Month: June 2021

Synthetic Route of 675580-49-1, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 675580-49-1, name is (6-Chloroimidazo[1,2-b]pyridazin-3-yl)methanol. A new synthetic method of this compound is introduced below.

To a solution of (6-chloro-imidazo[1 ,2-b]pyridazin-3-yl)-methanol (1.3 g, 7.1 mmol) in DCM (50 ml_) was added active MnO2 (3 g, 34.5 mmol). The mixture was stirred at rt overnight and filtered. The filtrate was concentrated under vacuum and the residue was washed with EtOAc to affrode 6-chloro-imidazo[1 ,2-b]pyridazine-3-carbaldehyde (0.7 g) in 54% yield. 1H- NMR (400MHz, CDCI3) delta ppm 10.36 (s, 1 H), 8.42 (s, 1 H), 8.08 (d, 1 H), 7.38 (d, 1 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,675580-49-1, (6-Chloroimidazo[1,2-b]pyridazin-3-yl)methanol, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; DAI, Miao; FU, Xingnian; HE, Feng; JIANG, Lei; LI, Yue; LIANG, Fang; LIU, Lei; MI, Yuan; XU, Yao-chang; XUN, Guoliang; YAN, Xiaoxia; YU, Zhengtian; ZHANG, Ji, Yue; WO2011/20861; (2011); A1;,
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Reference of 29683-23-6 , The common heterocyclic compound, 29683-23-6, name is Tetrahydro-2H-thiopyran-4-ol, molecular formula is C5H10OS, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

The compound obtained in (80 mg, 0.28 mmol), tetrahydro-2H-thiopyran-4-ol (33.1 mg, 0.28 mmol) and triphenylphosphine (110.2 mg, 0.42 mmol) were dissolved in THF (2.5 mL), which was then slowly added with diethyl azodicarboxylate (DEAD, 191 muL, 0.42 mmol) and stirred at room temperature for 19 hours. The resulting mixture was concentrated and purified by silica gel chromatography to obtain the title compound (white solid, 33.7 mg, 31% yield). 1H NMR (300 MHz, CDCl3) delta 8.02 (d, 1H), 7.97 (dd, 1H), 7.18 (d, 1H), 6.79 (d, 1H), 6.67 (d, 1H), 4.50 – 4.38 (m, 3H), 3.91 (s, 3H), 3.00 – 2.92 (m, 2H), 2.87 – 2.76 (m, 1H), 2.63 – 2.47 (m, 3H), 2.36 (s, 3H), 2.27 – 2.17 (m, 2H), 2.12 – 2.01 (m, 2H)

The synthetic route of 29683-23-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SK Chemicals Co., Ltd.; LEE, Ju Young; LEE, Jeong A; AHN, Jaeseung; RYU, Je Ho; HAN, Min-Young; YOO, Taekyung; SA, Joon Ho; KIM, Jae-Sun; (297 pag.)EP2963027; (2016); A1;,
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Electric Literature of 2043-47-2, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.2043-47-2, name is 1H,1H,2H,2H-Nonafluoro-1-hexanol, molecular formula is C6H5F9O, molecular weight is 264.0889, as common compound, the synthetic route is as follows.

Example 3In a 200-ml, three-necked glass reactor were placed 80 ml of methylene chloride, 10 g (38 mmol) of 3,3,4,4,5,5,6,6,6-nonafluorohexanol, 5 g (58 mmol) of methacrylic acid, 10 g (57 mmol) of benzenesulfonic acid chloride and 0.1 g of a polymerization inhibitor, Sumilizer GM. While the reaction temperature was kept at 40 C. or lower, 12 g (119 mmol) of triethylamine was added dropwise. After the completion of the dropwise addition, stirring was conducted at room temperature for 1 hour. At this point, the conversion was 99% and the selectivity was 99%.

Statistics shows that 2043-47-2 is playing an increasingly important role. we look forward to future research findings about 1H,1H,2H,2H-Nonafluoro-1-hexanol.

