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 699-06-9 * 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 pyridine; hydroxylamine hydrochloride In ethanol for 1 h; Reflux
Step 1: Preparation of 4-hydroxy-benzaldehyde oxime; 4-Hydroxy-benzaldehyde (5 g, 40.94 mmol) was dissolved in EtOH (100 ml). Thereto, hydroxyl amine.HCl (4.3 g, 61.41 mmol) and pyridine (9.9 ml, 122.82 mmol) are added. The mixture is refluxed for 1 hour. The resultant is concentrated under a reduced pressure, extracted with Et2O. The entire extracts are washed with brine and dried over MgSO4. The resulting organic solution is concentrated under a reduced pressure and purified by column chromatography (EtOAc:hexane=1:2) to obtain the compound, 4-hydroxy-benzaldehyde oxime (5.9 g, 100percent).1H NMR (CDCl3, 200 MHz) δ 9.23 (s, 1H), 8.15 (brs, 1H), 7.82 (s, 1H), 7.22 (d, J=8.8 Hz, 2H), 6.63 (d, J=8.8 Hz, 2H).
98%
With pyridine; hydroxylamine hydrochloride In ethanol at 80℃; for 1 h;
To a 100-ml flask, 500 mg (4.09 mmol) of 4-hydroxybenzaldehyde was added and dissolved in 10 ml of ethanol,followed by stirring. 1 ml (12.3 mmol, 3.0 eq) of pyridine and 427 mg (6.14 mmol, 1.5 eq) of hydroxylamine hydrochloridewere added thereto, and refluxed at 80°C under stirring for 1 hour. After completion of the reaction, the reaction productwas concentrated under reduced pressure and diluted with ethyl acetate (30 ml) and washed with water (70 ml). Afterseparation of layers, an organic layer was washed with a saturated NH4Cl aqueous solution, and then washed withwater. An organic layer was separated and washed with a NaCl aqueous solution, and then dehydrated and dried overMgSO4, and concentrated under reduced pressure to obtain 550 mg (98percent) of a title compound.1H NMR (dimethyl sulfoxide-d4, 600MHz) δ 10.83(s, 1H), 9.75(br, 1H), 7.99(s, 1H), 7.38(d, 2H), 6.75(d, 2H)Mass[M+H] : 138.05
96%
With zinc(II) oxide; hydroxylamine hydrochloride; silica gel In neat (no solvent) at 20℃; for 0.1 h; Green chemistry
General procedure: Hydroxylamine hydrochloride (0.138 g, 2 mmol), ZnO nanotubes (0.071 g, 0.8 mmol), silica gel (0.43 g) and aldehyde (ketone) (1 mmol) were ground together in a mortar with a pestle at room temperature for a period of time as indicated in Tables 1 and 2. The progress of the reaction was monitored by TLC. After complete disappearance of the starting materials, the reaction mixture was poured with diethyl ether (2×10 mL) and filtered to remove silica gel and ZnO nanotubes, The filtrate mixed with water and extracted. The solvent was removed in vaccuo to give the product which was recrystallized from suitable solvent and afforded the TLC and 1H-NMR pure products in 75-98 percent isolated yields.
93%
With hydroxylamine hydrochloride; sodium acetate In ethanol; water
N6-(4-Hydroxybenzyl)adenosine (1). Hydroxylamine hydrochloride (1.29 g, 18.6 mmol) and sodium acetate (1.67 g, 20.4 mmol) were added to a solution of 4-hydroxybenzaldehyde (1.25 g, 10.2 mmol) in ethanol (20 mL). The reaction mixture was stirred at zoom temperature for 6 h. Ethanol was removed under reduced pressure. The residue was added water, and then extracted with Et2O (3*). The combined organic layer was dried over MgSO4. After the volatiles were removed by rotary evaporation under reduced pressure, the residue was recrystallized from CH2Cl2 to give the oxime of 4-hydroxybenzaldehyde (1.3 g, 93percent). C2H7NO2; light yellow solid, mp 92.0-93.6° C.
