585-50-2

Basic information

• Product Name: 3-(3-Trifluoromethylphenyl)propionic acid
• Synonyms: RARECHEM AL BO 1070;3-(3'-TRIFLUOROMETHYLPHENYL)-PROPIONIC ACID;3-(3-TRIFLUOROMETHYLPHENYL)PROPIONIC ACID;3-(3-(TRIFLUOROMETHYL)PHENYL)PROPANOIC ACID;3-Trifluoromethylbenzenepropanoic acid;3-(3-Trifluoromethylphenyl)propionic acid ,97%;3-(3-Carboxyprop-1-yl)benzotrifluoride;3-Benzotrifluoridepropanoic acid
• CAS NO: 585-50-2
• Molecular Formula: C₁₀H₉F₃O₂
• Molecular Weight: 218.17
• EINECS: 1308068-626-2
• Product Categories: Carboxylic Acids;Phenyls & Phenyl-Het;Carboxylic Acids;Phenyls & Phenyl-Het;Fluorine series;Cinacalcet Intermediate
• Mol File: 585-50-2.mol
• Article Data: 30

Chemical Properties

• Melting Point: 35°C(lit.)
• Boiling Point: 149°C/11mmHg(lit.)
• Flash Point: 116.3 °C
• Appearance: /
• Density: 1.307 g/cm³
• Vapor Pressure: 0.00375mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 4.56±0.10(Predicted)
• CAS DataBase Reference: 3-(3-Trifluoromethylphenyl)propionic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(3-Trifluoromethylphenyl)propionic acid(585-50-2)
• EPA Substance Registry System: 3-(3-Trifluoromethylphenyl)propionic acid(585-50-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 585-50-2(Hazardous Substances Data)

Usage

Chemical Properties

White Crysstalline

Uses

3-(3-Trifluoromethylphenyl)propionic Acid can be used as catalysts.

InChI:InChI=1/C10H9F3O2/c11-10(12,13)8-3-1-2-7(6-8)4-5-9(14)15/h1-3,6H,4-5H2,(H,14,15)

Synthetic route

3-(trifluoromethyl)cinnamic acid (779-89-5) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
With hydrogen; palladium dihydroxide at 40 - 60℃; under 2250.23 Torr;	100%
With palladium on activated charcoal; hydrogen; sodium carbonate In water at 25℃; under 1500.15 - 2250.23 Torr; for 3h;	99.4%
With hydrogen; palladium on activated charcoal In methanol at 20 - 25℃; under 30.003 Torr;	95.2%

3-(trifluoromethyl)cinnamic acid (779-89-5) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
With hydrogen; 5% Pd(II)/C(eggshell) In methanol at 25℃; under 735.572 Torr; for 10h;	100%
Stage #1: 3-(trifluoromethyl)cinnamic acid With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In water	97%
With palladium diacetate; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In dichloromethane at 25℃; for 12h; Sealed tube; Inert atmosphere; chemoselective reaction;	97%

3-(3-(trifluoromethyl)phenyl)propanenitrile (95096-06-3) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
With hydrogenchloride; water for 4.5h; Product distribution / selectivity;	94%
With sodium hydroxide; water In ethylene glycol at 125℃; for 9h; Product distribution / selectivity;

2-vinyl-1,3-dioxolane (3984-22-3) + 3-bromo-1-trifluoromethylbenzene (401-78-5) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Stage #1: 2-vinyl-1,3-dioxolane; 3-bromo-1-trifluoromethylbenzene With potassium carbonate; Pd-Tedicyp catalyst In N,N-dimethyl-formamide at 110℃; for 20h; Heck reaction; Stage #2: With sodium hydroxide; water In N,N-dimethyl-formamide at 50 - 80℃;	93%

(E)-2-Oxo-4-(3-trifluoromethyl-phenyl)-but-3-enoic acid → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) + (E)-3-(3-(trifluoromethyl)phenyl)acrylaldehyde (262268-58-6)

Conditions	Yield
With edetate disodium; thiamine diphosphate; sodium citrate; magnesium chloride In water; acetonitrile at 20℃; Rate constant; pH 6.0, brewers' yeast pyruvate decarboxylase (PDC, EC 4.1.1.1), also in the presence of pyruvamide;

