[ CAS No. 141860-78-8 ] {[proInfo.proName]}

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Quality Control of [ 141860-78-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 141860-78-8 ]

Product Details of [ 141860-78-8 ]

CAS No. :	141860-78-8	MDL No. :	N/A
Formula :	C₆H₈F₃NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	183.13	Pubchem ID :	-
Synonyms :

Safety of [ 141860-78-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 141860-78-8 ]

* 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 [ 141860-78-8 ]
Downstream synthetic route of [ 141860-78-8 ]

[ 141860-78-8 ] Synthesis Path-Upstream 1~5

1
[ 72850-53-4 ]
[ 141860-78-8 ]
[ 2757-23-5 ]
[ 72850-52-3 ]

Reference： [1] Patent: US4251261, 1981, A,
[2] Patent: US4437875, 1984, A,
[3] Patent: US4437876, 1984, A,
[4] Patent: US4199506, 1980, A,

2
[ 141860-78-8 ]
[ 60-34-4 ]
[ 119022-51-4 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1993, vol. 30, # 1, p. 49 - 54
[2] Patent: US4855442, 1989, A,

3
[ 141860-78-8 ]
[ 65573-12-8 ]
[ 344-72-9 ]

Reference： [1] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442

4
[ 141860-78-8 ]
[ 65573-12-8 ]
[ 344-72-9 ]

Reference： [1] Tetrahedron Letters, 1999, vol. 40, # 35, p. 6439 - 6442

5
[ 141860-78-8 ]
[ 107-02-8 ]
[ 208517-35-5 ]

Reference： [1] Synthesis, 2005, # 16, p. 2751 - 2757

[ 141860-78-8 ] Synthesis Path-Downstream 1~10

1
[ 33842-02-3 ]
[ 141860-78-8 ]
[ 141860-79-9 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1992,vol. 101,p. 313 - 322
[2]Bulletin des Societes Chimiques Belges,1992,vol. 101,p. 313 - 322

2
[ 141860-78-8 ]
[ 60-34-4 ]
[ 119022-51-4 ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydrogencarbonate;	EXAMPLE 6 STR9 5-Trifluoromethyl-3-hydroxy-1-methylpyrazole 1.15 g (0.062 mol) of 3-amino-4,4,4-trifluoro-2-butenoic acid ethyl ester was cooled in an ice bath to form a solid. The ethyl ester was liquified upon the addition of 1.5 ml (0.038 mol) of methylhydrazine. The temperature was raised to 60 C. and the mixture was stirred for 6.5 hours. An N.M.R. spectrum of the crude mixture showed about 80% of the 3-hydroxy isomer and 10% of the 5-hydroxy isomer. The mixture was then evaporated on a rotary evaporator and stirred in saturated sodium bicarbonate solution, filtered, washed and dried to yield 2.1 g of a solid, m.p. 130-131 C.

Reference： [1]Journal of Heterocyclic Chemistry,1993,vol. 30,p. 49 - 54
[2]Patent: US4855442,1989,A

3
[ 2687-91-4 ]
[ 141860-78-8 ]
(Z)-3-[1-Ethyl-pyrrolidin-(2E)-ylideneamino]-4,4,4-trifluoro-but-2-enoic acid ethyl ester [ No CAS ]

Reference： [1]Bulletin de la Societe Chimique de France,1997,vol. 134,p. 47 - 58

4
[ 2556-73-2 ]
[ 141860-78-8 ]
(Z)-4,4,4-Trifluoro-3-[1-methyl-azepan-(2E)-ylideneamino]-but-2-enoic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79%	With phosgene In chloroform Heating;

Reference： [1]Bouillon, Jean-Philippe; Maliverney, Christian; Janousek, Zdenek; Viehe, Heinz G. [Bulletin de la Societe Chimique de France, 1997, vol. 134, # 1, p. 47 - 58]

5
[ 141860-78-8 ]
[ 65573-12-8 ]
[ 344-72-9 ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 6439 - 6442

6
[ 141860-78-8 ]
[ 65573-12-8 ]
[ 344-72-9 ]
(E)-3-Amino-4,4,4-trifluoro-2-thiocyanato-but-2-enoic acid ethyl ester [ No CAS ]
bis(2-amino-1-ethoxycarbonyl-3,3,3-(trifluoro)propenyl) disulfide [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 6439 - 6442

7
[ 141860-78-8 ]
[ 22134-07-2 ]
2-thioxo-3-(2,4,6-trichloro-phenyl)-6-trifluoromethyl-2,3-dihydro-1<i>H</i>-pyrimidin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride In N,N-dimethyl-formamide at 20 - 80℃; for 3h;

