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[ CAS No. 36138-76-8 ] {[proInfo.proName]}

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Chemical Structure| 36138-76-8
Chemical Structure| 36138-76-8
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Product Details of [ 36138-76-8 ]

CAS No. :36138-76-8 MDL No. :MFCD08061906
Formula : C7H7BrO Boiling Point : -
Linear Structure Formula :- InChI Key :OONJCAWRVJDVBB-UHFFFAOYSA-N
M.W : 187.03 Pubchem ID :12648404
Synonyms :

Calculated chemistry of [ 36138-76-8 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 41.13
TPSA : 20.23 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) : -5.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.96
Log Po/w (XLOGP3) : 2.69
Log Po/w (WLOGP) : 2.46
Log Po/w (MLOGP) : 2.57
Log Po/w (SILICOS-IT) : 2.5
Consensus Log Po/w : 2.44

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.19
Solubility : 0.121 mg/ml ; 0.000649 mol/l
Class : Soluble
Log S (Ali) : -2.77
Solubility : 0.32 mg/ml ; 0.00171 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.06
Solubility : 0.162 mg/ml ; 0.000865 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.11

Safety of [ 36138-76-8 ]

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

Application In Synthesis of [ 36138-76-8 ]

* 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 [ 36138-76-8 ]
  • Downstream synthetic route of [ 36138-76-8 ]

