2-Methyl-3-(trifluoromethyl)aniline | 3-Trifluoromethyl-2-methylaniline | Trifluoromethyls

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of 2-Methyl-3-(trifluoromethyl)aniline Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of 2-Methyl-3-(trifluoromethyl)aniline

CAS No. :	54396-44-0
Formula :	C₈H₈F₃N
M.W :	175.15
SMILES Code :	NC1=CC=CC(C(F)(F)F)=C1C
Synonyms :	3-Trifluoromethyl-2-methylaniline
MDL No. :	MFCD00153216
InChI Key :	TWLDBACVSHADLI-UHFFFAOYSA-N
Pubchem ID :	2735932

Safety of 2-Methyl-3-(trifluoromethyl)aniline

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

Application In Synthesis of 2-Methyl-3-(trifluoromethyl)aniline

* 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 [ 54396-44-0 ]

[ 54396-44-0 ] Synthesis Path-Downstream 1~35

1
[ 54396-44-0 ]
[ 16497-87-3 ]
N-3-(trifluoromethyl)phenylanthranilic acid [ No CAS ]

References: [1]Arzneimittel-Forschung/Drug Research,1983,vol. 33,p. 621 - 627.

2
[ 54396-44-0 ]
[ 1452-94-4 ]
[ 54396-42-8 ]

References: [1]Heterocycles,1994,vol. 38,p. 2243 - 2246.

3
[ 150783-50-9 ]
[ 54396-44-0 ]

Yield	Reaction Conditions	Operation in experiment
98.5%	With hydrogenchloride; In ethanol;	Preparation of 2-Methyl-3-Trifluoromethyl-Aniline A solution of 2,2,2'-trimethyl-3'-trifluoromethyl-propionanilide (10 g.) in 75 ml. ethanol and 75 ml. concentrated HCl was refluxed for 24 hours. The reaction mixture was then concentrated in vacuo and diluted with water. It was then basified with 10percent NaOH solution and extracted with ether. The ether extract was washed with water and brine and dried with MgSO4. Removal of ether gave a pale brown liquid (6.65 g., 98.5percent) which was purified by distillation under reduced pressure (b.p. 108°-110° C., 30 mm.) to give 5.73 g. of 2-methyl-3-trifluoromethyl-aniline which solidified on standing. The physical and spectroscopic properties of the product were found to be identical to those of an authentic sample of 2-methyl-3-trifluoromethyl-aniline prepared by the known method below. STR2

References: [1]Patent: US5248781,1993,A .
[2]Heterocycles,1994,vol. 38,p. 2243 - 2246.

Yield	Reaction Conditions	Operation in experiment
96%		The CH2 Cl2 extracts are dried over K2 CO3 and evaporated to give 2-methyl-3-trifluoromethyl-aniline (MTA) (6.5 g, 96percent yield), an oil which solidifies on standing. STR13 iv.) A mixture of 2-methyl-3-trifluoromethylaniline (368 g, 2.1 moles) and 2-chloronicotinic acid (158.0 9, 1.0 mole) in 400 ml of water is heated at 100° C. for 24 hours together with p-toluenesulfonic acid (15.0 g) monohydrate as the acid catalyst. Potassium hydroxide (ca. 145 g) in water (255 ml) is added and the pH is maintained above 11. After diluting the reaction mixture to 1.2 liters with water, the mixture is cooled to 50° C., adjusted to pH 11, treated with 7 g of a decolorizing charcoal and 15 g of a filter aid, and clarified by filtration. The filtrate is diluted with 750 ml of water and the pH is adjusted to 5.0 with concentrated sulfuric acid.
96%		iii.) 2-methyl-3-trifluoromethylpivalanilide (10.0 g)is hydrolyzed by refluxing in concentrated HBr (40 ml, 48percent) for 3 hours. The mixture is cooled to 20° C. and poured onto ice-water (40.0 g). The pH is adjusted to 9 with concentrated NaOH and the mixture is extracted with two. 30 ml portions of CH2 Cl2. The CH2 Cl2 extracts are dried over K2 CO3 and evaporated to give 2-methyl-3-trifluoromethyl-aniline (MTA) (6.5 g, 96percent yield), an oil which solidifies on standing. STR13
		Following the procedure of Example 1, the following substituted aniline compounds:...3-fluoro-2-methylaniline3-iodo-2-methylaniline3-trifluoromethyl-2-methylaniline

5
[ 56-23-5 ]
[ 95-53-4 ]
[ 25449-96-1 ]
[ 54396-44-0 ]

References: [1]Tetrahedron Letters,2003,vol. 44,p. 1747 - 1750.

