Product Name

  • Name

    3,5-Bis(trifluoromethyl)benzoic acid

  • EINECS 211-970-1
  • CAS No. 725-89-3
  • Article Data17
  • CAS DataBase
  • Density 1.527 g/cm3
  • Solubility Slightly soluble in water.
  • Melting Point 142-143 °C(lit.)
  • Formula C9H4F6O2
  • Boiling Point 223.9 °C at 760 mmHg
  • Molecular Weight 258.12
  • Flash Point 89.2 °C
  • Transport Information
  • Appearance white to light yellow crystal powder
  • Safety 26-36-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 725-89-3 (3,5-Bis(trifluoromethyl)benzoic acid)
  • Hazard Symbols IrritantXi
  • Synonyms 3,5-bis(trifluoromethyl)benzoate;
  • PSA 37.30000
  • LogP 3.42240

Synthetic route

carbon dioxide
124-38-9

carbon dioxide

3,6-bis(trifluoromethyl)bromobenzene
328-70-1

3,6-bis(trifluoromethyl)bromobenzene

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With n-butyllithium In diethyl ether at -75℃;94%
Stage #1: 3,6-bis(trifluoromethyl)bromobenzene With isopropylmagnesium chloride In tetrahydrofuran at -10℃; for 1h;
Stage #2: carbon dioxide In tetrahydrofuran at -45℃; under 1034.3 Torr; for 1h;
94%
Stage #1: 3,6-bis(trifluoromethyl)bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere;
Stage #2: carbon dioxide In tetrahydrofuran; hexane at -78 - 20℃;
90.3%
(i) Mg, I2, Et2O, (ii) /BRN= 1900390/; Multistep reaction;
3,5-bis(trifluoromethyl)benzoyl fluoride
401-96-7

3,5-bis(trifluoromethyl)benzoyl fluoride

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With water In diethyl ether85%
2-hydroxy-4-phenylbutanenitrile
121054-03-3

2-hydroxy-4-phenylbutanenitrile

3,5-bis(trifluoromethyl)benzoic anhydride
155929-90-1

3,5-bis(trifluoromethyl)benzoic anhydride

A

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

B

1-cyano-3-phenylpropyl 3,5-bis(trifluoromethyl)benzoate

1-cyano-3-phenylpropyl 3,5-bis(trifluoromethyl)benzoate

Conditions
ConditionsYield
Stage #1: 2-hydroxy-4-phenylbutanenitrile; 3,5-bis(trifluoromethyl)benzoic anhydride With triethylamine In dichloromethane at 20℃; for 2h;
Stage #2: With hydrogenchloride In water
A n/a
B 85%
1,3,5-tris(trifluoromethyl)benzene
729-81-7

1,3,5-tris(trifluoromethyl)benzene

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
Stage #1: 1,3,5-tris(trifluoromethyl)benzene With trifluorormethanesulfonic acid In chloroform for 4h; Inert atmosphere;
Stage #2: With water In chloroform Inert atmosphere;
82%
3,5-bis(trifluoromethyl)styrene
349-59-7

3,5-bis(trifluoromethyl)styrene

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With methyl 3,5-bis((1H-1,2,4-triazol-1-yl)methyl)benzoate; oxygen; sodium acetate; nickel dibromide at 120℃; under 760.051 - 912.061 Torr; for 48h; chemoselective reaction;80%
carbon monoxide
201230-82-2

carbon monoxide

3,5-bis(trifluoromethyl)iodobenzene
328-73-4

3,5-bis(trifluoromethyl)iodobenzene

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With water; potassium carbonate In acetonitrile at 100℃; under 3750.38 Torr; for 0.0161111h;79%
(2S,3S,5R,6R)-5-hydroxy-2-methoxy-4-oxo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl pivalate
90213-79-9

(2S,3S,5R,6R)-5-hydroxy-2-methoxy-4-oxo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl pivalate

3,5-bis(trifluoromethyl)benzoic anhydride
155929-90-1

3,5-bis(trifluoromethyl)benzoic anhydride

A

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

B

(2R,3R,5S,6S)-6-methoxy-4-oxo-5-(pivaloyloxy)-2-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl 3,5-bis(trifluoromethyl)benzoate

(2R,3R,5S,6S)-6-methoxy-4-oxo-5-(pivaloyloxy)-2-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl 3,5-bis(trifluoromethyl)benzoate

