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[ CAS No. 57-15-8 ] {[proInfo.proName]}

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Chemical Structure| 57-15-8
Chemical Structure| 57-15-8
Structure of 57-15-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 57-15-8 ]

CAS No. :57-15-8 MDL No. :MFCD00004461
Formula : C4H7Cl3O Boiling Point : -
Linear Structure Formula :- InChI Key :OSASVXMJTNOKOY-UHFFFAOYSA-N
M.W : 177.46 Pubchem ID :5977
Synonyms :
Chloreton;Chloretone;Chlortran;Chlorbutol

Calculated chemistry of [ 57-15-8 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 36.97
TPSA : 20.23 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.94 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.8
Log Po/w (XLOGP3) : 2.03
Log Po/w (WLOGP) : 2.13
Log Po/w (MLOGP) : 1.89
Log Po/w (SILICOS-IT) : 1.77
Consensus Log Po/w : 1.92

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.15
Solubility : 1.25 mg/ml ; 0.00703 mol/l
Class : Soluble
Log S (Ali) : -2.08
Solubility : 1.47 mg/ml ; 0.00827 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.02
Solubility : 1.69 mg/ml ; 0.00951 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.18

Safety of [ 57-15-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57-15-8 ]

* 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.

  • Upstream synthesis route of [ 57-15-8 ]
  • Downstream synthetic route of [ 57-15-8 ]

