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Chemical Structure| 65094-22-6
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Product Details of [ 65094-22-6 ]

CAS No. :65094-22-6 MDL No. :MFCD00069118
Formula : C5H10BrF2O3P Boiling Point : -
Linear Structure Formula :(C2H5O)2P(O)CF2Br InChI Key :QRADKVYIJIAENZ-UHFFFAOYSA-N
M.W : 267.01 Pubchem ID :144101
Synonyms :

Calculated chemistry of [ 65094-22-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 0
Fraction Csp3 : 1.0
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 44.99
TPSA : 45.34 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) : -6.63 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.3
Log Po/w (XLOGP3) : 1.83
Log Po/w (WLOGP) : 4.04
Log Po/w (MLOGP) : 1.32
Log Po/w (SILICOS-IT) : 1.28
Consensus Log Po/w : 2.15

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.32
Solubility : 1.28 mg/ml ; 0.0048 mol/l
Class : Soluble
Log S (Ali) : -2.4
Solubility : 1.06 mg/ml ; 0.00396 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.42
Solubility : 1.01 mg/ml ; 0.00377 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.53

Safety of [ 65094-22-6 ]

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 [ 65094-22-6 ]

* 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 [ 65094-22-6 ]
  • Downstream synthetic route of [ 65094-22-6 ]

