Tag: M.W=100-200

Synthetic Route of 426831-32-5, 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 426831-32-5, name is (5-Fluoro-2-methoxyphenyl)methanol. This compound has unique chemical properties. The synthetic route is as follows.

Step 2: To 43 (1 eq, 17.9 mmol, 2.8 g) in CHCU (18 ml_) at room temperature, added HBr (22 mL) and the reaction mixture was stirred 2h, then diluted with dichloromethan, washed with water then brine, dried over sodium sulfate, and concentrated in vacuo to give 44 (3.3 g) as an off-white solid.

According to the analysis of related databases, 426831-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SCHERING CORPORATION; BOGEN, Stephane, L.; MA, Yao; WANG, Yaolin; LAHUE, Brian Robert; NAIR, Latha, G.; SHIZUKA, Manami; VOSS, Matthew Ernst; KIROVA-SNOVER, Margarita; PAN, Weidong; TIAN, Yuan; KULKARNI, Bheemashankar, A.; GIBEAU, Craig, R.; LIU, Yuan; SCAPIN, Giovanna; RINDGEN, Diane; DOLL, Ronald, J.; GUZI, Timothy, J.; HICKLIN, Danny, J.; NOMEIR, Amin; SEIDEL-DUGAN, Cynthia; SHIPPS, Gerald, W., Jr.; MACCOSS, Malcolm; WO2011/46771; (2011); A1;,
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Adding a certain compound to certain chemical reactions, such as: 10160-24-4, 7-Bromo-1-heptanol, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound, Application In Synthesis of 7-Bromo-1-heptanol, blongs to alcohols-buliding-blocks compound. Application In Synthesis of 7-Bromo-1-heptanol

To a stirred solution of (S)-3- (1-CARBAMOYL-1,1-DIPHENYLMETHYL)pyrrolidine (40 g, 142.7 mmol) and triethylamine (59.6 mL, 428 mmol) in acetonitrile (1. 1 L) at 40C under a nitrogen atmosphere was added 7-bromo-1-heptanol (24 mL, 146 mmol) in acetonitrile (100 mL) dropwise. The reaction mixture was heated to 50C for 9 hours. The reaction mixture was allowed to cool before removing the solvent under reduced pressure. The crude residue was dissolved in dichloromethane (500 mL) and the organic layer washed with saturated aqueous sodium bicarbonate (2 x 300 mL), followed by water (300 mL) and saturated aqueous sodium chloride (300 mL), and then dried over magnesium sulfate (10 g). The magnesium sulfate was filtered off and washed with dichloromethane (100 mL). The solvent was then removed in vacuo to give the crude product which was purified on a short column (SIO2) by varying the eluant from 19: 1: 0.1 to 3: 1: 0.1 CH2CL2/MEOH/NH40H to give 31.35 g of the title intermediate as a white solid (56% yield ; >95% purity by HPLC Method A).

The synthetic route of 10160-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THERAVANCE, INC.; WO2004/41806; (2004); A2;,
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Related Products of 122763-67-1 ,Some common heterocyclic compound, 122763-67-1, molecular formula is C9H16O3, 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.