Reference:
Patent; TOKUYAMA CORPORATION; DAIKIN INDUSTRIES, LTD.; US2009/23948; (2009); A1;,
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Related Products of 7073-69-0, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.7073-69-0, name is 2-(2-Bromophenyl)propan-2-ol, molecular formula is C9H11BrO, molecular weight is 215.087, as common compound, the synthetic route is as follows.

To a mixture of methyl 2-bromobenzoate (20 g, 93.00 mmol, 13.07 mL, 1 eq) in THF (200 mL) was added dropwise MeMgBr (3 M, 65.10 mL, 2.1 eq) at 5C under N2. The mixture was stirred at 25C for 2 h and then quenched with aqueous NH4CI (200 mL). The aqueous phase was extracted with ethyl acetate (100 mL x 3). The combined organic phase was washed with brine (150 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by flash silica gel chromatography (ISCO; 120 g SepaFlash Silica Flash Column, Eluent of 0- 30% Ethyl acetate/Petroleum ethergradient, 80 mL/min) to afford 2-(2- bromophenyl)propan-2-ol (13 g, 60.44 mmol, 64.99% yield) as light-yellow oil. 1H NMR (CDCIs, 400 MHz): d 7.67 (d, J = 7.6 Hz, 1 H), 7.59 (d, J = 7.6 Hz, 1 H), 7.31 (t, J = 7.6 Hz, 1 H), 7.12 (t, = 7.6 Hz, 1 H), 1.77 (s, 6H) ppm. To a mixture of 2-(2- bromophenyl)propan-2-ol (12 g, 55.79 mmol, 1 eq) in THF (120 ml_) was added n- BuLi (2.5 M, 55.79 ml_, 2.5 eq) in one portion at -70C. The mixture was stirred at – 70C for 2 h. Then triisopropyl borate (20.99 g, 111.58 mmol, 25.65 ml_, 2 eq) was added to the mixture. The mixture was warmed to 20C and stirred for 15 h. The residue was poured into ice-water (w/w = 1/1) (10 ml_) and adjust to pH 5. The aqueous phase was extracted with ethyl acetate (10 mL x 3). The combined organic phase was washed with brine (15 mL), dried with anhydrous Na2S04, filtered and concentrated in vacuum. The residue was purified by flash silica gel chromatography (ISCO; 80 g SepaFlash Silica Flash Column, Eluent of 0-100% Ethyl (0480) acetate/Petroleum ethergradient, 100 mL/min) to afford 3,3-dimethylbenzo (0481) [c][1 ,2]oxaborol-1 (3H)-ol (9 g, 55.56 mmol, 99.6% yield) as crude yellow oil. 1H NMR (CDCIs, 400 MHz): d 9.00 (s, 1 H), 7.67 (d, J = 7.2 Hz, 1 H), 7.47-7.41 (m, 2H), 7.33- 7.31 (m, 1 H), 1.45 (s, 6H) ppm. To a mixture of 3,3-dimethylbenzo[c][1 ,2]oxaborol- 1 (3H)-ol (9 g, 55.56 mmol, 1 eq) in H2S04 (100 mL) was added HNOs (10.50 g, 166.67 mmol, 7.50 mL, 3 eq) at -20C. The mixture was stirred at -15C for 10 min. Ice-water (100 mL) was added to the mixture at -10C and stirred for 10 min. It was filtered and then the solid was washed by petroleum ether (50 mL) to afford crude 3,3-dimethyl-6-nitrobenzo[c][1 ,2]oxaborol-1 (3H)-ol (8 g, 38.65 mmol, 69.6% yield) as yellow solid. 