Conditions
ConditionsYield
Stage #1: (2S,3S,5R,6R)-5-hydroxy-2-methoxy-4-oxo-6-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl pivalate; 3,5-bis(trifluoromethyl)benzoic anhydride With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;
Stage #2: With hydrogenchloride In water
A n/a
B 71.8%
carbon dioxide
124-38-9

carbon dioxide

1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

A

2,4-bis(trifluoromethyl)benzoic acid
32890-87-2

2,4-bis(trifluoromethyl)benzoic acid

B

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With N,N,N',N'',N'''-pentamethyldiethylenetriamine; sec.-butyllithium In tetrahydrofuran at -75℃; for 2h;A 38%
B 14%
3,5-bis(trifluoromethyl)benzoic anhydride
155929-90-1

3,5-bis(trifluoromethyl)benzoic anhydride

A

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

B

1,2-O-isopropylidene-5-O-(3,5-bis(trifluoromethyl)benzoyl)-α-D-xylo-hexofuranurono-6,3-lactone

1,2-O-isopropylidene-5-O-(3,5-bis(trifluoromethyl)benzoyl)-α-D-xylo-hexofuranurono-6,3-lactone

Conditions
ConditionsYield
Stage #1: 3,5-bis(trifluoromethyl)benzoic anhydride; D-glucurono-3,6-lactone acetonide With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 2h;
Stage #2: With hydrogenchloride In water
A n/a
B 31.6%
carbon dioxide
124-38-9

carbon dioxide

1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

A

2,6-bis(trifluoromethyl)benzoic acid
24821-22-5

2,6-bis(trifluoromethyl)benzoic acid

B

2,4-bis(trifluoromethyl)benzoic acid
32890-87-2

2,4-bis(trifluoromethyl)benzoic acid

C

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine; n-butyllithium 1.) THF, -78 deg C, 1.5 h, 2.) THF; Yield given; Multistep reaction. Yields of byproduct given;
1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 94 percent / sulfuric acid; 1,3-dibromo-5,5-dimethylhydantoin / acetic acid / 4 h / 45 °C
2.1: i-PrMgCl / tetrahydrofuran / 1 h / -10 °C
2.2: 94 percent / tetrahydrofuran / 1 h / -45 °C / 1034.3 Torr
View Scheme
Multi-step reaction with 2 steps
1: 87 percent / 96percent H2SO4, N,N'-dibromo-5,5-dimethylhydantoin / 24 h / 0 °C
2: 94 percent / BuLi / diethyl ether / -75 °C
View Scheme
Multi-step reaction with 2 steps
2: (i) Mg, I2, Et2O, (ii) /BRN= 1900390/
View Scheme
4,4'-dimethoxybenzhydryl 3,5-bis(trifluoromethyl)benzoate

4,4'-dimethoxybenzhydryl 3,5-bis(trifluoromethyl)benzoate

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
In ethanol; dichloromethane at 25℃; Kinetics;
3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
785-56-8

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

A

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

B

1-cyano-3-phenylpropyl 3,5-bis(trifluoromethyl)benzoate

1-cyano-3-phenylpropyl 3,5-bis(trifluoromethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphoric acid; acetic anhydride / 150 - 190 °C
2: triethylamine / dichloromethane / 2 h / 20 °C
View Scheme
3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
785-56-8

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

A

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

B

(2R,3R,5S,6S)-6-methoxy-4-oxo-5-(pivaloyloxy)-2-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl 3,5-bis(trifluoromethyl)benzoate

(2R,3R,5S,6S)-6-methoxy-4-oxo-5-(pivaloyloxy)-2-(pivaloyloxymethyl)tetrahydro-2H-pyran-3-yl 3,5-bis(trifluoromethyl)benzoate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphoric acid; acetic anhydride / 150 - 190 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
View Scheme
3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride
785-56-8

3,5-bis(trifluoromethyl)phenyl carboxylic acid chloride

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: phosphoric acid; acetic anhydride / 150 - 190 °C
2: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C
View Scheme
carbon dioxide
124-38-9

carbon dioxide

1,3-bis(trifluoromethyl)benzene
402-31-3

1,3-bis(trifluoromethyl)benzene

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
Stage #1: carbon dioxide; 1,3-bis(trifluoromethyl)benzene With [1,2-bis(dicyclohexylphosphino)ethane]rhodium(I) chloride dimer; Al(3+)*1.5CH3(1-)*1.5C2H5O(1-); tetramethylurea In N,N-dimethyl acetamide at 20 - 145℃; under 760.051 Torr; for 6h; Inert atmosphere;
Stage #2: With hydrogenchloride In diethyl ether; N,N-dimethyl acetamide; water Catalytic behavior; Inert atmosphere; regioselective reaction;
3,5-bis(trifluoromethyl)benzenemethanol
32707-89-4

