83279-38-3|3-Chloro-4-(trifluoromethyl)benzaldehyde| Ambeed

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Quality Control of [ 83279-38-3 ] Purity: 95% SDS Specification

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Product Details of [ 83279-38-3 ]

CAS No. :	83279-38-3
Formula :	C₈H₄ClF₃O
M.W :	208.57
SMILES Code :	O=CC1=CC=C(C(F)(F)F)C(Cl)=C1
MDL No. :	MFCD03095197
InChI Key :	UTSBZTCYCRVHCK-UHFFFAOYSA-N
Pubchem ID :	19031287

Safety of [ 83279-38-3 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 83279-38-3 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	6
Fraction Csp3	0.12
Num. rotatable bonds	2
Num. H-bond acceptors	4.0
Num. H-bond donors	0.0
Molar Refractivity	41.84
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.07 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.71
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.9
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.32
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.08
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.65
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.13

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.17
Solubility	0.141 mg/ml ; 0.000677 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.92
Solubility	0.251 mg/ml ; 0.00121 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.85
Solubility	0.0291 mg/ml ; 0.00014 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.51 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.41

Application In Synthesis of [ 83279-38-3 ]

* 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.

Downstream synthetic route of [ 83279-38-3 ]

[ 83279-38-3 ] Synthesis Path-Downstream 1~20

1
[ 110-89-4 ]
[ 83279-38-3 ]
[ 105-45-3 ]
methyl 2-acetyl-3-(3-chloro-4-trifluoromethylphenyl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In dichloromethane; acetic acid;	EXAMPLE 1 Methyl 2-acetyl-3-(3-chloro-4-trifluoromethylphenyl)acrylate STR48 32.3 g (155 mol) of <strong>[83279-38-3]3-chloro-4-trifluoromethylbenzaldehyde</strong> and 18.0 g (155 mmol) of methyl acetoacetate are dissolved in 200 ml of methylene chloride, and 1.2 ml of piperidine and 1 ml of glacial acetic acid are added. The mixture is heated for 5 hours, using a water separator. It is then washed with water, dried over MgSO4 and concentrated. The product is recrystallized twice from methanol. 25.6 g (54percent of theory) of the title compound are obtained.

References: [1]Patent: US5652251,1997,A .

2
[ 83279-38-3 ]
[ 58379-80-9 ]
[ 1146695-92-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In methanol; for 2h;Heating / reflux;	A mixture of Example 45A (2.84 g, 13.6 mmol), 1-(1-isocyanoethylsulfonyl)-4-methylbenzene (2.85 g, 13.6 mmol), and K2CO3 (2.26 g, 16.3 mmol) in MeOH (70 mL) was heated to reflux. After 2 hr the reaction mixture was cooled to ambient temperature, and the volatiles were evaporated at reduced pressure. The residue was partitioned between Et2O and H2O. The separated aqueous layer was extracted with Et2O, and the combined organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. Flash chromatography (Analogix.(R). Intelliflash 280; 10percent to 30percent EtOAc/hexanes eluant; SF40-150 g column) yielded 3.04 g (85percent) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) delta 8.48 (s, 1H), 7.96 (d, J=8.4, 1H), 7.87 (s, 1H), 7.78 (dd, J=8.3, 0.8, 1H), 2.43 (s, 3H). MS (DCI+) m/z 262 (M+H).

References: [1]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 32.

3
[ 1092460-79-1 ]
[ 83279-38-3 ]

Yield	Reaction Conditions	Operation in experiment
74%		Diisobutylaluminum hydride (1.0 M in toluene, 28 mL, 28 mmol) was added slowly via syringe to a solution of 3-chloro-4-(trifluoromethyl)benzonitrile (3.79 g, 18.4 mmol) in THF (50 mL) at 0° C. The reaction was allowed to proceed for 2 hr, then warmed to ambient temperature and stirred an additional 2 hr. The reaction was then cooled to 0° C., and quenched with 3 M aq HCl (75 mL). The mixture was allowed to warm to ambient temperature, and stirred vigorously for 1.5 hr. The mixture was then transferred to a separatory funnel and diluted with Et2O. The separated organic phase was dried over Na2SO4, filtered, and concentrated in vacuo. Flash chromatography (Analogix.(R). Intelliflash 280.(TM).; 15percent EtOAc/hexanes eluant; SF40-150 g column) yielded 2.84 g (74percent) of the title compound as a colorless oil. 1H NMR (300 MHz, DMSO-d6) delta 10.09 (s, 1H), 8.21 (s, 1H), 8.12 (d, J=8.1, 1H), 8.07-8.02 (m, 1H).