Vinyl acetate (15.6mL, 169.6mmol) was added to a solution of 1 (9.75g, 56.7mmol) in pentane (120mL). Amano lipase (from Burkholderia cepacia (6.2g) and MS 4 (8.9g) were added and the suspension was stirred at 30C for 16h. The reaction mixture was monitored by TLC. The lipase and sieves were filtered and washed with Et2O. The solvent was removed and the crude product was purified by silica gel column chromatography (EtOAc/Petroleum ether 1:9) to afford 1 (R) (4.4g, 25.6mmol, 45%) and 3 (S) (5.1g, 23.8mmol, 42%). 1 (R): [alpha]20D=+4.1 (c=1.04, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.83 (ddd, J=16.0, 10.5, 5.5Hz, 1H, CH=CHaHb), 5.25 (dt, J=17.2, 1.5Hz, 1H, CH=CHaHb), 5.09 (dt, J=10.5, 1.4Hz, 1H, CH=CHaHb), 4.45 (m, 1H, CHOH), 3.2 (br s, 1H, CHOH), 2.47 (dd, J=16.1, 4.7Hz, 1H, COCHaHb), 2.38 (dd, J=16.1, 7.7Hz, 1H, COCHaHb), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=171.7, 139.0, 115.2, 81.4, 69.1, 42.2, 28.1ppm. IR (film): numax=3434, 2979, 2931, 1726, 1645, 1393, 1368, 1256, 1157, 1039, 993, 924, 842, 763cm-1. HRMS (ESI): calcd for C9H16O3 [M+Na]+ 195.0997 found 195.1002. 3 (S): [alpha]20D=-5.5 (c=1.09, CHCl3). 1H NMR (250MHz, CDCl3): delta=5.81 (ddd, J=17.0, 10.5, 6.2Hz, 1H, CH=CHaHb), 5.59 (m, 1H, CHOCOCH3), 5.28 (dt, J=17.2, 1.2Hz, 1H, CH=CHaHb), 5.18 (dt, J=10.5, 1.2Hz, 1H, CH=CHaHb), 2.60 (dd, J=15.3, 7.9Hz, 1H, tBuOCOCHaHb), 2.50 (dd, J=15.3, 5.9Hz, 1H, tBuOCOCHaHb), 2.04 (s, 3H, OCOCH3), 1.42 (s, 9H, t-Bu) ppm. 13C NMR (62.5MHz, CDCl3): delta=169.9, 169.1, 135.3, 117.4, 81.2, 71.2, 40.8, 28.1, 21.2ppm. IR (film): numax=2979, 2933, 1736, 1646, 1457, 1369, 1290, 1235, 1159, 1024, 991, 947, 847, 764cm-1. HRMS (ESI): calcd for C11H18O4 [M+Na]+ 237.1103 found 237.1109.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,122763-67-1, its application will become more common.

Reference:
Article; Menhour, Boudjema; Akong, Firmin Obounou; Mayon, Patrick; Ple, Karen; Bouquillon, Sandrine; Dorey, Stephan; Clement, Christophe; Deleu, Magali; Harakat, Dominique; Haudrechy, Arnaud; Tetrahedron; vol. 72; 47; (2016); p. 7488 – 7495;,
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Reference of 27129-87-9, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 27129-87-9 as follows.

1-(chloromethyl)-3,5-dimethylbenzene was prepared from (3,5-dimethylphenyl)methanol and thionyl chloride: thionyl chloride (300 muL, 4.13 mmol, 11.8 M) and (3,5-dimethylphenyl)methanol (50 muL, 0.39 mmol, 1.1 M) were added to a NMR tube, capped. Teflon wrapping around the cap of nmr tube was used to prevent reaction mixture from leaking out. The NMR tube was heated at reflux under air (100 C) for 10 min. After cooling to 23 C, the nmr cap was replaced by a septum and volatiles were removed under vacuum via a needle through the septum. A solution (300 muL) of (1,4-bis(trifluoromethyl)benzene in C6D6 was added to the product mixture for 1H{13C} NMR analysis. All (3,5-dimethylphenyl)methanol was converted at the end of reaction. 1H{13C} NMR chemical shifts of 1-(chloromethyl)-3,5-dimethylbenzene: 6.75 ppm (2H, arene CH, s), 6.68 ppm (1H, arene CH, s), 4.15 ppm (2H, CH2Cl, s), 2.04 ppm (6H, benzylic CH3, s). 13C{1H} NMR chemical shifts of 1-(chloromethyl)-3,5-dimethylbenzene: 138.3 (s), 138.8 ppm (s),130.7 ppm (s), 127.4 ppm (s), 46.97 ppm, 21.65 ppm (s).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,27129-87-9, its application will become more common.

