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[ CAS No. 103347-14-4 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 103347-14-4
Chemical Structure| 103347-14-4
Chemical Structure| 103347-14-4
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Product Details of [ 103347-14-4 ]

CAS No. :103347-14-4 MDL No. :MFCD09907927
Formula : C8H8BrClO Boiling Point : -
Linear Structure Formula :- InChI Key :PLBDOPBECRIDKT-UHFFFAOYSA-N
M.W : 235.51 Pubchem ID :13662859
Synonyms :

Calculated chemistry of [ 103347-14-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.78
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 : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.52
Log Po/w (XLOGP3) : 2.41
Log Po/w (WLOGP) : 3.09
Log Po/w (MLOGP) : 3.17
Log Po/w (SILICOS-IT) : 3.46
Consensus Log Po/w : 2.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.09
Solubility : 0.191 mg/ml ; 0.000813 mol/l
Class : Soluble
Log S (Ali) : -2.25
Solubility : 1.34 mg/ml ; 0.00568 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.41
Solubility : 0.00927 mg/ml ; 0.0000394 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.67

Safety of [ 103347-14-4 ]

Signal Word:Danger Class:8
Precautionary Statements:P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405 UN#:1759
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 103347-14-4 ]

* 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 [ 103347-14-4 ]
  • Downstream synthetic route of [ 103347-14-4 ]

[ 103347-14-4 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 73909-16-7 ]
  • [ 103347-14-4 ]
YieldReaction ConditionsOperation in experiment
100% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1 h; Reflux To a solution of 2-chloro-5-methylanisole (11) (274 g, 1.75 mol) in CC14 (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and NBS (321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h with mechanical stirring. The reaction mixture was cooled, washed with IN HCl (2 L), satd NaHC03 (2 L) and brine (2 L), dried over MgS04, filtered and concentrated under reduced pressure to give the 5-(bromomethyl)-3- chloroanisole (12) as a light yellow solid (412 g, quantitative). 1H NMR (400MHz, CDC13): δ 7.30-7.34 (d, 1H), 6.95 (s, 1H), 6.91-6.93 (d, 1H), 4.45 (s, 2H), 3.92 (s, 3H).
100% With N-Bromosuccinimide; dibenzoyl peroxide In tetrachloromethane for 1 h; Reflux To a solution of 2-chloro-5-methylanisole (11) (274 g, 1.75 mol) in CCl4 (2.5 L) was added benzoyl peroxide (4.23 g, 0.02 mol) and NBS (321 g, 1.80 mol). The reaction mixture was heated to reflux for 1 h with mechanical stirring. The reaction mixture was cooled, washed with IN HCl (2 L), satd NaHCO3 (2 L) and brine (2 L), dried over MgSO4, filtered and concentrated under reduced pressure to give the 5-(bromomethyl)-3- chloroanisole (12) as a light yellow solid (412 g, quantitative). 1H NMR (400MHz, CDCl3): δ 7.30-7.34 (d, IH), 6.95 (s, IH), 6.91-6.93 (d, IH), 4.45 (s, 2H), 3.92 (s, 3H).
92% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3 h; Heating / reflux To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57 g, 0.32 mol) and AIBN (10 g, 60 mmol). The mixture was heated at reflux for 3 hours. The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92percent). 1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H).
92% With N-Bromosuccinimide; azobisisobutyronitrile In tetrachloromethane 4-Bromomethyl-1-chloro-2-methoxy-benzene
To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57 g, 0.32 mol) and AIBN (10 g, 60 mmol).
The mixture was heated at reflux for 3 hours.
The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92percent).
1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H).
92% With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) In tetrachloromethane for 3 h; Reflux 4-Bromomethyl-1-chloro-2-methoxy-benzene
To a solution of 1-chloro-2-methoxy-4-methyl-benzene (50 g, 0.32 mol) in CCl4 (350 mL) was added NBS (57 g, 0.32 mol) and AIBN (10 g, 60 mmol).
The mixture was heated at reflux for 3 hours.
The solvent was evaporated under vacuum and the residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate=20:1) to give 4-bromomethyl-1-chloro-2-methoxy-benzene (69 g, 92percent).
1H NMR (400 MHz, CDCl3) δ 7.33-7.31 (m, 1H), 6.95-6.91 (m, 2H), 4.46 (s, 2H), 3.92 (s, 3H).