6
[ 1019327-29-7 ]
[ 54396-44-0 ]
[ 913067-77-3 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5671 - 5686.

7
3-(2-amino-quinazolin-6-yl)-4-methyl-benzoyl chloride [ No CAS ]
[ 54396-44-0 ]
3-(2-amino-6-quinazolinyl)-4-methyl-N-(2-methyl-3-(trifluoromethyl)phenyl)benzamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 5671 - 5686.

8
[ 54396-44-0 ]
[ 108-24-7 ]
[ 546434-38-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

9
[ 54396-44-0 ]
[ 98-59-9 ]
[ 947407-68-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4450 - 4455.

10
[ 54396-44-0 ]
C₂₆H₂₄N₃SO₄F₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4450 - 4455.

11
[ 54396-44-0 ]
[ 947407-70-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4450 - 4455.

12
[ 54396-44-0 ]
[ 947407-75-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 4450 - 4455.

13
[ 54396-44-0 ]
[ 573764-86-0 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

14
[ 54396-44-0 ]
[ 627531-79-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

15
[ 54396-44-0 ]
C₁₆H₁₆F₃N₃O₄ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

16
[ 54396-44-0 ]
C₁₅H₁₂F₃N₃O₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

17
[ 54396-44-0 ]
N-[4-bromo-2-methyl-3-(trifluoromethyl)phenyl]acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

18
[ 54396-44-0 ]
C₁₁H₉F₃N₂O [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1860 - 1864.

19
[ 1939-19-1 ]
[ 54396-44-0 ]

References: [1]Heterocycles,1994,vol. 38,p. 2243 - 2246.

20
[ 54396-44-0 ]
[ 38677-85-9 ]

References: [1]Heterocycles,1994,vol. 38,p. 2243 - 2246.

21
[ 98-16-8 ]
[ 54396-44-0 ]

References: [1]Heterocycles,1994,vol. 38,p. 2243 - 2246.

22
hydroxyammonium sulfate [ No CAS ]
[ 302-17-0 ]
[ 54396-44-0 ]
[ 851045-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium sulfate; In water; at 35 - 75℃; for 3.5h;	Example 135 Synthesis of (+/-)-Isopropyl 5- [acetyl- (3, 5-bistrifluoromethylbenzyl) amino]-9-methyl-8- trifluoromethyl-tetrahydrobenzo [b] azepine-1-carboxylate Step 1. Preparation of 7-methyl-6-trifluoromethyl-lH-indole, 2,3-dione To a solution of chloral hydrate (6.08 g, 36.74 mmol) and anhydrous sodium sulfate (28.5 g, 200.4 mmol) in water (102 mL) add a mixture of hydroxylamine sulfate (28.5 g, 173.68 mmol), 2-methyl-3-trifluoromethyl-phenylamine (5.85 g, 33.4 mmol), concentrated hydrochloric acid (3.5 mL) in water (34 mL). Heat the mixture at 35 °C for 1 h, then heat up to 52 °C for 90 min and at 75°C for 1 hr. Cool the mixture to room temperature and filter the solid. Wash the solid with water and hexane. Dry the solid under vacuum to afford 2-hydroxyimino-N- (2-methyl-3-trifluoromethyl-phenyl)- acetamide. MS (ES+): 245 (M-H). Add the former crude in small portions at 60°C to concentrated sulfuric acid (44 mL) and heat the mixture at 80°C for 1 h. Cool to room temperature, pour into ice water (100 mL) and filter the precipitate. Wash the solid with cool water twice. Dry the solid to afford the title compound (3.54 g, 46percent two steps). MS (ES-): 228 (M-H).

