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Chemical Structure| 39478-78-9
Chemical Structure| 39478-78-9
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Product Details of [ 39478-78-9 ]

CAS No. :39478-78-9 MDL No. :MFCD00800678
Formula : C7H8BrN Boiling Point : -
Linear Structure Formula :- InChI Key :RXQNKKRGJJRMKD-UHFFFAOYSA-N
M.W :186.05 Pubchem ID :2734805
Synonyms :

Calculated chemistry of [ 39478-78-9 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 1.0
Molar Refractivity : 43.51
TPSA : 26.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.89
Log Po/w (XLOGP3) : 1.51
Log Po/w (WLOGP) : 2.35
Log Po/w (MLOGP) : 2.57
Log Po/w (SILICOS-IT) : 2.26
Consensus Log Po/w : 2.12

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.44
Solubility : 0.678 mg/ml ; 0.00365 mol/l
Class : Soluble
Log S (Ali) : -1.66
Solubility : 4.03 mg/ml ; 0.0216 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.28
Solubility : 0.0981 mg/ml ; 0.000527 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.13

Safety of [ 39478-78-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302+H312+H332-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 39478-78-9 ]

* 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 [ 39478-78-9 ]
  • Downstream synthetic route of [ 39478-78-9 ]

[ 39478-78-9 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 39478-78-9 ]
  • [ 56-81-5 ]
  • [ 74316-55-5 ]
Reference: [1] Yakugaku Zasshi, 1928, vol. 48, p. 74[2] Chem. Zentralbl., 1928, vol. 99, # II, p. 53
[3] Patent: WO2011/67272, 2011, A1, . Location in patent: Page/Page column 81
[4] Patent: US2012/238517, 2012, A1, . Location in patent: Page/Page column 38
[5] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 5379 - 5385
[6] Chemistry - A European Journal, 2016, vol. 22, # 32, p. 11165 - 11169
[7] Organic Letters, 2017, vol. 19, # 8, p. 2086 - 2089
  • 2
  • [ 39478-78-9 ]
  • [ 51436-99-8 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
  • 3
  • [ 39478-78-9 ]
  • [ 31543-75-6 ]
Reference: [1] Chemische Berichte, 1880, vol. 13, p. 963[2] Chemische Berichte, 1881, vol. 14, p. 417
[3] Journal of the Chemical Society, 1914, vol. 105, p. 514
[4] Chemische Berichte, 1880, vol. 13, p. 963[5] Chemische Berichte, 1881, vol. 14, p. 417
  • 4
  • [ 39478-78-9 ]
  • [ 20776-50-5 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
  • 5
  • [ 39478-78-9 ]
  • [ 36138-76-8 ]
YieldReaction ConditionsOperation in experiment
51%
Stage #1: With sulfuric acid In water at 90℃; for 4.5 h;
Stage #2: With sulfuric acid; sodium nitrite In water at 0 - 90℃; for 1 h;
5-Bromo-2-methylphenol; A solution of concentrated sulphuric acid (6 mL) in distilled water (75 mL) was added to 5-bromo-2-methylaniline (1 g, 5.38 mmol). The resultant suspension was heated to 90° C. and stirred for 4.5 h. The reaction mixture was then cooled using an ice bath and a solution of sodium nitrite (384 mg, 5.57 mmol) in water (5 mL) was added to the reaction mixture at 0° C. The reaction was then allowed to warm to ambient temperature. The reaction mixture was then added to a solution of concentrated sulphuric acid (6 mL) in water (75 mL) which had been preheated to 90° C. The reaction mixture was stirred for 1 h at 90° C. and allowed to cool, on standing, overnight. A precipitate was observed in the reaction mixture. The precipitate was collected by filtration, washed with water, and dried in a vacuum oven to afford 5-bromo-2-methylphenol as a brown solid (510 mg, 2.73 mmol, 51percent). M.S. (ESI) (m/z) 185, 187[M-H]-
51%
Stage #1: at 90℃; for 4.5 h;
Stage #2: at 0 - 90℃;
A solution of concentrated sulphuric acid (6ml_) in distilled water (75ml_) was added to 5- bromo-2-methylaniline (1g, 5.38mmol). The resultant suspension was heated to 9O0C and stirred for 4.5h. The reaction mixture was then cooled using an ice bath and a solution of sodium nitrite (384mg, 5.57mmol) in water (5ml_) was added to the reaction mixture at O0C. The reaction was then allowed to warm to ambient temperature. The reaction mixture was then added to a solution of concentrated sulphuric acid (6ml_) in water (75ml_) which had been preheated to 9O0C. The reaction mixture was stirred for 1 h at 9O0C and allowed to cool, on standing, overnight. A precipitate was observed in the reaction mixture. The precipitate was collected by filtration, washed with water, and dried in a vacuum oven to afford 5-bromo-2-methylphenol as a brown solid (510mg, 2.73mmol, 51 percent). M.S. (ESI) (m/z) 185, 187[M-H]-
