3-[4-(dimethylamino)phenyl]prop-2-enal

• ChemBase ID: 78055
• Molecular Formular: C11H13NO
• Molecular Mass: 175.22702
• Monoisotopic Mass: 175.09971404
• SMILES: N(c1ccc(cc1)/C=C/C=O)(C)C
• Canonical SMILES: O=C/C=C/c1ccc(cc1)N(C)C
• InChI: InChI=1S/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3
• InChIKey: RUKJCCIJLIMGEP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[4-(dimethylamino)phenyl]prop-2-enal; (2E)-3-[4-(dimethylamino)phenyl]prop-2-enal
• IUPAC Traditional name: dmaca reagent
• Synonyms: DMACA; 4-(Dimethylamino)cinnamaldehyde; DMAC; 4-Dimethylaminocinnamaldehyde; p-Dimethylaminocinnamaldehyde; DMACA reagent; P-N,N-DIMETHYLAMINOCINNAMALDEHYDE; 3-[4-(Dimethylamino)phenyl]prop-2-enal; N,N-Dimethyl-4-(3-oxoprop-1-en-1-yl)aniline; 4-(Dimethylamino)cinnamaldehyde; 4-(Dimethylamino)-cinnamaldehyde solution; DMACA Reagent; 4-(Dimethylamino)cinnamaldehyde; p-DIMETHYLAMINOCINNAMALDEHYDE; 3-(4-(Dimethylamino)phenyl)acrylaldehyde; 4-Dimethylaminocinnamaldehyde; 4-二甲氨基肉桂醛

Database IDs

• CAS Number: 6203-18-5
• EC Number: 228-267-0
• MDL Number: MFCD00007002
• Beilstein Number: 972369; 2208002
• PubChem SID: 24864579; 24873183; 24893878; 162042889
• PubChem CID: 5284506
• Chemspider ID: 4447567
• MeSH Name: 4-Dimethylaminocinnamaldehyde
• Wikipedia Title: DMACA_reagent

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 2.0152733
• LogD (pH = 7.4): 2.084555
• Log P: 2.0855138
• Molar Refractivity: 56.5631 cm^3
• Polarizability: 20.591461 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: chloroform/ethanol (1:1): soluble50 mg/mL, clear to very faintly turbid, yellow to deep red; dioxane, 50 g/L in water
• Apperance: white to light yellow crystal powder
• Melting Point: 135-137°C; 137-144°C; 138°C; 138-140 °C(lit.); 138-140°C; 138-141 °C
• Boiling Point: 329°C
• Density: 1.057 g/mL

Safety Information

• Storage Condition: Room Temperature (15-30°C)
• Storage Warning: Air & Light Sensitive; Irritant/Air Sensitive/Light Sensitive/Store at -20°C/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• UN Number: 1789
• German water hazard class: 2; 3
• Hazard Class: 8
• Packing Group: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• TSCA Listed: 是
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Faceshields, Gloves, Goggles
• RID/ADR: UN 1789 8/PG 3
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC); 95+%; 98%
• Grade: for microbiology; purum
• Linear Formula: (CH3)2NC6H4CH=CHCHO
• Empirical Formula (Hill Notation): C11H13NO

DETAILS

MP Biomedicals - 05209178

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02150933

Crystalline
Reagent for detection of indole derivatives, particularly the assay of tryptophanase and apotryptophanase.
Turner, J.M., Biochem. J. , 78 : 790 (1961).

Sigma Aldrich - D4506

Application
Reagent for assay of indole product of apotryptophanase and tryptophanase.1 DMAC produces colored adducts with flavanols for subsequent HPLC.2,3 It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder.4,5

Sigma Aldrich - 49825

Components
Composition per 100 ml:Dimethylaminocinnamaldehye 1 gHydrochloric acid (concentrated) 1.0 mldistilled water 99.0 ml
Application
Used to determine the ability of an organism to split indole from the tryptophan molecule.
Other Notes
Reagent for the rapid identification of Streptococci.1,2

Sigma Aldrich - 39421

Other Notes
Reagent for the determination of aromatic amines2; e.g. PABA1