References: [1]Patent: WO2005/37796,2005,A1 .Location in patent: Page/Page column 133-134.

23
[ 54396-44-0 ]
[ 75-87-6 ]
[ 851045-50-6 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydroxylamine sulfate; sodium sulfate; In water; at 35 - 75℃; for 3.5h;	Example 53; Synthesis of (+/-)-isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-(2-methyl-2fl-tetrazol-5-yl)-amino]-9-methyl-8-trifluormethyl-2,3,4,5-tetrahydrobenzo[]azepine-l-carboxylate; Step 1; Preparation of 7-methyl-6-trifluoromethyl-lH-indole,2,3-dione; To a solution of chloral hydrate (6.08 g, 36.74 mmol) and anhydrous sodium sulfate (28.5g, 200.4 mmol) in water (102 mL) add a mixture of hydroxylamine sulfate (28.5 g,173.68 mmol), 2-methyl-3-trifluoromethyl-phenylamine (5.85 g, 33.4 mmol),concentrated hydrochloric acid ( 3.5 mL) in water (34 mL). Heat the mixture at 35 °C for1 h, then heat up to 52 °C for 90 min and at 75 °C for 1 h. Cool the mixture to roomtemperature and filter the solid. Wash the solid with water and hexane. Dry the solidunder vacuum to afford 2-hydroxyimino-N-(2-methyl-3-trifluoromethyl-phenyl)-acetamide: MS (ES+): 245 (M-H). Add the former crude in small portions at 60 °C toconcentrated sulfuric acid (44 mL) and heat the mixture at 80 °C for 1 h. Cool to roomtemperature, pour into ice water (100 mL) and filter the precipitate. Wash the solid withcool water twice. Dry the solid to afford the title compound (3.54 g, 46percent two steps).

References: [1]Patent: WO2006/2342,2006,A1 .Location in patent: Page/Page column 115-116.

24
[ 2942-59-8 ]
[ 54396-44-0 ]
[ 38677-85-9 ]

Yield	Reaction Conditions	Operation in experiment
97.1%	With perfluorosulfonic acid resin; In water; at 65 - 70℃; for 2.5h;Industrial scale;	300 L of water was added to a 1000 L reactor, 131.9 kg (837.5 mol) of 2-chloronicotinic acid and 140 kg of <strong>[54396-44-0]2-methyl-3-trifluoromethylaniline</strong> (800 mol) were added separately, stirred, 1.4kg perfluorosulfonated resin was added, the temperature was raised to 65 °C -70 °C, and reacted for 2.5h.Filtered, the filtrate was adjusted to pH 4.5 with a 60percent sulfuric acid solution, stirred for 15-20min, filtered , filter cake was washed with 30kg of water, filter cake was dried to obtain 230.1 kg of flunixin, the yield was 97.1percent, and the purity was 99.9percent, purity was tested according to the method of USP38, the same below.
83%	With potassium hydroxide; toluene-4-sulfonic acid; In water;	iv.) A mixture of <strong>[54396-44-0]2-methyl-3-trifluoromethylaniline</strong> (368 g, 2.1 moles) and 2-chloronicotinic acid (158.0 g, 1.0 mole) in 400 ml of water is heated at 100° C. for 24 hours together with p-toluenesulfonic acid (15.0 g) monohydrate as the acid catalyst. Potassium hydroxide (ca. 145 g) in water (255 ml) is added and the pH is maintained above 11. After diluting the reaction mixture to 1.2 liters with water, the mixture is cooled to 50° C., adjusted to pH 11, treated with 7 g of a decolorizing charcoal and 15 g of a filter aid, and clarified by filtration. The flitrate is diluted with 750 ml of water and the pH is adjusted to 5.0 with concentrated sulfuric acid. Agitation of the suspension for 10 minutes and filtration gives crude, precipitated 2-[[2-methyl-3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic acid (flunixin) (83percent yield). The compound can be further purified by crystallization in methanol and washing with water.
	With toluene-4-sulfonic acid; copper(II) oxide; sodium hydroxide; In 1,2-dimethoxyethane; water; at 45℃; for 0.6h;	(1) 2-chloronicotinic acid and <strong>[54396-44-0]2-methyl-3-trifluoromethylaniline</strong> are stirred and added to an aqueous sodium hydroxide solution, 2-chloronicotinic acid and 2-methyl-3-trifluoromethyl The molar ratio of aniline is 3:1; the molar ratio of 2-chloronicotinic acid to sodium hydroxide used to prepare aqueous sodium hydroxide solution is 1:2; ethylene glycol and chain polyethylene glycol dialkyl are added. The ether and the catalyst A, the chain polyethylene glycol dialkyl ether is used in an amount of 3percent of the mass of 2-chloronicotinic acid; the catalyst A is p-toluenesulfonic acid and copper oxide, the pair The molar ratio of toluenesulfonic acid to copper oxide is 3:1; the temperature is controlled at 45 ° C, after 0.6 hours of reaction, the pH of the solution is adjusted, stirred and allowed to stand for stratification, stirred, filtered, and the filter cake is washed and dried to obtain flunixin.;

