HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Compound

Cinnamoylbenzene

HCID 7189
New noteNew reactionRequest quotes
Print preview
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Substructure searchFind similar structures

Basic information

CAS
94-41-7
Standard SMILES
O=C(C=Cc1ccccc1)c1ccccc1
InChIKey
DQFBYFPFKXHELB-UHFFFAOYSA-N
Molecular formula
C15H12O
Average molar mass
208.25 g/mol
Monoisotopic mass
208.088815

Overview

cinnamoylbenzene has been reported in Alpinia hainanensis, Xanthorrhoea latifolia, and other organisms with data available.

Names & identifiers

Preferred name
Cinnamoylbenzene
IUPAC
1,3-diphenylprop-2-en-1-one
English name
Chalcone
Molecular formula
C15H12O
Molecular weight
208.26

Names & synonyms

CinnamoylbenzeneRefChem:1081887Phenyltrans-styrylketone2-Benzyliacetophenone, benzal-1,3-diphenyl-propenoneSCHEMBL27581orb1304682SCHEMBL3418546SCHEMBL3419029SCHEMBL8965816CHEMBL4777263
Show more names
(E)-CHALCONEBENZALACETOPHENONECHALKONE1,3-DIPHENYL-2-PROPENONE(E)-1,3-diphenylprop-2-en-1-oneChalcone, 96% (Benzylidenacetophenon)CHALCONEAI3-00946NSC 26612CCRIS 2213
SCHEMBL11076088HMS3371J111,3-di-phenyl-prop-2-en-1-ones5845NCI60_001320

Database identifiers

CAS
94-41-7
PubChem CID
7189
DTXSID
DTXSID8022531
ChEMBL
CHEMBL4777263

Properties

Computed structural properties

XLogP
3.1
Topological polar surface area
17.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
1
Rotatable bonds
3
Heavy atoms
16
Formal charge
0
Complexity
242

Experimental & physicochemical properties

SpringerMaterials PropertiesChemical shift
LogP3.62

Physicochemical properties

Melting point
55 · 55-59 °C
Boiling point
208 °C25 · 208 °C25 mm Hg(lit.)
Density
462 · d462 1.0712
refractive index
62 · nD62 1.6458
Flash point
230 °F · >230 °F
storage temp.
Sealed in dry,Room Temperature
solubility
1 g/10 · dioxane: soluble1g/10 mL, clear, colorless
form
Granular Powder
pka
-5.6 · -5.6
color
Yellow
Merck
14 · 14,2037
BRN
1210466 · 1210466
InChI

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
UD5576750
hs_code
29143900
risk_code
22-36/37
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xn,Xi
safety_code
22-36/37/39-45
Storage Class
11 - Combustible Solids
Hazard statements
H315-H302-H319-H335
Precautionary statements
P261-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313

Chemistry & industry

Applications · 3 items

DescriptionChalcone is the organic compound C6H5C(O)CH=CHC6H5. It is an α,β-unsaturated ketone. A variety of important biological compounds are known collectively as chalcones or chalconoids.They show antibacterial, antifungal, antitumor and anti-inflammatory properties. They are also intermediates in the biosynthesis of flavonoids, which are substances widespread in plants and with an array of biological activities. Chalcones are also intermediates in the Auwers synthesis of flavones.

Uses1,3-Diphenyl-2-propenone was used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines.

UsesChalcone is used in the preparation of pharmacologically-interesting heterocyclic systems like pyrazolines and pyrimidines. It also inhibits the proliferation of human breast cancer cell lines, MCF-7 and MDA-MB-231 by inducing apoptosis and blocking cell cycle progression in the G2/M phase.

Preparation methods · 1 item

PreparationChalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are known collectively as chalcones.Chalcones can be prepared by an aldol condensation between a benzaldehyde and an acetophenone in the presence of sodium hydroxide as a catalyst.This reaction has been found to work without any solvent at all - a solid-state reaction. The reaction between substituted benzaldehydes and acetophenones has been used to demonstrate green chemistry in undergraduate chemistry education.In a study investigating green chemistry synthesis, chalcones were also synthesized from the same starting materials in high temperature water (200 to 350 °C).

Upstream & downstream products

Upstream raw materials

Acetonetrans-Chalcone1-Butanone, 3-hydroxy-3-Methyl-1-phenyl-

Related reactions

140 records
New reaction record
HRID 11759 reaction equation
HRID 11759As productuspto-grants-2006_08
HRID 90287 reaction equation
HRID 90287As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 104720 reaction equation
HRID 104720As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 189509 reaction equation
HRID 189509As productTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 195377 reaction equation
HRID 195377As productTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 201793 reaction equation
HRID 201793As productTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 258942 reaction equation
HRID 258942As productAs reactantuspto-grants-1977_07
HRID 258945 reaction equation
HRID 258945As reactantuspto-grants-1977_07
Page 1 of 18

Compound notes

Loading…

On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
New noteNew reactionRequest quotes
InChI=1S/C15H12O/c16-15(14-9-5-2-6-10-14)12-11-13-7-3-1-4-8-13/h1-12H
InChIKey
DQFBYFPFKXHELB-UHFFFAOYSA-N
SMILES
C(C1=CC=CC=C1)(=O)C=CC1=CC=CC=C1
LogP
3.08 · 3.080
CAS DataBase Reference
94 · 94-41-7(CAS DataBase Reference)
FDA UNII
5 S5A2Q39HX · 5S5A2Q39HX
EPA Substance Registry System
2 · 2-Propen-1-one, 1,3-diphenyl- (94-41-7)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H302-H319-H335
Precautionary statements
261 · P261-P305+P351+P338-P264-P280-P302+P352+P332+P313+P362+P364-P305+P351+P338+P337+P313
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xn,Xi
Risk Statements
22 · 22-36/37
Safety Statements
22 · 22-36/37/39-45
WGK Germany
3 · 3
RTECS
5576750 · UD5576750
TSCA
TSCA listed
HS Code
29143900 · 29143900
Storage Class
11 · 11 - Combustible Solids
3-Benzenesulfonyl-1,3-diphenyl-propan-1-one
Iodobenzene
Acetophenone
Phenylacetylene
1-Phenyl-2-propen-1-one
Bromobenzene
1,3-Diphenyl-2-propyn-1-ol
Benzoyl chloride
Benzyl alcohol
Benzaldehyde

Downstream products

beta-Phenylpropiophenone2,4,6-Triphenylpyridine

Additional notes

DefinitionChEBI: A member of the class of chalcones that is acetophenone in which one of the methyl hydrogens has been replaced by a benzylidene group.