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Chemical Structure| 27060-75-9
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Product Details of [ 27060-75-9 ]

CAS No. :27060-75-9 MDL No. :MFCD00060687
Formula : C8H9BrO Boiling Point : -
Linear Structure Formula :- InChI Key :BLZNSXFQRKVFRP-UHFFFAOYSA-N
M.W : 201.06 Pubchem ID :117915
Synonyms :

Calculated chemistry of [ 27060-75-9 ]

Physicochemical Properties

Num. heavy atoms : 10
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 45.6
TPSA : 9.23 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) : -5.27 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 3.18
Log Po/w (WLOGP) : 2.77
Log Po/w (MLOGP) : 2.88
Log Po/w (SILICOS-IT) : 2.96
Consensus Log Po/w : 2.85

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.47
Solubility : 0.0684 mg/ml ; 0.00034 mol/l
Class : Soluble
Log S (Ali) : -3.04
Solubility : 0.181 mg/ml ; 0.000902 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.77
Solubility : 0.0342 mg/ml ; 0.00017 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.18

Safety of [ 27060-75-9 ]

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 [ 27060-75-9 ]

* 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 [ 27060-75-9 ]
  • Downstream synthetic route of [ 27060-75-9 ]

[ 27060-75-9 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 27060-75-9 ]
  • [ 102-50-1 ]
Reference: [1] Organic Letters, 2014, vol. 16, # 17, p. 4388 - 4391
[2] Journal of Organic Chemistry, 2009, vol. 74, # 12, p. 4542 - 4546
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  • [ 14472-14-1 ]
Reference: [1] Australian Journal of Chemistry, 1972, vol. 25, p. 1719 - 1729
  • 3
  • [ 27060-75-9 ]
  • [ 19614-12-1 ]
YieldReaction ConditionsOperation in experiment
78% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane at 80℃; for 18 h; To a CCl4 solution (125 mL) of 2-bromo-5-methoxytoluene (0.050 mol) and NBS (0.055 mol) was added AIBN (0.001 mol), and the mixture was stirred at 80 °C for 18 h. The mixture was diluted with hexane before filtration through a Celite pad. Evaporation of the solvent followed by washing of the residue with ethyl acetate gave 4-bromo-3-(bromomethyl)anisole.
72% With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane a
4-Bromo-3-bromomethylanisole
To a stirred solution of 4-bromo-3-methylanisole (100 g, 497 mmol) in dry dichloromethane (500 mL) was added N-bromosuccinimide (97 g, 545 mmol) followed by benzoyl peroxide (6 g, 25 mmol).
The reaction was gently refluxed with a 150 watt flood lamp with reflector placed approximately 12 inches from the reaction flask.
After 24 h the reaction was concentrated by rotary evaporation to half its volume and allowed to sit for 4 h.
The white precipitate which formed was filtered off and rinsed with a small volume of dichloromethane.
The filtrate was concentrated to dryness and the remaining solid was triturated with hexanes and filtered.
Drying under vacuum gave the title compound (100.25 g, 72percent) as white needles: GC tR=6.56 min (HP 530 Jm*20 m methylsilicone column, He carrier flow 20 mL/min, 100° C. initial temp., 1 min initial time, 10° C./min rate, 200° C. final temp., 1 min final time); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=10 Hz, 1H), 6.99 (d, J=3 Hz, 1H), 6.73 (dd, 1H), 4.55 (s, 2H), 3.80 (s, 3H).
72% With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane a
4-Bromo-3-bromomethylanisole
To a stirred solution of 4-bromo-3-methylanisole (100 g, 497 mmol) in dry dichloromethane (500 mL) was added N-bromosuccinimide (97 g, 545 mmol) followed by benzoyl peroxide (6 g, 25 mmol).
The reaction was gently refluxed with a 150 watt flood lamp with reflector placed approximately 12 inches from the reaction flask.
After 24 h the reaction was concentrated by rotary evaporation to half its volume and allowed to sit for 4 h.
The white precipitate which formed was filtered off and rinsed with a small volume of dichloromethane.
The filtrate was concentrated to dryness and the remaining solid was triturated with hexanes and filtered.
Drying under vacuum gave the title compound (100.25 g, 72percent) as white needles: GC tR=6.56 min (HP 530 μm*20 m methylsilicone column, He carrier flow 20 mL/min, 100° C. initial temp., 1 min initial time, 10° C./min rate, 200° C. final temp., 1 min final time); 1H NMR (400 MHz, CDCl3) δ 7.44 (d, J=10 Hz, 1H), 6.99 (d, J=3 Hz, 1H), 6.73 (dd, 1H), 4.55 (s, 2H), 3.80 (s, 3H).
72% With N-Bromosuccinimide; dibenzoyl peroxide In dichloromethane a
4-Bromo-3-bromomethylanisole
To a stirred solution of 4-bromo-3-methylanisole (100 g, 497 mmol) in dry dichloromethane (500 mL) was added N-bromosuccinimide (97 g, 545 mmol) followed by benzoyl peroxide (6 g, 25 mmol).
The reaction was gently refluxed with a 150 watt flood lamp with reflector placed approximately 12 inches from the reaction flask.
After 24 h the reaction was concentrated by rotary evaporation to half its volume and allowed to sit for 4 h.
