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[ CAS No. 2356-16-3 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 2356-16-3
Chemical Structure| 2356-16-3
Structure of 2356-16-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 2356-16-3 ]

CAS No. :2356-16-3 MDL No. :MFCD00134400
Formula : C8H16FO5P Boiling Point : -
Linear Structure Formula :- InChI Key :FVPISMANESAJQZ-UHFFFAOYSA-N
M.W : 242.18 Pubchem ID :2734865
Synonyms :

Calculated chemistry of [ 2356-16-3 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.88
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 0.0
Molar Refractivity : 52.74
TPSA : 71.64 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) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.49
Log Po/w (XLOGP3) : 0.97
Log Po/w (WLOGP) : 2.53
Log Po/w (MLOGP) : 0.67
Log Po/w (SILICOS-IT) : 0.73
Consensus Log Po/w : 1.48

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.42
Solubility : 9.11 mg/ml ; 0.0376 mol/l
Class : Very soluble
Log S (Ali) : -2.06
Solubility : 2.1 mg/ml ; 0.00867 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.78
Solubility : 4.03 mg/ml ; 0.0166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.0

Safety of [ 2356-16-3 ]

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 [ 2356-16-3 ]

* 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 [ 2356-16-3 ]
  • Downstream synthetic route of [ 2356-16-3 ]

[ 2356-16-3 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 401-55-8 ]
  • [ 122-52-1 ]
  • [ 2356-16-3 ]
YieldReaction ConditionsOperation in experiment
92% at 130℃; for 23 h; Ethyl 2-bromo 2-fluoroacetate (5.0 g, 27 mmol) was added to triethylphosphite (13 mL) and heated at 130 °C for 23 h. The resulting mixture was distilled under low pressure (1.4 mbar, 75-110 °C) to give the title compound as a yellowish oil (6.0 g, 92percent).
92% at 130℃; for 23 h; Ethyl 2-bromo 2-fluoroacetate (5.0 g, 27 mmol) was added to triethylphosphite (13 mL) and heated at 130 for 23 h. The resulting mixture was distilled under low pressure (1.4 mbar, 75-110 ) to give the title compound as a yellowish oil (6.0 g, 92percent).
Reference: [1] Phosphorus, Sulfur and Silicon and Related Elements, 2000, vol. 160, p. 195 - 205
[2] Patent: WO2017/100668, 2017, A1, . Location in patent: Page/Page column 162
[3] Patent: WO2018/103058, 2018, A1, . Location in patent: Page/Page column 161; 165-166; 339
[4] Journal of the American Chemical Society, 2007, vol. 129, # 15, p. 4536 - 4537
[5] Heterocycles, 2004, vol. 63, # 3, p. 699 - 706
[6] Angewandte Chemie - International Edition, 2008, vol. 47, # 35, p. 6707 - 6711
[7] Phosphorus, Sulfur and Silicon and Related Elements, 1997, vol. 126, p. 1 - 10
[8] Phosphorus, Sulfur and Silicon and Related Elements, 1998, vol. 140, p. 135 - 145
[9] Journal of Organic Chemistry, 1994, vol. 59, # 23, p. 7085 - 7091
[10] Phosphorus, Sulfur and Silicon and the Related Elements, 1995, vol. 105, # 1-4, p. 205 - 212
[11] Journal of Organic Chemistry, 1990, vol. 55, # 15, p. 4639 - 4642
[12] Justus Liebigs Annalen der Chemie, 1964, vol. 674, p. 1 - 10
[13] Journal of Organic Chemistry, 1990, vol. 55, # 8, p. 2311 - 2317
[14] Synthesis, 1989, # 11, p. 861 - 862
[15] Tetrahedron Letters, 1997, vol. 38, # 10, p. 1797 - 1800
[16] Biochemistry, 2013, vol. 52, # 31, p. 5247 - 5255
[17] Patent: WO2016/210036, 2016, A1, . Location in patent: Page/Page column 178
  • 2
  • [ 401-55-8 ]
  • [ 78-40-0 ]
  • [ 2356-16-3 ]
YieldReaction ConditionsOperation in experiment
92% at 130℃; for 24 h; A mixture of ethyl 2-bromo-2-fluoroacetate (2.5 g, 13.5 mmol) and triethyl phosphate (5.8 mL, 32.8 mmol) was heated at 130°C for 24 hr. The excess of triethyl phosphate was removed by distillation under reduced pressure to afford ethyl 2-(diethoxyphosphoryl)-2-fluoroacetate (473-1) (3.0 g, 92percent yield) as a colorless oil.
Reference: [1] Patent: WO2016/4272, 2016, A1, . Location in patent: Paragraph 00644
  • 3
  • [ 867-13-0 ]
  • [ 2356-16-3 ]
Reference: [1] Journal of Organic Chemistry, 1995, vol. 60, # 15, p. 4730 - 4737
[2] Journal of Fluorine Chemistry, 2005, vol. 126, # 11-12, p. 1467 - 1475
[3] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 8, p. 1051 - 1056
  • 4
  • [ 401-55-8 ]
  • [ 2356-16-3 ]
Reference: [1] Patent: US5180737, 1993, A,
[2] Patent: US5202356, 1993, A,
[3] Patent: US5312814, 1994, A,
[4] Patent: US5114940, 1992, A,
  • 5
  • [ 867-13-0 ]
  • [ 17843-01-5 ]
  • [ 2356-16-3 ]
Reference: [1] Journal of Fluorine Chemistry, 1998, vol. 92, # 1, p. 45 - 52
  • 6
  • [ 541-41-3 ]
  • [ 2356-16-3 ]
Reference: [1] Tetrahedron Letters, 1999, vol. 40, # 14, p. 2681 - 2684
  • 7
  • [ 65094-25-9 ]
  • [ 2356-16-3 ]
Reference: [1] Synthetic Communications, 1994, vol. 24, # 9, p. 1317 - 1322
[2] Phosphorus, Sulfur and Silicon and the Related Elements, 1993, vol. 77, # 1-4, p. 163
  • 8
  • [ 401-58-1 ]
  • [ 122-52-1 ]
  • [ 2356-16-3 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 2000, vol. 65, # 5, p. 772 - 788
  • 9
  • [ 7071-02-5 ]
  • [ 2356-16-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1966, vol. 693, p. 134 - 157
  • 10
  • [ 401-56-9 ]
  • [ 762-04-9 ]
  • [ 2356-16-3 ]
Reference: [1] Journal of Organic Chemistry USSR (English Translation), 1971, vol. 7, p. 241 - 243[2] Zhurnal Organicheskoi Khimii, 1971, vol. 7, p. 249 - 251
  • 11
  • [ 65094-25-9 ]
  • [ 541-41-3 ]
  • [ 2356-16-3 ]
Reference: [1] Tetrahedron, 1997, vol. 53, # 18, p. 6391 - 6400
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