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Cas Database

1734-79-8

1734-79-8

Identification

  • Product Name:2-Propenal,3-(4-nitrophenyl)-

  • CAS Number: 1734-79-8

  • EINECS:217-076-8

  • Molecular Weight:177.159

  • Molecular Formula: C9H7NO3

  • HS Code:29130000

  • Mol File:1734-79-8.mol

Synonyms:Cinnamaldehyde,p-nitro- (6CI,7CI,8CI);3-(4-Nitrophenyl)-2-propenal;4-Nitrocinnamic aldehyde;NSC 1318;p-Nitrocinnamaldehyde;

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Safety information and MSDS view more

  • Pictogram(s):IrritantXi

  • Hazard Codes:Xi

  • Signal Word:Warning

  • Hazard Statement:H315 Causes skin irritationH319 Causes serious eye irritation

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

Supplier and reference price

  • Manufacture/Brand
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  • Manufacture/Brand:TCI Chemical
  • Product Description:4-Nitrocinnamaldehyde >98.0%(GC)
  • Packaging:5g
  • Price:$ 96
  • Delivery:In stock
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  • Manufacture/Brand:Sigma-Aldrich
  • Product Description:trans-4-Nitrocinnamaldehyde technical, ≥97.0% (T)
  • Packaging:5g
  • Price:$ 181
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:trans-4-Nitrocinnamaldehyde 98%
  • Packaging:1g
  • Price:$ 36
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  • Manufacture/Brand:Frontier Specialty Chemicals
  • Product Description:trans-4-Nitrocinnamaldehyde 98%
  • Packaging:5g
  • Price:$ 143
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  • Manufacture/Brand:Crysdot
  • Product Description:3-(4-Nitrophenyl)acrylaldehyde 97%
  • Packaging:25g
  • Price:$ 194
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  • Manufacture/Brand:Chemenu
  • Product Description:3-(4-Nitrophenyl)acrylaldehyde 95%
  • Packaging:10g
  • Price:$ 138
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  • Manufacture/Brand:Ambeed
  • Product Description:3-(4-Nitrophenyl)acrylaldehyde 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:3-(4-Nitrophenyl)acrylaldehyde 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:3-(4-Nitrophenyl)acrylaldehyde 98%
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  • Manufacture/Brand:Ambeed
  • Product Description:3-(4-Nitrophenyl)acrylaldehyde 98%
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Relevant articles and documentsAll total 49 Articles be found

Efficient catalytic activity of transition metal ions in Vilsmeier-Haack reactions with acetophenones

Aneesa,Rajanna,Venkateswarlu,Reddy, K. Rajendar,Kumar, Y. Arun

, p. 721 - 733 (2013)

Vilsmeier-Haack (VH) formylation reactions with acetophenones are sluggish in acetonitrile medium even at elevated temperatures. However, millimolar concentrations of transition metal ions such as Cu(II), Ni(II), Co(II), and Cd(II) were found to exhibit efficient catalytic activity in Vilsmeier-Haack Reactions with acetophenones. Reactions are accelerated remarkably in the presence of transition metal ions. The VH reactions followed second order kinetics and afforded acetyl derivatives under kinetic conditions also irrespective of the nature of oxychloride (POCl3 or SOCl2) used for the preparation of VH reagent along with DMF. On the basis of UV-vis spectroscopic studies and kinetic observations, participation of a ternary precursor [M(II) S (VHR)] in the rate-limiting step has been proposed to explain the mechanism of the metal ion-catalyzed VH reaction.

Asymmetric Synthesis of Functionalized 9-Methyldecalins Using a Diphenylprolinol-Silyl-Ether-Mediated Domino Michael/Aldol Reaction

Hayashi, Yujiro,Salazar, Hugo A.,Koshino, Seitaro

, p. 6654 - 6658 (2021/09/11)

Substituted 9-methyldecalin derivatives containing an all carbon quaternary chiral center were synthesized with excellent enantioselectivity via an organocatalyst-mediated domino reaction. The first reaction is a diphenylprolinol silyl ether-mediated Michael reaction, and the second reaction is an intramolecular aldol reaction. The enantiomerically pure catalyst is involved in both reactions.

