[ CAS No. 699016-40-5 ] {[proInfo.proName]}

Name: 699016-40-5|2-Fluoro-4-iodobenzaldehyde|97%
Brand: Ambeed
SKU: A441896
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2D 3D

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Quality Control of [ 699016-40-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 699016-40-5 ]

SDS Specification

Alternatived Products of [ 699016-40-5 ]

Product Details of [ 699016-40-5 ]

CAS No. :	699016-40-5	MDL No. :	MFCD07782056
Formula :	C₇H₄FIO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LMDKAOXRCQPCAW-UHFFFAOYSA-N
M.W :	250.01	Pubchem ID :	4090083
Synonyms :

Calculated chemistry of [ 699016-40-5 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	44.5
TPSA :	17.07 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) :	-6.31 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.83
Log Po/w (XLOGP3) :	2.13
Log Po/w (WLOGP) :	2.66
Log Po/w (MLOGP) :	2.79
Log Po/w (SILICOS-IT) :	3.37
Consensus Log Po/w :	2.56

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.11
Solubility :	0.194 mg/ml ; 0.000776 mol/l
Class :	Soluble
Log S (Ali) :	-2.12
Solubility :	1.9 mg/ml ; 0.00759 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.58
Solubility :	0.0658 mg/ml ; 0.000263 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	1.81

Safety of [ 699016-40-5 ]

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 [ 699016-40-5 ]

* 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 [ 699016-40-5 ]
Downstream synthetic route of [ 699016-40-5 ]

[ 699016-40-5 ] Synthesis Path-Upstream 1~2

1
[ 68-12-2 ]
[ 147808-02-4 ]
[ 699016-40-5 ]

Yield	Reaction Conditions	Operation in experiment
67%	Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at -78 - -50℃; for 0.5 h; Stage #2: at 0 - 20℃; for 0.25 h; Stage #3: With water; ammonium chloride In tetrahydrofuran	Step 1-A: A solution of 2-fluoro-1,4-diiodo-benzene (804 mg, 2.31 mmol) in tetrahydrofuran (8 mL) was cooled to -78° C. (external) and a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (1.44 mL, 2.89 mmol) added via syringe. The resulting mixture was stirred for 30 minutes while allowing the temperature of the cooling bath to rise to -50° C. The reaction mixture was then immersed in an ice/water bath and anhydrous N,N-dimethylformamide (425 μL, 5.78 mmol) was added by syringe to the reaction mixture. The reaction was stirred at 0° C. for 10 minutes, then at room temperature for 5 minutes. Thin layer chromatography (TLC) indicated the reaction to be complete. The mixture was diluted with saturated aqueous ammonium chloride solution (8 mL) and extracted with diethylether (2*20 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by chromatography over silica gel gradient eluted with 0 to 15percent v/v ethyl acetate/hexanes to give 2-fluoro-4-iodo-benzaldehyde as a fluffy-white solid (389 mg, 67percent).

Reference： [1] Patent: US2009/170920, 2009, A1, . Location in patent: Page/Page column 10-11

2
[ 248270-23-7 ]
[ 699016-40-5 ]

Reference： [1] Patent: US2004/106653, 2004, A1, . Location in patent: Page/Page column 43-44

[ 699016-40-5 ] Synthesis Path-Downstream 1~17

1
[ 699016-40-5 ]
[ 699016-02-9 ]
[ 699016-41-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In DMF (N,N-dimethyl-formamide); at 60℃; for 2h;	Under nitrogen at room temperature, to a solution of 2,2,2-trifluoro-N-[(1R)-2-(4-mercaptophenyl)-1-methylethyl]acetamide (4.0 g) in N,N-dimethylformamide (40 ml) was added <strong>[699016-40-5]2-fluoro-4-iodobenzaldehyde</strong> (4.18 g) and potassium carbonate (2.31 g), and the mixture was stirred at 60 C. for 2 hours.The resulting mixture was poured into water and the aqueous mixture was extracted with ethyl acetate.The organic layer was washed successively with water (two times) and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography on silica gel (chloroform/ethyl acetate=10:1) to give 2,2,2-trifluoro-N-[(1R)-2-[4-[(2-formyl-5-iodophenyl)thio]phenyl]-1-methylethyl]acetamide (5.02 g). (+)ESI-MS (m/z): 516 (M+Na)+