85%
With sodium hydroxide; hydroxylamine hydrochloride In methanol
The halogenated 4-hydroxybenzaldehydes Ib-Ih (FIG. 7) were either commercially available or prepared according to the procedure described in literature (Lawrence et al., 2003). The oκimes 2a-2h (FIG.7) were synthesized in excellent yields by condensation of hydroxylamine with the aldehydes Ia-Ih in basic alcoholic solvent. The final compounds 3a-3h (FIG. 7) were synthesized in good yields by condensation of oximes 2a-2h with cyclohexanecarboxylic acid chloride in dry dichloromethane in present of pyridine from 0 °C to room temperature overnight (Scheme 1) (See Supplemental Material below). Compound 4 and 5 were prepared as the similar method as the compound 3 (FIG. 8). The final compounds 3a-3h, 4 and 5 reported here were fully characterized by 1H NMR, 13C NMR and ESI-MS (See Supplemental Material below).
2.66 g
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 6 h;
First step, p-hydroxybenzaldehyde (2.55 g) hydroxyamine hydrochloride (2.60 g) and NaOAc (3.40 g) were dissolved in EtOH (80 ml). The reaction mixture was stirred at room temperature for 6 h.EtOH was removed under reduced pressure. H2O (40 ml) was added to the residue, and extracted with EtOAc (3*40 ml). The EtOAc of the combined organic layer was removed by rotary evaporation under reduced pressure to yield p-hydroxybenzaldehyde oxime (2.66 g) as a pale yellowish solid.
2.66 g
With hydroxylamine hydrochloride; sodium acetate In ethanol at 20℃; for 6 h;
weigh precisely P-hydroxybenzaldehyde (2.55 g), hydroxylamine hydrochloride (2.60 g) and anhydrous sodium acetate (3.40 g), dissolve in ethanol (80 mL), stir at room temperature for 6 hours, Recover the solvent with the reaction solution, add water, mix thoroughly, dissolve, extract 40 ml ethyl acetate, extract a total of 3 times, recover solvent with phase of ethyl acetate, light yellow solid of2.66 g of p-hydroxyoxime are obtained.
Reference：
[1] Patent: US2010/48570, 2010, A1, . Location in patent: Page/Page column 45
[2] Patent: EP3135669, 2017, A1, . Location in patent: Paragraph 0302; 0303
[3] Revue Roumaine de Chimie, 2015, vol. 60, # 9, p. 875 - 880
[4] Monatshefte fur Chemie, 2001, vol. 132, # 3, p. 403 - 406
[5] Journal of Natural Products, 2007, vol. 70, # 4, p. 571 - 574
[6] ChemMedChem, 2011, vol. 6, # 8, p. 1390 - 1400
[7] Journal of Organic Chemistry, 2013, vol. 78, # 17, p. 8386 - 8395
[8] Patent: US2015/374737, 2015, A1,
[9] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1354 - 1356
[10] Journal of the Indian Chemical Society, 2013, vol. 90, # 4, p. 529 - 532
[11] Monatshefte fur Chemie, 2006, vol. 137, # 3, p. 301 - 305
[12] Journal of Organic Chemistry, 2011, vol. 76, # 11, p. 4665 - 4668
[13] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 7, p. 1879 - 1885
[14] Organic and Biomolecular Chemistry, 2015, vol. 13, # 12, p. 3610 - 3624
[15] Patent: WO2007/145888, 2007, A2, . Location in patent: Page/Page column 26
[16] Russian Journal of Organic Chemistry, 2003, vol. 39, # 12, p. 1777 - 1780
[17] Journal of the American Chemical Society, 1944, vol. 66, p. 1875,1879
[18] Chemische Berichte, 1883, vol. 16, p. 1786
[19] Bioorganic Chemistry, 2003, vol. 31, # 2, p. 129 - 135
[20] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 10, p. 1795 - 1799
[21] Synthesis, 2005, # 5, p. 787 - 790
[22] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 3, p. 499 - 502
[23] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 13, p. 4773 - 4785
[24] Molecules, 2010, vol. 15, # 1, p. 94 - 99
[25] Advanced Synthesis and Catalysis, 2009, vol. 351, # 11-12, p. 1807 - 1812
[26] Journal of Medicinal Chemistry, 2011, vol. 54, # 3, p. 765 - 781
[27] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 24, p. 7365 - 7373
