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[ CAS No. 5437-45-6 ] {[proInfo.proName]}

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Chemical Structure| 5437-45-6
Chemical Structure| 5437-45-6
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Product Details of [ 5437-45-6 ]

CAS No. :5437-45-6 MDL No. :MFCD00000190
Formula : C9H9BrO2 Boiling Point : -
Linear Structure Formula :- InChI Key :JHVLLYQQQYIWKX-UHFFFAOYSA-N
M.W :229.07 Pubchem ID :62576
Synonyms :

Calculated chemistry of [ 5437-45-6 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.22
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 50.18
TPSA : 26.3 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) : -5.74 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.27
Log Po/w (XLOGP3) : 2.75
Log Po/w (WLOGP) : 1.97
Log Po/w (MLOGP) : 2.43
Log Po/w (SILICOS-IT) : 2.57
Consensus Log Po/w : 2.4

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.1
Solubility : 0.182 mg/ml ; 0.000797 mol/l
Class : Soluble
Log S (Ali) : -2.96
Solubility : 0.253 mg/ml ; 0.0011 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.75
Solubility : 0.0403 mg/ml ; 0.000176 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.7

Safety of [ 5437-45-6 ]

Signal Word:Danger Class:8
Precautionary Statements:P301+P330+P331-P303+P361+P353-P363-P304+P340-P310-P321-P260-P264-P280-P305+P351+P338-P405-P501 UN#:3265
Hazard Statements:H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 5437-45-6 ]

* 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 [ 5437-45-6 ]
  • Downstream synthetic route of [ 5437-45-6 ]

[ 5437-45-6 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 109-01-3 ]
  • [ 5437-45-6 ]
  • [ 54699-92-2 ]
Reference: [1] Patent: US6479519, 2002, B1,
  • 2
  • [ 79-08-3 ]
  • [ 100-51-6 ]
  • [ 103-50-4 ]
  • [ 5437-45-6 ]
YieldReaction ConditionsOperation in experiment
82% at 80℃; for 6 h; Inert atmosphere General procedure: A mixture of the silica gel-adsorbed acid 2 (0.033 g), 2-bromoacetic acid (3a) (0.137 g, 0.988 mmol), and phenylmethanol (4a) (0.108 g, 1.000 mmol) under argon was stirred at 80 °C for 24 h. After the reaction mixture was cooled to room temperature, the addition of diethyl ether (5 mL × 5) and decantation resulted in complete separation of the organic layer and the silica gel-adsorbed acid 2. After the solvent was removed under reduced pressure, the product was purified by column chromatography on silica gel with hexane/EtOAc (v/v = 10/1) to give benzyl 2-bromoacetate (5aa) (0.189 g, 83percent). The silica gel-adsorbed acid 2 was dried under vacuum at room temperature, and recovered as a white powder (0.033 g, 99percent).
Reference: [1] Journal of Molecular Catalysis A: Chemical, 2013, vol. 367, p. 116 - 120
  • 3
  • [ 79-08-3 ]
  • [ 100-51-6 ]
  • [ 5437-45-6 ]
YieldReaction ConditionsOperation in experiment
100% With toluene-4-sulfonic acid In benzene at 120℃; for 24 h; [First Step]:
Bromoacetic acid (20.8 g, 150 mmol), benzyl alcohol (16.2 g, 150 mmol), p-toluenesulfonic acid (258 mg, 1.5 mmol) and benzene (300 mL) were added to a two-necked flask equipped with a Dean-Stark trap, and were subjected to dehydration condensation at 120°C for 24 hours, and then the solvent was distilled off under reduced pressure with an evaporator.
