180635-74-9

Basic information

• Product Name: 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL
• Synonyms: 4-(Trifluoromethyl)benzenepropanol;Benzenepropanol,4-(trifluoroMethyl)-;3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL;3-[4-(trifluoroMethyl)phenyl]propanol;4-(3-Hydroxyprop-1-yl)benzotrifluoride;3-(4-Trifluoromethylphenyl)-1-propanol
• CAS NO: 180635-74-9
• Molecular Formula: C₁₀H₁₁F₃O
• Molecular Weight: 204.1889496
• Mol File: 180635-74-9.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 246.6°C at 760 mmHg
• Flash Point: 108.1°C
• Appearance: /
• Density: 1.202g/cm³
• Vapor Pressure: 0.0143mmHg at 25°C
• Refractive Index: 1.465
• CAS DataBase Reference: 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL(180635-74-9)
• EPA Substance Registry System: 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL(180635-74-9)

Safety Data

• Hazardous Substances Data: 180635-74-9(Hazardous Substances Data)

Usage

Description

3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL, also known as 4-(Trifluoromethyl)benzenepropanol, is an organic compound characterized by its trifluoromethylphenyl group attached to a propane unit with a hydroxyl group. This molecule is known for its unique structural features and reactivity, making it a versatile building block in organic synthesis.

Uses

Used in Pharmaceutical Industry:
3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL is used as a key intermediate in the asymmetric synthesis of tetrahydroisoquinolines through enzymic Pictet-Spengler reactions. This application is significant because tetrahydroisoquinolines are important structural motifs found in various bioactive compounds, including pharmaceuticals with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, 3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL serves as a valuable precursor for the creation of a wide range of complex organic molecules. Its unique structure allows for selective functionalization and modification, making it a useful building block for the development of new compounds with diverse applications.
Used in Enzyme Catalysis:
3-(4-TRIFLUOROMETHYL-PHENYL)-PROPAN-1-OL is also utilized in the study and application of enzyme-catalyzed reactions, particularly in the context of asymmetric synthesis. The use of enzymes allows for the selective formation of desired products with high enantiomeric purity, which is crucial in the development of chiral drugs and other specialty chemicals.

InChI:InChI=1/C10H11F3O/c11-10(12,13)9-5-3-8(4-6-9)2-1-7-14/h3-6,14H,1-2,7H2

Synthetic route

3-(4-trifluoromethylphenyl)propionic acid (53473-36-2) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Stage #1: 3-(4-trifluoromethylphenyl)propionic acid With borane-THF In tetrahydrofuran at 0 - 20℃; for 15.3h; Stage #2: With methanol In tetrahydrofuran at 0℃;	100%
With borane-THF In tetrahydrofuran at 0 - 20℃; for 16h; Inert atmosphere;	100%
With sodium tetrahydroborate; iodine In tetrahydrofuran at 70℃; for 16h; Cooling with ice;	100%

3-(4-tert-butylphenyl)propionic acid (1208-64-6) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With sodium tetrahydroborate; iodine In tetrahydrofuran at 20 - 70℃; for 16.5h; Cooling with ice;	100%

4-Iodobenzotrifluoride (455-13-0) + allyl alcohol (107-18-6) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); tetramethylammonium formiate; triphenylphosphine In water; N,N-dimethyl-formamide at 80℃; for 4h; Heck Reaction; regioselective reaction;	67%

4-(trifluoromethyl)benzylic alcohol (349-95-1) + ethanol (64-17-5) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; potassium tert-butylate In tetrahydrofuran at 100℃; for 24h; Inert atmosphere;	37%

methyl 3-(4-(trifluoromethyl)phenyl)propanoate (849442-21-3) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;
With lithium aluminium tetrahydride In diethyl ether at 0℃;
With sodium tetrahydroborate In tetrahydrofuran; methanol Reflux;

