626-99-3

Basic information

• Product Name: 2,4-Pentadienoic acid
• Synonyms: a,g-Pentadienoic acid (3CI);1,3-Butadiene-1-carboxylicacid;1-Carboxy-1,3-butadiene;1-Carboxybutadiene;Butadiene-1-carboxylic acid;NSC 16628;β-Vinylacrylic acid
• CAS NO: 626-99-3
• Molecular Formula: C₅H₆O₂
• Molecular Weight: 98.0999
• EINECS: 210-976-1
• Mol File: 626-99-3.mol
• Article Data: 5

Chemical Properties

• Melting Point: 69-72℃
• Boiling Point: 215 °C at 760 mmHg
• Flash Point: 121.5 °C
• Appearance: /
• Density: 1.039 g/cm³
• Vapor Pressure: 0.0586mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: ?20°C
• Solubility: 1 M NaOH: soluble0.5g/10 mL, clear, brown
• PKA: 4.47±0.10(Predicted)
• BRN: 1739248
• CAS DataBase Reference: 2,4-Pentadienoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Pentadienoic acid(626-99-3)
• EPA Substance Registry System: 2,4-Pentadienoic acid(626-99-3)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• F: 4.4-8-9-23
• Hazardous Substances Data: 626-99-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 626-99-3 differently. You can refer to the following data:
1. The short chain fatty acids in Penta-2,4-dienoic Acid is used for treatment and prevention of eye and skin diseases.
2. 2,4-Pentadienoic acid was used in preparation of chiral propargylester. It was also used in the preparation of trans 1-N-acylamino-1,3-dienes via modified Curtius procedure.

Definition

ChEBI: A pentadienoic acid with the double bonds at positions 2 and 4.

Synthesis Reference(s)

The Journal of Organic Chemistry, 41, p. 2527, 1976 DOI: 10.1021/jo00877a004Tetrahedron Letters, 28, p. 311, 1987 DOI: 10.1016/S0040-4039(00)95715-0

InChI:InChI=1/C5H6O2/c1-2-3-4-5(6)7/h2-4H,1H2,(H,6,7)/b4-3+

Synthetic route

pyridine (110-86-1) + malonic acid (141-82-2) + acrolein (107-02-8) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
in aetherischer Loesung;

3,5-disulfo-valeric acid ; dipotassium-salt with tripotassium-salt → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
bei der Kalischmelze;

malonic acid (141-82-2) + acrolein (107-02-8) → 1,3-butadiene-1-carboxylic acid (626-99-3)

ethyl 2,4-pentadienoate (13038-12-5) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
(hydrolysis);

(RS)-3-amino-pent-4-enoic acid (14403-19-1) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
(heating);

carbon dioxide (124-38-9) + buta-1,3-diene (106-99-0) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel (0); Maleinsaeureanhydrid; 1,2-bis-(dicyclohexylphosphino)ethane 1.) THF, RT, 48 h, 2.) THF, 20 deg C, 48 h; Yield given. Multistep reaction;

β.δ-disulfo-n-valerate of potassium → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With potassium hydroxide

potassium-2.4-disulfo valerate → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With potassium hydroxide

1-benzoyl-4-vinyl-azetidin-2-one (14403-16-8) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: (i) NaOH, (ii) aq. HCl 2: (heating) View Scheme

BPA (80-05-7) → (2E,4E)-2,4-hexadienedioic acid (3588-17-8) + 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With dihydrogen peroxide In water at 39.84℃; Temperature; Reagent/catalyst;

4-hydroxy 2-pentenoic acid → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With 4-hydroxypent-2-enoate dehydratase Enzymatic reaction;

2,4-pentadienoyl-CoA → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With 2,4-pentadienoyl-CoA hydrolase

2-oxo-4-pentenoic acid (20406-62-6) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 2-oxopent-4-enoate reductase / Enzymatic reaction 2: 2-hydroxypent-4-enoate mutase / Enzymatic reaction 3: 3-hydroxypent-4-enoate dehydratase / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: 2-oxopent-4-enoate reductase / Enzymatic reaction 2: 2-hydroxypent-4-enoate vinylisomerase / Enzymatic reaction 3: 5-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

2-hydroxypent-4-enoic acid (67951-43-3) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-hydroxypent-4-enoate mutase / Enzymatic reaction 2: 3-hydroxypent-4-enoate dehydratase / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: 2-hydroxypent-4-enoate vinylisomerase / Enzymatic reaction 2: 5-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

hydroxyvalerenic acid (23251-44-7) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With 5-hydroxypent-2-enoate dehydratase Enzymatic reaction;