Reference: [1] Patent: US2007/185156, 2007, A1, . Location in patent: Page/Page column 8-9
[2] Patent: WO2007/63071, 2007, A1, . Location in patent: Page/Page column 19
[3] Justus Liebigs Annalen der Chemie, 1913, vol. 398, p. 366
[4] Dissertation <Marburg 1912>, S. 21,
[5] Journal of the Chemical Society, 1926, p. 2038
[6] Molecules, 2011, vol. 16, # 9, p. 8053 - 8061
  • 6
  • [ 39478-78-9 ]
  • [ 350-28-7 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
  • 7
  • [ 39478-78-9 ]
  • [ 260558-15-4 ]
YieldReaction ConditionsOperation in experiment
67% at 0 - 80℃; for 0.5 h; Intermediate 64-Bromo-2-iodo-1-methylbenzene; The synthesis of Intermediates 6 is shown in Scheme 4 and full experimental details are shown below.Stage 1-4-bromo-2-iodo-1-methylbenzeneTo a solution of 2-methyl-5-bromo aniline (1.5 g, 8.06 mmol) in di-iodo methane (3.4 ml) at 0° C. was slowly added tert-butyl nitrite (1.6 ml, 12.1 mmol). The ice bath was removed and the reaction was stirred at RT then heated at 80° C. for 30 minutes. The solvent was removed under reduced pressure and the residue purified by column chromatography (EtOAc/Heptane) to afford the title compound (1.6 g, 67percent yield).LCMS: m/z 297 [M+H]+. 1H NMR (300 MHz, CDCl3) δ: 7.96 (1H, s), 7.42-7.35 (1H, m), 7.12 (1H, d, J=8.1 Hz), 2.40 (3H, s).
67% at 0 - 80℃; Stage 1- 4-bromo-2-iodo-1-methylbenzeneTo a solution of 2-methyl-5-bromo aniline (1.5 g, 8.06 mmol) in di-iodo methane (3.4 ml) at 00C was slowly added tert-butyl nitrite (1.6 ml, 12.1 mmol). The ice bath was removed and the reaction was stirred at RT then heated at 800C for 30 minutes. The solvent was removed under reduced pressure and the residue purified by column chromatography (EtOAc/ Heptane) to afford the title compound (1.6 g, 67percent yield). LCMS: m/z 297 [M+H]+. 1H NMR (300 MHz, CDCI3) δ: 7.96 (1 H, s), 7.42-7.35 (1 H, m), 7.12 (1 H, d, J=8.1 Hz), 2.40 (3H, s).
45%
Stage #1: With sulfuric acid; sodium nitrite In water at 0℃; for 0.75 h;
Stage #2: With sodium iodide In water at 20℃; for 1 h;
4-bromo-2-amino-toluene (10.0g, 53 . 7mmol) suspended in 30percent sulfuric acid (100 ml) in addition added dropwise sodium nitrite (3.89g, 56 . 4mmol) the aqueous solution (15 ml) Stirring at 0 °C for 45 minutes , then the sodium iodide (12.1g, 80 . 6mmol) dissolved in water (50 ml) in, in the aqueous solution of the above-mentioned diazonium salt solution is added. Further stirring at room temperature 1 hour, the ethyl ester of acetic acid 3 times after extraction, the saturated salt water to the acetic acid ethyl ester level to 1 times of cleaning, by means of magnesium sulfate to dry, reducing concentrated. Subsequently, by means of silica gel column purification (hexane) to obtain the target compound (9.0g, 45percent).
Reference: [1] Patent: US2011/39920, 2011, A1, . Location in patent: Page/Page column 10
[2] Patent: WO2009/130434, 2009, A1, . Location in patent: Page/Page column 21
[3] Patent: TW2016/9616, 2016, A, . Location in patent: Paragraph 0161
  • 8
  • [ 60956-26-5 ]
  • [ 39478-78-9 ]
YieldReaction ConditionsOperation in experiment
93% With stannous chloride hydrate In ethyl acetate at 30℃; First, into a 250-mL round-bottom flask, was placed 4-bromo-1-methyl-2-nitrobenzene (5 g, 23.14 mmol, 1.00 equiv), ethyl acetate (100 mL), SnCl2.H2O (20 g). The resulting solution was stirred overnight at 30° C. The pH value of the solution was adjusted to 10 with sodium hydroxide (5 mol/L). The resulting solution was extracted with 3×30 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×50 mL of brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 4 g (93percent) of 5-bromo-2-methylaniline as brown oil.
92% With iron; ammonium chloride In water for 48.5 h; Heating / reflux The mixture of iron powder (9. 31g, 167 mmol) and [NH4C1] (2.48g, 46.3 mmol) in water (50 mL) was refluxed for 30 minutes. To this hot mixture was added 4-bromo-2-nitrotoluene (10 g, 46.3 mmol) slowly and then the reaction mixture was refluxed for 48 hours. The mixture was cooled to room temperature and extracted with EtOAc (3 x 100 mL). The organic solution was washed with [H20] (3 x 200 mL) and brine (200 mL), dried (Na2SO4), and concentrated. The residue was purified by flash chromatography (silica, 15percent EtOAc in hexanes) to give 7.9g (92percent) of title compound as a pale yellow [OIL.APOS;H] nuclear magnetic resonance (NMR) [(CDC13)] : 300 MHz [6] 6.88 (m, [1H),] 6.81 (m, 2H), 3.63 (bs, 2H), 2.09 (s, 3H).
