3-nitrocinnamic acid supplier

Name
3-Nitrocinnamic acid
EINECS 209-104-2
CAS No. 555-68-0
Article Data109
CAS DataBase
Density 1.411 g/cm³
Solubility
Melting Point 200-202 °C(lit.)
Formula C₉H₇NO₄
Boiling Point 372.1 °C at 760 mmHg
Molecular Weight 193.159
Flash Point 166.5 °C
Transport Information
Appearance Light yellow fine crystalline powder
Safety 22-24/25
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms Cinnamicacid, m-nitro- (6CI,7CI,8CI);3-(3-Nitrophenyl)-2-propenoic acid;3-(3-Nitrophenyl)acrylic acid;3-Nitrobenzenepropenoic acid;Ethyl 3-(3-nitrophenyl)-2-propenoate;NSC 5408;m-Nitrocinnamic acid;
PSA 83.12000
LogP 2.21580

Synthetic route

: 141-82-2
malonic acid

: 99-61-6
3-nitro-benzaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-amino propanoic acid In ethanol at 20℃; Knoevenagel-Doebner reaction; stereoselective reaction;	98%
With piperidine; pyridine for 0.0333333h; microwave irradiation;	97%
With ammonium acetate for 0.0666667h; Irradiation;	95%

: 645-00-1
m-iodonitrobenzene

: 79-10-7
acrylic acid

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With sodium carbonate In water at 120℃; for 12h; Green chemistry;	96.5%
With potassium carbonate In water for 12h; Heck Reaction; Inert atmosphere; Reflux;	95%
With tributyl-amine; silica-supported bidentate arsine palladium(0) In para-xylene at 100℃; for 6h; Heck arylation;	87%

: 141-82-2
malonic acid

: 68444-12-2
sodium α-hydroxy-m-nitrotoluene-α-sulphonate

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With piperazine In ethylene glycol for 0.125h; Knoevenagel condensation; microwave irradiation;	92%

: 585-79-5
3-Bromonitrobenzene

: 79-10-7
acrylic acid

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With potassium carbonate In water for 12h; Heck Reaction; Inert atmosphere; Reflux;	92%

: 111425-75-3, 36574-84-2
(E)-2'-hydroxy-3-nitrochalcone

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With dihydrogen peroxide; potassium carbonate In acetonitrile at 20℃; for 5h;	91%

: 99-61-6
3-nitro-benzaldehyde

: 64-19-7
acetic acid

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With pyridine; dmap; lithium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 8h;	82%
With pyridine; dmap; sodium tetraborate decahydrate; N-benzyl-N,N,N-triethylammonium chloride In 1-methyl-pyrrolidin-2-one at 185 - 190℃; for 7h;	82%

: 108-24-7
acetic anhydride

: 99-61-6
3-nitro-benzaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With trichlorophosphate at 80 - 90℃; Condensation; Perkin reaction;	80%
With tetraacetyl diborate
With sodium acetate

: 24163-36-8
3,3'-dinitrodiphenyliodonium bromide

: 79-10-7
acrylic acid

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
palladium dichloride In water for 0.0166667h; Heck reaction; microwave irradiation;	80%

: 2-(3-nitro-phenyl)-1-thia-4a,9-diaza-fluoren-4-one

A: 40828-54-4
1H-benzimidazole-2-sulfonic acid

B: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With dihydrogen peroxide; acetic acid for 24h;	A 59% B 56%

: 113-24-6
sodium pyruvate

: 99-61-6
3-nitro-benzaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 0℃; for 2h;	36%

: 110-89-4
piperidine

: 110-86-1
pyridine

: 141-82-2
malonic acid

: 99-61-6
3-nitro-benzaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

...Expand

: 91-22-5
quinoline

: 141-82-2
malonic acid

: 99-61-6
3-nitro-benzaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

...Expand

: 141-82-2
malonic acid

: 99-61-6
3-nitro-benzaldehyde

A: 555-68-0
(E)-3-Nitrocinnamic acid

B: 5678-47-7
3-amino-3-(3-nitro-phenyl)-propionic acid

Conditions

Conditions	Yield
With ammonium acetate In ethanol for 24h; Heating;
With ammonia

...Expand

: 99-09-2
3-nitro-aniline

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With hydrogenchloride Diazotization.Eintragen in ein Gemisch von Maleinsaeure (oder Acrylsaeure), Kupfer(II)-chlorid, Natriumacetat und Wasser;

: 2,3-Dibromo-3-(3-nitro-phenyl)-propionic acid

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With sodium iodide In N,N-dimethyl-formamide at 29.9℃; Kinetics; Thermodynamic data; Mechanism; effect of temperature; ΔH(excit.), ΔS(excit), ΔG(excit.);

: 99-61-6
3-nitro-benzaldehyde

acetic acid silicic acid-anhydride: acetic acid silicic acid-anhydride

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With sodium acetate at 180 - 185℃;

