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[ CAS No. 7398-82-5 ] {[proInfo.proName]}

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Product Details of [ 7398-82-5 ]

CAS No. :7398-82-5 MDL No. :MFCD00018853
Formula : C8H6Cl4 Boiling Point : -
Linear Structure Formula :- InChI Key :VOWDXSFJQOEFSH-UHFFFAOYSA-N
M.W : 243.95 Pubchem ID :81884
Synonyms :

Calculated chemistry of [ 7398-82-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.25
Num. rotatable bonds : 2
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 55.56
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -4.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.42
Log Po/w (XLOGP3) : 4.15
Log Po/w (WLOGP) : 3.99
Log Po/w (MLOGP) : 4.67
Log Po/w (SILICOS-IT) : 4.44
Consensus Log Po/w : 3.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.2
Solubility : 0.0152 mg/ml ; 0.0000624 mol/l
Class : Moderately soluble
Log S (Ali) : -3.86
Solubility : 0.0339 mg/ml ; 0.000139 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.96
Solubility : 0.00265 mg/ml ; 0.0000109 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 1.21

Safety of [ 7398-82-5 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P305+P351+P338-P310 UN#:3261
Hazard Statements:H302-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 7398-82-5 ]

* 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.

  • Downstream synthetic route of [ 7398-82-5 ]

[ 7398-82-5 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 106-42-3 ]
  • [ 7398-82-5 ]
  • [ 7398-44-9 ]
YieldReaction ConditionsOperation in experiment
With chlorine at 140℃;
  • 2
  • [ 106-42-3 ]
  • [ 7782-50-5 ]
  • [ 7398-82-5 ]
  • [ 7398-44-9 ]
YieldReaction ConditionsOperation in experiment
at 140℃;
  • 3
  • [ 7398-82-5 ]
  • [ 369-54-0 ]
YieldReaction ConditionsOperation in experiment
89% With potassium fluoride; 18-crown-6 ether; tetraphenyl phosphonium chloride; In sulfolane; at 220℃; for 4h;Microwave irradiation;Catalytic behavior; 5 (1 equiv, 5.0 g, 0.02 mol), solvent (15 mL), KF (6 equiv, 7.0 g, 0.12 mol), and phase transfer catalyst (5 mol%) were added in a 50 mL flask equipped with a condenser in the microwave reactor. This mixture was thoroughly stirred and heated to corresponding temperature for 410 h, and the progress of the reaction was monitored by TLC (EtOAc-hexane, 1:5 v/v). Further workup and analysis was carried out as described in conventional heating method.
70% With potassium fluoride;tetraphenyl phosphonium chloride; In sulfolane; at 160℃; for 48h;Product distribution / selectivity; The TFPX is prepared by first grinding KF into fine powder and drying at 160 C. (or grinding industrial-grade KF by a ball mill and drying at 210 C.) and taking 320 grams of KF and 160 grams of TCPX in a 1000 ml glass container ( at a molar ratio of TCPX to KF 1:8). After that, 8 grams of PTC (tetraphenylphosphonium chloride) and 320 grams of sulpholane are added within a nitrogen atmosphere, forming a slurry state. Then, stirring in an oil bath, the slurry is heated to 160 C., such that the reaction is continued for 48 hours (meanwhile the supply of nitrogen can be discontinued). As the reaction comes to an end, the slurry is cooled and cleansed with acetone. After the slurry has been filtered, a TFPX/acetone/sulpholane siltrate and a KCl/KF cake are obtained. Finally acetone, TFPX and sulpholane are separated using segregated distillation, among which the product-TFPX can be obtained at a 70% yield.
57.99 - 69.41% With potassium fluoride;tetraphenylphosphonium bromide; In sulfolane; at 155 - 160℃; for 48h;Product distribution / selectivity; The preferred embodiment of the present invention utilizes slupholane or its derivatives, such as 2,4-dimethylsulpholane, as the solvent, whereas in the comparative examples p-xylene, DPM, DMAC, DMF, NMP and benzonitrile are each utilized as an solvent, in which the comparison of their products, quantity of PTC consumed, conditions of the reactions (temperature and time) and respective yields are organized in a table as shown in Table 1. Refer to Example 1 and Comparative Example 1 as follows for a detailed description of the embodiment.