(RS)-3-hydroxy-4-pentenoic acid (81357-28-0) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With 3-hydroxypent-4-enoate dehydratase Enzymatic reaction;

4-hydroxy-2-oxopentanoic acid (41453-55-8, 3318-73-8) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 4-hydroxy-2-oxovalerate 3-dehydratase / Enzymatic reaction 2: 2-oxopent-3-enoate reductase / Enzymatic reaction 3: 2-hydroxypent-3-enoate dehydratase/vinylisomerase / Enzymatic reaction View Scheme
Multi-step reaction with 4 steps 1: 4-hydroxy 2- oxovalerate dehydratase / Enzymatic reaction 2: 2-oxopent-4-enoate reductase / Enzymatic reaction 3: 2-hydroxypent-4-enoate mutase / Enzymatic reaction 4: 3-hydroxypent-4-enoate dehydratase / Enzymatic reaction View Scheme
Multi-step reaction with 4 steps 1: 4-hydroxy 2- oxovalerate dehydratase / Enzymatic reaction 2: 2-oxopent-4-enoate reductase / Enzymatic reaction 3: 2-hydroxypent-4-enoate vinylisomerase / Enzymatic reaction 4: 5-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme
Multi-step reaction with 4 steps 1: 4-hydroxy-2-oxovalerate 3-dehydratase / Enzymatic reaction 2: 2-oxopent-3-enoate reductase / Enzymatic reaction 3: 2-hydroxypent-3-enoate vinylisomerase / Enzymatic reaction 4: 4-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

C5H6O3 → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 2-oxopent-3-enoate reductase / Enzymatic reaction 2: 2-hydroxypent-3-enoate dehydratase/vinylisomerase / Enzymatic reaction View Scheme
Multi-step reaction with 3 steps 1: 2-oxopent-3-enoate reductase / Enzymatic reaction 2: 2-hydroxypent-3-enoate vinylisomerase / Enzymatic reaction 3: 4-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

4-hydroxy-3-oxo-pentanoic acid → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 3- oxo-4-hydroxypentanoate reductase / Enzymatic reaction 2: 3,4-dihydroxypentanoate dehydratase / Enzymatic reaction 3: 4-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

3,4-dihydroxy-valeric acid (58957-59-8) → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: 3,4-dihydroxypentanoate dehydratase / Enzymatic reaction 2: 4-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

C5H8O3 → 1,3-butadiene-1-carboxylic acid (626-99-3)

Conditions	Yield
With 2-hydroxypent-3-enoate dehydratase/vinylisomerase Enzymatic reaction;
Multi-step reaction with 2 steps 1: 2-hydroxypent-3-enoate vinylisomerase / Enzymatic reaction 2: 4-hydroxypent-2-enoate dehydratase / Enzymatic reaction View Scheme

1,3-butadiene-1-carboxylic acid (626-99-3) + phenethylamine (64-04-0) → C13H15NO

Conditions	Yield
With 4-(dimethylamino)pyridine N-oxide; 3,5-bis-trifluromethylphenylboronic acid In fluorobenzene for 16h; Reflux; chemoselective reaction;	98%

1,3-butadiene-1-carboxylic acid (626-99-3) → 2,4-pentadien-1-ol (4949-20-6)

Conditions	Yield
Stage #1: 1,3-butadiene-1-carboxylic acid With triethylamine; methyl chloroformate In diethyl ether at 0℃; for 0.5h; Stage #2: With sodium tetrahydroborate In methanol; diethyl ether at 0℃; for 0.5h;	95%
With lithium aluminium tetrahydride

1,3-butadiene-1-carboxylic acid (626-99-3) + Propargylamine (2450-71-7) → C8H9NO

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0℃;	94%

1,3-butadiene-1-carboxylic acid (626-99-3) + 2-nitrosotoluene (611-23-4) → C12H13NO3 (1257308-20-5)

Conditions	Yield
In N,N-dimethyl-formamide at 95℃; under 750.075 Torr; for 0.783333h; Diels-Alder reaction;	75%

1,3-butadiene-1-carboxylic acid (626-99-3) + benzyl alcohol (100-51-6) → benzyl trans-2,4-pentadienoate (380870-40-6)

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5.5h; Cooling with ice;	71%

1,3-butadiene-1-carboxylic acid (626-99-3) + phenethylamine (64-04-0) → C13H15NO + C21H26N2O

