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CAS No.: 369-54-0

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Quality Control of [ 369-54-0 ] Purity: 98% SDS Specification

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Product Details of [ 369-54-0 ]

CAS No. :	369-54-0
Formula :	C₈H₆F₄
M.W :	178.13
SMILES Code :	FC(F)C1=CC=C(C=C1)C(F)F
MDL No. :	MFCD01320708
Boiling Point :	No data available
InChI Key :	VWKMZVCSRVFUGW-UHFFFAOYSA-N
Pubchem ID :	2734031

Safety of [ 369-54-0 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H227-H314
Precautionary Statements:	P501-P240-P210-P233-P243-P241-P242-P264-P280-P370+P378-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P403+P235-P405
Class:	8
UN#:	1760
Packing Group:	Ⅱ

Application In Synthesis of [ 369-54-0 ]

* 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 [ 369-54-0 ]
Downstream synthetic route of [ 369-54-0 ]

[ 369-54-0 ] Synthesis Path-Upstream 1~1

1
[ 369-54-0 ]
[ 651-12-7 ]

References: [1] Journal of Organic Chemistry, 1993, vol. 58, # 7, p. 1827 - 1830.
[2] Russian Journal of Organic Chemistry, 1993, vol. 29, # 10, p. 1663 - 1665[3] Zhurnal Organicheskoi Khimii, 1993, vol. 29, # 10, p. 1999 - 2001.
[4] Tetrahedron, 1964, vol. 20, p. 1625 - 1632.
[5] Journal of Organic Chemistry, 1970, vol. 35, p. 20 - 22.

[ 369-54-0 ] Synthesis Path-Downstream 1~29

1
[ 369-54-0 ]
[ 2629-68-7 ]

Yield	Reaction Conditions	Operation in experiment
99.49%	With chlorine; at 60℃; under 760.051 Torr; for 1.66667h;Irradiation;	EXAMPLE 2 [0039] First, 600.01 g (3.37 mole) of TFPX is added into a glass reactor and stirred evenly by a stirrer. Subsequently, TFPX in the glass reactor is heated to 60 C. by hot water (jacket heating) and irradiated with a mercury-vapor lamp (400 W). [0040] At this time, slightly excessive Cl2 (about 600 g; 8.43 mole) is continuously introduced into the glass reactor so as to perform chlorination. During the reaction the pressure in the glass reactor is kept slightly higher than 1 atm (about 1.01 atm), and the reaction is maintained for 100 minutes to obtain a light yellow liquid. [0041] After the steps as described above, the light yellow liquid is analyzed by GC. According to the results of GC analysis, the formation of CFB is confirmed, and the purity of CFB is 99.49%.
	With chlorine; dibenzoyl peroxide; In tetrachloromethane; at 80℃; for 9h;	Add 50g of <strong>[369-54-0]1,4-bis(difluoromethyl)benzene</strong> to a three-necked flask,500mL of carbon tetrachloride, 7.5g of benzoyl peroxide,After replacing the air, the chlorine gas is blown in,The reaction was stirred at 80 C for 9 h. After TLC monitoring reaction is completed,Nitrogen gas dissolved in the reaction liquid was bubbled in.After the gas exchange is completed, the organic phase is washed with water until neutral.The organic phase is washed with a sodium thiosulfate solution to remove benzoyl peroxide.To the starch potassium iodide test paper does not change color. The organic phase was separated and washed 3 times with water.The organic phase was dried over anhydrous magnesium sulfate. Anhydrous magnesium sulfate was removed by filtration.The solvent was evaporated under reduced pressure to give 103.75 g of colorless oil.Crude product of 1,4-bis(chlorodifluoromethyl)benzene product.

References: [1]Patent: US2013/116482,2013,A1 .Location in patent: Paragraph 0036; 0037; 0038.
[2]Journal of Organic Chemistry,1970,vol. 35,p. 20 - 22.
[3]Patent: CN108658735,2018,A .Location in patent: Paragraph 0029; 0032; 0035; 0038; 0041; 0044; 0047; 0051.

2
[ 369-54-0 ]
[ 1743-00-6 ]

References: [1]Tetrahedron,1964,vol. 20,p. 1625 - 1632.

3
[ 369-54-0 ]
[ 651-12-7 ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 1827 - 1830.
[2]Russian Journal of Organic Chemistry,1993,vol. 29,p. 1663 - 1665.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 1999 - 2001.
[3]Tetrahedron,1964,vol. 20,p. 1625 - 1632.
[4]Journal of Organic Chemistry,1970,vol. 35,p. 20 - 22.

4
[ 369-54-0 ]
[ 2250-36-4 ]

References: [1]Tetrahedron,1964,vol. 20,p. 1625 - 1632.

5
[ 369-54-0 ]
1,1,5-Trifluor-benzocyclobutan [ No CAS ]

References: [1]Tetrahedron,1964,vol. 20,p. 1625 - 1632.

6
[ 7398-82-5 ]
[ 369-54-0 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Chemical Papers,2017,vol. 71,p. 1249 - 1254.
[2]Journal of Fluorine Chemistry,2007,vol. 128,p. 1091 - 1093.
[3]Patent: US2006/211895,2006,A1 .Location in patent: Page/Page column 2.
[4]Patent: US2006/211895,2006,A1 .Location in patent: Page/Page column 2; 3.
[5]Patent: US2006/211895,2006,A1 .Location in patent: Page/Page column 2; 3.
[6]Patent: US2006/211895,2006,A1 .Location in patent: Page/Page column 2; 3.
[7]Patent: US2006/211895,2006,A1 .Location in patent: Page/Page column 2; 3.
[8]Patent: US2006/211895,2006,A1 .Location in patent: Page/Page column 2; 3.

7
[ 106-42-3 ]
3-methyl-phthalic acid-dichloride [ No CAS ]
[ 369-54-0 ]

References: [1]Russian Journal of Organic Chemistry,1993,vol. 29,p. 1663 - 1665.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 1999 - 2001.

8
[ 369-54-0 ]
[ 3345-29-7 ]

References: [1]Russian Journal of Organic Chemistry,1993,vol. 29,p. 1663 - 1665.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 1999 - 2001.
[2]Journal of Organic Chemistry,1993,vol. 58,p. 1827 - 1830.
[3]Journal of Organic Chemistry,1970,vol. 35,p. 20 - 22.

9
[ 369-54-0 ]
[ 2250-30-8 ]

References: [1]Russian Journal of Organic Chemistry,1993,vol. 29,p. 1663 - 1665.
Zhurnal Organicheskoi Khimii,1993,vol. 29,p. 1999 - 2001.

10
[ 369-54-0 ]
dodecafluoro[2,2]paracyclophane [ No CAS ]

References: [1]Journal of Organic Chemistry,1993,vol. 58,p. 1827 - 1830.

11
[ 369-54-0 ]
[ 3200-21-3 ]