[ CAS No. 13329-40-3 ] {[proInfo.proName]}

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2D 3D

Structure of 13329-40-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 13329-40-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13329-40-3 ]

SDS Specification

Alternatived Products of [ 13329-40-3 ]

Product Details of [ 13329-40-3 ]

CAS No. :	13329-40-3	MDL No. :	MFCD00045320
Formula :	C₈H₇IO	Boiling Point :	-
Linear Structure Formula :	CH₃CO(C₆H₄)I	InChI Key :	JZJWCDQGIPQBAO-UHFFFAOYSA-N
M.W :	246.05	Pubchem ID :	72869
Synonyms :

Calculated chemistry of [ 13329-40-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	10
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.35
TPSA :	17.07 ?2

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) :	-6.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.0
Log Po/w (XLOGP3) :	2.39
Log Po/w (WLOGP) :	2.49
Log Po/w (MLOGP) :	2.67
Log Po/w (SILICOS-IT) :	3.12
Consensus Log Po/w :	2.53

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.25
Solubility :	0.139 mg/ml ; 0.000563 mol/l
Class :	Soluble
Log S (Ali) :	-2.39
Solubility :	1.0 mg/ml ; 0.00408 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.69
Solubility :	0.0504 mg/ml ; 0.000205 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.6

Safety of [ 13329-40-3 ]

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 [ 13329-40-3 ]

* 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 [ 13329-40-3 ]
Downstream synthetic route of [ 13329-40-3 ]

[ 13329-40-3 ] Synthesis Path-Upstream 1~2

1
[ 13329-40-3 ]
[ 62-53-3 ]
[ 23600-83-1 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium hydroxide In dimethyl sulfoxide at 120℃; Inert atmosphere	General procedure: A mixture of amine (2.0 mmol), aryl halides (1.0 mmol), catalyst (1.0 molpercent Pd), and DMSO (6 ml) was stirred for 16 h under nitrogen atmosphere at 120 ?C. The progress of reaction was monitored by gas chromatography. After completion, the reaction mixture was cooled and filtered to remove the catalyst which could be used for further reaction. The filtrate obtained was purified by flash column chromatography on silica gel to afford the desired product, which was confirmed by GC–MS. All the prepared compounds are known and compared with authentic samples.
83 %Chromat.	With C₃₅H₃₄N₃OP₂PdS⁽¹⁺⁾*NO₃^(1-); sodium t-butanolate In 1,4-dioxane at 100℃; for 7 h;	General procedure: In a typical run, an oven-dried 10 ml round bottom flask was charged with a known mole percent of catalyst, NaOtBu (1.3 mmol), amine (1.2 mmol) and aryl halide (1 mmol) with the appropriate solvent(s) (4 ml). The flask was placed in a preheated oil bath at required temp. After the specified time the flask was removed from the oil bath, water (20 ml) was added, and extraction with ether (4×10 ml) was done. The combined organic layers were washed with water (3×10 ml), dried over anhydrous Na2SO4, and filtered. Solvent was removed under vacuum. The residue was dissolved in acetonitrile and analyzed by GC–MS.

Reference： [1] Organometallics, 2012, vol. 31, # 21, p. 7336 - 7338
[2] Journal of Organic Chemistry, 2017, vol. 82, # 10, p. 5416 - 5423
[3] Journal of Molecular Catalysis A: Chemical, 2013, vol. 366, p. 321 - 332
[4] Angewandte Chemie - International Edition, 2016, vol. 55, # 42, p. 13219 - 13223[5] Angew. Chem., 2016, vol. 128, # 42, p. 13413 - 13417,5
[6] Journal of Organometallic Chemistry, 2010, vol. 695, # 21, p. 2284 - 2295
[7] Inorganica Chimica Acta, 2019, vol. 486, p. 232 - 239

2
[ 591-50-4 ]
[ 13329-40-3 ]
[ 23600-83-1 ]

Reference： [1] Chemical Communications, 2012, vol. 48, # 51, p. 6408 - 6410

[ 13329-40-3 ] Synthesis Path-Downstream 1~11

1
[ 64-17-5 ]
[ 13329-40-3 ]
[ 201230-82-2 ]
[ 38430-55-6 ]

