89-20-3|4-Chlorophthalic acid| Ambeed

CAS No. :	89-20-3
Formula :	C₈H₅ClO₄
M.W :	200.58
SMILES Code :	O=C(O)C1=CC=C(Cl)C=C1C(O)=O
MDL No. :	MFCD00044755
InChI Key :	DVIPPHSQIBKWSA-UHFFFAOYSA-N
Pubchem ID :	6964

Safety of [ 89-20-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of [ 89-20-3 ]

* 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 [ 89-20-3 ]

[ 89-20-3 ] Synthesis Path-Downstream 1~54

1
[ 67-56-1 ]
[ 89-20-3 ]
[ 58138-38-8 ]

References: [1]Journal of the Chemical Society,1929,p. 255.

2
[ 56-23-5 ]
[ 610-27-5 ]
[ 89-20-3 ]

References: [1]Ukrainskij Khimicheskij Zhurnal,1958,vol. 24,p. 68.
Chem.Abstr.,1958,p. 18325.

3
[ 14548-38-0 ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1892,vol. 25,p. 2115.

4
[ 64-17-5 ]
[ 89-20-3 ]
[ 38717-95-2 ]

References: [1]Justus Liebigs Annalen der Chemie,1950,vol. 570,p. 15,31.

5
[ 2198-77-8 ]
[ 89-20-3 ]

References: [1],1881,p. 9.
Bulletin de la Societe Chimique de France,1881,vol. <2> 36,p. 433.

6
[ 89-20-3 ]
[ 118-45-6 ]

Yield	Reaction Conditions	Operation in experiment
		A. 5-Chloro-1,3-isobenzofurandione <strong>[89-20-3]4-Chlorophthalic acid</strong> (446.5 g, 2.23 mol) was heated neat until H2 O was no longer released to give compound A (415.9 g, quantitative), melting point 138-140 C.
		EXAMPLE IX In a conventional acidic hydrolysis, the 4-chlorophthaloyl chloride or 4-chlorophthalonitrile of Examples 7 or 8 is hydrolyzed to <strong>[89-20-3]4-chlorophthalic acid</strong> which, upon dehydration at over 180-200 C., will afford a high yield of 4-chlorophthalic anhydride.

References: [1]Journal of Organic Chemistry,1983,vol. 48,p. 2465 - 2468.
[2]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 1388 - 1391.
[3]Organic Letters,2010,vol. 12,p. 4796 - 4799.
[4]Chemische Berichte,1882,vol. 15,p. 320.
[5]Journal of the Chemical Society. Perkin transactions I,1980,p. 1834 - 1840.
[6]Patent: US5739135,1998,A .
[7]Patent: US5049682,1991,A .

7
[ 89-20-3 ]
[ 610-35-5 ]

References: [1]Doklady Akademii Nauk SSSR, <NS> 1933 118,.
Chemisches Zentralblatt,1935,vol. 106,p. 1617.

8
[ 2065-70-5 ]
[ 89-20-3 ]

References: [1]Bulletin de la Societe Chimique de France,1881,vol. <2> 36,p. 434.
[2]Chemische Berichte,1882,vol. 15,p. 320.

9
[ 40604-49-7 ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1882,vol. 15,p. 320.
[2]Chemische Berichte,1882,vol. 15,p. 320.

10
[ 35337-44-1 ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 2338.

11
[ 7499-06-1 ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 1759.
[2]Journal of Organic Chemistry,1960,vol. 25,p. 334 - 343.

12
[ 7499-07-2 ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 1759.
[2]Journal of Organic Chemistry,1961,vol. 26,p. 2310 - 2316.
[3]Chemische Berichte,1885,vol. 18,p. 1759.

13
[ 37074-38-7 ]
[ 89-20-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1891,vol. <2> 43,p. 359.

14
[ 2050-72-8 ]
[ 89-20-3 ]

References: [1],1878,p. 3.
Bulletin de la Societe Chimique de France,1878,vol. <2> 29,p. 499.

15
[ 5434-21-9 ]
[ 89-20-3 ]

References: [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry, Spl. 44 <1941> 450,.
Chem.Abstr.,1951,p. 1544.

16
2-methyl-1H-inden-6-amine [ No CAS ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1889,vol. 22,p. 1834.

17
[ 89-20-3 ]
[ 75-36-5 ]
[ 118-45-6 ]

References: [1]Journal of the Chemical Society,1929,p. 255.