: 99-61-6
3-nitro-benzaldehyde

Wittig'salt: Wittig'salt

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With sodium hydroxide; water; sodium hydride modified Wittig's reaction; 1.)THF, R.T., 3 h; 2.)CH3OH, reflux, 8 h; Yield given. Multistep reaction;

: 645-00-1
m-iodonitrobenzene

poly(ethylene glycol) diacrylate: poly(ethylene glycol) diacrylate

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
Stage #1: m-iodonitrobenzene; poly(ethylene glycol) diacrylate With palladium diacetate; tetrabutylammomium bromide; potassium carbonate at 80℃; for 8h; Heck reaction; Stage #2: With sodium hydroxide at 20℃;

: 110-89-4
piperidine

: 99-61-6
3-nitro-benzaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With pyridine; malonic acid In water

: 350490-16-3
butyl (3-nitro)cinnamate

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0℃; for 4h;

: 645-00-1
m-iodonitrobenzene

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine; tris-(dibenzylideneacetone)dipalladium(0); tris-(o-tolyl)phosphine / N,N-dimethyl-formamide / 12 h / 90 °C / Inert atmosphere 2: lithium hydroxide monohydrate; water / tetrahydrofuran / 12 h / 25 °C View Scheme

: 659-04-1
methyl 3-nitrocinnamate

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
With lithium hydroxide monohydrate; water In tetrahydrofuran at 25℃; for 12h;

: 99-61-6
3-nitro-benzaldehyde

A: 555-68-0
(E)-3-Nitrocinnamic acid

B: 19883-74-0
(2S)-2-amino-3-(3-nitrophenyl)propanoic acid

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium formate / ethanol / 4 h / Reflux 2: phenylalanine ammonia lyase from Streptomyces maritimus; phenylalanine ammonia α-lyase from Anabaena variabilis / aq. buffer / 24 h / 30 °C / pH 8 / Resolution of racemate; Enzymatic reaction View Scheme

: 5678-47-7
3-amino-3-(3-nitro-phenyl)-propionic acid

A: 787544-61-0
(R)-3-amino-3-(3-nitrophenyl)propanoic acid

B: 555-68-0
(E)-3-Nitrocinnamic acid

C: 19883-74-0
(2S)-2-amino-3-(3-nitrophenyl)propanoic acid

Conditions

Conditions	Yield
With phenylalanine ammonia α-lyase from Anabaena variabilis; phenylalanine ammonia lyase from Streptomyces maritimus In aq. buffer at 30℃; for 24h; pH=8; Reagent/catalyst; Resolution of racemate; Enzymatic reaction; enantioselective reaction;

...Expand

: 1504-76-3
3-nitrocinnamaldehyde

: 555-68-0
(E)-3-Nitrocinnamic acid

Conditions

Conditions	Yield
Stage #1: 3-nitrocinnamaldehyde With titanium tetrachloride; ethyl bromoacetate; triphenylphosphine In dichloromethane at 0 - 20℃; for 6h; Stage #2: With potassium hydroxide In methanol at 20℃; for 2h;

: 555-68-0
(E)-3-Nitrocinnamic acid

: 586-39-0
1-nitro-3-vinyl-benzene

Conditions

Conditions	Yield
With phosphate buffer; Camellia sinensis for 240h; pH=6.4;	100%
With quinoline; copper at 185 - 195℃;
With Camellia sinensis at 25℃; for 120h; pH=6.4; Decarboxylation;

: 555-68-0
(E)-3-Nitrocinnamic acid

: 136265-09-3
(Z)-ethyl 3-(3-nitrophenyl)acrylate

Conditions

Conditions	Yield
With sulfuric acid In ethanol	99%

: 4112-65-6
5-hydroxy-2-methylisoindoline-1,3-dione

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1242154-02-4
2-methylisoindole-1,3-dion-5-yl (E)-3-(3-nitrophenyl) acrylate

Conditions

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 4h;	98%

: 67-56-1
methanol

: 555-68-0
(E)-3-Nitrocinnamic acid

: 659-04-1
methyl 3-nitrocinnamate

Conditions

Conditions	Yield
With sulfuric acid for 0.0833333h; Esterification; Irradiation;	97%
With sulfuric acid Reflux;	97.3%
With sulfuric acid

: 555-68-0
(E)-3-Nitrocinnamic acid

: 16024-82-1
methyl 2-isothiocyanatobenzoate

: 106-95-6
allyl bromide

: 3-[3-(2-allylsulfanyl-4-oxo-4H-quinazolin-3-yl)-phenyl]-acrylic acid

Conditions

Conditions	Yield
Multistep reaction;	97%

...Expand

: 555-68-0
(E)-3-Nitrocinnamic acid

: 74710-09-1
o-phenylenediamine sulphate

: 55969-91-0
2-(3-nitro-styryl)-1H-benzoimidazole

Conditions

Conditions	Yield
In ethylene glycol for 3h; Heating;	97%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1504-64-9
(E)-3-(3-nitrophenyl)prop-2-en-1-ol