[ 57-15-8 ] Synthesis Path-Upstream   1~19

  • 1
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  • [ 80636-30-2 ]
YieldReaction ConditionsOperation in experiment
89% With N-benzyl-N,N-diethylethanaminium chloride; sodium hydroxide In dichloromethane; water at 0 - 20℃; Inert atmosphere General procedure: General procedure for the synthesis of 3a–3t: Representative procedure for 3h: 50percent aqueous sodium hydroxide (0.42 mL, 5 equiv) was added dropwise to astirred mixture of o-phenylene diamine 1a (CAUTION: toxic) (200 mg, 1 equiv),4-(trichloromethyl)tetrahydro-2H-pyran-4-ol (812 mg, 2 equiv) and N-benzyl-N,N-diethylethanaminium chloride (42 mg, 0.1 equiv) in CH2Cl2 (0.1 M) cooledto 0 °C over a period of 10–20 s under nitrogen. The resulting mixture wasstirred at 0 °C and left to warm to room temperature with stirring over 18 h.The reaction was monitored by analytical HPLC–MS. When complete, thereaction mixture was diluted with water (10 mL) until any solid had dissolvedand the layers were separated. The aqueous layer was extracted with CH2Cl2(3 20 mL). The combined organic layers were dried (MgSO4), ltered andevaporated to afford the crude product which was puried by ash silicachromatography, elution gradient 0–50percent EtOAc in heptane. The resulting solidwas ltered through a Buchner funnel, rinsed with MTBE (2 10 mL), andcollected to afford 10,2,3,40,5,6-hexahydro-30H-spiro[pyran-4,20-quinoxalin]-30-one (310 mg, 77percent) as a pale yellow powder.
Reference: [1] Tetrahedron Letters, 2016, vol. 57, # 39, p. 4386 - 4388
[2] Synthesis, 1982, # 1, p. 71 - 74
  • 2
  • [ 67-66-3 ]
  • [ 67-64-1 ]
  • [ 57-15-8 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1989, vol. 25, # 7.1, p. 1231 - 1237[2] Zhurnal Organicheskoi Khimii, 1989, vol. 25, # 7, p. 1369 - 1376
[3] Journal of Organic Chemistry, 2000, vol. 65, # 21, p. 7211 - 7212
[4] Monatshefte fuer Chemie, 1983, vol. 114, p. 813 - 816
[5] Monatshefte fuer Chemie, 1983, vol. 114, p. 813 - 816
[6] Journal of the American Pharmaceutical Association (1912-1977), vol. 28, p. 492[7] Chem. Zentralbl., 1939, vol. 110, # II, p. 4464
[8] Patent: US2462389, 1946, ,
[9] Patent: US2446453, 1943, ,
[10] Journal of the American Chemical Society, 1948, vol. 70, p. 1190
[11] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1901, vol. 133, p. 1011
[12] Chemische Berichte, 1881, vol. 14, p. 2451
[13] Journal fuer Praktische Chemie (Leipzig), 1888, vol. <2> 37, p. 367
[14] Roczniki Farm., vol. 2, p. 99[15] Chem. Zentralbl., 1924, vol. 95, # II, p. 304
[16] Sci.Rep.Tsing Hua Univ.<A>, 1931, vol. 1, p. 210[17] Chem. Zentralbl., 1932, vol. 103, # II, p. 3543
[18] Patent: US2446453, 1943, ,
[19] Journal of the American Chemical Society, 1948, vol. 70, p. 1190
[20] Die Farikation pharmazeutischer und chemisch-technischer Produkte <Berlin 1931>, S. 150,
[21] Journal of the Chemical Society [Section] C: Organic, 1966, p. 2166 - 2176
[22] Chemische Berichte, 1963, vol. 96, p. 426 - 431
[23] Chemische Berichte, 1977, vol. 110, p. 96 - 106
[24] Journal of the American Chemical Society, 2011, vol. 133, # 49, p. 19598 - 19601
[25] Patent: US2015/175520, 2015, A1, . Location in patent: Paragraph 0072
[26] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 17, p. 6566
  • 3
  • [ 3294-57-3 ]
  • [ 67-64-1 ]
  • [ 57-15-8 ]
Reference: [1] Journal of the American Chemical Society, 1965, vol. 87, # 3, p. 681 - 682
  • 4
  • [ 56-23-5 ]
  • [ 67-64-1 ]
  • [ 57-15-8 ]
Reference: [1] Zeitschrift fuer Chemie (Stuttgart, Germany), 1980, vol. 20, # 12, p. 442 - 443
[2] Tetrahedron Letters, 1986, vol. 27, # 27, p. 3129 - 3132
  • 5
  • [ 917-64-6 ]
  • [ 76-02-8 ]
  • [ 57-15-8 ]
Reference: [1] Roczniki Farm., vol. 2, p. 99[2] Chem. Zentralbl., 1924, vol. 95, # II, p. 304
  • 6
  • [ 67-66-3 ]
  • [ 67-64-1 ]
  • [ 57-15-8 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2312[2] Chemische Berichte, 1887, vol. 20, p. 2448
  • 7
  • [ 67-66-3 ]
