ACETIDIC ACID

Acetidic acid is a simple dicarboxylic acid with the chemical formula C₃H₄O₄ and the structural formula HOOC–CH₂–COOH, consisting of a methylene group flanked by two carboxylic acid groups.
This structure makes Acetidic acid one of the most reactive and synthetically valuable dicarboxylic acids, widely used as a building block in organic synthesis, particularly in malonic ester synthesis.
Acetidic acid undergoes decarboxylation readily when heated, producing acetic acid and carbon dioxide, which makes it useful in the preparation of barbiturates, vitamins, pharmaceuticals, and fine chemicals.

CAS Number: 141-82-2
EC Number: 205-503-0
Molecular Weight: 104.06100
Molecular Mass: 104.06

Synonyms: malonic acid, propanedioic acid, 141-82-2, Dicarboxymethane, Carboxyacetic acid, Methanedicarboxylic acid, malonate, USAF EK-695, 1,3-Propanedioic acid, Dicarboxylate, Malonicacid, Dicarboxylic acid, NSC 8124, UNII-9KX7ZMG0MK, 9KX7ZMG0MK, AI3-15375, H2malo, EINECS 205-503-0, MFCD00002707, BRN 1751370, Methanedicarbonic acid, CHEBI:30794, Thallium malonate, HOOC-CH2-COOH, NSC-8124, Propane-1,3-dioic acid, alpha,omega-Dicarboxylic acid, DTXSID7021659, HSDB 8437, NSC8124, 4-02-00-01874 (Beilstein Handbook Reference), 1,3-Propanoic acid, PROPANEDIOLIC ACID, METAHNEDICARBOXYLIC ACID, 2fah, MLI, Malonic acid, 99%, Malonic acid (8CI), 1o4m, Malonate dicarboxylic acid, Malonic acid, 99.5%, Propanedioic acid (9CI), SCHEMBL336, WLN: QV1VQ, MALONIC ACID [MI], CH2(COOH)2, CHEMBL7942, MALONIC ACID [INCI], DTXCID401659, SCHEMBL1471092, BDBM14673, Propanedioic acid dithallium salt, Malonic acid, analytical standard, AMY11201, BCP05571, STR00614, Tox21_200534, AC8295, LMFA01170041, s3029, Malonic acid, ReagentPlus(R), 99% AKOS000119034, CS-W019962, DB02175, PROPANEDIOIC ACID, MALONIC ACID, NCGC00248681-01, NCGC00258088-01, BP-11453, CAS-141-82-2, SY001875, Malonic acid, SAJ first grade, >=99.0%, FT-0628127, FT-0628128, FT-0690260, FT-0693474, M0028, NS00013842, EN300-18457, Malonic acid, Vetec(TM) reagent grade, 98%, C00383, C02028, C04025, Q421972, J-521669, Z57965450, F1908-0177, Malonic acid, certified reference material, TraceCERT(R), 592A9849-68C3-4635-AA3D-CBC44965EA3A, Malonic acid, sublimed grade, >=99.95% trace metals basis, DICARBOXYLIC ACID C3, PROPANEDIOLIC ACID, METHANEDICARBOXYLIC ACID, InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7), Malonic acid, anhydrous, free-flowing, Redi-Dri(TM), ReagentPlus(R), 99%, LML,

Acetidic acid is a simple dicarboxylic acid with the molecular formula C₃H₄O₄.
Acetidic acid's structure consists of a central methylene group (–CH₂–) flanked by two carboxylic acid groups (–COOH), making it one of the smallest and most reactive dicarboxylic acids.

Acetidic acid appears as a white crystalline solid, is highly soluble in water, and has a slightly acidic taste.
Acetidic acid is notable for its role as a building block in organic synthesis, particularly in malonic ester synthesis, where it enables the creation of substituted acetic acids.

Acetidic acid undergoes decarboxylation readily when heated, producing acetic acid and carbon dioxide.
Because of this reactivity, Acetidic acid is widely used in the preparation of barbiturates, vitamins (such as B₁), pharmaceuticals, and various fine chemicals.

