[ CAS No. 1547-87-1 ]

Name: 1547-87-1|2,2,2-Trifluoro-N,N-dimethylacetamide|98%
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Quality Control of [ 1547-87-1 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 1547-87-1 ]

Product Details of [ 1547-87-1 ]

CAS No. :	1547-87-1	MDL No. :	MFCD00043555
Formula :	C₄H₆F₃NO	Boiling Point :	133°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	141.09 g/mol	Pubchem ID :	-
Synonyms :

Safety of [ 1547-87-1 ]

Signal Word:	Danger	Class:	3
Precautionary Statements:	P210-P233-P240-P241+P242+P243-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313-P403+P235-P501	UN#:	1993
Hazard Statements:	H225-H315-H319	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 1547-87-1 ]

Upstream synthesis route of [ 1547-87-1 ]
Downstream synthetic route of [ 1547-87-1 ]

[ 1547-87-1 ] Synthesis Path-Upstream 1~8

1
[ 383-63-1 ]
[ 124-40-3 ]
[ 1547-87-1 ]

Reference： [1] Advanced Synthesis and Catalysis, 1997, vol. 339, # 8, p. 697 - 707
[2] Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258

2
[ 124-40-3 ]
[ 407-25-0 ]
[ 1547-87-1 ]

Reference： [1] Monatshefte fuer Chemie, 1966, vol. 97, p. 1541 - 1553
[2] Organic Magnetic Resonance, 1980, vol. 14, # 1, p. 40 - 44
[3] Journal of Physical Chemistry A, 1997, vol. 101, # 26, p. 4699 - 4706

3
[ 431-47-0 ]
[ 124-40-3 ]
[ 1547-87-1 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 2, 2000, # 10, p. 2054 - 2059

4
[ 354-32-5 ]
[ 124-40-3 ]
[ 1547-87-1 ]

Reference： [1] Doklady Chemistry, 1966, vol. 169, # 1, p. 677 - 680[2] Doklady Akademii Nauk SSSR, 1966, vol. 169, # 1, p. 128 - 131

5
[ 354-32-5 ]
[ 68-12-2 ]
[ 1547-87-1 ]

Reference： [1] Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation), 1966, p. 992 - 999[2] Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1966, p. 1038 - 1047

6
[ 75-90-1 ]
[ 124-40-3 ]
[ 1547-87-1 ]

Reference： [1] Journal of Physical Chemistry, 1983, vol. 87, # 1, p. 89 - 94

7
[ 56043-45-9 ]
[ 407-25-0 ]
[ 1547-87-1 ]

Reference： [1] Journal of Organic Chemistry, 1971, vol. 36, p. 2881 - 2885

8
[ 383-63-1 ]
[ 1608-26-0 ]
[ 1547-87-1 ]

Reference： [1] Tetrahedron Letters, 1964, p. 3139 - 3144

[ 1547-87-1 ] Synthesis Path-Downstream 1~5

1
[ 1547-87-1 ]
[ 819-06-7 ]

Yield	Reaction Conditions	Operation in experiment
62%	Stage #1: N,N-dimethyl-2,2,2-trifluoroacetamide With bis(cyclopentadienyl)dihydrozirconium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In tetrahydrofuran at 60℃; for 48h; Glovebox; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether; water for 2h; Glovebox; Inert atmosphere;	2. Experimental General procedure: In a nitrogen-filled glovebox, to a 15 mL reaction tube equipped with a magnetic stirrer, were added Cp2ZrH2 (0.01mmol, 2.2 mg) as the catalyst, and the appropriate amide (0.2mmol); solvent was added when necessary. HBpin (3 equiv. peramide functional group) was then added, and the reaction tube was taken out from the glovebox and stirred at room temperature for 12-48 h. The resultant crude amines were either isolated using silica gel flash chromatography, or acidified by stirring with HCl in Et2O (2 mL, 1N) for 2 h, after which time precipitation was observed. Then, the reaction solution was transferred to a centrifuge tube and centrifuged three times. The supernatant was removed and the resulting solid was dried inan oven at 80 °C for several hours to obtain the HCl salt of the amine.
	With lithium aluminium tetrahydride; diethyl ether
	With sodium borate; 1,2-dimethoxyethane; aluminium trichloride

	With sodium borate; 1,2-dimethoxyethane; boron fluoride ether
	With dimethylbis(η5-pentamethylcyclopentadienyl)thorium; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In benzene-d6 at 70℃; Inert atmosphere; Sealed tube; chemoselective reaction;

Reference： [1]Han, Bo; Jiao, Haijun; Wu, Lipeng; Zhang, Jiong [Cuihua Xuebao/Chinese Journal of Catalysis, 2021, vol. 42, # 11, p. 2059 - 2067]
[2]Bissell; Finger [Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258]
[3]Bissell; Finger [Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258]
[4]Bissell; Finger [Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258]
[5]Eisen, Moris S.; Saha, Sayantani [Dalton Transactions, 2020, vol. 49, # 36, p. 12835 - 12841]

