CN101012184A - Fluorine-containing cyclopropane and synthetic method thereof - Google Patents

Fluorine-containing cyclopropane and synthetic method thereof Download PDF

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CN101012184A
CN101012184A CN 200710037411 CN200710037411A CN101012184A CN 101012184 A CN101012184 A CN 101012184A CN 200710037411 CN200710037411 CN 200710037411 CN 200710037411 A CN200710037411 A CN 200710037411A CN 101012184 A CN101012184 A CN 101012184A
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fluorine
trifluoromethyl
cyclopropane
phenyl
salt
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曹卫国
钱嘉贤
张慧
陈杰
姜海燕
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University of Shanghai for Science and Technology
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Abstract

The invention discloses a fluorine cyclopropane and synthesizing method with structure as right formula (X is -CN and -C (O) OCH3; R is as right lower formula), which comprises the following steps: adopting dichloromethane as solvent; mixing p-trifluoromethyl phenyl ethylene derivant, arsenide and potassium carbonate with molar rate at 1:1.1-2.5:3-5; stirring under indoor temperature until TLC traces p-trifluoromethyl phenyl ethylene derivant in the reacting system; removing solvent; separating; obtaining yellow oil-shaped material as fluorine cyclopropane.

Description

Fluorine-containing cyclopropane and synthetic method thereof
Technical field
The present invention relates to a kind of fluorine-containing cyclopropane and synthetic method thereof.
Background technology
This heterogeneous ring compound of cyclopropane is closely bound up with human life, and its structure fragment is prevalent in the natural compounds, and polysubstituted cyclopropane is not only the structural unit of natural product, important drugs, and is the important intermediate of organic synthesis.Simultaneously, the structure fragment of cyclopropane also is found in the heterogeneous ring compound that is present in many biologically actives.Therefore as everyone knows, heterogeneous ring compound has purposes very widely in actual life, and the research that fluorine element is introduced heterogeneous ring compound is extremely paid attention to, and some fluorine-containing heterocycles are in industry, agricultural, pharmaceutically be widely used.
In recent years, fluorine element is introduced the extensive concern that cyclopropane has been subjected to chemical field, many bibliographical informations the synthetic method and the using value of fluorine-containing cyclopropane derivative, fluorine-containing cyclopropane derivative is widely used in the biological medicine aspect.
Because fluorine element is introduced cyclopropane, make the character of compound that variation arranged, therefore synthesizing of fluorine-containing cyclopropane also caused the concern on chemical boundary.The method for preparing cyclopropane has a lot, but most of severe reaction conditions and reaction preference are poor, and it is less to prepare the method for fluorine-containing cyclopropane.
Summary of the invention:
One of purpose of the present invention is to provide the fluorine cyclopropane.
Two of purpose of the present invention is to provide the synthetic method of this fluorine-containing cyclopropane.
For achieving the above object, reaction mechanism of the present invention is:
Figure A20071003741100031
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of fluorine-containing cyclopropane is characterized in that, this compound has following structure:
Figure A20071003741100041
Wherein, X is:;-CN ,-C (O) OCH 3
R is :-CN, and-C (O) Ph,
Figure A20071003741100042
-Ph ,-C (O) OCH 3
A kind of method for preparing above-mentioned fluorine-containing cyclopropane, it is characterized in that, this method has following steps: with methylene dichloride as solvent, by 1: 1.1～2.5: 3～5 mixed in molar ratio, stirring at room is reacted to follow the tracks of in the reaction system to TLC and the trifluoromethyl ethene derivatives is not existed with p-trifluoromethyl phenyl ethene derivatives, Arsenic salt and salt of wormwood; Reaction is removed the solvent in the reaction system after finishing, and thin-layer chromatography separates, and developping agent is for pressing 8: 1 the volume ratio blended sherwood oil and the mixing solutions of ethyl acetate, and can obtain light yellow oil is fluorine-containing cyclopropane; Described structural formula to the trifluoromethyl ethene derivatives is:
