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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 22364-68-7 * 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.
Reference：
[1] Patent: US6372921, 2002, B1, . Location in patent: Example 7
[2] Tetrahedron Letters, 2001, vol. 42, # 38, p. 6737 - 6739
[3] Recueil des Travaux Chimiques des Pays-Bas, 1960, vol. 79, p. 1211 - 1222
2
[ 18293-53-3 ]
[ 95-46-5 ]
[ 22364-68-7 ]
Reference：
[1] Journal of the American Chemical Society, 2005, vol. 127, # 45, p. 15824 - 15832
3
[ 552-45-4 ]
[ 22364-68-7 ]
Yield
Reaction Conditions
Operation in experiment
72 %Chromat.
With palladium diacetate; sodium carbonate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 140℃; for 10 h; Inert atmosphere
General procedure: 0.06 mmol PPh3, 0.02 mmol Pd(OAc)2, and 0.4 mL NMP were added into a dried 20 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 5 min to give a homogeneous solution, 0.3 mmol K4[Fe(CN)6], 1.5 mmol Na2CO3, 1 mmol benzyl chloride, and 0.4 mL NMP were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 140(+/-5) °C to perform the reaction for 10 h. Once the reaction time was reached, the mixture was cooled to room temperature, then acetophenone was added as an internal standard. GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was purified by column chromatography and identified by 1H NMR, 13C NMR or GC-MS data.
82 %Chromat.
With copper(l) iodide In toluene at 180℃; for 20 h; Inert atmosphere; Sealed tube
General procedure: 0.3 mmol CuI and 0.3 mL toluene were added into a dried 40 mL tube under a dry nitrogen atmosphere. After the mixture was stirred at room temperature for about 1 min, 0.5 mmol K4[Fe(CN)6], 1 mmol benzyl chloride, and 0.7 mL toluene were added under a dry nitrogen atmosphere. The reaction tube was sealed with a septum and placed in a constant-temperature oil bath set at 180(+/-5) °C to perform the reaction for 20 h. Once the reaction time was reached, the mixture was cooled to room temperature, then 1 mL solution of acetophenone (0.8 mmol/mL in dichloromethane) was added as an internal standard into the reaction tube. Subsequently, GC analysis of the mixture provided the yield of the product (note: in order to decrease the analysis error, the mixture after the reaction was not purified or concentrated). The cyanation product was identified by GC-MS data.
Reference：
[1] Journal of Organic Chemistry, 2017, vol. 82, # 14, p. 7621 - 7627
6
[ 84109-17-1 ]
[ 590-17-0 ]
[ 605-39-0 ]
[ 22364-68-7 ]
Reference：
[1] Synthesis, 1987, # 1, p. 40 - 42
7
[ 16419-60-6 ]
[ 6011-14-9 ]
[ 22364-68-7 ]
Reference：
[1] Angewandte Chemie - International Edition, 2014, vol. 53, # 39, p. 10510 - 10514[2] Angew. Chem., 2014, vol. 126, # 39, p. 10678 - 10682,5
8
[ 95-46-5 ]
[ 17729-59-8 ]
[ 22364-68-7 ]
Reference：
[1] Chemistry Letters, 1984, p. 1511 - 1512
9
[ 928664-98-6 ]
[ 95-46-5 ]
[ 22364-68-7 ]
Reference：
[1] Journal of the American Chemical Society, 2011, vol. 133, # 18, p. 6948 - 6951
10
[ 143-33-9 ]
[ 89-92-9 ]
[ 22364-68-7 ]
Reference：
[1] Collection of Czechoslovak Chemical Communications, 1987, vol. 52, # 10, p. 2545 - 2563
[2] Journal of the Chemical Society [Section] C: Organic, 1971, p. 190 - 196
Reference：
[1] European Journal of Organic Chemistry, 2017, vol. 2017, # 16, p. 2379 - 2384
18
[ 89-95-2 ]
[ 22364-68-7 ]
Reference：
[1] Recueil des Travaux Chimiques des Pays-Bas, 1960, vol. 79, p. 1211 - 1222
19
[ 151-50-8 ]
[ 89-92-9 ]
[ 22364-68-7 ]
Reference：
[1] Journal of the Chemical Society, 1907, vol. 91, p. 1699
