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406-87-1

Basic Information
CAS No.: 406-87-1
Name: 4,4,4-TRIFLUOROBUTYRALDEHYDE
Article Data: 24
Molecular Structure:
Molecular Structure of 406-87-1 (4,4,4-TRIFLUOROBUTYRALDEHYDE)
Formula: C4H5F3O
Molecular Weight: 126.078
Synonyms: 3-(Trifluoromethyl)propanal;4,4,4-Trifluorobutanal;Butyraldehyde,4,4,4-trifluoro- (8CI);
Density: 1.164 g/cm3
Boiling Point: 60.3 °C at 760 mmHg
Flash Point: -3.606 °C
Hazard Symbols: FlammableF, IrritantXi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 17.07000
LogP: 1.52780
Synthetic route
677-21-4

1,1,1-trifluoropropylene

201230-82-2

carbon monoxide

A

406-87-1

4,4,4-trifluorobutanal

B

58928-28-2

3,3,3-trifluoro-2-methylpropionaldehyde

Conditions
ConditionsYield
With hydrogen; carbonylhydridetris(triphenylphosphine)rhodium(I) In toluene at 80℃; for 15h; in an autoclave;A 2.6%
B 90%
Stage #1: carbon monoxide With hydroxo(1,5-cyclooctadiene)rhodium (I) dimer; hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; under 190.013 - 570.038 Torr; for 1h;
Stage #2: 1,1,1-trifluoropropylene In N,N-dimethyl-formamide at 80℃; for 15h; Solvent; Reagent/catalyst; Pressure; Temperature;
A 89%
B 1.2%
With hydrogen; dicobalt octacarbonyl 1.) toluene, room temperature, 130 atm, 2.) 100 deg C, 20 h; Yield given. Multistep reaction. Yields of byproduct given;
677-21-4

1,1,1-trifluoropropylene

201230-82-2

carbon monoxide

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
Stage #1: carbon monoxide With hydroxo(1,5-cyclooctadiene)rhodium (I) dimer; hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 100℃; under 380.026 Torr; for 1h;
Stage #2: 1,1,1-trifluoropropylene In N,N-dimethyl-formamide at 100℃; under 190.013 - 570.038 Torr; for 18h;
92%
With dichloro( 1,5-cyclooctadiene)platinum(ll); hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tin(ll) chloride In toluene at 80℃; under 72007.2 Torr; for 48h; Inert atmosphere; Autoclave; Schlenk technique; regioselective reaction;
460-32-2

3-bromo-1,1,1-trifluoropropane

68-12-2, 33513-42-7

N,N-dimethyl-formamide

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
With lithium In 2-methyltetrahydrofuran at -15 - -10℃; for 1h; Inert atmosphere;84.8%
Stage #1: 3-bromo-1,1,1-trifluoropropane With iodine; magnesium In 2-methyltetrahydrofuran at 45 - 68℃; for 3h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In 2-methyltetrahydrofuran at -25 - -20℃; for 1h; Temperature; Solvent; Inert atmosphere;
71.4%
461-18-7

4,4,4-trifluorobutanol

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
With pyridinium chlorochromate In dichloromethane for 2h; Ambient temperature;15%
With potassium dichromate; sulfuric acid
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at -8 - 0℃; pH=8.5;
460-37-7

1,1,1-trifluoro-3-iodopropane

68-12-2, 33513-42-7

N,N-dimethyl-formamide

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
Stage #1: 1,1,1-trifluoro-3-iodopropane With magnesium In tetrahydrofuran at 35 - 65℃; for 2h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In 2-methyltetrahydrofuran at -25 - -20℃; for 1h; Inert atmosphere;
78%
460-35-5

3-chloro-1,1,1-trifluoropropane

68-12-2, 33513-42-7

N,N-dimethyl-formamide

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
Stage #1: 3-chloro-1,1,1-trifluoropropane With magnesium In tetrahydrofuran; ethylene dibromide at 50 - 65℃; for 3h; Inert atmosphere;
Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -20 - -15℃; for 1h; Inert atmosphere;
70.8%
677-21-4