Reference:
Article; Zhou, Meng; Goldman, Alan S.; Molecules; vol. 20; 6; (2015); p. 10122 – 10130;,
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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. 68327-04-8, name is (1S,2S)-2-Aminocyclopentanol hydrochloride. A new synthetic method of this compound is introduced below., Quality Control of (1S,2S)-2-Aminocyclopentanol hydrochloride

To a chilled solution of 4-(5-(2,4-difluorobenzyl)-1-(2-fluorobenzyl)-2-oxo-1,2-dihydropyridin-3-yl)-4-hydroxy-2-oxobut-3-enoic acid (1) (150 mg, 0.338 mmol) in dimethylformamide (DMF) (2.0 mL), was added hydroxybenzotriazole (HOBT) (50 mg, 0.372 mmol), followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI-HCl, 71 mg, 0.372 mmol) and the mixture was stirred for 30 min. A solution of (1S,2S)-(+)-trans-2-aminocyclopentanol hydrochloride and NaHCO3 (31 mg, 0.372 mmol) was added followed by stirring for 2 h at 0-5 C. Cold water was added to the reaction mixture, which was then extracted with ethyl acetate (2 × 20 mL). The combined organic phase was separated, washed with water twice, then once with 1 N HCl solution, and finally with saturated aqueous NaHCO3 solution. Concentration in vacuo afforded the crude product which was passed through a short silica gel column with chloroform as the eluting solvent. The eluent containing the product was concentrated and the resulting residue was triturated with hexanes, which afforded the product as a yellow solid in 117 mg (66%), mp 61-63 C, [alpha]20D[alpha]D20 +41.8 (c 0.01, methanol), UV lambdamax 396 nm (epsilon 14,455, methanol). 1H NMR (CDCl3, 500 MHz): delta 15.33 (br s, 1H), 8.16 (d, 1H, J = 2.0 Hz), 8.08 (s, 1H), 7.61-6.85 (m, 9H), 5.22 (s, 2H), 4.11 (m, 1H), 3.94 (m, 1H), 3.78 (s, 1H), 2.23 (m, 1H), 2.10 (m, 1H), 1.88 (m, 1H), 1.78 (m, 2H), 1.59 (m, 1H). 13C NMR (CDCl3, 125 MHz): delta 181.3, 180.6, 163.4, 163.3, 162.4, 162.1, 162.0, 161.4, 161.3, 160.4, 160.1, 160.0, 159.2, 145.5, 143.9, 142.3, 141.6, 132.4, 132.4, 132.3, 131.5, 131.4, 131.3, 131.3, 131.2, 130.7, 130.6, 125.0, 124.9, 124.8, 122.8, 122.7, 122.5, 122.2, 122.2, 122.1, 122.1, 117.1, 115.9, 115.7, 115.6, 111.9, 111.9, 111.8, 111.7, 104.7, 104.5, 104.3, 98.3, 79.5, 79.3, 61.0, 60.6, 51.5, 47.7, 47.3, 32.9, 32.8, 32.7, 30.8, 30.7, 30.5, 21.7, 21.5. HRMS: calcd for C28H26F3N2O5 (M+H), 527.1794; found 527.1799.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it, 68327-04-8, (1S,2S)-2-Aminocyclopentanol hydrochloride.

Reference:
Article; Okello, Maurice; Mishra, Sanjay; Nishonov, Malik; Nair, Vasu; Bioorganic and Medicinal Chemistry Letters; vol. 23; 14; (2013); p. 4112 – 4116;,
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Application of 1805-32-9 ,Some common heterocyclic compound, 1805-32-9, molecular formula is C7H6Cl2O, 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: To a solution of alcohol (1mmol) in 2mL of toluene was added GO (0.3g). The resulting mixture was sonicated in an Elmasonic P ultrasonic cleaning unit (ultrasonic bath) with a frequency of 37kHz and 100% output power at 80C for the time indicated in Table 4. Then Oxone (1mmol) and 2mL of an alcoholic solvent was added in the reaction medium and the resulting mixture was irradiated for the time indicated in Table 4. The mixture was filtered through a sintered funnel and evaporated under reduced pressure, and extracted with ethyl acetate. The organic layer was dried over Na2SO4, filtered and evaporated under reduced pressure. Purification was achieved by column chromatography using n-hexane/EtOAc: 100/3 as eluent. The spectroscopic data of the obtained esters were compared with authentic samples [5,40,42,43]. Spectroscopic data for methyl 3,4-dichlorobenzoate (entry 9, Table 4): Pale yellow, M.P. 44.7C; IR (KBr) nu=3089, 3022, 2958, 1729, 1589, 1435, 1378, 1301, 1110, 757cm-1; 1H NMR (300MHz, CDCl3) delta=3.94 (s, 3H, CH3), 7.53 (d, J=8.3Hz, 1H, CH Arom), 7.87 (dd, J=8.3, 1.9Hz, 1H, CH Arom), 8.13 (d, J=1.9Hz, 1H, CH Arom); 13C NMR (75MHz, CDCl3) delta=52.54, 128.63, 129.94, 130.52, 131.53, 132.92, 137.56, 165.21; MS (EI) (70eV), m/z (%): 208 (5) [M+4]+, 206 (31) [M+2]+, 204 (50) [M]+, 177 (10), 175 (62), 173 (100), 145 (30), 109 (20), 74 (18).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1805-32-9, its application will become more common.

