4-Iodoaniline

4-Iodoaniline Basic information
Product Name:4-Iodoaniline
Synonyms:1-amino-4-iodobenzene;4-IODOANILINE;4-LODANILINE;4-iodo-anilin;4-iodo-benzenamin;4-iodo-Benzenamine;1-Iodo-4-aminobenzene;p-Aminoiodobenzene
CAS:540-37-4
MF:C6H6IN
MW:219.02
EINECS:208-743-4
Product Categories:Building Blocks;C6;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;Pharmaceutical Intermediates;Anilines, Aromatic Amines and Nitro Compounds;Amines;API intermediates;Anilines, Amides & Amines;Iodine Compounds;C2 to C6;Nitrogen Compounds;bc0001
Mol File:540-37-4.mol
4-Iodoaniline Structure
4-Iodoaniline Chemical Properties
Melting point 61-63 °C(lit.)
Boiling point 268.7±23.0 °C(Predicted)
density 1.8155 (estimate)
storage temp. Keep in dark place,Sealed in dry,Room Temperature
solubility H2O: slightly soluble
form Crystalline Powder or Needles
pka3.81(at 25℃)
color Beige to grayish-brown
Water Solubility Slightly soluble in water.Soluble in chloroform, methanol.
Sensitive Light Sensitive
Merck 14,5027
BRN 774101
InChIKeyVLVCDUSVTXIWGW-UHFFFAOYSA-N
CAS DataBase Reference540-37-4(CAS DataBase Reference)
NIST Chemistry ReferenceBenzenamine, 4-iodo-(540-37-4)
EPA Substance Registry SystemBenzenamine, 4-iodo- (540-37-4)
Safety Information
Hazard Codes Xn,Xi
Risk Statements 22-36/37/38-20/21/22
Safety Statements 26-36/37/39-36
RIDADR 2811
WGK Germany 3
RTECS BY3850000
8
Hazard Note Harmful/Irritant
TSCA T
HazardClass 6.1(b)
PackingGroup III
HS Code 29214210
MSDS Information
ProviderLanguage
p-Iodoaniline English
SigmaAldrich English
ACROS English
ALFA English
4-Iodoaniline Usage And Synthesis
Chemical Propertiesbeige to greyish-brown crystalline powder. soluble in alcohol, ether and chloroform, slightly soluble in water.
Uses4-dehydroanilinium ion, a stable distonic isomer of ionized aniline, by collision-activated dissociation of protonated 4-iodoaniline. Palladium-catalyzed carbonylation of 4-iodoaniline gave the corresponding four- armed star polybenzamides. 4-Iodoaniline is a iodine substituted aniline that is widely used as chemical intermediates in the manufacturing of dyes and drugs. 4-Iodoaniline was used to prepare phenyl functionalized graphene oxide (I-Ph-GO).
Usessuzuki reaction
Uses4-Iodoaniline is a iodine substituted aniline that is widely used as chemical intermediates in the manufacturing of pesticides, dyes and drugs. 4-Iodoaniline was shown to be a more potent nephrotoxica nt in vitro than other anilines.
Preparation4-Iodoaniline is obtained by the reaction of aniline and iodine in the presence of sodium bicarbonate. Add aniline and sodium bicarbonate to water and slowly add crushed iodine in stages with vigorous stirring. If the reaction solution is yellow, add a little sodium bisulfite to make it discolor, then filter and get the crude product. Then the product is recrystallized by ethanol to obtain 4-Iodoaniline.
General Description4-Iodoaniline is the most potent methaemoglobin former.
Purification MethodsCrystallise it from pet ether (b 60-80o) by refluxing, then cool it in an ice-salt bath freezing mixture. Dry it in air. Alternatively, crystallise it from EtOH and dry it in vacuo for 6hours at 40o [Edidin et al. J Am Chem Soc 109 3945 1987]. The N-acetyl derivative has m 184o (from MeOH). [Beilstein 12 IV 1544.]
N-[(3,4-dichlorophenyl)methyl]-3-iodoaniline N-[(2-ethoxyphenyl)methyl]-3-iodoaniline N-[(2-bromo-4-fluorophenyl)methyl]-4-iodoaniline N-[(2-chloro-4-fluorophenyl)methyl]-2-iodoaniline N-[(2-chloro-4-fluorophenyl)methyl]-3-iodoaniline N-[(2-fluorophenyl)methyl]-2-iodoaniline N-[(2-fluorophenyl)methyl]-3-iodoaniline N-[(3,5-dimethoxyphenyl)methyl]-3-iodoaniline N-[(3-bromo-4-fluorophenyl)methyl]-4-iodoaniline INT FORMAZAN ALTRENOGEST N-(4-Iodophenyl)acetamide AMINO ACIDS N-[(2-bromo-4-fluorophenyl)methyl]-3-iodoaniline N-[(2-bromo-5-fluorophenyl)methyl]-3-iodoaniline N-[(2-ethoxyphenyl)methyl]-4-iodoaniline N-[(3,4-difluorophenyl)methyl]-4-iodoaniline 1-Iodo-4-nitrobenzene

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