2-Chloro-5-(trifluoromethyl)benzoic acid Chemical Properties

Melting point:

93-96 °C (lit.)

Boiling point:

270.4±40.0 °C(Predicted)

Density 

1.523±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

2.45±0.25(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H4ClF3O2/c9-6-2-1-4(8(10,11)12)3-5(6)7(13)14/h1-3H,(H,13,14)

InChIKey

WLXRKCGYQAKHSJ-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC(C(F)(F)F)=CC=C1Cl

CAS DataBase Reference

657-06-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

2-Chloro-5-(trifluoromethyl)benzoic acid Usage And Synthesis

Chemical Properties

Off-white powder

Uses

2-Chloro-5-(trifluoromethyl)benzoic acid may be used as surrogate standard to investigate the pesticide exposure and home contamination in urine and hand wipe samples collected from farmers.

General Description

2-Chloro-5-(trifluoromethyl)benzoic acid is a carboxylic acid building block.

Synthesis

Under nitrogen protection, n-BuLi (2.5 M hexane solution, 22 mL, 55 mmol) was added dropwise to a stirred solution of 4-chlorobenzotrifluoride (9.177 g, 50.8 mmol) and TMEDA (6.3030 g, 54.2 mmol) in THF (89 mL) over a period of 8 min, keeping the reaction temperature at -78 °C. After 52 min of reaction, the reaction solution was transferred via cannula to a vessel containing dry ice (~200 g) within 20 min. Care was taken to keep the cannula fully lagged to prevent rapid darkening of the anion solution on slight warming. The mixture was slowly warmed to room temperature and the solvent was evaporated (temperature controlled at <30°C) to give an orange to yellow solid. The solid was dissolved in water (70 mL) and the aqueous layer was washed with ether (3 x 30 mL). Subsequently, the aqueous layer was adjusted to pH 1 with acid and extracted with DCM (3 x 30 mL). The organic layers were combined, evaporated to dryness (<30°C), and the residue was dissolved in refluxed hexane, hot-filtered and cooled to 4°C for overnight crystallization. The first sand-colored solids (4.5243 g) were obtained by vacuum filtration. The mother liquor was concentrated to half volume to give a second batch of lemon yellow crystals (2.2998 g). The two batches were dried under vacuum to give 4.5030 g and 2.2093 g, respectively, for a total yield of 6.712 g (59%).LCMS analysis showed a purity of 96.3 Apercent (at 254 nm) for the first batch and 95.1 Apercent for the second batch, [M + H] + 225.0, at an Rt = 5.94 min. No starting material was detected.

References

[1] Tetrahedron Letters, 1996, vol. 37, # 16, p. 2767 - 2770
[2] Patent: EP2468746, 2012, A1. Location in patent: Page/Page column 6
[3] Patent: WO2012/85654, 2012, A1. Location in patent: Page/Page column 6; 7
[4] Patent: WO2013/38259, 2013, A1. Location in patent: Page/Page column 11-12

2-Chloro-5-(trifluoromethyl)benzoic acid(657-06-7)Related Product Information

• 4-(Chloromethyl)benzoic acid
• o-Toluic acid
• 4-(Trifluoromethyl)benzoic acid
• 4-(Aminomethyl)benzoic acid
• 3-Chloroperoxybenzoic acid
• m-Toluic acid
• 3-(Trifluoromethyl)benzoic acid
• p-Toluic acid
• 2-Chloro-5-trifluoromethylpyridine
• 4-Bromomethylbenzoic acid
• 3-(Trifluoromethyl)benzaldehyde
• 2-CHLORO-5-METHYLBENZOIC ACID
• 2,6-Dichloro-3-(trifluoromethyl)-benzoic acid
• 2-Chloro-5-(trifluoromethyl)benzyl alcohol
• 4-Chlorobenzotrifluoride
• 2-Chloro-5-trifluoromethylbenzaldehyde
• 1-Chloro-2-methyl-4-(trifluoromethyl)benzene
• Difluorochloromethane