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75-07-0

Basic Information
CAS No.: 75-07-0
Name: Acetaldehyde
Article Data: 3149
Cas Database
Molecular Structure:
Molecular Structure of 75-07-0 (Acetaldehyde)
Formula: C2H4O
Molecular Weight: 44.0532
Synonyms: Aceticaldehyde;Ethanal;Ethyl aldehyde;NSC 7594;
EINECS: 200-836-8
Density: 0.748 g/cm3
Melting Point: -123 °C
Boiling Point: 18.588 °C at 760 mmHg
Flash Point: 133°F
Solubility: > 500 g/L (20 °C) in water
Appearance: clear, colorless liquid
Hazard Symbols: HighlyF+, HarmfulXn, FlammableF, ToxicT
Risk Codes: 23/24/25-34-40-43-36/37-12-67-11-41-22-10
Safety: 36/37-33-16-26
Transport Information: UN 1198 3/PG 3
PSA: 17.07000
LogP: 0.20520
Synthetic route
64-17-5

ethanol

75-07-0

acetaldehyde

Conditions
ConditionsYield
With CuO2H at 45℃; for 4h; under 30W sonication;100%
With PQQTME; calcium perchlorate; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile Oxidation;100%
With oxygen; iron(III) perchlorate; ozone Kinetics; Reagent/catalyst; Concentration;100%
74-85-1

ethene

75-07-0

acetaldehyde

Conditions
ConditionsYield
With bis(benzonitrile)palladium(II) dichloride; py.Co(N,N'-bis(alicylidene-o-phenylene)diamino).NO2 In tetrahydrofuran at 50℃; under 760 Torr; for 0.916667h;100%
With bis(benzonitrile)palladium(II) dichloride; py.Co(N,N'-bis(alicylidene-o-phenylene)diamino).NO2 In tetrahydrofuran at 50℃; under 760 Torr; for 0.916667h; Product distribution; influence of Pd/Co ratio, solvent, further olefins;100%
With aluminum(III) sulfate; water at 350 - 360℃;
108-05-4

vinyl acetate

100-51-6

benzyl alcohol

A

140-11-4

Benzyl acetate

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
With 1,3-dicyclohexylimidazolium-2-thiocarboxylate In tetrahydrofuran at 80℃; for 2h; Inert atmosphere;A 100%
B n/a
With lipase from Pseudomonas Cepacia In benzene at 35℃; other ω-substituted-1-alkanols, var. solvents; kinetic parameters of transesterification;
16457-30-0

hydridopentacarbonylrhenium(I)

pentacarbonyl(methyl)manganese(I)

2206-26-0

[D3]acetonitrile

A

98688-79-0

(CO)5ReMn(CO)4(C(2)H3CN)

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
In [D3]acetonitrile MeMn(CO)5, CD3CN, and HRe(CO)5 were vac. transferred into an NMR tube, the tube was sealed, thawed, and rapidly placed in the instrument probe (ca. 30°C), reaction was complete within 35 min; followed by (1)H NMR, MeCHO was identified by (1)H NMR, (CO)5ReMn(CO)4(CD3CN) was isolated by preparative layer chromy. on SiO2 followed by recrystn. from CH2Cl2/hexanes (ca. 1:3) at -25°C; elem. anal.;A 62%
B 100%

pentacarbonyl(methyl)manganese(I)

A

33292-90-9

Os(CO)4(Mn(CO)5)2

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
In [D3]acetonitrile MeMn(CO)5, H2Os(CO)4 (2:1 molar ratio), and CD3CN were sealed in a NMR tube under vac., the tube was thawed, reaction was complete in 70 min; monitored by (1)H NMR, yield of MeCHO was detd. by integration of the corresponding peak in the (1)H NMR spectrum, Mn2Os(CO)14 was identified by its IR and mass spectra;A n/a
B 100%
With carbon monoxide In tetrahydrofuran MeMn(CO)5 and H2Os(CO)4 (2:1 molar ratio) in THF were reacted overnightat room temp. (IR spectrum showed the presence of MeCHO), soln. was frozen, degassed, and CO (2 atm) admitted, reaction was stirred overnight at room temp.; product was isolated via preparative layer chromy.;A 68%
B n/a
With carbon monoxide In acetonitrile MeMn(CO)5, H2Os(CO)4 (2:1 molar ratio), and MeCN were reacted for 8 h at room temp., solvent was removed under vac., residue taken up in CH2Cl2, soln. was frozen, degassed, and CO (2 atm) admitted, reaction was stirred for 32 h in the dark at room temp.; product was isolated via preparative layer chromy.;A 62%
B n/a
75-05-8

acetonitrile

75-07-0

acetaldehyde

Conditions
ConditionsYield
With potassium carbonate In water; dimethyl sulfoxide at 60℃; for 8h; High pressure; Green chemistry;99.9%
With tin(ll) chloride
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; triethylamine Quantum yield; Product distribution; Mechanism; Irradiation; further metal-complexes;
108-05-4

vinyl acetate

4407-36-7

(2E)-3-phenyl-2-propen-1-ol

A

21040-45-9

Cinnamyl acetate

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
[(nBuSn)12(μ3-O)14(μ2-OH)6](2+)*2(2,5-Me2C6H3SO3(1-)) at 75℃; for 4.5h;A 99%
B n/a

(H2O)5CrCH(CH3)OH(2+)