Enantioselective Organocatalytic Synthesis of 1,2,3-Trisubstituted Cyclopentanes

?otolová, Martina,Kamlar, Martin,Reme?, Marek,Géant, Pierre-Yves,Císa?ová, Ivana,?tícha, Martin,Vesely, Jan

, p. 5080 - 5089 (2021/09/30)

An organocatalytic asymmetric domino Michael/α-alkylation reaction between enals and non-stabilized alkyl halides has been developed. Chiral secondary amine catalyzed cyclization reaction of 1-bromo-3-nitropropane with α,β-unsaturated aldehydes provides 1,2,3-trisubstituted cyclopentane carbaldehydes with high diastereo- (dr up to 8 : 1) and enantioselectivities (ee up to 96 %).

Highly Regio- A nd Enantioselective Hydrogenation of Conjugated α-Substituted Dienoic Acids

Liu, Xian,Liu, Song,Wang, Quanjun,Zhou, Gang,Yao, Lin,Ouyang, Qin,Jiang, Ru,Lan, Yu,Chen, Weiping

, p. 3149 - 3154 (2020/04/09)

Highly regio- A nd enantioselective hydrogenation of conjugated α-substituted dienoic acids was realized for the first time using Trifer-Rh complex, providing a straightforward method for the synthesis of chiral α-substituted ?,?′-unsaturated acids. DFT calculations revealed N+H-O hydrogen bonding interaction is formed to stabilize the transition state and the coordination of 4,5-double bond to Rh(III) center would facilitate the reductive elimination process. This hydrogenation provided a gram-scale synthesis of the precursor of sacubitril.

Biocatalytic reduction of α,β-unsaturated carboxylic acids to allylic alcohols

Aleku, Godwin A.,Leys, David,Roberts, George W.

, p. 3927 - 3939 (2020/07/09)

We have developed robust in vivo and in vitro biocatalytic systems that enable reduction of α,β-unsaturated carboxylic acids to allylic alcohols and their saturated analogues. These compounds are prevalent scaffolds in many industrial chemicals and pharmaceuticals. A substrate profiling study of a carboxylic acid reductase (CAR) investigating unexplored substrate space, such as benzo-fused (hetero)aromatic carboxylic acids and α,β-unsaturated carboxylic acids, revealed broad substrate tolerance and provided information on the reactivity patterns of these substrates. E. coli cells expressing a heterologous CAR were employed as a multi-step hydrogenation catalyst to convert a variety of α,β-unsaturated carboxylic acids to the corresponding saturated primary alcohols, affording up to >99percent conversion. This was supported by the broad substrate scope of E. coli endogenous alcohol dehydrogenase (ADH), as well as the unexpected CC bond reducing activity of E. coli cells. In addition, a broad range of benzofused (hetero)aromatic carboxylic acids were converted to the corresponding primary alcohols by the recombinant E. coli cells. An alternative one-pot in vitro two-enzyme system, consisting of CAR and glucose dehydrogenase (GDH), demonstrates promiscuous carbonyl reductase activity of GDH towards a wide range of unsaturated aldehydes. Hence, coupling CAR with a GDH-driven NADP(H) recycling system provides access to a variety of (hetero)aromatic primary alcohols and allylic alcohols from the parent carboxylates, in up to >99percent conversion. To demonstrate the applicability of these systems in preparative synthesis, we performed 100 mg scale biotransformations for the preparation of indole-3-aldehyde and 3-(naphthalen-1-yl)propan-1-ol using the whole-cell system, and cinnamyl alcohol using the in vitro system, affording up to 85percent isolated yield.

Boosting multiple photo-assisted and temperature controlled reactions with a single redox-switchable catalyst: Solvents as internal substrates and reducing agent

Bania, Kusum K.,Baruah, Manash J.,Bhattacharyya, Pradip K.,Das, Biraj,Karunakar, Galla V.,Roy, Subhasish,Saikia, Lakshi,Saikia, Pinku,Sharma, Mukesh

, p. 104 - 121 (2020/06/01)