46.27% With potassium fluoride;tetra-n-butylphosphonium chloride; In sulfolane; at 160 - 165℃; for 48h;Product distribution / selectivity; The preferred embodiment of the present invention utilizes slupholane or its derivatives, such as 2,4-dimethylsulpholane, as the solvent, whereas in the comparative examples p-xylene, DPM, DMAC, DMF, NMP and benzonitrile are each utilized as an solvent, in which the comparison of their products, quantity of PTC consumed, conditions of the reactions (temperature and time) and respective yields are organized in a table as shown in Table 1. Refer to Example 1 and Comparative Example 1 as follows for a detailed description of the embodiment.
40.24% With potassium fluoride;tetraphenylphosphonium bromide; In dimethylsulfolane, 2,4-; at 153 - 173℃; for 48h;Product distribution / selectivity; The preferred embodiment of the present invention utilizes slupholane or its derivatives, such as 2,4-dimethylsulpholane, as the solvent, whereas in the comparative examples p-xylene, DPM, DMAC, DMF, NMP and benzonitrile are each utilized as an solvent, in which the comparison of their products, quantity of PTC consumed, conditions of the reactions (temperature and time) and respective yields are organized in a table as shown in Table 1. Refer to Example 1 and Comparative Example 1 as follows for a detailed description of the embodiment.
20.17% With potassium fluoride;tetraphenylphosphonium bromide; In benzonitrile; at 155 - 160℃; for 77h;Product distribution / selectivity; The preferred embodiment of the present invention utilizes slupholane or its derivatives, such as 2,4-dimethylsulpholane, as the solvent, whereas in the comparative examples p-xylene, DPM, DMAC, DMF, NMP and benzonitrile are each utilized as an solvent, in which the comparison of their products, quantity of PTC consumed, conditions of the reactions (temperature and time) and respective yields are organized in a table as shown in Table 1. Refer to Example 1 and Comparative Example 1 as follows for a detailed description of the embodiment.
4.33% With potassium fluoride;tetraphenylphosphonium bromide; In 1-methyl-pyrrolidin-2-one; at 150 - 155℃; for 71h;Product distribution / selectivity; The preferred embodiment of the present invention utilizes slupholane or its derivatives, such as 2,4-dimethylsulpholane, as the solvent, whereas in the comparative examples p-xylene, DPM, DMAC, DMF, NMP and benzonitrile are each utilized as an solvent, in which the comparison of their products, quantity of PTC consumed, conditions of the reactions (temperature and time) and respective yields are organized in a table as shown in Table 1. Refer to Example 1 and Comparative Example 1 as follows for a detailed description of the embodiment.

  • 4
  • [ 7398-82-5 ]
  • α-chloro, α,α',α'-trifluoro-p-xylene [ No CAS ]
  • [ 369-54-0 ]
YieldReaction ConditionsOperation in experiment
20%; 9.8% With potassium fluoride; at 400℃; for 4h;Neat (no solvent); (No Solvent, No Stirring, 400 C. Reaction Temperature) 95 g (1.6 mole) of KF was placed in a 250 ml conical flask. Under 200 C. and at a reduced pressure, the flask was vacuum and dried for 2 hour until room temperature. Under nitrogen, 50 g 0.2 mole) of α,α,α',α'-tetrachloro-p-xylene was introduced under nitrogen and reacted at 400 C. for 4 hour to obtain 9.8% α,α,α',α'-tetrafluoro-p-xylene. Other products were 20% α-chloro, α,α',α'-trifluoro-p-xylene, and 28% trichloro-p-xylene and 5.9% α,α,α',α'-tetrachloro-p-xylene. When the reacting time increased, the yield of α,α,α',α'-tetrafluoro-p-xylene reduced and decomposed. At 400 C. insoluble solid increased until a white solid was obtained.