Conditions

Conditions	Yield
Stage #1: (E)-3-Nitrocinnamic acid With sodium tetrahydroborate In tetrahydrofuran for 0.166667h; Stage #2: With iodine In tetrahydrofuran for 1h;	97%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 100-46-9
benzylamine

: 1085449-49-5
(E)-N-benzyl-3-(3-nitrophenyl)acrylamide

Conditions

Conditions	Yield
With tris(2,2,2-trifluoroethyl) borate In acetonitrile at 80℃; for 15h;	95%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 333-20-0
potassium thioacyanate

: 22715-07-7
(E)-3-(3-nitrophenyl)acryloyl isothiocyanate

Conditions

Conditions	Yield
Stage #1: (E)-3-Nitrocinnamic acid With trichloroisocyanuric acid; triphenylphosphine In toluene at 0℃; for 0.25h; Stage #2: potassium thioacyanate In toluene at 0 - 20℃; for 1.5h;	95%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 100-51-6
benzyl alcohol

: 518045-06-2
(E)-benzyl 3-(3-nitrophenyl)acrylate

Conditions

Conditions	Yield
Stage #1: (E)-3-Nitrocinnamic acid With N-chlorobenzotriazole; triphenylphosphine In dichloromethane for 0.25h; Cooling; Stage #2: benzyl alcohol With triethylamine In dichloromethane at 20℃; for 1.33333h;	92%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 35418-05-4, 141236-48-8
(E)-3-nitrocinnamic acid chloride

Conditions

Conditions	Yield
With thionyl chloride In benzene	91%
With thionyl chloride In benzene Heating;	90%
With phosphorus pentachloride; trichlorophosphate

: 555-68-0
(E)-3-Nitrocinnamic acid

: 16024-82-1
methyl 2-isothiocyanatobenzoate

: 3-[3-(4-oxo-2-thioxo-1,4-dihydro-2H-quinazolin-3-yl)-phenyl]-acrylic acid

Conditions

Conditions	Yield
Multistep reaction;	90%

: 91-01-0
1,1-Diphenylmethanol

: 555-68-0
(E)-3-Nitrocinnamic acid

: ((E)-benzhydryl 3-(3-nitrophenyl)acrylate)

Conditions

Conditions	Yield
With sulfonated nanohydroxyapatite functionalized with 2-aminoethyl dihydrogen phosphate In dichloromethane at 41℃; for 3h;	90%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 108-24-7
acetic anhydride

: 32862-98-9
(E)-3-(acetylamino)cinnamic acid

Conditions

Conditions	Yield
Stage #1: (E)-3-Nitrocinnamic acid With hydrogenchloride; tin(ll) chloride In water at 45 - 75℃; for 1h; Stage #2: acetic anhydride With acetic acid at 110℃; for 2h;	89%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 569348-67-0
3-nitro-cinnamoyl azide

Conditions

Conditions	Yield
With sodium azide; N,N-dimethyl-formamide; trichlorophosphate at 10 - 15℃; for 2h;	88%

: 622-85-5
propoxybenzene

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1304637-19-1
C18H17NO4

Conditions

Conditions	Yield
With phosphoric acid; trifluoroacetic acid at 20℃; for 0.5h;	88%

: 1041756-57-3
(4-(4-aminobutyl)piperidin-1-yl)(phenyl)methanone

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1296137-02-4
(E)-N-(4-(1-benzoylpiperidin-4-yl)butyl)-3-(3-nitrophenyl)acrylamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 20℃;	87%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1664-57-9
3-(3-nitrophenyl)propanoic acid

Conditions

Conditions	Yield
With hydroxylamine sulfate; hydroxylamine-O-sulfonic acid In water at 10℃; for 6h; pH=7.6;	86%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 82594-66-9, 115665-66-2, 115665-74-2
(E)-1-(2-bromo-vinyl)-3-nitro-benzene

Conditions

Conditions	Yield
With dibromamine-T; potassium carbonate In acetonitrile at 20℃; for 0.166667h; stereoselective reaction;	85%
With diphosphorus tetraiodide; tetraethylammonium bromide In carbon disulfide at 20℃; for 14h;	80%
With tetraethylammonium bromide; Dess-Martin periodane In dichloromethane at 20℃; for 16h;	65%
Multi-step reaction with 2 steps 1: 84 percent / Br2 / acetic acid / Heating 2: Et3N / dimethylformamide / Heating View Scheme
With [bis(acetoxy)iodo]benzene; tetraethylammonium bromide In dichloromethane at 25℃; for 16h;	2.6 g