Reference: [1] Patent: WO2011/71565, 2011, A1, . Location in patent: Page/Page column 145-146
[2] Patent: WO2010/93845, 2010, A1, . Location in patent: Page/Page column 136-137
[3] Patent: US6984657, 2006, B1,
[4] Patent: US2007/244159, 2007, A1, . Location in patent: Page/Page column 91
[5] Patent: US2011/98311, 2011, A1,
[6] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1575
[7] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 18, p. 6715 - 6727
[8] Tetrahedron Letters, 1989, vol. 30, # 40, p. 5417 - 5420
[9] Journal of Organic Chemistry, 1987, vol. 52, # 19, p. 4303 - 4307
[10] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1615 - 1627
[11] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5397 - 5400
[12] Patent: US2005/239881, 2005, A1, . Location in patent: Page/Page column 27
[13] Patent: WO2007/39736, 2007, A1, . Location in patent: Page/Page column 28
[14] Patent: US2008/293775, 2008, A1, . Location in patent: Page/Page column 22
[15] Patent: US2004/192704, 2004, A1, . Location in patent: Page 23
[16] Patent: US2004/198736, 2004, A1, . Location in patent: Page/Page column 60
  • 2
  • [ 13726-17-5 ]
  • [ 103347-14-4 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5397 - 5400
[2] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
[3] Patent: WO2005/42516, 2005, A2, . Location in patent: Page/Page column 95
  • 3
  • [ 73909-16-7 ]
  • [ 103347-14-4 ]
Reference: [1] Patent: US6384080, 2002, B1,
  • 4
  • [ 615-74-7 ]
  • [ 103347-14-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1986, vol. 29, # 9, p. 1615 - 1627
[2] Tetrahedron Letters, 1989, vol. 30, # 40, p. 5417 - 5420
[3] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5397 - 5400
[4] Patent: WO2011/71565, 2011, A1,
[5] Patent: WO2010/93845, 2010, A1,
[6] Patent: US2011/98311, 2011, A1,
[7] Patent: US2015/231142, 2015, A1,
[8] Patent: US6384080, 2002, B1,
[9] Patent: US6384080, 2002, B1,
  • 5
  • [ 73909-16-7 ]
  • [ 1355637-28-3 ]
  • [ 103347-14-4 ]
Reference: [1] Patent: WO2012/7868, 2012, A2, . Location in patent: Page/Page column 93-94
  • 6
  • [ 693-95-8 ]
  • [ 52829-53-5 ]
  • [ 103347-14-4 ]
Reference: [1] Patent: US6384080, 2002, B1,
  • 7
  • [ 13726-16-4 ]
  • [ 103347-14-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
  • 8
  • [ 56962-12-0 ]
  • [ 103347-14-4 ]
Reference: [1] Journal of Medicinal Chemistry, 1989, vol. 32, # 8, p. 1757 - 1763
  • 9
  • [ 67341-33-7 ]
  • [ 98544-66-2 ]
  • [ 103347-14-4 ]
Reference: [1] Patent: US6384080, 2002, B1,
  • 10
  • [ 3031-86-5 ]
  • [ 247569-90-0 ]
  • [ 103347-14-4 ]
Reference: [1] Patent: US6384080, 2002, B1,
  • 11
  • [ 85740-98-3 ]
  • [ 103347-14-4 ]
Reference: [1] Tetrahedron Letters, 1986, vol. 27, # 45, p. 5397 - 5400
  • 12
  • [ 143-33-9 ]
  • [ 103347-14-4 ]
  • [ 13726-21-1 ]
YieldReaction ConditionsOperation in experiment
48% at 60℃; To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.290 mol) in C2H5OH (90percent, 500 mL) was added NaCN (28.5 g, 0.580 mol). The mixture was stirred at 60° C. overnight. Ethanol was evaporated and the residue was dissolved in H2O. The mixture was extracted with ethyl acetate (300 mL.x.3). The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48percent). 1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H). 13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5.
Reference: [1] Patent: US2007/244159, 2007, A1, . Location in patent: Page/Page column 91
[2] Patent: US2005/239881, 2005, A1, . Location in patent: Page/Page column 27
[3] Patent: WO2007/39736, 2007, A1, . Location in patent: Page/Page column 28