Reference： [1]Patent: US2004/106653,2004,A1 .Location in patent: Page/Page column 44

2
[ 248270-23-7 ]
[ 699016-40-5 ]

Yield	Reaction Conditions	Operation in experiment
		Under nitrogen in dry ice-acetone bath, to a solution of 2-(4-bromo-2-fluorophenyl)-1,3-dioxolane (5.5 g) in tetrahydrofuran (80 ml) was added butyl lithium (1.58M in hexane, 14.8 ml), and the mixture was stirred at the same temperature for 40 minutes.To this one was added a solution of iodine (17 g) in tetrahydrofuran (30 ml) in dry ice-acetone bath, and the mixture was stirred at the same temperature for 40 minutes and then at 5 C. for 1.5 hours.To the resulting mixture was added aqueous sodium thiosulfate and ethyl acetate at 5 C., and the mixture was stirred at the same temperature for 5 minutes.After separation, the organic layer was washed successively with saturated aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure.The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10:1) to give iodo compounds.To the solution of the iodo compounds in a mixture of tetrahydrofuran (20 ml) and methanol (20 ml) was added 6N hydrochloric acid (10 ml) at room temperature, and the mixture was stirred at the same temperature for 12 hours.The volatile solvents were removed by evaporation to give precipitates.To this one was added water, and the mixture was stirred for 1 hour.The precipitates were collected by filtration and dried in vacuo to give 2-fluoro-4-iodobenzaldehyde (1.79 g). NMR (CDCl3, delta): 7.5-7.75 (3H, m), 10.31 (1H, s)

Reference： [1]Patent: US2004/106653,2004,A1 .Location in patent: Page/Page column 43-44