18
[ 88-99-3 ]
[ 89-20-3 ]

References: [1]Monatshefte fur Chemie,1913,vol. 34,p. 69.
[2]Journal of the Chemical Society,1921,vol. 119,p. 1790.
[3]Monatshefte fur Chemie,1913,vol. 34,p. 69.

19
[ 88-99-3 ]
[ 89-20-3 ]
[ 56962-08-4 ]

References: [1]Journal of the Chemical Society,1929,p. 255.

20
[ 58231-16-6 ]
[ 89-20-3 ]

References: [1]Journal of the Chemical Society C: Organic,1968,p. 499 - 503.

21
[ 7504-39-4 ]
[ 89-20-3 ]

References: [1]Journal of the Chemical Society,1964,p. 2258 - 2261.
[2]Journal of the Chemical Society C: Organic,1968,p. 499 - 503.

22
[ 24127-36-4 ]
[ 89-20-3 ]

References: [1]Journal of the Chemical Society C: Organic,1969,p. 2176 - 2181.

23
[ 89-20-3 ]
[ 3306-62-5 ]
[ 4512-17-8 ]

References: [1]Monatshefte fur Chemie,1965,vol. 96,p. 1592 - 1595.

24
[ 50-84-0 ]
[ 201230-82-2 ]
[ 89-20-3 ]
[ 100-21-0 ]
[ 528-44-9 ]
[ 1967-31-3 ]
[ 74-11-3 ]

References: [1]Chemistry Letters,1986,p. 299 - 302.

25
[ 89-20-3 ]
[ 201230-82-2 ]
[ 528-44-9 ]

References: [1]Chemistry Letters,1986,p. 299 - 302.

26
[ 89-20-3 ]
[ 7147-90-2 ]

References: [1]Journal of Medicinal Chemistry,1986,vol. 29,p. 947 - 959.
[2]Journal of Organic Chemistry,1983,vol. 48,p. 2981 - 2989.

27
[ 89-20-3 ]
[ 110706-49-5 ]

Yield	Reaction Conditions	Operation in experiment
		Step 2; A solution of the previous acid (802.9 mg, 4 mmol) in tetrahydrofuran was added to a cooled (-75 C) slurry of lithium aluminum hydride, 95% (320.6 mg, 8 mmol) in tetrahydrofuran over 25 min. period. The reaction mixture was allowed to warm up to room temperature then heated to reflux for 18 hours. The reaction mixture was quenched with water, 15% sodium hydroxide, and water in ice bath. The separated organic layer was dried to yield 607.8 milligrams of 4-chlorobenzen-1,2-dimethanol.

References: [1]Synthesis,1994,p. 1035 - 1036.
[2]Chemical and Pharmaceutical Bulletin,2009,vol. 57,p. 1004 - 1007.
[3]Journal of Organic Chemistry,2014,vol. 79,p. 8143 - 8155.
[4]Patent: WO2005/123724,2005,A1 .Location in patent: Page/Page column 63.

28
[ 118-45-6 ]
[ 7732-18-5 ]
[ 89-20-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1886,vol. 233,p. 226.
Journal of the Chemical Society,1886,vol. 49,p. 518.

29
[ 7782-50-5 ]
[ 88-99-3 ]
alkali [ No CAS ]
[ 89-20-3 ]

References: [1]Chemiker-Zeitung, Chemische Apparatur,1880,vol. 4,p. 407.
Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1880,p. 862.

30
[ 7782-50-5 ]
[ 88-99-3 ]
diluted NaOH-solution [ No CAS ]
[ 89-20-3 ]
[ 56962-08-4 ]

References: [1]Journal of the Chemical Society,1929,p. 253.

31
[ 7782-50-5 ]
[ 88-99-3 ]
KOH-solution [ No CAS ]
[ 89-20-3 ]
[ 56962-08-4 ]

References: [1]Journal of the Chemical Society,1929,p. 253.

32
[ 7732-18-5 ]
[ 7782-50-5 ]
[ 88-99-3 ]
[ 89-20-3 ]
[ 56962-08-4 ]
[ 16110-99-9 ]
[ 56962-06-2 ]

References: [1]Patent: DE725605,1939, .
DRP/DRBP Org.Chem.,.

35
[ 2198-77-8 ]
[ 7697-37-2 ]
[ 89-20-3 ]

References: [1]Bulletin de la Societe Chimique de France,1881,vol. <2> 36,p. 434.

36
disodium phthalate [ No CAS ]
[ 89-20-3 ]

References: [1]Patent: US2389088,1942, .

