[ CAS No. 20776-54-9 ]

Name: 20776-54-9|2-Amino-4-iodobenzoic acid|97%
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Quality Control of [ 20776-54-9 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 20776-54-9 ]

CAS No. :	20776-54-9	MDL No. :	MFCD09800365
Formula :	C₇H₆INO₂	Boiling Point :	377°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	263.03 g/mol	Pubchem ID :	22724780
Synonyms :

Calculated chemistry of of [ 20776-54-9 ]

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 :	50.52
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) :	-6.44 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.1
Log Po/w (XLOGP3) :	2.06
Log Po/w (WLOGP) :	1.58
Log Po/w (MLOGP) :	0.8
Log Po/w (SILICOS-IT) :	1.47
Consensus Log Po/w :	1.4

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.11
Solubility :	0.206 mg/ml ; 0.000783 mol/l
Class :	Soluble
Log S (Ali) :	-3.02
Solubility :	0.252 mg/ml ; 0.000958 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.37
Solubility :	1.14 mg/ml ; 0.00432 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.63

Safety of [ 20776-54-9 ]

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

Application In Synthesis of [ 20776-54-9 ]

* 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 [ 20776-54-9 ]
Downstream synthetic route of [ 20776-54-9 ]

[ 20776-54-9 ] Synthesis Path-Upstream 1~7

1
[ 116529-62-5 ]
[ 20776-54-9 ]

Yield	Reaction Conditions	Operation in experiment
100%	With tin(ll) chloride In ethyl acetate at 20℃; for 16 h;	B. 2-Amino-4-iodo-benzoic acid. ; 4-lodo-2-nitro-benzoic acid (20 g, 68 mmol, 1.0 equiv.) was dissolved in 200 mL of EtOAc and then SnCl₂.2H₂O (46 g, 204 mmol, 3.0 equiv.) was added in three portions. The reaction mixture was stirred at rt for 16 h. Satd. aq. NaHCO₃was carefully added to adjust the mixture to pH=9. The precipitated solid was removed by filtration through diatomaceous earth, washing with water. The aqueous layer in the filtrate was separated and acidified with conc. HCl to pH=2. The precipitated solid was collected by filtration and dried to afford the title compound as white solid (19 g, 68 mmol, 100percent). ¹H NMR (400 MHz, CD₃OD): ¹H NMR (500 MHz, CDCl₃): 7.56 (d, J=8.5, 1H), 7.08 (s, 1H), 6.99 (d, J=8.5, 1H), 5.71 (br s, 2H).

Reference： [1] Patent: US2006/69286, 2006, A1, . Location in patent: Page/Page column 26
[2] American Chemical Journal, 1910, vol. 44, p. 448

2
[ 20776-50-5 ]
[ 20776-54-9 ]

Reference： [1] Patent: WO2008/154642, 2008, A2, . Location in patent: Page/Page column 182

3
[ 20780-77-2 ]
[ 20776-54-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 16, p. 7671 - 7690
[2] Proceedings of the Royal Society of London, Series B: Biological Sciences, 1958, vol. 148, p. 481,488

4
[ 118-92-3 ]
[ 20776-54-9 ]

Reference： [1] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1983, vol. 22, # 9, p. 770 - 773

5
[ 116529-62-5 ]
[ 7664-41-7 ]
[ 20776-54-9 ]

Reference： [1] American Chemical Journal, 1910, vol. 44, p. 448

6
[ 186581-53-3 ]
[ 20776-54-9 ]
[ 144550-76-5 ]

Reference： [1] Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 7033 - 7036

7
[ 67-56-1 ]
[ 20776-54-9 ]
[ 144550-76-5 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 16, p. 7671 - 7690

[ 20776-54-9 ] Synthesis Path-Downstream 1~31

1
[ 20780-77-2 ]
[ 20776-54-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2008,vol. 16,p. 7671 - 7690
[2]Proceedings of the Royal Society of London. Series B, Biological sciences,1958,vol. 148,p. 481,488

2
[ 40926-73-6 ]
[ 20776-54-9 ]
[ 75057-57-7 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 1237 - 1238

3
[ 20143-41-3 ]
[ 20776-54-9 ]
[ 75057-60-2 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 1237 - 1238

