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[ CAS No. 539-74-2 ] {[proInfo.proName]}

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Chemical Structure| 539-74-2
Chemical Structure| 539-74-2
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Product Details of [ 539-74-2 ]

CAS No. :539-74-2 MDL No. :MFCD00000251
Formula : C5H9BrO2 Boiling Point : -
Linear Structure Formula :Br(CH2)2CO2CH2CH3 InChI Key :FQTIYMRSUOADDK-UHFFFAOYSA-N
M.W : 181.03 Pubchem ID :68320
Synonyms :

Calculated chemistry of [ 539-74-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 4
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 35.3
TPSA : 26.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.57 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.09
Log Po/w (XLOGP3) : 1.18
Log Po/w (WLOGP) : 1.33
Log Po/w (MLOGP) : 1.45
Log Po/w (SILICOS-IT) : 1.34
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.44
Solubility : 6.55 mg/ml ; 0.0362 mol/l
Class : Very soluble
Log S (Ali) : -1.33
Solubility : 8.51 mg/ml ; 0.047 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.02
Solubility : 1.72 mg/ml ; 0.00951 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.94

Safety of [ 539-74-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P305+P351+P338 UN#:N/A
Hazard Statements:H227-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 539-74-2 ]

* 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 [ 539-74-2 ]
  • Downstream synthetic route of [ 539-74-2 ]

