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Chemical Structure| 445-13-6 Chemical Structure| 445-13-6

Structure of 445-13-6

Chemical Structure| 445-13-6

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Product Details of [ 445-13-6 ]

CAS No. :445-13-6
Formula : C7H5ClF3N
M.W : 195.57
SMILES Code : NC1=CC=C(C(F)(F)F)C(Cl)=C1
MDL No. :MFCD00278479
InChI Key :KZAMRRANXJVDCD-UHFFFAOYSA-N
Pubchem ID :67962

Safety of [ 445-13-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H317-H319
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 445-13-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.14
Num. rotatable bonds 1
Num. H-bond acceptors 3.0
Num. H-bond donors 1.0
Molar Refractivity 40.86
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

26.02 Ų

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.65
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.75
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

4.1
Log Po/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.

3.15
Log Po/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

2.77
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.88

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.09
Solubility 0.159 mg/ml ; 0.000815 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.

-2.95
Solubility 0.219 mg/ml ; 0.00112 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

-3.54
Solubility 0.0558 mg/ml ; 0.000285 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.

-5.54 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

2.0
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)

1.24

Application In Synthesis of [ 445-13-6 ]

* 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 [ 445-13-6 ]

[ 445-13-6 ] Synthesis Path-Downstream   1~41

  • 3
  • [ 2401-85-6 ]
  • [ 445-13-6 ]
  • [ 68105-69-1 ]
  • 4
  • [ 654-55-7 ]
  • [ 445-13-6 ]
  • [ 72781-79-4 ]
  • 5
  • [ 445-13-6 ]
  • [ 2375-97-5 ]
  • [ 72773-12-7 ]
  • 6
  • [ 445-13-6 ]
  • [ 27738-96-1 ]
  • [ 35631-27-7 ]
  • [ 39886-32-3 ]
  • 7
  • [ 445-13-6 ]
  • [ 39893-50-0 ]
  • [ 23794-99-2 ]
  • 8
  • [ 75-63-8 ]
  • [ 108-42-9 ]
  • [ 445-14-7 ]
  • [ 445-13-6 ]
  • [ 432-21-3 ]
  • 9
  • [ 445-13-6 ]
  • [ 108-24-7 ]
  • [ 546434-30-4 ]
  • 10
  • [ 445-13-6 ]
  • [ 742097-64-9 ]
  • thiazole-4-carboxylic acid {4-[3-(3-chloro-4-trifluoromethyl-phenyl)-thioureido]-phenyl}-amide [ No CAS ]
  • 11
  • [ 445-13-6 ]
  • pyridine-2-carboxylic acid (4-isothiocyanato-phenyl)-amide [ No CAS ]
  • pyridine-2-carboxylic acid {4-[3-(3-chloro-4-trifluoromethyl-phenyl)-thioureido]-phenyl}-amide [ No CAS ]
  • 12
  • [ 445-13-6 ]
  • oxazole-4-carboxylic acid (4-isothiocyanato-phenyl)-amide [ No CAS ]
  • oxazole-4-carboxylic acid {4-[3-(3-chloro-4-trifluoromethyl-phenyl)-thioureido]-phenyl}-amide [ No CAS ]
  • 13
  • [ 151504-80-2 ]
  • [ 445-13-6 ]
YieldReaction ConditionsOperation in experiment
With sodium tetrahydroborate; In water; at 55℃; for 3h;Green chemistry; General procedure: To the corresponding nitro aromatic compound (1 mmol) in3mL water, 40 mg catalyst was added and the suspension wasstirred vigorously at ambient temperature. Subsequently, 2 mmolNaBH4 was added and the mixture heated to 55 C. Afterwards, theprogress of reduction process was monitored using thin layerchromatography until the complete reduction of nitro groups. After the reduction reaction completed, the catalyst was removed withan external magnet and washed with ethanol. The products werepurified by a short column chromatography over silica gel to obtainthe corresponding compounds in high purity. 1H NMR spectra andcomparison of melting points to authentic samples were used forrecognizing of the reaction products.
  • 14
  • [ 61982-14-7 ]
  • [ 445-13-6 ]
  • [ 929910-69-0 ]
  • 15
  • [ 1006962-20-4 ]
  • [ 445-13-6 ]
