[ CAS No. 849517-65-3 ] {[proInfo.proName]}

Name: 849517-65-3|4-Iodobenzo[d][1,3]dioxole|95%
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SKU: A120074
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Quality Control of [ 849517-65-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 849517-65-3 ]

SDS Specification

Alternatived Products of [ 849517-65-3 ]

Product Details of [ 849517-65-3 ]

CAS No. :	849517-65-3	MDL No. :	MFCD13152331
Formula :	C₇H₅IO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NEMFWXWQUHOSSH-UHFFFAOYSA-N
M.W :	248.02	Pubchem ID :	18788521
Synonyms :

Calculated chemistry of [ 849517-65-3 ]

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.14
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	45.22
TPSA :	18.46 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) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.19
Log Po/w (XLOGP3) :	2.39
Log Po/w (WLOGP) :	2.02
Log Po/w (MLOGP) :	2.08
Log Po/w (SILICOS-IT) :	2.93
Consensus Log Po/w :	2.32

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.33
Solubility :	0.117 mg/ml ; 0.000471 mol/l
Class :	Soluble
Log S (Ali) :	-2.42
Solubility :	0.945 mg/ml ; 0.00381 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.11
Solubility :	0.194 mg/ml ; 0.000783 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.48

Safety of [ 849517-65-3 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 849517-65-3 ]

* 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 [ 849517-65-3 ]
Downstream synthetic route of [ 849517-65-3 ]

[ 849517-65-3 ] Synthesis Path-Upstream 1~4

1
[ 75-11-6 ]
[ 25245-33-4 ]
[ 849517-65-3 ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; Inert atmosphere Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 1 h; Inert atmosphere	To a solution of 34a (792 mg, 3.00 mmol) in CH₂Cl₂ (10.0 mL) was added BBr₃ (1.0 M CH₂Cl₂ solution, 14.0 mL, 14.0 mmol) at -78 °C under Ar atmosphere, and the mixture was stirred at the room temperature. After 42 h, the reaction mixture was poured into ice, and volatile materials were removed under reduced pressure. The residue was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was dissolved in DMF (30 mL), and to this were added Cs₂CO₃ (1.00 g, 3.07 mmol) and CH₂I₂ (250 mL, 3.10 mmol) and the mixture was stirred at 120 °C for 1 h under Ar atmosphere. After the reaction mixture was cooled to room temperature, DMF was removed under reduced pressure. To the residue were added ethyl acetate and water, and the resulting insoluble material was removed by filtration and washed with ethyl acetate. The filtrate was extracted with ethyl acetate, and the combined organic layer was washed with brine, dried over Na₂SO₄, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate = 50:1) to give 34b [563 mg, 2.27 mmol, 76percent (2 steps)] as a white solid. Mp 35.5-37.0 °C; ¹H NMR (CDCl₃, 500 MHz) δ 7.11 (dd, J = 1.2, 8.6 Hz, 1H), 6.75 (dd, J = 1.2, 7.9 Hz, 1H), 6.78 (dd, J = 7.9, 8.6 Hz, 1H), 5.99 (s, 2H); MS (FAB) m/z 248 (M)⁺.
76%	Stage #1: With boron tribromide In dichloromethane at -78 - 20℃; for 18 h; Stage #2: With caesium carbonate In N,N-dimethyl-formamide at 120℃; for 1 h;	Anhydrous dichloromethane (10 ml) and boron tribromide (1.0 M dichloromethane solution, 14.0 ml, 14.0 mmol) were added to 3-iodo-1,2-dimethoxybenzene (i) (792 mg, 3.00 mmol) at -78° C., and the mixture was agitated at room temperature for 18 hours. The reaction solution was poured into iced water, dichloromethane was evaporated under a reduced pressure, and an organic phase was extracted with ethyl acetate. The organic phase was washed with an aqueous solution of saturated sodium chloride, and the resultant was dried over sodium sulfate, followed by concentration under a reduced pressure. Anhydrous N,N-dimethylformamide (30 ml), cesium carbonate (1.00 g, 3.07 mmol), and diiodomethane (0.250 ml, 3.10 mmol) were added to the residue, and the mixture was agitated at 120° C. for 1 hour. N,N-dimethylformamide was evaporated under a reduced pressure, water was added thereto, and an organic phase was extracted with ethyl acetate. The organic phase was washed with water and an aqueous solution of saturated sodium chloride, and the resultant was dried over sodium sulfate, followed by concentration under a reduced pressure. A crude product was purified via silica gel column chromatography using hexane:ethyl acetate (50:1) as an eluting solvent (yield: 563 mg, 76percent).

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2675 - 2687
[2] Patent: US2012/316342, 2012, A1, . Location in patent: Page/Page column 24

2
[ 91-16-7 ]
[ 849517-65-3 ]

Reference： [1] Bioorganic and Medicinal Chemistry, 2011, vol. 19, # 8, p. 2675 - 2687
[2] Patent: US2012/316342, 2012, A1,

3
[ 111726-43-3 ]
[ 849517-65-3 ]

Reference： [1] Helvetica Chimica Acta, 2012, vol. 95, # 11, p. 2194 - 2217

4
[ 533-31-3 ]
[ 849517-65-3 ]

Reference： [1] Helvetica Chimica Acta, 2012, vol. 95, # 11, p. 2194 - 2217

[ 849517-65-3 ] Synthesis Path-Downstream 1~31

1
[ 849517-65-3 ]
[ 1307741-37-2 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 2675 - 2687
[2]Patent: US2012/316342,2012,A1

2
[ 849517-65-3 ]
[ 1307741-70-3 ]