There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.
Type
HazMat fee for 500 gram (Estimated)
Excepted Quantity
USD 0.00
Limited Quantity
USD 15-60
Inaccessible (Haz class 6.1), Domestic
USD 80+
Inaccessible (Haz class 6.1), International
USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic
USD 100+
Accessible (Haz class 3, 4, 5 or 8), International
USD 200+
Structure of 87-64-9 * Storage: {[proInfo.prStorage]}
* 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.
With 1,2-dithiolane; aluminum (III) chloride; sulfuryl dichloride In melt for 4 h;
General procedure: o-Cresol (melted) or m-cresol (5.41 g, 50.0 mmol), AlCl3 (0.25 g) and the catalyst (100 mg)were added to a dried 50 ml round-bottomed flask. Sulfuryl chloride (4.66 ml, 57.7 mmol) wasthen added slowly over 2 h via a pressure-equalizing dropping funnel. The reaction mixture wasstirred for 2 h before being quenched with water (20 ml). The reaction mixture was worked up,and the crude products were weighed until constant mass and then analyzed by quantitative GC.
93.4 %Chromat.
at 20℃; for 4 h;
Freshly distilled sulfuryl chloride (4.66 mL, 57.7 mmol) was added slowly over 2 h to a mixture of o-cresol or m-cresol (5.41 g, 50 mmol), AlCl3 (0.25 g, 1.875mmol) and an additive (100 mg) in a round bottomed flask (50mL). The mixture was stirred at room temperature for a further 2 h, then worked up and analyzed by GC as shown for m-xylenol.
Reference：
[1] Synthetic Communications, 2002, vol. 32, # 2, p. 279 - 286
[2] Synlett, 2011, # 11, p. 1537 - 1542
[3] Journal of the Chemical Society, Chemical Communications, 1980, # 1, p. 8 - 9
[4] Journal of the Chemical Society, Chemical Communications, 1980, # 1, p. 8 - 9
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 161[6] Chem. Zentralbl., 1928, vol. 99, # II, p. 767
[7] Tetrahedron Letters, 1988, vol. 29, # 11, p. 1319 - 1322
[8] Tetrahedron, 1982, vol. 38, # 15, p. 2339 - 2346
[9] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 161[10] Chem. Zentralbl., 1928, vol. 99, # II, p. 767
[11] Journal of the Chemical Society, 1928, p. 3269
[12] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3117 - 3120
[13] Tetrahedron, 1982, vol. 38, # 15, p. 2339 - 2346
[14] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 385 - 392
[15] Synthetic Communications, 2002, vol. 32, # 5, p. 735 - 740
[16] Tetrahedron Letters, 2003, vol. 44, # 29, p. 5491 - 5494
[17] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
[18] Journal of Sulfur Chemistry, 2015, vol. 36, # 1, p. 74 - 85
[19] Journal of Sulfur Chemistry, 2018, vol. 39, # 6, p. 607 - 621
2
[ 95-48-7 ]
[ 1570-65-6 ]
[ 87-64-9 ]
Reference：
[1] Journal of the American Chemical Society, 1935, vol. 57, p. 2176
Reference：
[1] Journal of the American Chemical Society, 1935, vol. 57, p. 2176
13
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 95-71-6 ]
[ 608-25-3 ]
[ 108372-60-7 ]
[ 553-97-9 ]
[ 95-48-7 ]
[ 488-17-5 ]
[ 87-64-9 ]
Reference：
[1] Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 8 - 14
14
[ 95-48-7 ]
[ 1570-64-5 ]
[ 87-64-9 ]
Yield
Reaction Conditions
Operation in experiment
93.2 %Chromat.
With 1,2-dithiolane; aluminum (III) chloride; sulfuryl dichloride In melt for 4 h;
General procedure: o-Cresol (melted) or m-cresol (5.41 g, 50.0 mmol), AlCl3 (0.25 g) and the catalyst (100 mg)were added to a dried 50 ml round-bottomed flask. Sulfuryl chloride (4.66 ml, 57.7 mmol) wasthen added slowly over 2 h via a pressure-equalizing dropping funnel. The reaction mixture wasstirred for 2 h before being quenched with water (20 ml). The reaction mixture was worked up,and the crude products were weighed until constant mass and then analyzed by quantitative GC.
93.4 %Chromat.
at 20℃; for 4 h;
Freshly distilled sulfuryl chloride (4.66 mL, 57.7 mmol) was added slowly over 2 h to a mixture of o-cresol or m-cresol (5.41 g, 50 mmol), AlCl3 (0.25 g, 1.875mmol) and an additive (100 mg) in a round bottomed flask (50mL). The mixture was stirred at room temperature for a further 2 h, then worked up and analyzed by GC as shown for m-xylenol.