2
[ 60-29-7 ]
[ 1547-87-1 ]
[ 819-06-7 ]

Reference： [1]Bissell; Finger [Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258]

3
[ 1547-87-1 ]
[ 819-06-7 ]

Reference： [1]Bissell; Finger [Journal of Organic Chemistry, 1959, vol. 24, p. 1256,1258]

4
[ 17347-32-9 ]
[ 1547-87-1 ]
[ 1426082-46-3 ]

Yield	Reaction Conditions	Operation in experiment
73%		5-Bromobenzo[b]thiophene (700 mg; 3.3 mmol) was dissolved in dry Et2O (14 mL) and placed under nitrogen flow. 1.6 M nBuLi in hexanes (2.25 mL, 3.6 mmol) was added dropwise, and the mixture was stirred at rt for 5 min. The reaction was cooled to -70 C and N,N-dimethyl-trifluoroacetamide (0.42 mL; 3.6 mmol) was added dropwise. The mixture was stirred at -70 C for 2 h, then allowed to warm up to rt, acidified with 1 M HCl to pH = 1, extracted with MTBE (3 × 50 mL), dried (MgSO4) and the solvent removed in vacuo. The residue was purified by chromatography using 5% EtOAc in heptane to afford the desired material as a yellow solid. Yield: 717 mg (73%). 1H NMR (CDCl3), delta: 7.68 (d, J = 1.83 Hz, 1H, ArH), 7.79 (s, 1H, ArH), 8.15 (d, J = 1.83 Hz, 2H, ArH).

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1284 - 1304

5
[ 1547-87-1 ]
[ 1097629-78-1 ]
tert-butyl (4-methyl-2-(2,2,2-trifluoroacetyl)thiophen-3-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
48%	Stage #1: tert‐butyl N‐(4‐methylthiophen‐3‐yl)carbamate With n-butyllithium In tetrahydrofuran; hexane at 25 - 30℃; for 1h; Stage #2: N,N-dimethyl-2,2,2-trifluoroacetamide In tetrahydrofuran at -20 - 20℃;	186.1 Step 1: tert-Butyl (4-methyl-2-(2,2,2-trifluoroacetyl)thiophen-3-yl)carbamate To a stirred and cooled (˜25 to ˜30° C.) solution of tert-butyl (4-methylthiophen-3-yl)carbamate (5.63 g, 26.4 mmol) in tetrahydrofuran (100 mL) was added, dropwise over 15 minutes, a 2.5 M solution of n-butyllithium in hexanes (25.0 mL, 62.5 mmol). Following the addition, the mixture was stirred for another one hour at -20° C. before cooling to -25 to -30° C. and adding a solution of 2,2,2-trifluoro-N,N-dimethylacetamide (6.4 mL, 55 mmol) in tetrahydrofuran (12 mL), dropwise over 20 minutes. The reaction was then allowed to slowly warm to room temperature and stirred overnight. To quench any remaining n-butyllithium, ethyl acetate (10 mL) was slowly added to the stirred solution. The mixture was then partitioned between ethyl acetate (˜100 mL) and an aqueous ammonium chloride solution (˜150 mL). The organic layer was washed with brine (2*˜150 mL), dried (Na2SO4) and concentrated onto ˜25 g of silica. The impregnated media was subjected to automated flash chromatography (Combiflash system; 0 to 10% ethyl acetate in heptane; 220 g silica column). The purified title compound (Rf˜0.42 with 9:1 heptane/ethyl acetate as the eluant) was obtained as a pale amber solid (3.89 g, 48%). 1H NMR (400 MHz, CDCl3) δ 8.87 (br s, 1H), 7.46 (s, 1H), 2.27 (d, J=0.7 Hz, 3H), 1.52 (s, 9H) ppm.

Reference： [1]Current Patent Assignee: SANOFI - US2020/102324, 2020, A1 Location in patent: Paragraph 1454; 1455

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[ 1547-87-1 ]

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
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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.
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H260	In contact with water releases flammable gases which may ignite spontaneously
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H316	Causes mild skin irritation
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H373	May cause damage to organs through prolonged or repeated exposure
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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

[ CAS No. 1547-87-1 ]

Quality Control of [ 1547-87-1 ]

Related Doc. of [ 1547-87-1 ]

Product Details of [ 1547-87-1 ]

Safety of [ 1547-87-1 ]

Application In Synthesis of [ 1547-87-1 ]

[ 1547-87-1 ] Synthesis Path-Upstream 1~8

[ 1547-87-1 ] Synthesis Path-Downstream 1~5

Related Functional Groups of [ 1547-87-1 ]

Trifluoromethyls

Fluorinated Building Blocks

Amines

Aliphatic Chain Hydrocarbons

Amides

Fluorination Reagents

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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Related Functional Groups of
[ 1547-87-1 ]