  • 2-methyl-4-nitro-2<i>H</i>-pyrazole-3-carboxylic acid (3-chloro-4-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 16
  • potassium 1H-[1,2,4]triazole-3-selenoxide [ No CAS ]
  • [ 445-13-6 ]
  • [ 873576-69-3 ]
  • 17
  • [ 445-13-6 ]
  • [ 105-56-6 ]
  • <i>N</i>-(3-chloro-4-trifluoromethyl-phenyl)-2-cyano-acetamide [ No CAS ]
  • 18
  • [ 951134-40-0 ]
  • [ 445-13-6 ]
  • Example 45 [ No CAS ]
YieldReaction ConditionsOperation in experiment
78% Example 45 N4-(3-Chloro-4-trifluoromethyl-phenyl)-N2,N2-dimethyl-7-(3-trifluoro-methyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine-2,4-diamine The title compound was synthesized like Example 39 with modifications to Step C as follows: Step C. A mixture of [4-chloro-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido-[4,5-d]azepin-2-yl]-dimethyl-amine (50 mg, 0.14 mmol), 3-chloro-4-trifluoro-methylaniline (40 mg, 0.20 mmol), and p-toluenesulfonic acid (51 mg, 0.27 mmol) in toluene (2 mL) was heated in a sealed tube at 120 C. for 18 h. The mixture was cooled, diluted with satd. aq. NaHCO3, and extracted with CH2Cl2. The organic layer was dried (MgSO4) and concentrated. The residue was purified (FCC) to give the title compound (55 mg, 78%). MS (ESI): mass calcd. for C23H21ClF6N6, 530.14; m/z found, 531.8 [M+H]+. 1H NMR (CD3OD): 8.43-8.40 (m, 1H), 8.25 (d, J=1.9 Hz, 1H), 8.08-7.98 (m, 1H), 7.66-7.62 (m, 1H), 7.57 (d, J=8.8 Hz, 1H), 7.11-7.08 (m, 1H), 3.45-3.39 (m, 4H), 3.33-3.31 (m, 1H), 3.13 (s, 6H), 3.06-3.03 (m, 2H), 2.97-2.93 (m, 2H).
  • 19
  • C11H11N3O2 [ No CAS ]
  • [ 445-13-6 ]
  • C18H14F3ClN4O [ No CAS ]
  • 20
  • C11H11N3O2 [ No CAS ]
  • [ 445-13-6 ]
  • C18H14ClF3N4O [ No CAS ]
  • 21
  • C15H13N3O2 [ No CAS ]
  • [ 445-13-6 ]
  • C22H16ClF3N4O [ No CAS ]
  • 22
  • C9H9N5O2 [ No CAS ]
  • [ 445-13-6 ]
  • C16H12ClF3N6O [ No CAS ]
  • 23
  • [ 445-13-6 ]
  • 5-amino-3-methyl-isoxazole-4-carboxylic acid (3-chloro-4-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 24
  • [ 445-13-6 ]
  • 2-cyano-3-ethoxy-but-2-enoic acid (3-chloro-4-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 25
  • [ 445-13-6 ]
  • 3-methyl-5-[(pyridin-4-ylmethylene)-amino]-isoxazole-4-carboxylic acid (3-chloro-4-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 26
  • [ 445-13-6 ]
  • 3-methyl-5-[(pyridin-4-ylmethyl)-amino]-isoxazole-4-carboxylic acid (3-chloro-4-trifluoromethyl-phenyl)-amide [ No CAS ]
  • 28
  • [ 445-13-6 ]
  • [ 35375-74-7 ]
  • 29
  • [ 445-13-6 ]
  • [ 157590-59-5 ]
  • 30
  • [ 445-13-6 ]
  • [ 153505-38-5 ]
  • 31
  • [ 445-13-6 ]
  • [ 1026318-97-7 ]
  • 32
  • [ 445-13-6 ]
  • 6-chloro-5-nitro-7-trifluoromethyl-1,4-dihydroquinoxaline-2,3-dione [ No CAS ]
  • 33
  • [ 445-13-6 ]
  • [ 32333-53-2 ]
YieldReaction ConditionsOperation in experiment
Following the procedure of N. Ikemoto et al. (Tetrahedron, 59:1317 (1998)), <strong>[445-13-6]3-chloro-4-trifluoromethylaniline</strong> (890 mg, 4.6 mmol, Ryan Scientific) in CH3CN (37 mL) was added to a 250 mL round-bottomed flask. The flask was cooled in an ice bath, and HOAc (3.7 mL) and HCl (12 M, 1.8 mL) were added. Sodium nitrite (380 mg, 5.5 mmol, Aldrich) in 0.77 mL of H2O was added in 0.15 mL portions every 2 min until all of the solution had been added (total time ca. 9 min). After 25 min, sulfur dioxide (Aldrich) was bubbled into the reaction mixture for 1.25 h. Copper(II)chloride (780 mg, 5.8 mmol, Aldrich) in 1.5 mL of water was then added to the reaction mixture. Gas evolution occurred, and the reaction was warmed to RT and stirred overnight. After the lower boiling solvents were removed in vacuo, water was added, and the mixture was extracted with CH2Cl2 (3×). The combined organic layers were washed with water, dried over MgSO4, filtered and concentrated in vacuo to give the crude material as a brownish oil with solid in it. The compound did not ionize well, but an aliquot, when treated with propylamine, provided the propylarylsulfonamide adduct with a ESI-MS, -ion, m/z=300.2 (M-1).
