Basic information
- CAS
15656-28-7- Standard SMILES
F[B-](F)(F)F.[IH2+].c1ccncc1.c1ccncc1- InChIKey
WVXJCTSZJWIBQT-UHFFFAOYSA-N- Molecular formula
- C10H12BF4IN2
- Average molar mass
- 373.93 g/mol
- Monoisotopic mass
- 374.00744
Names & identifiers
- Preferred name
- Bis(pyridine)iodonium tetrafluoroborate
- IUPAC
- iodanium;bis(pyridine);tetrafluoroborate
- English name
- Bis(pyridine)iodonium tetrafluoroborate
- Molecular formula
- C10H10BF4IN2
- Molecular weight
- 371.91
Names & synonyms
Bis(pyridine)iodonium tetrafluoroborate15656-28-7DTXSID50447027Barluenga reagentBis(pyridine)iodinium tetrafluoroborateBis(pyridine)iodine(I) tetrafluoroborateRefChem:569268Bis(pyridine)iodonium tetrafluoroborate [MI]DTXCID2039784896046808SX628-405-3Iodine(1+), bis(pyridine)-, tetrafluoroborate(1-) (1:1)
Show more names
BarluengasBARLUENGA'S REAGENTSKL215iodaniumBarluengaReagentIpy2Bf4Barluenga’S Reagent Ipy2Bf4iodonium pyridine tetrafluoroborateIodanium pyridine tetrafluoroborate
MFCD03703393iodanium;pyridine;tetrafluoroborateBis(pyridine)iodonium tetrafluoroborate [Barluenga's Reagent]IPy2BF4SCHEMBL756401C10H10BF4IN2C10H12BF4IN2SCHEMBL4590747
Database identifiers
- CAS
15656-28-7- PubChem CID
- 10883201
- DTXSID
DTXSID50447027- EC Number
- 628-405-3
Properties
Computed structural properties
- Topological polar surface area
- 25.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 50
Physicochemical properties
- Melting point
- 137 · 137-141 °C (lit.)
- storage temp.
- 2 · 2-8°C
- solubility
- 2 Cl2, · sol CH2Cl2, DMSO, MeCN, pyridine, DMF; modestly sol CHCl3; insol ether, THF, hexane
- form
- Powder
- color
- Yellow
- Water Solubility
- Hydrolyzes in water.
- Sensitive
- Moisture & Light Sensitive
- Merck
- 14 · 14,1302
- BRN
- 4284739 · 4284739
- InChI
- 1S/2C5H5N.BF4.I/c2*1-2-4-6-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1
- InChIKey
- JBVUIHBKNVHCKK-UHFFFAOYSA-N
- SMILES
- [I+].F[B-](F)(F)F.c1ccncc1.c2ccncc2
- CAS DataBase Reference
- 15656 · 15656-28-7(CAS DataBase Reference)
- FDA UNII
- 96046808 SX · 96046808SX
- UNSPSC Code
- 12352005 · 12352005
- NACRES
- 22 · NA.22
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319-H335
- Precautionary statements
- 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
- target organs
- Respiratory system
- PPE
- 95 · dust mask type N95 (US), Eyeshields, Gloves
- Hazard Codes
- Xi,T
- Risk Statements
- 36 · 36/37/38
- Safety Statements
- 26 · 26-36-37/39
- RIDADR
- 1759 · 1759
- WGK Germany
- 3 · 3
- Hazard Note
- Toxic/Irritant
- HazardClass
- MOISTURE SENSITIVE, KEEP COLD, LIGHT SENSITIVE
- PackingGroup
- II
- HS Code
- 29333990 · 29333990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3
Safety & regulation
GHS classification
GHS Classification
Warning
H315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (97.8%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (97.8%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 45 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (97.8%)；Eye Irrit. 2 (97.8%)；STOT SE 3 (97.8%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
- ridadr
- 1759
- hs_code
- 29333990
- risk_code
- 36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi,T
- hazard_note
- Toxic/Irritant
- safety_code
- 26-36-37/39
- hazard_class
- MOISTURE SENSITIVE, KEEP COLD, LIGHT SENSITIVE
- Storage Class
- 11 - Combustible Solids
- packing_group
- II
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionBis(pyridine)iodonium tetrafluoroborate is iodinating agent for the selective functionalization of unsaturated compounds; can also mediate C-C bond formation.
UsesBis(pyridine)iodonium tetrafluoroborate is used as mild iodinating and oxidizing reagent. It is also useful for selective iodination of free phenolic groups in tyrosine residues during solid-phase synthesis.
Preparation methods
PreparationBis(pyridine)iodonium tetrafluoroborate is prepared by the reaction of HgO/HBF4-SiO2 with iodine and pyridine in dry CH2Cl2 at rt. Solids are filtered off, and the reagent is isolated by precipitation from CH2Cl2 solution by addition of cold ether, repeating the operation several times until a negative test for mercury(II) is obtained (i.e. absence of precipitation of mercury by treatment of an aliquot with NaBH4/NaOH).
Upstream & downstream products
Upstream raw materials
Suppliers57 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
Hebei Chuanghai Biotechnology Co., Ltd+86-17732866630 · [email protected]
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Related reactions
32 records
Compound notes
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