With potassium fluoride; at 240℃; for 36h;Neat (no solvent);Product distribution / selectivity; The TFPX is prepared by mixing TCPX with dry KF at a 1:8 ratio respectively in terms of their molar ratio, heating to 240 C. and reacting for 36 hours. After distillation a product is obtained (the peak area % of the product that replaces 14 F obtained from GC analysis yields: 96.04% 4F and 3.86% 3F), and this product is referred to as the first reactant. Then 22.5 grams (0.093 mole) of TCPX and 45 grams (0.77 mole) of dry KF (molar ratio 1:8.3) are mixed and added into the reaction container, along with 1.2 grams (0.011 mole) of phase transfer catalyst (tetramethyl ammonium chloride) and 35 grams of the first reactant (TFPX). Using GC analysis, the peak area % of the mixture prior to the reaction consists 54.4% 4F (TFPX), 2.1% 3F and 43.5% TCPX. Then the mixture is stirred and heated to 190 C. to react for 21 hours; the GC analysis yields the peak area % of the product obtained which replaces 14 F: 79.2% 4F (TFPX), 0% 3F, 2.18% 2F, 1.68% 1F and 16.7% non-reacting TCPX. After 27 hours of reaction time, the peak area % of the product obtained which replaces 14 F yields 80.9% 4F (TFPX), 0% 3F, 2.31% 2F, 1.98% 1F and 14.73% non-reacting TCPX. After 44 hours of reaction time, the peak area % of the product obtained which replaces 14 F yields 82.2% 4F (TFPX), 0% 3F, 3.22% 2F, 2.09% 1F and 11.25% non-reacting TCPX.
  • 5
  • [ 7398-82-5 ]
  • [ 909006-03-7 ]
  • α-chloro, α,α',α'-trifluoro-p-xylene [ No CAS ]
  • [ 369-54-0 ]
YieldReaction ConditionsOperation in experiment
66.4 - 74.8% With potassium fluoride;tetramethlyammonium chloride; tetraphenylphosphonium bromide; at 170 - 190℃; for 5 - 26h;Neat (no solvent);Product distribution / selectivity; 20 grams (0.082 mole) of TCPX and 40 grams (0.69 mole) of dry KF (molar ratio 1:8.4) are mixed along with 40 grams of the first reactant (TFPX) and dual phase transfer catalysts (2 grams (0.018 mole) of tetramethyl ammonium chloride and 2 grams (0.004 mole) of tetraphenylphosphonium bromide) and all added into the reaction container to form a mixture. Then the mixture is stirred and heated up until 190 C. to react for 5 hours; using GC analysis, the peak area % of the product obtained which replaces 14 F yields 94.63% 4F (TFPX), 0% 3F, 5.37% 2F, 0% 1F and 0% TCPX. Followed by cleansing with water, the mixture is extracted with ether, and 51 grams of pure TFPX (b.p 85 C./30 mm) can be obtained through distillation, at an output yield of 74.8%. EXAMPLE 5 Preparation of TFPX-Decrease in Use of PTC 20.5 grams (0.084 mole) of TCPX and 42 grams (0.72 mole) of dry KF (molar ratio 1:8.5) are mixed along with 42 grams of the first reactant (TFPX) and dual phase transfer catalysts with a lower amount than that in Example 4 (2 grams (0.018 mole) of tetramethyl ammonium chloride and 1 grams (0.002 mole) of tetraphenylphosphonium bromide) and all added into the reaction container to form a mixture. The mixture is then stirred and heated to 190 C. to react for 5 hours; using GC analysis, the peak area % of the product obtained which replaces 14 F yields 88.89% 4F (TFPX), 0% 3F, 8.02% 2F, 0% 1F, 0.99% TCPX and 2.1% unidentified products. For 8 hours of reaction time, the peak area % of the product obtained which replaces 14 F yields 90.74% 4F (TFPX), 1.21% 3F, 3.92% 2F, 0% IF, 0% TCPX and 4.1% unidentified products, showing that TCPX has been completely transferred. Having it cleansed with water and extracted with ether, 52 grams of pure TFPX can be obtained through distillation, at an output yield of 66.4%.EXAMPLE 7 Preparation of TFPX-Decrease in Use of Fluorinating Reagent-KF 25 grams (0.102 mole) of TCPX and 38 grams (0.656 mole) of dry KF (molar ratio 1:6.4) are mixed along with 30 grams of TFPX (first reactant) and dual phase transfer catalysts (2.5 grams of tetramethyl ammonium chloride and 1.25 grams of tetraphenylphosphonium bromide) and all added into the reaction container to form a mixture. Then the mixture is stirred and heated to 170 C. to react for 5 hours; using GC analysis, the peak area % of the product obtained which replaces 14 F yields 71.33% 4F (TFPX), 0.64% 3F, 17.77% 2F, 0.71% 1F and 9.54% non-reacting TCPX. The reaction is continued for a further 21 hours, whereafter the peak area % of the product obtained which replaces 14 F yields 91.88% 4F (TFPX), 0.50% 3F, 7.61% 2F, 0% non-reacting TCPX, showing that nearly all the TCPX has been completely transferred.