37
trichloride of/the/ phthalic acid sulfonic acid-⁽⁴⁾ [ No CAS ]
[ 89-20-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1886,vol. 233,p. 226.
Journal of the Chemical Society,1886,vol. 49,p. 518.

38
[ 89-20-3 ]
potassium hydroxide [ No CAS ]
[ 610-35-5 ]

References: [1]Chemische Berichte,1885,vol. 18,p. 1759.

39
[ 2065-70-5 ]
[ 7697-37-2 ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1882,vol. 15,p. 320.

40
[ 56961-92-3 ]
[ 7697-37-2 ]
[ 89-20-3 ]

References: [1]Zhurnal Obshchei Khimii,1939,vol. 9,p. 1827,1829.
Chemisches Zentralblatt,1940,vol. 111,p. 2946.

41
[ 29016-72-6 ]
[ 64-19-7 ]
CrO₃ [ No CAS ]
[ 89-20-3 ]

References: [1]Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften,1888,p. 921.

42
[ 7499-06-1 ]
permanganate [ No CAS ]
[ 89-20-3 ]

References: [1]Zeitschrift fur Physikalische Chemie, Stoechiometrie und Verwandtschaftslehre,1929,vol. <A> 143,p. 18.

43
[ 35337-44-1 ]
permanganate [ No CAS ]
alkali [ No CAS ]
[ 89-20-3 ]

References: [1]Chemische Berichte,1923,vol. 56,p. 2338.

44
[ 37074-38-7 ]
[ 7732-18-5 ]
[ 7487-88-9 ]
[ 89-20-3 ]
[ 7499-07-2 ]

References: [1]Chemische Berichte,1932,vol. 65,p. 1295,1296.

45
[ 62366-66-9 ]
[ 7732-18-5 ]
[ 7647-01-0 ]
[ 89-20-3 ]

References: [1]Justus Liebigs Annalen der Chemie,1886,vol. 233,p. 226.
Journal of the Chemical Society,1886,vol. 49,p. 518.

46
[ 89-20-3 ]
[ 106-48-9 ]
[ 1220-95-7 ]

References: [1]Russian Journal of General Chemistry,2002,vol. 72,p. 255 - 258.

47
[ 89-20-3 ]
[ 7440-44-0 ]
[ 99-52-5 ]
[ 58230-68-5 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic anhydride; In ethyl acetate; toluene;	Its 4-bromo-analog melts at 208-211. The starting material is prepared as follows: The mixture of 36 g of <strong>[89-20-3]4-chlorophthalic acid</strong> and 250 ml of acetic anhydride is refluxed for 2 hours and evaporated. The residual 4-chlorophthalic anhydride is dried in a high vacuum and 27.8 g thereof refluxed in 480 ml of toluene together with 23.1 g of 4-nitro-o-toluidine for 1 day. It is cooled the precipitate filtered off, washed with benzene and dried at 80/0.1 mmHg, to yield the corresponding amide melting at 185-188. The mixture of 35 g thereof and 250 ml of acetic anhydride is refluxed for 2 hours and evaporated. The residue is dried, taken up in the minimum amount of hot ethyl acetate, the solution treated with charcoal, filtered, the filtrate cooled and the precipitate formed collected, to yield N-(4-nitro-o-tolyl)-4 chlorophthalimide melting at 221-222.
	With acetic anhydride; In ethyl acetate; toluene;	Its 4-bromo-analog melts at 208-211. The starting material is prepared as follows: The mixture of 36 g of <strong>[89-20-3]4-chlorophthalic acid</strong> and 250 ml of acetic anhydride is refluxed for 2 hours and evaporated. The residual 4-chlorophthalic anhydride is dried in a high vacuum and 27.8 g thereof refluxed in 480 ml of toluene together with 23.1 g of 4-nitro-o-toluidine for 1 day. It is cooled, the precipitate filtered off, washed with benzene and dried at 80/0.1 mmHg, to yield the corresponding amide melting at 185-188. The mixture of 35 g thereof and 250 ml of acetic anhydride is refluxed for 2 hours and evaporated. The residue is dried, taken up in the minimum amount of hot ethyl acetate, the solution treated with charcoal, filtered, the filtrate cooled and the precipitate formed collected, to yield N-(4-nitro-o-tolyl)-4-chlorophthalimide melting at 221-222.

References: [1]Patent: US3941883,1976,A .
[2]Patent: US4025505,1977,A .

48
[ 89-20-3 ]
[ 876291-65-5 ]