[4] Patent: US2008/293775, 2008, A1, . Location in patent: Page/Page column 22
[5] Patent: US2004/192704, 2004, A1, . Location in patent: Page 23
[6] Patent: US2004/198736, 2004, A1, . Location in patent: Page/Page column 60
  • 13
  • [ 773837-37-9 ]
  • [ 103347-14-4 ]
  • [ 13726-21-1 ]
YieldReaction ConditionsOperation in experiment
75% for 2 h; Reflux To a solution of 5-(bromomethyl)-3-chloroanisole (12) (412 g, 1.75 mol) in EtOH (2 L) and H20 (0.5 L) was added NaCN (129 g, 2.63 mol) and the reaction mixture was heated to reflux for 2 h with mechanical stirring. The reaction mixture was cooled and diluted with water (3.5 L). The mixture was extracted with diethyl ether (2 L x 2) and the combined organic layers were washed with aq. 5percent HC1 (2.5 L), satd NaHC03 (2.5 L) and brine (2.5 L), dried over anhydrous MgS04, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc = 5: 1) to afford 2-(4-chloro-3-methoxyphenyl)acetonitrile (13) (240 g, 75percent) as yellow solid. 1H NMR (400MHz, CDC13): δ 7.35-7.36 (d, 1H), 6.86 (s, 1H), 6.84-6.86 (d, 1H), 3.92 (s, 3H), 3.74 (s, 2H).
75% for 2 h; Reflux To a solution of 5-(bromomethyl)-3-chloroanisole (12) (412 g, 1.75 mol) in EtOH (2 L) and H2O (0.5 L) was added NaCN (129 g, 2.63 mol) and the reaction mixture was heated to reflux for 2 h with mechanical stirring. The reaction mixture was cooled and diluted with water (3.5 L). The mixture was extracted with diethyl ether (2 L x 2) and the combined organic layers were washed with aq. 5percent HCl (2.5 L), satd NaHCO3 (2.5 L) and brine (2.5 L), dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting residue was purified by column chromatography (Hex/EtOAc = 5:1) to afford 2-(4-chloro-3-methoxyphenyl)acetonitrile (13) (240 g, 75percent) as yellow solid. 1H NMR (400MHz, CDCl3): δ 7.35-7.36 (d, IH), 6.86 (s, IH), 6.84-6.86 (d, IH), 3.92 (s, 3H), 3.74 (s, 2H).
48% at 60℃; To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.290 mol) in C2H5OH (90percent, 500 mL) was added NaCN (28.5 g, 0.580 mol).
The mixture was stirred at 60° C. overnight.
Ethanol was evaporated and the residue was dissolved in H2O.
The mixture was extracted with ethyl acetate (300 mL*3).
The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48percent).
1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H).
13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5.
Reference: [1] Patent: WO2011/71565, 2011, A1, . Location in patent: Page/Page column 146
[2] Patent: WO2010/93845, 2010, A1, . Location in patent: Page/Page column 136-138
[3] Patent: US2015/231142, 2015, A1, . Location in patent: Paragraph 1576
  • 14
  • [ 103347-14-4 ]
  • [ 13726-21-1 ]
YieldReaction ConditionsOperation in experiment
48% With NaCN In C2H5OH; water 2-(4-Chloro-3-methoxyphenyl)acetonitrile
To a solution of 4-bromomethyl-1-chloro-2-methoxy-benzene (68.5 g, 0.290 mol) in C2H5OH (90percent, 500 mL) was added NaCN (28.5 g, 0.580 mol).
The mixture was stirred at 60° C. overnight.
Ethanol was evaporated and the residue was dissolved in H2O.
The mixture was extracted with ethyl acetate (300 mL*3).
The combined organic layers were washed with brine, dried over Na2SO4 and purified by column chromatography on silica gel (petroleum ether/ethyl acetate 30:1) to give 2-(4-chloro-3-methoxyphenyl)acetonitrile (25 g, 48percent).
1H NMR (400 MHz, CDCl3) δ 7.36 (d, J=8 Hz, 1H), 6.88-6.84 (m, 2H), 3.92 (s, 3H), 3.74 (s, 2H).
13C NMR (100 MHz, CDCl3) δ 155.4, 130.8, 129.7, 122.4, 120.7, 117.5, 111.5, 56.2, 23.5.
Reference: [1] Patent: US2011/98311, 2011, A1,
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