56882-52-1|Ethyl 2,4-dichlorobenzoate| Ambeed

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Quality Control of [ 56882-52-1 ] Purity: 98+% SDS Specification

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Product Details of [ 56882-52-1 ]

CAS No. :	56882-52-1
Formula :	C₉H₈Cl₂O₂
M.W :	219.06
SMILES Code :	O=C(OCC)C1=CC=C(Cl)C=C1Cl
MDL No. :	MFCD00277702
InChI Key :	ZBBGAUHWTZKKQQ-UHFFFAOYSA-N
Pubchem ID :	42026

Safety of [ 56882-52-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Application In Synthesis of [ 56882-52-1 ]

* 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.

Downstream synthetic route of [ 56882-52-1 ]

[ 56882-52-1 ] Synthesis Path-Downstream 1~35

1
[ 917-64-6 ]
[ 56882-52-1 ]
[ 104517-04-6 ]

References: [1]Journal of the American Chemical Society,1948,vol. 70,p. 622.

2
[ 56882-52-1 ]
[ 5814-06-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrazine hydrate; In ethanol; for 6.5h;Reflux;	General procedure: A mixture of substituted ethyl benzoate (12a-g) (0.1M) and hydrazine hydrate (0.3M) was heated under reflux for 30min. Ethanol (20mL) was added to the refluxing mixture as a solvent in order to homogenize the solution, the resulting mixture was further allowed for 6h. Excess of ethanol was distilled out and the content was allowed to cool. The crystals formed were filtered and washed thoroughly with water and dried.
	With hydrazine hydrate; In ethanol;Reflux;	General procedure: To a stirred solution of ethyl benzoate (3 mmol) derivatives in ethanol was added hydrazine-hydrate (5.44 mmol) and refluxed for 6-12 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain the respective benzohydrazide derivatives (4a-m)15,16. The yields of the products varied from 80-85 %.
	With hydrazine hydrate; In ethanol; at 20℃; for 3h;	General procedure: A mixture of substituted ethyl benzoate 2 (10 mmol) and hydrazinehydrate (20 mmol) in ethanol was stirred at room temperaturefor 3 h and then filtered. The crude product recrystallizedfrom absolute alcohol to give 3a-l, which were used directly forthe next step. Under this same condition, the intermediate compounds 8a-d were also prepared.

	With hydrazine hydrate; In ethanol; for 5h;Reflux;	General procedure: 5mL of hydrazine monohydrate (80%) was added to a solution of intermediate 3 (5mmol) in ethanol (5mL). The reaction mixture was maintained under reflux for 5h. was then concentrated under reduced pressure and the resulting solid was collected by filtration, washed with cold water and dried to give the desired intermediate 4 as a white solid.
	With hydrazine hydrate; In methanol;Reflux;	General procedure: The ethyl esters (0.15 mol; 2a-o) were taken in 250 mL round bottom flask.About 30 mL of methanol was added to the flask and homogenized by stirringat room temperature. Hydrazine hydrate (80%; 0.15 mol) was introduced to theflask drop wise and the reaction apparatus was refluxed for 5-6 hrs. Reactionprogress was confirmed by thin layer chromatography. n-Hexane and ethylacetate (3:2). At the end of reaction, excess of solvent was evaporated andresidue was poured into the ice cold water. Precipitates of acid hydrazides werefiltered, washed with water and dried. Re-crystallization of acid hydrazides wasperformed by using methanol.
	With hydrazine; In ethanol;Reflux;	General procedure: The synthesized aryl/aralkyl esters (IIa-n)(3.5 mL) were diluted in 250 mL ethanol followed byaddition of 4.8 mL 80% hydrazine. Refluxing wascontinued for 4-6 h. After monitoring by TLC, icecold distilled H2O was poured to acquire the precipitatesof (IIIa-n), which were filtered and washed offwith cold distilled H2O [18, 19].
	With hydrazine hydrate; In ethanol;Reflux;	General procedure: Ethyl ester (Va-n) (0.04 mol) was refluxed with 80% N2H4 · H2O(7.2 mL) for 3-4 h in 20 mL EtOH in a round-bottom flask (100 mL). The reaction was monitored by TLC. At completion, excess ice-cold distilled water (60 mL) was added to get the precipitate, which was filtered, washed with distilled water, and dried to acquire title compounds (VIa-n) [18, 19].