References: [1]Patent: CN108586327,2018,A .Location in patent: Paragraph 0025; 0026; 0027; 0028.
[2]Patent: US5484931,1996,A .
[3]Patent: CN109206365,2019,A .Location in patent: Paragraph 0022-0024; 0026-0037; 0042-0045; 0054-0057.

25
[ 54396-44-0 ]
[ 863111-55-1 ]

Yield	Reaction Conditions	Operation in experiment
73%		3-Amino-2-methylbenzotrifluoride (Aldrich Co., 5.25 g) was added to a mixture of concentrated hydrochloric acid (20 ml) and water (20 ml) and, under ice-cooling, sodium nitrite (3.31 g) dissolved in water (10 ml) was added dropwise thereto. The mixture was stirred at 0°C for 1 hr. Potassium iodide (9.95 g) dissolved in water (20 ml) was added to the reaction mixture. The mixture was stirred at -4°C for 2 hr. The mixture was adjusted to pH 11 or above with a 6N aqueous sodium hydroxide solution, and an aqueous thiosodium sulfate solution was added thereto. The mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried. The solvent was evaporated under reduced pressure to give a brown oil. The oil was purified by silica gel column chromatography (elution solvent: hexane) to give 3-iodo-2-methylbenzotrifluoride (6.28 g, yield 73percent). 1H-NMR(400MHz,DMSO-d6)delta(ppm): 2.52 (3H,s), 7.16(1H,t,J=7.8Hz), 7.73(1H,d,J=7.8Hz), 8.18(1H,d,J=7.8Hz). By a similar operation as in Starting Material Synthetic Example 59, 4-[2-methyl-3-(trifluoromethyl)phenyl]piperidin-4-ol (2.18 g, yield 32percent) was obtained from 3-iodo-2-methylbenzotrifluoride (6.28 g). 1H-NMR(400MHz,DMSO-d6)delta(ppm) : 1.76-1.91(4H,m), 2.69-2.78(2H,m), 2.71(3H,s), 2.94-3.04(2H,m), 4.91(1H,s), 7.34(1H,t,J=7.8Hz), 7.57(1H,d,J=7.8Hz), 7.70(1H,d,J=7.8Hz).

References: [1]Organic Letters,2008,vol. 10,p. 5095 - 5097.
[2]Patent: EP1714961,2006,A1 .Location in patent: Page/Page column 31.