A

chromium (III) ion

B

75-07-0

acetaldehyde

Conditions
ConditionsYield
With Fe(3+) In ethanol; water Kinetics; byproducts: H(1+); excess of Fe(3+) in 1 M aq. EtOH at 24.8°C under N2 by controlled ionic strength;A n/a
B 99%
With Cu(2+) In ethanol; water Kinetics; byproducts: H(1+); excess of Cu(2+) in 1 M aq. EtOH at 24.8°C under N2 by controlled ionic strength;A n/a
B >99
542-10-9

ethylidene diacetate

75-07-0

acetaldehyde

Conditions
ConditionsYield
With ethanol at 50℃; for 0.166667h; chemoselective reaction;98%
durch thermische Zersetzung;
durch thermische Zersetzung;

NiMe2(PEt3)2

A

16787-33-0

(CO)2Ni(P(C2H5)3)2

B

75-07-0

acetaldehyde

C

431-03-8

dimethylglyoxal

D

67-64-1

acetone

Conditions
ConditionsYield
With carbon monoxide In diethyl ether Et2O soln. of Ni complex stirred under CO at -78°C for 0.2 h, warmed to room temp.; drying up; GLC anal.;A n/a
B 0%
C 0%
D 98%
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History

Acetaldehyde was first prepared by Scheele in 1774, by the action of manganese dioxide (MnO2) and sulfuric acid (H2SO4) on ethyl alcohol (ethanol, CH3CH2OH).
The formation of acetaldehyde by the addition of water to acetylene was observed by Kutscherow in 1881.

Specification

The Acetaldehyde, with the CAS registry number 75-07-0 and EINECS registry number 200-001-8, is a kind of colourless clear liquid with the molecular formula of C2H4O. It is one of the most important aldehydes, occurring widely in nature and being produced on a large scale industrially. Acetaldehyde can be found naturally in coffee, bread, and ripe fruit, and it is produced by plants as part of their normal metabolism.

The physical properties of Acetaldehyde are as followings: (1)# of Rule of 5 Violations: 0; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 20.875; (5)ACD/KOC (pH 7.4): 20.875; (6)#H bond acceptors: 1; (7)#H bond donors: 0; (8)#Freely Rotating Bonds: 0; (9)Polar Surface Area: 17.07 Å2; (10)Index of Refraction: 1.315; (11)Molar Refractivity: 11.501 cm3; (12)Molar Volume: 58.868 cm3; (13)Polarizability: 4.56×10-24cm3; (14)Surface Tension: 17.618 dyne/cm; (15)Density: 0.748 g/cm3; (16)Enthalpy of Vaporization: 25.76 kJ/mol; (17)Boiling Point: 18.588 °C at 760 mmHg; (18)Vapour Pressure: 964.536 mmHg at 25°C.

Preparation: The main production method is the oxidation of ethylene via the Wacker process:
2CH2=CH2+O2 → 2CH3CHO

Uses: It is usually used as a precursor to acetic acid, but this application has declined because it can be made more efficiently from methanol by the Monsanto and Cativa processes. And in terms of condensation reactions, acetaldehyde is an important precursor to pyridine derivatives, pentaerythritol, and crotonaldehyde.

You should be cautious while dealing with this chemical. It is a kind of extremely flammable chemical which irritates to eyes and respiratory system. And there's limited evidence of a carcinogenic effect. Therefore, you had better take the following instructions: Keep away from sources of ignition - No smoking; Wear suitable protective clothing and gloves; Take precautionary measures against static discharges.

You can still convert the following datas into molecular structure:
(1)SMILES: CC=O
(2)InChI: InChI=1/C2H4O/c1-2-3/h2H,1H3
(3)InChIKey: IKHGUXGNUITLKF-UHFFFAOYAB

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LDLo intravenous 800mg/kg (800mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

CARDIAC: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 30, Pg. 429, 1927.
hamster LC50 inhalation 17000ppm/4H (17000ppm)   Progress in Experimental Tumor Research. Vol. 24, Pg. 162, 1979.
hamster LD50 intratracheal 96mg/kg (96mg/kg)   Progress in Experimental Tumor Research. Vol. 24, Pg. 162, 1979.
human TCLo inhalation 134ppm/30M (134ppm) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES JAMA, Journal of the American Medical Association. Vol. 165, Pg. 1908, 1957.
mammal (species unspecified) LC50 inhalation 20100mg/m3 (20100mg/m3) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 19(7), Pg. 54, 1975.
mouse LC50 inhalation 23gm/m3/4H (23000mg/m3)   Current Toxicology. Vol. 1, Pg. 47, 1993.
mouse LD50 intraperitoneal 500mg/kg (500mg/kg)   IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. Vol. 36, Pg. 101, 1985.
mouse LD50 oral 900mg/kg (900mg/kg)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(11), Pg. 57, 1981.
mouse LD50 subcutaneous 560mg/kg (560mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 299, 1950.
rabbit LD50 skin 3540mg/kg (3540mg/kg)   Union Carbide Data Sheet. Vol. 12/13/1963,
rabbit LDLo intravenous 300mg/kg (300mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 30, Pg. 429, 1927.
rabbit LDLo subcutaneous 1200mg/kg (1200mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 30, Pg. 429, 1927.
rat LC50 inhalation 13300ppm/4H (13300ppm) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
National Technical Information Service. Vol. OTS0534485,
rat LD50 oral 661mg/kg (661mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Agents and Actions, A Swiss Journal of Pharmacology. Vol. 4, Pg. 125, 1974.
rat LD50 subcutaneous 640mg/kg (640mg/kg) BEHAVIORAL: GENERAL ANESTHETIC Acta Pharmacologica et Toxicologica. Vol. 6, Pg. 299, 1950.
rat LDLo intraperitoneal 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Journal of Biological Chemistry. Vol. 152, Pg. 41, 1944.