1,3-bis(4-bromophenyl)propane-1,3-dione CAS #: 33170-68-2; 凯望编码 (ChemWhat Code): 1490994

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名1,3-bis(4-bromophenyl)propane-1,3-dione
IUPAC Name33170-68-2
分子结构Structure of 1,3-bis(4-bromophenyl)propane-1,3-dione CAS 33170-68-2
CAS编号 33170-68-2
MDL NumberMFCD02668012
别名33170-68-2
1,3-Propanedione, 1,3-bis(4-bromophenyl)-
1,3-Di-(4-bromophenyl)-1,3-propanedione
DTXSID90186827
DTXCID30109318
1,3-bis(4-bromophenyl)propane-1,3-dione
1,3-Bis(4-bromophenyl)-1,3-propanedione
1,3-Bis[p-bromophenyl]-1,3-propanedione
SCHEMBL1305020
BBL040133
MFCD02668012
STK349912
AKOS000311272
4′-Bromo-2-(4-bromobenzoyl)acetophenone
AC-37983
1,3-bis(p-bromophenyl)propane-1,3-dione
CS-0268077
1,3-Bis(4-bromophenyl)-1,3-propanedione #
EN300-230034
分子式C15H10Br2O2
分子量382.05
InChIInChI=1S/C15H10Br2O2/c16-12-5-1-10(2-6-12)14(18)9-15(19)11-3-7-13(17)8-4-11/h1-8H,9H2
InChI KeyHOVMFCOUXZBNBX-UHFFFAOYSA-N
SMILESC1=CC(=CC=C1C(=O)CC(=O)C2=CC=C(C=C2)Br)Br  
Patent Information
Patent IDTitlePublication Date
CN115093323Beta-functionalized chiral homoallylic alcohol derivative as well as preparation method and application thereof2022
CN112679447Preparation method of polysubstituted thiazole-2(3H)-ketone compound2021
CN105348060Preparation method of 1,2-diketone derivative2016
CN105503945Method for preparing 2-phosphonic acid ester base-1, 3-dicarbonyl derivative2016
US2006/69288Process for preparing vinyl substituted beta-diketones2016

Physical Data

AppearanceWhite solid
Melting Point, °C Solvent (Melting Point)
198 – 200ethanol
191.5 – 194.5
183
185 – 186toluene
195 – 196ethanol
196 – 198benzene
197 – 198.5benzene

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)
Chemical shifts, Spectrum1Hchloroform-d1
Chemical shifts, Spectrum13Cchloroform-d1
Chemical shifts1Hdimethylsulfoxide-d6
Chemical shifts13Cdimethylsulfoxide-d6
Chemical shifts, Spectrum1Hchloroform-d1
Chemical shifts, Spectrum13Cchloroform-d1
DEPT (Distorsionless Enhancement by Polarisation Transfer), Spectrum13Cchloroform-d1
Description (IR Spectroscopy)Solvent (IR Spectroscopy)Comment (IR Spectroscopy)
Spectrumpotassium bromide
BandsKBr1600 cm**(-1)
SpectrumCHCl31750 – 1450 cm**(-1), der bei 194grad, 183grad und 167grad schmelzenden Formen.
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nm
SpectrumethanolRatio of solvents: 66percent350.8, 265.8
Spectrumdioxane220 – 380 nm, der bei 194grad, 183grad und 167grad schmelzenden Formen.

Route of Synthesis (ROS)

Route of Synthesis (ROS) of 1,3-bis(4-bromophenyl)propane-1,3-dione CAS 33170-68-2
Route of Synthesis (ROS) of 1,3-bis(4-bromophenyl)propane-1,3-dione CAS 33170-68-2
ConditionsYield
With palladium diacetate; triethylamine; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at 100℃; under 15514.4 Torr; for 12h; Heck coupling;62%
With triethylamine; palladium diacetate; tris-(o-tolyl)phosphine In N,N-dimethyl-formamide at -196 – 100℃; under 15514.9 Torr; for 12.3333h;

Experimental Procedure
2.4
Step 4 Synthesis of 4,4′-divinyldibenzoylmethane: Dimethyl formamide (30 mL), palladium acetate (0.022 g, 0.1 mmol), tri-o-tolyl phosphine (0.060 g, 0.2 mmol), triethylamine (9.1 g, 90 mmol), 4,4′-dibromodibenzoylmethane (3.82 g, 10 mmol) were added to a 100 mL Parr high pressure reactor with an inner glass liner. The solution was degassed with nitrogen for 10 minutes before the reactor was cooled to -196° C. and ethylene (1.7 g, 61 mmol) was condensed for 20 minutes. The reactor was allowed to warm to room temperature before heating to 100° C. in an oil bath. The pressure was bled off until 300 psi was achieved and the reaction was allowed to proceed for 12 hours. The reaction vessel was cooled to room temperature, the extra pressure bled, and the contents dissolved in water (50 mL) and ether (50 mL). The aqueous phase was made acidic by addition of concentrated hydrochloric acid followed by extraction with ether (2*50 mL). The combined organic phase was rinsed with saturated sodium chloride solution, and the organic phase was dried over magnesium sulfate overnight. The solution was filtered, the solvent was removed by vacuum, and the residue dissolved in chloroform (3 mL). The product was isolated by column chromatography from silica gel (Selecto, mesh size 63 – 200) with chloroform as eluent. The first band collected resulted in a yellow powder (1.70 g, 62% yield) upon solvent removal. 1H-NMR (200 MHz, 25° C., CDCl3): δ 16.20 (s, 1 H), 8.00 (d, 4 H), 7.55 (d, 4 H), 6.80 (dd, 2 H), 6.70 (s, 1 H), 5.90 (d, 2 H), 5.40 (d, 2 H).		62%

Safety and Hazards

Pictogram(s)exclamation-markenvironment
SignalWarning
GHS Hazard StatementsH319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]
H410 (100%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
Precautionary Statement CodesP264+P265, P273, P280, P305+P351+P338, P337+P317, P391, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)

Other Data

TransportationUnder room temperature away from light
HS Code
StorageUnder room temperature away from light
Shelf Life1 year
Druglikeness
Lipinski rules component
分子量382.051
logP5.255
HBA2
HBD0
Matching Lipinski Rules3
Veber rules component
Polar Surface Area (PSA)34.14
Rotatable Bond (RotB)4
Matching Veber Rules2
Use Pattern
3-Aminopyridine CAS#: 462-08-8 is an intermediate in pesticides and dyes; pesticide raw materials; analytical reagents.

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