26
copper(II) oxide powder [ No CAS ]
[ 54396-44-0 ]
[ 107-13-1 ]
2-chloro-3-(2-methyl-3-trifluoromethyl-phenyl)-propionitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium nitrite; In dichloromethane; water;	STR12 20 mol of concentrated hydrochloric acid is added at 0°-5° C. to a suspension of 16.7 g of <strong>[54396-44-0]2-methyl-3-trifluoromethylaniline</strong> (0.095 mol) in 50 ml of water and the mixture is then briefly warmed to 60°-80° C. until a clear solution has formed. The solution is cooled very rapidly to 0°-5° C. with vigorous stirring, 22.4 ml (0.286 mol) of acrylonitrile are added dropwise to the fine suspension at 0°-5° C. and a solution of 6.75 g of sodium nitrite in 10 ml of water is then rapidly added, and the mixture is kept at 5° C. for a further 5 minutes and stirred at 20° C. for 1 hour. After cooling, 0.8 g of copper(II) oxide powder is added to the reaction mixture at 0°-10° C. in portions, a vigorous evolution of nitrogen gas occurring. After completion of the evolution of gas, the mixture is stirred for a further 2 hours at 0°-10° C., then for 15 hours at room temperature, dichloromethane is added, and the mixture is washed with water, dried over sodium sulphate and concentrated in vacuo. 21.2 g (90percent of theory) of 2-chloro-3-(2-methyl-3-trifluoromethylphenyl)-propionitrile are obtained as a brown oil. M/e 247 (+), 228, 212, 173 (100percent)

References: [1]Patent: US5091408,1992,A .

27
[ 6656-49-1 ]
[ 54396-44-0 ]

Yield	Reaction Conditions	Operation in experiment
92%	With hydrogen; In methanol;	C. 3-Amino-2-Methylbenzotrifluoride A solution of 2-methyl-3-nitrobenzotrifluoride (41.0 g, 0.2 m) in methanol (100 ml) was stirred under an atmosphere of dry nitrogen at room temperature and palladium on charcoal catalyst (10percent w/w, 1.0 g) was added. The stirred mixture was warmed to 40°-45° and then hydrogen was passed into the solution at atmospheric pressure until the reduction, as observed by thin-layer chromatography, was complete (4-5 hours). The solution was cooled to room temperature and the catalyst removed by filtration. Distillation of the solvent at atmospheric pressure followed by steam distillation of the crude product gave 3-amino-2-methylbenzotrifluoride (32.2 g, 92percent yield), as a pale-brown oil which slowly crystallized.
	palladium;	187 g. of 2-nitro-6-trifluoromethyltoluene were reduced with hydrogen over a palladium-on-carbon catalyst to yield 153.9 g. of a red oil comprising 3-trifluoromethyl-2-methylaniline.

References: [1]Patent: US4831193,1989,A .
[2]Patent: US4132737,1979,A .

28
[ 2516-96-3 ]
[ 54396-44-0 ]
[ 12775-96-1 ]
[ 61708-31-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In pentan-1-ol;	EXAMPLE 5 5-Nitro-N-(2-methyl-3-trifluoromethylphenyl) anthranilic acid To a solution of 25 g. of 2-chloro-5-nitro-benzoic acid in 125 ml. of n-pentyl alcohol add 4.8 g. of sodium hydroxide pellets, 25 g. of <strong>[54396-44-0]2-methyl-3-trifluoromethylaniline</strong> and 2 g. of copper powder. With constant stirring, reflux the reaction mixture for 18 hours. Concentrate the mixture to one half volume and dilute with water and ether. Acidify the aqueous layer to obtain a crude product which is recrystallized to yield 5-nitro-N-(2-methyl-3-trifluoromethylphenyl) anthranilic acid, m.p. 244°-245° C.

References: [1]Patent: US4029815,1977,A .

29
[ 54396-44-0 ]
[ 12775-96-1 ]
[ 50-79-3 ]
[ 61708-30-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In pentan-1-ol;	EXAMPLE 4 5-Chloro-N-(2-methyl-3-trifluoromethylphenyl) anthranilic acid To a solution of 25 g. of 2,5-dichlorobenzoic acid in 125 ml. of n-pentyl alcohol add 4.8 g. of sodium hydroxide pellets, 25 g. of <strong>[54396-44-0]2-methyl-3-trifluoromethylaniline</strong> and 2 g. of copper powder. With constant stirring, reflux the reaction mixture for 18 hours. Concentrate the mixture to one half volume and dilute with water and ether. Acidify the aqueous layer to yield the product which is recrystallized from methanol, m.p. 220°-222° C.

References: [1]Patent: US4029815,1977,A .

