[ CAS No. 660-49-1 ] {[proInfo.proName]}

Name: 660-49-1|3-Fluoro-5-iodoaniline|97%
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Quality Control of [ 660-49-1 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 660-49-1 ]

Product Details of [ 660-49-1 ]

CAS No. :	660-49-1	MDL No. :	MFCD04116466
Formula :	C₆H₅FIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	237.01	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 660-49-1 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	43.52
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.69
Log Po/w (XLOGP3) :	1.99
Log Po/w (WLOGP) :	2.44
Log Po/w (MLOGP) :	2.84
Log Po/w (SILICOS-IT) :	2.53
Consensus Log Po/w :	2.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.06
Solubility :	0.208 mg/ml ; 0.000878 mol/l
Class :	Soluble
Log S (Ali) :	-2.16
Solubility :	1.63 mg/ml ; 0.00688 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.27
Solubility :	0.126 mg/ml ; 0.000532 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.08

Safety of [ 660-49-1 ]

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 [ 660-49-1 ]

* 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 [ 660-49-1 ]
Downstream synthetic route of [ 660-49-1 ]

[ 660-49-1 ] Synthesis Path-Upstream 1~4

1
[ 3819-88-3 ]
[ 660-49-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tin(II) chloride dihdyrate In ethanol for 1.5 h; Reflux	Example 2Synthesis of 3-fluoro-5-iodo-N,N-dimethylaniline (VMY-2-119): The suspension of l-fluoro-3-iodo-5 -nitrobenzene (0.5 g, 1.87 mmol) and SnCl₂'2H₂0 (1.5 g, 6.64 mmol) in EtOH (10 mL) was heated to reflux for 1.5 h. The solvent was removed and the crude mixture was diluted with ether, washed with 4 N NaOH and brine. The ether layer was- 42 -B4067₂89v₂ separated and dried over Na₂S0₄, filtered, concentrated to yield amine compound as a solid (0.4 g, 91percent). The crude product was used without purification.A solution of above amine (0.4 g, 1.69 mmol) and iodomethane (0.719 g, 5 mmol) in dimethylformamide (DMF; 10 mL) containing potassium carbonate (0.46 g, 3.38 mmol) was stirred for 48 h at room temperature. Water (lOmL) was then added and the solution was extracted with ether three times. The organic extracts washed with water, brine, dried over Na₂S0₄, filtered and concentrated. The crude product was purified by column chromatography to yield VMY-2-119 as a liquid (0.23 g, 52percent). 1H NMR (399 MHz) ? 6.69 - 6.63 (m, 2H), 6.22 (dt, J = 12.5, 2.3, 1H), 2.83 (s, 6H). ¹³C NMR (100 MHz) ? 163.33(d, JF-C=245 Hz), 152.49(d, J=l lHz) 116.91 (d, J = 2.4), 112.12(d, J=24 Hz), 98.73(d, J=26Hz), 94.24(d, J=l l Hz), 40.21 (s, 3H).

Reference： [1] Patent: WO2013/71067, 2013, A1, . Location in patent: Page/Page column 42-43
[2] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 2, p. 153 - 163
[3] Journal of Organic Chemistry, 1960, vol. 25, p. 1342 - 1348
[4] Patent: EP1382603, 2004, A1, . Location in patent: Page 170
[5] Patent: US6821980, 2004, B1, . Location in patent: Page column 40-41
[6] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8404 - 8421

2
[ 99-65-0 ]
[ 660-49-1 ]

Reference： [1] Journal of Organic Chemistry, 1960, vol. 25, p. 1342 - 1348

3
[ 10394-64-6 ]
[ 660-49-1 ]

Reference： [1] Journal of Organic Chemistry, 1960, vol. 25, p. 1342 - 1348

4
[ 6276-04-6 ]
[ 660-49-1 ]

Reference： [1] Journal of Organic Chemistry, 1960, vol. 25, p. 1342 - 1348

[ 660-49-1 ] Synthesis Path-Downstream 1~25

1
[ 3819-88-3 ]
[ 660-49-1 ]