In biochemistry, Acetidic acid is known as a competitive inhibitor of the enzyme succinate dehydrogenase, interfering with the Krebs cycle by mimicking succinate.
Acetidic acid is also used in industry as a precursor in the synthesis of adhesives, plasticizers, and flavoring agents. 
Despite Acetidic acid's utility, care should be taken in handling, as it may cause skin and eye irritation in concentrated forms.

Acetidic acid appears as white crystals or crystalline powder.
Acetidic acid sublimes in vacuum.

Acetidic acid is a dicarboxylic acid.
Acetidic acid is a dicarboxylic acid with the CH2(COOH)2 structure.

The ionized forms of Acetidic acid and its esters and salts are known as malonates.
For example, diethyl malonate is the diethyl ester of Acetidic acid.

The name of Acetidic acid comes from the Greek μλον (maron), which means "apple".
The crystals of Acetidic acid are triclinic at room temperature.

The oxidation of Acetidic acid by cerium (IV) in sulfuric acid solution has been studied.
The reaction kinetics of the photocatalytic decomposition of Acetidic acid in aqueous suspensions of titanium dioxide (TiO2) have been described.

Acetidic acid is a dicarboxylic acid.
Acetidic acid is an alpha,omega-dicarboxylic acid in which the two carboxy groups are separated by a single methylene group.

Acetidic acid has a role as a human metabolite.
Acetidic acid is a conjugate acid of a malonate(1-).

Acetidic acid, also known as propanedioic acid, is a dicarboxylic acid.
Acetidic acid is a dicarboxylic acid with structure CH2(COOH)2.

The ionized form of Acetidic acid, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Acetidic acid's diethyl ester.

The name of Acetidic acid originates from the Greek word μᾶλον (malon) meaning 'apple'.
Acetidic acid, also known as propanedioic acid, is a dicarboxylic acid.

The crystals of Acetidic acid are triclinic at room temperature.
The oxidation of Acetidic acid by cerium (IV) in sulfuric acid solution has been studied.

The reaction kinetics of the photocatalytic decomposition of Acetidic acid in aqueous suspensions of titanium dioxide (TiO2) have been described.
Acetidic acid is a dicarboxylic acid with structure CH2(COOH)2.

The ionized form of Acetidic acid, as well as its esters and salts, are known as malonates.
For example, diethyl malonate is Acetidic acid"s diethyl ester.

The calcium salt of Acetidic acid occurs in high concentrations in beetroot.
Acetidic acid exists in its normal state as white crystals.

Acetidic acid is the classic example of a competitive inhibitor:
Acetidic acid acts against succinate dehydrogenase (complex II) in the respiratory electron transport chain.
In a well-known reaction, Acetidic acid condenses with urea to form barbituric acid.

Acetidic acid is a simple dicarboxylic acid with the chemical formula C₃H₄O₄ and the structural formula HOOC–CH₂–COOH.
Acetidic acid consists of a methylene group (-CH₂-) bonded to two carboxylic acid groups (-COOH), one on each side.

This unique structure places Acetidic acid among the most reactive and synthetically valuable dicarboxylic acids in organic chemistry.
Acetidic acid appears as a white crystalline solid with a melting point around 135–137°C, and it is highly soluble in water, alcohol, and acetone, which facilitates its use in aqueous and organic-phase reactions.

Acetidic acid is non-toxic in dilute concentrations, though its acidic and irritant properties require caution during handling.
Acetidic acid has a sharp, acidic taste, and due to its two closely spaced acidic protons, it exhibits polyprotic behavior, with two dissociation constants (pKa₁ ≈ 2.83 and pKa₂ ≈ 5.69), making it useful in buffer solutions and pH control systems in chemical processes.

Uses of Acetidic Acid:
Acetidic acid is a precursor to specialty polyesters.
Acetidic acid can be converted into 1,3-propanediol for use in polyesters and polymers (whose usefulness is unclear though).
Acetidic acid can also be a component in alkyd resins, which are used in a number of coatings applications for protecting against damage caused by UV light, oxidation, and corrosion.

One application of Acetidic acid is in the coatings industry as a crosslinker for low-temperature cure powder coatings, which are becoming increasingly valuable for heat sensitive substrates and a desire to speed up the coatings process.
The global coatings market for automobiles was estimated to be $18.59 billion in 2014 with projected combined annual growth rate of 5.1% through 2022.

