2-BROMO-5-IODOBENZYL ALCOHOL Chemical Properties

Melting point:

112-116°C

Boiling point:

343.3±32.0 °C(Predicted)

Density 

2.211±0.06 g/cm3(Predicted)

storage temp. 

2-8°C

form 

crystalline solid

pka

13.67±0.10(Predicted)

color 

Cream/faint lemon

InChI

InChI=1S/C7H6BrIO/c8-7-2-1-6(9)3-5(7)4-10/h1-3,10H,4H2

InChIKey

WDXHGFYJUQMFDV-UHFFFAOYSA-N

SMILES

C1(CO)=CC(I)=CC=C1Br

Safety Information

WGK Germany 

3

HS Code 

2906290090

2-BROMO-5-IODOBENZYL ALCOHOL Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-bromo-5-iodobenzyl alcohol from 2-bromo-5-iodobenzoic acid: Tetrahydrofuran (99.7 g) and sodium borohydride (15.2 g, 0.4 mol) were added to a reaction flask, followed by a solution of tetrahydrofuran (151 g) of 2-bromo-5-iodobenzoic acid (109.4 g, 0.34 mol, prepared according to Example 2), and the temperature was controlled to be in the range of 10-25°C. A solution of tetrahydrofuran (25 g) of sulfuric acid (16.4 g) was added slowly and dropwise to the reaction vessel at 10-30°C. -25°C. A tetrahydrofuran (25 g) solution of sulfuric acid (16.4 g) was slowly added dropwise at 10-30°C to the reaction vessel. After the dropwise addition was completed, the reaction was carried out at room temperature for 2 hours. Subsequently, the reaction mixture was heated to 66°C and refluxed for 2 hours and then cooled to room temperature. 5% hydrochloric acid (235 g) was slowly added dropwise, followed by distillation under reduced pressure (~0.01 MPa) to remove the tetrahydrofuran. Methyl tert-butyl ether (326.7 g) and water (222.7 g) were added to dissolve the solids and after cooling to 15-25°C, the organic layer was separated and evaporated under reduced pressure (-0.095 MPa). Toluene (108.8 g) and water (108.8 g) were added and the mixture was heated to 60°C and kept for 1 hr, then cooled to 18-22°C. It was filtered and dried to give 89.1 g of an off-white solid product, which was assayed to contain >99%, giving a yield of 85.1%.

References

[1] Patent: CN107954861, 2018, A. Location in patent: Paragraph 0096; 0097
[2] Patent: WO2018/15410, 2018, A1. Location in patent: Paragraph 0304-0307
[3] Patent: US2014/31540, 2014, A1. Location in patent: Paragraph 0072; 0073; 0074
[4] Patent: WO2014/16381, 2014, A1. Location in patent: Page/Page column 12
[5] Patent: WO2014/161836, 2014, A1. Location in patent: Page/Page column 42

2-BROMO-5-IODOBENZYL ALCOHOL(946525-30-0)Related Product Information

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