CN105181824A - High performance liquid chromatography detection method of 3,4,5-trifluorophenylboronic acid - Google Patents
High performance liquid chromatography detection method of 3,4,5-trifluorophenylboronic acid Download PDFInfo
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- CN105181824A CN105181824A CN201510406439.9A CN201510406439A CN105181824A CN 105181824 A CN105181824 A CN 105181824A CN 201510406439 A CN201510406439 A CN 201510406439A CN 105181824 A CN105181824 A CN 105181824A
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Abstract
The invention discloses a high performance liquid chromatography detection method of 3,4,5-trifluorophenylboronic acid, and belongs to the technical field of chemical analysis. According to the high performance liquid chromatography detection method, octadecyl silane is taken as a packed column, distilled water-acetonitrile is taken as a mobile phase, and phosphoric acid is added into the mobile phase. The high performance liquid chromatography detection method can be used for accurate analysis and determination of the content of 3,4,5-trifluorophenylboronic acid and related substances, effective control of the quality of 3,4,5-trifluorophenylboronic acid in practical production processes, and providing construction of universal standards of the product with foundation.
Description
Technical field:
The present invention relates to chemical analysis technology field, be specifically related to a kind of high performance liquid chromatography method of inspection of 3,4,5-trifluoro-benzene boric acid.
Background technology:
Fluoride-bearing phenyloboric acid be a class in atmosphere more stable, insensitive to moisture, can preserve for a long time and the higher organic synthesis of reactivity and medicine, chemical intermediate.Regioselectivity and the stereoselectivity of the Suzuki coupling reaction of fluoride-bearing phenyloboric acid and halogenated aryl hydrocarbon are good, and various chemical functional group does not change in the reaction, and reaction conditions is gentle, and productive rate is high, are the important channels forming C-C key.Fluoride-bearing phenyloboric acid has very important application in organic synthesis is as the forming reactions of C-O key, C-N key, C-S key.Fluoride-bearing phenyloboric acid is fluorine-containing single-substituted boronic acid derivatives, because the atomic radius of fluorine atom and hydrogen atom is close, so after the hydrogen atom in molecule replaced by fluorine, can't cause the marked change of this molecule steric-configuration.But because fluorine atom has very strong electrophilic, the electronic property of original molecule is often made to change a lot, thus make fluoride-bearing phenyloboric acid have good stability and large dielectric anisotropy, in recent years in organic synthesis, biomedicine, agricultural chemicals and materialogy, have very important effect, in liquid crystal display material, effect is particularly remarkable especially.We find that in the process of Development and Production 3,4,5-trifluoro-benzene boric acid this compound does not have ready-made determination and analysis method, and we do not find the content of 3,4,5-trifluoro-benzene boric acid and the detection method of impurity in the document published yet.This makes the analytical standard that this product is ununified, hinders applying of this product.Therefore set up and stablize effective analytical approach and be very important.
Summary of the invention:
Technical matters to be solved by this invention is to provide that a kind of analysis speed is fast, detection sensitivity is high and the high performance liquid chromatography method of inspection of analysis result 3,4,5-trifluoro-benzene boric acid accurately.
Technical matters to be solved by this invention adopts following technical scheme to realize:
A kind of high performance liquid chromatography method of inspection of 3,4,5-trifluoro-benzene boric acid, take octadecyl silane as packed column, distilled water-acetonitrile is mobile phase, and adds phosphoric acid in mobile phase.
The addition of described phosphoric acid is 5.0mmol/L.
60:40 is formulated by volume by distilled water and acetonitrile for described mobile phase.
Due to 3,4,5-trifluoro-benzene boric acid and its raw material 3.4.5-trifluorobromobenzene have absorption at determined wavelength 254mm, first will determine can by two kinds of separating substances, by the analysis to 3,4,5-trifluoro-benzene boric acid character, selecting with octadecyl silane is packed column, the high pressure liquid chromatographic analysis method being mobile phase with distilled water-acetonitrile.Through test of many times, filter out the ratio of distilled water and the volume of acetonitrile, but separating effect is undesirable, the main peak of separation has more serious conditions of streaking, sees Fig. 1.Find through repetition test research, in mobile phase, add phosphoric acid can well solve conditions of streaking.
The invention has the beneficial effects as follows: the present invention can analyze content and the related substance of mensuration 3,4,5-trifluoro-benzene boric acid exactly, thus effectively 3 can be controlled in actual production process, the quality of 4,5-trifluoro-benzene boric acid, and set up unified standard for this product and lay the first stone.
Accompanying drawing illustrates:
Fig. 1 is the high-efficient liquid phase chromatogram not adding phosphoric acid in mobile phase;
Fig. 2,3 is the high-efficient liquid phase chromatogram adding 5.0mmol/L phosphoric acid in mobile phase.
Embodiment:
The technological means realized to make the present invention, creation characteristic, reaching object and effect is easy to understand, below in conjunction with specific embodiment and diagram, setting forth the present invention further.
Embodiment 1:
1, instrument: Agilent 1260A--high performance liquid chromatograph, electronic balance
2, assay method:
Precision takes sample 50mg, is placed in 2ml sample bottle, adds mobile phase, and ultrasonic dissolution is also diluted to scale, shakes up, as need testing solution; Take octadecyl silane as packed column, 60:40 is formulated by volume by 5mmol phosphoric acid solution and acetonitrile for mobile phase; 5mmol phosphoric acid solution is by 0.576g phosphoric acid (reagent), and the 1000ml that adds water shakes up formulated.Determined wavelength is 254nm, flow velocity 1.0ml/min.Get in need testing solution 8ul injection liquid chromatography, record chromatogram is to main peak retention time 6 times.
