(Diacetoxyiodo)benzene
- Iupac Name：[acetyloxy(phenyl)-$l^{3}-iodanyl] acetate
- CAS No.: 3240-34-4
- Molecular Weight：322.1
- Modify Date.: 2023-03-26 16:51
- Introduction: (Diacetoxyiodo)benzene is a hypervalent iodine reagent that is used in conjunction with catalytic amount of sodium azide in acetonitrile, which enables oxidative decarboxylation of 2-aryl carboxylic acid into the corresponding aldehydes, ketones and nitriles.
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1. Names and Identifiers
- 1.1 Name
- (Diacetoxyiodo)benzene
- 1.2 Synonyms
(Diacetoxyiodo)benzene [Bis(acetoxy)iodo]benzene 1,2-Benzenediol, 3-iodo-, diacetate 3-Iodo-1,2-phenylene diacetate BAIB Benzene, (diacetoxyiodo)- Benzene, (dihydroxyiodo)-, diacetate Benzene, iodoso-, diacetate Bis(acetato)phenyliodine Bis(acetato-κO)phenyliodine Diacetoxy(phenyl)iodine diacetoxyiodobenzene diacetoxy-iodobenzene DIB Iodine, bis(acetato-O)phenyl- Iodine, bis(acetato-κO)phenyl- Iodobenzene diacetate Iodophenyl diacetate Iodosobenzene diacetate iodosylbenzene di(acetate) Iodosylbenzene diacetate NSC 226375 NSC 23801 Phenyliodine diacetate Phenyliodine(III) diacetate Phenyliodo diacetate Phenyliodonium diacetate Phenyliodoso acetate Phenyliodoso diacetate Phenyliodosyl diacetate PIA PIDA
- 1.3 CAS No.
- 3240-34-4
- 1.4 CID
- 76724
- 1.5 EINECS(EC#)
- 221-808-1
- 1.6 Molecular Formula
- C10H11IO4 (isomer)
- 1.7 Inchi
- InChI=1S/C10H11IO4/c1-8(12)14-11(15-9(2)13)10-6-4-3-5-7-10/h3-7H,1-2H3
- 1.8 InChkey
- ZBIKORITPGTTGI-UHFFFAOYSA-N
- 1.9 Canonical Smiles
- CC(=O)OI(C1=CC=CC=C1)OC(=O)C
- 1.10 Isomers Smiles
- CC(=O)OI(C1=CC=CC=C1)OC(=O)C
2. Properties
- 2.1 Density
- 1.6865 (estimate)
- 2.1 Melting point
- 161-163 °C(lit.)
- 2.1 Boiling point
- 456.8°C at 760 mmHg
- 2.1 Refractive index
- n/D 1.444
- 2.1 Flash Point
- 230.1°C
- 2.1 Precise Quality
- 321.97000
- 2.1 PSA
- 52.60000
- 2.1 logP
- 2.31880
- 2.1 Solubility
- INSOLUBLE
- 2.2 Appearance
- white to light yellow crystal powder
- 2.3 Storage
- Light Sensitive. Ambient temperatures.
- 2.4 Chemical Properties
- white to light yellow crystal powder
- 2.5 Color/Form
- Clear to cloudy colorless to yellow
- 2.6 Water Solubility
- H2O: INsoluble
- 2.7 Stability
- Stable at room temperature in closed containers under normal storage and handling conditions.
- 2.8 StorageTemp
- Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances. Store protected from light.