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 3943 - 3949.
[2]Journal of Heterocyclic Chemistry,1986,vol. 23,p. 793 - 795.
[3]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 1225 - 1229.
[4]Journal of Heterocyclic Chemistry,1984,vol. 21,p. 205 - 208.
[5]Pharmaceutical Bulletin,1955,vol. 3,p. 194,198.
[6]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1984,vol. 23,p. 796 - 797.
[7]Journal of the Indian Chemical Society,1984,vol. 61,p. 530 - 533.
[8]European Journal of Medicinal Chemistry,2006,vol. 41,p. 841 - 846.
[9]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2278 - 2282.
[10]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7565 - 7572.
[11]European Journal of Medicinal Chemistry,2009,vol. 44,p. 2113 - 2121.
[12]European Journal of Medicinal Chemistry,2009,vol. 44,p. 2985 - 2993.
[13]Journal of Medicinal Chemistry,2009,vol. 52,p. 4200 - 4209.
[14]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2010,vol. 49,p. 526 - 531.
[15]Journal of Heterocyclic Chemistry,2010,vol. 47,p. 838 - 845.
[16]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 332 - 335.
[17]Medicinal Chemistry Research,2012,vol. 21,p. 3646 - 3655.
[18]European Journal of Medicinal Chemistry,2013,vol. 70,p. 469 - 476.
[19]Medicinal Chemistry Research,2014,vol. 23,p. 2080 - 2092.
[20]RSC Advances,2015,vol. 5,p. 12807 - 12820.
[21]Asian Journal of Chemistry,2015,vol. 27,p. 3605 - 3608.
[22]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1879 - 1888.
[23]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 207 - 212.
[24]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1423 - 1429.
[25]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5652 - 5661.
[26]Cancer Chemotherapy and Pharmacology,2017,vol. 80,p. 1027 - 1042.
[27]Journal of the Chilean Chemical Society,2017,vol. 62,p. 3370 - 3375.
[28]Russian Journal of Bioorganic Chemistry,2017,vol. 43,p. 328 - 339.
Bioorg. Khim.,2017,vol. 43,p. 328 - 339,12.
[29]RSC Advances,2018,vol. 8,p. 6306 - 6314.
[30]Russian Journal of Bioorganic Chemistry,2018,vol. 44,p. 801 - 811.
Bioorg. Khim.,2018,vol. 44,p. 801 - 811,11.
[31]Chemical Papers,2019,vol. 73,p. 17 - 25.
[32]European Journal of Pharmaceutical Sciences,2019,vol. 136.
[33]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 11572 - 11581.

3
[ 56882-52-1 ]
[ 50-84-0 ]

References: [1]Tetrahedron Letters,1990,vol. 31,p. 3943 - 3944.

4
[ 64-17-5 ]
[ 89-75-8 ]
[ 56882-52-1 ]

References: [1]Journal of the Indian Chemical Society,1984,vol. 61,p. 530 - 533.
[2]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 11572 - 11581.

5
[ 56882-52-1 ]
[ 17287-03-5 ]
[ 35112-28-8 ]

References: [1]Chemosphere,1997,vol. 35,p. 1233 - 1241.

6
[ 56882-52-1 ]
[ 75-05-8 ]
[ 39528-61-5 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 311 - 341.

7
[ 27464-82-0 ]
[ 56882-52-1 ]
1-(2,4-Dichlorphenyl)-2-[5-methyl-1,3,4-thiadiazol-2-yl]ethanon [ No CAS ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2004,vol. 59,p. 366 - 374.

8
[ 64-17-5 ]
[ 50-84-0 ]
[ 56882-52-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; for 8h;Reflux;	General procedure: A mixture of substituted benzoic acids (11a-g) (0.001M, 2.12g) and ethanol (20mL) were heated under reflux until the benzoic acid was dissolved in ethanol then few drops of concentrated H2SO4 was added to the mixture and reflux for 8h. The resulting mixture was cooled to room temperature and a saturated solution of sodium bicarbonate was added to the mixture to neutralise the benzoic acid. The precipitated product was filtered and washed with water and dried. The dried product was recrystallized with ethanol.
	With sulfuric acid;Reflux;	General procedure: To a stirred solution of different benzoic acids (6.42 mmol) in ethanol (3 mL) was added H2SO4 (0.1mL) and heated to reflux for 6-10 h. The reaction mixture was diluted with ethyl acetate followed by water. The organic layer was washed with saturated NaHCO3 followed by water and brine solution. The organic layer was dried over sodium sulphate, filtered and evaporated to obtain the respective ethyl benzoate derivatives.
	With sulfuric acid;Reflux;	General procedure: We added dense H2SO4 (0.098g, 1mmol) to a solution of substituted benzoic acid (5mmol) in dry ethyl alcohol (10mL). The mixture was heated under reflux until completion (as monitored via TLC), and the solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate (50mL) and washed with 0.1M Na2CO3, brine, dried and concentrated, respectively. The crude products (intermediate 3) were used directly for the next step.

