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[ CAS No. 542-28-9 ] {[proInfo.proName]}

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Excepted Quantity USD 0.00
Limited Quantity USD 15-60
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Inaccessible (Haz class 6.1), International USD 150+
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Chemical Structure| 542-28-9
Chemical Structure| 542-28-9
Structure of 542-28-9 * Storage: {[proInfo.prStorage]}
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Product Details of [ 542-28-9 ]

CAS No. :542-28-9 MDL No. :MFCD00006645
Formula : C5H8O2 Boiling Point : -
Linear Structure Formula :- InChI Key :OZJPLYNZGCXSJM-UHFFFAOYSA-N
M.W : 100.12 Pubchem ID :10953
Synonyms :
δ-Valerolactone;5-Valerolactone;oxan-2-one

Calculated chemistry of [ 542-28-9 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 0
Num. H-bond acceptors : 2.0
Num. H-bond donors : 0.0
Molar Refractivity : 25.32
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) : -7.16 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.35
Log Po/w (XLOGP3) : -0.35
Log Po/w (WLOGP) : 0.71
Log Po/w (MLOGP) : 0.5
Log Po/w (SILICOS-IT) : 1.64
Consensus Log Po/w : 0.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.24
Solubility : 57.6 mg/ml ; 0.575 mol/l
Class : Very soluble
Log S (Ali) : 0.26
Solubility : 182.0 mg/ml ; 1.82 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.82
Solubility : 15.2 mg/ml ; 0.152 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.07

Safety of [ 542-28-9 ]

Signal Word:Danger Class:9
Precautionary Statements:P210-P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P332+P313-P362+P364-P370+P378-P403+P235-P501 UN#:3082
Hazard Statements:H227-H302-H315-H318 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 542-28-9 ]

* 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 [ 542-28-9 ]
  • Downstream synthetic route of [ 542-28-9 ]