  • [ 67-64-1 ]
  • [ 57-15-8 ]
Reference: [1] Chemische Berichte, 1882, vol. 15, p. 2312[2] Chemische Berichte, 1887, vol. 20, p. 2448
  • 8
  • [ 930-68-7 ]
  • [ 94-36-0 ]
  • [ 59992-07-3 ]
  • [ 57-15-8 ]
Reference: [1] Journal of the Chemical Society. Perkin Transactions 2, 1998, # 6, p. 1423 - 1429
  • 9
  • [ 7664-41-7 ]
  • [ 594-65-0 ]
  • [ 57-15-8 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1912, vol. 155, p. 1252[2] Bulletin de la Societe Chimique de France, 1914, vol. <4>15, p. 730
  • 10
  • [ 512-47-0 ]
  • [ 7664-93-9 ]
  • [ 75-87-6 ]
  • [ 57-15-8 ]
Reference: [1] Patent: DE151188, , ,
  • 11
  • [ 67-56-1 ]
  • [ 57-15-8 ]
  • [ 13836-62-9 ]
YieldReaction ConditionsOperation in experiment
48%
Stage #1: With potassium hydroxide In water at 0℃; for 5.15 h;
Stage #2: With hydrogenchloride In water
The procedure of Weizmann, Sulzbacher, and Bergmann as written in JA CS 70,1153 (1948), which is hereby incorporated by reference, was used as follows: A solution of potassium hydroxide (8.96 g, 159.7 mmol) in 5 mL of water and 20 mL of methanol was stirred with ice bath cooling under nitrogen as l,l,l-trichloro-2- methylpropan-2-ol (7.10 g, 40.0 mmol) was carefully added dropwise over ten min. Vigorous bubbling was observed as a white precipitate formed. The ice bath was removed after 15 min. The reaction was stirred at room temperature for 2 h then refluxed for 3 h. The reaction was cooled to room temperature and the solids were then removed by filtration and rinsed with methanol (350 mL). The filtrate was concentrated under vacuum EPO <DP n="44"/>to remove methanol and the remaining aqueous layer was brought to pH 0 by the addition of aqueous HCl then extracted with ethyl acetate (300 mL). The extract was dried (Na2SO4) and concentrated in vacuo to yield 4.11 g of crude product, which was purified by vacuum distillation to yield 2.28 g (48percent) of the pure title compound as a colorless oil which was distilled at 105 0C (28 mm Hg). 1HNMR (CDCl3) δ 9.65 (s, IH), 3.20 (s, 3H) and 1.32 ppm (s, 3H).
48% at 0 - 20℃; for 5.25 h; Heating / reflux Intermediate N : Preparation of 7V-[4-(chloromethyl)pyridin-2-yl]-2-methoxy-2-methylpropanamide; Step 1 : Preparation of 2-methoxy-2-methylpropanoic acid; The procedure of Weizmann, Sulzbacher, and Bergmann as written in JACS 70,1153 (1948), which is hereby incorporated by reference, was used as follows: A solution of potassium hydroxide (8.96 g, 159.7 mmol) in 5 mL of water and 20 mL of methanol was stirred with ice bath cooling under nitrogen as l,l,l-trichloro-2-methylpropan-2-ol (7.10 g, 40.0 mmol) was carefully added dropwise over ten min. Vigorous bubbling was observed as a white precipitate formed. The ice bath was removed after 15 min. The reaction was stirred at room temperature for 2 h then refluxed for 3 h. The reaction was cooled to room temperature and the solids were then removed by filtration and rinsed with methanol (350 mL). The filtrate was concentrated under vacuum to remove methanol and the remaining aqueous layer was brought to pH 0 by the addition of aqueous HC1 then extracted with ethyl acetate (300 mL). The extract was dried (NaaSC^) and concentrated in vacuo to yield 4.1 1 g of crude product, which was purified by vacuum distillation to yield 2.28 g (48percent) of the pure title compound as a colorless oil which was distilled at 105 °C (28 mm Hg). 1HNMR (CDC13) 8 9.65 (s, 1H), 3.20 (s, 3H) and 1.32 ppm (s, 3H).