	With sulfuric acid;Reflux;	General procedure: The different organic acid (0.02 mol; 1a-o) was taken in 200 mL roundbottom flask. 20 mL absolute ethanol (99%) was added to the flask andstirred for ten minutes to homogenize the reaction contents. Later on, 2.5 mLconcentrated sulphuric acid, an activator, was added and reaction contents wererefluxed for 3-4 hours. Thin layer chromatography was the technique used tomonitor the completion of reaction by using 1:4 ratio of n-hexane and ethylacetate as mobile phase. After maximum completion, reaction mixture wastreated with 10% aqueous Na2CO3 (pH 9-10) to neutralize the reaction mixtureand to remove unreacted free acid. To get the pure esters, solvent extraction ofneutralized reaction mixture was performed by 50 mL of CHCl3 in a separatingfunnel for 3-4 times. After that CHCl3 layer was separated from the lowerdensity aqueous layer and was distilled by using rotary evaporator to acquireethyl esters.
	With sulfuric acid;Reflux;	General procedure: Aryl/aralkyl carboxylic acids (Ia-n) (0.032 mol)were homogenized in ethanol (99%, 30 mL) in a 250mL round bottom flask. Concentrated sulfuric acid(2.5 mL) was added in the mixture and set to reflux for3-5 h. TLC was developed for monitoring reactioncompletion. At maximum completion, the 10% aqueoussodium carbonate solution was poured to neutralizethe mixture up to pH of 9-10 after addition of 150mL distilled water. This step converted untreatedorganic acid and sulfuric acid into salts washed awayby aqueous layer. The esters were filtered or extractedby solvent extraction technique using 50 mL chloroformor diethyl ether from a separating funnel. Chloroform wasdistilled off to collect esters (IIa-n) [18, 19].
	With sulfuric acid;Reflux;	General procedure: (Un)Substituted benzoic acid (IVa-n) (0.02 mol) was refluxed with 60 mL EtOH for 4-5 h in the presence of conc. H2SO4 (1.25 mL) in around-bottom flask (250 mL). TLC plates were used to monitor the reaction. Excess distilled water (150 mL) was added after reaction completion and pH was adjusted to 8-10 by 20% aq. Na2CO3 solution. The product was collected through sequential extraction with CHCl3 (20 mL × 3). Chloroform was distilled off to collect the product. In some cases, the product was collected through filtration. Esters (Va-n) were used in further synthesis [18, 19].
	With sulfuric acid; at 80℃; for 7h;	General procedure: Taking 6a as an example, a mixture of benzoic acid (2.5 g,20.0 mmol), 4 mL sulfuric acid, and 50 mL ethanol was heated under reflux for 7 h (hour, h). After finishing the reaction, it was poured into water and extracted by ethylacetate, dried with anhydrous Na2SO4, and then the solventof the organic phase was evaporated under vacuum to give colorless liquid 4a. Then excess 80% N2H4·H2O and 15 mLof ethanol were added into the flask containing 4a, which was heated under reflux about 5 h. After the reaction was completed, it should be cooled into room temperature overnight and the white solid 5a was given after being filtered, washed with ethanol and dried in open air. Finally, 5a (1.4 g,8.0 mmol) was then subjected to substitution reaction with KOH (0.9 g, 15.6 mmol) and CS2(1.2 g, 15.0 mmol) togenerate intermediate 6a. At the same time, 6b-6m was synthesized by the methods described in the literature (Shi et al.2015; Du et al. 2013).

References: [1]European Journal of Medicinal Chemistry,2006,vol. 41,p. 841 - 846.
[2]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7565 - 7572.
[3]European Journal of Medicinal Chemistry,2009,vol. 44,p. 2985 - 2993.
[4]Journal of Medicinal Chemistry,2009,vol. 52,p. 4200 - 4209.
[5]European Journal of Medicinal Chemistry,2010,vol. 45,p. 3943 - 3949.
[6]European Journal of Medicinal Chemistry,2009,vol. 44,p. 2113 - 2121.
[7]Medicinal Chemistry Research,2012,vol. 21,p. 3646 - 3655.
[8]European Journal of Medicinal Chemistry,2013,vol. 70,p. 469 - 476.
[9]Medicinal Chemistry Research,2014,vol. 23,p. 2080 - 2092.
[10]RSC Advances,2015,vol. 5,p. 12807 - 12820.
[11]Asian Journal of Chemistry,2015,vol. 27,p. 3605 - 3608.
[12]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2016,vol. 55B,p. 207 - 212.
[13]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1423 - 1429.
[14]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 5652 - 5661.
[15]Journal of the Chilean Chemical Society,2017,vol. 62,p. 3370 - 3375.
[16]Russian Journal of Bioorganic Chemistry,2017,vol. 43,p. 328 - 339.
Bioorg. Khim.,2017,vol. 43,p. 328 - 339,12.
[17]Russian Journal of Bioorganic Chemistry,2018,vol. 44,p. 801 - 811.
Bioorg. Khim.,2018,vol. 44,p. 801 - 811,11.
[18]Chemical Papers,2019,vol. 73,p. 17 - 25.
[19]European Journal of Pharmaceutical Sciences,2019,vol. 136.
[20]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 15544 - 15553.