18.2%; 1.3%; 60% With potassium fluoride;tetraphenyl phosphonium chloride; In xylene; at 20℃; for 48h;Product distribution / selectivity; Xylene was used as solvent, a magnetic stirrer was employed and the reaction was carried out at recycling temperature 47.5 g of KF (0.82 mole) was placed in a 10 ml round conical flask. Under 200 C. and at reduced pressure, the flask was vacuumed and dried for 2 hours. After the flask was cooled to a room temperature, 25 g (0.1 mole) of α,α,α',α'-tetrachloro-p-xylene, under nitrogen, 25 g of xylene and 25 g of tetraphenylphosphonium chloride were introduced into the flask. Under nitrogen, the compositions were stirred and recycling reacted for 2 days. The obtained product was 60% of α,α,α',α'-tetrafluoro-p-xylene, 1.3% of α-chloro, α,α',α'-trifluoro-p-xylene, and 18.2% of α-dichlorod', p-xylene, α-difluoro-p-xylene.
10%; 17%; 54% With potassium fluoride; at 240℃; for 168h;Neat (no solvent);Product distribution / selectivity; (No Solvent, No Stirring, Reaction Temperature 240 C.) 600 g (10.34 mole) of KF was placed in a 2-l conical flask. Under 200 C. and reduced pressure, the flask was vacuum and dried for 2 hour till cold. Under nitrogen condition, 300 g (1.23 mole) of α,α,α',α'-tetrachloro-p-xylene was reacted at 240 C. for 168 hours. 54% of α,α,α',α'-tetrafluoro-p-xylene was obtained. Others were 17% α-chloro, α,α',α'-trifluoro-p-xylene, and 10% α,α-dichloro, α',α'-difluoror-p-xylene. When the reaction time was decreased or increased, the yield of α,α,α',α'-tetrafluoro-p-xylene was reduced. If the reaction temperature was below 200 C., similarly the yield of α,α,α',α'-tetrafluoro-p-xylene was reduced and the unreacted α,α,α',α'-teraafluoro-p-xylene was increased.
With potassium fluoride;tetraphenylphosphonium bromide; at 190℃; for 28h;Neat (no solvent);Product distribution / selectivity; 6.08 grams (0.025 mole) of TCPX and 12 grams (0.206 mole) of dry KF (molar ratio 1:8.2) are mixed and added into the reaction container, along with 1.2 grams (0.011 moles) of phase transfer catalyst (tetraphenylphosphonium bromide) and 10.5 grams of the first reactant (TFPX). Using GC analysis, the peak area % of the mixture prior to the reaction consists 72.02% 4F (TFPX), 1.03% 2F and 26.93% TCPX. Then the mixture is stirred and heated to 190 C. to react for 6 hours, and the peak area % of the product obtained which replaces 14 F yields. 78.01% 4F (TFPX), 0.45% 3F, 12.03% 2F, 0.71% 1F and 8.78% non-reacting TCPX. The reaction is continued for a further 22 hours, whereafter the peak area % of the product obtained which replaces 14 F yields 91.21% 4F (TFPX), 0.62% 3F, 6.28% 2F, 0% 1F and 1.01% non-reacting TCPX.