Acetidic acid is used in a number of manufacturing processes as a high value specialty chemical including the electronics industry, flavors and fragrances industry, specialty solvents, polymer crosslinking, and pharmaceutical industry.
In 2004, annual global production of Acetidic acid and related diesters was over 20,000 metric tons.

Potential growth of these markets could result from advances in industrial biotechnology that seeks to displace petroleum-based chemicals in industrial applications.
In 2004, Acetidic acid was listed by the US Department of Energy as one of the top 30 chemicals to be produced from biomass.

Acetidic acid may be used as a cross-linking agent between corn starch and potato starch to improve Acetidic acid mechanical properties.
Acetidic acid is used in organic intermediates of vitamin B1, B2, B6 and spices, adhesives, resin additives, Acetidic acid can be used for electroplating polishing compound and welding fluxing additive, etc.

Acetidic acid may be used as a cross-linking agent between corn starch and potato starch to improve Acetidic acid mechanical properties.
Acetidic acid is also frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum" s acid.
The esters of Acetidic acid are also used as a −CH2COOH synthon in the malonic ester synthesis.

Acetidic acid may be used as a cross-linking agent between corn starch and potato starch to improve Acetidic acid mechanical properties.
In food and drug applications, Acetidic acid can be used to control acidity, either as an excipient in pharmaceutical formulation or natural preservative additive for foods.

Acetidic acid is used as a building block chemical to produce numerous valuable compounds, including the flavor and fragrance compounds gamma-nonalactone, cinnamic acid, and the pharmaceutical compound valproate.
Acetidic acid has been used to cross-link corn and potato starches to produce a biodegradable thermoplastic; the process is performed in water using non-toxic catalysts.

Starch-based polymers comprised 38% of the global biodegradable polymers market in 2014 with food packaging, foam packaging, and compost bags as the largest end-use segments.

Related Chemicals of Acetidic Acid:
The fluorinated version of Acetidic acid is difluoroAcetidic acid.
Acetidic acid is diprotic; that is, Acetidic acid can donate two protons per molecule.

Acetidic acid's first is 2.8 and the second is 5.7.
Thus the malonate ion can be HOOCCH2COO− or CH2(COO)2−2.
Malonate or propanedioate compounds include salts and esters of Acetidic acid, such as Diethyl malonate, Dimethyl malonate, Disodium malonate, Malonyl-CoA.

Structure and Preparation of Acetidic Acid:
The structure of Acetidic acid has been determined by X-ray crystallography and extensive property data including for condensed phase thermochemistry are available from the National Institute of Standards and Technology.
A classical preparation of Acetidic acid starts from chloroacetic acid:

Preparation of Acetidic Acid:
Sodium carbonate generates the sodium salt, which is then reacted with sodium cyanide to provide the sodium salt of cyanoacetic acid via a nucleophilic substitution.
The nitrile group can be hydrolyzed with sodium hydroxide to sodium malonate, and acidification affords Acetidic acid.

Industrially, however, Acetidic acid is produced by hydrolysis of dimethyl malonate or diethyl malonate.
Acetidic acid has also been produced through fermentation of glucose.

Organic Reactions of Acetidic Acid:
Acetidic acid reacts as a typical carboxylic acid: forming amide, ester, anhydride, and chloride derivatives.
Malonic anhydride can be used as an intermediate to mono-ester or amide derivatives, while malonyl chloride is most useful to obtain diesters or diamides.

In a well-known reaction, Acetidic acid condenses with urea to form barbituric acid.
Acetidic acid may also be condensed with acetone to form Meldrum's acid, a versatile intermediate in further transformations.
The esters of Acetidic acid are also used as a −CH2COOH synthon in the malonic ester synthesis.

Mitochondrial Fatty Acid Synthesis of Acetidic Acid:
Acetidic acid is the starting substrate of mitochondrial fatty acid synthesis (mtFASII), in which Acetidic acid is converted to malonyl-CoA by malonyl-CoA synthetase (ACSF3).

Additionally, the coenzyme A derivative of malonate, malonyl-CoA, is an important precursor in cytosolic fatty acid biosynthesis along with acetyl CoA.
Malonyl CoA is formed there from acetyl CoA by the action of acetyl-CoA carboxylase, and the malonate is transferred to an acyl carrier protein to be added to a fatty acid chain.