Reference： [1]Yagi, Kazuo; Akimoto, Kazuhiko; Mimori, Norihiko; Miyake, Toshiro; Kudo, Masaki; Arai, Kazutaka; Ishii, Shigeru [Pest Management Science, 2000, vol. 56, # 1, p. 65 - 73]

8
[ 35573-36-5 ]
[ 141860-78-8 ]
3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.3%	With hydrogenchloride; In N,N-dimethyl-formamide; mineral oil;	Step B Synthesis of 6-trifluoromethyl-3-(4-methoxyphenylmethyl)-2,4(1H,3H)-pyrimidinedione as an Intermediate Sodium hydride (60% in mineral oil), 0.88 gram (0.02 mole), was washed with two 10 mL portions of heptane, then stirred with 50 mL of N,N-dimethylformamide. The mixture was cooled to 0-5 C., and a solution of 3.7 grams (0.02 mole) of ethyl 3-amino-4,4,4-trifluoro-2-butenoate in 10 mL of N,N-dimethylformamide was added dropwise. Upon cessation of the evolution of hydrogen gas a solution of 4.2 grams (0.02 mole) of ethyl (4-methoxy-phenylmethyl)carbamate in 10 mL of N,N-dimethylformamide was added, and the reaction mixture was heated to 90 C., where it stirred for about one hour. After this time the reaction mixture was cooled and poured into 500 mL of ice and aqueous 10% hydrochloric acid. The resultant solid was collected by filtration and dried, yielding 4.1 grams (68.3% yield) of 6-trifluoro-methyl-3-(4-methoxyphenylmethyl)-2,4(1H,3H)-pyrimidinedione; mp 203-204 C. The NMR spectrum was consistent with the proposed structure.

Reference： [1]Patent: US5780630,1998,A

9
[ 72850-53-4 ]
[ 141860-78-8 ]
[ 2757-23-5 ]
[ 72850-52-3 ]

Yield	Reaction Conditions	Operation in experiment
	With trichlorophosphate; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chlorobenzene; Petroleum ether;	EXAMPLE 6 Preparation of Ethyl 2-Chloro-4-Trifluoromethyl-5-Thiazolecarboxylate. A mixture of 13.0 g (0.0992 mole) of chlorocarbonylsulfenyl chloride, 17 g (0.0928 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate and 50 ml. of chlorobenzene was heated at 135 C. for 2 hours, cooled and triturated with 200 ml. of petroleum ether. The light yellow precipitate was recrystallized from hexane-ether to give 12.2 g (55%) of white prisms, m.p. 121-123 C., which was identified as ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolecarboxylate. A mixture of 10 g (0.0415 mole) of ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolecarboxylate, 30 ml. of POCl3 and 1 ml. of dimethylformamide was held at reflux for 87 hours. The reaction mixture was poured into 500 ml. of ice water and extracted three times with 60 ml. of ether. The ether solution was washed with saturated sodium chloride solution, dried (MgSO4) and concentrated under reduced pressure to give 10.2 g of light yellow solid, m.p. 57-60 C., which was recrystallized from hexane to give 9.95 g (92.4%) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate as light yellow solid, m.p. 58-59 C. Anal. Calc'd for C7 H5 F3 ClNO2 S: C, 32.38; H, 1.94; N, 5.40. Found: C, 32.33; H, 1.98; N, 5.35.
	With trichlorophosphate; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chlorobenzene; Petroleum ether;	EXAMPLE 17 Preparation of Ethyl 2-Chloro-4-Trifluoromethyl-5-Thiazolecarboxylate A mixture of 13.0 g (0.0992 mole) of chlorocarbonylsulfenyl chloride, 17 g (0.0928 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate and 50 ml. of chlorobenzene was heated at 135 C. for 2 hours, cooled and triturated with 200 ml. of petroleum ether. The light yellow precipitate was recrystallized from hexane-ether to give 12.2 g (55%) of white prisms, m.p. 121-123 C., which was identified as ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolecarboxylate. A mixture of 10 g (0.0415 mole) of ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolecarboxylate, 30 ml. of POCl3 and 1 ml. of dimethylformamide was held at reflux for 87 hours. The reaction mixture was poured into 500 ml. of ice water and extracted three times with 60 ml. of ether. The ether solution was washed with saturated sodium chloride solution, dried (MgSO4) and concentrated under reduced pressure to give 10.2 g of light yellow solid, m.p. 57-60 C., which was recrystallized from hexane to give 9.95 g (92.4%) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate as light yellow solid, m.p. 58-59 C. Anal. Calc'd. for C7 H5 F3 ClNO2 S: C, 32.38; H, 1.94; N, 5.40. Found: C, 32.33; H, 1.98; N, 5.35.
	With trichlorophosphate; In N-methyl-acetamide; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chlorobenzene; Petroleum ether;	EXAMPLE 11 Preparation of Ethyl 2-Chloro-4-Trifluoromethyl-5-Thiazolecarboxylate. A mixture of 13.0 g (0.0992 mole) of chlorocarbonylsulfenyl chloride, 17 g (0.0928 mole) of ethyl 3-amino-4,4,4-trifluorocrotonate and 50 ml. of chlorobenzene was heated at 135 C. for 2 hours, cooled and triturated with 200 ml. of petroleum ether. The light yellow precipitate was recrystallized from hexane-ether to give 12.2 g (55%) of white prisms, m.p. 121-123 C., which was identified as ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolecarboxylate. A mixture of 10 g (0.0415 mole) of ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazolecarboxylate, 30 ml. of POCl3 and 1 ml. of dimethylformamide was held at reflux for 87 hours. The reaction mixture was poured into 500 ml. of ice water and extracted three times with 60 ml. of ether. The ether solution was washed with saturated sodium chloride solution, dried (MgSO4) and concentrated under reduced pressure to give 10.2 g of light yellow solid, m.p. 57-60 C., which was recrystallized from hexane to give 9.95 g (92.4%) of ethyl 2-chloro-4-trifluoromethyl-5-thiazolecarboxylate as light yellow solid, m.p. 58-59 C. Anal. Calc'd. for C7 H5 F3 ClNO2 S: C, 32.38; H, 1.94; N, 5.40. Found: C, 32.33; H, 1.98; N, 5.35.