With potassium fluoride;tetraphenyl phosphonium chloride; In ISOPROPYLAMIDE; at 160 - 165℃; for 47 - 48h;Product distribution / selectivity; The TFPX is prepared by first grinding reagent-grade KF into fine powder and drying at 160 C. (or grinding industrial-grade KF by a ball mill and drying at 210 C.) and taking 10 grams of KF and 5 grams of TCPX in a 250ml glass reaction container (at a molar ratio of TCPX to KF 1:8). After that, 0.5 gram of PTC (tetraphenylphosphonium chloride) and 4.38 grams of DMAC are added within a nitrogen atmosphere, forming a slurry state. Then, stirring in an oil bath, the slurry is heated to 160 C., such that the reaction is continued for 48 hours (meanwhile the supply of nitrogen can be discontinued). As the reaction comes to an end, the product, through GC analysis, is found to comprise 4F (TFPX, tetrafluoro-p-xylene), 3F (trifluoro-p-xylene), 2F (difluoro-p-xylene) and 1F (monofluoro-p-xylene), in which the following structures (5), (6), (7) and (8) present one of the states of 1F, 2F, 3F, and 4F respectively. Within the product, the amounts of 4F, 3F, 2F and 1F are 20, 38, 42 and 0 respectively in terms of their GC area percentages, showing that using DMAC as a solvent to synthesize TFPX will cause products to be mostly retained at intermediates (3F and 2F), while the amount of the finished product (4F) is considerably limited and is difficult to purified by distillation as a result.
With potassium fluoride; at 170℃; for 22h;Neat (no solvent);Product distribution / selectivity; 6.0 grams (0.025 mole) of TCPX and 12 grams (0.206 mole) of dry KF (molar ratio 1:8) are mixed in the reaction container, and 10 grams of the first reactant (crude TFPX) and dual phase transfer catalysts (0.3 gram of tetra n-butylammonium iodide and 0.3 gram of tetra n-butylphosphonium chloride) are also added in. Prior to reaction, GC analysis consists the peak area % as 72.11% 4F (TFPX), 0.36% 3F, 1.03 2F, 0.25% 1F and 26.23% TCPX. After mixture is stirred and heated to 170 C. to react for 5 hours, and the peak area % yields: 86.84% 4F (TFPX), 0.86% 3F, 7.32% 2F, 0.52% 1F and 4.44% TCPX. The reaction is continued for a further 24 hours, whereafter the peak area % yields 95.04% 4F (TFPX), 2.84% 3F, 0.39% 2F, 0% 1F, 0.16% non-reacting TCPX, and approximately 1.5% unidentified products.

  • 6
  • [ 7398-82-5 ]
  • [ 909006-03-7 ]
  • α-fluoro, α,α',α'-trichloro-p-xylene [ No CAS ]
  • α-chloro, α,α',α'-trifluoro-p-xylene [ No CAS ]
  • [ 369-54-0 ]
YieldReaction ConditionsOperation in experiment
27.3%; 6.6%; 28.1%; 18.3% With potassium fluoride; at 350℃; for 12h;Neat (no solvent); (No Solvent, No Stirring, 350 C. Reaction Temperature) 95 g (1.6 mole) of KF was placed in a 250 ml conical flask. Under 200 C. and at a reduced pressure, the flask was vacuum and dried for 2 hour until room temperature. Under nitrogen, 50 g (0.2 mole) of α,α,α',α'-tetrachloro-p-xylene was introduced under nitrogen and reacted at 350 C. for 12 hour to obtain 18.3% α,α,α',α'-tetrafluoro-p-xylene. Other products were 28.1% α-chloro, α,α',α'-trifluoro-p-xylene, and 28% trichloro-p-xylene and 5.9% α,α,α',α'-tetrachloro-p-xylene and 27.3% α,α-dichloro, α',α'-difluoro-p-xylene, 6.6% α-fluoro, α,α',α'-trichloro-p-xylene and 1% α,α,α',α'-tetrachloro-p-xylene. When the reacting time increased, the yield of α,α,α',α'-tetrafluoro-p-xylene reduced and decomposed. At 350 C. insoluble solid increased until a white solid was obtained
With potassium fluoride;tetra-(n-butyl)ammonium iodide; at 170℃; for 29h;Neat (no solvent);Product distribution / selectivity; 6.03 grams (0.025 mole) of TCPX and 12.3 grams (0.21 mole) of dry KF (molar ratio 1:8.4) are mixed and added into the reaction container, along with the first reactant (crude TFPX) and phase transfer catalyst (0.3 gram of tetra n-butylammonium iodide). Before the reaction takes place, using GC analysis the peak area % of this mixture consists 73.17% 4F (TFPX), 0.38% 3F, 1.05 2F, 0.29% 1F and 24.53% TCPX. After mixture is stirred and heated to 170 C. to react for 5 hours, and the peak area % yields 79.78% 4F (TFPX), 0.32% 3F, 1.82% 2F, 1,08% 1F and 16.19% non-reacting TCPX. Reaction time is continued for a further 24 hours, whereafter the peak area % yields 83.53% 4F (TFPX), 0.33% 3F, 1.82% 2F, 1.57% 1F, 11.26% non-reacting TCPX, and approximately 1.5% other unidentified products.