Figure A20071003741100043
Wherein X is :-CN ,-C (O) OCH 3The structural formula of Suo Shu De Arsenic salt is: Ph 3A +SCH 2RBr -, wherein R is :-CN, and-C (O) Ph,
Figure A20071003741100044
-Ph ,-C (O) OCH 3
Because the structure fragment of cyclopropane is found in the heterogeneous ring compound that is present in many biologically actives, some compounds with cyclopropane structure fragment have insecticidal function, and the introducing of fluorine element may increase the disinsection efficiency of this compounds to a certain extent.Therefore think that the fluorine-containing cyclopropane that the present invention obtains may have insecticidal function, can be used for making sterilant, and because the effect of fluorine atom in its structure, fluorine-containing cyclopropane of the present invention has insecticidal properties preferably.
The inventive method is a raw material with the p-trifluoromethyl phenyl ethene derivatives that is easy to get and the Arsenic salt of Ji Ben, selects for use salt of wormwood as alkali, has reduced pollution, the selectivity height, and productive rate is moderate, so present method is effective novel method of synthetic fluorine-containing cyclopropane derivative.Simultaneously also provide a kind of valid approach for natural product synthetic.
Embodiment
The reaction concrete steps be: with methylene dichloride as solvent, salt of wormwood is as alkali, p-trifluoromethyl phenyl ethene derivatives, Arsenic salt and salt of wormwood by 1: 1.1～2.5: 3～5 mixed in molar ratio, stirring at room, TLC tracks to does not have the p-trifluoromethyl phenyl ethene derivatives in the reaction system, after reaction finishes, remove solvent with Rotary Evaporators, thin-layer chromatography separates, and developping agent is: sherwood oil: ethyl acetate (volume ratio is 8: 1), can obtain light yellow oil is fluorine-containing cyclopropane.Below be specific examples:
Example one: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, bromination methoxycarbonyl Jia base San Ben Ji Arsenic and salt of wormwood is 1: 2: 4, the fluorine-containing cyclopropane of gained is: [2,2-dicyan-3-(4-trifluoromethyl-phenyl)-cyclopropyl]-methoxyl group-methyl acetate, the structure of this compound is:
Figure A20071003741100051
Molecular formula: C 17H 13N 2O 3F 3
Chinese named: [2,2-dicyan-3-(4-trifluoromethyl-phenyl)-cyclopropyl]-methoxyl group-methyl acetate
English name: [2,2-Dicyano-3-(4-trifluoromethyl-phenyl)-cyclopropyl]-methoxy-acetic acidmethyl ester
Molecular weight: 350.0895
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.02 (d, J=7.5,1H, CH), 3.51 (d, J=7.5,1H, CH), 3.64 (s, 3H, OCH 3), 3.89 (s, 3H, OCH 3), 4.79 (s, 1H, CH), 7.28～7.59 (m, 4H, ArH) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 169.21,167.27,149.65,134.66,130.96 ( 2J C-F=32.5), 125.86 ( 3J C-F=3.6), 125.03,124.78 ( 1J C-F=270.5),, 122.62,89.12,53.39,50.87,29.38,26.40,14.14ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.8 (s, CF 3) ppm.
Example two: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, bromination acetonitrile San Ben Ji Arsenic and salt of wormwood is 1: 1.1: 3, and the fluorine-containing cyclopropane of gained is: 3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1, and 2-three nitriles, the structure of this compound is:
Figure A20071003741100052
Molecular formula: C 13H 6N 3F 3
Chinese named: 3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1,2-three nitriles
English name: 3-(4-Trifluoromethyl-phenyl)-cyclopropane-1,1,2-tricarbonitrile
Molecular weight: 261.0520
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.16 (d, J=8,1H, CH), 3.76 (d, J=8,1H, CH), 7.45～7.76 (m, 4H, ArH) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 135.2,132.9 ( 2J C-F=32.7Hz), 131.1,126.8 ( 3J C-F=3.7Hz), 124.2 ( 1J C-F=271.5Hz), and 112.5,110.7,109.5,38.2,20.1,14.2ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-63.1 (s, CF 3) ppm.
Example three: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, bromination benzoyl ylmethyl three benzene base Arsenic and salt of wormwood is 1: 2.5: 5; the fluorine-containing cyclopropane of gained is: 2-benzoyl-3-(4-trifluoromethyl-phenyl)-cyclopropane-1; the 1-dintrile, the structure of this compound is:
Molecular formula: C 19H 11N 2OF 3
Chinese named: 2-benzoyl-3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1-dintrile
English name: 2-Benzoyl-3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1-dicarbonitrile
Molecular weight: 340.0812
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.97 (d, J=8.0Hz, 1H, CH), 4.10 (d, J=8.0Hz, 1H, CH), 7.52～8.12 (m, 9H, ArH) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 188.4,138.1,135.4,133.5,132.0 ( 2J C-F=32.9Hz), 139.5,129.1,129.0,126.4 ( 3J C-F=3.6Hz), 124.5 ( 1J C-F=271.0Hz), and 111.9,111.2,35.6,32.2,15.2ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.9 (s, CF 3) ppm.
Example four: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, bromination thienyl formyl ylmethyl three benzene base Arsenic and salt of wormwood is 1: 1.1: 3; the fluorine-containing cyclopropane of gained is: 2-(thienyl-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-1; the 1-dintrile, the structure of this compound is:
Figure A20071003741100071
Molecular formula: C 17H 9N 2OF 3S
Chinese named: 2-(thienyl-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-1, the 1-dintrile
English name: 2-(Thiophene-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1-dicarbonitrile
Molecular weight: 346.0467
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.95 (d, J=8.0Hz, 1H, CH), 4.97 (d, J=8.0Hz, 1H, CH), 7.30 (dd, J=4.0,5.0Hz, 1H, thiophnen-H), 7.52～7.73 (m, 4H, ArH), 7.90 (d, J=5.0Hz, 1H, thiophene-H), 8.05 (d, J=4.0Hz, 1H, thiophene-H) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 180.4,142.2,137.5,135.2,134.4,133.4,132.0 ( 2J C-F=32.9Hz), 129.0,126.4 ( 3J C-F=3.6Hz), 124.6 ( 1J C-F=270.2Hz), and 111.8,111.1,37.5,36.3,15.1ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.9 (s, CF 3) ppm.
Example five: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, bromination furyl formyl ylmethyl three benzene base Arsenic and salt of wormwood is 1: 2.5: 5; the fluorine-containing cyclopropane of gained is: 2-(furans-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-1; the 1-dintrile, the structure of this compound is:
Figure A20071003741100072
Molecular formula: C 17H 9N 2O 2F 3
Chinese named: 2-(furans-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-1, the 1-dintrile
English name: 2-(Furan-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1-dicarbonitrile
Molecular weight: 330.0695
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.91 (d, J=8.0Hz, 1H, CH), 4.11 (d, J=8.0Hz, 1H, CH), 6.75 (dd, J=1.0,1.1Hz, 1H, furan-H), 7.53～7.73 (m, 4H, ArH), 7.54 (d, J=1.1Hz, 1H, furan-H), 7.80 (d, J=1.0Hz, 1H, furan-H) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 176.6,151.7,148.7,133.4,131.0 ( 2J C-F=32.9Hz), 126.3 ( 3J C-F=4Hz), 125.0,124.7,124.5 ( 1J C-F=272.0Hz), and 114.0,111.8,111.0,37.2,35.2,15.1ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.9 (s, CF 3) ppm.
Example six: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, bromination benzoyl ylmethyl three benzene base Arsenic and salt of wormwood is 1: 2: 4; the fluorine-containing cyclopropane of gained is: 1-ethanoyl-2-benzoyl-(4-trifluoromethyl-phenyl)-cyclopropane nitrile, and the structure of this compound is:
Figure A20071003741100081
Molecular formula: C 20H 14F 3NO 3
Chinese named: 1-ethanoyl-2-benzoyl-(4-trifluoromethyl-phenyl)-cyclopropane nitrile
English name: 1-Acethyl-2-benzoyl-3-(4-trifluoromethyl-phenyl)-cyclopropanecarbonitrile
Molecular weight: 373.09
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.73 (s, 3H, OCH 3), 3.74 (d, J=8.5Hz, 1H, CH), 3.89 (d, J=8.5Hz, 1H, CH), 7.52～8.02 (m, 9H, ArH) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 189.1,164.0,135.8,135.2,134.6,131.2 ( 2J C-F=32.8Hz), 129.2,128.8,128.5,126.1 ( 3J C-F=3.8Hz), 125.0,124.0 ( 1J C-F=271.5Hz), and 114.9,54.1,34.6,14.2ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.72 (s, CF 3) ppm.
Example seven: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, bromination furyl San Ben Ji Arsenic and salt of wormwood is that 1: 2.5: 5, the fluorine-containing cyclopropane of gained are: 1-ethanoyl-2-(furans-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane nitrile, and the structure of this compound is:
Figure A20071003741100091
Molecular formula: C 18H 12F 3NO 4
Chinese named: 1-ethanoyl-2-(furans-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane nitrile