3. Use and Manufacturing
- 3.1 Methods of Manufacturing
- General procedure: In a typical experiment, a 20 ml scintillation vial was charged with glacial AcOH (2 ml), iodoarene (0.401 mmol) andCoCl2·6H2O (0.004 mmol, 1 molpercent) and was fitted with a rubber septum. The reaction vessel was purged with O2 for 5 min before acetaldehyde (4.07 mmol, 10.2 equiv.) was added in one portion. The reaction mixture was stirred under 1 atm O2, delivered by inflated balloon at 23 °C for 5 h. The solvent was removed in vacuo and the residuewasdissolved in CH2Cl2. The organic layer was washed with distilled water and extracted with CH2Cl2 (3 × 7 ml). The organic layer was dried over MgSO4 and solvent was removed in vacuo to afford the corresponding iodobenzene diacetate. The isolatedcompounds were characterized by 1H and 13C NMR spectroscopies.General procedure: The aromatic iodine compound (1, 2 or 3) (1 g) was dissolved in a mixed solution of acetic acid (3 mL) and acetic anhydride (3 mL)Under stirring at 45 to the solution was slowly added sodium borate (aromatic iodine molar amount of 10 times), maintaining the temperature constant reaction until the raw material disappears completely, about 4-6 hours, cooled to room temperature and water ( The mixture was filtered to give a white solid which was filtered to give a solid which was extracted three more times with ethyl acetate (20 mL). The organic phase was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a white solid which was combined with the previously filtered solid , And the crude product was washed with a mixed solution of acetone and petroleum ether in a volume ratio of 1: 1 to obtain the pure product (4, 5 or 6) as a white solid with the corresponding yields of 91percent, 86percent and 88percent, respectively.
- 3.2 Purification Methods
- The purity of diacetoxyiodobenzene can be checked by treatment with H2SO4 then KI and the liberated I2 is estimated with standard thiosulfate. It has been recrystallised from 5M acetic acid and dried overnight in a vacuum desiccator over CaCl2. The surface of the crystals may become slightly yellow but this does not affect its usefulness. [Sharefkin & Saltzman Org Synth Coll Vol V 600 1973, Beilstein 5 IV 693.] (Diacetoxyiodo)benzene Preparation Products And Raw materials Raw materials
- 3.3 Usage
- (Diacetoxyiodo)benzene is a hypervalent iodine reagent that is used in conjunction with catalytic amount of sodium azide in acetonitrile, which enables oxidative decarboxylation of 2-aryl carboxylic acid into the corresponding aldehydes, ketones and nitriles.
4. Safety and Handling
- 4.1 Hazard Codes
- Xi
- 4.1 Risk Statements
- 36/37/38
- 4.1 Safety Statements
- 22-24/25-37/39-26-36/37/39-27
- 4.1 Packing Group
- III
- 4.1 Hazard Class
- 6.1(b)
- 4.1 Hazard Declaration
- H302
- 4.1 RIDADR
- 1479
- 4.1 Caution Statement
- P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P322, P330, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501
- 4.1 WGK Germany
- 3
- 4.1 RTECS
- DA3525000
- 4.1 Report
-
Reported in EPA TSCA Inventory.
- 4.2 Safety
-
Poison by intravenous route. When heated to decomposition it emits toxic fumes of I?.
Safety Information of Iodobenzene diacetate (CAS NO.3240-34-4):
Hazard Codes:?
Xi
Risk Statements: 36/37/38?
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 22-24/25-37/39-26-36/37/39-27?
S22:Do not breathe dust.?
S24/25:Avoid contact with skin and eyes.?
S37/39:Wear suitable gloves and eye/face protection.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S27:Take off immediately all contaminated clothing.
RIDADR: 1479
WGK Germany: 3
RTECS: DA3525000
Hazard Note: Irritant
HazardClass: 6.1(b)
PackingGroup: III
- 4.3 Sensitive
- Light Sensitive
- 4.4 Specification
-
? Iodobenzene diacetate (CAS NO.3240-34-4), its Synonyms are (Diacetoxyiodo)benzene ; Benzene, (diacetoxyiodo)- ; Benzene, (dihydroxyiodo)-, diacetate ; Benzene, iodoso-, diacetate ; Bis(acetato)phenyliodine ; Phenyliodine diacetate ; Phenyliodine(III) diacetate ; Phenyliodo diacetate ; Phenyliodoso acetate ; Phenyliodoso diacetate ; Phenyliodosyl diacetate ; Iodine, bis(acetato-O)phenyl- (9CI) ; Iodine, bis(acetato-kappaO)phenyl- .