48% With potassium hydroxide In water at 20℃; for 5 h; Heating / reflux Preparation of 2-methoxy-2-methylpiOpanoic acid The procedure of Weizmann, Sulzbacher, and Bergmann as written in JACS 70,1153 (1948), which is hereby incorporated by reference, was used as follows: A solution of potassium hydroxide (8.96 g, 159.7 mmol) in 5 mL of water and 20 niL of methanol was stirred with ice bath cooling under nitrogen as 1,1 , l-trichloro-2- methylpropan-2-ol (7.10 g, 40.0 mmol) was carefully added dropwise over ten min. Vigorous bubbling was observed as a white precipitate formed. The ice bath was removed after 15 min. The reaction was stirred at room temperature for 2 h then refluxed for 3 h. The reaction was cooled to room temperature and the solids were then removed by filtration and rinsed with methanol (350 mL). The filtrate was concentrated under vacuum to remove methanol and the remaining aqueous layer was brought to pH 0 by the addition of aqueous HCl then extracted with ethyl acetate (300 mL). The extract was dried (Na2SO4) and concentrated in vacuo to yield 4.11 g of crude product, which was purified by vacuum distillation to yield 2.28 g (48percent) of the pure title compound as a colorless oil which was distilled at 105 C (28 mm Hg). 1HNMR (CDCl3) ? 9.65 (s, IH), 3.20 (s, 3H) and 1.32 ppm (s, 6H).
Reference: [1] Patent: WO2006/96338, 2006, A1, . Location in patent: Page/Page column 42-43
[2] Patent: WO2006/2383, 2006, A2, . Location in patent: Page/Page column 50-51
[3] Patent: WO2006/133006, 2006, A2, . Location in patent: Page/Page column 47-48
[4] European Journal of Organic Chemistry, 2007, # 21, p. 3449 - 3462
[5] Journal of the American Chemical Society, 1948, vol. 70, p. 1157
[6] Patent: GB578082, 1943, ,
[7] Journal of the Chemical Society [Section] C: Organic, 1966, p. 2166 - 2176
  • 12
  • [ 17356-08-0 ]
  • [ 57-15-8 ]
  • [ 13836-62-9 ]
  • [ 4695-19-6 ]
Reference: [1] Canadian Journal of Chemistry, 1980, vol. 58, p. 2784 - 2788
  • 13
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  • [ 13836-62-9 ]
  • [ 4695-19-6 ]
Reference: [1] Canadian Journal of Chemistry, 1980, vol. 58, p. 2784 - 2788
  • 14
  • [ 124-41-4 ]
  • [ 57-15-8 ]
  • [ 13836-62-9 ]
Reference: [1] Journal of the American Chemical Society, 1948, vol. 70, p. 1157
[2] Journal of the American Chemical Society, 1947, vol. 69, p. 2669
[3] Journal of the American Chemical Society, 1948, vol. 70, p. 1157
[4] Patent: GB578082, 1943, ,
  • 15
  • [ 106-48-9 ]
  • [ 57-15-8 ]
  • [ 882-09-7 ]
Reference: [1] Canadian Journal of Chemistry, 1989, vol. 67, p. 1472 - 1479
  • 16
  • [ 57-15-8 ]
  • [ 108-95-2 ]
  • [ 943-45-3 ]
YieldReaction ConditionsOperation in experiment
38% With sodium hydroxide In acetone at 0 - 20℃; for 4 h; [0270] Step 1: 2-Methyl-2-phenoxypropionic acid 6 was prepared following the procedure of Corey et al., J. Am. Chem. Soc. 1969;91 :4782. To an ice-cold, stirred suspension of powdered NaOH (3.2 g, 80 mmol) in acetone (40 mL) was added phenol (1.88 g, 20 mmol) followed by 1, 1, 1-trichloro-2-methyl-2-propanol hydrate (7.82 g, 40 mmol). The mixture was stirred at 0° C. for 2 hours and then at room temperature for 2 hours. The mixture was diluted with H2O, acidified with 2N HCl, and extracted with EtOAc. The organic layer was washed with 2 N HCl, then extracted with saturated NaHCO3 (2.x.). The aqueous extracts were combined, washed once with EtOAc, acidified with 2N HCl, then extracted with EtOAc (2.x.). The combined organic layers were washed once with saturated NaCl, dried (MgSO4), and concentrated under reduced pressure. Purification by flash chromatography gave 6 (1.36 g, 38percent): 1H NMR (300 MHz, CDCl3) δ 7.28 (t, J=8 Hz, 2H), 7.08 (t, J=8 Hz, 1H), 6.96 (d, J=8 Hz, 2H), 1.52 (s, 6H).
Reference: [1] Patent: US2003/236286, 2003, A1, . Location in patent: Page 18
  • 17
  • [ 56-23-5 ]
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  • [ 57-15-8 ]
  • [ 108-95-2 ]
  • [ 943-45-3 ]
Reference: [1] Fortschr. Teerfarbenfabr. Verw. Industriezweige, vol. 4, p. 105
  • 18
  • [ 108-90-7 ]
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  • [ 64220-40-2 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 6101,6104
  • 19
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  • [ 39109-72-3 ]
  • [ 64220-40-2 ]
Reference: [1] Journal of the American Chemical Society, 1956, vol. 78, p. 6101,6104
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