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HomeProduct name list2'-Iodoacetophenone

2'-Iodoacetophenone

2'-Iodoacetophenone Structural

What is 2'-Iodoacetophenone?

Chemical properties

Clear yellow liquid

The Uses of 2'-Iodoacetophenone

2′-Iodoacetophenone (2-Iodoacetophenone) may be used in the synthesis of:
indene derivatives
di-(o-acetylphenyl)acetylene
indenol derivative

Preparation

2'-Iodoacetophenone can be synthesized by diazotization of 2-acetylaniline.
To a solution of p-TsOH (22.80 g, 120 mmol) in CH3CN (160 mL) was added an aromatic amine (40 mmol). The resulting amine salt suspension was cooled to 0-5°C. A solution of NaNO2 (5.52 g, 80 mmol) in H2O (12 mL) and KI (16.6 g, 100 mmol) in H2O (12 mL) were added sequentially. The reaction mixture was stirred for 10 minutes, then allowed to warm to ambient temperature and stirred until all the amine was consumed. To the reaction mixture were then added H2O (700 mL), NaHCO3 (1M; until pH=9-10) and Na2S2O3 (2M, 80 mL). The reaction mixture was extracted with EtOAc and purified by column chromatography (hexanes:EtOAc, 9:1 v/v) to give 2'-iodoacetophenone:yellow oil in 94% yield.

Reactions

2'-Iodoacetophenone is a bioactive molecule that reacts with boronic acids to form aryl boronic acid derivatives. This reaction can be carried out in chlorobenzene or dihedral solvents, and it is scalable and applicable to a variety of boronic acids. The product of this reaction is an organocatalyst for the synthesis of bioactive molecules. 2'-Iodoacetophenone also reacts with dipole-containing additives to form dichlorodiphenyldichloroethane, which has been used as a fungicide, insecticide, and herbicide.

General Description

2′-Iodoacetophenone is a halogenated aromatic ketone.

Properties of 2'-Iodoacetophenone

Boiling point: 139-140°C 12mm
Density  1.72 g/mL at 25 °C(lit.)
refractive index  n20/D 1.618(lit.)
Flash point: 218 °F
storage temp.  Keep in dark place,Sealed in dry,Room Temperature
form  Liquid
color  Clear yellow
Specific Gravity 1.720
Sensitive  Light Sensitive
BRN  2325078
CAS DataBase Reference 2142-70-3(CAS DataBase Reference)

Safety information for 2'-Iodoacetophenone

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
Precautionary Statement Codes P264:Wash hands thoroughly after handling.
P264:Wash skin thouroughly after handling.
P280:Wear protective gloves/protective clothing/eye protection/face protection.
P321:Specific treatment (see … on this label).
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P332+P313:IF SKIN irritation occurs: Get medical advice/attention.
P337+P313:IF eye irritation persists: Get medical advice/attention.

Computed Descriptors for 2'-Iodoacetophenone

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