Yield	Reaction Conditions	Operation in experiment
92%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; at 80℃; under 760.051 Torr; for 6h;	General procedure: The catalytic reactions were carried out in a 10 mL reaction flask and fitted with condenser and carbon monoxide balloon. In a typical run, a catalyst containing 1.0 mol% Pd, aryl iodide (0.5 mmol) and DBU (1.5 mmol) were added to solvent and allowed to react under CO atmosphere at 80 C temperature for 6-10 h. After the reaction,the flask was cooled to room temperature and carbon monoxide balloon was removed. The reaction mixture was then centrifuged and the clear supernatant was analyzed with GC by using n-butanol as an internal standard. For the study of substrate scope, after completion of the reaction, the catalyst was centrifuged and extracted with copious ethanol. The obtained liquid was concentrated. For phenoxycarbonylation, the obtained liquid was diluted with saturated NH4Cl and extracted with diethyl ether. The organic layer was dried over anhydrous Na2SO4 and then concentrated. The product was obtained by preparative thin-layer chromatography (PTLC) using petroleum ether and ethyl acetate (30:1, v/v) as eluting solvent. The purity of products was checked by NMR and yields were based on aryl iodides.

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 65 - 68
[2]Synlett,2007,p. 2006 - 2010
[3]RSC Advances,2015,vol. 5,p. 94776 - 94785
[4]Tetrahedron Letters,1991,vol. 32,p. 4733 - 4736
[5]Applied Organometallic Chemistry,2019,vol. 33
[6]Journal of Molecular Catalysis A: Chemical,2015,vol. 398,p. 164 - 169
[7]Tetrahedron,2008,vol. 64,p. 9581 - 9584
[8]ACS Catalysis,2013,vol. 3,p. 287 - 293
[9]Journal of Organic Chemistry,1991,vol. 56,p. 4320 - 4322
[10]Organic Process Research and Development,2009,vol. 13,p. 634 - 637
[11]Organic process research and development,2011,vol. 15,p. 717 - 720
[12]Chemical Communications,2018,vol. 54,p. 8100 - 8103

2
[ 13329-40-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 6388 - 6396

3
[ 52522-40-4 ]
[ 13329-40-3 ]
[ 119072-54-7 ]
[ 926042-24-2 ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 620 - 624

4
[ 13329-40-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.7%	With potassium hydroxide; In ethanol; water; at 20℃; for 3.0h;	Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one (33) 4-Iodoacetophenone (246 mg, 1.00 mmol) and Compound 30 (155 mg, 1.00 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (7.5 mL). The mixture was reacted at room temperature for 3 h, the layers were separated with ethyl acetate (50 mL x 2), and the ethyl acetate layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain Compound 33. Yield 18 mg (yield rate 4.7%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J = 3.9 Hz, 1H), 6.80 (d, J = 3.6 Hz, 1H), 6.89 (d, J = 15.0 Hz, 1H), 7.46 (d, J = 14.7 Hz, 1H), 7.70 (d, J = 8.1 Hz, 2H), 7.81 (d, J = 8.7 Hz, 2H). MS m/z 383 (M+).

Reference： [1]Patent: EP2030635,2009,A1 .Location in patent: Page/Page column 26-27; 50

5
aqueous potassium hydroxide [ No CAS ]
[ 13329-40-3 ]
[ 24372-46-1 ]
3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
4.7%	In ethanol; hexane; ethyl acetate;	Synthesis of 3-(5-dimethylamino-2-thienyl)-1-(4-iodophenyl)-prop-2-en-1-one (33) 4-Iodoacetophenone (246 mg, 1.00 mmol) and Compound 30 (155 mg, 1.00 mmol) were dissolved in ethanol (5 mL), followed by addition of 10% aqueous potassium hydroxide (7.5 mL). The mixture was reacted at room temperature for 3 h, the layers were separated with ethyl acetate (50 mL*2), and the ethyl acetate layer was dried with anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to medium-pressure preparative chromatography using ethyl acetate/hexane (1/4) as an elution solvent to obtain Compound 33. Yield 18 mg (yield rate 4.7%). 1H NMR (300 MHz, CDCl3) delta 3.04 (s, 6H), 5.22 (d, J=3.9 Hz, 1H), 6.80 (d, J=3.6 Hz, 1H), 6.89 (d, J=15.0 Hz, 1H), 7.46 (d, J=14.7 Hz, 1H), 7.70 (d, J=8.1 Hz, 2H), 7.81 (d, J=8.7 Hz, 2H). MS m/z 383 (M+).

