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Chemical Structure| 6627-78-7
Chemical Structure| 6627-78-7
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Product Details of [ 6627-78-7 ]

CAS No. :6627-78-7 MDL No. :MFCD00003872
Formula : C11H9Br Boiling Point : -
Linear Structure Formula :- InChI Key :IDRVLLRKAAHOBP-UHFFFAOYSA-N
M.W : 221.09 Pubchem ID :81112
Synonyms :

Calculated chemistry of [ 6627-78-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.09
Num. rotatable bonds : 0
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 56.61
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.65 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.56
Log Po/w (XLOGP3) : 4.23
Log Po/w (WLOGP) : 3.91
Log Po/w (MLOGP) : 4.32
Log Po/w (SILICOS-IT) : 4.14
Consensus Log Po/w : 3.83

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.49
Solubility : 0.00712 mg/ml ; 0.0000322 mol/l
Class : Moderately soluble
Log S (Ali) : -3.94
Solubility : 0.0253 mg/ml ; 0.000115 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.32
Solubility : 0.00106 mg/ml ; 0.0000048 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.08

Safety of [ 6627-78-7 ]

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

Application In Synthesis of [ 6627-78-7 ]

* 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 [ 6627-78-7 ]
  • Downstream synthetic route of [ 6627-78-7 ]