With potassium fluoride;tetra-(n-butyl)ammonium iodide; tetra-n-butylphosphonium chloride; at 170℃; for 29h;Neat (no solvent);Product distribution / selectivity; 6.0 grams (0.025 mole) of TCPX and 12 grams (0.206 mole) of dry KF (molar ratio 1:8) are mixed in the reaction container, and 10 grams of the first reactant (crude TFPX) and dual phase transfer catalysts (0.3 gram of tetra n-butylammonium iodide and 0.3 gram of tetra n-butylphosphonium chloride) are also added in. Prior to reaction, GC analysis consists the peak area % as 72.11% 4F (TFPX), 0.36% 3F, 1.03 2F, 0.25% 1F and 26.23% TCPX. After mixture is stirred and heated to 170 C. to react for 5 hours, and the peak area % yields: 86.84% 4F (TFPX), 0.86% 3F, 7.32% 2F, 0.52% 1F and 4.44% TCPX. The reaction is continued for a further 24 hours, whereafter the peak area % yields 95.04% 4F (TFPX), 2.84% 3F, 0.39% 2F, 0% 1F, 0.16% non-reacting TCPX, and approximately 1.5% unidentified products.
With potassium fluoride; at 240℃; for 36h;Neat (no solvent);Product distribution / selectivity; 6.0 grams (0.025 mole) of TCPX and 12 grams (0.206 mole) of dry KF (molar ratio 1:8) are mixed in the reaction container, and 10 grams of the first reactant (crude TFPX) and dual phase transfer catalysts (0.3 gram of tetra n-butylammonium iodide and 0.3 gram of tetra n-butylphosphonium chloride) are also added in. Prior to reaction, GC analysis consists the peak area % as 72.11% 4F (TFPX), 0.36% 3F, 1.03 2F, 0.25% 1F and 26.23% TCPX. After mixture is stirred and heated to 170 C. to react for 5 hours, and the peak area % yields: 86.84% 4F (TFPX), 0.86% 3F, 7.32% 2F, 0.52% 1F and 4.44% TCPX. The reaction is continued for a further 24 hours, whereafter the peak area % yields 95.04% 4F (TFPX), 2.84% 3F, 0.39% 2F, 0% 1F, 0.16% non-reacting TCPX, and approximately 1.5% unidentified products.

  • 7
  • [ 7398-82-5 ]
  • α-fluoro, α,α',α'-trichloro-p-xylene [ No CAS ]
  • α-chloro, α,α',α'-trifluoro-p-xylene [ No CAS ]
  • [ 369-54-0 ]
YieldReaction ConditionsOperation in experiment
1.3%; 31.9%; 36.6% With potassium fluoride; at 300℃; for 24h;Neat (no solvent); (No Solvent, No Stirring, Reaction Temperature 300 C.) 95 g (1.6 mole) of KF was placed in a 250 ml conical flask. Under 200 C. and at a reduced pressure, the flask was vacuum and dried for 2 hour until room temperature. Under nitrogen, 50 g 0.2 mole) of α,α,α',α'-tetrachloro-p-xylene was introduced under nitrogen and reacted at 300 C. for 24 hours to obtain 36.6% α,α,α',α'-tetrafluoro-p-xylene. Other products were 31.9% α-chloro, α,α',α'-trifluoro-p-xylene, and 9.7% trichloro-p-xylene and 1.3% α-fluoro, (α,α',α'-trichloro-p-xylene. When the reacting time increased, the yield of α,α,α',α'-tetrafluoro-p-xylene reduced and decomposed. At 300 C. insoluble solid increased until a white solid was obtained.