4
[ 20776-54-9 ]
[ 92970-97-3 ]

Reference： [1]Journal of the American Chemical Society,1963,vol. 85,p. 1792 - 1797

5
[ 118-92-3 ]
[ 20776-54-9 ]

Reference： [1]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1983,vol. 22,p. 770 - 773

6
[ 20776-54-9 ]
[ 35674-20-5 ]

Reference： [1]American Chemical Journal,1910,vol. 44,p. 448

7
[ 20776-54-9 ]
[ 116529-53-4 ]

Reference： [1]American Chemical Journal,1910,vol. 44,p. 448
[2]American Chemical Journal,1910,vol. 44,p. 448

8
[ 20776-54-9 ]
[ 101713-90-0 ]

Reference： [1]Proceedings of the Royal Society of London. Series B, Biological sciences,1958,vol. 148,p. 481,488

9
[ 20776-54-9 ]
[ 94428-90-7 ]

Reference： [1]Chemische Berichte,1924,vol. 57,p. 2125

10
[ 20776-54-9 ]
[ 75057-71-5 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 1237 - 1238

11
[ 20776-54-9 ]
[ 75057-65-7 ]

Reference： [1]Journal of the Indian Chemical Society,1979,vol. 56,p. 1237 - 1238

12
[ 844646-88-4 ]
[ 20776-54-9 ]
[ 844647-14-9 ]

Yield	Reaction Conditions	Operation in experiment
98%	With sodium carbonate; In water; at 20℃; for 19.0h;pH 8.0;	C. 4-lodo-2-(quinoxaline-5-sulfonylamino)-benzoic acid.; A mixture of <strong>[20776-54-9]2-amino-4-iodo-benzoic acid</strong> (10 g, 38 mmol, 1.0 equiv.) and quinoxaline-5-sulfonyl chloride (8.7 g, 38 mmol) in 100 mL of water was basified with satd. aq. Na2CO3, with stirring, to adjust the pH to 8.0. As the reaction progressed, the pH was maintained at 8.0+/-0.2 by adding satd. aq. Na2CO3. After 3 h, no further pH changes were observed. The reaction mixture was stirred at rt for another 16 h. Conc. HCl was added to adjust the pH to <2. The precipitated solid was collected by filtration, washed with water and dried to afford the title compound as white solid (17 g, 37.4 mmol, 98%). MS(ESI+): calcd. for C15H10IN3O4S, 455.0; m/z found, 456 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 14.0 (br s, 1H), 11.6 (s, 1H), 9.10 (d, J=1.5, 1H), 9.97 (d, J=1.5, 1H), 8.60 (d, J=7.4, 1H), 8.42 (d, J=8.4, 1H), 8.06 (t, J=7.5, 1H), 7.95 (d, J=1.2, 1,H), 7.51 (d, J=8.3, 1H), 7.37 (dd, J=8.3, 1.2, 1H).

Reference： [1]Patent: US2006/69286,2006,A1 .Location in patent: Page/Page column 27

13
[ 20776-54-9 ]
S-acetyl-4-iodothiosalicylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		(a) The S-acetyl-4-iodothiosalicylic acid, m.p. 184-186, was prepared from <strong>[20776-54-9]4-iodoanthranilic acid</strong> according to the procedure described in Example 33 (a). Calcd for C9 H7 103 S: C, 33.55; H, 2.19; I, 39.40; S, 9.95%. Found: C, 33.70; H, 2.23; I, 39.20; S, 10.09%.

Reference： [1]Patent: US4221800,1980,A

14
[ 20776-54-9 ]
methyl (S)-2-amino-3-tert-butoxycarbonylaminopropanoate hydrochloride [ No CAS ]
[ 1093191-11-7 ]

Yield	Reaction Conditions	Operation in experiment
	With O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In acetonitrile; for 0.5h;	(S)-methyl 2-(2-amino-4-iodobenzamido)-3-(tert-butoxycarbonylamino)propanoate (4). To a solution of <strong>[20776-54-9]2-amino-4-iodobenzoic acid</strong> (2) (0.98g, 3.37 mmol), DAP hydrochloride methyl ester (compound 3) (0.952g, 3.74mmol), DIEA (2 mL, excess) in acetonitrile (26mL) was added HATU (1.42g, 3.74mmol). The reaction mixture was stirred for 30 min and concentrated. The crude product extracted with ethyl acetate (20OmL) and concentrated to give (4) and used as such in the next step.

