[ CAS No. 21961-30-8 ] {[proInfo.proName]}

Name: 21961-30-8|3-Amino-5-chlorobenzoic acid|98%
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Quality Control of [ 21961-30-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 21961-30-8 ]

CAS No. :	21961-30-8	MDL No. :	MFCD02183894
Formula :	C₇H₆ClNO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	ATFAXWNNFCBZNY-UHFFFAOYSA-N
M.W :	171.58	Pubchem ID :	10986726
Synonyms :

Calculated chemistry of [ 21961-30-8 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	42.82
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.15 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.11
Log Po/w (XLOGP3) :	1.69
Log Po/w (WLOGP) :	1.63
Log Po/w (MLOGP) :	0.48
Log Po/w (SILICOS-IT) :	1.14
Consensus Log Po/w :	1.21

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-2.31
Solubility :	0.848 mg/ml ; 0.00494 mol/l
Class :	Soluble
Log S (Ali) :	-2.63
Solubility :	0.398 mg/ml ; 0.00232 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.02
Solubility :	1.63 mg/ml ; 0.00948 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.24

Safety of [ 21961-30-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 21961-30-8 ]

* 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 [ 21961-30-8 ]
Downstream synthetic route of [ 21961-30-8 ]

[ 21961-30-8 ] Synthesis Path-Upstream 1~5

1
[ 34662-36-7 ]
[ 21961-30-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen In ethanol; water at 20℃; for 18 h;	3-Chloro-5-nitro-benzoic acid (1.590g, 7. [9MMOL)] was stirred under a hydrogen atmosphere in ethanol (40mL) with raney-nickel, (aqueous suspension,-0. 4g) at room temperature and pressure for 18 hours. The reaction mixture was then filtered through celite and evaporated to give the title compound (1.300g, 96percent). [OH] NMR [(400MHZ,] [CDCI3)] 6.86 (1H, s), 7.18 [(1H,] s), 7.22 (1H, s). LC/MS t=2.30 mins [[MH-]] 170.
368 mg	With iron; ammonium chloride In water; isopropyl alcohol at 90℃; for 3 h;	Isopropanol (78 mL),Ammonium chloride (0.18 g) and reduced iron (1.07 g) were added to a mixed solution of water (20 mL)After stirring at 90 ° C. for 1 hour,3-Chloro-5-nitrobenzoic acid (Compound 0004-1, 1.1 g) was slowly added and stirred at 90 ° C. for 3 hours.The reaction solution was cooled to room temperature, washed with methanol, and the filtrate was evaporated under reduced pressure to obtain a crude product. Purification by silica gel column chromatography (methanol-chloroform) gave 3-amino-5-chlorobenzoic acid (Compound 0004-2, 368 mg) as a light brown solid.

Reference： [1] Patent: WO2003/101959, 2003, A1, . Location in patent: Page 225-226
[2] Justus Liebigs Annalen der Chemie, 1884, vol. 222, p. 73[3] Justus Liebigs Annalen der Chemie, 1881, vol. 208, p. 312
[4] Journal of the American Chemical Society, 1954, vol. 76, p. 6336,6337
[5] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4557 - 4561
[6] Patent: JP6052673, 2016, B2, . Location in patent: Paragraph 0082

2
[ 535-80-8 ]
[ 21961-30-8 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4557 - 4561
[2] Patent: JP6052673, 2016, B2,

3
[ 58123-67-4 ]
[ 21961-30-8 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 1915

4
[ 21961-30-8 ]
[ 289039-25-4 ]

Reference： [1] Journal of the Chemical Society, 1928, p. 1915

5
[ 67-56-1 ]
[ 21961-30-8 ]
[ 21961-31-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	at 0℃; for 12 h; Reflux	Example 149 N- [7-Chloro-3 ,3 -dimethyl-2- (3 -morpholin-4-yl-phenyl)- 1 ,2,3 ,4-tetrahydro-quinoline- 5-carbonyl] -methanesulfonamide To a stirred solution of 3-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropewise at 0 °C . Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3 x 100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-5-chloro- benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C₈H₈C1N0₂ (M+H)⁺: 186.61, observed: 185.9
100%	at 0℃; for 12 h; Reflux	To a stirred solution of 3-amino-5-chloro-benzoic acid (50 g, 291 mmol) in methanol (300 mL) was added thionyl chloride (45 mL, 605 mmol) dropewise at 0° C. Then the mixture solution was refluxed for 12 hours before cooling to room temperature. Then the reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (500 mL), washed with saturated aqueous sodium bicarbonate solution (3.x.100 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3-amino-5-chloro-benzoic acid methyl ester (54 g, quant.) as a pale-white solid: LC/MS m/e calcd for C₈H₈ClNO₂(M+H)⁺: 186.61, observed: 185.9.