Briggs–Rauscher reaction:
Acetidic acid is a key component in the Briggs–Rauscher reaction, the classic example of an oscillating chemical reaction.
Knoevenagel condensation
In Knoevenagel condensation, Acetidic acid or its diesters are reacted with the carbonyl group of an aldehyde or ketone, followed by a dehydration reaction.

Z=COOH (Acetidic acid) or Z=COOR' (malonate ester)
When Acetidic acid itself is used, Acetidic acid is normally because the desired product is one in which a second step has occurred, with loss of carbon dioxide, in the so-called Doebner modification.

The Doebner modification of the Knoevenagel condensation.
Thus, for example, the reaction product of acrolein and Acetidic acid in pyridine is trans-2,4-Pentadienoic acid with one carboxylic acid group and not two.

Preparation of carbon suboxide:
Carbon suboxide is prepared by warming a dry mixture of phosphorus pentoxide (P4O10) and Acetidic acid.
Acetidic acid reacts in a similar way to malonic anhydride, forming malonates

Pathology of Acetidic Acid:
If elevated Acetidic acid levels are accompanied by elevated methylAcetidic acid levels, this may indicate the metabolic disease combined malonic and methylAcetidic aciduria (CMAMMA).
By calculating theAcetidic acid to methylAcetidic acid ratio in blood plasma, CMAMMA can be distinguished from classic methylmalonic academia.

Biochemistry of Acetidic Acid:
Acetidic acid is the classic example of a competitive inhibitor of the enzyme succinate dehydrogenase (complex II), in the respiratory electron transport chain.
Acetidic acid binds to the active site of the enzyme without reacting, competing with the usual substrate succinate but lacking the −CH2CH2− group required for dehydrogenation.

This observation was used to deduce the structure of the active site in succinate dehydrogenase.
Inhibition of this enzyme decreases cellular respiration.
Since Acetidic acid is a natural component of many foods, Acetidic acid is present in mammals including humans.

History of Acetidic Acid:
Acetidic acid is a naturally occurring substance found in many fruits and vegetables.
There is a suggestion that citrus fruits produced in organic farming contain higher levels of Acetidic acid than fruits produced in conventional agriculture.
Acetidic acid was first prepared in 1858 by the French chemist Victor Dessaignes via the oxidation of malic acid.

Handling and Storage of Acetidic Acid:

Conditions for safe storage, including any incompatibilities:

Storage conditions:
Tightly closed.
Dry.

Storage class:
Storage class (TRGS 510): 13
Non Combustible Solids

Stability and Reactivity of Acetidic Acid:

Chemical stability:
Acetidic acid is chemically stable under standard ambient conditions (room temperature).

First Aid Measures of Acetidic Acid:

General advice:
Show this material safety data sheet to the doctor in attendance.

If inhaled:

After inhalation:
Fresh air.

In case of skin contact:
Take off immediately all contaminated clothing.
Rinse skin with water/ shower.

In case of eye contact:

After eye contact:
Rinse out with plenty of water.
Immediately call in ophthalmologist.
Remove contact lenses.

If swallowed:

After swallowing:
Immediately make victim drink water (two glasses at most).
Consult a physician.

Indication of any immediate medical attention and special treatment needed:
No data available

Fire Fighting Measures of Acetidic Acid:

Suitable extinguishing media:
Water
Foam
Carbon dioxide (CO2)
Dry powder

Unsuitable extinguishing media:
For this substance/mixture no limitations of extinguishing agents are given.

Further information:
Prevent fire extinguishing water from contaminating surface water or the ground water system.

Accidental Release Measures of Acetidic Acid:

Environmental precautions:
Do not let product enter drains.

Methods and materials for containment and cleaning up:
Cover drains.
Collect, bind, and pump off spills.

Observe possible material restrictions.
Take up dry.

Dispose of properly.
Clean up affected area.

Exposure Controls/Personal Protection of Acetidic Acid:

Personal protective equipment:

Eye/face protection:
Use equipment for eye protection.
Tightly fitting safety goggles.