150 mg of crude product was purified by pre-HPLC (column: Xtimate C18 150*25mm*5um; mobile phase: [water (10mM NH4HC03)-ACN]; B%: 10%-40%, 10.5 min) to afford the purified material of 3,3-dimethyl-6-nitrobenzo[c][1 ,2]oxaborol- 1 (3H)-ol (91 mg) as yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 9.47 (s, 1 H), 8.52 (d, J = 2.4 Hz, 1 H), 8.32 (dd, J = 8.4, 2.4 Hz, 1 H), 7.73 (d, J = 8.4 Hz, 1 H), 1.49 (s, 6H) ppm. MS (ESI): mass calcd. For C9HI0BNO4 207.07, m/z found 206.1 [M-H] HPLC purity: 100% (220 nm) and 100% (254 nm). To a solution of 3,3-dimethyl-6- nitrobenzo[c][1 ,2]oxaborol-1 (3H)-ol (2 g, 9.66 mmol, 1 eq) in EtOAc (70 mL) was added Pd/C (0.5 g, 10% purity) under N2. The suspension was degassed under vacuum and purged with H2 several times. The mixture was stirred under H2 (15 psi) at 20C for 15 h. The reaction mixture was filtered, and the filtrate was concentrated to affrord 6-amino-3,3-dimethylbenzo[c][1 ,2] oxaborol-1 (3H)-ol (1.5 g, 8.47 mmol, 87.70% yield) as red solid. 100 mg of the crude product was purified by pre-HPLC (column: Xtimate C18 150*25mm*5um; mobile phase: [water (10mM NH4HC03)- ACN]; B%: 10%-40%, 10.5 min) to afford 6-amino-3,3-dimethylbenzo[c][1 ,2]oxaborol- 1 (3H)-ol (51 mg) as yellow solid. 1H NMR (DMSO-cfe, 400 MHz): d 8.73 (s, 1 H), 7.02 (d, J = 8.0 Hz, 1 H), 6.79 (d, J = 2.0 Hz, 1 H), 6.67 (dd, J = 8.0, 2.4 Hz, 1 H), 4.95 (s, 2H), 1.37 (s, 6H) ppm. MS (ESI): mass calcd. For C9Hi2BN02 177.10, m/z found 176.1 [M-H]-. HPLC: 99.4% (220 nm), 98.6% (254 nm). To a mixture of 6-amino-3,3- dimethylbenzo[c][1 ,2]oxaborol-1 (3H)-ol (1 g, 5.65 mmol, 1 eq) in t-BuOH (20 mL) was added (Boc)20 (3.70 g, 16.95 mmol, 3.89 mL, 3 eq) in one portion at 20C under N2. The mixture was stirred at 50C for 12 h and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography (ISCO; 12 g SepaFlash Silica Flash Column, Eluent of 0-80% Ethyl acetate/Petroleum ethergradient: 30 mL/min) to afford tert-butyl (1-hydroxy-3,3-dimethyl-1 ,3-dihydrobenzo[c][1 ,2]oxaborol- 6- yl)carbamate (0.6 g, 2.17 mmol, 38.32% yield) as yellow oil. 1H NMR (CDCh, 400 MHz): d 7.60 (s, 1 H), 7.54 (d, J = 8.0 Hz, 1 H), 7.21 (d, J = 8.0 Hz, 1 H), 6.53 (s, 1 H), 1.55 (s, 9H), 1.54 (s, 6H). To a mixture of tert-butyl (1 -hydroxy-3, 3-dimethyl-1 , 3- dihydrobenzo[c][1 ,2]oxaborol-6-yl)carbamate (0.5 g, 1.80 mmol, 1 eq) in DMF (10 mL) was added NCS (240.93 mg, 1.80 mmol, 1 eq) in one portions at 0C. The mixture was stirred at 50C for 15 h and then poured into water (10 mL). The aqueous phase was extracted with ethyl acetate (10 mL x 3). The combined organic phase was washed with brine (10 mL),…