  • 8
  • α-chloro, α,α',α'-trifluoro-p-xylene [ No CAS ]
  • [ 7398-82-5 ]
  • [ 909006-03-7 ]
  • α-fluoro, α,α',α'-trichloro-p-xylene [ No CAS ]
  • [ 369-54-0 ]
YieldReaction ConditionsOperation in experiment
With potassium fluoride;tetramethlyammonium chloride; at 190℃; for 44h;Neat (no solvent);Product distribution / selectivity; The TFPX is prepared by mixing TCPX with dry KF at a 1:8 ratio respectively in terms of their molar ratio, heating to 240 C. and reacting for 36 hours. After distillation a product is obtained (the peak area % of the product that replaces 14 F obtained from GC analysis yields: 96.04% 4F and 3.86% 3F), and this product is referred to as the first reactant. Then 22.5 grams (0.093 mole) of TCPX and 45 grams (0.77 mole) of dry KF (molar ratio 1:8.3) are mixed and added into the reaction container, along with 1.2 grams (0.011 mole) of phase transfer catalyst (tetramethyl ammonium chloride) and 35 grams of the first reactant (TFPX). Using GC analysis, the peak area % of the mixture prior to the reaction consists 54.4% 4F (TFPX), 2.1% 3F and 43.5% TCPX. Then the mixture is stirred and heated to 190 C. to react for 21 hours; the GC analysis yields the peak area % of the product obtained which replaces 14 F: 79.2% 4F (TFPX), 0% 3F, 2.18% 2F, 1.68% 1F and 16.7% non-reacting TCPX. After 27 hours of reaction time, the peak area % of the product obtained which replaces 14 F yields 80.9% 4F (TFPX), 0% 3F, 2.31% 2F, 1.98% 1F and 14.73% non-reacting TCPX. After 44 hours of reaction time, the peak area % of the product obtained which replaces 14 F yields 82.2% 4F (TFPX), 0% 3F, 3.22% 2F, 2.09% 1F and 11.25% non-reacting TCPX.
  • 9
  • [ 7398-82-5 ]
  • [ 7398-44-9 ]
  • [ 104-82-5 ]
  • [ 623-25-6 ]
  • [ 623-27-8 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; nitric acid In para-xylene 10 EXAMPLE 10 EXAMPLE 10 Charged into the same reactor as used in Example 1 were 88.0 g of chloroxylene mixture with a composition of 10.2% by weight (9.0 g, 0.05 mol) of α,α'-dichloro-p-xylene, 47.7% by weight (42.0 g, 0.2 mol) of α,α,α'-trichloro-p-xylene and 42.1% by weight (37.0 g, 0.15 mol) of α,α,α',α'-tetrachloro-p-xylene, 1700 g of aqueous solution containing 3% by weight of nitric acid and 3% by weight of hydrogen chloride and 3 ml of p-xylene and the temperature of this mixture was enhanced by heating with stirring to cause the reaction under refluxed condition for 7 hours. By treating likewise as in Example 1 after the reaction was complete there were obtained 43.3 g of terephthalaldehyde and 8.6 g of carboxylic acid as by-product.
  • 10
  • ammonium vanadate [ No CAS ]
  • [ 7398-82-5 ]
  • [ 7398-44-9 ]
  • [ 104-82-5 ]
  • [ 623-25-6 ]
  • [ 623-27-8 ]
YieldReaction ConditionsOperation in experiment
With nitric acid In para-xylene 9 EXAMPLE 9 EXAMPLE 9 Charged into the same reactor as used in Example 1 were 84.5 g of chloroxylene mixture with a composition of 20.7% by weight (17.5 g, 0.1 mol) of α,α'-dichloro-p-xylene, 49.7% by weight (42.0 g, 0.2 mol) of α,α,α'-trichloro-p-xylene and 29.6% by weight (25.0 g, 0.10 mol) of α,α,α',α'-tetrachloro-p-xylene, 1700 g of 3% by weight of nitric acid, 3.0 g of ammonium metavanadate and 3 ml of p-xylene. The temperature of this mixture was enhanced by heating with stirring to cause the reaction under refluxed condition for 9 hours. By treating likewise as in Example 1 after the reaction was complete there were obtained 46.9 g of terephthalaldehyde and 6.3 g of carboxylic acid as by-product.
  • 11
  • [ 106-42-3 ]
  • [ 7398-82-5 ]
  • [ 23063-36-7 ]
  • [ 7398-44-9 ]
  • [ 104-82-5 ]
  • [ 623-25-6 ]
YieldReaction ConditionsOperation in experiment
With chlorine at 138 - 205℃; for 11.5h; Photolysis;
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