Reference： [1] Patent: WO2011/128251, 2011, A1, . Location in patent: Page/Page column 245-246
[2] Patent: US2011/257151, 2011, A1, . Location in patent: Page/Page column 91

[ 21961-30-8 ] Synthesis Path-Downstream 1~27

1
[ 34662-36-7 ]
[ 21961-30-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With hydrogen;nickel; In ethanol; water; at 20℃; under 760.051 Torr; for 18h;	3-Chloro-5-nitro-benzoic acid (1.590g, 7. [9MMOL)] was stirred under a hydrogen atmosphere in ethanol (40mL) with raney-nickel, (aqueous suspension,-0. 4g) at room temperature and pressure for 18 hours. The reaction mixture was then filtered through celite and evaporated to give the title compound (1.300g, 96%). [OH] NMR [(400MHZ,] [CDCI3)] 6.86 (1H, s), 7.18 [(1H,] s), 7.22 (1H, s). LC/MS t=2.30 mins [[MH-]] 170.
368 mg	With iron; ammonium chloride; In water; isopropyl alcohol; at 90℃; for 3h;	Isopropanol (78 mL),Ammonium chloride (0.18 g) and reduced iron (1.07 g) were added to a mixed solution of water (20 mL)After stirring at 90 C. for 1 hour,3-Chloro-5-nitrobenzoic acid (Compound 0004-1, 1.1 g) was slowly added and stirred at 90 C. for 3 hours.The reaction solution was cooled to room temperature, washed with methanol, and the filtrate was evaporated under reduced pressure to obtain a crude product. Purification by silica gel column chromatography (methanol-chloroform) gave 3-amino-5-chlorobenzoic acid (Compound 0004-2, 368 mg) as a light brown solid.

Reference： [1]Patent: WO2003/101959,2003,A1 .Location in patent: Page 225-226
[2]Justus Liebigs Annalen der Chemie,1884,vol. 222,p. 73
Justus Liebigs Annalen der Chemie,1881,vol. 208,p. 312
[3]Journal of the American Chemical Society,1954,vol. 76,p. 6336,6337
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 4557 - 4561
[5]Patent: JP6052673,2016,B2 .Location in patent: Paragraph 0082

2
[ 21961-30-8 ]
[ 289039-25-4 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1915

3
[ 58123-67-4 ]
[ 21961-30-8 ]

Reference： [1]Journal of the Chemical Society,1928,p. 1915

4
[ 21961-30-8 ]
[ 105-34-0 ]
3-chloro-5-(2-cyano-acetylamino)-benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 1727 - 1736

5
[ 21961-30-8 ]
3-chloro-5-(2-cyano-3-{2-[3-(1<i>H</i>-imidazol-2-ylsulfanyl)-propoxy]-phenyl}-acryloylamino)-benzoic acid [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,1999,vol. 7,p. 1727 - 1736

6
[ 632625-92-4 ]
[ 21961-30-8 ]
3-{2-[5-chloro-2-(2,4-difluorobenzyloxy)phenyl]-5-methyl-pyrrol-1-yl}-5-chlorobenzoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With powdered 4 A molecular sieves;toluene-4-sulfonic acid; In 1-methyl-pyrrolidin-2-one; toluene; for 18h;Heating / reflux;	[1- [5-CHLORO-2- (2, 4-DIFLUORO-BENZYLOXY)-PHENYL]] pentane-1,4-dione (176mg, 0. [5MMOL)] was heated at reflux in toluene (2.0 mL), containing NMP (0.5mL), with 3-amino-5-chloro- benzoic acid (86mg, 0. [5MMOL),] [PTSA] (cat. ) and powdered 4A molecular sieves (0.8mg) for 18 hours. Upon cooling, the mixture was filtered through celite and washed with EtOAc (10mL). The filtrate was washed with brine, dried (MgSO4), filtered and evapoated to an oil which was purified on a Water's sep-pack [(10G)] with [ET2O/ISO-HEXANE] to give the title compound [(170MG,] 70%). ['H] NMR [(400MHZ,] [CDCI3)] 2.16 (3H, s), 4.75 (2H, s), 6.13 [(1H,] d, J=3Hz), 6.27 (1H, d, J=3Hz), 6.66 (1H, d, J=9Hz), 6.73-6. 87 (2H, m), 6.98-7. 06 (1H, m), 7.10-7. 19 (2H, m), 7.25 (1 H, s), 6,60 [(1 H, BR S),] 7.93 (1 H, br s). LC/MS t=4.40 min [[MH+]] 488.

Reference： [1]Patent: WO2003/101959,2003,A1 .Location in patent: Page 226

7
[ 21961-30-8 ]
[ 1098591-90-2 ]

Yield	Reaction Conditions	Operation in experiment
		Standard aromatic ring chemistry is used to prepare the known starting material, <strong>[21961-30-8]3-amino-5-chloro-benzoic acid</strong> (CAS No.21961-30-8). This compound is nitrated under standard conditions, and the desired 4-nitro regioisomer is isolated via silica gel chromatography.

Reference： [1]Patent: US2004/6104,2004,A1 .Location in patent: Page/Page column 20 - 21

8
[ 21961-30-8 ]
3-Amino-5-chlorobenzoylguanidine dihydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 8 3-Amino-5-chlorobenzoylguanidine dihydrochloride is obtained according to the general procedure from <strong>[21961-30-8]3-amino-5-chlorobenzoic acid</strong>. Crystalline substance; m.p. 270 C.

Reference： [1]Patent: US5516805,1996,A

Yield	Reaction Conditions	Operation in experiment
		Examples of some specific acids that can be converted to diphosphonates of formula R--Z according to any of the foregoing procedures are the following: ... p-aminobenzoic acid, 3-chloro-4-aminobenzoic acid, 2-chloro-4-aminobenzoic acid, 2-chloro-5-aminobenzoic acid, and 3-chloro-5-aminobenzoic acid,

10
[ 21961-30-8 ]
[ 1343461-17-5 ]