (d, J = 2.5Hz, 0.48H), 6.09 (d, J = 2.5 Hz, 0.52H), 6.44 (d, J = 2.5 Hz, 0.48H), 6.50 (d, J = 2.5 Hz, 0.52H), 6.56 (dd, J = 2.5, 8.6 Hz, 0.48H), 6.58 (dd, J = 2.5, 8.6 Hz, 0.52H), 7.65 (s, 0.52H), 7.93 (d, J = 8.6 Hz, 0.48H),7.95 (d, J = 8.6 Hz, 0.52H), 13.5 (s, 0.52H), 13.7 (s, 0.48H); 13C NMR (125 MHz, CDCl3) δ55.3, 55.4,55.5, 55.5, 55.6, 55.6, 59.7, 90.8, 91.3, 93.7, 94.1, 98.2, 98.9, 101.8, 104.8, 105.1, 105.5, 105.7, 116.1,120.1, 131.5, 132.9, 160.2, 160.9, 161.7, 162.2, 163.5, 164.8, 165.0, 166.2, 166.6, 167.6, 174.3, 193.3,193.4, 200.0; IR (neat)2942, 2844, 1658, 1597, 1290, 1215, 1159, 1114, 1027, 822 cm-1; HRMS(EI)Calcd for C19H20O7(M)+ 360.1209, found 360.1200.
	With sodium

Reference： [1]Mizota, Isao; Taniguchi, Kana; Shimizu, Makoto [Heterocycles, 2016, vol. 93, # 1, p. 310 - 322]
[2]Doporto et al. [Journal of the Chemical Society, 1955, p. 4249,4253]

2
[ 2150-41-6 ]
[ 91-52-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium hydroxide
	Stage #1: methyl 2, 4-dimethoxybenzoate With sodium hydroxide; water In ethanol at 25 - 40℃; for 2h; Stage #2: With hydrogenchloride In ethanol; chloroform; water	10 Reference Example 10 53 g of methyl 2,4-dimethoxybenzoate was dissolved in 160 ML of ethanol, to which 104 ML of a 5M aqueous solution of sodium hydroxide was added, and this mixture was stirred for 2 hours at 25 to 40°C. Then, chloroform and water were added to the reaction mixture, which was adjusted to PH 2 with 6M hydrochloric acid, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure to yield 45 g of 2,4-dimethoxybenzoic acid as white solid. NMR(90MHz,CDCl3) δ value: 3.88(3H,s), 4.04(3H,s), 6.53-6.69(2H,m), 8.11(1H,d,J=8.5Hz), 10.34(1H,br)
	Stage #1: methyl 2, 4-dimethoxybenzoate In water Reflux; Stage #2: With hydrogenchloride In water

Reference： [1]Van Otterlo, Willem A. L.; Michael, Joseph P.; De Koning, Charles B. [Synthetic Communications, 2007, vol. 37, # 20, p. 3611 - 3621]
[2]Perkin; Smith [Journal of the Chemical Society, 1904, vol. 85, p. 159] Herzig; Wenzel; Batscha [Monatshefte fur Chemie, 1903, vol. 24, p. 890]
[3]Herzig; Wenzel; Batscha [Monatshefte fur Chemie, 1903, vol. 24, p. 890]
[4]Current Patent Assignee: SHUNICHI SHIOZAWA - EP1445249, 2004, A1 Location in patent: Page 118
[5]Mandle, Richard J.; Cowling, Stephen J.; Goodby, John W. [Chemistry - A European Journal, 2017, vol. 23, # 58, p. 14554 - 14562]

3
[ 2150-41-6 ]
[ 104-47-2 ]
[ 132593-12-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With sodium hydride In tetrahydrofuran; mineral oil at 60℃; for 48h;
	With sodium ethanolate; benzene
	With sodium hydride In tetrahydrofuran at 60℃; Inert atmosphere;

Reference： [1]Hudson, Sean A.; Surade, Sachin; Coyne, Anthony G.; Mclean, Kirsty J.; Leys, David; Munro, Andrew W.; Abell, Chris [ChemMedChem, 2013, vol. 8, # 9, p. 1451 - 1456]
[2]Kawase [Bulletin of the Chemical Society of Japan, 1958, vol. 31, p. 390,392]
[3]Kavanagh, Madeline E.; Coyne, Anthony G.; McLean, Kirsty J.; James, Guy G.; Levy, Colin W.; Marino, Leonardo B.; De Carvalho, Luiz Pedro S.; Chan, Daniel S. H.; Hudson, Sean A.; Surade, Sachin; Leys, David; Munro, Andrew W.; Abell, Chris [Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3272 - 3302]

4
[ 89-86-1 ]
[ 77-78-1 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate
	With potassium hydroxide at 50℃;
	With potassium hydroxide

	With potassium carbonate In DMF (N,N-dimethyl-formamide) at 70 - 115℃; for 10.5h;	9 Reference Example 9 50 g of 2,4-dihydroxybenzoic acid, 269 g of potassium carbonate, 123 ML of dimethyl sulfate, and 500 ML of N,N-dimethylformamide were suspended together, and this suspension was stirred for 6.5 hours at 70 to 80°C. Further, 90 g of potassium carbonate and 61 ML of dimethyl sulfate were added to this suspension, which was stirred for another 4 hours at 110 to 115°C. This reaction mixture was added to a mixture of ethyl acetate and water, and adjusted to PH 2 with 6M hydrochloric acid, and then the organic phase was separated therefrom.. After the resultant organic phase was washed with water and a saturated sodium chloride solution successively, the washed phase was dried over anhydrous magnesium sulfate, and the solvent was distilled out under reduced pressure.. The resultant residue was purified by silica gel column chromatography [eluent; hexane:ethyl acetate=1:2] to yield 54 g of methyl 2,4-dimethoxybenzoate as yellow oil. NMR(90MHz,CDCl3) δ value: 3.85(6H,s), 3.89(3H,s), 6.42-6.55(2H,m), 7.85(1H,d,J=9.3Hz)
	With potassium carbonate In acetone

