2,6-diiodophenol

Structural formula
General
Surname	2,6-diiodophenol
Molecular formula	C 6 H 4 I 2 O
External identifiers / databases
CAS number 28177-54-0 EC number 830-033-3 ECHA InfoCard 100.265.645 PubChem 10405322 Wikidata Q209279
properties
Molar mass	345.9 g mol −1
Physical state	firmly
Melting point	65.5-67.5 ° C
safety instructions
GHS hazard labeling no classification available
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2,6-Diiodophenol is a chemical compound that belongs to both the phenols and the halogen aromatic compounds .

presentation

2,6-Diiodophenol was first produced in 1883 by C. Schall from sodium phenolate and elemental iodine . Proof that the diiodophenol obtained from Schall was the 2,6-isomer was not provided until 1902 by MP Brenans. This reaction produces 4-iodophenol and 2,4,6-triiodophenol as by-products . Another synthesis option is the reaction of phenol with iodine in hydrogen peroxide , which gives the desired product in very good yields.

Derivatives

Esterification with acetic anhydride yields the acetate, which melts at 107 ° C.

The methyl ether can be produced by methylation with dimethyl sulfate and is also known under the common name 2,6-diiodanisole . Its melting point is 35 ° C. The melting points of other ethers are listed in the table below.

Ethers of 2,6-diiodophenol
Names	2,6-diiodanisole 2,6-diiodomethoxybenzene	2,6-diiodophenetole 2,6-diiodoethoxybenzene	2,6-diiodallyloxybenzene	2,6-diiodobenzyloxybenzene
Structural formula
Molecular formula	C 7 H 6 I 2 O	C 8 H 8 I 2 O	C 9 H 8 I 2 O	C 13 H 10 I 2 O
Molar mass	359.9 g mol −1	373.9 g mol −1	385.9 g mol −1	435.9 g mol −1
description	colorless prisms
Melting point	35 ° C	41-42 ° C	46 ° C	74.5 ° C

The nitration of 2,6-diiodophenol with nitric acid in acetic acid gives a mixture of 2,6-diiodo-4-nitrophenol (CAS number: 305-85-1, melting point 155–156 ° C) and 2-iodo-6- nitrophenol (CAS number: 13073-26-2), the latter being formed with the release of elemental iodine.

The bromination of 2,6-diiodophenol with elemental bromine in acetic acid gives 4-bromo-2,6-diiodophenol , the melting point of which is 128 ° C.

Individual evidence

1. ↑ ^{a b} Dictionary of organic compounds, p. 2499 ( limited preview in Google book search).
2. ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
3. ↑ C. Schall: Influence of iodine on sodium phenol , in: Ber. d. German chem. Ges. , 1883 , 16  (2), pp. 1897-1902; doi : 10.1002 / cber.18830160272 .
4. ↑ ^{a b c d} M. P. Brenans: Sur quelques phénols iodés , in: CR Hebd. Séances Acad. Sci. , 1902 , 134 , p. 357.
5. ↑ Rafael DC Gallo, Karimi S. Gebara, Rozanna M. Muzzi, Cristiano Raminelli: Efficient and selective iodination of phenols promoted by iodine and hydrogen peroxide in water , in: J. Braz. Chem. Soc. , 2010 , 21  (4); doi : 10.1590 / S0103-50532010000400026 .
6. ^ P. Brenans, K. Yeu: Phénols bromodiiodés, composés trihalogénés symétriques in CR Hebd. Séances Acad. Sci. , 1930 , 190 , pp. 1560-1561; Full text .