BOLTON-HUNTER REAGENT

The Benzenepropanoic acid, 4-hydroxy-, 2, 5-dioxo-1-pyrrolidinyl ester, with the CAS registry number of 34071-95-9, is also known as N-[(4-Hydroxyhydrocinnamoyl)oxy]succinimide. It belongs to the product category of Aromatic Propionic Acids. Its EINECS registry number is 251-818-1. This chemical's molecular formula is C₁₃H₁₃NO₅ and molecular weight is 263.25. What's more, its IUPAC name is (2, 5-Dioxopyrrolidin-1-yl) 3-(4-hydroxyphenyl)propanoate. In addition, it must be stored in airtight containers at -20 °C.

Physical properties about Benzenepropanoic acid, 4-hydroxy-, 2, 5-dioxo-1-pyrrolidinyl ester are: (1)ACD/LogP: -0.35; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -0.35; (4)ACD/LogD (pH 7.4): -0.35; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 15.36; (8)ACD/KOC (pH 7.4): 15.32; (9)#H bond acceptors: 6; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 6; (12)Polar Surface Area: 72.91 Å²; (13)Index of Refraction: 1.606; (14)Molar Refractivity: 64.62 cm³; (15)Molar Volume: 187.1 cm³; (16)Surface Tension: 65.2 dyne/cm; (17)Density: 1.4 g/cm³; (18)Flash Point: 225.2 °C; (19)Enthalpy of Vaporization: 73.46 kJ/mol; (20)Boiling Point: 448.8 °C at 760 mmHg; (21)Vapour Pressure: 1.13E-08 mmHg at 25 °C.

Preparation: this chemical is prepared by reaction of N-Hydroxy-succinimide with 3-(4-Hydroxy-phenyl)-propionic acid. The reaction needs reagent DCC and solvent Tetrahydrofuran. The reaction time is 2 hours with reaction temperature of 0 °C. The yield is about 81 %.

Uses: it is used to produce other chemicals. For example, it is used to produce N-Succinimidyl 3-(4-hydroxy-3-[124I]iodophenyl)propionate. This reaction needs reagents Sodium [124I]iodide; Sodium [127I]iodide; IodoGen. Meanwhile, it needs catalyst Hydrochloric acid and solvent aq. Phosphate buffer. The reaction time is 1 minute with the pH of 6.5. The yield is about 58 %.

When you are using this chemical, please be cautious about it as the following:
As a chemical, it is irritating to eyes, respiratory system and skin. In addition, this chemical may cause inflammation to the skin or other mucous membranes. During using it, wear suitable protective clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C2N(OC(=O)CCc1ccc(O)cc1)C(=O)CC2
(2) InChI: InChI=1/C13H13NO5/c15-10-4-1-9(2-5-10)3-8-13(18)19-14-11(16)6-7-12(14)17/h1-2,4-5,15H,3,6-8H2
(3) InChIKey: KYRUKRFVOACELK-UHFFFAOYAC