[ 6627-78-7 ] Synthesis Path-Upstream   1~24

  • 1
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  • [ 3163-27-7 ]
Reference: [1] Synlett, 2003, # 5, p. 702 - 704
[2] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
  • 2
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In acetonitrile at 30 - 40℃; for 12 h; General procedure: A mixture of 1-methylnaphthalene (14, 28.44 g, 200 mmol) and NBS (39.16 g, 220 mmol) inMeCN (300 mL) was stirred at 30-40°C until completion of the reaction as indicated by TLC analysis(typically within 12 h). On cooling to room temperature, the reaction mixture was poured intoice-water (600 mL), and the resulting mixture was extracted with CH2Cl2 (500 mL × 3). The combinedextracts were washed successively with 5percent aqueous Na2S2O3 (200 mL), saturated aqueous Na2CO3(100 mL × 3) and 5percent brine (200 mL), dried (Na2SO4) and evaporated on a rotary evaporator to give aresidue, which was purified by column chromatography to afford 1-bromo-4-methylnaphthalene(15). Colorless oil, 42.01 g (98percent). 1H-NMR (DMSO-d6, 400 MHz) δ: 8.14–8.16 (m, 1H), 8.07–8.09 (m,1H), 7.76 (d, J = 7.6 Hz, 1H), 7.66–7.70 (m, 2H), 7.30 (d, J = 7.6 Hz, 1H), 2.63 (s, 3H).
90% With N-Bromosuccinimide In acetonitrile at 30 - 40℃; for 24 h; General procedure: To a stirred solution of 1-(cyclo)alkylnaphthalene (2a-2e, 0.13 mol) in MeCN (200 mL) at room temperature was added NBS (24.92 g, 0.14 mol), and the resulting mixture was stirred at 30-40°C until completion of the reaction as indicated by TLC analysis (typically within 24 h). On cooling to room temperature, the reaction mixture was poured into ice-water (800 mL), and the resulting mixture was extracted with CH2Cl2 (300 mL 3). The combined extracts were washed successively with saturated aqueous Na2CO3 (200 mL 5) and 5percent brine (500 mL), dried (Na2SO4) and evaporated on a rotary evaporator to give a residue, which was purified by column chromatography to afford the pure product 3a-3e.
88.37% With N-Bromosuccinimide In dimethyl sulfoxide at 90℃; for 10 h; 1-Methylnaphthalene (3.0 g, 21 mmol, 1.0 eq)And N-bromosuccinimide (4.1 g, 23 mmol, 1.1 eq) were added to 60 mL of dimethylsulfoxide and heated at 90 ° C for 10 hours. After completion of the TLC reaction of the starting material, the reaction was stopped. Add 60mL of purified water, 3 * 40mL ethyl acetate extraction, combine the organic layer, with 40mL saturated sodium chloride water, anhydrous magnesium sulfate, concentrated to half volume, placed in ice water bath stirring crystallization,Bromo-1-Methylnaphthalene solid4.05 g,Yield 88.37percent.
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 9, p. 2093 - 2094
[2] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 2, p. 439 - 443
[3] Molecules, 2018, vol. 23, # 2,
[4] Journal of Organic Chemistry, 2018, vol. 83, # 2, p. 930 - 938
[5] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[6] Medicinal Chemistry, 2017, vol. 13, # 3, p. 260 - 281
[7] Photochemical and Photobiological Sciences, 2016, vol. 15, # 11, p. 1385 - 1392
[8] Patent: CN105906530, 2016, A, . Location in patent: Paragraph 0080; 0081; 0082
[9] Synthetic Communications, 1997, vol. 27, # 23, p. 4159 - 4162
[10] Journal of the Chemical Society, 1927, p. 3104
[11] Chemische Berichte, 1922, vol. 55, p. 1854
[12] Chemische Berichte, 1891, vol. 24, p. 2930
[13] Chemische Berichte, 1884, vol. 17, p. 1530
[14] Chemische Berichte, 1891, vol. 24, p. 2930
[15] Chemische Berichte, 1884, vol. 17, p. 1530
[16] Journal of the American Chemical Society, 1963, vol. 85, p. 1088 - 1093
[17] Journal of Organic Chemistry, 1977, vol. 42, p. 3240 - 3243
[18] Chemistry - A European Journal, 2006, vol. 12, # 33, p. 8609 - 8613
[19] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
[20] Journal of Organic Chemistry, 2016, vol. 81, # 18, p. 8544 - 8551
[21] Patent: CN106366018, 2017, A, . Location in patent: Paragraph 0036; 0037
