[ CAS No. 83279-38-3 ] {[proInfo.proName]}

Name: 83279-38-3|3-Chloro-4-(trifluoromethyl)benzaldehyde|95%
Brand: Ambeed
SKU: A538800
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Structure of 83279-38-3 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 83279-38-3 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 83279-38-3 ]

SDS Specification

Alternatived Products of [ 83279-38-3 ]

Product Details of [ 83279-38-3 ]

CAS No. :	83279-38-3	MDL No. :	MFCD03095197
Formula :	C₈H₄ClF₃O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	UTSBZTCYCRVHCK-UHFFFAOYSA-N
M.W :	208.57	Pubchem ID :	19031287
Synonyms :

Calculated chemistry of [ 83279-38-3 ]

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 :	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) :	-5.51 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.71
Log Po/w (XLOGP3) :	2.9
Log Po/w (WLOGP) :	4.32
Log Po/w (MLOGP) :	3.08
Log Po/w (SILICOS-IT) :	3.65
Consensus Log Po/w :	3.13

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.17
Solubility :	0.141 mg/ml ; 0.000677 mol/l
Class :	Soluble
Log S (Ali) :	-2.92
Solubility :	0.251 mg/ml ; 0.00121 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.85
Solubility :	0.0291 mg/ml ; 0.00014 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.41

Safety of [ 83279-38-3 ]

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 [ 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.

Upstream synthesis route of [ 83279-38-3 ]
Downstream synthetic route of [ 83279-38-3 ]

[ 83279-38-3 ] Synthesis Path-Upstream 1~1

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

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: With diisobutylaluminium hydride In tetrahydrofuran; toluene at 0 - 20℃; for 4 h; Stage #2: With hydrogenchloride; water In tetrahydrofuran; toluene at 0 - 20℃; for 1.5 h;	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) δ 10.09 (s, 1H), 8.21 (s, 1H), 8.12 (d, J=8.1, 1H), 8.07-8.02 (m, 1H).

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

[ 83279-38-3 ] Synthesis Path-Downstream 1~21

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.

Reference： [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).

Reference： [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).

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

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

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

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

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

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

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

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

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

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

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

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

Reference： [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)+

Reference： [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.

Reference： [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.

Reference： [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 ]