The white precipitate which formed was filtered off and rinsed with a small volume of dichloromethane.
The filtrate was concentrated to dryness and the remaining solid was triturated with hexanes and filtered.
Drying under vacuum gave the title compound (100.25 g, 72percent) as white needles: GC tR=6.56 min (HP 530 μm*20 m metbylsilicone column, He carrier flow 20 mL/min, 100° C. initial temp., 1 min initial time, 10° C./min rate, 200° C. final temp., 1 min final time); 1 H NMR (400 MHz, CDCl3) δ7.44 (d, J=10 Hz, 1 H), 6.99 (d, J=3 Hz, 1 H), 6.73 (dd, 1 H), 4.55 (s, 2 H), 3.80 (s, 3 H).
65% With N-Bromosuccinimide; 4-(benzoyloxy)benzoic acid In tetrachloromethane at 20℃; for 16 h; Reflux l-Bromo-2-(bromomethyl)-4-methoxybenzeneTo a solution of 173 g (0.86 mol) of l-bromo-4-methoxy-2-methylbenzene in 850 ml of CCI4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature. This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2). The precipitate was additionally washed by 2 x 150 ml of CC14. The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane. The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum. This procedure gave 121 g of the title product. Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n- hexane at -25°C. In total, 157 g (65percent; or 56percent overall yield for two stages) of 1- bromo-2-(bromomethyl)-4-methoxybenzene has been isolated.Anal. calc. for C8H8Br20: C, 34.32; H, 2.88. Found: C, 34.44; H, 2.95.
56% With N-Bromosuccinimide In tetrachloromethane; hexane 1-Bromo-2-(bromomethyl)-4-methoxybenzene
To a solution of 173 g (0.86 mol) of 1-bromo-4-methoxy-2-methylbenzene in 850 ml of CCl4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature.
This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2).
The precipitate was additionally washed by 2 x 150 ml of CCl4.
The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane.
The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum.
This procedure gave 121 g of the title product.
Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n-hexane at -25°C. In total, 157 g (65percent; or 56percent overall yield for two stages) of 1-bromo-2-(bromomethyl)-4-methoxybenzene has been isolated.
Anal. calc. for C8H8Br2O : C, 34.32; H, 2.88. Found: C, 34.44; H, 2.95.
56% With N-Bromosuccinimide In hexane 1-Bromo-2-(bromomethyl)-4-methoxybenzene
To a solution of 173 g (0.86 mol) of 1-bromo-4-methoxy-2-methylbenzene in 850 ml of CCl4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature.
This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2).
The precipitate was additionally washed by 2*150 ml of CCl4.
The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane.
The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum.
This procedure gave 121 g of the title product.
Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n-hexane at -25° C. In total, 157 g (65percent; or 56percent overall yield for two stages) of 1-bromo-2-(bromomethyl)-4-methoxybenzene has been isolated.
Anal. calc. for C8H8Br2O: C, 34.32; H, 2.88. Found: C, 34.44; H, 2.95.
50% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 18 h; Inert atmosphere; Reflux A dry, stir bar-equipped, 3-neck 250 mL round bottom flask was fitted with a reflux condenser and put under nitrogen. 77 1-bromo-4-methoxy-2-methylbenzene (1.39 mL, 2.011 g, 10.0 mmol, 1.00 eq), 121 CCl4 (20.0 mL, 0.50 Molar, not degassed), 122 N-bromosuccinimide (recrystallized, 2.67 g, 15.0 mmol, 1.50 eq), and 123 benzoyl peroxide (0.121 g, 0.50 mmol, 5 mol percent) were added by briefly removing a septum while under positive nitrogen pressure. The reaction was heated to reflux for 18 hours. (0187) The next day, the reaction was filtered through a silica gel plug, rinsing with 10/1 Hex/Et2O. The crude product was purified by normal phase column chromatography (5 cm diameter, 300 mL silica gel, isocratic 4/1 Hex/DCM), giving SI-3 as a fluffy, slightly off-white powder (1.404 g, 5.015 mmol, 50percent yield). (0188) 1H NMR (500 MHz, CDCl3) δ 7.45 (d, J=8.8 Hz, 1H), 6.99 (d, J=3.0 Hz, 1H), 6.74 (dd, J=8.8, 3.0 Hz, 1H), 4.56 (s, 2H), 3.80 (s, 3H). 13C NMR (126 MHz, CDCl3) δ 159.28, 137.90, 134.06, 116.67, 116.27, 114.85, 55.71, 33.61. HRMS (EI+) Calculated for C8H8OBr2: 277.89422; Found: 277.89402.
21% With N-Bromosuccinimide In tetrachloromethane for 7 h; Reflux Into a 1000-mL round-bottom flask, was placed a solution of l-bromo-4-methoxy- 2-methylbenzene (20 g, 100.00 mmol, 1.00 equiv) in CCI4 (200 mL). Then NBS (19.58 g, 110.00 mmol, 1.10 equiv) and BPO (1.21 g, 5.00 mmol, 0.05 equiv) were added. The resulting solution was heated to reflux for 7 hs in an oil bath. The resulting solids were filtered out. The filtrate was concentrated under vacuum and applied onto a silica gel column with ethyl acetate/petroleum ether (1:500). This resulted in 5.9 g (21percent) of l-bromo-2-(bromomethyl)-4-methoxybenzene as a light yellow solid.

