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Acetaldehyde
Cas No: 75-07-0
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Acetaldehyde
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Acetaldehyde CAS#75-07-0
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Acetaldehyde
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Amadis Chemical offer CAS#75-07-0;CAT#A838317
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Acetaldehyde
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Acetaldehyde
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Natural Acetaldehyde
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Acetaldehyde CAS NO.75-07-0
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75-07-0 Usage

Uses

Acetaldehyde is used as intermediate for syntheses of bulk chemicals, e.g. ethyl acetate, acetic acid, acetic anhydride, isooctylalcohol, pentaerythrite, pyridines, etc. For specific dyes, e.g. C.I. 46040 Basic Yellow 9. Product Data Sheet

Health Hazard

Breathing vapors will be irritating and may cause nausea, vomiting, headache, and unconsciousness. Contact with eyes may cause burns and eye damage. Skin contact from clothing wet with the chemical causes burns or severe irritation.
Acetaldehyde enters your body when you breathe air containing it. It can also enter your body when you eat food or drink liquid containing acetaldehyde. When you drink alcohol, your body makes acetaldehyde when it processes the alcohol.
The effect of acetaldehyde on your health depends on how much is in your body, how long you were exposed, and how often you were exposed. The way it affects you will also depend on your health. Another factor is the condition of the environment when you were exposed.
Breathing acetaldehyde for short periods can hurt your lungs. Acetaldehyde can also hurt your heart and blood vessels.
Contact with acetaldehyde liquid or vapor can hurt the skin and eyes.
It is not known if breathing, drinking or eating small amounts of acetaldehyde over long periods will hurt you. Some animal studies show that acetaldehyde can hurt a growing fetus. Other studies on animals show that breathing acetaldehyde can severely damage the lungs and cause cancer. Repeated exposure to acetaldehyde in the air may cause cancer in humans.
When you drink alcohol, your liver turns acetaldehyde into an acid. Some of the acetaldehyde enters your blood, damaging your membranes and possibly causing scar tissue. It also leads to a hangover, and can result in a faster heartbeat, a headache or an upset stomach.
The brain is most affected by acetaldehyde poisoning. It causes problems with brain activity and can impair memory. Acetaldehyde can cause amnesia, which is the inability to remember things. This is a common effect for people who drink too much alcohol.

Preparation

Several production methods are used to produce ethanal.
(1) Direct oxidation of ethylene.
Ethylene and oxygen passed the catalysts containing palladium chloride, copper chloride, hydrochloric acid and water .Coarse acetaldehyde can be synthesyed by this one-Step direct oxidation process. Then, after a distillation process, the final product was obtained.
(2) Ethanol oxidation.
Under the 300-480 ℃, the air oxydehydrogenation process of ethanol vapor took place to produce acetaldehyde by using silver, copper or silver-copper alloy mesh as catalyst.
(3) Direct hydration of ethyne.
Under the effect of mercury catalyst or mercury free catalyst, the direct hydration reaction of acetylene and water was used to produce acetaldehyde. Due to the toxicity of mercury, this method has been gradually replaced by other methods.
(4) Ethanol dehydrogenation
Under the effect of copper catalyst with the addition of cobalt, chromium, zinc or other compounds, ethanol dehydrogenation took place to produce acetaldehyde.
(5) Saturated hydrocarbon oxidation.
Material Consumption Quota: one ton product of acetaldehyde costs 610kg ethyne(99%) by direct hydration of ethyne method; 1200kg ethanol (95%) by ethanol oxidation method; 710kg ethylene(99%) and 300m3 oxygen(99%) by ethylene oxidation method (one-step).
(6) Acetaldehyde can be prepared by ethylene oxidation.
Acetaldehyde can be prepared by gas phase hydrogenation of Ethanol.
Acetaldehyde can be prepared by simultaneous destructive distillation calcium acetate and calcium formate.
ethanal can be prepared by adduct reaction of acetylene and water.

Description

Acetaldehyde is a highly flammable, volatile colourless liquid. It has a characteristic, pungent, and suffocating odour and is miscible in water. Acetaldehyde is ubiquitous in the ambient environment. It is an intermediate product of higher plant respiration and formed as a product of incomplete wood combustion in fireplaces and woodstoves, burning of tobacco, vehicle exhaust fumes, coal refining, and waste processing. Exposures to acetaldehyde occur during the production of acetic acid and various other industrial chemical substances, for instance, manufacture of drugs, dyes, explosives, disinfectants, phenolic and urea resins, rubber accelerators, and varnish.