[2] Chemische Berichte, 1885, vol. 18, p. 1281[3] Chemische Berichte, 1882, vol. 15, p. 1747
[4] Collection of Czechoslovak Chemical Communications, 1964, vol. 29, p. 776 - 794
[5] Justus Liebigs Annalen der Chemie, 1929, vol. 468, p. 222
20
[ 108-88-3 ]
[ 75-05-8 ]
[ 2947-60-6 ]
[ 2947-61-7 ]
[ 22364-68-7 ]
Reference：
[1] Chemical Communications, 2013, vol. 49, # 36, p. 3793 - 3795
21
[ 107-14-2 ]
[ 108-88-3 ]
[ 110-61-2 ]
[ 2947-60-6 ]
[ 2947-61-7 ]
[ 103-29-7 ]
[ 645-59-0 ]
[ 22364-68-7 ]
Reference：
[1] Journal of Organic Chemistry, 1984, vol. 49, p. 2728 - 2733
[2] Journal of the Chemical Society, Chemical Communications, 1981, # 16, p. 817 - 818
22
[ 108-88-3 ]
[ 75-05-8 ]
[ 2947-60-6 ]
[ 2947-61-7 ]
[ 22364-68-7 ]
Reference：
[1] Chemical Communications, 2013, vol. 49, # 36, p. 3793 - 3795
23
[ 107-14-2 ]
[ 108-88-3 ]
[ 110-61-2 ]
[ 2947-60-6 ]
[ 2947-61-7 ]
[ 103-29-7 ]
[ 645-59-0 ]
[ 22364-68-7 ]
Reference：
[1] Journal of Organic Chemistry, 1984, vol. 49, p. 2728 - 2733
[2] Journal of the Chemical Society, Chemical Communications, 1981, # 16, p. 817 - 818
24
[ 22364-68-7 ]
[ 74-88-4 ]
[ 58422-60-9 ]
Reference：
[1] European Journal of Organic Chemistry, 2018, vol. 2018, # 14, p. 1726 - 1729
[2] Collection of Czechoslovak Chemical Communications, 1992, vol. 57, # 9, p. 1967 - 1981
[3] Journal of Organic Chemistry, 1983, vol. 48, # 22, p. 4087 - 4096
Reference：
[1] Angewandte Chemie - International Edition, 2018, vol. 57, # 36, p. 11770 - 11775[2] Angew. Chem., 2018, vol. 130, # 36, p. 11944 - 11949,6
27
[ 616-38-6 ]
[ 22364-68-7 ]
[ 58422-60-9 ]
Reference：
[1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 10, p. 1323 - 1328
[2] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1994, # 10, p. 1323 - 1328
[3] Recueil des Travaux Chimiques des Pays-Bas-Journal of the Royal Netherlands, 1996, vol. 115, # 4, p. 256 - 260
28
[ 22364-68-7 ]
[ 58422-60-9 ]
Reference：
[1] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 2283;engl.Ausg.S.2320[2] Zhurnal Obshchei Khimii, 1959, vol. 29, p. 1728,1736;engl.Ausg.S.1706,1712
[3] Journal of the Chemical Society, 1956, p. 808,809
[4] Journal of the Chemical Society, 1956, p. 808,809
29
[ 22364-68-7 ]
[ 74-88-4 ]
[ 58422-60-9 ]
[ 30568-28-6 ]
Reference：
[1] Farmaco, Edizione Scientifica, 1980, vol. 35, # 8, p. 684 - 690
With 1-butyl-3-methylimidazolium hydrogen sulfate; water at 60 - 65℃; for 1.25h; Green chemistry;
General procedure for the synthesis of carboxylic acids from nitriles
General procedure: Aromatic or aliphatic nitriles (2 mmol) were dissolved in 5 ml of [bmim]HSO4 and the reaction mixture was heated at 60-65 °C for 1-3 h. The progress of reaction was monitored by TLC. After completion of reaction, as checked by TLC, the reaction mixture was poured into water containing crushed ice. The product was precipitated out, filtered and dried. The yield of the final product was high (>90%) in all cases. All final products obtained were found sufficiently pure so it didn’t need further purification.The filtrate was concentrated under vacuum, washed with diethylether twice and concentrated under high vacuum. After proper drying under reduced pressure, approximately 95% ionic liquid was recovered from the reaction and compared with the original ionic liquid to check its authenticity. The efficiency of recovered ionic liquid in conversion of nitriles to acids was found unchanged in comparison to the original one and we reused it up to 5-6 cycles without any significant loss of its activity.