  • 34
  • [ 445-13-6 ]
  • [ 37900-81-5 ]
YieldReaction ConditionsOperation in experiment
48% With sulfuric acid; water; sodium nitrite; at 0 - 110℃; for 3h;Heating / reflux; To a sulfuric acid (14 ml) -H2O (14 ml) solution of <strong>[445-13-6]3-chloro-4-(trifluoromethyl)aniline</strong> (1.96 g, 10 mmol) was added a H2O (10 mL) solution of sodium nitrite (828 mg,12 mmol) at 0 C. The reaction mixture was stirred at ambient temperature for 1 hour. The mixture was poured into 10 M sulfuric acid (50 mL). The stirred mixture was refluxed at 110 C. for 2 hours. The reaction mixture was then quenched with saturated aqueous solution of sodium bicarbonate and then crude products were extracted with ethyl acetate The organic layer was then washed with brine, dried over sodium sulfate. After the filtration to separate solvent and sodium sulfate, the solvent was removed under reduced pressure to give the residue, which was applied to a silica gel chromatography column and eluted with a ethyl acetate/hexane= to furnish 945 mg (48% yield) of the title compound as a brown oil. 1H NMR (CDCl3, 270 MHz) delta ppm 5.99 (1H, brs), 6.80 (1H, dd, J=2.6, 8.6 Hz), 7.00 (1H, d, J=2.6 Hz), 7.56 (1H, d, J=8.6 Hz). MS (ESI) m/z: 195[M-H-.
  • 35
  • [ 445-13-6 ]
  • [ 1885-14-9 ]
  • [ 894801-69-5 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In tetrahydrofuran; for 18h; Phenyl [3-chloro-4-(trifluoromethyl)phenyl]carbamate; Phenyl chloroformate (0.86 mL) was added slowly to a stirring solution of 3-chloro-4- trifluoromethyl aniline (933 mg) in THF (10 mL) containing pyridine (1.07 mL) under an argon atomosphere. The reaction was stirred for 18 h then diluted with ethyl acetate (35 mL) and IM HCl (20 mL). The organic layer was separated and washed with saturated aqueous NaHCO3 then dried (MgSO4), filtered and evaporated. Trituration with 1:9 EPO <DP n="183"/>EtOAc dsohexanes (10 mL) at reflux followed by cooling to RT afforded a solid which was filtered to afford 1.15 g of the title compound.
  • 36
  • [ 445-13-6 ]
  • [ 76-02-8 ]
  • [ 894801-68-4 ]
YieldReaction ConditionsOperation in experiment
69% With pyridine; In dichloromethane; for 2h; l^^-Trichloro-N-tS-chloro^^trifluoromethy^phenyllacetaiiiide; To a solution of 4-amino-2-chlorobenzotrifluoride (300 mg) and pyridine (243 mg) in dichloromethane (1OmL) was added a solution of trichloro acetyl chloride (279 mg) in dichloromethane (5mL) dropwise. The solution was stirred for 2hrs and then concentrated at reduced pressure. The residue was purified by silica gel chromatography eluting with 0-10% ethyl acetate in hexane to give the title compound as a white solid (360mg, 69%).
  • 37
  • [ 496808-03-8 ]
  • [ 445-13-6 ]
  • N-[3-chloro-4-(trifluoromethyl)phenyl]-4-[(1-methylpiperidin-3-yl)methyl]piperazine-1-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
iV-tS-CIiloro^-CtrifluoromethylJphenyy^-fCl-methylpiperidin-S- yl)methyl]pipera-ne-l-carboxaniotaide; To a solution of di-tert-butyl dicarbonate (114.6 mg) in chloroform (2 ml) was added 4-dimethylaminopyridine (6 mg). A solution of 4-amino-2-chlorobenzotrifluoride(98.1 mg) in chloroform (2 ml) was added and the reaction mixture stirred for 20 minutes at room temperature. A solution of l-[(l-methylpiperidm-3-yl)methyl]piperazine (98.5 mg) in chloroform (2 ml) was added and the resulting solution was stirred at reflux for 18 hours. The reaction mixture was purified by column chromatography on silica gel (20 g) using a gradient of 100% dichloromethane through to 20% methanolic ammonia in dichloromethane to give the title compound (14 mg).
  • 38
  • [ 445-13-6 ]
  • [ 1885-14-9 ]
  • [ 371-40-4 ]
  • [ 78015-62-0 ]
YieldReaction ConditionsOperation in experiment