Reference： [1]Patent: US2010/278733,2010,A1

6
[ 10226-29-6 ]
[ 13329-40-3 ]
1-(p-acetylphenyl)-5-oxohexane [ No CAS ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 4778 - 4780

7
[ 13329-40-3 ]
[ 78364-55-3 ]
6-fluoro-2-[2-(1-(4-iodophenyl)ethylidene)hydrazino]benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With acetic acid; In ethanol;Reflux;	General procedure: 6-Fluoro-2-[2-(1-(substituted phenyl)ethylidene)hydraizno]benzothiazoles 7a-d. General Procedure E. A mixture of compound 2 (0.183 g, 0.001 mol), the appropriate acetophenone (0.001 mol) and glacial acetic acid (0.1 mL) in ethanol (20 mL) was heated at reflux temperature for 6-8 h. On cooling, the precipitated solid was collected by filtration, washed with ethanol, dried and crystallized from ethyl acetate : ethanol (3:1) to furnish compounds 7a-d.

Reference： [1]Chinese Chemical Letters,2015,vol. 26,p. 1522 - 1528

8
[ 13329-40-3 ]
[ 2914-69-4 ]
(-)-(S)-1-(4-(3-hydroxybut-1-yn-1-yl)phenyl)ethan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2017,vol. 139,p. 8448 - 8451

9
[ 773881-43-9 ]
[ 13329-40-3 ]
1,3-bis(4-acetylphenyl)-5-octyl-4H-thieno[3,4-c]pyrrole-4,6(5H)-dione [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4754 - 4757
[2]Journal of Organic Chemistry,2018,vol. 83,p. 9312 - 9321

10
[ 13329-40-3 ]
[ 98-55-5 ]
1-(4-(4-(2-hydroxypropan-2-yl)-1-methylcyclohexyl)phenyl)ethan-1-one [ No CAS ]
1-(4-(4-(2-hydroxypropan-2-yl)-1-methylcyclohexyl)phenyl)ethan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 11317 - 11324

11
[ 381-98-6 ]
[ 13329-40-3 ]
(Z)-3-(4-acetylphenyl)-2-(trifluoromethyl)acrylic acid [ No CAS ]
(E)-3-(4-acetylphenyl)-2-(trifluoromethyl)acrylic acid [ No CAS ]

Reference： [1]Advanced synthesis and catalysis,2020,vol. 362,p. 949 - 954

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Isomers

Technical Information

? Alkyl Halide Occurrence ? Baeyer-Villiger Oxidation ? Barbier Coupling Reaction ? Baylis-Hillman Reaction ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bucherer-Bergs Reaction ? Clemmensen Reduction ? Corey-Bakshi-Shibata (CBS) Reduction ? Corey-Chaykovsky Reaction ? Fischer Indole Synthesis ? Friedel-Crafts Reaction ? General Reactivity ? Grignard Reaction ? Henry Nitroaldol Reaction ? Hiyama Cross-Coupling Reaction ? Horner-Wadsworth-Emmons Reaction ? Hydride Reductions ? Hydrogenolysis of Benzyl Ether ? Kinetics of Alkyl Halides ? Lawesson's Reagent ? Leuckart-Wallach Reaction ? McMurry Coupling ? Meerwein-Ponndorf-Verley Reduction ? Passerini Reaction ? Paternò-Büchi Reaction ? Petasis Reaction ? Peterson Olefination ? Pictet-Spengler Tetrahydroisoquinoline Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Preparation of Amines ? Prins Reaction ? Reactions of Aldehydes and Ketones ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Benzene and Substituted Benzenes ? Reactions of Dihalides ? Reformatsky Reaction ? Robinson Annulation ? Schlosser Modification of the Wittig Reaction ? Schmidt Reaction ? Specialized Acylation Reagents-Ketenes ? Stobbe Condensation ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling ? Tebbe Olefination ? Ugi Reaction ? Vilsmeier-Haack Reaction ? Wittig Reaction ? Wolff-Kishner Reduction

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[ 13329-40-3 ]

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H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 13329-40-3 ] {[proInfo.proName]}

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[ 13329-40-3 ] Synthesis Path-Upstream 1~2

[ 13329-40-3 ] Synthesis Path-Downstream 1~11

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Aryls

Ketones

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[ 13329-40-3 ]