Purification Methods

Acetaldehyde is usually purified by fractional distillation in a glass helices-packed column under dry N2, discarding the first portion of distillate. Or, it is shaken for 30minutes with NaHCO3, dried with CaSO4 and fractionally distilled at 760mm through a 70cm Vigreux column (p 11). The middle fraction is collected and further purified by standing for 2hours at 0o with a small amount of hydroquinone (free radical inhibitor), followed by distillation [Longfield & Walters J Am Chem Soc 77 810 1955]. [Beilstein 1 IV 3094.]

Definition

ChEBI: The aldehyde formed from acetic acid by reduction of the carboxy group. It is the most abundant carcinogen in tobacco smoke.

Uses

  1. Acetaldehyde can also be used as an odorant, and it found in nature in many foods such as ripe fruits, cheese and heated milk. acetaldehyde occurs naturally during fermentation, and low levels of acetaldehyde are to be found in certain foods. It is mainly used for preparation of citrus, apple, cream type essence, etc.
  2. Acetaldehyde is mostly used in acetic acid industry. Butanol and octanol are also the important derivatives of the acetaldehyde in the past. Nowadays, butanol and octanol are prepared by Propylene carbonyl synthesis method.
  3. Acetaldehyde is a very important raw material in the production of a large number of chemical products, for example paint binders in alkyd paints and plasticizers for plastics. Acetaldehyde is also used in the manufacture of construction materials, fire retardant paints and explosives, while its uses within the pharmaceutical industry include the manufacture of sedatives and tranquilisers, among other things. Acetaldehyde can also be used as a raw material in the manufacture of acetic acid, another platform chemical with many applications.
  4. Acetaldehyde is also used to produce pentaerythritol, peracetic acid, pyridine and its derivatives. Domestically produced acetaldehyde is mainly used as intermediate for the production of acetic acid. Only a small amount is used for the production of pentaerythritol, butanol, trichloroacetaldehyde, trimethylolpropane, etc.
  5. Acetaldehyde is primarily used to produce other chemicals, including acetal, Crotonaldehyde, acetic acid peroxide, hydroxyl acrylic nitrile, trichloroacetaldehyde, ethyl acetate, pentaerythritol, acetic anhydride, acetic acid, Glyoxal, phenyl acrolein, acetal, methyl ethylamine  , diethylamine, α-Alanine, pyridine, α-methylpyridine, β-methylpyridine, γ-methylpyridine, etc.

description

Acetaldehyde, also called ethanal, is the simplest aldehyde (CH3CHO). Acetaldehyde is a colourless and volatile liquid made by the catalytic oxidation of ethanol, with a sharp and fruity odour.It is widely used industrially as a chemical intermediate.Acetaldehyde is also a metabolite of sugars and ethanol in humans,is found naturally in the environment, and is a product of biomass combustion.
Acetaldehyde is primarily used as an intermediate in the manufacture of a range of chemicals, perfumes, aniline dyes, plastics and synthetic rubber and in some fuel compounds. Acetaldehyde is an important reagent used in the manufacture of dyes, plastics, and many other organic chemicals.
In the presence of acids it forms the cyclic polymers paraldehyde (CH3CHO)3, and metaldehyde (CH3CHO)4. The former is used as a hypnotic, and the latter as a solid fuel for portable stoves and as a poison for snails and slugs.
Acetaldehyde is also used in the manufacture of disinfectants, drugs, perfumes, explosives, lacquers and varnishes, photographic chemicals, phenolic and urea resins, rubber accelerators and antioxidants, and room air deodourizers. It is also used as a synthetic flavouring substance, food preservative and as a fragrance.
Acetaldehyde 2d structural formula
figure 1 Acetaldehyde 2d structural formula

Uses

manufacture of paraldehyde, acetic acid, butanol, perfumes, flavors, aniline dyes, plastics, synthetic rubber; silvering mirrors, hardening gelatin fibers. Flavoring agent in foods and beverages. Fumigant for storage of apples and strawberries.