67% With triethylamine; In 1,2-dichloro-benzene; Example 2 (variant b) STR11 0.5 mol of chloroformic acid phenyl ester is added to a solution of 0.5 mol of p-fluoroaniline in 300 ml of dichlorobenzene and 70 ml (0.5 mol) of triethylamine, whilst cooling (0-10 C.). The reaction mixture is then left to stand at room temperature for 24 hours. The triethylamine hydrochloride which has formed is filtered off and 0.5 mol of <strong>[445-13-6]3-chloro-4-trifluoromethylaniline</strong> is added to the filtrate. The reaction solution is heated to 180 C. for 6 hours, the solvent is stripped off in vacuo and the residue is boiled up in 250 ml of ether and filtered off again. N-4-Fluorophenyl-N'-3-chloro-4-trifluoromethylphenylurea of melting point 212 to 214 C. is obtained. Yield: 67% of theory.
  • 39
  • [ 100-34-5 ]
  • [ 445-13-6 ]
YieldReaction ConditionsOperation in experiment
It was prepared by diazotizing of 3-chloro-4-trifluoromethylaniline and subsequent reduction of the corresponding phenyldiazonium chloride with tin(II) chloride.
  • 40
  • [ 445-13-6 ]
  • [ 932374-43-1 ]
YieldReaction ConditionsOperation in experiment
93% With Iodine monochloride; In methanol; dichloromethane; at 0℃; Step 1 5-Chloro-2-iodo-4-(trifluoromethyl)phenylamine A 250 mL 3-necked round bottom flask was charged with <strong>[445-13-6]3-chloro-4-(trifluoromethyl)aniline</strong> (4.5 g, 0.02 mol) and MeOH (50 mL). To the above was added dropwise a solution of IC1 (4.8 g, 0.03 mol) in CH2Cl2 (100 mL) at 0 C. The resulting mixture was stirred at room temperature for 1 h. Reaction progress was monitored by TLC (EtOAc/Petroleum ether=1:20, Rf=0.6). Work-up: the mixture was concentrated in vacuo. The residue was re-dissolved in CH2Cl2, washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo, to give 6.9 g (93%) of the product. MS m/z: 320 (M-H+).
93% With Iodine monochloride; In methanol; dichloromethane; at 0 - 20℃; for 1h; A 250 mL 3-necked round bottom flask was charged with 3-chloro-4- (trifluoromethyl)aniline (4.5 g, 0.02 mol) and MeOH (50 mL). To the above was added dropwise a solution of ICl (4.8 g, 0.03 mol) in CH2C12 (100 mL) at 0 C. The resulting mixture was stirred at room temperature for 1 h. Reaction progress was monitored by TLC (EtO Ac/Petroleum ether = 1 :20, Rf = 0.6). Work-up: the mixture was concentrated in vacuo. The residue was re-dissolved in CH2C12, washed with water, dried over anhydrous Na2SC>4 and concentrated in vacuo, to give 6.9 g (93%) of the product. MS m/z: 320 (M-H+).
With sodium acetate; Iodine monochloride; In acetic acid; at 20℃; for 0.5h; Iodine monochloride (1.5 g) was added in one portion to a mixture of 3-chloro-4- trifluoromethylaniline (1.7 g), sodium acetate trihydrate (2.2 g), and acetic acid (10 ml) at room temperature. After 30 min aqueous sodium bicarbonate / sodium sulfite was added and the mixture extracted with diethyl ether. The organic phase was dried over Na2SO4, filtered and evaporated. The residue was purified by chromatography (ethyl acetate - hexane) to afford the title compound, 2.2 g.
  • 41
  • [ 445-13-6 ]
  • [ 467435-07-0 ]
YieldReaction ConditionsOperation in experiment
50% With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 45℃; for 3h; A solution of 4-amino-2-chlorobenzotrifluoride (9.780 g; 50.007 mmol) in MeCN (65 ml) was treated with copper(ll) bromide (1 1.169 g; 50.007 mmol), and the green heterogeneous mixture was heated to 45C. A solution of tert-butyl nitrite (6.53 ml; 55.008 mmol) in MeCN (10 ml) was then added dropwise over 30 min., and the resulting mixture was further stirred at 45C for 2h20. The dark heterogeneous reaction mixture was allowed to cool to rt, and was directly purified by FC (DCM). After concentration to dryness under reduced pressure, the expected product 4-bromo-2-chloro-1-trifluoromethyl-benzene was obtained as a yellow oil (12.82O g; 50%). LC-MS: tR = 1.10 min.; [M+H]+: no ionisation.
 