Reference：
[1] Synthetic Communications, 2002, vol. 32, # 2, p. 279 - 286
[2] Synlett, 2011, # 11, p. 1537 - 1542
[3] Journal of the Chemical Society, Chemical Communications, 1980, # 1, p. 8 - 9
[4] Journal of the Chemical Society, Chemical Communications, 1980, # 1, p. 8 - 9
[5] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 161[6] Chem. Zentralbl., 1928, vol. 99, # II, p. 767
[7] Tetrahedron Letters, 1988, vol. 29, # 11, p. 1319 - 1322
[8] Tetrahedron, 1982, vol. 38, # 15, p. 2339 - 2346
[9] Zhurnal Russkago Fiziko-Khimicheskago Obshchestva, 1928, vol. 60, p. 161[10] Chem. Zentralbl., 1928, vol. 99, # II, p. 767
[11] Journal of the Chemical Society, 1928, p. 3269
[12] Tetrahedron Letters, 1983, vol. 24, # 30, p. 3117 - 3120
[13] Tetrahedron, 1982, vol. 38, # 15, p. 2339 - 2346
[14] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1988, p. 385 - 392
[15] Synthetic Communications, 2002, vol. 32, # 5, p. 735 - 740
[16] Tetrahedron Letters, 2003, vol. 44, # 29, p. 5491 - 5494
[17] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5823 - 5828
[18] Journal of Sulfur Chemistry, 2015, vol. 36, # 1, p. 74 - 85
[19] Journal of Sulfur Chemistry, 2018, vol. 39, # 6, p. 607 - 621
15
[ 94-74-6 ]
[ 1570-65-6 ]
[ 1570-64-5 ]
[ 95-71-6 ]
[ 608-25-3 ]
[ 108372-60-7 ]
[ 553-97-9 ]
[ 95-48-7 ]
[ 488-17-5 ]
[ 87-64-9 ]
Reference：
[1] Journal of Photochemistry and Photobiology A: Chemistry, 2012, vol. 228, # 1, p. 8 - 14
16
[ 108-41-8 ]
[ 1570-64-5 ]
[ 6640-27-3 ]
[ 873-63-2 ]
[ 87-64-9 ]
Reference：
[1] Journal of Physical Chemistry, 1994, vol. 98, # 37, p. 9158 - 9164
17
[ 87-64-9 ]
[ 2467-25-6 ]
Reference：
[1] Il Farmaco; edizione scientifica, 1963, vol. 18, p. 619 - 642
18
[ 108-41-8 ]
[ 1570-64-5 ]
[ 6640-27-3 ]
[ 873-63-2 ]
[ 87-64-9 ]
Reference：
[1] Journal of Physical Chemistry, 1994, vol. 98, # 37, p. 9158 - 9164
To a solution of 2-chloro-6- methylphenol 34 (5 g, 35 mmol) in AcOH (70 mL) was added NBS (6.2 g, 35 mmol). The solution was stirred at RT for 12 h. AcOH was removed under reduced pressure. The residue was diluted with EtOAc, washed with saturated Na2C03 solution and dried over Na2S04. Removal of the solvents gave compound 35 (4 g, 52percent) which was used in the next step without further purification.
Reference：
[1] Patent: WO2017/4609, 2017, A1, . Location in patent: Paragraph 0219
[2] Heterocycles, 1993, vol. 36, # 7, p. 1483 - 1488
[3] Patent: US2008/146595, 2008, A1, . Location in patent: Page/Page column 24
[4] Patent: WO2017/4608, 2017, A1, . Location in patent: Paragraph 0142
[5] European Journal of Medicinal Chemistry, 2017, vol. 127, p. 944 - 957
With N-Bromosuccinimide; acetic acid; at 20℃; for 12h;
To a solution of 2-chloro-6- methylphenol 34 (5 g, 35 mmol) in AcOH (70 mL) was added NBS (6.2 g, 35 mmol). The solution was stirred at RT for 12 h. AcOH was removed under reduced pressure. The residue was diluted with EtOAc, washed with saturated Na2C03 solution and dried over Na2S04. Removal of the solvents gave compound 35 (4 g, 52%) which was used in the next step without further purification.