Reference： [1]Van Otterlo, Willem A. L.; Michael, Joseph P.; De Koning, Charles B. [Synthetic Communications, 2007, vol. 37, # 20, p. 3611 - 3621]
[2]Cullinane; Algar; Ryan [Scientific Proceedings of the Royal Dublin Society, 1928, vol. 19, p. 79][Chemisches Zentralblatt, 1929, vol. 100, # II, p. 1919]
[3]Perkin; Smith [Journal of the Chemical Society, 1904, vol. 85, p. 159]
[4]Current Patent Assignee: SHUNICHI SHIOZAWA - EP1445249, 2004, A1 Location in patent: Page 118
[5]Brel, V. K.; Mikulenkova, E. A.; Mironov, V. F.; Tatarinov, D. A.; Terekhova, N. V. [Russian Chemical Bulletin, 2020, vol. 69, # 11, p. 2147 - 2152][Izv. Akad. Nauk, Ser. Khim., 2020, # 11, p. 2147 - 2152,6]

5
[ 908094-01-9 ]
[ 124-38-9 ]
[ 51241-41-9 ]
[ 2150-41-6 ]
[ 2065-27-2 ]

Yield	Reaction Conditions	Operation in experiment
	Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;

Reference： [1]Cabiddu, Salvatore; Maccioni, Antonio; Piras, Pier Paolo; Plumitallo, Antonio [Gazzetta Chimica Italiana, 1981, vol. 111, # 3/4, p. 123 - 128]

6
[ 186581-53-3 ]
[ 124-38-9 ]
[ 79128-08-8 ]
[ 2150-41-6 ]
[ 2065-27-2 ]

Reference： [1]Gazzetta Chimica Italiana,1981,vol. 111,p. 123 - 128

7
[ 5446-02-6 ]
[ 77-78-1 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate In acetone for 24h; Heating;

Reference： [1]Anderson, Wayne K.; Boehm, Terri L.; Makara, Gergely M.; Swann, R. Thomas [Journal of Medicinal Chemistry, 1996, vol. 39, # 1, p. 46 - 55]

8
[ 2150-41-6 ]
[ 141-97-9 ]
5-(2,4-dimethoxy-phenyl)-3,5-dioxo-pentanoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With N,N,N,N,-tetramethylethylenediamine; lithium diisopropyl amide In tetrahydrofuran; hexane at -78 - 20℃;

Reference： [1]Douglas, Christopher J.; Sklenicka, Heather M.; Shen, Hong C.; Mathias, David S.; Degen, Shane J.; Golding, Geoffrey M.; Morgan, Christopher D.; Shih, Regina A.; Mueller, Kristen L.; Seurer, Lisa M.; Johnson, Erik W.; Hsung, Richard P. [Tetrahedron, 1999, vol. 55, # 48, p. 13683 - 13696]

9
[ 2150-41-6 ]
[ 70430-05-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: benzene; diethyl ether / 2 h / Heating 2: H₂ / 10percent Pd/C / ethanol; H₂O / 48 h / 3102.9 Torr

Reference： [1]MacKnight, Earl; McClelland, Robert A. [Canadian Journal of Chemistry, 1996, vol. 74, # 12, p. 2518 - 2527]

10
[ 2150-41-6 ]
[ 39604-64-3 ]

Reference： [1]Bulletin of the Chemical Society of Japan,1958,vol. 31,p. 390,392
[2]Bulletin of the Chemical Society of Japan,1958,vol. 31,p. 390,392

11
[ 2150-41-6 ]
[ 103956-10-1 ]

Yield	Reaction Conditions	Operation in experiment
94.9%	With hydrazine hydrate In methanol for 6h; Reflux;	3.2. Synthesis of 2,4-dimethoxybenzohydrazide (2) Methyl 2-hydroxybenzoate (1) (7.60 g, 53 mmol) and 20 mL of hydrazine hydrate were mixed in methanol (50 mL). The mixture was refluxed for 6 hours. Methanol was then evaporated and the product formed was being rinsed with plenty of water to remove excess hydrazine hydrate. The product formed was left to dry at room temperature and yielded 7.21 g (94.9%). White solid, mp 149 C. 1H NMR (500 MHz, DMSO-d6): d 3.88 (s, 3H), 3.93 (s, 3H), 4.05 (s, 2H), 6.79 (dd, 1H, J = 2.0 Hz, 9.0 Hz), 6.84 (d, 1H,J = 2.0 Hz), 7.76 (d, 1H, J = 9.0 Hz); 9.40(s, 3H); 13C NMR (DMSOd6,125 MHz): d 165.17, 162.68, 159.84, 130.03, 117.10, 107.45,99.78, 56.78, 56.03; Anal. Calcd for C9H12N2O3, C, 55.09; H, 6.16;N, 14.28. Found C, 55.08; H, 6.17; N, 14.30; EI MS m/z (% rel abund.): 196.22 (M+, 64).
78%	With hydrazine In methanol Heating / reflux;	58.A A solution of 2, 4-dimethoxy-benzoic acid methyl ester (4.24g, 21.6 mmol) and hydrazine (3.4 mL, 108.1 mmol) in methanol (50 mL) was refluxed overnight. Solvent was removed under reduced pressure. The residue was re-dissolved in ethyl acetate. The solution of ethyl acetate was washed with saturated solution of sodium bicarbonate and brine, dried over sodium carbonate and concentrated to afford 2,4- dimethoxy-benzoic acid hydrazide (3. 31G, 78%) as a white solid :'H NMR (CDC13) 6 8. 77 (bs, 1 H), 8.15 (d, J=8. 8HZ, LH), 6. 58 (dd, J = 8. 8,2. 2 Hz, 1H), 6.46 (d, J = 2. 2 Hz, 1H), 4.10 (bs, 2H), 3.91 (s, 3H), 3.83 (s, 3H)
	With hydrazine In ethanol for 12h; Heating;