Reference： [1]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 182

15
[ 20776-50-5 ]
[ 20776-54-9 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; potassium iodide; In N,N-dimethyl-formamide; at 130℃; for 18.0h;Sealed tube;	2-amino-4-iodobenzoic acid (2). A solution of 2-amino-4-bromobenzoic acid (1) (2.15g, 10 mmol) in degassed DMF (25ml), CuI (3.8Og, 20 mmol) and KI (8.8g, 50 mmol) was heated in a sealed tube at 13OC for 18h. The reaction mixture was cooled to room temperature and solid was filtered off. The filtrate was concentrated to dryness and the residue was stirred in ethyl acetate (400ml) and water (100ml) and the organic layer was separated and concentrated. The crude product was then purified over a silica gel column to give (2) (0.98g).

Reference： [1]Patent: WO2008/154642,2008,A2 .Location in patent: Page/Page column 182

16
[ 20776-54-9 ]
[ 1241915-20-7 ]

Yield	Reaction Conditions	Operation in experiment
52%	With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	[00313] Step A: To a solution of <strong>[20776-54-9]2-amino-4-iodobenzoic acid</strong> (2.5 g, 9.50 mmol) in DMF (10 mL) at rt under argon were added EDCI (2.18 g, 11.40 mmol), 1 - hydroxybenzotriazole (1.54 g, 11.40 mmol), DIEA (1.98 mL, 11.40 mmol), and ammonia (7.0 N solution in MeOH; 1.90 mL, 13.30 mmol). The dark solution was stirred at rt overnight and diluted with H2O until precipitate formed. The precipitate was separated by filtration, washed with H2O, and dried under high vacuum for several hours to afford 2-amino-4-iodobenzamide as a tan solid (1.3 g, 52%). LC-MS (ESI) m/z 263 (M + H)+.
	With DIEA; ammonia; benzotriazol-1-ol; In methanol; N,N-dimethyl-formamide;	Step A: To a solution of <strong>[20776-54-9]2-amino-4-iodobenzoic acid</strong> (2.5 g, 9.50 mmol) in DMF (10 mL) at room temperature under argon were added EDCI (2.18 g, 11.40 mmol), 1-hydroxybenzotriazole (1.54 g, 11.40 mmol), DIEA (1.98 mL, 11.40 mmol), and ammonia (7.0 N solution in MeOH, 1.90 mL, 13.30 mmol). The dark solution was stirred at room temperature overnight and diluted with H2O until precipitate formed. The precipitate was separated by filtration, washed with H2O, and dried under high vacuum for several hours to afford 2-amino-4-iodobenzamide as a tan solid (1.3 g, 52%). LC-MS (ESI) m/z 263 (M+H)+.

Reference： [1]Patent: WO2010/99379,2010,A1 .Location in patent: Page/Page column 108
[2]Patent: US2012/53176,2012,A1
[3]Phosphorus, Sulfur and Silicon and the Related Elements,2020,vol. 195,p. 194 - 200

17
[ 22532-61-2 ]
[ 20776-54-9 ]
C₁₄H₉BrINO₃ [ No CAS ]

Reference： [1]E-Journal of Chemistry,2010,vol. 7,p. 882 - 886

18
[ 20776-54-9 ]
[ 1241915-19-4 ]

Reference： [1]Patent: US2012/53176,2012,A1

19
[ 20776-54-9 ]
[ 1241915-21-8 ]

Reference： [1]Patent: US2012/53176,2012,A1

20
[ 20776-54-9 ]
[ 1241915-22-9 ]

Reference： [1]Patent: US2012/53176,2012,A1

21
[ 20776-54-9 ]
[ 1241915-23-0 ]

Reference： [1]Patent: US2012/53176,2012,A1

22
[ 20776-54-9 ]
[ 1241915-24-1 ]

Reference： [1]Patent: US2012/53176,2012,A1

23
[ 20776-54-9 ]
[ 55496-54-3 ]
[ 1449276-39-4 ]