[ CAS No. 155906-13-1 ] {[proInfo.proName]}

Name: 155906-13-1|2,5-Difluoro-4-iodoaniline|98%
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Quality Control of [ 155906-13-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 155906-13-1 ]

Product Details of [ 155906-13-1 ]

CAS No. :	155906-13-1	MDL No. :	MFCD07774188
Formula :	C₆H₄F₂IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DQTJNHXTFILGGG-UHFFFAOYSA-N
M.W :	255.00	Pubchem ID :	18960027
Synonyms :

Calculated chemistry of [ 155906-13-1 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.48
TPSA :	26.02 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) :	-6.37 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.72
Log Po/w (XLOGP3) :	2.09
Log Po/w (WLOGP) :	3.0
Log Po/w (MLOGP) :	3.26
Log Po/w (SILICOS-IT) :	2.95
Consensus Log Po/w :	2.6

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.18
Solubility :	0.168 mg/ml ; 0.000658 mol/l
Class :	Soluble
Log S (Ali) :	-2.27
Solubility :	1.38 mg/ml ; 0.00541 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.55
Solubility :	0.0717 mg/ml ; 0.000281 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	3.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.14

Safety of [ 155906-13-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H320-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 155906-13-1 ]

* 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.

Upstream synthesis route of [ 155906-13-1 ]
Downstream synthetic route of [ 155906-13-1 ]

[ 155906-13-1 ] Synthesis Path-Upstream 1~2

1
[ 367-30-6 ]
[ 155906-13-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iodine; sodium hydrogencarbonate In water at 20℃; for 2 h;	A mixture of 2,5-difluoroaniline (0.5 g, 3.9 mmol), NaHCO₃ (0.8 g, 9.8 mmol), I₂ (2.5 g, 9.8 mmol) and H₂O (50 mL) was stirred at r.t. for 2 h. Than Na₂SO₃ (1 g, 8 mmol) was added, and the reaction mixture was extracted with CH₂Cl₂ (2×50 mL). The combined organic layers were washed with H₂O (50 mL), dried (MgSO₄) and purified by flash chromatography on Al₂O₃. Evaporation of the solvent was performed in vacuo to obtain 6b (0.9 g, 91 percent) as brown solid (the ¹H and ¹³C NMR spectra closely agree with the literature data [37]); ν_max (KBr): 3464, 3379, 3042, 2926, 2855, 1632, 1501, 1414, 1323, 1298, 1234, 1184, 1167, 864, 837, 795, 733, 596, 444 cm⁻¹; ¹H NMR (500.13 MHz, CDCl₃): δ=7.27 (dd, 1H, J_H3,_F2=9.9, J_H3,_F5=5.6 Hz, H³), 6.52 (d, 1H, J_H6,_F5=8.7, J_H6,_F2=7.7 Hz, H⁶), 3.91 (br s, 2H, NH₂); ¹³C NMR (125.76 MHz, CDCl₃): δ=158.0 (d, ¹J_C5,_F5=239.1 Hz, C⁵), 147.4 (d, ¹J_C2,_F2=239.6Hz, C²), 135.7 (dd, ²J_C1,_F2=14.7, ³J_C1,_F5=10.6 Hz, C¹), 123.8 (dd, ²J_C3,_F2=22.8, ³J_C3,_F5=3.5Hz, C³), 102.7 (dd, ²J_C6,_F5=29.9, ³J_C6,_F2=3.7 Hz, C⁶), 62.8 (dd, ²J_C4,_F5=29.1, ³J_C4,_F2=8.1 Hz, C⁴); ¹⁹F NMR (282.37 MHz, CDCl₃): δ=−101.5 (ddd, 1F, J_F5,_F2=13.4, J_F5,_H6=8.7, J_F5,_H3=5.6 Hz, F⁵), −140.0 (ddd, 1F, J_F2,_F5=13.4, J_F2,_H3=9.9, J_F2,_H6=7.7 Hz, F²); HRMS (EI): ⁺, found 254.9356. C₆H₄F₂IN requires 254.9351.

