Basic information
- CAS
540-37-4- Standard SMILES
Nc1ccc(I)cc1- InChIKey
VLVCDUSVTXIWGW-UHFFFAOYSA-N- Molecular formula
- C6H6IN
- Average molar mass
- 219.02 g/mol
- Monoisotopic mass
- 218.95449719
Overview
reagent
Names & identifiers
- Preferred name
- 4-Iodoaniline
- IUPAC
- 4-iodoaniline
- English name
- 4-Iodoaniline
- Molecular formula
- C6H6IN
- Molecular weight
- 219.02
Names & synonyms
4-IODOANILINE540-37-4p-IodoanilineBenzenamine, 4-iodo-4-Iodobenzenamine0BMK56397BNSC-9246DTXSID9060239RefChem:858089DTXCID5041564208-743-44-iodophenylamine
Show more names
1-amino-4-iodobenzene4-IodoaniL4-LODANILINE4-iodo-anilinp-iodo-anilinp－lodoaniline
Aniline, p-iodo-Aniline, 4-iodo-p-Aminophenyl iodide4-Iodo-phenylamineMFCD000078484-iodobenzeneamine4-iodo-benzenamineCCRIS 9122
Database identifiers
- CAS
540-37-4- PubChem CID
- 10893
- DTXSID
DTXSID9060239- ChEMBL
CHEMBL41790- UNII
- 0BMK56397B
- EC Number
- 208-743-4
- Nikkaji
- J60.430E
Properties
Computed structural properties
- XLogP
- 2.3
- Topological polar surface area
- 26 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 0
- Heavy atoms
- 8
- Formal charge
- 0
- Complexity
- 66.9
Experimental & physicochemical properties
Chemical ClassesNitrogen Compounds -> Amines, Aromatic
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP2.34
Vapor Pressure0.00767 [mmHg]
Physical DescriptionWhite solid; [Merck Index] Light brown crystalline powder; [Alfa Aesar MSDS]
Physicochemical properties
- Melting point
- 61 · 61-63 °C(lit.)
- Boiling point
- 268.7 · 268.7±23.0 °C(Predicted)
- Density
- 1.8155 · 1.8155 (estimate)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- solubility
- 2 O: · H2O: slightly soluble
- form
- Crystalline Powder or Needles
- pka
- 3.81 · 3.81(at 25℃)
- color
- Beige to grayish-brown
- Water Solubility
- Slightly soluble in water.Soluble in chloroform, methanol.
- Sensitive
- Light Sensitive
- Merck
- 14 · 14,5027
- BRN
- 774101 · 774101
- InChI
- 1S/C6H6IN/c7-5-1-3-6(8)4-2-5/h1-4H,8H2
- InChIKey
- VLVCDUSVTXIWGW-UHFFFAOYSA-N
- SMILES
- Nc1ccc(I)cc1
- CAS DataBase Reference
- 540 · 540-37-4(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 BMK56397B · 0BMK56397B
- NIST Chemistry Reference
- 4 · Benzenamine, 4-iodo-(540-37-4)
- EPA Substance Registry System
- 4 · Benzenamine, 4-iodo- (540-37-4)
- UNSPSC Code
- 12352100 · 12352100
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38-20/21/22
- Safety Statements
- 26 · 26-36/37/39-36
- RIDADR
- 2811 · 2811
- WGK Germany
- 3 · 3
- RTECS
- 3850000 · BY3850000
- F
- 8 · 8
- Hazard Note
- Harmful/Irritant
- TSCA
- TSCA listed
- HazardClass
- 6.1 · 6.1(b)
- PackingGroup
- III
- HS Code
- 29214210 · 29214210
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H302 (98.4%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 63 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
Chemical: Benzenamine, 4-iodo-
4-Iodoaniline: Does not have an individual approval but may be used under an appropriate group standard
Hazards Summary
Causes degenerative spinal cord changes, structural changes in peripheral nerve or sheath, dyspnea, cyanosis, and weight loss in acute oral studies of rats; [RTECS] A skin and strong eye irritant; May induce methemoglobinemia; Harmful by inhalation; Toxic by ingestion and skin absorption; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (98.4%)
Toxicology
Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Safety data
- F
- 8
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- BY3850000
- ridadr
- 2811
- hs_code
- 29214210
- risk_code
- 22-36/37/38-20/21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Harmful/Irritant
- safety_code
- 26-36/37/39-36
- hazard_class
- 6.1(b)
- Storage Class
- 11 - Combustible Solids
- packing_group
- III
- target organs
- Respiratory system
- Hazard statements
- H302-H315-H319-H335
- Hazard Classifications
- Acute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P270-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
UsesA reagent; [ChemIDplus]
General Manufacturing InformationBenzenamine, 4-iodo-: ACTIVE
Applications
Usessuzuki reaction
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).
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.
General Description4-Iodoaniline is the most potent methaemoglobin former.
Preparation methods
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.
Upstream & downstream products
Upstream raw materials
Downstream products
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Related reactions
321 records
Compound notes
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