9
[ 56882-52-1 ]
[ 76292-53-0 ]
(Z)-1-(2-benzyloxy-4-chlorophenyl)-3-(2,4-dichlorophenyl)-3-hydroxyprop-2-en-1-one [ No CAS ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

10
[ 64-17-5 ]
[ 874-42-0 ]
[ 56882-52-1 ]

References: [1]Journal of the Chinese Chemical Society,2017,vol. 64,p. 303 - 309.
[2]Organic Letters,2007,vol. 9,p. 3515 - 3518.

11
[ 56882-52-1 ]
[ 1023279-03-9 ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

12
[ 56882-52-1 ]
[ 1023279-05-1 ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

13
[ 56882-52-1 ]
[ 1023279-06-2 ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

14
[ 56882-52-1 ]
[ 1023279-08-4 ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

15
[ 56882-52-1 ]
[ 1023279-07-3 ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

16
[ 56882-52-1 ]
3-(4-chloro-2-hydroxyphenyl)-5-(2,4-dichlorophenyl)-1-decyl-1H-pyrazole [ No CAS ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

17
[ 56882-52-1 ]
3-(4-chloro-2-hydroxyphenyl)-5-(2,4-dichlorophenyl)-1-dodecyl-1H-pyrazole [ No CAS ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

18
[ 56882-52-1 ]
5-(4-chloro-2-hydroxyphenyl)-3-(2,4-dichlorophenyl)-1-decyl-1H-pyrazole [ No CAS ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

19
[ 56882-52-1 ]
5-(4-chloro-2-hydroxyphenyl)-3-(2,4-dichlorophenyl)-1-dodecyl-1H-pyrazole [ No CAS ]

References: [1]Monatshefte fur Chemie,2007,vol. 138,p. 797 - 811.

20
[ 56882-52-1 ]
{2-[5-(2,4-Dichloro-phenyl)-[1,3,4]oxadiazol-2-ylsulfanylmethyl]-phenyl}-[(E)-methoxyimino]-acetic acid methyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2278 - 2282.

21
[ 56882-52-1 ]
[ 23288-92-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 2278 - 2282.
[2]European Journal of Medicinal Chemistry,2013,vol. 70,p. 469 - 476.
[3]Bioorganic and Medicinal Chemistry,2016,vol. 24,p. 1879 - 1888.
[4]Journal of Heterocyclic Chemistry,2017,vol. 54,p. 1423 - 1429.
[5]Journal of the Chilean Chemical Society,2017,vol. 62,p. 3370 - 3375.
[6]Russian Journal of Bioorganic Chemistry,2017,vol. 43,p. 328 - 339.
Bioorg. Khim.,2017,vol. 43,p. 328 - 339,12.
[7]Russian Journal of Bioorganic Chemistry,2018,vol. 44,p. 801 - 811.
Bioorg. Khim.,2018,vol. 44,p. 801 - 811,11.
[8]Chemical Papers,2019,vol. 73,p. 17 - 25.
[9]Journal of Agricultural and Food Chemistry,2021,vol. 69,p. 15544 - 15553.

22
[ 56882-52-1 ]
6-(2,4-dichloro-phenyl)-1<i>H</i>-imidazo[1,2-<i>b</i>]pyrazole [ No CAS ]

References: [1]Synthetic Communications,1999,vol. 29,p. 311 - 341.

23
[ 56882-52-1 ]
[ 222056-36-2 ]

References: [1]Synthetic Communications,1999,vol. 29,p. 311 - 341.

24
[ 50-84-0 ]
[ 56882-52-1 ]

References: [1]Journal of the Indian Chemical Society,1984,vol. 61,p. 530 - 533.
[2]Journal of Medicinal Chemistry,1983,vol. 26,p. 765 - 768.

25
[ 56882-52-1 ]
[ 26036-09-9 ]