Skin protection:

Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

Splash contact:
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min

Body Protection:
protective clothing

Respiratory protection:

Recommended Filter type:
Filter type P2

Control of environmental exposure:
Do not let product enter drains.

Identifiers of Acetidic Acid:
SMILES: O=C(O)CC(O)=O
C(C(=O)O)C(=O)O
Chemical formula: C3H4O4
Molar mass: 104.061 g·mol−1
Density: 1.619 g/cm3
Melting point: 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point: decomposes
Solubility in water: 763 g/L
Acidity (pKa): pKa1 = 2.83
pKa2 = 5.69
Magnetic susceptibility (χ): -46.3·10−6 cm3/mol
Chemical Formula: C3H4O4
Average Molecular Weight: 104.0615
Monoisotopic Molecular Weight: 104.010958616
IUPAC Name: propanedioic acid
Traditional Name: Acetidic acid

CAS Registry Number: 141-82-2
SMILES: OC(=O)CC(O)=O
InChI Identifier: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
InChI Key: OFOBLEOULBTSOW-UHFFFAOYSA-N
Molecular Weight: 104.06100
Exact Mass: 104.06
EC Number: 205-503-0
UNII: 9KX7ZMG0MK
ICSC Number: 1085
NSC Number: 8124
DSSTox ID: DTXSID7021659
Color/Form: White crystals|Crystalline powder
Colorless hygroscopic solid which sublimes in vacuum
HScode: 2917190090
PSA: 74.60000
XLogP3: -0.8
Appearance: Acetidic acid appears as white crystals or crystalline powder. Sublimes in vacuum.

Henry's Law constant = 4.8X10-13 atm-cu m/mole at 23 °C (estimated from vapor pressure and water solubility)
Hydroxyl radical reaction rate constant = 1.6X10-12 cu-cm/molc sec at 25 °C (est)
Air and Water Reactions: Water soluble.
Reactive Group: Acids, Carboxylic
Heat of Combustion: Molar heat of combustion: 864 kJ/mol
Heat of Vaporization: 92 kJ/mol
Critical Temperature & Pressure:
Critical temperature: 805 K (estimated);
critical pressure: 5640 kPa (estimated)
CAS: 141-82-2
Molecular Formula: C3H4O4
Molecular weight: 104.06
EINECS: 205-503-0

n-octanol/water: log Pow: -0,81 - Bioaccumulation is not expected.
Vapor pressure: 0,002 hPa at 25 °C
Density: 1,6 g/cm3
Relative density: 1,03 at 20 °C
Oxidizing properties: none
CAS Number: 141-82-2
InChI: InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
Key: OFOBLEOULBTSOW-UHFFFAOYSA-N
InChI=1/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
Key: OFOBLEOULBTSOW-UHFFFAOYAJ

Physical Appearance: A solid
Storage: Store at -20°C
M.Wt: 104.06
Cas No.: 141-82-2
Formula: C3H4O4
Solubility: ≥10.4 mg/mL in DMSO; ≥104 mg/mL in H2O; ≥119.8 mg/mL in EtOH
Chemical Name: Acetidic acid
Canonical SMILES: O=C(O)CC(O)=O
Shipping Condition: Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice.
CAS Number: 141-82-2
Molecular Weight: 104.06
Beilstein: 1751370
MDL number: MFCD00002707
Molecular Weight: 104.06 g/mol
XLogP3: -0.8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2

Properties of Acetidic Acid:
Exact Mass: 104.01095860 g/mol
Monoisotopic Mass: 104.01095860 g/mol
Topological Polar Surface Area: 74.6Ų
Heavy Atom Count: 7
Complexity: 83.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes
Physical state: powder
Color: white
Odor: odorless

Density: 1.6 g/cm3
Melting Point: 135 °C (decomp)
Boiling Point: 215 °C @ Press: 14 Torr
Flash Point: 201.9ºC
Refractive Index: 1.479
Water Solubility: H2O: 1400 g/L (20 ºC)
Storage Conditions: Store at RT.
Vapor Pressure: 4.66E-07mmHg at 25°C
PKA: 2.85(at 25 °C)
Dissociation Constants: 2.85 (at 25 °C)|pKa1 = 2.8, pKa2 = 5.7 at 25 °C
Experimental Properties:
Enthalpy of Sublimation: 72.7 kJ/mol at 306 deg K, 108.0 kJ/mol at 348 deg K