3
[ 19012-03-4 ]
[ 708-76-9 ]
[ 4397-53-9 ]
[ 487-68-3 ]
[ 699016-40-5 ]
[ 2233-18-3 ]
[ 5736-94-7 ]
[ 26260-02-6 ]
[ 3934-87-0 ]
[ 492-88-6 ]
[ 6280-80-4 ]
[ 4659-47-6 ]
[ 89-98-5 ]
[ 71653-64-0 ]
[ 123-08-0 ]
[ 120-14-9 ]
[ 446-52-6 ]
[ 66-99-9 ]
[ 10040-98-9 ]
[ 85070-48-0 ]
[ 93777-26-5 ]
[ 134-96-3 ]
[ 79124-75-7 ]
2-chloro-6-fluoro-3-methylbenzaldehyde [ No CAS ]
[ 544431-10-9 ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-fluoro-phenyl)-acrylamide [ No CAS ]
3-(2-chloro-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hydroxy-phenyl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-iodo-phenyl)-acrylamide [ No CAS ]
3-(3-chloro-2-fluoro-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-naphthalen-2-yl-acrylamide [ No CAS ]
3-(5-bromo-2-fluoro-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-3-(3,4-dimethoxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(1-methyl-1H-indol-3-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-imidazol-1-yl-phenyl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-fluoro-4-iodo-phenyl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2,4,6-trimethyl-phenyl)-acrylamide [ No CAS ]
2-cyano-3-(2-difluoromethoxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hydroxy-3,5-dimethyl-phenyl)-acrylamide [ No CAS ]
3-(2-chloro-6-fluoro-3-methyl-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2,3,6-trichloro-phenyl)-acrylamide [ No CAS ]
2-cyano-3-(3-ethoxy-2-hydroxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
{2-[2-cyano-2-(5-ethyl-[1,3,4]thiadiazol-2-ylcarbamoyl)-vinyl]-phenoxy}-acetic acid [ No CAS ]
2-cyano-3-(3,4-dihydroxy-5-methoxy-phenyl)-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hydroxy-3,5-dimethoxy-phenyl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(2-hydroxy-4,6-dimethoxy-phenyl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(3-p-tolyloxy-phenyl)-acrylamide [ No CAS ]
3-(4-benzyloxy-phenyl)-2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-acrylamide [ No CAS ]
2-cyano-N-(5-ethyl-[1,3,4]thiadiazol-2-yl)-3-(4-hexyloxy-phenyl)-acrylamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A 0.25 M stock solution of 2-cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2- yl)-acetamide was prepared in 1.0 M diisopropylethylamine in DMF. Benzaldehyde and other heterocyclic aldehydes were individually weighed and were dissolved to 0.25 M using a Tecan Genesis workstation. The Tecan was used to dispense 200 muL of template 1 to each reaction vessel then was used to dispense 400 L of aldehyde stock solutions to individual reaction vessels. The reaction vessels were sealed and were heated at 45-50 C, with agitation, for 18 hours. The reaction vessels were then cooled, unsealed, and 50 L of aminopropyl-functionalized silica gel (Aldrich) was dispensed to each reaction vessel. Activated 4 angstrom molecular sieves (powdered, 50 L) were then dispensed to each reaction. Reaction vessels were then sealed and were heated at 45-50 C with agitation for 3 h. Reactions were then unsealed and were filtered to remove solids. B. Sample solutions were dried in vacuo using a Genevac. Samples were dissolved in 500 pL of DMSO and 500 pL of methanol and purity was determined by LC-MS with using a combination of UV254, UV220, and ELSD detection [purity = (UV254+UV220/2)]. The HPLC conditions were: 4.6 mm x 50 mm C18 column, 10-90% acetonitrile gradient over 5 minutes (mobile phases were H20 with 0.05 % TFA and acetonitrile with 0.035 % TFA), with a flow rate of 3.5 ml/min. Samples which were <80% pure were purified using a mass directed LC-MS purification. Purified samples were concentrated in vacuo then were dissolved in DMSO and were reformatted into 96 well microtiter plates. Samples were tested for purity using LC-MS and quantity was estimated by correlating ELSD response to a standard concentration-ELSD response curve. Samples were then concentrated to dryness and were dissolved in DMSO to a final concentration of 10 uM based on ELSD quantitation. C. The following compounds were prepared in the manner described above in Steps A and B using the appropriate aldehyde in place of benzaldehyde: 2-Cyano-3- (3, 4-dimethoxy-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 345 (MH+) ; 3- (4-Benzyloxy-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES) : 391 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (4-hydroxy-phenyl)- acrylamide ; MS (ES): 301 (MH+) ; Acetic acid 4- [2-cyano-2- (5-ethyl- [1, 3,4] thiadiazol-2-ylcarbamoyl)-vinyl]- phenyl ester; MS (ES): 343 (MH+); 2-Cyano-3- (2, 4-dichloro-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 353 (MH+) ; 3- (2-Bromo-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 363 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (2-fluoro-phenyl)- acrylamide ; MS (ES): 303 (MH+) ; 3- (4-tert-Butyl-phenyl)-2-cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)- acrylamide ; MS (ES): 341 (MH+) ; 3- (2-Chloro-4-fluoro-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 337 (MH+) ; 2-Cyano-3- (2, 5-dimethyl-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 313 (MH+) ; 2-Cyano-5- (4-methoxy-phenyl)-penta-2, 4-dienoic acid (5-ethyl- [1,3, 4] thiadiazol-2-yl)-amide ; MS (ES): 341 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3-(4-hydroxy-3, 5-dimethoxy- phenyl)-acrylamide ; MS (ES): 361 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (4-hydroxy-3-iodo-5- methoxy-phenyl)-acrylamide ; MS (ES): 457 (MH+) ; 2-Cyano-3- (3, 4-dihydroxy-phenyl)-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)- acrylamide ; MS (ES): 317 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3- (4-hydroxy-3-methoxy-5- nitro-phenyl)-acrylamide ; MS (ES): 376 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yi)-3- (4-hydroxy-3-methoxy-5- nitro-phenyl)-acrylamide ; MS (ES): 376 (MH+) ; 3-(4-Benzyloxy-3,5-dimethyl-phenyl)-2-cyano-N-(5-ethyl- [1,3, 4] thiadiazol-2-yl)-acrylamide ; MS (ES): 419 (MH+) ; 2-Cyano-3- (3, 5-dibromo-2-methoxy-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol- 2-yl)-acrylamide ; MS (ES) : 471 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)-3- (4-hexyloxy-phenyl)- acrylamide ; MS (ES): 385 (MH+) ; Acetic acid 4- [2-cyano-2- (5-ethyl- [1, 3,4] thiadiazol-2-ylcarbamoyl)-vinyl]- 2, 6-dimethoxy-phenyl ester; MS (ES): 403 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yi)-3- (4-imidazol-1-yi-phenyl)- acrylamide ; MS (ES): 351 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)-3-(2-trifluoromethyl-phenyl)- acrylamide ; MS (ES): 353 (MH+) ; 3- (2-Chloro-3, 4-dimethoxy-phenyl)-2-cyano-N- (5-ethyl- [1, 3,4] thiadiazol- 2-yl)-acrylamide ; MS (ES): 379 (MH+) ; 2-Cyano-N- (5-ethyl- [1, 3, 4] thiadiazol-2-yl)-3- ( 1-methyl-1 H-indol-3-yl)- acrylamide ; MS (ES): 338 (MH+) ; 2-Cyano-3- (2, 6-dichloro-phenyl)-N- (5-ethyl- [1, 3,4] thiadiazol-2-yl)- acrylamide ; MS (ES): 353 (MH+) ; 2-Cyano-3-(4-dimethylamino-2-nitro-phenyl)-N-(5-ethyl-[1, 3,4] thiadiazol- 2-yl)-acrylamide ; MS (ES): 373 (MH+) ; 2-Cyano-N-(5-ethyl-[1, 3,4] thiadiazol-2-yl)-3- (2-iodo-phe...