80.7% With tin(ll) chloride In ethyl acetate at 0 - 80℃; for 4.16667 h; Example 1 5-BROMO-8-METHYL-1-PROPYL-3, 4-DIHYDRO-LH-BENZOTHIENO [2, 3-CLPYRAN-1- yl] acetic acid 5-BROMO-2-METHYLANILINE [0082] 4-bromo-2-nitrotoluene (25.0 g, 0.1157 mol) in EtOAc (250 mL) was cooled to 0°C. Tin (IN chloride dihydrate (87.76 g, 0.4623 mol) was then added portionwise over 10 min while stirring. The reaction mixture was allowed to come to room temperature and then refluxed at 80°C for 4 h. The mixture was cooled to 0°C and neutralized with 5 N NAOH while stirring. EtOAc layer was filtered and remaining portions were extracted with EtOAc. The organic solution was washed with brine, dried with Na2SO4, and concentrated. The residue was purified by flash chromatography (silica, 10percent ETOAC in hexanes) to give 17. 367 g (80.7percent) of the ANILINE.
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 19, p. 3116 - 3127
[2] Patent: US2015/366198, 2015, A1, . Location in patent: Paragraph 0132
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 26, p. 6603 - 6608
[4] Patent: WO2003/99824, 2003, A1, . Location in patent: Page 23
[5] Patent: US6337351, 2002, B1, . Location in patent: Example 14
[6] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
[7] Patent: WO2005/16932, 2005, A1, . Location in patent: Page/Page column 33
[8] Journal of Chemical Research - Part S, 2000, # 6, p. 290 - 291
[9] Synlett, 1998, # 9, p. 1028 - 1028
[10] Journal of the Chemical Society. Perkin Transactions 1, 2001, # 9, p. 955 - 977
[11] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1869, vol. 69, p. 477[12] Zeitschrift fuer Chemie, 1869, p. 636
[13] Justus Liebigs Annalen der Chemie, 1870, vol. 154, p. 294
[14] Justus Liebigs Annalen der Chemie, 1871, vol. 158, p. 340
[15] Justus Liebigs Annalen der Chemie, 1873, vol. 168, p. 153[16] Justus Liebigs Annalen der Chemie, 1878, vol. 192, p. 202
[17] Collection of Czechoslovak Chemical Communications, 1935, vol. 7, p. 436,443
[18] Helvetica Chimica Acta, 1946, vol. 29, p. 872,876
[19] Patent: US2008/200471, 2008, A1, . Location in patent: Page/Page column 34
[20] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[21] Patent: WO2018/52903, 2018, A1, . Location in patent: Page/Page column 81
  • 9
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  • [ 39478-78-9 ]
Reference: [1] ACS Catalysis, 2016, vol. 6, # 12, p. 8162 - 8165
  • 10
  • [ 60956-26-5 ]
  • [ 7439-89-6 ]
  • [ 39478-78-9 ]
Reference: [1] Patent: US6300352, 2001, B1,
  • 11
  • [ 119-32-4 ]
  • [ 39478-78-9 ]
Reference: [1] Journal of Fluorine Chemistry, 2002, vol. 116, # 2, p. 173 - 179
  • 12
  • [ 39478-78-9 ]
  • [ 60710-80-7 ]
YieldReaction ConditionsOperation in experiment
75% With 2-(2-methoxyphenyl)-1-methyl-3-(diphenylphosphino)-1H-indole; potassium <i>tert</i>-butylate; triethylamine; bis(dibenzylideneacetone)-palladium(0) In dichloromethane; water; acetonitrile at 50℃; for 24 h; Inert atmosphere General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 molpercent) and ligand L4 (8.4 mg, 0.02 mmol, 2 molpercent). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuation-nitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 °C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL .x. 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 52, p. 7038 - 7041
  • 13
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  • [ 557-21-1 ]
  • [ 60710-80-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 612 - 626
  • 14
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  • [ 885681-96-9 ]
Reference: [1] Patent: TW2016/9616, 2016, A,
  • 15
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  • [ 421551-82-8 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 612 - 626
  • 16
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  • [ 79762-54-2 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 23, p. 6049 - 6053
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4458 - 4473
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 11, p. 3177 - 3180
[4] Patent: EP1622569, 2015, B1,
  • 17
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  • [ 590417-94-0 ]
Reference: [1] Patent: EP1622569, 2015, B1,
  • 18
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  • [ 937049-58-6 ]
Reference: [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 10, p. 4458 - 4473
  • 19
  • [ 39478-78-9 ]
  • [ 1351813-02-9 ]
Reference: [1] Patent: WO2017/12576, 2017, A1,
[2] Patent: WO2018/137593, 2018, A1,
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