Reference： [1] Journal of Fluorine Chemistry, 2016, vol. 188, p. 85 - 98
[2] Canadian Journal of Chemistry, 2000, vol. 78, # 8, p. 1081 - 1088
[3] Patent: US5356558, 1994, A,
[4] Synthesis (Germany), 2018, vol. 50, # 3, p. 555 - 564

2
[ 112279-60-4 ]
[ 155906-13-1 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 24, p. 11031 - 11041

[ 155906-13-1 ] Synthesis Path-Downstream 1~24

1
[ 155906-13-1 ]
[ 320592-17-4 ]
[ 320592-23-2 ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 9214 - 9219

2
[ 367-30-6 ]
[ 155906-13-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With iodine; sodium hydrogencarbonate; In water; at 20℃; for 2.0h;	A mixture of 2,5-difluoroaniline (0.5 g, 3.9 mmol), NaHCO3 (0.8 g, 9.8 mmol), I2 (2.5 g, 9.8 mmol) and H2O (50 mL) was stirred at r.t. for 2 h. Than Na2SO3 (1 g, 8 mmol) was added, and the reaction mixture was extracted with CH2Cl2 (2×50 mL). The combined organic layers were washed with H2O (50 mL), dried (MgSO4) and purified by flash chromatography on Al2O3. Evaporation of the solvent was performed in vacuo to obtain 6b (0.9 g, 91 %) as brown solid (the 1H and 13C NMR spectra closely agree with the literature data [37]); numax (KBr): 3464, 3379, 3042, 2926, 2855, 1632, 1501, 1414, 1323, 1298, 1234, 1184, 1167, 864, 837, 795, 733, 596, 444 cm-1; 1H NMR (500.13 MHz, CDCl3): delta=7.27 (dd, 1H, JH3,F2=9.9, JH3,F5=5.6 Hz, H3), 6.52 (d, 1H, JH6,F5=8.7, JH6,F2=7.7 Hz, H6), 3.91 (br s, 2H, NH2); 13C NMR (125.76 MHz, CDCl3): delta=158.0 (d, 1JC5,F5=239.1 Hz, C5), 147.4 (d, 1JC2,F2=239.6Hz, C2), 135.7 (dd, 2JC1,F2=14.7, 3JC1,F5=10.6 Hz, C1), 123.8 (dd, 2JC3,F2=22.8, 3JC3,F5=3.5Hz, C3), 102.7 (dd, 2JC6,F5=29.9, 3JC6,F2=3.7 Hz, C6), 62.8 (dd, 2JC4,F5=29.1, 3JC4,F2=8.1 Hz, C4); 19F NMR (282.37 MHz, CDCl3): delta=-101.5 (ddd, 1F, JF5,F2=13.4, JF5,H6=8.7, JF5,H3=5.6 Hz, F5), -140.0 (ddd, 1F, JF2,F5=13.4, JF2,H3=9.9, JF2,H6=7.7 Hz, F2); HRMS (EI): +, found 254.9356. C6H4F2IN requires 254.9351.
	With pyridine; Iodine monochloride; In chloroform; water; acetic acid;	Step 3: 2,5-Difluoroaniline (38 g) was dissolved in acetic acid (120 ml), and then pyridine (25 g) was added thereto, followed by stirring. A mixed solution of iodine monochloride (50 g) with acetic acid (30 ml) was added dropwise thereto. After stirring at room temperature for 1 hour, the mixed solution was further stirred at 70 to 80 C. for 2 hours. Then, the reaction solution was poured into water, and the precipitated crystals were filtered, followed by washing with water. The resulting crystals were dissolved in chloroform, and then washed with water twice, further with 10% potassium hydroxide aqueous solution twice, and furthermore with water twice, followed by distilled off chloroform therefrom. The residue was distilled under reduced pressure (b.p. 130 to 140 C./20 mmHg), and then recrystallized from methanol, to give 4-iodo-2,5-difluoroaniline (50 g).