4-Trifluoromethylbenzaldehyde (455-19-6) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrofuran / Heating 2: H2 / 10 percent Pd/C / tetrahydrofuran / 2068.59 Torr 3: LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

methyl (2E)-3-(4-(trifluoromethyl)phenyl)prop-2-enoate (20754-22-7) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2 / 10 percent Pd/C / tetrahydrofuran / 2068.59 Torr 2: LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

4-Iodobenzotrifluoride (455-13-0) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium diacetate; lithium chloride; tetrabutylammomium bromide; lithium acetate dihydrate / N,N-dimethyl-formamide / 48 h / 20 °C 2: sodium tetrahydroborate / methanol / 0.17 h / 20 °C View Scheme

3-(4-trifluoromethylphenyl)propanal (166947-09-7) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With sodium tetrahydroborate In methanol at 20℃; for 0.166667h;	253 mg

3-(4-trifluoromethylphenyl)prop-2-yn-1-ol (173546-21-9) → (Z)-3-(4-(trifluoromethyl)phenyl)-2-propene-1-ol (826994-11-0) + 3-(4-trifluoromethylphenyl)-2-propen-1-ol (125617-18-7) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With sodium tetrahydroborate; hydrogen; cobalt(II) diacetate tetrahydrate; ethylenediamine In tetrahydrofuran; ethanol; water at 20℃; under 2250.23 Torr; for 12h; Autoclave; Glovebox; diastereoselective reaction;	A n/a B n/a C n/a

4-Iodobenzotrifluoride (455-13-0) → (Z)-3-(4-(trifluoromethyl)phenyl)-2-propene-1-ol (826994-11-0) + 3-(4-trifluoromethylphenyl)-2-propen-1-ol (125617-18-7) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / acetonitrile / 12 h / 20 °C / Inert atmosphere; Schlenk technique 2: ethylenediamine; sodium tetrahydroborate; hydrogen; cobalt(II) diacetate tetrahydrate / tetrahydrofuran; water; ethanol / 12 h / 20 °C / 2250.23 Torr / Autoclave; Glovebox View Scheme

methyl (2E)-3-(4-(trifluoromethyl)phenyl)prop-2-enoate (20754-22-7) → 3-(4-trifluoromethylphenyl)-2-propen-1-ol (125617-18-7) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With [Ru(2-(methylthio)-N-[(pyridin-2-yl)methyl]ethan-1-amine)(triphenylphosphine)Cl2]; potassium tert-butylate; hydrogen In toluene at 40℃; under 22502.3 Torr; for 4h; Overall yield = 63 %; Overall yield = 1.27 g;

4-trifluoromethylphenylacetylene (705-31-7) → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: copper(l) chloride; bathophenanthroline / dimethyl sulfoxide / 12 h / 20 °C / 11251.1 Torr / Inert atmosphere; Autoclave 2: hydrogen / methanol / 18 h / 20 °C / 7500.75 Torr / Autoclave 3: hydrogen; molybdenum hexacarbonyl / 1-methyl-pyrrolidin-2-one / 14 h / 180 °C / 52505.3 Torr / Autoclave View Scheme

C10H5F3O2*C9H19N → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen / methanol / 18 h / 20 °C / 7500.75 Torr / Autoclave 2: hydrogen; molybdenum hexacarbonyl / 1-methyl-pyrrolidin-2-one / 14 h / 180 °C / 52505.3 Torr / Autoclave View Scheme

C10H9F3O2*C9H19N → 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9)

Conditions	Yield
With hydrogen; molybdenum hexacarbonyl In 1-methyl-pyrrolidin-2-one at 180℃; under 52505.3 Torr; for 14h; Autoclave;	280 mg

trifluoromethylsulfonic anhydride (358-23-6) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-(4-trifluoromethylphenyl)-1-propyl trifluoromethanesulfonate

Conditions	Yield
With 2,4-lutidine In dichloromethane at -78℃; for 0.5h; Inert atmosphere;	95%