30
[ 62639-16-1 ]
[ 54396-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	aluminum nickel; In methanol;	C. 3-amino-2-methylbenzotrifluoride Wash 5 to 10 teaspoonfuls of W-2 Raney nickel catalyst with distilled water to neutrality, then three times with absolute alcohol. Dissolve 10 g. of 3-amino-2-methylthiomethylbenzotrifluoride in 100 ml. of methanol and add 4 teaspoonfuls of the washed W-2 Raney nickel. Reflux for 4 hours, filter to remove the catalyst and evaporate the solvent in vacuo to yield the title compound. Alternatively, the 3-amino-2-methylthiomethylbenzotrifluoride may be chemically reduced by the following technique.
	aluminum nickel; In methanol;	B. 3-Amino-2-methylbenzotrifluoride Wash 5 to 10 teaspoonsful of W-2 Raney nickel catalyst with distilled water to neutrality, then three times with absolute alcohol. Dissolve 10 g. of 3-amino-2-methylthiomethylbenzotrifluoride in 100 ml. of methanol and add 4 teaspoonsful of the W-2 Raney nickel. Reflux for 4 hours, filter to remove catalyst and evaporate solvent in vacuo to yield the title compound.

References: [1]Patent: US4209464,1980,A .
[2]Patent: US4172095,1979,A .

31
[ 62639-16-1 ]
[ 7440-66-6 ]
[ 54396-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In water; isopropyl alcohol;	C'. 3-amino-2-methylbenzotrifluoride Stir a mixture of 5 g. of 3-amino-2-methylthiomethylbenzotrifluoride, 12.5 ml of isopropanol, 15 g. of zinc powder and 2.5 ml of water in a 500 ml, 3-necked round bottom flask fitted with mechanical stirrer, dropping funnel with a nitrogen inlet, and reflux condenser with Clorox trap, and bubble-counter. Immerse the flask in an oil bath at 80° C. Slowly add a solution of 30 ml of water and 15 ml of acetic acid to the well-stirred mixture via the dropping funnel (about 2.5 ml per portion and 20 minutes for each portion). Stir the reaction mixture at 80° C. and cool the reaction mixture. Add 50 ml of water and extract three times with hexane. Dry the combined organic extracts and evaporate to yield the title compound which may be steam distilled for further purification.

References: [1]Patent: US4209464,1980,A .

32
[ 54396-44-0 ]
[ 54396-42-8 ]
[ 1452-94-4 ]
[ 38677-85-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In methanol; water;	EXAMPLE 4 2-(2'-Methyl-3'-trifluoromethylanilino) nicotinic acid To 20 g. of <strong>[54396-44-0]2-methyl-3-trifluoromethyl aniline</strong> heated at 200°, add, in a dropwise fashion, 11 g. of ethyl 2-chloro-nicotinate. Heat the reaction mixture at 200° for one-half hour, cool, pour the mixture onto ice and extract with ether. Concentrate the ether extracts, dry and fractionate the residue in vacuo; b.p. 143°-146°/0.15 mm; m.p. 44°-46°. To a solution of 12 g. of ethyl 2-(2'-methyl-3'-trifluoromethylanilino) nicotinate in 100 ml. of methanol and 4.6 g. of potassium hydroxide in 10 ml. of water. Reflux the solution for three hours, concentrate in vacuo and dissolve the residue in water. Acidify the aqueous solution to yield the desired 2-(2'-methyl-3'-trifluoromethylanilino) nicotinic acid, m.p. 226°-228° C. after recrystallization from acetone-hexane. By following the teachings of the foregoing examples as well as by the teachings of the above cited reference, there may also be produced the following nicotinic acids:

References: [1]Patent: US4205073,1980,A .

33
[ 54396-44-0 ]
[ 29241-65-4 ]
[ 108-95-2 ]
5-bromo-2-(2-methyl-3-trifluoromethylanilino)-nicotinic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydrogencarbonate; In methanol; sodium hydroxide;	EXAMPLE 2 5-Bromo-2-(2-methyl-3-trifluoromethylanilino) nicotinic acid Heat in an oil bath at 170° C. a mixture of 15 g. of 5-bromo-2-chloro-nicotinic acid, 12.2 g. of <strong>[54396-44-0]2-methyl-3-trifluoromethyl aniline</strong> and 60 g. of phenol for three hours. Treat the resulting reaction mixture with ether and 5percent sodium bicarbonate solution, concentrate and steam distil to obtain an oily residue. Dissolve the oily residue in dilute sodium hydroxide solution, acidify with dilute hydrochloric acid and filter. Recrystallize the product from methanol to yield 5-bromo-2-(2-methyl-3-trifluoromethylanilino) nicotinic acid, m.p. 222°-224° C.

