4-(Dimethylamino)cinnamaldehyde Chemical Properties

Melting point:

138-140 °C(lit.)

Boiling point:

306.53°C (rough estimate)

Density 

1.0582 (rough estimate)

refractive index 

1.5260 (estimate)

storage temp. 

-20°C

solubility 

dioxane: 50 mg/mL, clear

pka

4.59±0.24(Predicted)

form 

Powder

color 

Yellow to orange

Sensitive 

Air & Light Sensitive

BRN 

972369

Stability:

Stable. Incompatible with strong oxidizing agents, strong bases.

Major Application

diagnostic assay manufacturing
hematology
histology

InChI

1S/C11H13NO/c1-12(2)11-7-5-10(6-8-11)4-3-9-13/h3-9H,1-2H3/b4-3+

InChIKey

RUKJCCIJLIMGEP-ONEGZZNKSA-N

SMILES

CN(C)c1ccc(\C=C\C=O)cc1

LogP

2.630 (est)

CAS DataBase Reference

6203-18-5(CAS DataBase Reference)

NIST Chemistry Reference

2-Propenal, 3-[4-(dimethylamino)phenyl]-(6203-18-5)

EPA Substance Registry System

2-Propenal, 3-[4-(dimethylamino)phenyl]- (6203-18-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

UN 1789 8/PG 3

WGK Germany 

3

F 

8-10-23

TSCA 

TSCA listed

HS Code 

29124990

Storage Class

11 - Combustible Solids

Hazard Classifications

Aquatic Chronic 2
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-(Dimethylamino)cinnamaldehyde Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

4-(Dimethylamino)cinnamaldehyde is a reagent used in the assay of apotryptophanase and tryptophanase. It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder.

Uses

Used to determine the ability of an organism to split indole from the tryptophan molecule.

Uses

4-(Dimethylamino)cinnamaldehyde is a reagent for assay of indole product of apotryptophanase and tryptophanase. It has been used in a chromogenic method for quantifying proanthocyandines in cranberry powder.

Definition

ChEBI: 4-dimethylaminocinnamaldehyde is a member of cinnamaldehydes.

General Description

DMACA is basically a selective staining reagent. It helps identify the flavanols by staining them blue in color.

Biochem/physiol Actions

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

Synthesis

General procedure for the synthesis of (E)-3-(4-(dimethylamino)phenyl)acrolein from acetaldehyde and p-dimethylaminobenzaldehyde: A mixture of 4-N,N-dimethylaminobenzaldehyde (5.00 g, 34 mmol) with 25 ml of concentrated sulfuric acid was cooled to 0°C. Subsequently, 1 ml of distilled water was slowly added. Keeping the reaction mixture at 0°C, acetaldehyde (5.6 ml, 102 mmol) was added dropwise, ensuring that the reaction temperature did not exceed 2°C. After the dropwise addition, the dark reaction mixture was continued to be stirred at 0°C for 0.5 hours. Subsequently, the reaction mixture was poured into ice water and neutralized with 10% NaOH solution to pH 7. The resulting brown solution was filtered and the crude product was washed with distilled water and crystallized twice by ethanol to give a final orange solid product. The yield was 56% and the melting point was 134-136 °C. The product was analyzed by FT-IR (KBr, cm^-1 ) showing characteristic peaks: 2921, 2801, 2738, 1662, 1599, 1527, 1456, 1373. 1H NMR (300 MHz, CDCl3, ppm) data were as follows: δ 9.62 (1H, d, J=7.5 Hz), 7.48 (2H, d, J=7.5 Hz), 7.41 (1H, d, J=13.1 Hz), 6.71 (2H, d, J=7.5 Hz), 6.57 (1H, dd, J=7.5 Hz, 13.1 Hz), 3.08 (6H, s). Mass spectrometry (MS) analysis showed the molecular ion peak m/z: 176.2 (M+), consistent with the molecular formula C11H13NO.

Purification Methods

The aldehyde crystallises from EtOH or ligroin and is dried in vacuo. The oxime has m 157o (from ligroin). The phenylhydrazone has m 169o (form MeOH). It is used as a reagent for amines (with NH3, UV has max at 630nm). [K.nig et al. Chem Ber 61 2075 2075, Quareshi & Kahn Anal Chim Acta 86 309 1976, Beilstein 14 III 184, 14 IV 197.]

References

[1] Dyes and Pigments, 2017, vol. 139, p. 820 - 830
[2] Chemical and Pharmaceutical Bulletin, 1998, vol. 46, # 8, p. 1254 - 1260
[3] Bioorganic and Medicinal Chemistry Letters, 2017, vol. 27, # 8, p. 1803 - 1807

4-(Dimethylamino)cinnamaldehyde(6203-18-5)Related Product Information

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