[ CAS No. 847685-01-2 ] {[proInfo.proName]}

Name: 847685-01-2|4,5-Difluoro-2-iodoaniline|95%
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SKU: A106013
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Quality Control of [ 847685-01-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 847685-01-2 ]

SDS Specification

Alternatived Products of [ 847685-01-2 ]

Product Details of [ 847685-01-2 ]

CAS No. :	847685-01-2	MDL No. :	MFCD03095321
Formula :	C₆H₄F₂IN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XBOMEOMTVVEEDW-UHFFFAOYSA-N
M.W :	255.00	Pubchem ID :	12181913
Synonyms :

Calculated chemistry of [ 847685-01-2 ]

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) :	1.76
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 :	2.61

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 :	2.05

Safety of [ 847685-01-2 ]

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

Application In Synthesis of [ 847685-01-2 ]

* 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 [ 847685-01-2 ]
Downstream synthetic route of [ 847685-01-2 ]

[ 847685-01-2 ] Synthesis Path-Upstream 1~2

1
[ 847685-01-2 ]
[ 169674-01-5 ]

Reference： [1] Tetrahedron Letters, 2005, vol. 46, # 6, p. 907 - 910

2
[ 3863-11-4 ]
[ 847685-01-2 ]

Yield	Reaction Conditions	Operation in experiment
97%	With iodine; sodium hydrogencarbonate In water at 20℃; for 0.5 h;	3,4-Difluoroaniline (645mg, 5mmol) was suspended in water (25 mL). Sodium bicarbonate (630 mg, 7.5 mmol) was added and then iodine (1.65 g, 6.5 mmol). The reaction mixture was stirred vigorously at ambient temperature for 30min and then poured into saturated sodium thiosulphate solution (50 mL) and extracted with ethyl acetate (2x25 mL). The combined extracts were washed with sodium thiosulphate (20 mL), water (20 mL) and brine (20 mL), dried (MgSO₄) and evaporated to give the title compound as a dark oil. (1.24g, 97percent).
69%	With N-iodo-succinimide In dichloromethane at 20℃; Inert atmosphere	At room temperature, a solution of 3,4-difluoroaniline (100 μL, 1 mmol) and N-iodosuccinimide (225 mg, 1 mmol) in anhydrous dichloromethane (4 mL) was stirred overnight under argon atmosphere. Then an aqueous solution of sodium sulfite was added and the reaction mixture was extracted with dichloromethane. The combined organic extracts were dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography (silica gel, cyclohexane/ethyl acetate, 1/0 to 8/2) to afford 4,5-difluoro-2-iodoaniline (175 mg, 69percent) as a red oil. ESI-MS m/z 255.9 (M+H)⁺.
12 g	With iodine; sodium hydrogencarbonate In water at 20℃; for 1 h;	Reference Example 3a 2-methyl-5,6-fluoro-2,3-dihydro-1H-indole Step 1a:4,5-Difluoro-2-iodoaniline 16.5 g of iodine and 6.3 g of sodium bicarbonate are added, at ambient temperature, to a suspension of 6.45 g of 3,4-difluoroaniline in 250 ml of water. The reaction medium is stirred at ambient temperature for 1 hour.A saturated sodium thiosulfate solution is added and then the resulting mixture is extracted 3 times with ethyl acetate. The organic phases are combined, dried over magnesium sulfate, filtered, and then concentrated under reduced pressure, so as to give 12 g of 4,5-difluoro-2-iodoainiline, the characteristics of which are the following:Mass spectrometry: method ARetention time Tr (min)=0.90; [M+H]+: m/z 256; base peak: m/z 297

Reference： [1] Patent: WO2006/82400, 2006, A1, . Location in patent: Page/Page column 55
[2] Tetrahedron Letters, 2005, vol. 46, # 6, p. 907 - 910
[3] Organic Letters, 2008, vol. 10, # 13, p. 2657 - 2659
[4] Patent: EP2141164, 2010, A1, . Location in patent: Page/Page column 44
[5] Journal of Fluorine Chemistry, 2012, vol. 135, p. 97 - 107
[6] Patent: US2013/274253, 2013, A1, . Location in patent: Paragraph 1281-1286
[7] Synthesis (Germany), 2018, vol. 50, # 3, p. 555 - 564

[ 847685-01-2 ] Synthesis Path-Downstream 1~39

1
[ 79-22-1 ]
[ 847685-01-2 ]
[ 847685-02-3 ]