4-NITROCINNAMALDEHYDE Chemical Properties

Melting point:

140-143 °C(lit.)

Boiling point:

309.06°C (rough estimate)

Density 

1.3312 (rough estimate)

refractive index 

1.5200 (estimate)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

crystals

Appearance

Yellow to brown Solid

Water Solubility 

Insoluble in water.

Sensitive 

Air Sensitive

BRN 

1565424

InChI

1S/C9H7NO3/c11-7-1-2-8-3-5-9(6-4-8)10(12)13/h1-7H/b2-1+

InChIKey

ALGQVMMYDWQDEC-OWOJBTEDSA-N

SMILES

[O-][N+](=O)c1ccc(\C=C\C=O)cc1

CAS DataBase Reference

1734-79-8(CAS DataBase Reference)

EPA Substance Registry System

2-Propenal, 3-(4-nitrophenyl)- (1734-79-8)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/38

Safety Statements 

26-36

WGK Germany 

3

RTECS 

GD6650000

TSCA 

TSCA listed

HS Code 

29130000

Storage Class

11 - Combustible Solids

Hazard Classifications

Eye Irrit. 2
Skin Irrit. 2

MSDS

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

4-NITROCINNAMALDEHYDE Usage And Synthesis

Chemical Properties

beige to yellow-brown crystals or cryst. powder

Uses

Doebner-Miller reaction the 4- nitrocinnamaldehyde and 2-methylaniline in concentrated HC1 give the corresponding 8-methyl-2-phenylquinoline (3: R = 4'-N02) directly. The asymmetric Friedel-Crafts-type alkylation in aqueous media reaction of 4-Nitrocinnamaldehydr with N-methyl indole using trifluoroacetic acid (TFA) salt of the PEG-PS-supported prolyl peptide having the polyleucine tether as a catalyst. 4-Nitrocinnamaldehyde has been used in the preparation of 2, 2?-[(E)-3-(4-nitrophenyl) prop-2-ene-1,1-diyl] bis(3-hydroxy-5, 5-dimethylcyclohex-2-en-1-one).

Synthesis

5.0 g (66 mmol) of p-nitrobenzaldehyde and 10.0 mL of acetaldehyde were added to a three-necked flask, and to a dropping funnel was added 10 mL of 30% mass fraction potassium hydroxide-methanol solution with magnetic stirring, and the reaction flask was cooled with an ice-salt bath, and when the temperature was reduced to 0-5??C, 5 mL of potassium hydroxide-methanol solution was added slowly and dropwise with magnetic stirring, and the reaction was carried out for 40 min, and then 5 mL of potassium hydroxide-methano was added dropwise. Alcohol solution, continue the reaction for 40min at about 10??C, cool the reaction mixture below 5??C to solidify, add 16mL of acetic anhydride and Heated on a water bath for 30min, poured into 120mL of hot water, added 16mL of concentrated hydrochloric acid, heated on a water bath for 20min, and left to stand for 24h. Dialyzed crystals, pumped, washed, and recrystallized in aqueous acetic acid with a mass fraction of 30% to obtain 1.6g of yellow crystals, which is 4-nitrocinnamaldehyde, and the calculated product yield was 45.3%.

4-NITROCINNAMALDEHYDE(1734-79-8)Related Product Information

• 4-Nitrocinnamic acid
• Ethyl 4-nitrocinnamate
• 4-NITROCHALCONE
• 4-NITROCINNAMALDEHYDE
• DIMETHYL (4-NITROBENZYLIDENE)MALONATE
• 2-NITROCINNAMALDEHYDE
• 4-nitrocinnamaldehyde, predominantly trans,TRANS-4-NITROCINNAMALDEHYDE,P-NITROCINNAMALDEHYDE,4-NITROCINNAMALDEHYDE
• Cinnamaldehyde
• ALPHA-CARBOXY-4-BROMO-4'-NITRO STILBENE
• TRANS-4-NITROCINNAMOYL CHLORIDE
• METHYL 4-NITROCINNAMATE
• ETHYL 2-CYANO-3-(4-NITROPHENYL)PROP-2-ENOATE
• 5-[1-(4-NITRO-PHENYL)-METH-(Z)-YLIDENE]-2-THIOXO-THIAZOLIDIN-4-ONE
• 2-NITROCINNAMALDEHYDE,TRANS-2-NITROCINNAMALDEHYDE,O-NITROCINNAMALDEHYDE,2'-NITROCINNAMALDEHYDE
• 3-NITROCINNAMALDEHYDE,M-NITROCINNAMALDEHYDE
• 1-[2-(METHOXYMETHOXY)PHENYL]-3-(4-NITROPHENYL)PROP-2-EN-1-ONE
• RARECHEM AL BM 0193
• 2-[3-(4-NITROPHENYL)ACRYLOYL]PHENYL 4-METHYLBENZENE-1-SULFONATE