- 4.5 Toxicity
-
| Organism |
Test Type |
Route |
Reported Dose (Normalized Dose) |
Effect |
Source |
| mouse |
LD50 |
intravenous |
56mg/kg (56mg/kg) |
? |
U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02976, |
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Not classified.
2.2 GHS label elements, including precautionary statements
| Pictogram(s) | No symbol. |
| Signal word | No signal word. |
| Hazard statement(s) | none |
| Precautionary statement(s) | |
| Prevention | none |
| Response | none |
| Storage | none |
| Disposal | none |
2.3 Other hazards which do not result in classification
none
7. Synthesis Route
3240-34-4Total: 1 Synthesis Route
8. Other Information
- 8.0 Storage Conditions
- General procedure: In a typical experiment, a 20 ml scintillation vial was charged with glacial AcOH (2 ml), iodoarene (0.401 mmol) andCoCl2·6H2O (0.004 mmol, 1 molpercent) and was fitted with a rubber septum. The reaction vessel was purged with O2 for 5 min before acetaldehyde (4.07 mmol, 10.2 equiv.) was added in one portion. The reaction mixture was stirred under 1 atm O2, delivered by inflated balloon at 23 °C for 5 h. The solvent was removed in vacuo and the residuewasdissolved in CH2Cl2. The organic layer was washed with distilled water and extracted with CH2Cl2 (3 × 7 ml). The organic layer was dried over MgSO4 and solvent was removed in vacuo to afford the corresponding iodobenzene diacetate. The isolatedcompounds were characterized by 1H and 13C NMR spectroscopies.General procedure: The aromatic iodine compound (1, 2 or 3) (1 g) was dissolved in a mixed solution of acetic acid (3 mL) and acetic anhydride (3 mL)Under stirring at 45 to the solution was slowly added sodium borate (aromatic iodine molar amount of 10 times), maintaining the temperature constant reaction until the raw material disappears completely, about 4-6 hours, cooled to room temperature and water ( The mixture was filtered to give a white solid which was filtered to give a solid which was extracted three more times with ethyl acetate (20 mL). The organic phase was collected, dried over anhydrous MgSO4 and concentrated under reduced pressure to give a white solid which was combined with the previously filtered solid , And the crude product was washed with a mixed solution of acetone and petroleum ether in a volume ratio of 1: 1 to obtain the pure product (4, 5 or 6) as a white solid with the corresponding yields of 91percent, 86percent and 88percent, respectively.
- 8.1 Mesh Entry Terms
- ((diacetoxy)iodo)benzene
- 8.2 Manufacturing Info
- Iodine, bis(acetato-.kappa.O)phenyl-: ACTIVE
- 8.3 Usage
- Iodosobenzene is used as an oxidizing and acetoxylating agent in organic synthesis. It is actively involved in the preparation of (Z)-3,7-dimethyl-2,6-octadien-1-al(neral) from (Z)-3,7-dimethyl-2,6-octadien-1-ol (nerol) in presence of 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO). It is a useful reagent for the synthesis of a wide variety of heterocyclic compounds. It is also used in the Pd-catalyzed 2-arylation of indoles.
9. Computational chemical data
- Molecular Weight: 322.1g/mol
- Molecular Formula: C10H11IO4
- Compound Is Canonicalized: True
- XLogP3-AA: 2.8
- Exact Mass: 321.97021
- Monoisotopic Mass: 321.97021
- Complexity: 220
- Rotatable Bond Count: 5
- Hydrogen Bond Donor Count: 0
- Hydrogen Bond Acceptor Count: 4
- Topological Polar Surface Area: 52.6
- Heavy Atom Count: 15
- Defined Atom Stereocenter Count: 0
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBwOAAAAgAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAgAAAACACCkAAyCIAAAACIACDSCAACAAAgAAAIiAAAAIgIICKAERCAIAAggAAIiAcAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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