With hydrazine hydrate In ethanol for 12h; Reflux;

Reference： [1]Taha, Muhammad; Ismail, Nor Hadiani; Imran, Syahrul; Rokei, Muhammad Qamarruddin Bin; Saad, Syed Muhammad; Khan, Khalid Mohammed [Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 15, p. 4155 - 4162]
[2]Current Patent Assignee: ATHEROGENICS, INC.; GENERAL ELECTRIC CO - WO2004/56727, 2004, A2 Location in patent: Page 116-117
[3]Skoumbourdis, Amanda P.; Huang, Ruili; Southall, Noel; Leister, William; Guo, Vicky; Cho, Ming-Hsuang; Inglese, James; Nirenberg, Marshall; Austin, Christopher P.; Xia, Menghang; Thomas, Craig J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1297 - 1303]
[4]Al-Mansury, Sadiq; Balakit, Asim A.; Alkazazz, Fatin Fadhel; Ghaleb, Rana A. [Pharmaceutical Chemistry Journal, 2021, vol. 55, # 6, p. 556 - 565]

12
[ 67-56-1 ]
[ 91-52-1 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
95%	With sulfuric acid at 70℃; for 2h;
	With sulfuric acid for 14h; Heating / reflux;
	With sulfuric acid at 20℃; for 12h;

With sulfuric acid for 14h; Reflux;

2.1 2.1 1 ml of conc. sulfuric acid is added to a solution of 100 g of 2,4-dimethoxybenzoic acid in 500 ml of methanol, and the mixture is refluxed for 14 hours. The mixture is cooled, the solvent is removed, the residue is dissolved in 1 litre of MTB, the solution is washed three times with 200 ml of water each time and dried, and the solvent is removed, giving 105.5 g of methyl 2,4-dimethoxybenzoate.

Reference： [1]Hayrapetyan, Davit; Rit, Raja K.; Kratz, Markus; Tschulik, Kristina; Gooßen, Lukas J. [Chemistry - A European Journal, 2018, vol. 24, # 44, p. 11288 - 11291]
[2]Current Patent Assignee: MERCK KGAA - WO2006/87077, 2006, A2 Location in patent: Page/Page column 84
[3]Skoumbourdis, Amanda P.; Huang, Ruili; Southall, Noel; Leister, William; Guo, Vicky; Cho, Ming-Hsuang; Inglese, James; Nirenberg, Marshall; Austin, Christopher P.; Xia, Menghang; Thomas, Craig J. [Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 4, p. 1297 - 1303]
[4]Current Patent Assignee: MERCK KGAA - US2010/22540, 2010, A1 Location in patent: Page/Page column 30

13
[ 2150-41-6 ]
[ 906669-89-4 ]
[ 906669-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: methyl 2, 4-dimethoxybenzoate With chlorosulfonic acid at -5 - 20℃; for 14h; Stage #2: With water; potassium carbonate at 0℃;
	Stage #1: methyl 2, 4-dimethoxybenzoate With sulfuryl dichloride at 0 - 20℃; for 25.5h; Stage #2: With water; potassium carbonate	2.2 2.2 93.9 g of methyl 2,4-dimethoxybenzoate are added slowly, at a max. of 5°, to 128 ml of chlorosulfonic acid cooled to -5°. The mixture is stirred at 0° for 1.5 hours and at room temperature for 14 hours. The batch is poured onto ice, and the white precipitate is separated off and rinsed with a little water (=sulfonic acid chloride). The filtrate is adjusted to about pH 2 using potassium carbonate, and the precipitated material is subsequently separated off (=sulfonic acid K salt). The two crystallisates are dried, giving 24.8 g of and 134.3 g of

Reference： [1]Current Patent Assignee: MERCK KGAA - WO2006/87077, 2006, A2 Location in patent: Page/Page column 84-85
[2]Current Patent Assignee: MERCK KGAA - US2010/22540, 2010, A1 Location in patent: Page/Page column 30

14
[ 2150-41-6 ]
[ 407-25-0 ]
[ 174261-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	In acetic acid; ethyl acetate	R.29.1 REFERENCE EXAMPLE 29 (1) A 1.00 g portion of methyl 2,4-dimethoxybenzoate was suspended in 0.58 ml of acetic acid, and 1.44 ml of dry trifluoroacetic acid anhydride was added under ice-cooling, followed by stirring at room temperature for 12 hours. Under ice-cooling, a saturated sodium bicarbonate aqueous solution and ethyl acetate were added, and then insoluble matter was removed by celite filtration. The thus obtained filtrate was extracted with ethyl acetate, washed with water and saturated brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under a reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=100:1-80:1) to give 0.99 g of methyl 5-acetyl-2,4-dimethoxybenzoate. Mass spectrometry data (m/z) EI-MS: 238 (M+) Nuclear magnetic resonance spectrum (CDCl3, TMS internal standard) δ: 2.57 (3H, s), 3.86 (3H, s), 3.98 (3H, s), 3.98 (3H, s), 6.47 (1H, s), 8.41 (1H, s)

Reference： [1]Current Patent Assignee: ASTELLAS PHARMA INC. - US5686482, 1997, A

15
[ 2150-41-6 ]
[ 61070-98-2 ]
2-(2,4-dimethoxyphenyl)-1,3,5,6-tetraazaindene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; trichlorophosphate;	EXAMPLE 4 A mixture of 11 g of IIb, 19.6 g of methyl 2,4-dimethoxybenzoate and 300 ml of POCl3 is heated at 120 for 2 hours, and evaporated to dryness, and the residue is treated with 2N hydrochloric acid. This gives 2-(2,4-dimethoxyphenyl)-1,3,5,6-tetraazaindene, m.p. 268.