: 555-68-0
(E)-3-Nitrocinnamic acid

: 100-66-3
methoxybenzene

: 396725-25-0
(2E)-1-(4-methoxyphenyl)-3-(3-nitrophenyl)prop-2-en-1-one

Conditions

Conditions	Yield
With phosphoric acid; trifluoroacetic acid at 20℃; for 0.5h;	85%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1664-54-6
3-(3-aminophenyl)propionic acid

Conditions

Conditions	Yield
With methanol; hydrogen; acetic acid; palladium on activated charcoal	84%
With ethanol; platinum Hydrogenation;
Multi-step reaction with 2 steps 1: sodium sulfide; aq. NaOH solution 2: mercury-cathode; sodium sulfate; water View Scheme
palladium on charcoal In ethanol; water

: 555-68-0
(E)-3-Nitrocinnamic acid

: 18193-72-1
2,3-dibromo-3-(3-nitro-phenyl)-propionic acid

Conditions

Conditions	Yield
With bromine In acetic acid Heating;	84%

: 555-68-0
(E)-3-Nitrocinnamic acid

: 615-28-1
o-phenylenediamine dihydrochloride

: 55969-91-0
2-(3-nitro-styryl)-1H-benzoimidazole

Conditions

Conditions	Yield
In ethylene glycol for 5h; Condensation; Cycloaddition; Heating;	84%

: 109-65-9
1-bromo-butane

: 555-68-0
(E)-3-Nitrocinnamic acid

: (E)-3-(3'-nitrophenyl)acrylic acid butyl ester

Conditions

Conditions	Yield
With Aliquat 336; potassium carbonate microwave irradiation;	84%

: 461-82-5
4-(trifluoromethoxy)aniline

: 555-68-0
(E)-3-Nitrocinnamic acid

: 1615697-50-1
(E)-N-(4-trifluoromethoxyphenyl)-3-(4-nitrophenyl)acrylamide

Conditions

Conditions	Yield
Stage #1: 4-(trifluoromethoxy)aniline; (E)-3-Nitrocinnamic acid With triethylamine; trichlorophosphate In chloroform at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With triethylamine In chloroform at 0℃; for 0.5h; Inert atmosphere;	83%

3-nitrocinnamic acid Chemical Properties

3-nitrocinnamic acid(555-68-0) is also named as AKOS B004090;3-(3-NITROPHENYL)ACRYLIC ACID;LABOTEST-BB LT00005570;RARECHEM BK HC P253;OTAVA-BB BB7020401717;M-NITROCINNAMIC ACID;m-Nitrocinnamic acid;Cinnamic acid, m-nitro;trans-3-Nitrocinnamic acid;3-nitro-cinnamic acid;Cinnamic acid, m-nitro-,and so on.3-nitrocinnamic acid(555-68-0) is light yellow fine crystalline powder.

CAS: 555-68-0
Molecular Formula: C₉H₇NO₄
Molecular Weight: 193.16
Molecular structure:
EINECS: 209-104-2
Melting point: 200-202 °C(lit.)
Merck: 14,6595
BRN: 1872713
ACD/LogD (pH 5.5): 0.34
ACD/LogD (pH 7.4): -1.19
ACD/BCF (pH 5.5): 1
ACD/BCF (pH 7.4): 1
ACD/KOC (pH 5.5): 4.6
ACD/KOC (pH 7.4): 1
H bond acceptors: 5
H bond donors: 1
Freely Rotating Bonds: 3
Index of Refraction: 1.655
Molar Refractivity: 50.25 cm³
Molar Volume: 136.8 cm³
Polarizability: 19.92 10^-24cm³
Surface Tension: 64.2 dyne/cm
Density: 1.411 g/cm³
Flash Point: 166.5 °C
Enthalpy of Vaporization: 65.32 kJ/mol
Boiling Point: 372.1 °C at 760 mmHg
Vapour Pressure: 3.39E-06 mmHg at 25°C

3-nitrocinnamic acid Uses

3-nitrocinnamic acid(555-68-0) is commonly used as pharmaceutical intermediate for organic synthesis.

3-nitrocinnamic acid Toxicity Data With Reference

RTECS: GE0352000

3-nitrocinnamic acid Safety Profile

Hazard Codes: Xi

Risk Statements: 36/37/38 (36/37/38: Irritating to eyes, respiratory system and skin)
Safety Statements: 22-24/25 (22: Do not breathe dust 24/25: Avoid contact with skin and eyes)
WGK Germany: 3
Hazard Note: Irritant
HS Code: 29163900

Product Name

3-Nitrocinnamic acid

Synthetic route

3-nitrocinnamic acid Chemical Properties

3-nitrocinnamic acid Uses

3-nitrocinnamic acid Toxicity Data With Reference

3-nitrocinnamic acid Safety Profile

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