[22] Journal of Photochemistry and Photobiology A: Chemistry, 2016, vol. 331, p. 29 - 41
  • 3
  • [ 83-53-4 ]
  • [ 74-88-4 ]
  • [ 6627-78-7 ]
YieldReaction ConditionsOperation in experiment
73%
Stage #1: With n-butyllithium In diethyl ether; benzene at 0℃; for 1 h; Inert atmosphere
Stage #2: at 20℃;
The compounded 4' (10 mmol, 2.21 g) was added to a mixture of 30 ml of ether and 30 ml of benzene, and n-butyllithium (10 mmol, 1.6 M, 6.25 ml) was slowly added dropwise at 0°C under nitrogen atmosphere. After stirring at 0° C. for 1 hour, methyl iodide (15 mmol, 2.13 g) was slowly added dropwise to the reaction system. After completion of the dropwise addition, the reaction was warmed up to room temperature. The reaction was completed by TLC and the reaction was completed. 60 ml of a saturated aqueous solution of ammonium chloride was added to the reaction system, the aqueous layer was extracted with toluene, the organic layers were combined, washed with saturated brine (100ml*3), dried over anhydrous sodium sulfate, and the organic phase was concentrated and purified by column chromatography. Compound 4''' (7.3 mmol, 1.61 g, 73percent).
Reference: [1] Patent: CN107814795, 2018, A, . Location in patent: Paragraph 0028; 0029
  • 4
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 3163-27-7 ]
Reference: [1] Synlett, 2003, # 5, p. 702 - 704
[2] Tetrahedron Letters, 2007, vol. 48, # 18, p. 3247 - 3250
  • 5
  • [ 3163-27-7 ]
  • [ 6627-78-7 ]
  • [ 86-53-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
  • 6
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 13098-88-9 ]
  • [ 66-77-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 9, p. 2724 - 2727
  • 7
  • [ 64-19-7 ]
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
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  • [ 66-77-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1981, vol. 54, # 9, p. 2724 - 2727
  • 8
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 86-53-3 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 16, p. 4194 - 4197
  • 9
  • [ 90-11-9 ]
  • [ 6627-78-7 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 33, p. 8609 - 8613
  • 10
  • [ 75-15-0 ]
  • [ 7726-95-6 ]
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 79996-99-9 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1854
  • 11
  • [ 6627-78-7 ]
  • [ 16650-55-8 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 21, p. 4549 - 4552
[2] Journal of Fluorine Chemistry, 1988, vol. 38, p. 139 - 152
[3] Archiv der Pharmazie, 2008, vol. 341, # 10, p. 547 - 609
[4] Chemische Berichte, 1922, vol. 55, p. 1854
[5] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
  • 12
  • [ 6627-78-7 ]
  • [ 7697-37-2 ]
  • [ 16650-55-8 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1854
  • 13
  • [ 6627-78-7 ]
  • [ 556-63-8 ]
  • [ 4488-40-8 ]
Reference: [1] Synthesis, 2006, # 18, p. 3106 - 3110
  • 14
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  • [ 4488-40-8 ]
Reference: [1] Journal of the American Chemical Society, 1993, vol. 115, # 6, p. 2180 - 2190
  • 15
  • [ 6627-78-7 ]
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YieldReaction ConditionsOperation in experiment
77.43% With tetrabutylammomium bromide In ethyl acetate at 70℃; for 9 h; Weigh 4-Bromo-1-methylnaphthalene3.3 g (10.2 mmol, 1.5 eq) of tetrabutylammonium bromide was added to 30 mL of ethyl acetate and the mixture was refluxed at 70 ° C for 9 hours. After TLC showed that the starting material was completely reacted, The reaction was stopped. After filtering, the filter cake was stirred at room temperature for 2 hours with 30 mL of ethyl acetate and filtered to give 1.60 g of 1-bromo-4- (bromomethyl) naphthalene as a pale yellow solid in a yield of 77.43percent.