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98
[2]Canadian Journal of Chemistry,2000,vol. 78,p. 1081 - 1088
[3]Patent: US5356558,1994,A
[4]Synthesis,2018,vol. 50,p. 555 - 564

3
[ 173327-56-5 ]
[ 155906-13-1 ]
(2R,5R)-5-(4-Amino-2,5-difluoro-phenyl)-2-(tert-butyl-dimethyl-silanyloxymethyl)-dihydro-furan-3-one [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2000,vol. 78,p. 1081 - 1088

4
[ 155906-13-1 ]
[ 307306-10-1 ]

Reference： [1]Canadian Journal of Chemistry,2000,vol. 78,p. 1081 - 1088

5
[ 155906-13-1 ]
2,5-difluoro-4-[1-(2-deoxy-β-D-ribofuranosyl)]aniline [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2000,vol. 78,p. 1081 - 1088

6
copper bromide [ No CAS ]
[ 155906-13-1 ]
2-bromo-1,4-difluoro-4-iodobenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen bromide; acetic acid; sodium nitrite; In sulfuric acid; water;	Step 4: Sodium nitrite (19 g) was dissolved in sulfuric acid (148 ml), and then acetic acid (170 ml) was added thereto at 10 C. or lower. The mixed solution was kept at 20 to 25 C., and <strong>[155906-13-1]4-iodo-2,5-difluoroaniline</strong> (50 g) was added thereto for 1 hour, followed by stirring for 2 hours. The reaction solution was added dropwise to a mixed solution of copper bromide (49 g) with 48% hydrobromic acid (142 ml), and stirred overnight. Then, water (300 ml) was added to the solution, and the resulting solution was extracted with chloroform, followed by washing with water 3 times. After distilling off chloroform, the resultant was recrystallized from methanol to give 2-bromo-1,4-difluoro-4-iodobenzene (45 g).

Reference： [1]Patent: US5356558,1994,A

7
[ 124-63-0 ]
[ 155906-13-1 ]
[ 910487-20-6 ]

Yield	Reaction Conditions	Operation in experiment
87%	With pyridine; In dichloromethane; at 20℃; for 24.0h;	60A) N-(2,5-Difluoro-4-iodophenyl)methanesulfonamide To a solution of <strong>[155906-13-1]2,5-difluoro-4-iodoaniline</strong> (5.3 g, 19.4 mmol, Can. J. Chem., 2000(78), 1081-1088) in DCM(50 ml) was added methanesulfonyl chloride (1.65 ml, 21.3 mmol) and pyridine (4.7 ml, 58.2 mmol) at 0 C. The mixture was stirred for 24 hours at room temperature. The mixture was partitionedbetween EtOAc and 2 M HCl aqueous solution. The organic layer was separated and washed with 2 M aqueous HCl solution and brine, dried over sodium sulfate and concentrated in vacuo. The crude puroduct was purified by silica gel column chromatography eluding with gradually from hexane/EtOAc (4:1) to hexane/EtOAc (3:1) to give the title compound (5.6 g, 87%) as purple solids. 1H NMR (270 MHz, CDCl3) delta 3.09 (3H, s), 6.81 (1H, br s), 7.39 (1H, dd, J=6.9, 8.2 Hz), 7.53 (1H, dd, J=5.3, 9.2 Hz). MS (ESI) m/z 332 (M-H)-.

Reference： [1]Patent: US2006/211741,2006,A1 .Location in patent: Page/Page column 64

8
[ 112279-60-4 ]
[ 155906-13-1 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 11031 - 11041

9
[ 155906-13-1 ]
1-oxa-2,8-diazaspiro[4.5]dec-2-ene-3-carboxylic acid (2,5-difluoro-4-methylsulfanylphenyl)amide hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 11031 - 11041

10
[ 155906-13-1 ]
[ 1415730-99-2 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 11031 - 11041

11
[ 155906-13-1 ]
[ 1415731-00-8 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 11031 - 11041

12
[ 624-92-0 ]
[ 155906-13-1 ]
[ 1415731-01-9 ]

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 11031 - 11041

13
[ 155906-13-1 ]
4,4'-(buta-1,3-diyne-1,4-diyl)bis(2,5-difluoroaniline) [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98
[2]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98
[3]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98
[4]Journal of Fluorine Chemistry,2016,vol. 188,p. 85 - 98

14
[ 155906-13-1 ]
2,5-difluoro-4-(4,5,7-trifluoro-1H-indol-2-yl)aniline [ No CAS ]