| Identification | More | [Name]
Ethyl 4-iodobenzoate | [CAS]
51934-41-9 | [Synonyms]
4-IODOBENZOIC ACID ETHYL ESTER
ETHYL 4-IODOBENZOATE
ETHYL P-IODOBENZOATE
IBE
LABOTEST-BB LT01148245
RARECHEM AL BI 0710
p-Iodobenzoic acid ethyl ester
ETHY1-4-IODOBENZOATE
Ethyl-4-Iodobenzoate95%
Ethyl-4-zodabenzoate
ETHYL 4-IODOBENZENE
4-IODOBENZONIC ACID ETHYL ESTER
Ethyl 4-iodobenzoate ,97%
4-Iodobenzoic acid ethyl | [EINECS(EC#)]
429-550-3 | [Molecular Formula]
C9H9IO2 | [MDL Number]
MFCD00017344 | [Molecular Weight]
276.07 | [MOL File]
51934-41-9.mol |
| Chemical Properties | Back Directory | [Appearance]
Light Yellow Oil | [Melting point ]
267 °C | [Boiling point ]
281-283 °C | [density ]
1.641 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.5880(lit.)
| [Fp ]
>230 °F
| [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
Chloroform, Dichloromethane, Ethyl Acetate, Hexane | [form ]
Liquid | [color ]
Clear colorless to yellow | [Specific Gravity]
1.66 | [Water Solubility ]
insoluble | [Sensitive ]
Light Sensitive | [Detection Methods]
GC,NMR | [BRN ]
2208568 | [InChI]
1S/C9H9IO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2H2,1H3 | [InChIKey]
YCBJOQUNPLTBGG-UHFFFAOYSA-N | [SMILES]
CCOC(=O)c1ccc(I)cc1 | [CAS DataBase Reference]
51934-41-9(CAS DataBase Reference) | [NIST Chemistry Reference]
Ethyl 4-iodobenzoate(51934-41-9) | [Storage Precautions]
Light sensitive |
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319 | [Precautionary statements ]
P264-P280a-P321-P332+P313-P337+P313-P305+P351+P338 | [Hazard Codes ]
N,Xi,C | [Risk Statements ]
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3082 9/PG 3
| [WGK Germany ]
3
| [F ]
8 | [Hazard Note ]
Irritant | [REACH Registrations]
Inactive | [HazardClass ]
IRRITANT, LIGHT SENSITIVE | [HS Code ]
29163990 | [Storage Class]
10 - Combustible liquids |
| Hazard Information | Back Directory | [Chemical Properties]
Light Yellow Oil | [Uses]
Ethyl 4-iodobenzoate can be used in the synthesis of biphenyl derivatives via Negishi cross coupling with the intermediates of the type ArMg(tmp)·2LiCl (tmp = trimethylolpropane). It can also be used as a starting material in the synthesis of p-carbomethoxyphenylmagnesium bromide, a polyfunctional organometallic reagent that can be used as building block in the synthesis of complex target molecules. | [Synthesis]
General procedure for the synthesis of ethyl p-iodobenzoate from ethyl 4-bromobenzoate: under nitrogen protection, Cu2O (7.2 mg, 10 mol%), L-proline (11.5 mg, 20 mol%), ethyl 4-bromobenzoate (0.50 mmol), potassium iodide (KI, 249 mg, 0.75 mmol) and ethanol (EtOH, 1.5 mL). After sealing the Schlenk tube with a PTFE valve, the reaction mixture was stirred at 110 °C and the reaction process was monitored by gas chromatography (GC) analysis. Upon completion of the reaction, the yield was determined by GC using an appropriate internal standard (e.g., chlorobenzene or 1-chloro-4-methylbenzene) for highly volatile products; or the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography (eluent ratio of petroleum ether/ethyl acetate = 10/1) to obtain the target product ethyl p-iodobenzoate. | [References]
[1] Catalysis Today, 2016, vol. 274, p. 129 - 132
[2] Chemical Communications, 2012, vol. 48, # 33, p. 3993 - 3995
[3] Angewandte Chemie - International Edition, 2015, vol. 54, # 1, p. 263 - 266
[4] Angew. Chem., 2015, vol. 127, # 01, p. 265 - 268,4
[5] Catalysis Science and Technology, 2017, vol. 7, # 10, p. 2110 - 2117 |
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