2-(4-Diethylamino-2-hydroxybenzoyl)benzoic acid Chemical Properties

Melting point:

180°C(dec.)(lit.)

Boiling point:

537.1±45.0 °C(Predicted)

Density 

1?+-.0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

solubility 

soluble in Dimethylformamide

form 

powder to crystal

pka

3.27±0.36(Predicted)

color 

White to Light yellow to Light red

InChI

InChI=1S/C18H19NO4/c1-3-19(4-2)12-9-10-15(16(20)11-12)17(21)13-7-5-6-8-14(13)18(22)23/h5-11,20H,3-4H2,1-2H3,(H,22,23)

InChIKey

FQNKTJPBXAZUGC-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1O

CAS DataBase Reference

5809-23-4(CAS DataBase Reference)

EPA Substance Registry System

Benzoic acid, 2-[4-(diethylamino)-2-hydroxybenzoyl]- (5809-23-4)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

RTECS 

DG8545700

HS Code 

29163990

2-(4-Diethylamino-2-hydroxybenzoyl)benzoic acid Usage And Synthesis

Uses

2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid could synthesize a novel fluorescent matrix, a hybrid (CzR) of carbazole, i.e. 2-hydroxycarbazole and rhodamine according to acid-promoted Friedel-Crafts acylation procedure with 2-hydroxycarbazole[1].

Synthesis

To a stirred solution of compound 2 (1.0 eq.) in CH2Cl2 was slowly added a solution of BBr3 (1.9 eq.) in CH2Cl2 at -78 °C. After 1 hour of reaction, the mixture was slowly warmed to -25°C. Upon completion of the reaction, the reaction mixture was quenched with H2O and the solvent was subsequently evaporated to give the crude product. For compounds 3a to 3c, the pure product was obtained by recrystallization from MeOH/H2O solution as a yellow solid, while compound 3d was purified by silica gel column chromatography to give a yellow viscous oil. The 1H-NMR (CDCl3, 500 MHz) data for compound 3a (2-[4-(diethylamino)-2-hydroxybenzoyl]benzoic acid) were as follows: δ 12.65 (s, 1H), 8.07 (dd, 1H, J = 7.8, 0.9Hz), 7.58 (td, 1H, J = 7.6, 1.4Hz), 7.51 (td, 1H, J = 7.8, 1.4Hz), 7.51 (td, 1H, 1H, J = 7.6, 1.4Hz). J = 7.8, 1.4Hz), 7.34 (dd, 1H, J = 7.6, 1.1Hz), 6.91 (d, 1H, J = 8.9Hz), 6.11 (sd, 1H, J = 2.5Hz), 6.03 (dd, 1H, J = 9.2, 2.5Hz), 3.37 (q, 4H, J = 7.1Hz), 1.18 (t, 6H, J = 7.1 Hz).13C-NMR (CDCl3, 500 MHz) data were as follows: δ 199.0, 167.5, 165.2, 153.6, 140.6, 134.6, 131.6, 130.4, 129.5, 128.9, 127.6, 110.1, 103.5, 96.7, 124.5, 12.5. HRMS (EI) calculated value C19H21NO4 (M+): 313.1314, measured value: 313.1313. yield was 65%.

References

[1] Xiaojie Jiao . “A highly selective and pH-tolerance fluorescent probe for Cu2+ based on a novel carbazole-rhodamine hybrid dye.” Dyes and Pigments 160 (2019): Pages 633-640.

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