Embodiment 2:
1, instrument: Agilent 1260A--high performance liquid chromatograph, electronic balance
2, assay method:
Standard solution is prepared: precision takes 3,4,5-trifluoro-benzene boric acid standard items 50mg, and 100mg, 150mg as in 25ml volumetric flask, dissolve with mobile phase and are diluted to scale, shaking up respectively, for subsequent use as standard solution.
Typical curve: the standard solution single injected sampling getting above-mentioned 3 concentration, each standard solution enters 2 pins, and record spectrogram, does weight/peak area peak area logarithm value curve.Related coefficient >=0.999.
Sample solution is prepared: precision takes sample 100mg, puts in 25ml measuring bottle, adds mobile phase ultrasonic dissolution and is diluted to scale, shaking up, as need testing solution; Take octadecyl silane as packed column, 60:40 is formulated by volume by 5mmol phosphoric acid solution and acetonitrile for mobile phase; 5mmol phosphoric acid solution is by 0.576g phosphoric acid (reagent), and the 1000ml that adds water shakes up formulated.Determined wavelength is 254nm, flow velocity 1.0ml/min, and theoretical cam curve calculates should be not less than 3000 with 3,4,5-trifluoro-benzene boric acid.Get in need testing solution 8ul injection liquid chromatography, adjust record chromatogram to main peak retention time 6 times.As stated above, the high-efficient liquid phase chromatogram obtained is as Fig. 2, Fig. 3.Usable floor area normalization method calculates the purity of 3,4,5-trifluoro-benzene boric acid; Replicate determination 2 times, the difference of twice parallel determinations must not be greater than 0.1%.
The analysis result of table 1 first time mensuration 3,4,5-trifluoro-benzene boric acid liquid chromatography
Table 2 second time measures the analysis result of 3,4,5-trifluoro-benzene boric acid liquid chromatography
Table 33, the comparison of 4,5-trifluoro-benzene boric acid, twice measured value
More than show and describe ultimate principle of the present invention and principal character and advantage of the present invention.The technician of the industry should understand; the present invention is not restricted to the described embodiments; what describe in above-described embodiment and instructions just illustrates principle of the present invention; without departing from the spirit and scope of the present invention; the present invention also has various changes and modifications, and these changes and improvements all fall in the claimed scope of the invention.Application claims protection domain is defined by appending claims and equivalent thereof.
Claims (3)
1. the high performance liquid chromatography method of inspection of a trifluoro-benzene boric acid, is characterized in that: take octadecyl silane as packed column, distilled water-acetonitrile is mobile phase, and adds phosphoric acid in mobile phase.
2. the high performance liquid chromatography method of inspection of 3,4,5-trifluoro-benzene boric acid according to claim 1, is characterized in that: the addition of described phosphoric acid is 5.0mmol/L.
3. the high performance liquid chromatography method of inspection of 3,4,5-trifluoro-benzene boric acid according to claim 1, is characterized in that: 60:40 is formulated by volume by distilled water and acetonitrile for described mobile phase.
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| CN201510406439.9A CN105181824A (en) | 2015-07-09 | 2015-07-09 | High performance liquid chromatography detection method of 3,4,5-trifluorophenylboronic acid |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105823840A (en) * | 2016-03-18 | 2016-08-03 | 蚌埠市产品质量监督检测中心 | High performance liquid chromatography (HPLC) detection method of 3,4-difluorophenylboronic acid |
| CN113075328A (en) * | 2021-04-01 | 2021-07-06 | 南京和曦生物科技有限公司 | Separation and purification process of 4-5 fluorophenyl boron compound |
| CN113933404A (en) * | 2021-08-30 | 2022-01-14 | 北京泰德制药股份有限公司 | Method for measuring boric acid content |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015053975A1 (en) * | 2013-10-07 | 2015-04-16 | The Board Of Trustees Of The University Of Illinois | Volume response sensors having controlled reversible crosslinking |
| CN104530107A (en) * | 2014-12-31 | 2015-04-22 | 大连联化化学有限公司 | Synthetic method for 3-amino-4-fluorophenylboronic acid |
-
2015
- 2015-07-09 CN CN201510406439.9A patent/CN105181824A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2015053975A1 (en) * | 2013-10-07 | 2015-04-16 | The Board Of Trustees Of The University Of Illinois | Volume response sensors having controlled reversible crosslinking |
| CN104530107A (en) * | 2014-12-31 | 2015-04-22 | 大连联化化学有限公司 | Synthetic method for 3-amino-4-fluorophenylboronic acid |
Non-Patent Citations (3)
| Title |
|---|
| ZHENFU HAN ET AL.: "Convenient preparation of highly active phase-transfer catalyst for catalytic asymmetric synthesis of a-alkyl- and a,a-dialkyl-a-amino acids: application to the short asymmetric synthesis of BIRT-377", 《TETRAHEDRON LETTERS》 * |
| 郭敬: "取代芳基硼酸的合成研究", 《中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑》 * |
| 钟为慧 等: "含氟苯硼酸的合成及应用研究进展", 《有机化学》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105823840A (en) * | 2016-03-18 | 2016-08-03 | 蚌埠市产品质量监督检测中心 | High performance liquid chromatography (HPLC) detection method of 3,4-difluorophenylboronic acid |
| CN113075328A (en) * | 2021-04-01 | 2021-07-06 | 南京和曦生物科技有限公司 | Separation and purification process of 4-5 fluorophenyl boron compound |
| CN113933404A (en) * | 2021-08-30 | 2022-01-14 | 北京泰德制药股份有限公司 | Method for measuring boric acid content |
| CN113933404B (en) * | 2021-08-30 | 2023-05-05 | 北京泰德制药股份有限公司 | Method for measuring boric acid content |
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