With N-Bromosuccinimide; In acetic acid; at 20℃;
step 1-NBS (100 mmol) was added to a mixture of 60a (100 mmol) in HOAc (200 mL) and the mixture was stirred at RT overnight. The HOAc was removed and the residue was diluted with EtOAc and washed with saturated Na2CO3. The combined organic phase was dried (Na2SO4), filtered and evaporated to afford 60b as white solid that was used without further purification. _
With N-Bromosuccinimide; acetic acid; at 20℃; for 12h;
Step 1: 2-ChIoro-4-bromo-6-methylphenol (22). To a solution of 2-chloro-6- methylphenol 21 (5 g, 35 mmol) in AcOH (70 mL) was added NBS (6.2 g, 35 mmol). The solution was stirred at RT for 12 h. AcOH was removed under reduced pressure. The residue was diluted with EtOAc, washed with saturated Na2C03 solution and dried over Na2S04. Removal of the solvents gave desired compound 22 (4 g, 52%) which was used in the next step without further purification.
4-chloro-6-(2-chloro-6-methylphenoxy)-2,5-dimethylpyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
85%Chromat.
With sodium hydroxide; In tetrahydrofuran; water; at 110℃; under 3000.3 Torr; for 0.333333h;Flow reactor; Green chemistry;
General procedure: Two solutions, one with the aryl halide (0.56 mmol, 1.0equivalent) in THF?H2O (2.5 mL, 3:2 v/v) and one with phenol (0.84mmol, 1.5 equivalent) and NaOH (0.84 mmol, 1.5 equivalent) in THF?H2O(2.5 mL, 3:2 v/v) were prepared and then introduced into Asia microfluidicreactor by Pump A & B.. The mixture was pumped through a preheated 1 mL glassmicrofluidic reactor at a predetermined flow rate to achieve the desiredresidence time. The crude product was collected in a flask and extracted withethyl acetate. The organic phase was combined, dried MgSO4 andconcentrated under reduced pressure. The isolated crude product was purifiedusing a prepacked silica cartridge on a Teledyne CombiFlash Rf 200instrument. Fractions corresponding to the product peak were combined andconcentrated using rotavap. For the synthesis of compound 3e and 3f correspondingsodium alkoxides were used as input for the second pump.
4,6-dichloro-2-(2-chloro-6-methylphenoxy)pyrimidine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
52%
To a mixture of 2-chloro-6-methyl-phenol (3.0 g, 21 mmol) in dry THF (50 mL) was added NaH (0.84 g, 21 mmol) at -50 C. under N2. The reaction contents were stirred at -50 C. over 30 min. 4,6-Dichloro-2-methanesulfonyl-pyrimidine (4.8 g, 21 mmol) was added. The reaction mixture was stirred at -50 C. over 30 hr. It was quenched with water (50 mL) and concentrated. The residue was treated with DCM (50 mL) and washed with brine (20 mL). The organic phase was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel PE/E EtOAc (50:1) to give the title compound (3.2 g, 11 mmol) as a white solid in 52% yield. 1H NMR (300MHz, CDCl3) delta 7.33 (dd, J=7.2 Hz, 2.4 Hz, 1H), 7.18 (m, 3H), 2.23 (s, 3H). LCMS (M+H)+289.
methyl 5-bromo-6-(2-chloro-6-methylphenoxy)nicotinate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
91%
With caesium carbonate; In dimethyl sulfoxide; at 80℃; for 1.5h;
A mixture of 2-chloro-6-methylphenol (1.195 g, 8.38 mmol), methyl 5-bromo-6- chloronicotinate (2g, 7.98 mmol), and cesium carbonate (2.60 g, 7.98 mmol) in anhydrous dimethyl sulfoxide (20 mL) was stirred at 80 C for 1.5 hours. After cooling to ambienttemperature, water (40 mL) was added to the mixture, and the precipitated product was collected by filtration and dried to provide the title compound (2.6 g, 7.29 mmol, 91 % yield) as off-white solid.
methyl 3-bromo-4-(2-chloro-6-methylphenoxy)benzoate[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
65.5%
With caesium carbonate; In dimethyl sulfoxide; at 100℃; for 1h;Inert atmosphere;
A mixture of cesium carbonate (839 mg, 2.57 mmol), 2-chloro-6-methylphenol (294 mg, 2.060 mmol), and <strong>[82702-31-6]methyl 3-bromo-4-fluorobenzoate</strong> (400 mg, 1.716 mmol) in dimethyl sulfoxide (5 mL) was stirred at 100 C for 1 hour under nitrogen. After cooling to ambienttemperature, water (50 mL) was added. The resulting mixture was extracted with ethyl acetate (50 mL) twice. The organic layers were combined and dried over anhydrous sodium sulfate. After filtration and solvent removal the crude material was purified by flash chromatographed (silica gel, 0-50 % ethyl acetate/petroleum ether) to provide the title compound (400 mg, 65.5 % yield).
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
HazMat Fee +
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