Conditions	Yield
With 3,5-bis-trifluromethylphenylboronic acid In fluorobenzene for 16h; Reflux; chemoselective reaction;	A 45% B n/a

1,3-butadiene-1-carboxylic acid (626-99-3) + p-benzoquinone (106-51-4) → 5,8-dioxo-1,4,4a,5,8,8a-hexahydronaphthalene-1-carboxylic acid (6943-52-8, 93601-99-1, 93602-00-7)

Conditions	Yield
In toluene at 80℃; for 24h; Diels-Alder Cycloaddition;	24%

methanol (67-56-1) + 1,3-butadiene-1-carboxylic acid (626-99-3) → methyl 2,4-pentadienoate (1515-75-9)

Conditions	Yield
With hydrogenchloride	20%
With sulfuric acid
With sulfuric acid Heating;

1-vinylnaphthalene (826-74-4) + 1,3-butadiene-1-carboxylic acid (626-99-3) → 2-[1]naphthyl-cyclohex-1-enecarboxylic acid

Conditions	Yield
With acetic acid; hydroquinone at 100℃;

1-vinylnaphthalene (826-74-4) + 1,3-butadiene-1-carboxylic acid (626-99-3) → 6-[1]naphthyl-cyclohex-1-enecarboxylic acid

Conditions	Yield
With propionic acid; hydroquinone

ethanol (64-17-5) + 1,3-butadiene-1-carboxylic acid (626-99-3) → ethyl 2,4-pentadienoate (13038-12-5)

Conditions	Yield
With hydrogenchloride

1,3-butadiene-1-carboxylic acid (626-99-3) → 4,5-dibromo-pent-2-enoic acid (85858-56-6)

Conditions	Yield
With carbon disulfide

1,3-butadiene-1-carboxylic acid (626-99-3) → (Z)-2-pentenoic acid (16666-42-5)

Conditions	Yield
With methanol; platinum(IV) oxide; hydrogen under 1471.02 Torr; Hydrogenation;

1,3-butadiene-1-carboxylic acid (626-99-3) → (E)-3-pentenoic acid (1617-32-9)

Conditions	Yield
With sodium hydroxide bei der elektrolytischen Reduktion an einer Kupferkathode;
With sodium amalgam; sodium hydrogencarbonate; sodium carbonate
With ammonia; lithium

1,3-butadiene-1-carboxylic acid (626-99-3) → 3,5-dichloro-2,4-dihydroxy-valeric acid

Conditions	Yield
With water; hypochloric acid substance of ingold,Prichard,Smith;

1,3-butadiene-1-carboxylic acid (626-99-3) → DL-tartaric acid (133-37-9)

Conditions	Yield
With potassium permanganate at 0℃;

1,3-butadiene-1-carboxylic acid (626-99-3) → trans 2,4-pentadienoyl chloride (52126-35-9)

Conditions	Yield
With thionyl chloride; zinc(II) chloride; Petroleum ether; zinc at 60℃;

1,3-butadiene-1-carboxylic acid (626-99-3) → 3-pentenoic acid (5204-64-8)

Conditions	Yield
With sodium amalgam

1,3-butadiene-1-carboxylic acid (626-99-3) → 5-chloro-4-hydroxy-pent-2-enoic acid

Conditions	Yield
With water; hypochloric acid at 50℃;

1,3-butadiene-1-carboxylic acid (626-99-3) → (E)-5-bromo-4-hydroxy-2-pentenoic acid (78508-86-8)

Conditions	Yield
With diethyl ether; water; hypobromous acid
With water; hypobromous acid

1,3-butadiene-1-carboxylic acid (626-99-3) → 4,5-dichloro-pent-2-enoic acid

Conditions	Yield
With chloroform; chlorine

1,3-butadiene-1-carboxylic acid (626-99-3) → 2,3,4,5-tetrabromo-valeric acid (135038-94-7)

Conditions	Yield
With carbon disulfide; bromine
With bromine

1,3-butadiene-1-carboxylic acid (626-99-3) → valeric acid (109-52-4)

Conditions	Yield
With sodium hydroxide bei der elektrolytischen Reduktion;

1,3-butadiene-1-carboxylic acid (626-99-3) + dinitromethylene-methoxy-amine oxide (2777-25-5) → 3-(2-methoxy-3,3-dinitro-isoxazolidin-5-yl)-acrylic acid (17823-17-5)

