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[ CAS No. 1583-59-1 ] {[proInfo.proName]}

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Chemical Structure| 1583-59-1
Chemical Structure| 1583-59-1
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Product Details of [ 1583-59-1 ]

CAS No. :1583-59-1 MDL No. :MFCD00236217
Formula : C7H4F2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :DGCOGZQDAXUUBY-UHFFFAOYSA-N
M.W :158.10 Pubchem ID :74103
Synonyms :

Calculated chemistry of [ 1583-59-1 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 0
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 32.65
TPSA : 18.46 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) : -5.49 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.97
Log Po/w (XLOGP3) : 2.5
Log Po/w (WLOGP) : 2.85
Log Po/w (MLOGP) : 1.49
Log Po/w (SILICOS-IT) : 2.32
Consensus Log Po/w : 2.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.8
Solubility : 0.251 mg/ml ; 0.00159 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.463 mg/ml ; 0.00293 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.327 mg/ml ; 0.00207 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.24

Safety of [ 1583-59-1 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P305+P351+P338 UN#:
Hazard Statements:H315-H317-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 1583-59-1 ]

* 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 [ 1583-59-1 ]
  • Downstream synthetic route of [ 1583-59-1 ]

[ 1583-59-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 274-09-9 ]
  • [ 1583-59-1 ]
YieldReaction ConditionsOperation in experiment
90% With fluorine; trifluoroacetic acid In acetonitrile at -20℃; Inert atmosphere; Flow reactor Weigh 100g Benzodioxole, 900g acetonitrile, mix and prepare Benzodioxole acetonitrile solution with a mass fraction of 10percent, again add 1g of trifluoroacetic acid and mix for use. The flow rate of fluorine gas and nitrogen gas is adjusted to prepare a fluorine gas nitrogen mixed gas with a mass fraction of 10percent, which is ready for use. Using the reaction process shown in Figure 1, a microchannel reactor made of silicon carbide is used.The liquid holding capacity of each module is 1ml, and the reaction temperature of the module is set to -20 °C.Control the pumping rate to adjust the reaction residence time,Set the dwell time to 20s,The A module was continuously pumped in a 10percent mass fraction of Benzodioxole acetonitrile solution (containing 1percent trifluoroacetic acid) for pre-cooling.At the same time, the B module continuously and uniformly passes a fluorine gas mixed gas with a mass fraction of 10percent.The molar amount of fluorine gas is 2.2 times that of the Benzodioxole, and the reaction is mixed in the CDEF module.Enter the gas-liquid separator, the gas is treated and discharged, and the liquid is collected.The liquid was subjected to water washing and distillation to obtain a product of 1,3-benzodioxole-2,2-difluoro in a yield of 90percent and a content of 99percent.
Reference: [1] Patent: CN108383825, 2018, A, . Location in patent: Paragraph 0020-0039; 0044-0047
  • 2
  • [ 2032-75-9 ]
  • [ 1583-59-1 ]
YieldReaction ConditionsOperation in experiment
28.8 g for 2 h; 24 ml (0.2 mol) of a pepper ring was added to a 250 ml lined PTFE stainless steel flask,Phosphonium chloride 97.6g and phosphorus pentachloride 83.3g (0.4m0l), the temperature rose to reflux reaction, GC detection of raw material pepper ring content of less than 0.2percent reaction end; the reaction solution distillation distillation distillation of by-product three Phosphorus chloride and solvent phosphorus oxychloride, vacuum distillation temperature of 110 ° C, vacuum degree of -0.095MPa; vacuum distillation after the end of cooling to 4 ° C, in the vacuum of -0.095MPa drop Plus hydrogen fluoride liquid 8g (0.4mol), dropping finished, incubated for 2 hours, and then release the by-product of hydrogen chloride, and then add saturated sodium carbonate solution, adjust the solution PH value of 6.5 ~ 7.5, stirring 0.5 hours, , The organic layer was distilled after the colorless transparent liquid for the finished 2,2 - difluoro - 1, 3 - benzodiazepine 28.8g, yield 99.8percent, GC purity 99.8percent
Reference: [1] Journal of Fluorine Chemistry, 2006, vol. 127, # 1, p. 85 - 90
[2] Patent: EP1502908, 2005, A1, . Location in patent: Page 4
[3] Patent: EP1502908, 2005, A1, . Location in patent: Page 4
[4] Patent: CN106810530, 2017, A, . Location in patent: Paragraph 0008; 0011
  • 3
  • [ 75-61-6 ]
  • [ 120-80-9 ]
  • [ 1583-59-1 ]
YieldReaction ConditionsOperation in experiment