[ 36138-76-8 ] Synthesis Path-Upstream   1~10

  • 1
  • [ 5532-69-4 ]
  • [ 7732-18-5 ]
  • [ 67-64-1 ]
  • [ 36138-76-8 ]
  • [ 2316-64-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1898, vol. 302, p. 145
  • 2
  • [ 36138-76-8 ]
  • [ 7151-68-0 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 1285,1287
[2] Acta Chemica Scandinavica (1947-1973), 1952, vol. 6, p. 1137,1400
  • 3
  • [ 95-48-7 ]
  • [ 7766-23-6 ]
  • [ 36138-76-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1981, p. 32 - 41
  • 4
  • [ 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
  • 5
  • [ 2835-95-2 ]
  • [ 36138-76-8 ]
YieldReaction ConditionsOperation in experiment
26%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃; for 0.5 h;
Stage #2: With hydrogen bromide; copper(I) bromide In water at 0℃; for 2 h; Heating / reflux
To a solution of 5-AMINO-2-METHYLPHENOL (10 G, 81.2 MMOL) in hydrobromic acid (40 mL, 48 percent solution) and water (50 mL) at 0 °C was added a solution of sodium nitrite (5.6 g, 81.2 MMOL) in water (15 mL) and the mixture stirred at this temperature for 30 minutes. To this was added copper (I) bromide (11.6 G, 81. 2 MMOL) in hydrobromic acid (15 mL, 48percent solution) and the reaction was subsequently heated at reflux for 2 hours. Upon cooling to room temperature the resulting mixture was extracted with ethyl acetate (2 x 200 mL) and the combined organic extracts were washed with aqueous potassium hydroxide solution (-1 M, 200 mL), dried (magnesium sulphate) and concentrated under reduced pressure. The crude product was purified by column chromatography [SI02 ; light petroleum to 4: 1 light petroleum-ethyl acetate] to give the title compound as a COLOURLESS OIL, WHICH CRYSTALLISED to give fine colourless needles upon standing overnight (4 G, 26 percent). Rf = 0.26 [4: 1 light petroleum-ethyl acetate]. 1H NMR 5 2.21 (3 H, s), 4.89-4. 95 (1 H, br, s), 6.96-6. 97 (1 H, br, m), 6.99-7. 00 (2 H, m).
24%
Stage #1: With hydrogen bromide; sodium nitrite In water at 0 - 10℃; for 0.25 h;
Stage #2: With copper(I) bromide In water at 10 - 80℃; for 0.5 h;
To a solution of 5-amino-2-methylphenol (50 g, 0.41 mol) in hydrobromic acid (200 mL, 48 percent solution) and water (200 ml) in a brine ice bath was added sodium nitrite (30.5 g, 0.45 mol, 1.1 equiv.) portion-wise at such a rate that the temperature remained below +10 °C, and the mixture was stirred for a EPO <DP n="68"/>further 15 minutes. To this solution was added copper(l) bromide (64 g, 0.44 mol, 1.1 equiv.) and the reaction was subsequently heated to 80 0C. Effervescence was observed at 60-65 °C indicating that the reaction had occurred. The mixture was heated at 80 °C for a further 30 minutes and then allowed to cool to room temperature. The resulting black tarry mixture was extracted with petroleum ether 40-60 0C (4 x 400 ml) and the combined organic extracts were dried (MgSO4) and concentrated under reduced pressure. [Note that a large tarry component does not dissolve in either petrol or the aqueous layer and sometimes the petrol layer was simply decanted from this once all the aqueous layer had been run out from the separating funnel]. The resulting orange-white solid was recrystallised from petrol to give the product as a white solid (13 g 17 percent). The mother liquors were further purified by dry flash column chromatography (particle size 3-35 A), eluting with 0-20percent diethyl ether in petroleum ether 40-60 0C to give a yellow-white crystalline solid which was re-crystallised from petroleum ether 40-60 °C to give a further 5 g and an overall yield of 18 g (24 percent); Rf = 0.26 (4:1 petrol- ethyl acetate), m.p. 77-78 °C (from petrol). 1H NMR δH 2.21 (3 H, s), 4.89- 4.95 (1 H, br, s), 6.96-6.97 (1 H, br, m) and 6.99-7.00 (2 H, m).
20%
Stage #1: With hydrogen bromide In water at 0℃; for 0.0833333 h;
Stage #2: With sodium nitrite In water at 0℃; for 0.5 h;
Stage #3: With copper(I) bromide In water at 0℃; for 2 h; Heating / reflux
Example 60; Synthesis of 4-(4-methyl-3-(5-(trifluoromethyl)pyridin-2-yloxy)benzylidene)-N-(pyridin-3-yl)piperidine-1-carboxamide; Step 1; 5-Bromo-2-methylphenol; 5-Amino-2-methylphenol (5 g, 0.04 mol) was dissolved in HBr (20 mL) and H2O (20 mL) was added dropwise maintaining a temperature below 0° C. The resulting mixture was stirred for 5 min and a solution of NaNO2 (2.76 g, 0.04 mol) in H2O (7.5 mL) was added dropwise. The mixture was stirred for 30 min below 0° C. Then a solution of cuprous bromide (5.73 g, 0.04 mol) in HBr (7.5 mL) cooled to 0° C. was added dropwise. The resulting mixture was warmed to RT and then refluxed for 2 h. The reaction was cooled and filtered through celite. The filtrate was diluted with water and extracted with EtOAc. The organic extract was dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by column chromatography (2.5percent EtOAc-97.5percent Hexane) to give the pure title compound (1.57 g, 20percent). 1H NMR (500 MHz, CDCl3): δ 6.97 (s, 3H), 4.89 (s, 1H), 2.19 (s, 3H).
Reference: [1] Patent: WO2005/5442, 2005, A1, . Location in patent: Page 22; 28
[2] Patent: WO2007/582, 2007, A1, . Location in patent: Page/Page column 66-67
[3] Patent: US2008/261941, 2008, A1, . Location in patent: Page/Page column 39
  • 6
  • [ 95-48-7 ]
  • [ 7766-23-6 ]
  • [ 36138-76-8 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999), 1981, p. 32 - 41
  • 7
  • [ 5532-69-4 ]
  • [ 7732-18-5 ]
  • [ 67-64-1 ]
  • [ 36138-76-8 ]
  • [ 2316-64-5 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1898, vol. 302, p. 145
  • 8
  • [ 36138-76-8 ]
  • [ 74-88-4 ]
  • [ 67868-73-9 ]
Reference: [1] Synlett, 2013, vol. 24, # 2, p. 157 - 160
[2] Molecules, 2011, vol. 16, # 9, p. 8053 - 8061
[3] Patent: WO2014/99503, 2014, A1, . Location in patent: Paragraph 00112
  • 9
  • [ 36138-76-8 ]
  • [ 77-78-1 ]
  • [ 67868-73-9 ]
Reference: [1] Journal of the Chemical Society, 1953, p. 1285,1287
[2] Acta Chemica Scandinavica (1947-1973), 1952, vol. 6, p. 1137,1400
[3] Angewandte Chemie - International Edition, 2018, vol. 57, # 9, p. 2450 - 2454[4] Angew. Chem., 2018, vol. 130, # 9, p. 2475 - 2479,5
  • 10
  • [ 36138-76-8 ]
  • [ 858523-37-2 ]
Reference: [1] Patent: WO2014/99503, 2014, A1,
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