Reference： [1]Patent: US4477454,1984,A

16
[ 2150-41-6 ]
[ 174261-01-9 ]

Yield	Reaction Conditions	Operation in experiment
74%	With tetrabutyl-ammonium chloride; 3,3-dimethyldioxirane In acetone at 0℃; regioselective reaction;

Reference： [1]Location in patent: experimental part Lee, Yean-Jang; Wu, Huan-Ting; Lin, Chia-Ning [Letters in Organic Chemistry, 2009, vol. 6, # 7, p. 585 - 587]

17
[ 2150-41-6 ]
[ 39503-51-0 ]

Reference： [1]Letters in Organic Chemistry,2009,vol. 6,p. 585 - 587

18
[ 2150-41-6 ]
[ 3153-79-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With 3,3-dimethyldioxirane; tetra-(n-butyl)ammonium iodide In acetone at 25℃; regioselective reaction;

Reference： [1]Location in patent: experimental part Lee, Yean-Jang; Wu, Huan-Ting; Lin, Chia-Ning [Letters in Organic Chemistry, 2009, vol. 6, # 7, p. 585 - 587]

19
[ 865-33-8 ]
[ 106614-28-2 ]
[ 128272-26-4 ]
[ 2150-41-6 ]
[ 204707-42-6 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 3041 - 3044

20
[ 124-41-4 ]
[ 106614-28-2 ]
[ 128272-26-4 ]
[ 2150-41-6 ]
[ 204707-42-6 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 3041 - 3044

21
[ 2150-41-6 ]
[ 5446-02-6 ]

Yield	Reaction Conditions	Operation in experiment
93%	With aluminum (III) chloride In dichloromethane at -5 - 25℃;

Reference： [1]Location in patent: experimental part Du, Zhen-Ting; Lu, Jing; Yu, Hong-Rui; Xu, Yan; Li, An-Pai [Journal of Chemical Research, 2010, # 4, p. 222 - 227]

22
[ 67-56-1 ]
[ 91-52-1 ]
[ 7314-44-5 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
1: 60% 2: 30%	Stage #1: 2,4 dimethoxybenzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.5h; Stage #2: methanol With sodium tetrahydroborate In tetrahydrofuran at 0℃; for 0.5h;

Reference： [1]Location in patent: scheme or table Morales-Serna, Jose Antonio; Garcia-Rios, Erendira; Bernal, Jorge; Paleo, Ehecatl; Gavino, Ruben; Cardenas, Jorge [Synthesis, 2011, # 9, p. 1375 - 1382]

23
[ 141-32-2 ]
[ 2150-41-6 ]
[ 1392227-33-6 ]

Yield	Reaction Conditions	Operation in experiment
56%	With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 20 - 100℃; for 16h; chemoselective reaction;

Reference： [1]Graczyk, Karolina; Ma, Wenbo; Ackermann, Lutz [Organic Letters, 2012, vol. 14, # 16, p. 4110 - 4113]

24
[ 2150-41-6 ]
[ 140-88-5 ]
[ 1392227-32-5 ]

Yield	Reaction Conditions	Operation in experiment
54%	With silver hexafluoroantimonate; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; copper(II) acetate monohydrate In 1,2-dichloro-ethane at 20 - 100℃; for 16h; chemoselective reaction;

Reference： [1]Graczyk, Karolina; Ma, Wenbo; Ackermann, Lutz [Organic Letters, 2012, vol. 14, # 16, p. 4110 - 4113]

25
[ 106-88-7 ]
[ 2150-41-6 ]
[ 2213-43-6 ]
[ 1169880-27-6 ]

Yield	Reaction Conditions	Operation in experiment
11.43 g	In <i>tert</i>-butyl alcohol at 60℃; for 33h;	[Preparation of Hydroxyl-Containing Amine Imide E] [Preparation of Hydroxyl-Containing Amine Imide E] 19.62 g (0.10 mol) of methyl 2,4-dimethoxybenzoate, 10.96 g (0.10 mol) of 1-aminopiperidine, and 7.21 g (0.10 mol) of 1,2-epoxybutane were dissolved in 100 mL of t-butanol. The solution was reacted under stirring at 60° C. for 33 hours. After the reaction was completed, the solution was condensed to remove the solvent to give a viscous condensate. The viscous condensate was purified on a column packed with NH-silica gel (Fuji Silysia Chemical Ltd.) eluting with methanol/ethyl acetate (1:10). The purified product was washed with ethyl acetate/hexane (1:1) and dried in vacuo to give 11.43 g of white crystals with 99.0% purity (yield: 33.6 mol %). A part of the white crystals was sampled and 1H-NMR characterization was carried out on JEOL EXcalibur270 spectrometer (25° C., CDCl3, 270 MHz) to identify the crystal structure:7.39 (d, 1H, C6H3), 6.97-6.82 (m, 2H, C6H3), 4.89-4.74 (m, 2H, C5H10), 4.64-4.51 (m, 2H, C5H10), 4.34-4.20 (m, 1H, CHOH), 3.87-3.42 (m, 2H, NCH2), 3.83 (s, 6H2OCH3), 3.21-2.93 (m, 2H, C5H10), 2.33-2.09 (m, 2H, C5Ho), 1.82-1.59 (m, 2H, C5H10), 1.58-1.40 (m, 2H, CH2CH3), 1.03 (t, 3H, CH2CH3) (0188) A part of the white crystals was sampled and mass spectrometric analysis was carried out using ESI-MS (ZND, Micromass Inc.). The measured value was 337.2. These results confirm that the obtained white crystals were hydroxyl-containing amine imide E, i.e., 1-(2,4-dimethoxybenzoyl)amino-1-(2-hydroxybutyl)piperidinium inner salt.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US8466238, 2013, B2 Location in patent: Page/Page column 23; 24