3-<2-chloro-ethyl>-trifluoromethyl-benzene → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
With carbon dioxide; magnesium

m-trifluoromethyl-α-chlorohydrocinnamic acid → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Stage #1: m-trifluoromethyl-α-chlorohydrocinnamic acid With acetic acid; zinc In water at 20 - 35℃; for 1h; Stage #2: With hydrogenchloride In water at 20℃; Product distribution / selectivity;

methyl 3-(3-(trifluoromethyl)phenyl)propanoate (294856-02-3) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Stage #1: methyl 3-(3-(trifluoromethyl)phenyl)propanoate With sodium hydroxide; isopropyl alcohol at 20℃; for 6h; Stage #2: With hydrogenchloride; water
Stage #1: methyl 3-(3-(trifluoromethyl)phenyl)propanoate With lithium hydroxide monohydrate In tetrahydrofuran; water at 20℃; for 48h; Stage #2: With hydrogenchloride In tetrahydrofuran; diethyl ether; water
With water; sodium hydroxide In methanol at 20℃; for 4h;	3.9 g

3-Trifluoromethylbenzaldehyde (454-89-7) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: piperidine / pyridine / 50 - 75 °C / Inert atmosphere 1.2: 0 °C / Cooling with ice 2.1: hydrogen / palladium 10% on activated carbon / methanol / 2.5 h / 750.08 Torr View Scheme
Multi-step reaction with 2 steps 1.1: pyridine; piperidine / 4.25 h / 20 - 120 °C / Inert atmosphere 1.2: pH 2 2.1: sodium hydroxide / water / 20 °C 2.2: 7 h / 25 - 30 °C / 750.08 Torr 2.3: pH 2 View Scheme

3-bromo-1-trifluoromethylbenzene (401-78-5) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: palladium diacetate; potassium carbonate; triphenylphosphine / N,N-dimethyl-formamide / 15 h / 110 °C / Inert atmosphere 1.2: 15 h / 20 °C / 760.05 Torr 2.1: lithium hydroxide monohydrate / tetrahydrofuran; water / 48 h / 20 °C View Scheme

3-Trifluoromethylbenzyl chloride (705-29-3) → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 5 °C 1.2: 2 h 2.1: sodium chloride / water; N,N-dimethyl-formamide / 6 h / 150 °C 3.1: sodium hydroxide; water / methanol / 4 h / 20 °C View Scheme

dimethyl 2-(3-(trifluoromethyl)benzyl)malonate → 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium chloride / water; N,N-dimethyl-formamide / 6 h / 150 °C 2: sodium hydroxide; water / methanol / 4 h / 20 °C View Scheme

methanol (67-56-1) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → methyl 3-(3-(trifluoromethyl)phenyl)propanoate (294856-02-3)

Conditions	Yield
With sulfuric acid Reflux;	99%
With thionyl chloride for 4h; Inert atmosphere; Reflux;	97%
With sulfuric acid at 30 - 45℃;

2-Amino-5-(4-methyl-phenyl)-thiophene-3-carboxylic Acid Amide + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → C22H17F3N2OS (1393911-92-6)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In chloroform at 120℃; Microwave irradiation;	98%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) + (R)-<1-(1-Naphthyl)ethyl>ammonium chloride (82572-04-1) → (R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide (1005450-55-4)

Conditions	Yield
Stage #1: (R)-<1-(1-Naphthyl)ethyl>ammonium chloride With sodium hydroxide In toluene Stage #2: 3-(3-trifluoromethylphenyl)propanoic acid In toluene at 140 - 150℃; Further stages.;	95%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → 3-[3-(trifluoromethyl)phenyl]propan-1-ol (78573-45-2)