Reference:
Article; Mirza-Aghayan, Maryam; Zonoubi, Somayeh; Molaee Tavana, Mahdieh; Boukherroub, Rabah; Ultrasonics Sonochemistry; vol. 22; (2015); p. 359 – 364;,
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Related Products of 1562-00-1 ,Some common heterocyclic compound, 1562-00-1, molecular formula is C2H5NaO4S, 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 sodium isethionate is combined with the post-treatment mother liquor. Add ammonia gas, liquid ammonia or aqueous ammonia. The ammonia content is controlled 24 ~ 34% (w/v). Pump into the synthesis tower. The residence time of the material in the tower is not less than 0.5 to 1 hour. Sodium isethionate undergoes ammonolysis to become sodium taurinate; At the same time, solution of sodium isethionate ethylene glycol-type by-product undergoes high temperature and pressure reaction and are converted into polyether alcohol-type by-product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1562-00-1, its application will become more common.

Reference:
Patent; Jiangyin Huachang Food Additive Co., Ltd.; Zhang, Huaxing; Zhang, Yugao; Xia, Jianhua; (9 pag.)CN105732440; (2016); A;,
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Synthetic Route of 112-27-6, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 112-27-6 as follows.

To a mixture of Ag2O (12.4 g, 100 mmol) and KI (4.42 g, 26.64 mmol) in DCM (200 mL) was added 2,2?-(ethane-1,2-diylbis(oxy))diethanol (10 g, 66.6 mmol) dropwise at room temperature. Then BnBr (12.5 g, 73.26 mmol) was added dropwise into the mixture over 10 min. After addition, the mixture was stirred at room temperature for 2 h. The reaction mixture was filtered. The combined filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethanol (7 g, 43.8%) as a colorless oil. LC/MS (ESI, m/z): [M+1]+=241.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,112-27-6, its application will become more common.

Reference:
Patent; Kymera Therapeutics, Inc.; Ji, Nan; Kluge, Arthur F.; Weiss, Matthew M.; Zhang, Yi; (180 pag.)US2020/10468; (2020); A1;,
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Related Products of 1562-00-1, Adding some certain compound to certain chemical reactions, such as: 1562-00-1, name is Sodium isethionate,molecular formula is C2H5NaO4S, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 1562-00-1.