Reference： [1]Patent: US4251261,1981,A
[2]Patent: US4437875,1984,A
[3]Patent: US4199506,1980,A

10
[ 141860-78-8 ]
[ 56651-60-6 ]
3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)-1H-pyrimidine-2,4-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: ethyl 3-amino-4,4,4-trifluorocrotonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 4-methoxybenzyl isocyanate In N,N-dimethyl-formamide at 0 - 25℃; for 14h;	C-1.2 Step 2: To a solution of ethyl (Z)-3-amino-4,4,4-trifluoro-but-2-enoate (19 g) in DMF (500 mL) was added NaH (6 g) in portions at 0°C. The reaction mixture was then stirred at 0°C for 1 h. The mixture was then added to 1-(isocyanatomethyl)-4-methoxy-benzene (17 g) at 0°C. The resulting mixture was stirred at 0°C to 25°C for 14 h. The solvent was removed under reduced pressure and water (1 L) was added, and the organic layer was separated. The aqueous layer was extracted with EtOAc (3 x 500 mL). The organic layers were combined, washed with brine (500 mL), dried over Na2S04, filtered, and concentrated to afford crude 3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)- 1 H-pyrimidine-2,4-dione (15 g) as yellow oil. 1H NMR (MeOD, 400 MHz) δ 7.27 (d, J=8.8 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 5.80 (s, 1 H), 5.02 (s, 2H) 3.70 (s, 3H).
	Stage #1: ethyl 3-amino-4,4,4-trifluorocrotonate With sodium hydride In N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: 4-methoxybenzyl isocyanate In N,N-dimethyl-formamide at 0 - 25℃; for 14h;	2.a.2 Step 2: To a solution of ethyl (Z)-3-amino-4,4,4-trifluoro-but-2-enoate (19 g) in DMF (500 mL) was added NaH (6 g) in portions at 0°C. The reaction mixture was then stirred at 0°C for 1 h. The mix- ture was then added to 1-(isocyanatomethyl)-4-methoxy-benzene (17 g) at 0°C. The resulting mix- ture was stirred at 0°C to 25°C for 14 h. The solvent was removed under reduced pressure and wa- ter (1 L) was added, and the organic layer was separated. The aqueous layer was extracted with EtOAc (3 × 500 mL). The organic layers were combined, washed with brine (500 mL), dried over Na2SO4, filtered, and concentrated to afford crude 3-[(4-methoxyphenyl)methyl]-6-(trifluoromethyl)- 1H-pyrimidine-2,4-dione (15 g) as yellow oil.1H NMR (MeOD, 400 MHz) δ 7.27 (d, J=8.8 Hz, 2H), 6.77 (d, J=8.4 Hz, 2H), 5.80 (s, 1H), 5.02 (s, 2H) 3.70 (s, 3H).

Reference： [1]Current Patent Assignee: BASF SE - WO2017/167832, 2017, A1 Location in patent: Page/Page column 67
[2]Current Patent Assignee: BASF SE - WO2018/206479, 2018, A1 Location in patent: Page/Page column 65

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H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 141860-78-8 ] {[proInfo.proName]}

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[ 141860-78-8 ] Synthesis Path-Upstream 1~5

[ 141860-78-8 ] Synthesis Path-Downstream 1~10

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