With sulfuric acid; acetic acid
With potassium hydroxide; dihydrogen peroxide Behandlung mit Salzsaeure;
With sulfuric acid
With sulfuric acid
In ethanol (alkaline hydrolysis);
Multi-step reaction with 2 steps
1: sodium hydroxide / 6 h / 95 °C
2: hydrogenchloride; water / 20 °C
(3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
35%
With potassium hydroxide; In methanol; water; acetic acid; ethyl acetate;
Synthesis Example 14 Synthesis of (3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile A solution of 128 g (2.3 mol) of potassium hydroxide in 364 g of methanol was cooled, to which 75 g (0.57 mol) of o-xylyl cyanide was added. Thereafter, a solution of 75 g (0.58 mol) of <strong>[609-40-5]<strong>[609-40-5]2-nitrothiophen</strong>e</strong> (purity 85%) in 218 g of methanol was added dropwise such that the temperature might not exceed 5 C. The solution was allowed to ripen for 30 minutes below 5 C., after which a solution of 551 g of glacial acetic acid in 2,200 g of water was added, and further 1,000 g of ethyl acetate added. The organic layer was separated. Ethyl acetate, 400 g, was added to the aqueous layer to effect extraction again. The organic layers were combined, washed with 200 g of saturated sodium chloride water two times, dried over anhydrous magnesium sulfate, and concentrated in vacuum, obtaining 125 g of an oily matter. It was purified by silica gel column chromatography (eluent, ethyl acetate:hexane=2:1 by volume). The elute was concentrated, followed by recrystallization from toluene, filtration and drying. There was obtained 49 g of yellow crystals (yield 35%). The compound was analyzed by nuclear magnetic resonance (NMR) spectroscopy and infrared (IR) absorption spectroscopy, with the data shown below. 1H-NMR: CDCl3 (ppm) 2.37 (3H, s, Ha) 6.09-6.11 (1H, d, Hf) 6.88-6.90 (1H, d, Hg) 7.20-7.36 (4H, m, Hb, Hc, Hd, He) 9.23 (1H, s, Hh) IR: cm-1 3253, 3075, 3016, 2958, 2825, 2208, 1540, 1521, 1483, 1456, 1423, 1386, 1330, 1290, 1257, 1232, 1101, 1068, 1012, 991, 844, 798, 763, 734, 723, 692, 678, 644
With N-Bromosuccinimide; dibenzoyl peroxide; In tetrachloromethane;Reflux;
Example 8 Preparation of intermediate R: A slurry of benzoyl peroxide (0.34 g, 0.98 mmol) and N-bromosuccinimide (6.8 g, 38 mmol) in carbon tetrachloride (40 mL) was heated to reflux, with stirring. To that slurry was added dropwise a solution of 2-methylphenylacetonitrile (5.0 g, 38 mmol) in carbon tetrachloride (30 mL). The resulting mixture was kept stirring at reflux for 4 h, and then cooled to room temperature, filtered, and concentrated under reduced pressure. The crude product so obtained was purified by flash chromatography (ethyl acetate/hexane) to afford R as a light yellow solid (3.2 g).
General procedure: To a stirred solution of compound 4a (700 mg, 5.18 mmol) in THF (10 mL) was added LiHMDS (6.2 ml, 1 M sol. in THF, 6.2 mmol) at 0 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (870 mg, 6.22 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at 0 C and stirred at rt for 4 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 10% ethyl acetate/pet ether gave the pure compound 5a (720 mg, 68% yield) as a colorless liquid.
With zinc perchlorate; In neat (no solvent); at 50℃; for 5h;
General procedure: A mixture of nitrile (5 mmol), <strong>[774-65-2]ter<strong>[774-65-2]t-butyl benzoate</strong></strong> (5.5 mmol) and Zn(ClO4)2·6H2O (2 mol%) was placed in around bottom flask. Then, the reaction mixture was heated at 50 C for the given time. After completion of the reaction monitored by thin layer chromatography (TLC), the reaction mixture was quenched with 5-ml water. Then the reaction system was added 10 ml aqueous NaOH solution (1 mol/L) and continued to be stirred 5 min and extracted with ethyl acetate (3 × 10 ml). The organic layers were collected, combined, washed with water (3 × 10 ml), driedover anhydrous Na2SO4, and concentrated under vacuum.
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