Reference: [1] Tetrahedron, 2004, vol. 60, # 49, p. 11075 - 11087
[2] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10124 - 10125
[3] Journal of Organic Chemistry, 2014, vol. 79, # 11, p. 4973 - 4983
[4] Synlett, 2011, # 17, p. 2525 - 2528
[5] Journal of Medicinal Chemistry, 2000, vol. 43, # 1, p. 22 - 26
[6] Chemistry Letters, 2011, vol. 40, # 11, p. 1272 - 1274
[7] Patent: US2003/125317, 2003, A1,
[8] Patent: US2003/125317, 2003, A1,
[9] Patent: US2001/14737, 2001, A1,
[10] Organic Letters, 2010, vol. 12, # 5, p. 940 - 943
[11] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 18, p. 2747 - 2755
[12] Patent: WO2013/7650, 2013, A1, . Location in patent: Page/Page column 79; 80
[13] Patent: EP2746301, 2014, A1, . Location in patent: Page/Page column
[14] Patent: US2015/344596, 2015, A1,
[15] Patent: US2018/305381, 2018, A1, . Location in patent: Paragraph 0112; 0186-0188
[16] Organic Letters, 2015, vol. 17, # 19, p. 4654 - 4657
[17] Patent: WO2011/28947, 2011, A2, . Location in patent: Page/Page column 176-177
[18] Journal of the American Chemical Society, 1968, vol. 90, p. 4051 - 4055
[19] Synthetic Communications, 1984, vol. 14, # 13, p. 1205 - 1212
[20] Journal fuer Praktische Chemie - Practical Applications and Applied Chemistry (Germany), 2000, vol. 342, # 2, p. 162 - 168
[21] Journal of Medicinal Chemistry, 2007, vol. 50, # 4, p. 848 - 855
[22] Synlett, 2009, # 11, p. 1852 - 1858
[23] European Journal of Organic Chemistry, 2010, # 35, p. 6760 - 6778
[24] Angewandte Chemie - International Edition, 2012, vol. 51, # 16, p. 3826 - 3831
[25] Chemistry - A European Journal, 2012, vol. 18, # 16, p. 4859 - 4865
[26] Chemistry - A European Journal, 2013, vol. 19, # 27, p. 9050 - 9058
  • 4
  • [ 77-48-5 ]
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  • [ 19614-12-1 ]
YieldReaction ConditionsOperation in experiment
61.1% With 2,2'-azobis(isobutyronitrile) In chlorobenzene at 70℃; for 3 h; 1-2)
2-Bromo-5-methoxybenzyl bromide
azobisisobutyronitrile (0.60 g) was added to a mixture of 2-bromo-5-methoxytoluene (77.38 g, 384 mmol), 5,5-dimethy-1,3-dibromohydantoin (57.5 g, 200 mmol) and chlorobenzene (1500 ML), followed by stirring at 70°C for 2 hours..
azobisisobutyronitrile (0.60 g) was added thereto again and stirred for another 1 hour..
A 10percent aqueous sodium thiosulfate solution (500 ML) was added to the reaction mixture, and the organic layer was washed with a saturated aqueous sodium chloride solution..
The organic layer washed was dried over anhydrous magnesium sulfate and then concentrated to dryness to obtain a crude product of 2-bromo-5-methoxybenzyl bromide..
Thereto was added 100 ML of ice-cooled hexane to obtain a homogeneous slurry, which was filtered..
The residue was washed with 100 ML of ice-cooled hexane and then dried under reduced pressure to obtain 65.75 g (235 mmol, 61.1percent) of 2-bromo-5-methoxybenzyl bromide. NMR (CDCl3) δ 3.79 (s, 3H), 4.55 (s, 2H), 6.73 (dd, 1H, J = 3.0, 8.9 Hz), 6.99 (d, 1H, J = 3.0 Hz), 7.40 (d, 1H, J = 8.9 Hz).
Reference: [1] Patent: EP1466901, 2004, A1, . Location in patent: Page 25
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Reference: [1] Patent: US2003/191126, 2003, A1,
  • 6
  • [ 557-21-1 ]
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  • [ 21883-13-6 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 2, p. 202 - 205
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  • [ 557-21-1 ]
  • [ 21883-13-6 ]
Reference: [1] Synlett, 2003, # 14, p. 2237 - 2239
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  • [ 7507-86-0 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10124 - 10125