[ 539-74-2 ] Synthesis Path-Upstream   1~28

  • 1
  • [ 41330-13-6 ]
  • [ 539-74-2 ]
  • [ 3674-13-3 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 2579,2587
  • 2
  • [ 140-88-5 ]
  • [ 539-74-2 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogen bromide In diethyl ether at 0 - 5℃; for 12 h; A solution of ethyl acrylate (200 g) in ether (400 ml) was cooled to 0°-5° C.
In a separate reaction vessel bromine (278 ml) was added dropwise to tetraline (213 ml) over a period of 3 hours and the HBr gas thereby formed was passed into the ethyl acrylate solution.
The reaction mixture was stirred for 12 hours.
The ether was removed under reduced pressure and the residue was distilled at 70° C. (9 mm Hg).
Yield: 360 g (99percent), colourless oil.
Reference: [1] Patent: US2009/156593, 2009, A1, . Location in patent: Page/Page column 10
[2] Journal of the American Chemical Society, 1934, vol. 56, p. 698
[3] Org.Synth. Coll.Vol.III<1955>577,
[4] Annales de Chimie (Cachan, France), 1921, vol. <9>15, p. 246[5] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1921, vol. 172, p. 1269
[6] Journal fuer Praktische Chemie (Leipzig), 1960, vol. 10, p. 265 - 289
  • 3
  • [ 623-71-2 ]
  • [ 539-74-2 ]
  • [ 51070-66-7 ]
Reference: [1] Synthetic Communications, 1984, vol. 14, # 14, p. 1313 - 1320
  • 4
  • [ 590-92-1 ]
  • [ 64-17-5 ]
  • [ 539-74-2 ]
Reference: [1] Organic Syntheses 3 <New York 1923>,S.51,
[2] Organic Syntheses 3 <New York 1923>,S.51,
[3] Journal of Organic Chemistry, 1961, vol. 26, p. 3666 - 3669
[4] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3830 - 3834[5] Angew. Chem., 2014, vol. 126, # 15, p. 3908 - 3913,6
[6] ACS Chemical Neuroscience, 2017, vol. 8, # 9, p. 1949 - 1959
  • 5
  • [ 27374-25-0 ]
  • [ 539-74-2 ]
Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, p. 651
  • 6
  • [ 41330-13-6 ]
  • [ 539-74-2 ]
  • [ 3674-13-3 ]
Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 2579,2587
  • 7
  • [ 57-57-8 ]
  • [ 64-17-5 ]
  • [ 539-74-2 ]
Reference: [1] Patent: US2422728, 1945, ,
  • 8
  • [ 98071-69-3 ]
  • [ 539-74-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 1813; engl. Ausg. S. 1851
  • 9
  • [ 107-13-1 ]
  • [ 539-74-2 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1955, vol. 20, p. 1004
  • 10
  • [ 590-92-1 ]
  • [ 539-74-2 ]
Reference: [1] Journal fuer Praktische Chemie (Leipzig), 1890, vol. <2>42, p. 384
[2] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1894, vol. 118, p. 1268
  • 11
  • [ 186581-53-3 ]
  • [ 105-36-2 ]
  • [ 539-74-2 ]
Reference: [1] Journal of the American Chemical Society, 1952, vol. 74, p. 5822,5825
  • 12
  • [ 539-74-2 ]
  • [ 593-51-1 ]
  • [ 6315-60-2 ]
Reference: [1] Journal of the American Chemical Society, 1924, vol. 46, p. 1725
  • 13
  • [ 539-74-2 ]
  • [ 74-89-5 ]
  • [ 6315-60-2 ]
Reference: [1] Zhurnal Obshchei Khimii, 1941, vol. 11, p. 935[2] Chem.Abstr., 1943, p. 381
  • 14
  • [ 539-74-2 ]
  • [ 623-72-3 ]
  • [ 140-88-5 ]
Reference: [1] Journal of Chemical Research, Miniprint, 1989, # 11, p. 2554 - 2571
[2] Journal of Chemical Research, Miniprint, 1989, # 11, p. 2554 - 2571
  • 15
  • [ 539-74-2 ]
  • [ 6414-69-3 ]
Reference: [1] Journal of Labelled Compounds and Radiopharmaceuticals, 2002, vol. 45, # 2, p. 139 - 143
[2] Angewandte Chemie - International Edition, 2014, vol. 53, # 48, p. 13253 - 13257[3] Angew. Chem., 2014, vol. 126, # 48, p. 13469 - 13473,5
[4] Tetrahedron, 1999, vol. 55, # 18, p. 5741 - 5758
[5] Bioscience, Biotechnology and Biochemistry, 1997, vol. 61, # 10, p. 1724 - 1728
[6] Journal of Organic Chemistry, 2006, vol. 71, # 18, p. 6734 - 6741
[7] Journal fuer Praktische Chemie (Leipzig), 1960, vol. 10, p. 265 - 289
[8] Journal of the American Chemical Society, 2005, vol. 127, # 11, p. 3678 - 3679
[9] Journal of the American Chemical Society, 2000, vol. 122, # 40, p. 9600 - 9609
[10] Angewandte Chemie - International Edition, 2014, vol. 53, # 15, p. 3830 - 3834[11] Angew. Chem., 2014, vol. 126, # 15, p. 3908 - 3913,6
[12] Patent: US2014/364413, 2014, A1, . Location in patent: Paragraph 0865; 0866
  • 16
  • [ 539-74-2 ]
  • [ 2408-36-8 ]
  • [ 10137-67-4 ]