26
[ 106-88-7 ]
[ 2150-41-6 ]
[ 57-14-7 ]
[ 1169880-25-4 ]

Yield	Reaction Conditions	Operation in experiment
5.80 g	In isopropyl alcohol at 20℃; for 144h;	[Preparation of Hydroxyl-Containing Amine Imide C] [Preparation of Hydroxyl-Containing Amine Imide C] 19.62 g (0.10 mol) of methyl 2,4-dimethoxybenzoate, 6.01 g (0.10 mol) of N,N-dimethylhydrazine, and 7.21 g (0.10 mol) of 1,2-epoxybutane were dissolved in 100 mL of isopropyl alcohol. The solution was reacted under stirring at room temperature for 6 days. After the reaction was completed, the solution was condensed in vacuo to remove the solvent and by-product methanol to give a viscous condensate. The viscous condensate was dissolved in 2 volumes of ethyl acetate. The solution was purified on a column packed with NH-silica gel (Fuji Silysia Chemical Ltd.) eluting with methanol/ethyl acetate (1:10). The purified product was dried in vacuo to give 5.80 g of transparent oily material with 98.0% purity (yield: 19.2 mol %). A part of the white crystals was sampled and 1H-NMR characterization was carried out on JEOL EXcalibur270 spectrometer (25° C., CDCl3, 270 MHz) to identify the crystal structure: 7.69 (d, 1H, C6H3), 6.95-6.87 (m, 2H, C6H3), 4.24-4.05 (m, 1H, CHOH), 3.83 (s, 6H2OCH3), 3.60 (d, 6H, NCH3), 3.52-3.07 (m, 2H, NCH2), 1.60-1.48 (m, 2H, CH2CH3), 1.02 (t, 3H, CH2CH3) (0178) A part of the white crystals was sampled and mass spectrometric analysis was carried out using ESI-MS (ZND, Micromass Inc.). The measured value was 297.2. These results confirm that the obtained white crystals were hydroxyl-containing amine imide C, i.e., 1,1-dimethyl-1-(2-hydroxybutyl)amine o,p-dimethoxybenzimide.

Reference： [1]Current Patent Assignee: MITSUI CHEMICALS,INC. - US8466238, 2013, B2 Location in patent: Page/Page column 22; 23

27
[ 17715-69-4 ]
[ 2150-41-6 ]
[ 76832-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 1-Bromo-2,4-dimethoxybenzene With n-butyllithium In diethyl ether; hexane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: methyl 2, 4-dimethoxybenzoate In diethyl ether; hexane for 0.05h;	3 Preparation of Hexamethoxy Red in Gram Scale Add (4.23 g, 19.47 mmol) 1-bromo-2,4-dimethoxybenzene (CAS 17715-69-4) to an appropriately sized round bottom flask. Attach a rubber septum to seal the flask. Insert a needle into the septum as a vent and flush the round bottom flask with nitrogen for about 10 minutes. Add (80 mL) anhydrous ether (CAS 60-29-7), followed by the drop wise addition of n-butyllithium (CAS 109-72-8) in hexane (CAS 110-54-3) (1.6M, 12.2 mL). Stir the cloudy mixture for 10 minutes and keep the round bottom flask on ice. Dissolve (2.20 g, 9.74 mmol) of methyl 2,4-dimethoxybenzoate (CAS 2150-41-6) in about 20 ml of anhydrous ether (CAS 60-29-7) (more than about 20 ml can be used if needed), and then add this drop wise to the reaction mixture. After the addition is complete, stir the reaction mixture for about 3 minutes longer. Pour the reaction mixture into a separatory funnel containing 5% NH4Cl (aq) (CAS 12125-02-9) (50 mL) and shake until a color change is observed (pale orange). The layers are allowed to separated, and dry the top ether layer with about 5 g anhydrous Na2SO4 (CAS 7757-82-6), filter, and rotovapped to dryness at 35-40° C. under 400 mbar. Place the crude oil of hexamethoxy red (yellow-orange in color) into the freezer. Yield is about 3.1 g .
	Stage #1: 1-Bromo-2,4-dimethoxybenzene With n-butyllithium In diethyl ether; hexane for 0.166667h; Inert atmosphere; Cooling with ice; Stage #2: methyl 2, 4-dimethoxybenzoate In diethyl ether; hexane for 0.05h;	3 Example 3 Preparation of Hexamethoxy Red in Gram Scale Add (4.23 g, 19.47 mmol) 1-bromo-2,4-dimethoxybenzene to an appropriately sized round bottom flask. Attach a rubber septum to seal the flask. Insert a needle into the septum as a vent and flush the round bottom flask with nitrogen for about 10 minutes. Add anhydrous ether (80 mL), followed by the drop wise addition of n-butyllithium in hexane (1.6M, 12.2 mL). Stir the cloudy mixture for 10 minutes and keep the round bottom flask on ice. Dissolve (2.20 g, 9.74 mmol) of methyl 2,4-dimethoxybenzoate in about 20 ml of anhydrous ether (if needed, more than about 20 ml can be used), and then add this drop wise to the reaction mixture. After the addition is complete, stir the reaction mixture for about 3 minutes longer. Pour the reaction mixture into a reparatory funnel containing 5% NH4Cl (aq) (50 mL) and shake until a color change is observed (pale orange). Allow the layers to separate, and dry the top ether layer with about 5 g anhydrous Na2SO4, filter, and remove the volatiles in a rotary evaporator to dryness at 35-40° C. under 400 mbar. Place the crude oil of hexamethoxy red (yellow-orange in color) into the freezer. Yield is about 3.1 g.