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → (2E)-3-(4-trifluoromethylphenyl)prop-2-enal (95123-61-8)

Conditions	Yield
With (S)-diphenylprolinol; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide; acetonitrile at 20℃; for 6h; stereoselective reaction;	92%

[bromo(difluoro)methyl](trimethyl)silane (115262-01-6) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 1-(3-(difluoromethoxy)propyl)-4-(trifluoromethyl)benzene

Conditions	Yield
With potassium hydrogenfluoride In water at 20℃; for 12h;	90%

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-(4-trifluoromethylphenyl)propanal (166947-09-7)

Conditions	Yield
With pyridinium chlorochromate In dichloromethane at 0 - 20℃; for 3h;	86.5%
Stage #1: 3-(4-(trifluoromethyl)phenyl)propan-1-ol With oxalyl dichloride In dichloromethane at -78℃; for 1h; Stage #2: With triethylamine In dichloromethane at -78℃; for 2.5h;	79.31%
With pyridinium chlorochromate In dichloromethane at 20℃; for 4h;

benzoyl chloride (98-88-4) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-(4-trifluoromethylphenyl)propyl benzoate

Conditions	Yield
With pyridine In dichloromethane at 0 - 20℃; for 5h;	86%

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 1-(3-iodopropyl)-4-(trifluoromethyl)benzene

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; for 1h; Appel Halogenation; Sealed tube;	82%

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-(4-trifluoromethylphenyl)propan-1-ol sulfamate ester (1042906-15-9)

Conditions	Yield
With formic acid; isocyanate de chlorosulfonyle; triethylamine In dichloromethane at 0 - 25℃; Schlenk technique; Inert atmosphere;	66%
With pyridine; formic acid; isocyanate de chlorosulfonyle In dichloromethane	63%

1,2-bis(t-butyloxycarbonyl)hydrazine (16466-61-8) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → (S)-di-tert-butyl 1-(1-hydroxy-3-(4-(trifluoromethyl)phenyl)propan-2-yl)hydrazine-1,2-dicarboxylate

Conditions	Yield
Stage #1: 1,2-bis(t-butyloxycarbonyl)hydrazine; 3-(4-(trifluoromethyl)phenyl)propan-1-ol With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,6-dimethylpyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; copper(I) bromide In acetonitrile at 20℃; for 72h; Stage #2: In methanol; acetonitrile at 0℃; enantioselective reaction;	59%

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-(4-trifluoromethyl-phenyl)-propane-1-thiol

Conditions	Yield
Multi-step reaction with 3 steps 1: CBr4; Ph3P / CH2Cl2 / 24 h / 0 °C 2: ethanol / 24 h / Heating 3: NaOH / ethanol / 2 h / Heating View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 2-[3-(4-trifluoromethyl-phenyl)-propyl]-isothiourea; hydrobromide

Conditions	Yield
Multi-step reaction with 2 steps 1: CBr4; Ph3P / CH2Cl2 / 24 h / 0 °C 2: ethanol / 24 h / Heating View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-[4-(Trifluoromethyl)phenyl]propyl (2S)-1-(3,3-dimethyl-2-oxopentanoyl)-2-pyrrolidinecarbothioate

Conditions	Yield
Multi-step reaction with 4 steps 1: CBr4; Ph3P / CH2Cl2 / 24 h / 0 °C 2: ethanol / 24 h / Heating 3: NaOH / ethanol / 2 h / Heating 4: DCC; DMAP / CH2Cl2 / 24 h / 20 °C View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 2-{1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl}-N-methyl-2-phenyl-acetamide

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: acetic acid / ethanol / 0.1 h / 130 °C / 10501.1 Torr / microwave irradiation 3: N-ethyl-N,N-diisopropylamine / 3-methyl-2-butyl-ketone / 24 h / 90 °C / Inert atmosphere View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 1-ethyl-3-methyl-4-[2-(4-trifluoromethyl-phenyl)-ethyl]-4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridine (955403-67-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 4 h / 20 °C / Inert atmosphere 2: acetic acid / ethanol / 0.1 h / 130 °C / 10501.1 Torr / microwave irradiation View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → C18H18F3NO2