The chemical industry reduces the impact on the environment during synthesis 7073-69-0, I believe this compound will play a more active role in future production and life.

Reference:
Patent; BORAGEN, INC.; LIU, Chunliang; ZHANG, Yong-Kang; LIU, Chun, Yu; ZHOU, Yasheen; (372 pag.)WO2020/51575; (2020); A1;,
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Related Products of 24034-73-9, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 24034-73-9, name is (2E,6E,10E)-3,7,11,15-Tetramethylhexadeca-2,6,10,14-tetraen-1-ol. This compound has unique chemical properties. The synthetic route is as follows.

Geranylgeraniol (600 mg, 2.07 mmol) and 15 mE of anhydrous tetrahydroffiran were added to a rubber septum coyered, oven-dried 50 mE round-bottom flask with a magneticstirring bar and a nitrogen inlet. The solution was stirred andcooled to -45 C. Upon cooling of this solution, methanesulfonyl chloride (207.5 pL, 2.67 mmol) was added slowlyvia syringe to the reaction flask. Over a 5-minute period,574.74 jiL of triethylamine was then added via syringe. Theresulting suspension was stirred for 45 minutes at -45 C. Asolution of lithium bromide (717.5mg, 8.26 mmol) inS mE oftetrahydroffiran was added dropwise via syringe. The suspen10 sion was warmed to 0 C. and stirred for 1 hout The reactionmixture was poured into 8 mE of iced water and the aqueouslayer was extracted with ice-cold diethyl ether (3×4 mE). Thecombined organic extracts were washed with ice-cold saturated NaHCO3 (10 mE) and brine (10 mE), and dried overanhydrous Mg504. The organic layer was filtered and concentrated in vacuo to obtain the crude geranylgeranyl bromide, which was then used immediately for the following stepwithout thrther purifications.

According to the analysis of related databases, 24034-73-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wellesley College; Carrico-Moniz, Dora; (19 pag.)US9388155; (2016); B1;,
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Electric Literature of 52273-77-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.52273-77-5, name is 2-(3-Aminophenyl)ethanol, molecular formula is C8H11NO, molecular weight is 137.179, as common compound, the synthetic route is as follows.

In a glass reaction flask are combined 73 grams of sublimed quinizarin (available from Aceto Corp., Lake Success, N.Y.), 49 grams of leucoquinizarin (available from Aceto Corp.), 66 grams of 3-aminobenzene ethanol (available from Frinton Labs, Vineland, N.J.), 31 grams of boric acid (available from Aldrich Chemical Co., Milwaukee, Wis.), and 780 grams of methanol (available from J T Baker, Phillipsburg, N.J.). The materials are mixed and heated until the solvent refluxes at about 66 C. After about 16 hours of reflux, it is believed that the reaction will be complete, having generated an alcohol-substituted colorant of the formula [CHEMMOL-00109] [0194] The reaction mixture is cooled and filtered. The product filter cake is dried in air at ambient temperature. The spectral strength of the alcohol-substituted colorant is determined using a spectrophotographic procedure based on the measurement of the colorant in solution by dissolving the colorant in toluene and measuring the absorbance using a Perkin Elmer Lambda 2S UV/VIS spectrophotometer. The spectral strength of the alcohol-substituted colorant is believed to be measured as about 21,000 mL Absorbance Units per gram at absorption lambdamax.

Statistics shows that 52273-77-5 is playing an increasingly important role. we look forward to future research findings about 2-(3-Aminophenyl)ethanol.

Reference:
Patent; Xerox Corporation.; US2004/82801; (2004); A1;,
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Related Products of 111-45-5, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.111-45-5, name is 2-(Allyloxy)ethanol, molecular formula is C5H10O2, molecular weight is 102.13, as common compound, the synthetic route is as follows.

Sodium hydroxide (2.56 g, 63.99 mmol) was completely dissolved in distilled water and a solution of THF and Allyloxy ethanol (5.83 ml, 54.55 mmol) was added at 0 C. After stirring for 30 minutes, a solution of 4-Toluenesulfonyl chloride (10 g, 52.45 mmol) in THF at 0 C was slowly added. After that, the temperature was raised to room temperature and then stirred for 1 hour. The reaction was terminated by adding cold distilled water and extracted with hexane. The extracted organic layer was washed with water and aqueous NaCl solution, and dried over MgSO4. The reaction product (1EO-OTs) was dried in a vacuum oven (Yield = 33%).

Statistics shows that 111-45-5 is playing an increasingly important role. we look forward to future research findings about 2-(Allyloxy)ethanol.