Reference： [1]Current Patent Assignee: INDICATOR SYSTEMS INTERNATIONAL, INC. - US8425996, 2013, B2 Location in patent: Page/Page column 19; 20
[2]Current Patent Assignee: INDICATOR SYSTEMS INT; INDICATOR SYSTEMS INTERNATIONAL, INC. - US2015/37258, 2015, A1 Location in patent: Paragraph 0085

28
[ 75-91-2 ]
[ 613-45-6 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper quinolate; tetra-(n-butyl)ammonium iodide In water; dimethyl sulfoxide at 120℃; for 24h;

Reference： [1]Zhu, Yan; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Journal of Organic Chemistry, 2013, vol. 78, # 19, p. 9898 - 9905]

29
[ 75-91-2 ]
[ 7314-44-5 ]
[ 2150-41-6 ]
[ 91-52-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium phosphate; copper quinolate; tetra-(n-butyl)ammonium iodide In water; dimethyl sulfoxide at 120℃; for 24h;

Reference： [1]Zhu, Yan; Yan, Hong; Lu, Linhua; Liu, Defu; Rong, Guangwei; Mao, Jincheng [Journal of Organic Chemistry, 2013, vol. 78, # 19, p. 9898 - 9905]

30
[ 99-50-3 ]
[ 89-86-1 ]
[ 149-91-7 ]
[ 99-10-5 ]
[ 303-38-8 ]
[ 490-79-9 ]
[ 99-06-9 ]
[ 69-72-7 ]
[ 74-88-4 ]
[ 99-96-7 ]
[ 2150-41-6 ]
[ 606-45-1 ]
[ 5368-81-0 ]
[ 121-98-2 ]
[ 2150-38-1 ]
[ 1916-07-0 ]
[ 2150-42-7 ]
[ 2150-40-5 ]
[ 2150-37-0 ]

Reference： [1]Chemical Communications,2014,vol. 50,p. 1694 - 1697

31
[ 67-56-1 ]
[ 39828-35-8 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
5.12 g	In dichloromethane at 20℃;	To a 100mL flask with a CaCl2 tube was added 2,4-dimethoxybenzoicacid S1 (5g, 27.5 mmol) and 20 mL of dry DCM. Oxalyl chloride (4.6mL55mmol) and five drop of DMF were added. The suspension was stirred at r.t. for1h. The solvent was evaporated to give 2,4-dimethoxybenzoyl chloride as an oil. This oil wasdissolved in DCM (10 mL) and was added dropwise to methanol (30 mL). After the addition,the mixture was allowed to stir at r.t. overnight. The solvent was evaporatedand the slurry was dissolved in DCM. The organic solvent was washed with sat.NaHCO3,brine and dried over anhydrous Na2SO4. The solvent was removed by rotaryevaporation to give theproduct methyl 2,4-dimethoxybenzoate S2 asa colourlessoil(5.12 g , 95%).1H NMR (400 MHz, Chloroform-d)δ 7.82 (d, J = 9.4 Hz, 1H), 6.48-6.44 (m, 2H), 3.86 (s, 3H), 3.83 (s,3H), 3.82 (s, 3H). MS(EI): m/z 196 M+. Retention time of 2.82 min, >99% pure.

Reference： [1]Ren, Jing; Li, Jian; Wang, Yueqin; Chen, Wuyan; Shen, Aijun; Liu, Hongchun; Chen, Danqi; Cao, Danyan; Li, Yanlian; Zhang, Naixia; Xu, Yechun; Geng, Meiyu; He, Jianhua; Xiong, Bing; Shen, Jingkang [Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 11, p. 2525 - 2529]

32
[ 2150-41-6 ]
[ 1191-17-9 ]
[ 39503-63-4 ]

Yield	Reaction Conditions	Operation in experiment
98%	With titanium tetrachloride In dichloromethane at 0℃; for 0.5h;	To S2 (3.2g,16.3mmol) and dichloromethyl methyl ether (9ml,102mmol)in DCM at 0 was added with stirring a solution of titanium(IV) chloride(20 ml,182mmol) in DCM (10 ml) during 0.5 h. The cooling bath was removed, themixture was stirred overnight, poured into ice-water, and extracted with DCM. Theextract was washed in turn with sat. NaHCO3,brine and dried over anhydrousNa2SO4. The solvent was removed by rotary evaporation to give the product methyl5-formyl-2,4-dimethoxybenzoate S3 as a brown solid (3.58 g , 98%).1H NMR(400 MHz, Chloroform-d) δ 10.28 (s, 1H), 8.41 (s, 1H), 6.46 (s, 1H), 4.01 (s, 3H),4.00 (s, 3H), 3.86 (s, 3H).MS (ESI) :m/z 225.1 (M+H)+.Retention timeof 2.64 min, >96% pure.