[28] Patent: EP2511283, 2012, A1, . Location in patent: Page/Page column 38
[29] Patent: US2013/45942, 2013, A1, . Location in patent: Paragraph 0085
[30] European Journal of Organic Chemistry, 2014, vol. 2014, # 9, p. 1961 - 1975
[31] Patent: WO2015/49693, 2015, A1, . Location in patent: Sheet 10
[32] European Journal of Organic Chemistry, 2014, vol. 2014, # 9, p. 1961 - 1975
[33] RSC Advances, 2015, vol. 5, # 110, p. 90408 - 90421
[34] Synthesis (Germany), 2015, vol. 47, # 23, p. 3758 - 3766
[35] Angewandte Chemie - International Edition, 2016, vol. 55, # 12, p. 3997 - 4001[36] Angew. Chem., 2016, vol. 128, # 12, p. 4065 - 4069,5
[37] Synthetic Communications, 2017, vol. 47, # 3, p. 232 - 237
[38] Bioorganic and Medicinal Chemistry, 2017, vol. 25, # 20, p. 5290 - 5302
[39] European Journal of Organic Chemistry, 2018, vol. 2018, # 4, p. 506 - 514
[40] New Journal of Chemistry, 2018, vol. 42, # 19, p. 15546 - 15551
[41] Patent: JP2015/172077, 2015, A, . Location in patent: Paragraph 0094
2
[ 696-60-6 ]
[ 699-06-9 ]
Yield
Reaction Conditions
Operation in experiment
88%
With Acetaldehyde oxime; oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione In water at 100℃; for 34 h; Green chemistry
General procedure: A mixture of primary amine (1 mmol), THICA (5 molpercent), acetaldoxime(10 molpercent), and H2O (5 mL) was placed in a three-neckedflask. O2 was stirred into the flask at a flow rate of 20 mL/min. The reaction mixture was stirred at 100 °C for several hours, and the reaction progress was monitored by TLC. When the final reaction mixture was cooled to r.t. and extracted with Et2O, the organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was pure enough. When necessary,the crude product was purified by chromatography using EtOAc–PE (1:8) as eluent.
Reference：
[1] Synlett, 2014, vol. 25, # 13, p. 1873 - 1878
[2] New Journal of Chemistry, 2015, vol. 39, # 8, p. 6677 - 6682
3
[ 106-44-5 ]
[ 699-06-9 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 27, p. 7397 - 7401
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 27, p. 7397 - 7401
With Acetaldehyde oxime; oxygen; 1N,3N,5N-trihydroxy-1,3,5-triazin-2,4,6[1H,3H,5H]-trione; In water; at 100℃; for 34h;Green chemistry;
General procedure: A mixture of primary amine (1 mmol), THICA (5 mol%), acetaldoxime(10 mol%), and H2O (5 mL) was placed in a three-neckedflask. O2 was stirred into the flask at a flow rate of 20 mL/min. The reaction mixture was stirred at 100 C for several hours, and the reaction progress was monitored by TLC. When the final reaction mixture was cooled to r.t. and extracted with Et2O, the organic layer was washed with brine, dried over MgSO4, and concentrated under reduced pressure. The residue was pure enough. When necessary,the crude product was purified by chromatography using EtOAc-PE (1:8) as eluent.
With tetraphosphorus decasulfide; In toluene; at 80 - 85℃;
Add 900g of toluene to the reaction flask; add 150g (1.094mol) 152G1-00; add 245g (1.102mol) of phosphorus pentasulfide under stirring, heat to 80-85 C, and keep stirring for about 2 ~ 4hr; after the reaction is completed, cool down to 50 60 , concentrate about 600g 700g toluene under reduced pressure, add 900g water to the residue, continue to concentrate and dry the residual toluene under reduced pressure, cool the remaining materials to 5 15 , and keep crystallization for about 2 4hr; filter , The filter cake was rinsed with water to collect the solids; dried at 75 to 85 C. to obtain about 153 g (theoretical amount: 167.6 g) of 152A1-00 dry product. Yield: 91.3%.
Chemistry
Pharmaceutical Intermediates
Inhibitors/Agonists
Material Science
HazMat Fee +
For Research Only
110K+ Compounds
Competitive Price
1-2 Day Shipping