An alternative and economically viable process for the synthesis of β-aryl enals, enones and the aryl amines has been developed by partial oxidation of ethanol, isopropanol and N, N-dimethyl formamide (DMF). The formation of β-aryl enals, enones and the aryl amines was catalyzed by a mixed metal oxides layer of cobalt and chromium supported on halloysite nanotubes, designated as CoCr2O4-HNT. The C[sbnd]C and C[sbnd]N bond formation reactions were found to be influenced by temperature and the nature of base. The condensation of aldehyde with in situ generated acetaldehyde by ethanol oxidation forming β-aryl enals occurred selectively at 120 °C. The partial oxidation of isopropanol to acetone and its condensation with aldehydes forming β-aryl enones occurred at room temperature. Increase in temperature caused the liberation of hydrogen gas from isopropanol and allowed the reversible reduction of aldehydes to alcohols. Increase in temperature in isopropanol and increase in base concentration in ethanol causes the selective reduction of aldehydes to alcohols. Besides being active for the Claisen-Schmidt type of reactions and the aryl halides amination process, the synthesized catalyst was also found to be highly active for the photocatalytic oxidation of benzyl alcohols in absence of any external oxidizing agent. The positive holes (h+) generated at the Co(II) site as evident from EPR analysis was considered to be responsible for high photocatalytic activity of the material reducing the recombination rate of holes and electrons (e?). Density Functional Theory calculations were performed to understand the mechanism of ethanol oxidation to acetaldehyde.

Process route upstream and downstream products

Process route

p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

allyl alcohol
107-18-6

allyl alcohol

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

4,4'-dinitrobiphenyl
1528-74-1

4,4'-dinitrobiphenyl

3-(4-nitrophenyl)propanal
80793-24-4

3-(4-nitrophenyl)propanal

Conditions
Conditions Yield
With dichloro(1,5-cyclooctadiene)palladium(II); sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 85 ℃; for 5h; Reagent/catalyst; Inert atmosphere;
48%
7%
24%
ethanol
64-17-5

ethanol

4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

Conditions
Conditions Yield
With sodium hydroxide; at 120 ℃; for 4h; pH=8;
92%
With caesium carbonate; In water; at 120 ℃; for 8h;
90%
3-(4-nitrophenyl)propyl-2-en-1-ol
35271-56-8,142917-82-6,1504-63-8

3-(4-nitrophenyl)propyl-2-en-1-ol

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

Conditions
Conditions Yield
With sodium hypochlorite; sodium tetraborate decahydrate; PIPO; In acetic acid methyl ester; at 0 ℃; for 2h; pH=9.5;
99%
With titanium(IV) oxide; oxygen; at 29.84 ℃; for 6h; under 760.051 Torr; Sealed tube; Irradiation;
99%
With benzyltriphenylphosphonium peroxymonosulfate; for 0.0833333h;
98%
With benzyltriphenylphosphonium peroxymonosulfate; In acetonitrile; for 2h; Heating;
98%
With benzyltriphenylphosphonium dichromate; for 0.166667h;
96%
With benzyltriphenylphosphonium dichromate; silica gel; at 20 ℃; for 0.166667h;
96%
With benzyltriphenylphosphonium dichromate; In acetonitrile; for 0.333333h; Heating;
95%
With benzyltriphenylphosphonium chlorochromate; In dichloromethane; for 0.0333333h; microwave irradiation;
95%
With aluminum oxide; potassium permanganate; In neat (no solvent); for 0.0333333h;
91%
With 1-benzyl-4-aza-1-azoniabiyclo<2.2.2>octane peroxodisulfate; In acetonitrile; for 0.666667h; Heating;
90%
With Dess-Martin periodane; In dichloromethane; at 20 ℃;
90%
With 10% Ru/C; oxygen; In toluene; at 50 ℃; for 24h; under 760.051 Torr;
85%
With potassium phosphate; carbon dioxide; In dimethyl sulfoxide; at 90 ℃; for 48h;
81%
With bismuth (III) nitrate pentahydrate; cellulose supported copper(0); oxygen; In acetonitrile; at 60 ℃; for 2h;
62%
With oxygen; Pd2060(NO3)360(OAc)360O80; In acetic acid; at 60 ℃; for 10h;
37 % Chromat.
With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 2h;
With Pd(0) nanocatalyst on 3-aminopropyltrimethoxysilane-functionalized mesocellular foam; air; In toluene; at 70 ℃;
With aluminum oxide; dipyridinium dichromate; In dichloromethane; at 20 ℃; for 24h;
With manganese(IV) oxide; In dichloromethane; at 20 ℃;
With manganese(IV) oxide; In dichloromethane; at 20 ℃; for 5h;
5.6 g
4-nitrobenzaldehdye
555-16-8