Conditions	Yield
Stage #1: 3-(3-trifluoromethylphenyl)propanoic acid With borane-THF In tetrahydrofuran at 0 - 20℃; for 25h; Stage #2: With water In tetrahydrofuran; methanol	94%
With borane In tetrahydrofuran at 0 - 20℃; for 25h; Inert atmosphere;	94%
Stage #1: 3-(3-trifluoromethylphenyl)propanoic acid With 4-methyl-morpholine; chloroformic acid ethyl ester In 2-methyltetrahydrofuran at -10 - -5℃; for 0.00166667h; Stage #2: With sodium tetrahydroborate In 2-methyltetrahydrofuran; water at 0 - 5℃; for 0.5h; Solvent; Reagent/catalyst;	92.2%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → 3-(trifluoromethyl)benzenepropanoic acid chloride (455-03-8)

Conditions	Yield
With thionyl chloride; N,N-dimethyl-formamide In Isopropyl acetate at 43℃; Temperature;	93%
With thionyl chloride
With thionyl chloride In toluene for 2h; Heating;

(R)-1-(1-Naphthyl)ethylamine (3886-70-2) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → cinacalcet (226256-56-0)

Conditions	Yield
With tris(pentafluorophenyl)borate; phenylsilane In dibutyl ether at 120℃; for 24h; Solvent; Reagent/catalyst; Concentration; Inert atmosphere; Schlenk technique;	89%
With tris(pentafluorophenyl)borate; phenylsilane In dibutyl ether at 120℃; for 20h; Schlenk technique; Inert atmosphere;	87%
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 36h; Glovebox; Molecular sieve; Schlenk technique;

(S)-2-(p-tolylsulfinyl)aniline + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → (S)-3-(3-trifluoromethylphenyl)-N-(2-(p-tolylsulfinyl)phenyl)propanamide

Conditions	Yield
With dmap; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In N,N-dimethyl-formamide at 20℃; for 16h;	86%

(R)-1-(1-Naphthyl)ethylamine (3886-70-2) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → (R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide (1005450-55-4)

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 15h; Inert atmosphere;	83%
Stage #1: 3-(3-trifluoromethylphenyl)propanoic acid With 1,1'-carbonyldiimidazole In dichloromethane for 1h; Stage #2: (R)-1-(1-Naphthyl)ethylamine In dichloromethane at 25 - 35℃; Solvent; Temperature;	82.94%
Stage #1: 3-(3-trifluoromethylphenyl)propanoic acid With thionyl chloride; N,N-dimethyl-formamide In toluene at 25 - 75℃; for 2h; Stage #2: (R)-1-(1-Naphthyl)ethylamine With triethylamine In dichloromethane; toluene at 0 - 5℃; for 1.5 - 2h;	70.87%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) + diisopropylamine (108-18-9) → C16H22F3NO

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 12h;	79%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → 3-[3-(trifluoromethyl)phenyl]propanal (21172-41-8)

Conditions	Yield
With succinic acid anhydride; 4,4'-dibromo-2,2'-bipyridine; diphenylsilane; nickel(II) hydroxide In tetrahydrofuran at 70℃; for 10h; Schlenk technique; Inert atmosphere;	75%
Multi-step reaction with 2 steps 1: 85 percent / LAH 2: 65 percent / (COCl)2/DMSO; Et3N View Scheme
Multi-step reaction with 2 steps 1.1: sulfuric acid / 30 - 45 °C 2.1: diisobutylaluminium hydride / toluene; hexane / 2.5 h / -80 - -78 °C 2.2: -80 - -78 °C View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere; Schlenk technique 2: Dess-Martin periodane / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere; Schlenk technique View Scheme
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

(R)-1-(1-Naphthyl)ethylamine (3886-70-2) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → cinacalcet hydrochloride (364782-34-3)

Conditions	Yield
Stage #1: (R)-1-(1-Naphthyl)ethylamine; 3-(3-trifluoromethylphenyl)propanoic acid With platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; phenylsilane; 1,2-bis-(diphenylphosphino)ethane In dibutyl ether at 120℃; for 18h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride In diethyl ether at -20℃; Schlenk technique; Inert atmosphere;	74%

2-methyl-1H-indole (95-20-5) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → C19H18F3N

Conditions	Yield
With aluminium(III) triflate; Co(acac)3; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] at 140℃; under 22502.3 Torr; for 18h; Autoclave; Sealed tube;	72%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) + aniline (62-53-3) → N-(3-(3-(trifluoromethyl)phenyl)propyl)aniline