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; sodium bromide; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / ethyl acetate; water / 1.5 h / 0 °C 2: recombinant norcoclaurine synthase from Coptis japonica, first 29 amino acid residues removed / dimethyl sulfoxide / 0.25 h / 30 °C / pH 7 / Enzymatic reaction View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → (R)-3-(4-trifluoromethylbenzyl)-4-oxobutyronitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 0.25 h / 0 °C 2: (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one trifluoromethanesulfonate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 2,6-dimethylpyridine / dimethyl sulfoxide / 8 h / 23 °C / Inert atmosphere; Sealed tube; Irradiation View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-(4-trifluoromethylbenzyl)-4-oxobutyronitrile

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridinium chlorochromate / dichloromethane / 0.25 h / 0 °C 2: C9H18N2O*CHF3O3S; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 2,6-dimethylpyridine / dimethyl sulfoxide / 8 h / 23 °C / Inert atmosphere; Sealed tube; Irradiation View Scheme

3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → C12H12F3NO

Conditions

Yield

Multi-step reaction with 3 steps 1: pyridinium chlorochromate / dichloromethane / 0.25 h / 0 °C 2: (2R,5S)-2-tert-butyl-3,5-dimethylimidazolidin-4-one trifluoromethanesulfonate; tris(bipyridine)ruthenium(II) dichloride hexahydrate; 2,6-dimethylpyridine / dimethyl sulfoxide / 8 h / 23 °C / Inert atmosphere; Sealed tube; Irradiation 3: sodium tetrahydroborate / dichloromethane; methanol / 3 h / 0 °C View Scheme

benzoyl chloride (98-88-4) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → 3-oxo-3-(4-trifluoromethylphenyl)propyl benzoate

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / dichloromethane / 5 h / 0 - 20 °C 2: cobalt(II) acetate; manganese(III) triacetate dihydrate; oxygen; 4,5,6,7-tetrafluoro-2-hydroxy-3-(2,2,2-trifluoroethoxy)-3-trifluoromethylisoindolin-1-one / 2,2,2-trifluoroethanol / 48 h / 60 °C / 760.05 Torr View Scheme

1,2-bis(t-butyloxycarbonyl)hydrazine (16466-61-8) + 3-(4-(trifluoromethyl)phenyl)propan-1-ol (180635-74-9) → C27H32F3N3O8

Conditions	Yield
Multi-step reaction with 2 steps 1.1: copper(I) bromide; 2,6-dimethylpyridine; (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / acetonitrile / 72 h / 20 °C 1.2: 0 °C 2.1: pyridine / dichloromethane View Scheme

Upstream product

• 849442-21-3 methyl 3-(4-(trifluoromethyl)phenyl)propanoate 
• 173546-21-9 3-(4-trifluoromethylphenyl)prop-2-yn-1-ol 
• 455-13-0 4-Iodobenzotrifluoride 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 64-17-5 ethanol 
• 107-18-6 allyl alcohol 
• 705-31-7 4-trifluoromethylphenylacetylene 
• 20754-22-7 methyl (2E)-3-(4-(trifluoromethyl)phenyl)prop-2-enoate 
• 1208-64-6 3-(4-tert-butylphenyl)propionic acid 
• 166947-09-7 3-(4-trifluoromethylphenyl)propanal 
• 53473-36-2 3-(4-trifluoromethylphenyl)propionic acid 
• 455-19-6 4-Trifluoromethylbenzaldehyde 

Downstream Products

• 166947-09-7 3-(4-trifluoromethylphenyl)propanal 
• 528867-43-8 4-(4-(trifluoromethyl)phenyl)butanal 

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