Then, the residue was purified by silica gel flash column chromatography (hexane/ethyl acetate=10/1, 5/1), and thus bromoacetic acid benzyl ester (34.3 g, 150 mmol) was obtained quantitatively as a yellow oily product.
Rf 0.71 (hexane/ethyl acetate=4/1);
1H NMR (500 MHz, ppm, CDCl3, J=Hz) δ 3.81 (s, 2H), 5.14 (s, 2H), 7.31 (s, 5H);
13C NMR (125 MHz, ppm, CDCl3) δ 25.74, 67.79, 128.27, 128.48, 128.54, 134.88, 166.91;
IR (neat, cm-1) 2959, 1751, 1458, 1412, 1377, 1167, 972, 750, 698
100% at 120℃; for 24 h; Bromoacetic acid (20.8 g, 150 mmol), benzyl alcohol (16.2 g, 150 mmol), p-toluenesulfonic acid (258 mg, 1.5 mmol) and benzene (300 mL) were added to a two-necked flask equipped with a Dean-Stark trap, and were subjected to dehydration condensation at 120°C for 24 hours, and then the solvent was distilled off under reduced pressure with an evaporator.
Then, the residue was purified by silica gel flash column chromatography (hexane/ethyl acetate=10/1, 5/1), and thus bromoacetic acid benzyl ester (34.3 g, 150 mmol) was obtained quantitatively as a yellow oily product.
Rf 0.71 (hexane/ethyl acetate=4/1);
1H NMR (500 MHz, ppm, CDCl3, J=Hz) δ 3.81 (s, 2H), 5.14 (s, 2H), 7.31 (s, 5H);
13C NMR (125 MHz, ppm, CDCl3) δ 25.74, 67.79, 128.27, 128.48, 128.54, 134.88, 166.91;
IR (neat, cm-1) 2959, 1751, 1458, 1412, 1377, 1167, 972, 750, 698
100% With toluene-4-sulfonic acid In benzene at 120℃; for 24 h; Dean-Stark trap [First Step]
In a two-necked flask equipped with a Dean-Stark trap, bromoacetic acid (20.8 g, 150 mmol), benzyl alcohol (16.2 g, 150 mmol), paratoluenesulfonic acid (258 mg, 1.5 mmol) and benzene (300 mL) were charged, followed by dehydration condensation at 120°C for 24 hours.
The solvent was distilled off under reduced pressure using an evaporator, and then purified by silica gel flash column chromatography (hexane/ethyl acetate = 10/1, 5/1) to quantitatively obtain bromoacetic acid benzyl ester (34.3 g, 150 mmol) as a yellow oily product.
Rf 0.71 (hexane/ethyl acetate = 4/1);
1H MR (500 MHz, ppm, CDCl3) δ3.81 (s, 2H), 5.14 (s, 2H), 7.31 (s, 5H); 13C NMR (125 MHz, ppm, CDCl3) δ25.74, 67.79, 128.27, 128.48, 128.54, 134.88, 166.91;
IR (neat, cm-1) 2959, 1751, 1458, 1412, 1377, 1167, 972, 750, 698.
83% at 80℃; for 24 h; Inert atmosphere General procedure: A mixture of the silica gel-adsorbed acid 2 (0.033 g), 2-bromoacetic acid (3a) (0.137 g, 0.988 mmol), and phenylmethanol (4a) (0.108 g, 1.000 mmol) under argon was stirred at 80 °C for 24 h. After the reaction mixture was cooled to room temperature, the addition of diethyl ether (5 mL × 5) and decantation resulted in complete separation of the organic layer and the silica gel-adsorbed acid 2. After the solvent was removed under reduced pressure, the product was purified by column chromatography on silica gel with hexane/EtOAc (v/v = 10/1) to give benzyl 2-bromoacetate (5aa) (0.189 g, 83percent). The silica gel-adsorbed acid 2 was dried under vacuum at room temperature, and recovered as a white powder (0.033 g, 99percent).