Conditions	Yield
With cobalt(II) tetrafluoroborate hexahydrate; (p-anisyl)triphos; hydrogen In 1,4-dioxane at 140℃; under 30003 Torr; for 24h; Autoclave; Green chemistry;	69%

Succinimide (123-56-8) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → 3-(3-trifluoromethylphenyl)propanoyl succinimide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 18h; Inert atmosphere;	53%
Stage #1: 3-(3-trifluoromethylphenyl)propanoic acid With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In tetrahydrofuran for 0.5h; Inert atmosphere; Stage #2: Succinimide In tetrahydrofuran for 48h;	44%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) + N-(6-(3-amino-4-fluorophenoxy)benzo[d]thiazol-2-yl)cyclopropanecarboxamide → N-(6-(4-fluoro-3-(3-(3-(trifluoromethyl)phenyl)propionylamino)phenoxy)benzo[d]thiazol-2-yl)cyclopropanecarboxamide

Conditions	Yield
With HATU In pyridine at 85℃; for 8h; Inert atmosphere;	39%

2-amino-1-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)ethanone (1020656-57-8) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → N-(2-oxo-2-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propanamide (1020656-11-4)

Conditions	Yield
Stage #1: 3-(3-trifluoromethylphenyl)propanoic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: 2-amino-1-(1-phenyl-3,4-dihydropyrrolo[1,2-a]pyrazin-2(1H)-yl)ethanone In dichloromethane at 20℃; for 16h;	38%

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → 3-[3-(trifluoromethyl)cyclohexyl]propanoic acid (329-02-2)

Conditions	Yield
With acetic acid; platinum Hydrogenation;

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) + diazomethyl-trimethyl-silane (18107-18-1) → methyl 3-(3-(trifluoromethyl)phenyl)propanoate (294856-02-3)

Conditions	Yield
With methanol Esterification;

4-{2-[(1S)-((S)-tert-butanesulfinylamino)-3-methylbutyl]-4-(trifluoromethyl)phenyl}-1-piperazine (851484-80-5) + 3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → 2-Methyl-propane-2-sulfinic acid [(S)-3-methyl-1-(5-trifluoromethyl-2-{4-[3-(3-trifluoromethyl-phenyl)-propionyl]-piperazin-1-yl}-phenyl)-butyl]-amide

Conditions	Yield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane; N,N-dimethyl-formamide

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → [(S)-1-(7,8-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / LAH 2: 65 percent / (COCl)2/DMSO; Et3N View Scheme

3-(3-trifluoromethylphenyl)propanoic acid (585-50-2) → [(R)-1-(7,8-Dihydro-naphthalen-1-yl)-ethyl]-[3-(3-trifluoromethyl-phenyl)-propyl]-amine

Conditions	Yield
Multi-step reaction with 3 steps 1: 85 percent / LAH 2: 65 percent / (COCl)2/DMSO; Et3N View Scheme

Upstream product

• 402-24-4 3-(trifluoromethyl)styrene 
• 3495-36-1 cesium formate 
• 1186194-84-2 dimethyl 2-(3-(trifluoromethyl)benzyl)malonate 
• 705-29-3 3-Trifluoromethylbenzyl chloride 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 
• 95096-06-3 3-(3-(trifluoromethyl)phenyl)propanenitrile 
• 294856-02-3 methyl 3-(3-(trifluoromethyl)phenyl)propanoate 
• 3984-22-3 2-vinyl-1,3-dioxolane 
• 779-89-5 3-(trifluoromethyl)cinnamic acid 

Downstream Products

• 1005450-55-4 (R)‐N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide 
• 226256-56-0 cinacalcet 
• 1393911-92-6 C₂₂H₁₇F₃N₂OS 
• 78573-45-2 3-[3-(trifluoromethyl)phenyl]propan-1-ol 
• 955371-05-8 N‐(1‐(naphthalen‐1‐yl)ethyl)‐3‐(3‐trifluoromethylphenyl)propanamide 
• 807667-31-8 2-chloro-3-(3-trifluoromethyl-phenyl)-propionaldehyde 
• 364782-34-3 cinacalcet hydrochloride 

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