English name: 1-Acetyl-2-(furan-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-carbonitrile
Molecular weight: 363.09
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.71 (d, J=8.5Hz, 1H, CH), 3.79 (s, 3H, OCH 3), 3.97 (d, J=8.5Hz, 1H, CH), 6.63 (d, J=1.5Hz, 1H, furan-H), 7.37 (d, J=3.5Hz, 1H, furan-H), 7.52～7.68 (m, 4H, ArH), 7.70 (dd, J=1.5,3.5Hz, 1H, furan-H) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 177.9,163.9,151.8,147.9,135.9,131.1 ( 2J C-F=32.8Hz), 129.6,128.9,126.0 ( 3J C-F=3.8Hz), 123.4 ( 1J C-F=271.5Hz), and 119.4,113.2,54.1,28.6,34.4,14.2ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.72 (s, CF 3) ppm.
Example eight: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, bromination thienyl San Ben Ji Arsenic and salt of wormwood is 1: 1.1: 3; the fluorine-containing cyclopropane of gained is: 1-ethanoyl-2-(thiophene phenol-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane nitrile, and the structure of this compound is:
Molecular formula: C 18H 12F 3NO 3S
Chinese named: 1-ethanoyl-2-(thiophene-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane nitrile
English name: 1-Acetyl-2-(thiophene-2-carbonyl)-3-(4-trifluoromethyl-phenyl)-cyclopropane-carbonitrile
Molecular weight: 379.05
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.67 (d, J=8.5Hz, 1H, CH), 3.78 (s, 3H, OCH 3), 3.91 (d, J=8.5Hz, 1H, CH), 7.21 (dd, J=3.0,5.0Hz, 1H, thiophene-H), 7.52～7.71 (m, 4H, ArH), 7.78 (d, J=5.0Hz, 1H, thiophene-H), 7.85 (d, J=3.0Hz, 1H, thiophene-H) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 181.6,163.8,142.2,135.8,131.2 ( 2J C-F=32.8Hz), 129.5,128.9,128.8,128.7,126.1 ( 3J C-F=3.6Hz), 124.0 ( 1J C-F=271.0Hz), and 114.8,54.2,39.9,35.7,14.2ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.74 (s, CF 3) ppm.
Example nine: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, benzyl bromide base San Ben Ji Arsenic and salt of wormwood is 1: 2.5: 5, the fluorine-containing cyclopropane of gained is: 1-cyano group-2-phenyl-3-(4-trifluoromethyl-phenyl)-cyclopropaneacetic acid methyl esters, and the structure of this compound is:
Figure A20071003741100101
Molecular formula: C 19H 14F 3NO 2
Chinese named: 1-cyano group-2-phenyl-3-(4-trifluoromethyl-phenyl)-cyclopropaneacetic acid methyl esters
English name: 1-Cyano-2-phenyl-3-(4-trifluoromethyl-phenyl)-cyclopropanecarboxylic acidmethyl ester
Molecular weight: 345.10
Outward appearance: light yellow liquid
Proton nmr spectra (500MHz, CDCl 3, interior mark: TMS): 3.65 (s, 3H, OCH 3), 3.73 (d, J=9.0Hz, 1H, CH), 3.91 (d, J=9.0Hz, 1H, CH), 7.36～7.70 (m, 9H, ArH) ppm;
Carbon-13 nmr spectra (500MHz, CDCl 3, interior mark: TMS): 171.2,167.9,164.0,130.5,130.2 ( 2J C-F=32.8Hz), 129.1,128.9,128.8,125.9 ( 3J C-F=3.6Hz), 124.9 ( 1J C-F=271.3Hz), and 116.2,53.7,40.8,35.8,14.2ppm;
Nucleus magnetic resonance fluorine spectrum (500MHz, CDCl 3, interior mark: C 6F 6) :-62.67 (s, CF 3) ppm.
Example ten: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, bromination acetonitrile San Ben Ji Arsenic and salt of wormwood is 1: 2.5: 5, and the fluorine-containing cyclopropane of gained is: 1, and 2-dicyan-3-(4-trifluoromethyl-phenyl)-cyclopropaneacetic acid methyl esters.
Example 11: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, bromination methoxycarbonyl Jia base San Ben Ji Arsenic and salt of wormwood is 1: 1.1: 3, the fluorine-containing cyclopropane of gained is: 1-cyanogen-3-(4-trifluoromethyl-phenyl) cyclopropane-1,2-oxalic acid dimethyl ester.
Example 12: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, benzyl bromide San Ben Ji Arsenic and salt of wormwood is 1: 2.5: 5, and the fluorine-containing cyclopropane of gained is: 2-phenyl-3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1-dintrile.
Example 13: the mol ratio of 2-cyano group-3-(4-trifluoromethyl-phenyl)-methyl acetate, acetyl bromide ylmethyl San Ben Ji Arsenic and salt of wormwood is 1: 2.5: 5, and the fluorine-containing cyclopropane of gained is: 2-ethanoyl-1-cyanogen-3-(4-trifluoromethyl-phenyl)-cyclopropaneacetic acid methyl esters.
Example 14: the mol ratio of 4-trifluoromethyl-benzene methene base propane dinitrile, acetyl bromide ylmethyl San Ben Ji Arsenic and salt of wormwood is 1: 2.5: 5, and the fluorine-containing cyclopropane of gained is: 2-ethanoyl-3-(4-trifluoromethyl-phenyl)-cyclopropane-1,1-dintrile.