[ 65094-22-6 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 65094-22-6 ]
  • [ 139-02-6 ]
  • [ 458-92-4 ]
YieldReaction ConditionsOperation in experiment
46 %Spectr. Cooling with ice Sodium hydroxide (0.4 g, 0.01 mol) and phenol (0.94 g, 0.01 mol) were added to anhydrous methanol. After completesolution had occurred, the solution was cooled in an ice bath and 4 (2.67 g, 0.01 mol) was added dropwise by syringe. PhCF3 (0.58 g, 0.004 mol) was added and 19F spectral analysis showed that the solution contained a mixture of CH3OCF2H (46percent) and PhOCF2H= (11percent) [19F NMR (CDCl3) (ppm): δ = -80.9 (d, 2JHF = 75 Hz) [Lit [51]:2JHF = 73.9 Hz]].
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828
  • 2
  • [ 65094-22-6 ]
  • [ 108-95-2 ]
  • [ 458-92-4 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 27, p. 5278 - 5283
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 2, p. 797 - 804
  • 3
  • [ 75-61-6 ]
  • [ 122-52-1 ]
  • [ 65094-22-6 ]
YieldReaction ConditionsOperation in experiment
96% for 20 h; Heating / reflux EXAMPLE 4
Synthesis of Diethyl(bromodifluoromethyl)phosphonate
Dibromodifluoromethane (209.8 g, 1 mol) is added to a magnetically stirred solution of triethyl phosphite (153.5 g, 0.925 mol) in anhydrous ether (450 ml) under a nitrogen atmosphere.
After the addition, the reaction is allowed to warm to room temperature before being refluxed for 20 hours.
The volatiles are removed in vacuo, and the product is purified by distillation (b.pt. 50-52° C., 1 mm/Hg) to yield diethyl(bromodifluoromethyl) phosphonate as a colorless liquid (256.3 g, 96percent); 1H NMR (CDCl3): 4.35 (m, 4H), 1.35 (m, 6H).
13C NMR (CDCl3): 122.9, 119.8, 118.6, 115.4, 114.2, 111.1, 66.59, 66.50, 16.56, 16.48.
95% for 24 h; Inert atmosphere; Reflux General procedure: A three-neck 1 l flask, fitted with a septum, stir bar, and a water condenser with a nitrogen inlet, was cooled in an ice bath. Dry ether (300 ml) and 99 g (0.6 mol) of triethylphosphite was added to the cooled flask, followed by addition (via syringe) of 134 g (0.64 mol) of dibromodifluoromethane 1. The ice bath was removed and the reaction mixture refluxed for 24 h, followed by removal of the ether, excess 1 and ethyl bromide via rotary evaporation at reduced pressure. The remaining clear liquid was distilled under vacuum through a 6-in. Vigreaux column to give 150 g (95percent) of diethyl bromodifluoromethylphosphonate (bp 99-102 °C/16 mm Hg). 19F NMR(CDCl3) (ppm): δ = -61.9 (d, 2JPF = 92 Hz); 31P NMR (CDCl3) (ppm): δ = -1.2 (t, 2JPF = 93 Hz); 13C NMR (CDCl3) (ppm): δ = 116.8 (td, 1JCF = 330 Hz, 1JCP = 238 Hz), d = 66.3 (2JCP = 7.4 Hz), d = 16.4 (d, 3JCP = 5.88 Hz); 1H NMR (CDCl3)(ppm): δ = 4.41 (qd, 3JHH = 7.0 Hz, 3JHP = 8.5 Hz), d = 1.42 (t, 3JHH = 7.0 Hz). GC-MS, m/z (relative intensity): 268 (0.2), 266 (0.2), 137 (83), 109 (100), 93 (35), 91 (27), 81 (86), 65 (41), 29 (66): IR (P=O) 1285 cm-1: Anal. Calcd. for C5H10O3PCF2Br: C, 22.47percent; H,3.75percent. Found C, 22.34percent; H, 3.80percent.
93% at 4 - 20℃; Heating / reflux Diethyl (bromodifluoromethyl)phosphonate (C): A solution of triethyl phosphite (95.50 g, 575 mmol) in 300 mL of anhydrous diethyl ether was cooled, EPO <DP n="66"/>under a nitrogen atmosphere, to 4 0C before addition of dibromodifluoromethane (144.72 g, 690 mmol). The mixture was allowed to warm to room temperature and stirred overnight, then heated to reflux for 24 hours. Ether was removed by rotary evaporation, and the resultant liquid was distilled to afford 142.75 g (93percent) of a clear colorless liquid: bp 144-145 0C (25 mmHg) [ lit. bp 97-98 0C (19 mmHg) (This material is commercially available from Lancaster and Aldrich).
Reference: [1] Journal of Organometallic Chemistry, 1997, vol. 529, # 1-2, p. 267 - 278
[2] Phosphorus, Sulfur and Silicon and Related Elements, 1997, vol. 122, p. 247 - 259
[3] Patent: US2004/225146, 2004, A1, . Location in patent: Page 4
[4] Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828
[5] Patent: WO2006/78698, 2006, A1, . Location in patent: Page/Page column 64-65
[6] Journal of Organic Chemistry, 1986, vol. 51, # 25, p. 4768 - 4779
[7] Tetrahedron Letters, 1989, vol. 30, # 50, p. 7013 - 7016
[8] Journal of Fluorine Chemistry, 1989, vol. 44, p. 275 - 284
[9] Journal of Fluorine Chemistry, 2007, vol. 128, # 3, p. 174 - 178
[10] Patent: JP5664635, 2015, B2, . Location in patent: Paragraph 0128; 0129