Reference: [1] Tetrahedron Letters, 1987, vol. 28, # 36, p. 4189 - 4190
  • 17
  • [ 773837-37-9 ]
  • [ 539-74-2 ]
  • [ 10137-67-4 ]
Reference: [1] ACS Chemical Neuroscience, 2017, vol. 8, # 9, p. 1949 - 1959
  • 18
  • [ 539-74-2 ]
  • [ 2303-76-6 ]
  • [ 3699-67-0 ]
Reference: [1] Journal of the American Chemical Society, 1946, vol. 68, p. 2398
  • 19
  • [ 539-74-2 ]
  • [ 122-52-1 ]
  • [ 3699-67-0 ]
Reference: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 6, p. 1929 - 1932[2] Angew. Chem., 2015, vol. 127, # 6, p. 1949 - 1952,4
  • 20
  • [ 539-74-2 ]
  • [ 122-52-1 ]
  • [ 74-96-4 ]
  • [ 3699-67-0 ]
  • [ 140-88-5 ]
Reference: [1] Journal of Organic Chemistry, 1959, vol. 24, p. 532,535
  • 21
  • [ 539-74-2 ]
  • [ 75-16-1 ]
  • [ 35979-69-2 ]
YieldReaction ConditionsOperation in experiment
75.1% at 0℃; Intermediate 45 4-bromo-2-methylbutan-2-ol To a solution of methyl 3-bromopropanoate (0.2 g, 1.2 mmol,) in THF (5 mL) was added methyl magnesium bromide (2.4 mL, 2.4 mmol) at 0 °C. The mixture was stirred at this temperature until the substrate was consumed based on tic [petroleum ether/ethyl acetate (3: 1); product Rf 0.3]. The reaction was quenched with ammonium chloride (2 mL) at 0 °C. The mixture was partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated, to give a crude product which was purified by a column chromatography eluting with petroleum ether/ ethyl acetate (3: 1 ) to give 4-bromo-2- methylbutan-2-ol (0.15 g, 75.1 percent yield) as a yellow oil.
Reference: [1] Patent: WO2014/143799, 2014, A2, . Location in patent: Page/Page column 403
[2] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 2, p. 525 - 535
[3] Journal of Organometallic Chemistry, 1973, vol. 47, p. 337 - 350
[4] Tetrahedron Letters, 1992, vol. 33, # 1, p. 105 - 108
[5] ACS Medicinal Chemistry Letters, 2012, vol. 3, # 10, p. 828 - 833
[6] Patent: WO2013/53983, 2013, A1, . Location in patent: Page/Page column 32
[7] Patent: US2015/11548, 2015, A1, . Location in patent: Paragraph 0138
  • 22
  • [ 539-74-2 ]
  • [ 35979-69-2 ]
Reference: [1] Patent: US2004/220191, 2004, A1,
  • 23
  • [ 539-74-2 ]
  • [ 35979-69-2 ]
YieldReaction ConditionsOperation in experiment
45% With hydrogenchloride; methylmagnesium bromide In tetrahydrofuran EXAMPLE 22
Preparation of 4-bromo-2-methyl-2-butanol
To a solution of 6.25 g (34.5 mmol) of ethyl 3-bromopropionate in 28 ml of dry tetrahydrofuran at -20° C. was added dropwise 28.8 ml (80.6 mmol) of 2.8M methylmagnesium bromide in ether.
The mixture was stirred at room temperature for 2 hours and 50 minutes then quenched by addition of 15 ml of saturated aqueous ammonium chloride.
After addition of 42 ml of 1N aqueous HCl, the organic phase was separated and the aqueous phase extracted with ether.
The combined organic extracts were washed with saturated brine, dried (Na2 SO4) and evaporated to dryness.
The residue was chromatographed on silica gel (40-63μ) using 30percent ethyl acetate-hexane to give 2.57 g (45percent) of 4-bromo-2-methyl-2-butanol as an oil: IR (CHCl3) 3605 cm-1; 1 H NMR (CDCl3) δ1.27 (s, 6 H), 1.33 (s, 1 H), 2.11 (m, 2 H), 3.51 (m, 2 H); MS m/e 151 (M+ --CH3).
Reference: [1] Patent: US5087619, 1992, A,
  • 24
  • [ 917-64-6 ]
  • [ 539-74-2 ]
  • [ 35979-69-2 ]
Reference: [1] Helvetica Chimica Acta, 1979, vol. 62, p. 1854 - 1865
[2] Journal of the Chemical Society, Faraday Transactions 1: Physical Chemistry in Condensed Phases, 1984, vol. 80, p. 3391 - 3398
[3] Tetrahedron Letters, 2000, vol. 41, # 38, p. 7337 - 7340
  • 25
  • [ 539-74-2 ]
  • [ 100-46-9 ]
  • [ 23583-21-3 ]
Reference: [1] European Journal of Medicinal Chemistry, 1996, vol. 31, # 11, p. 847 - 859
[2] Journal of the American Chemical Society, 1927, vol. 49, p. 2865
  • 26
  • [ 539-74-2 ]
  • [ 100-46-9 ]
  • [ 23583-21-3 ]
  • [ 6938-07-4 ]
Reference: [1] Dalton Transactions, 2006, # 33, p. 4029 - 4038
  • 27
  • [ 539-74-2 ]
  • [ 4244-84-2 ]
Reference: [1] Bulletin de la Societe Chimique de France, 1985, # 5, p. 815 - 819
  • 28
  • [ 539-74-2 ]
  • [ 4712-55-4 ]
  • [ 16139-79-0 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 9, p. 2126 - 2129
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