63 g With tetra-(n-butyl)ammonium iodide; potassium carbonate In 1-methyl-pyrrolidin-2-one at 100℃; for 8 h; Autoclave (1) In a 1000 mL autoclave,55.0 g (0.5 mol) of catechol,Potassium carbonate 85.0 g (0.62 mol),NMP (N-methylpyrrolidone) 200ml,0.5 g of tetrabutylammonium iodide and 157 g (0.75 mol) of dibromodifluoromethane were added to the reaction vessel.Warming up to 100 ° C,Reaction 8h,After cooling to room temperature, pour the reaction solution into 500 ml of crushed ice.Stir until the ice is completely dissolved,Let stand for liquid separation,Remove the water phase,The organic phase was dried by adding 10 g of anhydrous sodium sulfate.Obtaining crude 2,2-difluorobenzo-1,3 dioxolane,Re-distillation,Obtaining a fine 2,2-difluorobenzo-1,3 dioxol 63g (0.4 mol);
Reference: [1] Patent: CN103497180, 2016, B, . Location in patent: Paragraph 0045; 0055-0056; 0067; 0074; 0086-0087
  • 4
  • [ 2032-75-9 ]
  • [ 17455-13-9 ]
  • [ 1583-59-1 ]
Reference: [1] Patent: US4895871, 1990, A,
  • 5
  • [ 1583-59-1 ]
  • [ 656-46-2 ]
YieldReaction ConditionsOperation in experiment
40.7%
Stage #1: at 0 - 15℃; for 18.5 h;
Stage #2: at 50℃; for 6 h;
Stage #3: With sulfuric acid In water
Example 2; 2,2-Difluorobenzo-1,3-dioxole-5-carboxylic acid; 1012 g of HF were initially charged at 0° C. and 257 g of BF3 were injected within 60 min. Subsequently, 1000 g of difluorobenzodioxole were added within 60 minutes and the temperature was raised to 15° C. within 30 min. Subsequently, the mixture was stirred at 15° C. for a further 16 hours. Subsequently, 773 g of HF were distilled off at standard pressure up to internal temperature 55° C. 5 l of 10percent KOH solution were initially charged and the residue of the distillation was added dropwise with cooling. On completion of addition, the mixture was stirred at 50° C. for a further 6 h, in the course of which the pH was kept between 10 and 11 by adding KOH. Subsequently, the mixture was cooled, the precipitate was filtered off with suction and the mother liquor was adjusted to pH 5 using sulphuric acid. After filtration with suction and drying, 529 g of beige solid were obtained. Yield: 40.7percent {circumflex over (=)}81.4percent based on difluorobenzodioxole. 1H NMR (400 MHz, DMSO-D6): 13.52 (b, 1 H), 7.87 (m, 2 H), 7.53 (d, 1H)
Reference: [1] Patent: EP1595876, 2005, A1, . Location in patent: Page/Page column 5
[2] Patent: US2005/277692, 2005, A1, . Location in patent: Page/Page column 3
  • 6
  • [ 1583-59-1 ]
  • [ 33070-32-5 ]
YieldReaction ConditionsOperation in experiment
80% With bromine In water at 25 - 85℃; for 9 h; Reflux 2, 2-difluoro-l, 3-benzodioxole (200g, 1.27mol) and water (456g, 25.3mol) were placed in a 1000 mL round -bottomed flask fitted with a mechanical stirrer, reflux condenser and pressure equalizing addition funnel. Bromine (284g, 1.77mol) was added drop-wise at 25°C for one hour. During addition, the temperature of the mass was raised from 25°C to 85°C. The temperature of the reaction mass was maintained at 85°C for 8 hours. The progress of the reaction was monitored by liquid chromatography. The temperature of the reaction mass was brought down to 25°C. The layers were separated, the organic layer was washed with sodium bisulphite solution followed by sodium bicarbonate solutionto obtain the title compound. The crude mass was purified by vacuum distillation. Yield (percent) : 80 Purity (percent) : 99.8 (by liquid chromatography)
538 g at 10 - 70℃; Example 1Process of preparation of 5-bromo-2,2-difluoro-1,3-benzodioxole
A mixture of 2,2-difluoro-l ,3-benzodioxote (560 g) and Hydrogen bromide(l 100 g, Assay 47percent) were taken in a reaction vessel fitted with cold condenser. The reaction mixture was cooled to 10°C and 30 percent Hydrogen Peroxide solution (806 g) was added slowly in lot wise. Upon completion of addition, the temperature of the reaction mixture was cautiously raised to 70°C. The organic layer was separated and washed with 20 percent of sodium metabisulfite and then washed with 20percent of potassium bicarbonate solution. The organic layer was dried over magnesium sulfate and filtered. The filtrate was distilled under high vacuum to obtain the title compound.
Yield: 538 g
Reference: [1] Patent: WO2017/46816, 2017, A2, . Location in patent: Page/Page column 9-10
[2] Patent: EP1595877, 2005, A1, . Location in patent: Page/Page column 4
[3] European Journal of Organic Chemistry, 2004, # 1, p. 64 - 68
[4] Patent: WO2016/38627, 2016, A1, . Location in patent: Page/Page column 4
  • 7
  • [ 1583-59-1 ]
  • [ 7439-89-6 ]
  • [ 33070-32-5 ]
Reference: [1] Patent: US5633218, 1997, A,
[2] Patent: US4895871, 1990, A,
  • 8
  • [ 1583-59-1 ]
  • [ 106876-54-4 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 452 - 462
[2] European Journal of Organic Chemistry, 2003, # 3, p. 452 - 462
  • 9
  • [ 1583-59-1 ]
  • [ 531508-54-0 ]
Reference: [1] European Journal of Organic Chemistry, 2003, # 3, p. 452 - 462
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