Reference:
Patent; Korea Research Institute of Chemical Technology; Han Mi-jeong; Kang Yeong-gu; Seok Jeong-don; Kwak Hyeon-ju; (29 pag.)KR101826496; (2018); B1;,
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Related Products of 440-60-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 440-60-8, name is (Perfluorophenyl)methanol, molecular formula is C7H3F5O, The compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

At 100mL2.95g (25mmol) of 2,3,4,5,6-pentafluorobenzyl alcohol was added to the three-necked flask.Triethylamine 2.5g,Toluene 40mL,Slow dropCis-2,2-dimethyl-3-(E/Z-2-chloropropenyl)cyclopropanecarboxylic acid chloride 6g (29mmol),The reaction was carried out at room temperature for 4 hours.The organic phase is sequentially 20mL5% sodium hydroxide solution,Wash with 5% hydrochloric acid solution and saturated sodium chloride solution, dry,After desolvation, a pale yellow viscous liquid is obtained.After column chromatography (petroleum ether / ethyl acetate = 20/1), 9.0 g of pale yellow liquid was obtained.The yield was 96%.

According to the analysis of related databases, 440-60-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mt. Huang College; Han Bingbing; Zheng Zubiao; (15 pag.)CN109776327; (2019); A;,
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Electric Literature of 647-42-7, With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.647-42-7, name is 3,3,4,4,5,5,6,6,7,7,8,8,8-Tridecafluorooctan-1-ol, molecular formula is C8H5F13O, molecular weight is 364.1, as common compound, the synthetic route is as follows.

Toluene (2 L), 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane-1-ol (2.18 kg, 6.0 mol), 2-methyl-2-propenic acid (methacrylic acid) (567 g, 6.6 mol) and 1,4-dihydroxybenzene (hydroquinone) (6.59 g, 60 mmol) were added and then p-toluenesulfonic acid monohydrate (148.06 g, 0.78 mol) was added thereto. The obtained solution was heated and subjected to reflux dehydration at 115 C. for 5 hours. After reflux dehydration, the obtained reaction solution was cooled to around room temperature and added with triethylamine (151.5 g, 1.50 mol) was added thereto, stirred for 0.5 hours and then added with 150 g of silica gel. After stirring for 0.5 hours, the silica gel was filtered off and the obtained filtrate was added with 1,4-dihydroxybenzene (hydroquinone) (1.32 g, 12.0 mmol), and the solvent was removed in vacuum distillation and then was purified in distillation to obtain 3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctane 2-methyl-2-propenic acid ester (2.44 kg, 94%).

The chemical industry reduces the impact on the environment during synthesis 647-42-7, I believe this compound will play a more active role in future production and life.

Reference:
Patent; WAKO PURE CHEMICAL INDUSTRIES, LTD.; US2010/324314; (2010); A1;,
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Electric Literature of 92093-23-7 ,Some common heterocyclic compound, 92093-23-7, molecular formula is C8H9BrO2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

General procedure: A diol 6c or 6d or 6e (2 equiv) and PPTS (0.1 equiv) was added to a toluene (25.0 mL/1 mmol of substrate) solution of a substituted-4,4-dimethoxycyclohexa-2,5-dienone 5a or 5b (1 equiv) at room temperature. After stirring at 40 C for 18 h, the reaction mixture was quenched by the addition of saturated aqueous NaHCO3 and the product was extracted with ethyl acetate three times. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate, filtered, and concentrated under reduced pressure. The residue was purified by preparative TLC to give the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92093-23-7, its application will become more common.

Reference:
Article; Fuse, Shinichiro; Inaba, Kennichi; Takagi, Motoki; Tanaka, Masahiro; Hirokawa, Takatsugu; Johmoto, Kohei; Uekusa, Hidehiro; Shin-ya, Kazuo; Takahashi, Takashi; Doi, Takayuki; European Journal of Medicinal Chemistry; vol. 66; (2013); p. 180 – 184;,
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