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2-Amino-6-chlorobenzotrifluoride

Similarity: 0.86

Chlorides

Chemical Structure| 39885-50-2

A672393 [39885-50-2]

2-Chloro-4-(trifluoromethyl)aniline

Similarity: 0.89

Chemical Structure| 40566-70-9

A170931 [40566-70-9]

(4-Chloro-3-(trifluoromethyl)phenyl)hydrazine hydrochloride

Similarity: 0.88

Chemical Structure| 1804908-04-0

A217765 [1804908-04-0]

2,4-Dichloro-3-(trifluoromethyl)aniline

Similarity: 0.88

Chemical Structure| 69411-05-8

A135464 [69411-05-8]

3-Chloro-5-trifluoromethylaniline

Similarity: 0.87

Chemical Structure| 432-21-3

A341540 [432-21-3]

2-Amino-6-chlorobenzotrifluoride

Similarity: 0.86

Amines

Chemical Structure| 39885-50-2

A672393 [39885-50-2]

2-Chloro-4-(trifluoromethyl)aniline

Similarity: 0.89

Chemical Structure| 40566-70-9

A170931 [40566-70-9]

(4-Chloro-3-(trifluoromethyl)phenyl)hydrazine hydrochloride

Similarity: 0.88

Chemical Structure| 1804908-04-0

A217765 [1804908-04-0]

2,4-Dichloro-3-(trifluoromethyl)aniline

Similarity: 0.88

Chemical Structure| 69411-05-8

A135464 [69411-05-8]

3-Chloro-5-trifluoromethylaniline

Similarity: 0.87

Chemical Structure| 432-21-3

A341540 [432-21-3]

2-Amino-6-chlorobenzotrifluoride

Similarity: 0.86

Trifluoromethyls

Chemical Structure| 39885-50-2

A672393 [39885-50-2]

2-Chloro-4-(trifluoromethyl)aniline

Similarity: 0.89

Chemical Structure| 40566-70-9

A170931 [40566-70-9]

(4-Chloro-3-(trifluoromethyl)phenyl)hydrazine hydrochloride

Similarity: 0.88

Chemical Structure| 1804908-04-0

A217765 [1804908-04-0]

2,4-Dichloro-3-(trifluoromethyl)aniline

Similarity: 0.88

Chemical Structure| 69411-05-8

A135464 [69411-05-8]

3-Chloro-5-trifluoromethylaniline

Similarity: 0.87

Chemical Structure| 432-21-3

A341540 [432-21-3]

2-Amino-6-chlorobenzotrifluoride

Similarity: 0.86