References: [1]Patent: US4205073,1980,A .

34
[ 321-14-2 ]
[ 54396-44-0 ]
5-chloro-2-hydroxy-N-[2-methyl-3-(trifluoromethyl)phenyl]benzamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
14.5%		Example 118 5-Chloro-2-hydroxy-N-[2-methyl-3-(trifluoromethyl)phenyl]benzamide (Comopund No. 118). Using 5-chlorosalicylic acid and <strong>[54396-44-0]2-methyl-3-(trifluoromethyl)aniline</strong> as the raw materials, the same operation as the example 16 gave the title compound. Yield: 14.5percent. 1H-NMR(DMSO-d6): delta 2.36(3H, d, J=1.2Hz), 7.05(1H, d, J=8.7Hz), 7.46(1H, t, J=8.1Hz), 7.50(1H, dd, J=8.7, 2.7Hz), 7.60(1H, d, J=7.2Hz), 7.99(1H, d, J=7.2Hz), 8.00(1H, d, J=2.4Hz), 10.43(1H, s), 12.08(1H, s).
	With pyridine; phosphorus trichloride; In toluene; for 12h;Inert atmosphere; Reflux;	General procedure: The salicylic acid (1.2 equiv) was added to a mixture of toluene (0.3 M), aniline (1.0 equiv), phosphorus trichloride (1.1 equiv), and pyridine (0.05 equiv) in a Radley?s Carousel reaction tube (modified from Itai et al.20). The mixture was refluxed under nitrogen for 12 h then cooled to room temperature. Aqueous sodium bicarbonate was added dropwise to attain pH 6?7. The resultant mixture was extracted with EtOAc. The organic extracts were combined, dried (MgSO4), and concentrated under vacuum. After chromatography (1:10 EtOAc:Hex) compounds were recrystallized (EtOAc/Hex).

References: [1]Patent: EP1352650,2003,A1 .
[2]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 114 - 126.

35
[ 72763-19-0 ]
[ 54396-44-0 ]

Yield	Reaction Conditions	Operation in experiment
	nickel; In water; acetic acid;	C. 3-amino-2-methylbenzotrifluoride Add 70 ml of water, 150 ml of glacial acetic acid and 100 g. of 3-amino-4-chloro-2-methylthiomethylbenzotrifluoride to a three-necked round bottom flask fitted with mechanical stirrer and condenser. Then add 535 g. of washed and neutralized Raney active nickel catalyst (Grace no. 28 in water). Heat to reflux (98° C.-100° C.) for 20 hours. Steam distill to obtain the title compound.

References: [1]Patent: US4209464,1980,A .

Historical Records

Technical Information

• Alkyl Halide Occurrence • Buchwald-Hartwig C-N Bond and C-O Bond Formation Reactions • Chan-Lam Coupling Reaction • Hydride Reductions • Leuckart-Wallach Reaction • Mannich Reaction • Petasis Reaction • Preparation of Amines • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Specialized Acylation Reagents-Vilsmeier Reagent • Ugi Reaction

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
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

{[proInfo.proName]}

CAS No.: 54396-44-0

{[proInfo.proName]}

CAS No.: 54396-44-0

Alternative Products

Product Details of 2-Methyl-3-(trifluoromethyl)aniline

Safety of 2-Methyl-3-(trifluoromethyl)aniline

Application In Synthesis of 2-Methyl-3-(trifluoromethyl)aniline

[ 54396-44-0 ] Synthesis Path-Downstream 1~35

Related Products

Historical Records

Technical Information

Categories

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Molarity Calculator

Total Compounds Calculator

Dissolution Calculator