Conditions	Yield
In toluene at 0℃;

1,3-butadiene-1-carboxylic acid (626-99-3) → (E)-2,4-pentadien-1-ol (4949-20-6)

Conditions	Yield
With lithium aluminium tetrahydride at -30℃;

1,3-butadiene-1-carboxylic acid (626-99-3) → penta-3,4-dienoic acid (60053-24-9)

Conditions	Yield
In diethyl ether Irradiation;

Upstream product

• 110-86-1 pyridine 
• 141-82-2 malonic acid 
• 107-02-8 acrolein 
• 58957-59-8 3,4-dihydroxy-valeric acid 
• 41453-55-8 4-hydroxy-2-oxopentanoic acid 
• 81357-28-0 (RS)-3-hydroxy-4-pentenoic acid 
• 23251-44-7 hydroxyvalerenic acid 
• 67951-43-3 2-hydroxypent-4-enoic acid 
• 20406-62-6 2-oxopent-4-enoic acid 
• 80-05-7 BPA 
• 14403-16-8 1-benzoyl-4-vinyl-azetidin-2-one 
• 124-38-9 carbon dioxide 
• 106-99-0 buta-1,3-diene 
• 14403-19-1 (RS)-3-amino-pent-4-enoic acid 

Downstream Products

• 1515-75-9 methyl 2,4-pentadienoate 
• 13038-12-5 ethyl 2,4-pentadienoate 
• 4949-20-6 (E)-2,4-pentadien-1-ol 
• 4949-20-6 2,4-pentadien-1-ol 
• 109-52-4 valeric acid 
• 5204-64-8 3-pentenoic acid 
• 591-80-0 pent-4-enoic acid 
• 72120-54-8 1-(benzyloxycarbonyl)hexahydro-3-pyridazinecarboxylic acid 
• 764-38-5 (3Z)-pent-3-en-1-ol 
• 4635-87-4 3-pentenenitrile 
• 17066-20-5 3-pentenoyl chloride 
• 106-99-0 buta-1,3-diene 
• 380870-40-6 benzyl trans-2,4-pentadienoate 

Relevant articles and documents

Palladium-Promoted Neutral 1,4-Brook Rearrangement/Intramolecular Allylic Cyclization Cascade Reaction: A Strategy for the Construction of Vinyl Cyclobutanols

A cascade reaction to build vinyl cyclobutanol rings through activation of vinyl epoxides by palladium, followed by 1,4-Brook rearrangement and intramolecular cyclization with a palladium complex of the resulting carbon anion, is described. Through this cascade reaction, several highly substituted cyclobutanol substrates were achieved in good yields with high stereoselectivities.

SBA-15 supported Fe, Ni, Fe-Ni bimetallic catalysts for wet oxidation of bisphenol-A

Bisphenol A is considered as pollutant, because it is toxic and hazardous to living organisms even at very low concentrations. Biological oxidation used for removing this organic from waste water is not suitable and consequently application of catalytic wet oxidation has been considered as one of the best options for treating bisphenol A. We have developed Fe/SBA-15, Ni/SBA-15 and Fe-Ni/SBA-15 as heterogeneous catalysts using the advanced impregnation method for oxidation of bisphenol A in water. The catalysts were characterized with physico-chemical characterization methods such as, powder X-ray diffraction (PXRD), FT-IR measurements, N2 adsorption-desorption isotherm, thermo-gravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and inductively coupled plasma optical emission spectroscopy (ICPOES) analysis. This work illustrates activity of the catalysts for heterogeneous catalytic degradation reaction revealed with excellent conversion and recyclability. The degradation products identified were not persistent pollutants. GC-MS analysis identified the products: 2,4-hexadienedioic acid, 2,4-pentadienic acid and isopropanol or acetic acid. The leachability study indicated that the catalysts release very little metals to water. Therefore, the possibility of water contamination through metal leaching was almost negligible.

DIENCARBONSAEUREN AUS 1,3-DIENEN UND CO2 DURCH C-C-VERKNUEPFUNG AN NICKEL(0)

(Lig)Ni0 systems react with 1,3-dienes in the presence of CO2 to give nickela carboxylates.The influence of ligands and temperature on the regioselectivity of the C-C bond formation is elucidated.In some cases the nickela carboxylates undergo reductive elimination under the influence of maleic anhydride, and the coupled diene/CO2 moiety rearranges to give the diene carboxylic acid.A possible reaction sequence is discussed.