General procedure: Synthesis of [CmOHMIM][HOCnSO3]) and [CmOHTEA][HOCnSO3]: ILs were prepared by ion exchange method. The ion exchange of the anion chloride by the anion hydroxyalkanesulphonate was carried out using an exchange column packed with 100 g of Amberlite IR120 H-type strongly acidic cation exchange resin. The column was previously flushed thoroughly with a 1 mol L- 1 [CmOHMIM]Cl or [CmOHTEA]Cl solution until the elution was neutral, then with Milli-Q water until no chloride was detected by silver nitrate. A 100 mL of 1 mol L- 1 Na[HOCnSO3] solution was slowly run over and eluted with Milli-Q water. The eluted liquid was collected and concentrated under reduced pressure in a rotary evaporator. The residue was then vacuum dried at 323 K for 18 h to afford the IL in near-quantitative yield as a colorless viscous liquid. ILs with ions containing hydroxyl groups are usually observed to be rather viscous. 1-(2-Hydroxyethyl)-3-methyl-imidazolium hydroxymethane sulfonate ([C2OHMIM][HOC1SO3]) 1H NMR (400 MHz, D2O, 298 K): 3.89 (s, 3H), 3.91 (t, J = 5.0 Hz, 2H), 4.30 (t, J = 4.83 Hz, 2H), 4.35 (s, 2H), 7.44 (s, 1H), 7.50 (s, 1H), 8.72 (s, 1H); 13C NMR (400 MHz, D2O, 298 K): 35.29, 51.08, 59.35, 73.71, 122.01, 123.18, 135.92. ES-MS: ES+ m/z 127.00 [C2OHMIM]+, 288.87 [C2OHMIM]+?H3O2-?[C2OHMIM]+; ES- m/z 110.80 [HOC1SO3]-, 244.73 [HOC1SO3]-?H3O+?[HOC1SO3]-, 352.80 [HOC1SO3]-?[C2OHMIM]+?[HOC1SO3]-. 1-(2-Hydroxyethyl)-3-methyl-imidazolium 2-hydroxyethane sulfonate ([C2OHMIM][HOC2SO3]) 1H NMR (400 MHz, D2O, 298 K): 3.11 (t, J = 6.64 Hz, 2H), 3.89 (s, 3H), 3.89-3.91 (overlapped, 4H), 4.30 (t, J = 4.84 Hz, 2H), 7.44 (s, 1H), 7.50 (s, 1H), 8.73 (s, 1H); 13C NMR (400 MHz, D2O, 298 K): 35.28, 51.08, 52.44, 56.53, 59.34, 122.01, 123.18, 135.92. ES-MS: ES+ m/z 127.00 [C2OHMIM]+, 288.87 [C2OHMIM]+?H3O2-?[C2OHMIM]+, 378.80 [C2OHMIM]+?[HOC2SO3]-?[C2OHMIM]+; ES- m/z 124.93 [HOC2SO3]-, 272.87 [HOC2SO3]-?H3O+?[HOC2SO3]-, 376.67 [HOC2SO3]-?[C2OHMIM]+?[HOC2SO3]-. 3-Hydroxypropyl-tri(2-hydroxyethyl) ammonium 2-hydroxyethane sulfonate ([C3OHTEA][HOC2SO3]) 1H NMR (Brueker AV-600, 600 MHz, D2O, 298 K): 1.92-1.93 (m, -OH), 3.06 (t, J = 6.55 Hz, 2H), 3.36 (not resolved, 2H), 3.50-3.51 (m, 2H), 3.58 (not resolved, 6H), 3.86 (not resolved, 6H), 3.96 (not resolved, 4H); 13C NMR (Brueker AV-600, 600 MHz, D2O, 298 K): 24.61, 52.99, 55.06, 55.38, 55.47, 57.10, 58.36, 58.58, 61.25. ES-MS (AB SCIEX Triple TOF 5600 +): ES+ m/z 208.1578 [C3OHTEA]+, 266.2013 Na+?H3O2-?[C3OHTEA]+; ES- m/z 124.9882 [HOC2SO3]-.

According to the analysis of related databases, 1562-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Ou, Guangnan; He, Biyan; Halling, Peter; Biochimica et Biophysica Acta – General Subjects; vol. 1860; 7; (2016); p. 1404 – 1408;,
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Related Products of 59854-12-5 , The common heterocyclic compound, 59854-12-5, name is tert-Butyl 4-hydroxybutanoate, molecular formula is C8H16O3, 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.

Targeting tripodal tethers bearing easily removable protective groups in the side chains, we performed the synthesis of tether 10 (FIG. 13), where the malonic ester moieties are further elongated with C3 alkyl chains terminated by tert-butyl ester groups. In this case, selective hydrolysis of the ester moieties or focal deprotection (debenzylation) of the formed tris-adducts of C60 can give a facile access to structurally different derivatives. For this purpose, tert-butyl 4-hydroxybutyrate (8) was prepared (FIG. 13) and then subjected to a DCC monoesterification reaction with malonic acid to yield the mono-protected diacid 9. Three-fold esterification of trio 4 with acid 9 by using DCC and DMAP in CH2Cl2, afforded the tether 10 in 95% isolated yield.

The synthetic route of 59854-12-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hirsch, Andreas; Beuerle, Florian; Chronakis, Nikos; US2006/47167; (2006); A1;,
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