33
[ 2150-41-6 ]
[ 13007-92-6 ]
methyl 2,4-dimethoxylbenzoate-1-methylbenzene tricarbonyl chromium [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	In tetrahydrofuran at 150℃; for 48h; Inert atmosphere;

Reference： [1]Ricci, Paolo; Krämer, Katrina; Larrosa, Igor [Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18082 - 18086]

34
[ 4885-02-3 ]
[ 2150-41-6 ]
[ 873986-38-0 ]

Yield	Reaction Conditions	Operation in experiment
57%	Stage #1: Dichloromethyl methyl ether; methyl 2, 4-dimethoxybenzoate With zinc dibromide In dichloromethane at 20℃; for 14h; Stage #2: With ammonium hydroxide; iodine In dichloromethane at 20℃; for 6h;

Reference： [1]Tamura, Toshiyuki; Moriyama, Katsuhiko; Togo, Hideo [European Journal of Organic Chemistry, 2015, vol. 2015, # 9, p. 2023 - 2029]

35
[ 75-91-2 ]
[ 7314-44-5 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetraethylammonium bromide; oxygen; potassium carbonate In water; dimethyl sulfoxide at 100℃; for 16h;

Reference： [1]Molla, Rostam Ali; Iqubal, Md. Asif; Ghosh, Kajari; Kamaluddin; Islam, Sk. Manirul [Dalton Transactions, 2015, vol. 44, # 14, p. 6546 - 6559]

36
[ 95-21-6 ]
[ 2150-41-6 ]
[ 109-63-7 ]
1,1-difluoro-3-(2,4-dimethoxyphenyl)-1H-benzo[4,5]oxazolo[3,2-c][1,3,2]oxazaborinin-10-ium-1-uide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	Stage #1: 2-methyl-1,3-benzoxazole With sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 0.5h; Stage #2: methyl 2, 4-dimethoxybenzoate In tetrahydrofuran; mineral oil for 8h; Inert atmosphere; Reflux; Stage #3: boron trifluoride diethyl etherate With triethylamine In dichloromethane at 20℃; for 12h; Inert atmosphere;

Reference： [1]Zhang, Zhenqi; Wu, Zhu; Sun, Jingbo; Xue, Pengchong; Lu, Ran [RSC Advances, 2016, vol. 6, # 49, p. 43755 - 43766]

37
[ 67-56-1 ]
[ 613-45-6 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With aluminium(III) chloride hexahydrate; urea hydrogen peroxide adduct at 60℃; Green chemistry;	General Procedure. General procedure: A mixture of aldehyde (1.0 mmol), aluminum chloride hexahydrate (10 mol %), and urea hydrogen peroxide (5.0 mmol) was stirred in methyl alcohol (4.0 mL) at 60°C for 8-12 h. After cooling the mixture to room temperature the product was extracted into ethyl acetate (3 × 20 mL), washed with water and dried over sodium sulfate. The combined ether extracts were concentrated under reduced pressure and the crude product was purified by flash column chromatography (ethyl acetate/nhexane= 1:4, v/v) to give the desired methyl ester.

Reference： [1]Lee, Sin-Ae; Kim, Yoon Mi; Lee, Jong Chan [Bulletin of the Korean Chemical Society, 2016, vol. 37, # 8, p. 1368 - 1370]

38
[ 2150-41-6 ]
[ 501-65-5 ]
5,7-dimethoxy-2,3-diphenyl-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With silver hexafluoroantimonate; Cp*Co(CO)I₂; potassium acetate In 1,2-dichloro-ethane at 130℃; for 24h; Sealed tube; Inert atmosphere;

Reference： [1]Yu, Wenlong; Zhang, Wei; Liu, Zhanxiang; Zhang, Yuhong [Chemical Communications, 2016, vol. 52, # 41, p. 6837 - 6840]

39
[ 89-86-1 ]
[ 616-38-6 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
99%	With diiron nonacarbonyl at 180℃; for 1h; Sealed tube;	General procedure for the reaction of dimethyl carbonate with carboxylic acids. General procedure: 1-3 mmol of catalyst Mn 2 (CO) 10 , 100 mmol of the carboxylic acid, and 300-400 mmol of dimethyl carbonate were placed into a 17 mL stainless steel microreactor. The reactor was sealed, and the reaction mixture was heated at 180° for 1 h. After the reaction was complete, the reactor was cooled to room temperature and opened. The reaction mixture was filtered through a layer of Al 2 O 3 . Unreacted dimethyl carbonate was distilled off, the residue was distilled at atmospheric or reduced pressure, or crystallized.

Reference： [1]Khusnutdinov; Shchadneva; Mayakova, Yu. Yu. [Russian Journal of General Chemistry, 2018, vol. 88, # 1, p. 15 - 19][Zh. Obshch. Khim., 2018, vol. 88, # 1, p. 18 - 22,5]

40
[ 2150-41-6 ]
tert-butyl (5-(benzylcarbamoyl)-2,4-dimethoxybenzyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

41
[ 2150-41-6 ]
5-(aminomethyl)-2,4-dimethoxy-N-(2-methoxybenzyl)benzamide hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

42
[ 2150-41-6 ]
2,4-dimethoxy-5-((2-methoxybenzamido)methyl)-N-(2-methoxybenzyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 8.2: 4 h / 20 °C / Inert atmosphere

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

43
[ 2150-41-6 ]
5-(benzamidomethyl)-2,4-dimethoxy-N-(2-methoxybenzyl)benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 8 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 8.2: 4 h / 20 °C / Inert atmosphere

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

44
[ 2150-41-6 ]
methyl 2,4-dimethoxy-5-((methoxyimino)methyl)benzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2: pyridine / 1 h

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

45
[ 2150-41-6 ]
methyl 5-(aminomethyl)-2,4-dimethoxybenzoate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2: pyridine / 1 h 3: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

46
[ 2150-41-6 ]
methyl 5-(((tert-butoxycarbonyl)amino)methyl)-2,4-dimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2: pyridine / 1 h 3: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

47
[ 2150-41-6 ]
5-(((tert-butoxycarbonyl)amino)methyl)-2,4-dimethoxybenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2: pyridine / 1 h 3: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

48
[ 2150-41-6 ]
methyl 5-((5-(((tert-butoxycarbonyl)amino)methyl)-2,4-dimethoxybenzamido)methyl)-2,4-dimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere
	Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere

49
[ 2150-41-6 ]
methyl 5-((5-(aminomethyl)-2,4-dimethoxybenzamido)methyl)-2,4-dimethoxybenzoate hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere
	Multi-step reaction with 7 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere

50
[ 2150-41-6 ]
methyl 5-((5-((5-(((tert-butoxycarbonyl)amino)methyl)-2,4-dimethoxybenzamido)methyl)-2,4-dimethoxybenzamido)methyl)-2,4-dimethoxybenzoate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 4.2: 4 h / 20 °C / Inert atmosphere 5.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere
	Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere
	Multi-step reaction with 8 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere 7.1: hydrogenchloride / water; 1,4-dioxane / 2 h / 20 °C / Inert atmosphere 8.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 8.2: 4 h / 20 °C / Inert atmosphere

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]
[2]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]
[3]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

51
[ 2150-41-6 ]
tert-butyl (2,4-dimethoxy-5-((2-methoxybenzyl)carbamoyl)benzyl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: titanium tetrachloride / dichloromethane / 18 h / 0 - 20 °C 2.1: pyridine / 1 h 3.1: hydrogenchloride; hydrogen; palladium on activated charcoal / water; methanol / 16 h 4.1: N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h / 20 °C 5.1: lithium hydroxide / water; tetrahydrofuran / 6 h / 20 °C 6.1: N-ethyl-N,N-diisopropylamine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate / N,N-dimethyl-formamide / 0.08 h / 20 °C / Inert atmosphere 6.2: 4 h / 20 °C / Inert atmosphere

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

52
[ 4885-02-3 ]
[ 2150-41-6 ]
[ 39503-63-4 ]

Yield	Reaction Conditions	Operation in experiment
91%	In dichloromethane at 0 - 20℃; for 18h;
69%	With titanium tetrachloride In dichloromethane at 0 - 20℃; for 18h; regioselective reaction;

Reference： [1]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2019, vol. 21, # 19, p. 7763 - 7767]
[2]Meisel, Joseph W.; Hu, Chunhua T.; Hamilton, Andrew D. [Organic Letters, 2018, vol. 20, # 13, p. 3879 - 3882]

53
[ 67-56-1 ]
[ 201230-82-2 ]
[ 7438-18-8 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
34%	With tris(2,4-di-tert-butylphenyl)phosphite at 25℃; for 20h; Autoclave; Inert atmosphere;

Reference： [1]Xu, Jian-Xing; Franke, Robert; Wu, Xiao-Feng [Organic and Biomolecular Chemistry, 2018, vol. 16, # 34, p. 6180 - 6182]

54
[ 3186-53-6 ]
[ 133730-34-4 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
53%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(I) thiophene-2-carboxylate; trifuran-2-yl-phosphane In 1,4-dioxane at 60℃; for 16h; Sealed tube; Inert atmosphere;

Reference： [1]Cao, Ya-Fang; Li, Ling-Jun; Liu, Min; Xu, Hui; Dai, Hui-Xiong [Journal of Organic Chemistry, 2020, vol. 85, # 6, p. 4475 - 4481]

55
[ 2150-41-6 ]
[ 131341-58-7 ]
C₁₇H₁₆O₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2,5'-dihydroxy acetophenone With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 3h; Inert atmosphere; Heating; Stage #2: methyl 2, 4-dimethoxybenzoate In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	5.2 General procedure for the synthesis of 5a-d General procedure: A solution of LiHMDS in THF (1M, 4 equiv) was added to a well-stirred solution of 2,5-dihydroxyacetophenone (2, 1 equiv) in anhydrous THF (20mL) under argon at -78°C over 15min. The reaction mixture was stirred at -78°C for 1h and at -10°C for 2h and was cooled again to -78°C, and a solution of 3a-d (1 equiv) in THF (5mL) was added in one portion. The mixture was stirred at -78°C for 1h and at room temperature overnight. The reaction mixture was poured into a mixture of ice and neutralized with concentrated HCl (6.5mL) and extracted with dichloromethane. The combined organic layer was washed with brine and dried over sodium sulfate, filtered, and evaporated to give crude 4a-d. Crude 4a-d were dissolved in glacial acetic acid (20mL) and concentrated sulfuric acid (0.2mL). The reaction was stirred at room temperature for 4h. H2O (20mL) was added to the reaction mixture, and the resulting solid was filtered, washed with water, and dried to afford 5a-d.

Reference： [1]Wang, Xiao; Zhao, Wenting; Wang, Bin; Ding, Wei; Guo, Hao; Zhao, Hongyi; Meng, Jianzhou; Liu, Sihan; Lu, Yu; Liu, Yishuang; Zhang, Dongfeng [Bioorganic Chemistry, 2021, vol. 114]

56
[ 67-56-1 ]
[ 558-13-4 ]
[ 151-10-0 ]
[ 2150-41-6 ]

Yield	Reaction Conditions	Operation in experiment
85%	With [1,1'-bis(diphenylphosphino)ferrocene]nickel(II) chloride; Bathocuproine at 120℃; for 24h; Inert atmosphere; Sealed tube; regioselective reaction;

Reference： [1]Ji, Shun-Jun; Ju, Guodong; Tu, Guangliang; Zhao, Yingsheng [Organic Letters, 2022, vol. 24, # 11, p. 2155 - 2159]

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Response
Code	Phrase
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P321
P322
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P342	If experiencing respiratory symptoms:
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P361	Remove/Take off immediately all contaminated clothing.
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P378
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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.
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H240	Heating may cause an explosion
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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
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Code	Phrase
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H303	May be harmful if swallowed
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H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
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H315	Causes skin irritation
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H370	Causes damage to organs
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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. 2150-41-6 ] {[proInfo.proName]}

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[ 2150-41-6 ] Synthesis Path-Upstream 1~8

[ 2150-41-6 ] Synthesis Path-Downstream 1~56

Related Functional Groups of [ 2150-41-6 ]

Aryls

Ethers

Esters

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Health hazards

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[ 2150-41-6 ]