73% With N-Bromosuccinimide; dibenzoyl peroxide In hexane for 36 h; Reflux; Inert atmosphere A suspension of 11 (35.37 g, 160 mmol), BPO (0.78 g, 3.2 mmol), and NBS (34.17 g, 192 mmol) in n-hexane (400 mL) was refluxed under N2 until the completion of reaction as indicated by TLC analysis (typically 36 h; once the reaction commenced, 0.78 g of BPO was added every 8 h until the reaction completed). The reaction mixture was cooled to room temperature while stirring, and the precipitates were collected via vacuum filtration. The precipitates were triturated successively with saturated aqueous NaHCO3 (500 mL x 2), water (800 mL x 2), and n-hexane (800 mL) to give rise to (4-bromonaphth-1-yl)methyl bromide 12. White solid; 35.04 g (73percent); m.p. 104.5–106 °C (literature value, 102–104 °C [44]). 1H-NMR (DMSO-d6, 400 MHz) δ: 8.20–8.26 (m, 2H), 7.85 (d, J = 7.6 Hz, 1H), 7.71–7.77 (m, 2H), 7.62 (d, J = 7.6 Hz, 1H), 5.21 (s, 2H).
500 g With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane at 70 - 78℃; A 5 L four-necked flask was charged with 461.8 g of 4-bromo-1-methylnaphthalene (I)7.2kg of carbon tetrachloride,375.6 g of N-bromosuccinimide,20.5 g BP0,The temperature was raised to 70 to 78 ° C (preferably 77 ° C) and the reaction was refluxed overnight.Point plate,The reaction is complete.Cooled to room temperature,Filter,40 ° C spin dry solvent.Add 1200 g of ethanol,Heating up to 70 ° C Paul lh,Cooling to room temperature,Filter,Filter cake washed with ethanol,After draining,Dried at 35 ° C to give 500 g of 4-bromo-1-bromomethylnaphthalene (II)The two-step yield was 79percent (based on 1-methylnaphthalene).
Reference: [1] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[2] Journal of Organic Chemistry, 1999, vol. 64, # 4, p. 1387 - 1390
[3] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[4] Patent: CN105906530, 2016, A, . Location in patent: Paragraph 0091; 0092; 0093; 0094; 0095
[5] Organic Letters, 2008, vol. 10, # 14, p. 3105 - 3108
[6] Molecules, 2016, vol. 21, # 11,
[7] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
[8] MedChemComm, 2016, vol. 7, # 5, p. 900 - 905
[9] Angewandte Chemie - International Edition, 2006, vol. 45, # 32, p. 5311 - 5315
[10] Journal of the Chemical Society, 1927, p. 3104
[11] Journal of the American Chemical Society, 1954, vol. 76, p. 604
[12] Dyes and Pigments, 2011, vol. 88, # 1, p. 57 - 64
[13] Chemical Communications, 2016, vol. 52, # 9, p. 1949 - 1952
[14] Patent: CN106366018, 2017, A, . Location in patent: Paragraph 0038; 0039
[15] Patent: WO2017/147328, 2017, A1, . Location in patent: Paragraph 0377
[16] Patent: WO2010/79077, 2010, A1, . Location in patent: Page/Page column 34
  • 16
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  • [ 7726-95-6 ]
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Reference: [1] Journal of the Chemical Society, 1927, p. 3104
  • 17
  • [ 75-15-0 ]
  • [ 7726-95-6 ]
  • [ 90-12-0 ]
  • [ 6627-78-7 ]
  • [ 79996-99-9 ]
Reference: [1] Chemische Berichte, 1922, vol. 55, p. 1854
  • 18
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  • [ 4523-45-9 ]
Reference: [1] Journal of the Chemical Society, 1965, p. 5948 - 5953
[2] Organic Letters, 2017, vol. 19, # 16, p. 4279 - 4282
  • 19
  • [ 6627-78-7 ]
  • [ 50672-84-9 ]
YieldReaction ConditionsOperation in experiment
15% at 80℃; for 4 h; 1-Bromo-4-methylnaphthalene (1.06 g, 4.79 mmol) was dissolved in a 50percent acetic acid aqueous solution (100 ml). Diammonium cerium nitrate (7.61 g, 13.9 mmol) was added, and the mixture was stirred at 80°C for four hours. The reaction solution was cooled to room temperature and then water (300 mL) was added, followed by extraction with ethyl acetate (300 mL). The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (elution solvent: hexane/ethyl acetate = 10/1) to give the target compound (173 mg, yield: 15percent) as a light yellow solid. 1H-NMR (CDCl3, 400MHz):δ ppm: 7.69-7.78 (2H, m), 7.82 (1H, d, J=7.8Hz), 7.99 (1H,d,J=7.8Hz),8.38(1H,d,J=8.4Hz),9.29(1H,d,J=8.4Hz),10.38(1H,s). MS (EI) m/z: 233.9679 (M+)
Reference: [1] Patent: EP1914229, 2008, A1, . Location in patent: Page/Page column 88
[2] European Journal of Organic Chemistry, 2006, # 10, p. 2329 - 2335