Claims (2)

1. a fluorine-containing cyclopropane is characterized in that, this compound has following structure:
Figure A2007100374110002C1
Wherein, X is :-CN ,-C (O) OCH 3
R is :-CN, and-C (O) Ph,
Figure A2007100374110002C2
-Ph ,-C (O) OCH 3
2. the method for a synthetic fluorine-containing cyclopropane according to claim 1, it is characterized in that, this method has following steps: with methylene dichloride as solvent, by 1: 1.1～2.5: 3～5 mixed in molar ratio, stirring at room is reacted to follow the tracks of in the reaction system to TLC and the trifluoromethyl ethene derivatives is not existed with p-trifluoromethyl phenyl ethene derivatives, Arsenic salt and salt of wormwood; Reaction is removed the solvent in the reaction system after finishing, and thin-layer chromatography separates, and developping agent is for pressing 8: 1 the volume ratio blended sherwood oil and the mixing solutions of ethyl acetate, and can obtain light yellow oil is fluorine-containing cyclopropane; Described structural formula to the trifluoromethyl ethene derivatives is:
Figure A2007100374110002C3
Wherein X is :-CN ,-C (O) OCH 3The structural formula of described clock salt is: Ph 3As +CH 2RBr -, wherein R is :-CN, and-C (O) Ph, -Ph ,-C (O) OCH 3
CN 200710037411 2007-02-09 2007-02-09 Fluorine-containing cyclopropane and synthetic method thereof Pending CN101012184A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102992947A (en) * 2011-09-14 2013-03-27 中化蓝天集团有限公司 Pentachlorocyclopropane preparation method

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102992947A (en) * 2011-09-14 2013-03-27 中化蓝天集团有限公司 Pentachlorocyclopropane preparation method
CN102992947B (en) * 2011-09-14 2014-12-17 中化蓝天集团有限公司 Pentachlorocyclopropane preparation method

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