  • 4
  • [ 353-59-3 ]
  • [ 122-52-1 ]
  • [ 65094-22-6 ]
YieldReaction ConditionsOperation in experiment
20% at 120℃; for 240 h; Autoclave General procedure: Triethyl phosphite (10.4 g, 0.06 mol) and CFCl3 (10.3 g, 0.075 mol) were placed into a 128 ml Hastelloy C autoclave equipped with a glass liner and magnetic stir bar. The autoclave was sealed and heated to 120 °C for 10 days during which time the pressure in the autoclave remained nearly constant at 59 psig.After cooling, the autoclave was opened and the residue concentrated on a steam bath and distilled under vacuum. After distillation of the unreacted triethyl phosphite, a distillate fraction was obtained (bp = 96-99 °C/8 mm Hg) which contained 15 in approximately 30percent yield. Diethyl ethylphosphonate, diethyl phosphite and triethyl phosphate were also identified as contaminants by NMR spectral data. 19F NMR (CDCl3) (ppm): δ = -73.4 (d, 2JPF = 88 Hz); 31P NMR (CDCl3) (ppm): δ = 2.4 (d, 2JPF = 88 Hz); 13C NMR (CDCl3) (ppm): δ = 113.4 (dd, 1JCF = 316 Hz, 1JCP = 222 Hz), d = 66.6 (d, 2JCP = 7.3 Hz), d = 16.4 (d, 3JCP = 4.4 Hz); 1H NMR (CDCl3) (ppm): δ = 4.40 (apparent pentet, J = 7.0 Hz), d = 1.42 (t, 3JHH = 7.0 Hz),: IR (P=O) 1277 cm-1.
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828
  • 5
  • [ 180627-08-1 ]
  • [ 65094-22-6 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 18, p. 6401 - 6403
  • 6
  • [ 753-66-2 ]
  • [ 122-52-1 ]
  • [ 65094-22-6 ]
  • [ 80077-69-6 ]
Reference: [1] Journal of Fluorine Chemistry, 2011, vol. 132, # 10, p. 815 - 828
  • 7
  • [ 58201-66-4 ]
  • [ 122-52-1 ]
  • [ 65094-22-6 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3616 - 3618
  • 8
  • [ 58201-66-4 ]
  • [ 122-52-1 ]
  • [ 65094-22-6 ]
  • [ 603-35-0 ]
Reference: [1] Journal of Fluorine Chemistry, 2008, vol. 129, # 7, p. 583 - 589
  • 9
  • [ 80084-30-6 ]
  • [ 65094-22-6 ]
Reference: [1] Journal of Fluorine Chemistry, 1981, vol. 18, p. 197 - 202
  • 10
  • [ 82845-20-3 ]
  • [ 65094-22-6 ]
Reference: [1] Chemistry Letters, 1982, p. 755 - 758
  • 11
  • [ 58201-66-4 ]
  • [ 122-52-1 ]
  • [ 74-96-4 ]
  • [ 65094-22-6 ]
  • [ 603-35-0 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 20, p. 3616 - 3618
  • 12
  • [ 75-44-5 ]
  • [ 82845-20-3 ]
  • [ 1478-53-1 ]
  • [ 65094-22-6 ]
  • [ 113161-60-7 ]
  • [ 97480-49-4 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 7, p. 1523 - 1527
  • 13
  • [ 65094-22-6 ]
  • [ 135-19-3 ]
  • [ 712-79-8 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 27, p. 5278 - 5283
  • 14
  • [ 65094-22-6 ]
  • [ 123-08-0 ]
  • [ 73960-07-3 ]
YieldReaction ConditionsOperation in experiment
72% With potassium hydroxide In water; acetonitrile at -78 - 20℃; for 0.333333 h; 4-Hydroxybenzaldehyde (1.00 g, 8.20 mmol),KOH (9.20 g, 164 mmol),CH3CN-H2O (50 mL, 1: 1) into a sealed tube,Diethyl bromofluoromethylphosphonate (3 mL, 16.40 mmol) was slowly added dropwise at -78 ° C,Then warmed to room temperature,After 20 min of reaction at room temperature,TLC detection reaction was completed,Saturated NaHCO3 solution was added,Extraction with ethyl acetate,The combined organic phase,Dried over anhydrous Na2SO4,filter,concentrate,Column chromatography (EA: PE = 1: 70),1.01 g of solid are obtained,Yield 72percent.
Reference: [1] Patent: CN107365248, 2017, A, . Location in patent: Paragraph 0027; 0028
  • 15
  • [ 65094-22-6 ]
  • [ 121-71-1 ]
  • [ 101975-23-9 ]
Reference: [1] Patent: EP2927218, 2015, A1, . Location in patent: Paragraph 0849
  • 16
  • [ 2075-46-9 ]
  • [ 65094-22-6 ]
  • [ 956477-64-8 ]
YieldReaction ConditionsOperation in experiment
68% With potassium fluoride In acetonitrile at 20℃; for 12 h; Schlenk technique; Inert atmosphere; Green chemistry General procedure: To a 25 mL of Schlenk tube equipped with a Teflon septum were added Imidazoles/Pyrazoles (0.4 mmol, 1.0 equiv) and KF (46.4 mg, 2.0 equiv) under Ar, followed by MeCN (3 mL) with stirring. 2 (0.40 mmol, 1.0 equiv) were added subsequently. After stirring for 12 h, the reaction mixture was concentrated. The residue was purified with silica gel chromatography to provide pure product.
Reference: [1] Tetrahedron Letters, 2018, vol. 59, # 28, p. 2752 - 2754
  • 17
  • [ 65094-22-6 ]
  • [ 695-96-5 ]
  • [ 1214348-81-8 ]
Reference: [1] Patent: WO2017/74832, 2017, A1, . Location in patent: Page/Page column 58-59
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