1,1,1-trifluoropropylene

201230-82-2

carbon monoxide

A

406-87-1

4,4,4-trifluorobutanal

B

421-07-8

1,1,1-trifluoropropane

C

58928-28-2

3,3,3-trifluoro-2-methylpropionaldehyde

Conditions
ConditionsYield
With hydrogen; hexarhodium hexadecacarbonyl; triphenylphosphine In toluene at 110℃; under 83600.1 Torr; for 22h; Product distribution; other platinum, cobalt, ruthenium catalyst;
With hydrogen; hexarhodium hexadecacarbonyl; triphenylphosphine 1.) toluene, room temperature, 110 atm, 2.) 80 deg C, 22 h; Yield given. Multistep reaction. Yields of byproduct given;
With hydrogen; dodecacarbonyl-triangulo-triruthenium In toluene at 100℃; for 16h; Product distribution; Mechanism; in an autoclave; hydrofomylation with other ruthenium, rhodium, cobalt, and platinum catalysts; effect of reaction temperature and CO pressure; investigation of various (perfluoroalkyl)ethenes;A n/a
B 38 % Chromat.
C n/a
Stage #1: carbon monoxide With [Rh(OH)(cod)]2; hydrogen; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In N,N-dimethyl-formamide at 80℃; under 760.051 Torr; for 1h;
Stage #2: 1,1,1-trifluoropropylene In N,N-dimethyl-formamide at 80℃; for 15h; Solvent; Temperature; Time; Concentration;
371-26-6

ethyl 4,4,4-trifluorobutanoate

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
With hydrogenchloride In dichloromethane
677-21-4

1,1,1-trifluoropropylene

201230-82-2

carbon monoxide

A

406-87-1

4,4,4-trifluorobutanal

B

(R)-trifluoromethylpropanal

C

(S)-2-trifluoromethylpropanal

Conditions
ConditionsYield
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 35℃; under 76000 Torr; for 42h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With acetylacetonatodicarbonylrhodium(l); hydrogen; (R,S)-binaphos In benzene at 35℃; under 76000 Torr; for 46h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
With polymer-supported (R,S)-BINAPHOS-Rh(acac); hydrogen In benzene at 60℃; under 7600 Torr; Product distribution; Further Variations:; Reagents; Hydroformylation;
With hydrogen In benzene at 40℃; under 60800 Torr; for 18h; Hydroformylation;
With hydrogen; Rh(I)-(R,S)-BINAPHOS under 38000 Torr; for 0.5h; Title compound not separated from byproducts;
79-37-8

oxalyl dichloride

461-18-7

4,4,4-trifluorobutanol

406-87-1

4,4,4-trifluorobutanal

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide
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Specification

The CAS register number of Butanal,4,4,4-trifluoro- is 406-87-1. It also can be called as 4,4,4-Trifluorocrotononitrile and the systematic name about this chemical is 4,4,4-trifluorobutanal. The molecular formula about this chemical is C4H5F3O and the molecular weight is 126.08.

Physical properties about Butanal,4,4,4-trifluoro- are: (1)ACD/LogP: 1.03; (2)ACD/LogD (pH 5.5): 1.02; (3)ACD/LogD (pH 7.4): 1.02; (4)ACD/BCF (pH 5.5): 3.54; (5)ACD/BCF (pH 7.4): 3.54; (6)ACD/KOC (pH 5.5): 86.02; (7)ACD/KOC (pH 7.4): 86.02; (8)#H bond acceptors: 1; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 17.07Å2; (11)Index of Refraction: 1.315; (12)Molar Refractivity: 21.22 cm3; (13)Molar Volume: 108.2 cm3; (14)Polarizability: 8.41x10-24cm3; (15)Surface Tension: 18.2 dyne/cm; (16)Enthalpy of Vaporization: 30.28 kJ/mol; (17)Boiling Point: 60.3 °C at 760 mmHg; (18)Vapour Pressure: 194 mmHg at 25°C.

Preparation: this chemical can be prepared by ethoxyethene and 2-(2,2,2-trifluoro-ethylazo)-prop-2-yl hydroperoxide. The reaction temperature is 50 ℃. The yield is about 70%.

Uses of Butanal,4,4,4-trifluoro-: it can be used to produce 1-Pyrrolidyl-4,4,4-trifluoro-1-butene with pyrrolidine at ambient temperature. This reaction will need reagent K2CO3. The yield is about 65%.

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)CCC=O
(2)InChI: InChI=1/C4H5F3O/c5-4(6,7)2-1-3-8/h3H,1-2H2
(3)InChIKey: SCJCDNUXDWFVFI-UHFFFAOYAP
(4)Std. InChI: InChI=1S/C4H5F3O/c5-4(6,7)2-1-3-8/h3H,1-2H2
(5)Std. InChIKey: SCJCDNUXDWFVFI-UHFFFAOYSA-N