3,5-bis(trifluoromethyl)benzenemethanol

A

3,5-Bis(trifluoromethyl)benzaldehyde
401-95-6

3,5-Bis(trifluoromethyl)benzaldehyde

B

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; laccase from Trametes versicolor; oxygen In water at 20℃; for 120h; Enzymatic reaction;A 48 %Spectr.
B 21 %Spectr.
(S)-Mandelic acid
17199-29-0

(S)-Mandelic acid

diruthenium tetra(3,5-bis(trifluoromethyl)) benzoate

diruthenium tetra(3,5-bis(trifluoromethyl)) benzoate

A

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

B

diruthenium tetra (L-mandelate)

diruthenium tetra (L-mandelate)

Conditions
ConditionsYield
at 55℃; for 2h; Kinetics; Equilibrium constant; Temperature;
diruthenium tetra(3,5-bis(trifluoromethyl)) benzoate

diruthenium tetra(3,5-bis(trifluoromethyl)) benzoate

acetic acid
64-19-7

acetic acid

A

tetra-μ-acetato-ruthenium(II)

tetra-μ-acetato-ruthenium(II)

B

3,5-bistrifluoromethylbenzoic acid
725-89-3

3,5-bistrifluoromethylbenzoic acid

Conditions
ConditionsYield
at 55℃; for 2h; Kinetics; Equilibrium constant; Temperature;

3,5-Bis(trifluoromethyl)benzoic acid Specification

The IUPAC name of this chemical is 3,5-Bis(trifluoromethyl)benzoic acid. With the CAS registry number 725-89-3 and EINECS registry numbe 211-970-1, it is also named as Benzoic acid, 3,5-bis(trifluoromethyl)-. In addition, the molecular formula is C9H4F6O2 and the molecular weight is 258.12. It is a kind of white to light yellow crystal powder and belongs to the classes of Fluorides; Boronic Acid series; Fluorobenzene; Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides; Salts; Benzoic acid; Miscellaneous; Benzotrifluoride Series; C9; Carbonyl Compounds; Carboxylic Acids. What's more, it should be stored in sealed container, and put them in a cool and dry place.

Physical properties about 3,5-Bis(trifluoromethyl)benzoic acid are: (1)ACD/LogP: 4.29; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.17; (4)ACD/LogD (pH 7.4): 1.19; (5)ACD/BCF (pH 5.5): 8.09; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 38.85; (8)ACD/KOC (pH 7.4): 4.06; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 1; (12)Polar Surface Area: 26.3 Å2; (13)Index of Refraction: 1.424; (14)Molar Refractivity: 43.14 cm3; (15)Molar Volume: 168.9 cm3; (16)Polarizability: 17.1 ×10-24cm3; (17)Surface Tension: 26.6 dyne/cm; (18)Density: 1.527 g/cm3; (19)Flash Point: 89.2 °C; (20)Enthalpy of Vaporization: 48.66 kJ/mol; (21)Boiling Point: 223.9 °C at 760 mmHg; (22)Vapour Pressure: 0.0537 mmHg at 25°C.

Preparation of 3,5-Bis(trifluoromethyl)benzoic acid: it can be prepared by carbon dioxide and 1-bromo-3,5-bis-trifluoromethyl-benzene. This reaction will need reagent BuLi and solvent diethyl ether. The yield is about 94% at reaction temperature of -75 °C.

3,5-Bis(trifluoromethyl)benzoic acid can be prepared by carbon dioxide and 1-bromo-3,5-bis-trifluoromethyl-benzene.

Uses of 3,5-Bis(trifluoromethyl)benzoic acid: it can be used to get 3,5-bis(trifluoromethyl)benzyl alcohol. This reaction will need reagent LiAlH4 and solvent diethyl ether. The reaction time is 3 hours by heating. The yield is about 90%.

3,5-Bis(trifluoromethyl)benzoic acid can be used to get 3,5-bis(trifluoromethyl)benzyl alcohol

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Although it is slightly harmful to the water, you can not let a large number of this products contact with the groundwater, the waterway or sewage system. If without government permission, do not put this material into surroundings.

You can still convert the following datas into molecular structure:
(1)SMILES: FC(F)(F)c1cc(cc(c1)C(F)(F)F)C(=O)O
(2)InChI: InChI=1/C9H4F6O2/c10-8(11,12)5-1-4(7(16)17)2-6(3-5)9(13,14)15/h1-3H,(H,16,17)
(3)InChIKey: HVFQJWGYVXKLTE-UHFFFAOYAR

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 100mg/kg (100mg/kg) BEHAVIORAL: REGIDITY

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Medicinal Chemistry. Vol. 11, Pg. 1020, 1968.

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