[ 542-28-9 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 542-28-9 ]
  • [ 38041-19-9 ]
YieldReaction ConditionsOperation in experiment
12% With ammonium acetate; sodium cyanoborohydride In methanol EXAMPLE 21
N-4-Tetrahydropyranyl-4-(1H-2-methylimidazo[4,5-c]pyridin-1-ylmethyl)-N-{3-[6-(3-pyrrolidin-1-yl-1-{4-tolyl}-prop-1E-enyl)-pyridin-2-yl]-prop-2E-enyl}-benzamide STR32 (a) 4-Amino-tetrahydropyran
A mixture of tetrahydropyranone (1.0 g, 10.0 mmol), ammonium acetate (7.69 g, 100.0 mmol), 3 Å molecular sieve powder (2.5 g) and sodium cyanoborohydride (1.25 g, 20.0 mmol) suspended in dry methanol (50 ml) under a blanket of argon was refluxed for 2 hours and allowed to cool to room temperature.
The suspension was filtered and concentrated under reduced pressure.
The residue was partitioned between DCM and water.
The organic layer was extracted with 1M HCl (*2).
The combined extracts were basified with 5M sodium hydroxide solution and extracted with DCM.
The combined organics were dried over magnesium sulphate, filtered and concentrated under reduced pressure to yield 4-amino-tetrahydropyran as a colourless oil (120 mg, 12percent).
1 H-NMR; δ (CDCl3), 3.95-3.86 (2H, m), 3.38-3.27 (2H, m), 2.85-2.73 (1H, m), 1.79-1.67 (2H, m), 1.40-1.24 (2H, m).
Reference: [1] Patent: US5866588, 1999, A,
  • 2
  • [ 142-68-7 ]
  • [ 96-47-9 ]
  • [ 2081-44-9 ]
  • [ 96-48-0 ]
  • [ 542-28-9 ]
  • [ 29943-42-8 ]
  • [ 1487-44-1 ]
Reference: [1] International Journal of Chemical Kinetics, 2013, vol. 45, # 5, p. 295 - 305
  • 3
  • [ 142-68-7 ]
  • [ 96-47-9 ]
  • [ 2081-44-9 ]
  • [ 96-48-0 ]
  • [ 542-28-9 ]
  • [ 29943-42-8 ]
  • [ 1487-44-1 ]
Reference: [1] International Journal of Chemical Kinetics, 2013, vol. 45, # 5, p. 295 - 305
  • 4
  • [ 542-28-9 ]
  • [ 16874-33-2 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 33, p. 8149 - 8150
  • 5
  • [ 109-52-4 ]
  • [ 542-28-9 ]
  • [ 16874-33-2 ]
  • [ 108-29-2 ]
Reference: [1] Journal of the American Chemical Society, 2001, vol. 123, # 33, p. 8149 - 8150
  • 6
  • [ 73819-79-1 ]
  • [ 542-28-9 ]
  • [ 23462-75-1 ]
  • [ 73819-79-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 45 - 48
  • 7
  • [ 73819-79-1 ]
  • [ 542-28-9 ]
  • [ 23462-75-1 ]
  • [ 73819-79-1 ]
Reference: [1] Journal of Heterocyclic Chemistry, 1980, vol. 17, p. 45 - 48
  • 8
  • [ 542-28-9 ]
  • [ 67-56-1 ]
  • [ 5454-83-1 ]
Reference: [1] Canadian Journal of Chemistry, 2003, vol. 81, # 8, p. 937 - 960
  • 9
  • [ 542-28-9 ]
  • [ 64-17-5 ]
  • [ 14660-52-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1976, p. 2190 - 2193
[2] Journal of Organic Chemistry, 1976, vol. 41, p. 362 - 367
  • 10
  • [ 542-28-9 ]
  • [ 1501-27-5 ]
Reference: [1] Journal of Organic Chemistry, 1982, vol. 47, # 12, p. 2400 - 2404
  • 11
  • [ 67-56-1 ]
  • [ 542-28-9 ]
  • [ 627-93-0 ]
  • [ 4547-43-7 ]
  • [ 1119-40-0 ]
  • [ 14273-92-8 ]
  • [ 931-17-9 ]
  • [ 556-48-9 ]
  • [ 106-65-0 ]
Reference: [1] Patent: EP1189859, 2004, B1, . Location in patent: Page 9
  • 12
  • [ 67-56-1 ]
  • [ 124-04-9 ]
  • [ 1191-25-9 ]
  • [ 556-48-9 ]
  • [ 637-88-7 ]
  • [ 542-28-9 ]
  • [ 627-93-0 ]
  • [ 4547-43-7 ]
  • [ 1119-40-0 ]
  • [ 14273-92-8 ]
  • [ 931-17-9 ]
  • [ 106-65-0 ]
Reference: [1] Patent: WO2004/46072, 2004, A1, . Location in patent: Page/Page column 9-10
  • 13
  • [ 67-56-1 ]
  • [ 64-18-6 ]
  • [ 110-94-1 ]
  • [ 124-04-9 ]
  • [ 1191-25-9 ]
  • [ 13392-69-3 ]
  • [ 556-48-9 ]
  • [ 542-28-9 ]
  • [ 627-93-0 ]
  • [ 4547-43-7 ]
  • [ 1119-40-0 ]
  • [ 14273-92-8 ]
  • [ 931-17-9 ]
  • [ 106-65-0 ]
Reference: [1] Patent: WO2004/26798, 2004, A2, . Location in patent: Page/Page column 10
  • 14
  • [ 542-28-9 ]
  • [ 67-56-1 ]
  • [ 50995-48-7 ]
YieldReaction ConditionsOperation in experiment
45%
Stage #1: at 95 - 120℃; for 0.5 h;
Stage #2: at 0 - 25℃; for 5 h; Heating / reflux
518 g 6-VALEROLACTONE and 5 ml phosphorous tribromide were fed into a 11 three-necked flask. The mixture was heated up to a temperature of 95 °C to 105 °C under stirring and 550 g bromine were added, while the temperature was kept constant between 100 and 120 °C. Subsequently, 5 ml phosphorus tribromide and 236 g bromine were added at a temperature of 110 °C. After the reaction mixture had been allowed to stand for 30 minutes, it was cooled down to a temperature of 0 to 10 °C. Then, 11 methanol and lg p-toluenesulfonic acid were added, while the temperature was kept constant at 25 °C. After 5 hours of refluxing, the excess material was distilled off and the lower organic layer was separated. The organic layer was then washed with 500 ml of 10percent sodium hydroxide and 500 ml water. After separation of the organic layer, the product was isolated by fractional distillation (139 to 142 °C/28 hPa) and 612.7 g of the title compound were obtained (yield 45percent, purity > 96percent by GC).
Reference: [1] Chemical Communications, 2015, vol. 51, # 70, p. 13470 - 13473
[2] Patent: WO2005/28449, 2005, A1, . Location in patent: Page/Page column 11
[3] Tetrahedron, 1998, vol. 54, # 19, p. 4991 - 5004
  • 15
  • [ 542-28-9 ]
  • [ 6399-81-1 ]
  • [ 17814-85-6 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1967, vol. 709, p. 105 - 112
  • 16
  • [ 542-28-9 ]
  • [ 37435-69-1 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydroxide In ethanol at 20 - 80℃; for 2.5 h; Valerolactone (1.0 g, 10 mmol) was added to a solution of NaOH (0.44 g,11 mmol) dissolved in ethanol (90percent, 23 mL) and the mixture was stirred at 80° for 30 min then at ambient temperature for 2 h. Excess solvent was then removed under reduced pressure to yield the sodium salt quantitatively.
Reference: [1] ChemMedChem, 2017, vol. 12, # 3, p. 226 - 234
[2] Tetrahedron, 2017, vol. 73, # 14, p. 1873 - 1880
[3] Journal of the American Chemical Society, 2004, vol. 126, # 42, p. 13588 - 13589
[4] Journal of Organic Chemistry, 2014, vol. 79, # 10, p. 4358 - 4366
[5] Journal of the American Chemical Society, 1929, vol. 51, p. 261
[6] Journal of Medicinal Chemistry, 1991, vol. 34, # 9, p. 2692 - 2701
[7] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 10, p. 4422 - 4431
[8] Patent: EP431972, 1991, A2,
[9] Patent: EP518675, 1992, A2,
[10] Patent: WO2015/69932, 2015, A1, . Location in patent: Page/Page column 157
[11] Patent: WO2015/188197, 2015, A2, . Location in patent: Page/Page column 157; 158
[12] Patent: WO2016/94677, 2016, A2, . Location in patent: Page/Page column 52
[13] Patent: WO2017/100461, 2017, A1, . Location in patent: Page/Page column 60
[14] Patent: US6087502, 2000, A,
[15] Patent: WO2018/35380, 2018, A1, . Location in patent: Page/Page column 93
[16] ACS Medicinal Chemistry Letters, 2018, vol. 9, # 6, p. 534 - 539
  • 17
  • [ 542-28-9 ]
  • [ 87392-05-0 ]
Reference: [1] Chemistry Letters, 2016, vol. 45, # 3, p. 353 - 355
[2] Chemistry Letters, 2016, vol. 45, # 3, p. 353 - 355
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