Reference： [1]Patent: WO2005/72731,2005,A1 .Location in patent: Page/Page column 95-103

4
[ 68-12-2 ]
[ 147808-02-4 ]
[ 699016-40-5 ]

Yield	Reaction Conditions	Operation in experiment
67%		Step 1-A: A solution of <strong>[147808-02-4]2-fluoro-1,4-diiodo-benzene</strong> (804 mg, 2.31 mmol) in tetrahydrofuran (8 mL) was cooled to -78 C. (external) and a 2.0 M solution of isopropylmagnesium chloride in tetrahydrofuran (1.44 mL, 2.89 mmol) added via syringe. The resulting mixture was stirred for 30 minutes while allowing the temperature of the cooling bath to rise to -50 C. The reaction mixture was then immersed in an ice/water bath and anhydrous N,N-dimethylformamide (425 muL, 5.78 mmol) was added by syringe to the reaction mixture. The reaction was stirred at 0 C. for 10 minutes, then at room temperature for 5 minutes. Thin layer chromatography (TLC) indicated the reaction to be complete. The mixture was diluted with saturated aqueous ammonium chloride solution (8 mL) and extracted with diethylether (2*20 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by chromatography over silica gel gradient eluted with 0 to 15% v/v ethyl acetate/hexanes to give 2-fluoro-4-iodo-benzaldehyde as a fluffy-white solid (389 mg, 67%).

Reference： [1]Patent: US2009/170920,2009,A1 .Location in patent: Page/Page column 10-11

5
[ 699016-40-5 ]
[ 676-58-4 ]
[ 1165872-80-9 ]

Yield	Reaction Conditions	Operation in experiment
84%		Step 1-B: To a solution of <strong>[699016-40-5]2-fluoro-4-iodo-benzaldehyde</strong> (17.40 g, 69.60 mmol) in anhydrous tetrahydrofuran (300 mL) at -10 C. under an atmosphere of nitrogen was added 3.0 M methylmagnesium chloride in tetrahydrofuran (27.84 mL, 83.52 mmol) via syringe at such a rate as to maintain the temperature of the reaction mixture below 0 C. The reaction was stirred for 30 minutes while warming to room temperature. Saturated aqueous ammonium chloride solution was added and the mixture was diluted with ethyl acetate (200 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (250 mL). The organic extracts were combined, washed with water (150 mL), brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography over silica gel gradient eluted with 15 to 40% v/v ethyl acetate/hexanes to give 1-(2-fluoro-4-iodo-phenyl)-ethanol (15.50 g, 84%).

Reference： [1]Patent: US2009/170920,2009,A1 .Location in patent: Page/Page column 11

6
[ 699016-40-5 ]
C₁₇H₁₃FIN₃ [ No CAS ]