Melting point/freezing point:
Melting point: >= 135 °C
Initial boiling point and boiling range: 215 °C at 18,66 hPa (decomposition)
Flammability (solid, gas): The product is not flammable.
Upper/lower flammability or explosive limits: No data available
Flash point: 157 °C - c.c.
Autoignition temperature: No data available
Decomposition temperature: > 140 °C
pH: No data available
Viscosity
Viscosity, kinematic: No data available
Viscosity, dynamic: No data available
Water solubility 766 g/l at 20 °C

Purity: ≥99%
Appearance: White crystal powder
Melting point: 132-135 °C (dec.) (lit.)
Boiling point: 140ºC(decomposition)
Density: 1.619 g/cm3 at 25 °C
Refractive index: 1.478
Flash Point: 157°C
Storage condition: Sealed in dry,Room Temperature
Solubility : 1 M NaOH: soluble100mg/mL, clear to slightly hazy, colorless to faintly yellow
Pka: 2.83(at 25ºC)
Stability: Stable.
Incompatible with oxidizing agents, reducing agents, bases.
HS Code: 29171910

PH: 3.17(1 mM solution);2.5(10 mM solution);
1.94(100 mM solution)
MDL: MFCD00002707
Water Solubility: 1400 g/L (20 ºC)
Vapor Presure: 0-0.2Pa at 25ºC
Physical and Chemical Properties:
Character: white crystal.
soluble in water, soluble in ethanol and ether, pyridine.
Color: White
Formula Weight: 104.1
Percent Purity: 0.99
Physical Form: Powder
Chemical Name or Material: Acetidic acid
Melting point: 132-135 °C (dec.) (lit.)
Boiling point: 140℃（decomposition）

Density: 1.619 g/cm3 at 25 °C
vapor pressure: 0-0.2Pa at 25℃
refractive index: 1.4780
Flash point: 157°C
storage temp.: Sealed in dry,Room Temperature
solubility: 1 M NaOH: soluble100mg/mL, clear to slightly hazy, colorless to faintly yellow
form: Liquid
pka: 2.83(at 25℃)
color: White
PH: 3.17(1 mM solution);2.5(10 mM solution);1.94(100 mM solution)
Water Solubility: 1400 g/L (20 ºC)
Merck: 14,5710
BRN: 1751370
Stability: Stable.
Incompatible with oxidizing agents, reducing agents, bases.
InChIKey: OFOBLEOULBTSOW-UHFFFAOYSA-N

LogP: -0.81
CAS DataBase Reference: 141-82-2(CAS DataBase Reference)
EWG's Food Scores: 1
FDA UNII: 9KX7ZMG0MK
NIST Chemistry Reference: Acetidic acid(141-82-2)
EPA Substance Registry System: Propanedioic acid (141-82-2)
Molecular Weight: 104.06 g/mol
XLogP3: -0.8
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Rotatable Bond Count: 2
Exact Mass: 104.01095860 g/mol
Monoisotopic Mass: 104.01095860 g/mol
Topological Polar Surface Area: 74.6Ų
Heavy Atom Count: 7
Complexity: 83.1
Isotope Atom Count: 0
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Covalently-Bonded Unit Count: 1
Compound Is Canonicalized: Yes

Chemical formula: C3H4O4
Molar mass: 104.061 g·mol−1
Density: 1.619 g/cm3
Melting point: 135 to 137 °C (275 to 279 °F; 408 to 410 K) (decomposes)
Boiling point: decomposes
Solubility in water: 763 g/L
Acidity (pKa): pKa1 = 2.83
pKa2 = 5.69
Magnetic susceptibility (χ): -46.3·10−6 cm3/mol

Related compounds of Acetidic Acid:
Malondialdehyde
Dimethyl malonate

Other anions:
Malonate

Related carboxylic acids:
Oxalic acid
Propionic acid
Succinic acid
Fumaric acid

Names of Acetidic Acid:

Preferred IUPAC name:
Propanedioic acid

Other names:
Methanedicarboxylic acid