[3] Inorganic Chemistry, 2016, vol. 55, # 5, p. 1986 - 1991
[4] Patent: CN106366018, 2017, A,
[5] Patent: WO2010/79077, 2010, A1,
  • 20
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Reference: [1] European Journal of Organic Chemistry, 2014, vol. 2014, # 19, p. 4115 - 4122
[2] Patent: CN106366018, 2017, A,
  • 21
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YieldReaction ConditionsOperation in experiment
95%
Stage #1: With n-butyllithium In diethyl ether; hexane at -78 - 20℃;
Stage #2: at -78 - 20℃; for 15.5 h;
Stage #3: With hydrogenchloride In diethyl ether; hexane; water
3.4. 4-Methyl-1-naphthylboronic acid 4 A solution of n-BuLi (1.7 M in hexane, 10 mL) was slowly added to a cooled (-78 °C) solution of 1-bromo-4-methyl naphthalene (1.5 g, 6.78 mmol) in dry ether (200 mL). The mixture was then allowed to warm up and stirred at room temperature for 2 h. It was then cooled back (-78 °C) and a solution of tri-iso-propyl borate (4 g, 4.91 mL, 21.27 mmol) in ether (20 mL) was rapidly added. The mixture was stirred at -78 °C for 30 min and then at room temperature for 15 h. Then, 100 mL of HCl (2 M) was added and milky white emulsion gradually became clear. The ethereal layer was then separated and the aqueous layer was extracted with ether (3≍100 mL). The combined ether solutions were dried (MgSO4) and the solvent was rotoevaporated. The residual solid was recrystallized from hot CH2Cl2 to give white solid. Yield: 95percent; 1H (300 MHz, CD2Cl2): δ 9.33 (d, J=9.3 Hz, 1H), 8.59 (d, J=7.0 Hz 1H), 8.16 (d, J=9.5 Hz, 1H), 7.65 (dd, 2H), 7.54 (d, J=7.6 Hz, 1H), 2.82 (s, 3H); 13C (75 MHz, CD2Cl2): δ 140.3, 137.5, 132.8, 132.3, 128.6, 126.5, 126.3, 125.9, 125.7, 124.6, 19.5; MS (CI, CH4): m/z calcd for C11H11BO2: 186.1; found 186.1 [M+]. Anal. Calcd for C11H11BO2·H2O: C, 64.75; H, 6.42. Found: C, 62.91; H, 5.64. 13
78%
Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 2 h; Inert atmosphere
Stage #2: at 20℃;
In a 100 ml three-necked flask, compound 4''' (10 mmol, 2.48 g) and THF (50 ml) were added, and n-butyllithium (11 mmol, 1.6 M, 6.88 ml) was slowly added dropwise under nitrogen atmosphere at -78°C. The reaction was carried out at -78°C for 2 hours, and then 5 ml of a THF solution of triisopropyl borate (15 mmol, 3.03 g) was slowly added dropwise to the reaction system. After the addition was completed, the mixture was slowly warmed to room temperature and stirred overnight. After the disappearance of the TLC test material, the reaction was completed. reaction. The mixture was quenched with dilute hydrochloric acid (20percent, 20 ml), stirred at room temperature for 3 hours, then extracted with ethyl acetate (50 ml*3), and the combined organic phases were washed with saturated brine (100 ml*3) and dried over anhydrous sodium sulfate. The organic phase was concentrated and purified by column chromatography to give compound 3''' (7.8 mmol, 1.45 g, 78percent).
Reference: [1] Tetrahedron, 2012, vol. 68, # 46, p. 9371 - 9375,5
[2] Tetrahedron,
[3] Patent: CN107814795, 2018, A, . Location in patent: Paragraph 0028; 0030
[4] Patent: CN107973777, 2018, A, . Location in patent: Paragraph 0042; 0045; 0046
[5] Patent: CN108129453, 2018, A, . Location in patent: Paragraph 0041; 0042; 0045; 0046
[6] Patent: CN108191821, 2018, A, . Location in patent: Paragraph 0042; 0045; 0046
[7] Patent: CN108129450, 2018, A, . Location in patent: Paragraph 0044; 0045; 0048-0049; 0058-0059
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Reference: [1] Patent: US2001/49379, 2001, A1,
  • 23
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  • [ 103986-53-4 ]
Reference: [1] Chemistry - A European Journal, 2006, vol. 12, # 33, p. 8609 - 8613
  • 24
  • [ 688-74-4 ]
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  • [ 103986-53-4 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1957, vol. 11, p. 1075
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