4-nitrobenzaldehdye

acetaldehyde
75-07-0,9002-91-9

acetaldehyde

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

Conditions
Conditions Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 19h; Inert atmosphere;
82%
With potassium hydroxide; In methanol; at 0 - 10 ℃; for 1.3h;
45.3%
With C48H66N8O6; In water; at 20 ℃;
35%
man kocht die entstandene Verbindung mit Essigsaeureanhydrid;
man kocht die entstandene Verbindung mit Eisessig;
With potassium hydroxide; In methanol;
Multistep reaction; (i) NaOH, MeOH, (ii) Ac2O;
With potassium hydroxide; In methanol;
With sodium hydroxide; In ethanol; water; at 0 - 20 ℃; for 11h;
4-nitrobenzaldehdye; With sodium hydroxide; In ethanol; water; at 0 ℃; for 0.166667h;
acetaldehyde; In ethanol; water; at 0 - 20 ℃; for 11h;
(1-nitro-4-(prop-1-en-1-yl)benzene)
25798-60-1

(1-nitro-4-(prop-1-en-1-yl)benzene)

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

Conditions
Conditions Yield
With tert.-butylhydroperoxide; Ru(2,4,13,15-tetraphenyl-1,5,12,16-tetraaza-tricyclo[14.2.2.06,11]eicosa-4,6(11),7,9,12-pentaene)Cl2; In acetonitrile; at 20 ℃; for 3h; Reagent/catalyst; Irradiation;
76%
3-(4-nitrophenyl)propanal
80793-24-4

3-(4-nitrophenyl)propanal

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

Conditions
Conditions Yield
With oxygen; palladium diacetate; 2-methoxy-phenylamine; In dimethyl sulfoxide; at 60 ℃; for 18h; under 760.051 Torr;
56%
With (S)-diphenylprolinol; oxygen; palladium diacetate; In dimethyl sulfoxide; at 45 ℃; for 8h; under 760.051 Torr;
43%
With (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; at 20 ℃; for 1h;
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

allyl alcohol
107-18-6

allyl alcohol

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

3-(4-nitrophenyl)propanal
80793-24-4

3-(4-nitrophenyl)propanal

Conditions
Conditions Yield
With tetrabutyl-ammonium chloride; oxygen; palladium diacetate; sodium hydrogencarbonate; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 60 ℃; for 5h; under 760.051 Torr;
60%
5%
p-nitrobenzene iodide
636-98-6

p-nitrobenzene iodide

N-allyl-N-methylaniline
6628-07-5

N-allyl-N-methylaniline

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

Conditions
Conditions Yield
With tetrabutylammomium bromide; sodium acetate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 100 ℃; for 14h; in air;
60%
acrylaldehyde diethyl acetal
3054-95-3

acrylaldehyde diethyl acetal

para-nitrophenyl bromide
586-78-7

para-nitrophenyl bromide

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

ethyl 3-(4-nitrophenyl)propanoate
7116-34-9

ethyl 3-(4-nitrophenyl)propanoate

Conditions
Conditions Yield
acrylaldehyde diethyl acetal; para-nitrophenyl bromide; With N-Methyldicyclohexylamine; tetrabutylammomium bromide; In N,N-dimethyl-formamide; at 120 ℃; for 6h;
With hydrogenchloride; In water; ethyl acetate; at 20 ℃; chemoselective reaction;
92%
3-(4-nitrophenyl)propyl-2-en-1-ol
35271-56-8,142917-82-6,1504-63-8

3-(4-nitrophenyl)propyl-2-en-1-ol

phosphonic acid diethyl ester
762-04-9

phosphonic acid diethyl ester

3-(4-nitrophenyl)-2-propenal
1734-79-8

3-(4-nitrophenyl)-2-propenal

diethyl (E)-3-(4-nitrophenyl)prop-2-enyl phosphate

diethyl (E)-3-(4-nitrophenyl)prop-2-enyl phosphate

Conditions
Conditions Yield
With dihydrogen peroxide; iodine; In water; at 20 ℃;
50%
40%

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