Yield	Reaction Conditions	Operation in experiment
91%	With tin(II) chloride dihdyrate; In ethanol; for 1.5h;Reflux;	Example 2Synthesis of 3-fluoro-5-iodo-N,N-dimethylaniline (VMY-2-119): The suspension of l-fluoro-3-iodo-5 -nitrobenzene (0.5 g, 1.87 mmol) and SnCl2'2H20 (1.5 g, 6.64 mmol) in EtOH (10 mL) was heated to reflux for 1.5 h. The solvent was removed and the crude mixture was diluted with ether, washed with 4 N NaOH and brine. The ether layer was- 42 -B4067289v2 separated and dried over Na2S04, filtered, concentrated to yield amine compound as a solid (0.4 g, 91%). The crude product was used without purification.A solution of above amine (0.4 g, 1.69 mmol) and iodomethane (0.719 g, 5 mmol) in dimethylformamide (DMF; 10 mL) containing potassium carbonate (0.46 g, 3.38 mmol) was stirred for 48 h at room temperature. Water (lOmL) was then added and the solution was extracted with ether three times. The organic extracts washed with water, brine, dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography to yield VMY-2-119 as a liquid (0.23 g, 52%). 1H NMR (399 MHz) ? 6.69 - 6.63 (m, 2H), 6.22 (dt, J = 12.5, 2.3, 1H), 2.83 (s, 6H). 13C NMR (100 MHz) ? 163.33(d, JF-C=245 Hz), 152.49(d, J=l lHz) 116.91 (d, J = 2.4), 112.12(d, J=24 Hz), 98.73(d, J=26Hz), 94.24(d, J=l l Hz), 40.21 (s, 3H).
		Production Example 341 3-Fluoro-5-iodophenylamine 3.2 g crude title compound (yellow oil) was obtained from 3.0 g of 3-fluoro-5-iodonitrobenzene by the same reaction as in Production Example 335.1H-NMR (CDCl3) delta: 3.78(brs, 2H), 6.28-6.35(m, 1H), 6.75-6.84(m, 2H)
	With iron; acetic acid; In tetrahydrofuran; water; at 40℃;	3-Iodo-5-fluoro-1-nitrobenzene (5.2 g; 19.48 mmol) is dissolved in a 4/3 water/tetrahydrofuran mixture. Powdered iron (8.7 g; 156 mmol), followed by acetic acid (4.5 ml) are added at room temperature and the suspension formed is stirred overnight at 40 C. The reaction mixture is filtered over diatomaceous earth and poured on to water. The mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexane/ethyl acetate (3/1). The pure fractions are combined and the solvent is evaporated off. The residue is diluted with methylene chloride (30 ml), and pyridine (4,0 ml; 49.5 mmol) and trifluoroacetic anhydride (3.44 ml; 24.7 mmol) are added and the mixture is stirred for one hour at room temperature. The reaction solution is poured on to aqueous hydrochloric acid (1 M; 50 ml) and the mixture is extracted twice with ethyl acetate (50 ml). The combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexanelethyl acetate (9/1). The pure fractions are combined and the solvent is evaporated off. [00367] Yield: 5.40 g (98%) as a white solid. [00368] MS: 333 (M)

Reference： [1]Patent: WO2013/71067,2013,A1 .Location in patent: Page/Page column 42-43
[2]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163
[3]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348
[4]Patent: EP1382603,2004,A1 .Location in patent: Page 170
[5]Patent: US6821980,2004,B1 .Location in patent: Page column 40-41
[6]Journal of Medicinal Chemistry,2013,vol. 56,p. 8404 - 8421

2
[ 660-49-1 ]
[ 821-48-7 ]
[ 852807-42-2 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163

3
[ 660-49-1 ]
(E)-3-[4-(3-fluoro-5-iodophenyl)piperazin-1-yl]-1-[5-methyl-1-(pyrimidin-2-yl)-1H-pyrazol-4-yl]prop-1-ene [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163

4
[ 660-49-1 ]
[ 1027953-88-3 ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163

5
[ 660-49-1 ]
3-[4-(3-fluoro-5-iodo-phenyl)-piperazin-1-yl]-1-(5-methyl-1-pyrimidin-2-yl-1<i>H</i>-pyrazol-4-yl)-propan-1-ol [ No CAS ]

Reference： [1]Chemical and Pharmaceutical Bulletin,2005,vol. 53,p. 153 - 163

6
[ 99-65-0 ]
[ 660-49-1 ]

Reference： [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348

7
[ 10394-64-6 ]
[ 660-49-1 ]

Reference： [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348

8
[ 6276-04-6 ]
[ 660-49-1 ]

Reference： [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348

9
5-Iod-3-nitro-1-diazonio-benzol [ No CAS ]
[ 660-49-1 ]

Reference： [1]Journal of Organic Chemistry,1960,vol. 25,p. 1342 - 1348

10
[ 660-49-1 ]
[ 124-63-0 ]
[ 710348-26-8 ]

Yield	Reaction Conditions	Operation in experiment
78%		Dissolve <strong>[660-49-1]3-fluoro-5-iodoaniline</strong> (600mg, 2. 53MMOL) (prepared as described in published PCT International Application W096/23783 A1, published August 8,1996), METHANESULFONYL chloride (896mg, 7. 83MMOL), triethylamine (1. 91G, 18.9mmol), and N, N-dimethylamino-4-pyridine (31MG, 0. 253MMOL) in CH2CK (lOmL) and stir at room temperature overnight. Dilute with L. OON aqueous HC1 (20ML) and extract into ethyl acetate. Dry (MGS04) and concentrate organics to a yellow solid. Dissolve solid in THF (50ML) and add L. OM tetrabutylammonium fluoride (2.8mL). Heat to reflux for 3. 5h. Cool to room temperature, dilute with H20, and extract into ethyl acetate. Dry (MGS04) and concentrate organics. Chromatograph on silica gel (40g), eluting with 20% to 35% ethyl acetate/hexanes affords 618MG (78%) of the title compound as a white solid. MS (ES) 314 (M-H) ; HPLC shows 100% purity.

