ChemicalBook--->CAS DataBase List--->2113-51-1

2113-51-1

2113-51-1 Structure

2113-51-1 Structure
IdentificationMore
[Name]

2-Iodobiphenyl
[CAS]

2113-51-1
[Synonyms]

2-IODOBIPHENYL
O-IODODIPHENYL
2-iodo-1,1’-biphenyl
2-Iodo-1,1'-biphenyl
2-iodo-1’-biphenyl
2-iodo-bipheny
Biphenyl, 2-iodo-
o-Iodobiphenyl
o-Phenyliodobenzene
2-IODOBIPHENYL TECH
[EINECS(EC#)]

218-303-3
[Molecular Formula]

C12H9I
[MDL Number]

MFCD00039396
[Molecular Weight]

280.1
[MOL File]

2113-51-1.mol
Questions And AnswerBack Directory
[Synthesis]

Synthetic route of 2-iodobiphenyl

1) Preparation of [1,1'-biphenyl]-2-amine (1a-1):

To an ethanol solution (500 ml) of phenylboronic acid (12.36 g, 109.58 mmol), o-iodoaniline (20.00 g, 91.31 mmol), K3PO4 (48.46 g, 228.29 mmol), and Pd(PPh3)4 (1.06 g, 0.91 mmol) were added. The reaction solution was reacted under argon protection for 6 hours, and then the ethanol was removed under reduced pressure.

The residue was dissolved in ethyl acetate, washed once with water and once with saturated brine, dried over anhydrous sodium sulfate, filtered, and the solvent was removed under reduced pressure. The residue was then subjected to silica gel column chromatography (elution buffer volume ratio, petroleum ether:ethyl acetate = 20:1-10:1) to give a yellow solid 1a-1 (14.68 g, 95% yield).

2) Preparation of 2-iodobiphenyl (1a-2):

Add 221.7 ml of 4 M hydrochloric acid aqueous solution to a tetrahydrofuran solution (280 ml) of 1a-1. After stirring for 20 minutes, add dropwise 20 ml of an aqueous solution of sodium nitrite (9.17 g, 132.96 mmol) under an ice-water bath. After stirring for 30 minutes, add dropwise 20 ml of an aqueous solution of potassium iodide (36.79 g, 221.16 mmol) under an ice-water bath. After stirring for 30 minutes, slowly raise the solution to room temperature and stir for another hour.

Finally, add 1M sodium thiosulfate solution dropwise until the reaction solution remains colorless. Separate the layers, extract the aqueous phase with ethyl acetate (100 mL × 3). Combine the organic phases, wash successively with water (50 mL × 2) and saturated brine (50 mL × 1), dry with anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure.
Chemical PropertiesBack Directory
[Appearance]

clear colorless to yellow liquid
[Melting point ]

55-57 °C
[Boiling point ]

300 °C (lit.)
[density ]

1.59 g/mL at 25 °C(lit.)
[refractive index ]

n20/D 1.662(lit.)
[Fp ]

>230 °F
[storage temp. ]

Keep in dark place,Sealed in dry,Room Temperature
[form ]

Liquid
[color ]

Clear colorless to yellow
[Water Solubility ]

Insoluble in water.
[Sensitive ]

Light Sensitive
[BRN ]

2206820
[InChI]

1S/C12H9I/c13-12-9-5-4-8-11(12)10-6-2-1-3-7-10/h1-9H
[InChIKey]

QFUYDAGNUJWBSM-UHFFFAOYSA-N
[SMILES]

Ic1ccccc1-c2ccccc2
[CAS DataBase Reference]

2113-51-1(CAS DataBase Reference)
[NIST Chemistry Reference]

1,1'-Biphenyl, 2-iodo-(2113-51-1)
[EPA Substance Registry System]

2113-51-1(EPA Substance)
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H315-H319-H227
[Precautionary statements ]

P501-P210-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313-P403+P235
[Hazard Codes ]

Xi,T
[Risk Statements ]

R36/37/38:Irritating to eyes, respiratory system and skin .
R63:Possible risk of harm to the unborn child.
R42/43:May cause sensitization by inhalation and skin contact .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) .
[WGK Germany ]

3
[RTECS ]

DV5384800
[TSCA ]

Yes
[HS Code ]

29039990
[Storage Class]

10 - Combustible liquids
Hazard InformationBack Directory
[Chemical Properties]

clear colorless to yellow liquid
[Uses]

2-Iodobiphenyl is used as an organic chemical synthesis intermediate.
[General Description]

2-Iodobiphenyl is an ortho-halogenated biphenyl that can be synthesized from 2-aminobiphenyl.
Spectrum DetailBack Directory
[Spectrum Detail]

2-Iodobiphenyl(2113-51-1)MS
2-Iodobiphenyl(2113-51-1)1HNMR
2-Iodobiphenyl(2113-51-1)13CNMR
2-Iodobiphenyl(2113-51-1)IR1
Well-known Reagent Company Product InformationBack Directory
[Acros Organics]

2-Iodobiphenyl, 98%(2113-51-1)
[Alfa Aesar]

2-Iodobiphenyl, 98%(2113-51-1)
[Sigma Aldrich]

2113-51-1(sigmaaldrich)
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