References: [1]Patent: US2009/124666,2009,A1 .Location in patent: Page/Page column 30-32.

4
[ 83279-38-3 ]
[ 141-82-2 ]
[ 1092460-80-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3857 - 3863.

5
[ 83279-38-3 ]
C₁₇H₁₈ClF₃IN₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3857 - 3863.

6
[ 83279-38-3 ]
[ 1036395-95-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3857 - 3863.

7
[ 83279-38-3 ]
[ 1036396-40-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3857 - 3863.

8
[ 83279-38-3 ]
[ 1036395-80-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3857 - 3863.

9
[ 83279-38-3 ]
C₂₂H₂₆ClF₃IN₃O₂ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3857 - 3863.

10
[ 83279-38-3 ]
[ 1533424-28-0 ]
N₅-(3-chloro-4-(trifluoromethyl)benzyl)-N₃-(3,5-dichlorophenyl)-1H-[1,2,4]triazole-3,5-diamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%		To a solution of N3-(3,5-dichlorophenyl)-1H-1,2,4-triazole-3,5-diamine Intermediate 2 (200 mg, 819 mumomicronl) in MeOH (3.5 ml) was added <strong>[83279-38-3]3-chloro-4-(trifluoromethyl)benzaldehyde</strong> (94.0 mg 451 mumomicronl) followed by acetic acid (36.7 mg, 35.0 mu, 611 mumomicronl). The reaction was stirred at room temperature for 15 minutes, 2-picoline borane complex (52.6 mg, 492 mumomicronl) was added and the stirring was continued for 4 days. The reaction mixture was poured into 0.1N HC1 solution (20 ml). The resulting suspension was filtered to collect the solid. Purification by flash chromatography (silica gel, 24g, 2percent to 4percent MeOH in DCM) afforded a white solid as desired product (121.4 mg, 68percent yield). MS +m/z: 436 (M+H)+

References: [1]Patent: WO2014/135422,2014,A1 .Location in patent: Page/Page column 48.

11
[ 83279-38-3 ]
6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one [ No CAS ]
(E)-2-(3-chloro-4-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With toluene-4-sulfonic acid; In toluene; at 120℃; for 6h;	To a solution of 13 (550 mg, 2.226 mmol) in toluene 25 mL was added <strong>[83279-38-3]3-chloro-4-(trifluoromethyl)benzaldehyde</strong> 90 (464.2 mg, 2.226 mmol). PTSA (846.7 mg, 4.452 mmol) was added to the reaction, and stirred at 120° C. for 6 h, then diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude compound 91 which was purified through flash chromatography by using 100-200 mesh silica gel. The compound was eluted at 30percent ethyl acetate in hexane to afford yellow coloured solid compound (E)-2-(3-chloro-4-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 91.

References: [1]Patent: US2015/72980,2015,A1 .Location in patent: Paragraph 0192.

12
[ 83279-38-3 ]
[ 5334-72-5 ]
4-(3-chloro-4-trifluoromethylbenzylidene)-hydrazino-1-methyl-pyrazolo[3,4-d]pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With acetic acid; In ethanol;Reflux;	Hydrazine-1-methyl-1-hydro-pyrazolo [3,4-d] pyrimidine (100 mg, 609ymol) In a 25 mL single-neck flask, 10 mL of absolute ethanol was taken and 50 mg of acetic acid was added dropwise. The mixture was heated and stirred until the starting material was completely dissolved. To the above reaction system was added 3-chloro-4- trifluoromethylbenzaldehyde (254 mg, 1.2 mmol) , And the mixture was heated to reflux for 2.5h, then cooled to room temperature, filtered, the filter cake was washed with absolute ethanol, and recrystallized from anhydrous ethanol to obtain 200mg of a white solid with a yield of 92percent.

References: [1]Patent: CN104016985,2017,B .Location in patent: Paragraph 0120-0122.

13
[ 83279-38-3 ]
[ 1065010-87-8 ]
[ 1360911-54-1 ]
4-(8-(3-cyclopropyl-4-(trifluoromethyl)benzyl)-2-oxo-1-oxa-3,8-diazaspiro[4.5]decan-3-yl)benzoic acid [ No CAS ]