[2] Journal of Organic Chemistry, 2004, vol. 69, # 6, p. 2084 - 2093
[3] European Journal of Organic Chemistry, 2010, # 35, p. 6760 - 6778
  • 9
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  • [ 182500-28-3 ]
Reference: [1] Patent: WO2017/176812, 2017, A1,
  • 10
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  • [ 89978-56-3 ]
YieldReaction ConditionsOperation in experiment
39% With bismuth (III) nitrate pentahydrate In 1,2-dichloro-ethane at 80℃; To a suspension 151 (2.5 g, 12.5 mmoi) in DCE (20 mL) is added bismuth nitrate pentahydrate (7.28 g, 15 mmol) at room temperature. After stirring at 80 °C overnight, the mixture is cooled to room temperature, filtered, concentrated, and purified by silica gelcolumn chromatography (EA:PE 1:10) to give 152 as a light yellow solid (119 g, 39percent yield). (MS: [M+Hi 2460)
27% With nitric acid; acetic acid; trifluoroacetic acid In acetic acid at -5℃; for 2 h; 136.2
1-Bromo-4-methoxy-2-methyl-5-nitro-benzene
1-Bromo-4-methoxy-2-methylbenzene obtained in step 136.1 (60 g, 298 mmol) was dissolved in acetic acid (150 ml) and TFA (150 ml).
The mixture was cooled to -5° C. in an ice bath.
Fuming nitric acid (14.56 ml, 328 mmol) was added slowly to the reaction.
The resulting mixture was stirred at -5° C. for about 2 h.
The reaction mixture was diluted with water (100 ml).
The aqueous layer was extracted with ethyl acetate (3*100 mL) and washed with sat. NaCl (100 mL), sat. NaHCO3 (100 mL) and sat. NaCl (100 mL).
The organic layer was dried with Na2SO4, filtered and concentrated.
The resulting solid was purified with silica gel column chromatography (hexane/EtOAc=50:1).
The proper fractions were collected and concentrated to give the title compound (20 g, 27percent).
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 12, p. 2768 - 2774
[2] Patent: WO2017/176812, 2017, A1, . Location in patent: Paragraph 0416
[3] Patent: US2013/116229, 2013, A1, . Location in patent: Paragraph 1011
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  • [ 89978-56-3 ]
  • [ 85598-13-6 ]
Reference: [1] Journal of Heterocyclic Chemistry, 2011, vol. 48, # 1, p. 209 - 214
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  • [ 150192-39-5 ]
Reference: [1] Journal of the American Chemical Society, 2005, vol. 127, # 29, p. 10124 - 10125
[2] European Journal of Organic Chemistry, 2010, # 35, p. 6760 - 6778
  • 13
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  • [ 75534-35-9 ]
Reference: [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 18, p. 2747 - 2755
  • 14
  • [ 27060-75-9 ]
  • [ 208399-66-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 10, p. 2553 - 2570
[2] Journal of Medicinal Chemistry, 2005, vol. 48, # 12, p. 3953 - 3979
[3] European Journal of Organic Chemistry, 1998, # 5, p. 877 - 888
[4] Organic and Biomolecular Chemistry, 2004, vol. 2, # 23, p. 3504 - 3509
[5] Journal of the Chemical Society, Perkin Transactions 1, 2000, # 5, p. 787 - 797
[6] Journal of Medicinal Chemistry, 2012, vol. 55, # 5, p. 2324 - 2341
  • 15
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  • [ 208399-66-0 ]
YieldReaction ConditionsOperation in experiment
69% With n-butyllithium In hexane 4-Methoxy-2-methylphenylboronic Acid
The title compound was prepared by reacting 4-bromo-3-methylanisole (10 g, 0.050 mol) with n-butyl lithium (24 mL of 2.5 M solution in hexane, 0.055 mol) followed by triisopropyl borate (57.7 mL, 47.02 g, 0.25 mol) according to method F to yield 5.7 g (69percent) of a white solid: MS (ESI) m/z 313 (2M-H2O-H)-.
Reference: [1] Organic Letters, 2001, vol. 3, # 26, p. 4263 - 4265
[2] Patent: US2003/181519, 2003, A1,
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