DIMETHYL 5-IODOISOPHTHALATE Chemical Properties

Melting point:

105 °C

Boiling point:

160°C 1mm

Density 

1.708±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Chloroform (Slightly), Methanol (Slightly, Heated)

form 

Solid

color 

Pale Beige

InChI

InChI=1S/C10H9IO4/c1-14-9(12)6-3-7(10(13)15-2)5-8(11)4-6/h3-5H,1-2H3

InChIKey

DIAONVDUSXRXCE-UHFFFAOYSA-N

SMILES

C1(C(OC)=O)=CC(I)=CC(C(OC)=O)=C1

CAS DataBase Reference

51839-15-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

20/21/22-36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29163990

DIMETHYL 5-IODOISOPHTHALATE Usage And Synthesis

Uses

Dimethyl 5-Iodoisophthalate is used for succinimidyl 3-iodobenzoate (SIB) with DOTA as prosthetic group for multi-modal labeling enhancing tumor uptake of radiolabelled monoclonal antibodies (mAbs).

Synthesis

Under argon protection, dimethyl 5-aminoisophthalate (1) (6.27 g, 30.0 mmol) was added to 39 mL of 2 M hydrochloric acid pre-cooled in an ice bath. The reaction mixture was stirred at 0 °C or lower for several minutes before 21.6 mL of pre-cooled aqueous sodium nitrite (2.52 g, 36.5 mmol, 1.2 eq.) was added slowly and dropwise. Subsequently, 30 mL of dichloromethane was added and stirring was continued for 5 hours after the reaction mixture was brought to room temperature. Upon completion of the reaction, 70 mL of aqueous potassium iodide (7.47 g, 45.0 mmol, 1.5 eq.) was added slowly and dropwise under ice bath cooling conditions and the mixture was stirred at room temperature for 12 hours. At the end of the reaction, the aqueous layer was extracted with ethyl acetate, the organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and purified by silica gel column chromatography (silica gel, hexanes as eluent) to afford the target product dimethyl 5-iodoisophthalate (2) (5.285 g, 16.5 mmol, 55% yield). The product was characterized as follows: 1H-NMR (400 MHz, CDCl3) δ: 8.62 (t, 1H, J = 1.4 Hz), 8.53 (s, 2H, J = 1.4 Hz), 3.94 (s, 6H); 13C-NMR (100 MHz, CDCl3) δ: 165.2 (2C), 142.9 (2C), 132.6 ( 2C), 130.2, 93.8, 53.1 (2C); MS (EI) m/z: 320 (M+); HRMS (EI) calculated for C10H9IO4: 319.9546, found: 319.9553; Elemental analysis calculated for C10H9O4: C, 37.52; H, 2.83; found: C, 37.44; H, 2.86.

References

[1] Inorganic Chemistry, 2015, vol. 54, # 9, p. 4377 - 4381
[2] Journal of the American Chemical Society, 2012, vol. 134, # 49, p. 20110 - 20116
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 18, p. 6284 - 6292
[4] Chemical Communications, 2011, vol. 47, # 9, p. 2691 - 2693
[5] Patent: US2018/94017, 2018, A1. Location in patent: Paragraph 0061; 0064; 0065

DIMETHYL 5-IODOISOPHTHALATE(51839-15-7)Related Product Information

• Dimethyl isophthalate
• 5-IODO-MONO-METHYL ISOPHTHALATE
• DIMETHYL 5-IODOISOPHTHALATE
• 3-Iodobenzoic acid
• 3-IODO-5-METHYL-BENZOIC ACID METHYL ESTER
• 3-IODO-5-METHYL-BENZOIC ACID
• Methyl 3-iodobenzoate
• 1-Iodo-3,5-dimethylbenzene