Reference: [1] Tetrahedron, 2008, vol. 64, # 8, p. 1823 - 1828
[2] Journal of Materials Chemistry, 2010, vol. 20, # 41, p. 9226 - 9230
[3] Patent: EP2345651, 2011, A1, . Location in patent: Page/Page column 11
[4] Patent: EP2345638, 2011, A1, . Location in patent: Page/Page column 11
[5] Patent: EP2460795, 2012, A1, . Location in patent: Page/Page column 9
[6] Angewandte Chemie - International Edition, 2018, vol. 57, # 11, p. 2958 - 2962[7] Angew. Chem., 2018, vol. 130, # 11, p. 3008 - 3013,6
[8] Journal of Molecular Catalysis A: Chemical, 2013, vol. 367, p. 116 - 120
[9] Journal of Medicinal Chemistry, 2012, vol. 55, # 14, p. 6541 - 6553
[10] Tetrahedron Letters, 1996, vol. 37, # 37, p. 6653 - 6656
[11] Journal of the Chemical Society, 1910, vol. 97, p. 426
[12] Monatshefte fuer Chemie, 1913, vol. 34, p. 1874
[13] Journal of Agricultural and Food Chemistry, 1958, vol. 6, p. 843
[14] J. Gen. Chem. USSR (Engl. Transl.), 1967, vol. 37, # 9, p. 1880 - 1885[15] Zhurnal Obshchei Khimii, 1967, vol. 37, # 9, p. 1980 - 1987
[16] The Journal of organic chemistry, 1976, vol. 41, # 4, p. 699 - 700
[17] Patent: EP2495246, 2012, A1, . Location in patent: Page/Page column 12-13
[18] Medicinal Chemistry Research, 2014, vol. 23, # 1, p. 503 - 517
[19] Organic Letters, 2017, vol. 19, # 13, p. 3524 - 3527
[20] Patent: JP2017/210426, 2017, A, . Location in patent: Paragraph 0053; 0054
  • 4
  • [ 598-21-0 ]
  • [ 100-51-6 ]
  • [ 5437-45-6 ]
Reference: [1] Organic Syntheses, 2012, vol. 89, p. 501 - 509
[2] Synthesis, 2003, # 17, p. 2647 - 2654
[3] Organic Letters, 2007, vol. 9, # 16, p. 3195 - 3197
[4] Angewandte Chemie - International Edition, 2010, vol. 49, # 52, p. 10181 - 10185
[5] Organic Letters, 2016, vol. 18, # 10, p. 2443 - 2446
[6] Chemistry - A European Journal, 2016, vol. 22, # 38, p. 13599 - 13612
[7] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 502 - 511
[8] Organic Letters, 2017, vol. 19, # 9, p. 2282 - 2285
[9] Asian Journal of Chemistry, 2017, vol. 29, # 10, p. 2171 - 2176
[10] Medicinal Chemistry Research, 2018, vol. 27, # 2, p. 458 - 469
[11] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1510 - 1516
[12] Chemical Communications, 2018, vol. 54, # 28, p. 3516 - 3519
[13] Organic Letters, 2018, vol. 20, # 9, p. 2663 - 2666
[14] Organic and Biomolecular Chemistry, 2018, vol. 16, # 25, p. 4683 - 4687
[15] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 7, p. 1720 - 1728
[16] Chinese Journal of Chemistry, 2018, vol. 36, # 9, p. 857 - 865
[17] Synthesis (Germany), 2018, vol. 50, # 16, p. 3187 - 3196
[18] Journal of the American Chemical Society, 2018, vol. 140, # 50, p. 17773 - 17781
  • 5
  • [ 96-32-2 ]
  • [ 100-51-6 ]
  • [ 5437-45-6 ]
Reference: [1] Chemical Communications, 2009, # 41, p. 6249 - 6251
  • 6
  • [ 79-08-3 ]
  • [ 100-51-6 ]
  • [ 5437-45-6 ]
Reference: [1] Patent: US4596791, 1986, A,
  • 7
  • [ 108-95-2 ]
  • [ 5437-45-6 ]
Reference: [1] Patent: US2003/8882, 2003, A1,
  • 8
  • [ 78385-35-0 ]
  • [ 78385-37-2 ]
  • [ 5437-45-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 1435 - 1440
  • 9
  • [ 105-36-2 ]
  • [ 100-51-6 ]
  • [ 5437-45-6 ]
Reference: [1] Journal of the Chemical Society, 1956, p. 1521,1523
  • 10
  • [ 13837-45-1 ]
  • [ 78385-35-0 ]
  • [ 78385-37-2 ]
  • [ 5437-45-6 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1982, p. 1435 - 1440
  • 11
  • [ 103-50-4 ]
  • [ 598-21-0 ]
  • [ 100-39-0 ]
  • [ 5437-45-6 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 5, p. 721 - 728
  • 12
  • [ 288-94-8 ]
  • [ 5437-45-6 ]
  • [ 21743-64-6 ]
  • [ 21732-17-2 ]
Reference: [1] Patent: WO2017/81615, 2017, A1, . Location in patent: Page/Page column 53
  • 13
  • [ 5437-45-6 ]
  • [ 2495-37-6 ]
Reference: [1] Tetrahedron, 1985, vol. 41, # 13, p. 2643 - 2652
  • 14
  • [ 122-52-1 ]
  • [ 5437-45-6 ]
  • [ 7396-44-3 ]
Reference: [1] Organic Letters, 2010, vol. 12, # 7, p. 1460 - 1463
[2] Journal of the American Chemical Society, 2001, vol. 123, # 47, p. 11519 - 11533
[3] Patent: WO2008/7145, 2008, A2, . Location in patent: Page/Page column 17-18
  • 15
  • [ 5437-45-6 ]
  • [ 15097-38-8 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 19, p. 4289 - 4291
[2] Tetrahedron, 2016, vol. 72, # 37, p. 5707 - 5712
[3] Organic Letters, 2017, vol. 19, # 13, p. 3524 - 3527
[4] Advanced Synthesis and Catalysis, 2018, vol. 360, # 7, p. 1510 - 1516
[5] Patent: US2018/99931, 2018, A1,
  • 16
  • [ 603-35-0 ]
  • [ 5437-45-6 ]
  • [ 15097-38-8 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 10, p. 3482 - 3485
[2] Journal of Medicinal Chemistry, 1987, vol. 30, # 6, p. 1097 - 1100
[3] Journal of Organic Chemistry, 1981, vol. 46, # 3, p. 594 - 598
[4] Asian Journal of Chemistry, 2012, vol. 24, # 3, p. 1333 - 1337
[5] Journal of Organic Chemistry, 2017, vol. 82, # 1, p. 502 - 511
  • 17
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  • [ 71-91-0 ]
Reference: [1] Synthesis, 2005, # 20, p. 3555 - 3564
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