Reference： [1]Patent: WO2004/52847,2004,A2 .Location in patent: Page 172

11
[ 660-49-1 ]
[ 407-25-0 ]
[ 338454-90-3 ]

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine; In dichloromethane; at 20℃; for 1h;	3-Iodo-5-fluoro-1-nitrobenzene (5.2 g; 19.48 mmol) is dissolved in a 4/3 water/tetrahydrofuran mixture. Powdered iron (8.7 g; 156 mmol), followed by acetic acid (4.5 ml) are added at room temperature and the suspension formed is stirred overnight at 40 C. The reaction mixture is filtered over diatomaceous earth and poured on to water. The mixture is extracted with ethyl acetate and the combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexane/ethyl acetate (3/1). The pure fractions are combined and the solvent is evaporated off. The residue is diluted with methylene chloride (30 ml), and pyridine (4,0 ml; 49.5 mmol) and trifluoroacetic anhydride (3.44 ml; 24.7 mmol) are added and the mixture is stirred for one hour at room temperature. The reaction solution is poured on to aqueous hydrochloric acid (1 M; 50 ml) and the mixture is extracted twice with ethyl acetate (50 ml). The combined organic phases are dried over sodium sulphate, filtered and concentrated. The residue is chromatographed over silica gel with n-hexanelethyl acetate (9/1). The pure fractions are combined and the solvent is evaporated off. [00367] Yield: 5.40 g (98%) as a white solid. [00368] MS: 333 (M)

Reference： [1]Patent: US6821980,2004,B1 .Location in patent: Page column 40-41

12
[ 660-49-1 ]
[ 474710-11-7 ]

Yield	Reaction Conditions	Operation in experiment
		Production Example 342 benzhydrylidene-(3-fluoro-5-iodophenyl)-amine 0.75 g of the title compound (yellow oil) was obtained from 3.2 g of <strong>[660-49-1]3-fluoro-5-iodophenylamine</strong> (compound in Production Example 341) by the same reaction as in Production Example 336.1H-NMR (CDCl3) delta: 6.36-6.43(m, 1H), 6.86-6.92(m, 1H), 6.96-7.02(m, 1H), 7.08-7.16(m, 2H), 7.28-7.54(m, 6H), 7.68-7.76(m, 2H)

Reference： [1]Patent: EP1382603,2004,A1 .Location in patent: Page 170; 171

13
[ 660-49-1 ]
[ 74-88-4 ]
[ 1369808-80-9 ]

Yield	Reaction Conditions	Operation in experiment
52%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 48h;	Example 2Synthesis of 3-fluoro-5-iodo-N,N-dimethylaniline (VMY-2-119): The suspension of l-fluoro-3-iodo-5 -nitrobenzene (0.5 g, 1.87 mmol) and SnCl2'2H20 (1.5 g, 6.64 mmol) in EtOH (10 mL) was heated to reflux for 1.5 h. The solvent was removed and the crude mixture was diluted with ether, washed with 4 N NaOH and brine. The ether layer was- 42 -B4067289v2 separated and dried over Na2S04, filtered, concentrated to yield amine compound as a solid (0.4 g, 91%). The crude product was used without purification.A solution of above amine (0.4 g, 1.69 mmol) and iodomethane (0.719 g, 5 mmol) in dimethylformamide (DMF; 10 mL) containing potassium carbonate (0.46 g, 3.38 mmol) was stirred for 48 h at room temperature. Water (lOmL) was then added and the solution was extracted with ether three times. The organic extracts washed with water, brine, dried over Na2S04, filtered and concentrated. The crude product was purified by column chromatography to yield VMY-2-119 as a liquid (0.23 g, 52%). 1H NMR (399 MHz) ? 6.69 - 6.63 (m, 2H), 6.22 (dt, J = 12.5, 2.3, 1H), 2.83 (s, 6H). 13C NMR (100 MHz) ? 163.33(d, JF-C=245 Hz), 152.49(d, J=l lHz) 116.91 (d, J = 2.4), 112.12(d, J=24 Hz), 98.73(d, J=26Hz), 94.24(d, J=l l Hz), 40.21 (s, 3H).

Reference： [1]Patent: WO2013/71067,2013,A1 .Location in patent: Page/Page column 42-43
[2]Journal of Medicinal Chemistry,2013,vol. 56,p. 8404 - 8421

14
[ 660-49-1 ]
C₁₇H₂₁FINO₄ [ No CAS ]