Contact allergens

Acetaldehyde, as its metabolite, is responsible for many of the effects of ethanol, such as hepatic or neurological toxicity. A case of contact allergy was reported in the textile industry, where dimethoxane was used as a biocide agent in textiles, and its degradation led to acetaldehyde

Air & Water Reactions

Highly flammable. Easily oxidized by air to form unstable peroxides which may explode. Forms explosive mixture with air above 100°C (30-60% of the vapor in air) owing to formation of peroxyacetic acid [White, A. G. et al., J. Soc. Chem. Ind., 1950, 69, p. 206]. Soluble in water.

Hazardous Substances Data Bank (HSDB)

Acetaldehyde has been classified by the International Agency for Research on Cancer (IARC) as Group 2B, possibly carcinogenic to humans, based on evidence in animals.Acetaldehyde is a respiratory tract carcinogen in experimental animals, especially of the nasal mucosa in rats and of the larynx in hamsters.
There is inadequate evidence for the carcinogenicity of acetaldehyde in humans. One small study of workers manufacturing several types of aldehydes found increased risk of bronchial tumours, but workers were exposed to many other chemicals in addition to acetaldehyde.Three other studies on the carcinogenicity of alcoholic beverages found that people who developed cancer after heavy alcohol use had genetic differences and higher concentrations of acetaldehyde in their blood compared to those who didn't develop cancer.Further study is required to establish a causal relationship.
Acetaldehyde can cause respiratory and eye irritation and in severe cases, lung edema. It also exacerbates the effects of alcohol and is a central nervous system depressant.

Content analysis

65 ml of 0.5 mol/L hydroxylamine hydrochloride and 50.0 ml of triethanolamine were added to a fixed pressure-heat resistant bottle with good sealing property. A slow nitrogen flow is fed into the bottle through a glass tube slightly above the liquid surface for 2 min to exhaust the air. About 600 mg of the sample, accurately weighed, was sealed in one ampoule bottle and put in the above mixture. Several short glass rods with the diameter of about 8 mm were added to the bottle. After covering the cork, the bottle was strongly shaken to break the ampoule. Then keep the reaction for 30 min at room temperature, shaking the bottle from time to time. Remove the cork after cooling if necessary. The whole process should be careful in order to avoid the loss of the product. The above system was then titrated by certain amount of 0.5 mol/L sulfuric acid to cyan end point. At the same time a blank titration was conducted. Each 0.5 mol/L sulfur acid was equivalent to 22.03 mg acetaldehyde (C2H4O).

As a flavor ingredient

Identification:
CAS.No.:  75-07-0  FL.No.:  5.001 FEMA.No.:  2003 NAS.No.:  2003
CoE.No.:  89 EINECS.No.:  200-836-8 JECFA.No.:  80    
Regulatory Status:
CoE: Approved. Bev.: 23 ppm; Food: 20 ppm
FDA: 21 CFR 182.60, 582.60; 27 CFR 19.460, 21 et seq.
FDA (other): n/a
JECFA: ADI: Acceptable. No safety concern at current levels of intake when used as a flavoring agent (1997).

Reported uses (ppm): (FEMA, 1994)
Food Category  Usual  Max. 
Alcoholic.beverages  470 470
Baked.goods  30 280
Cheese  0.0005 600
Chewing.gum  0.78 9.2
Condiment,.relish  0.5 5
Confection,.frosting  83 2000
Fats,.oils  0.1 4
Frozen.dairy  94 150
Fruit.ices  50 100
Gelatin,.pudding  8.1 100
Gravies  0.61 53
Hard.candy  9.29 21.49
Imitation.dairy  0.2 0.7
Jams,.jellies  23 50
Meat.products  1.67 5.53
Milk.products  76 76
Nonalcoholic.beverages  38 190
Reconstituted.vegetables  0.0085 0.02
Snack.foods  0.25 10
Soft.candy  3 1000
Sweet.sauce  13 230
  Natural occurrence:
Reported found in oak and tobacco leaves; in the fruital aromas of pear, apple, raspberry, strawberry and pineapple; in the distillation waters of Monarda punctata, orris, cumin, chenopodium; in the essential oils of Litsea cubeba, Magnolia grandiflora, Artemisia brevifolia, rosemary, balm, clary sage, Mentha arvensis, daffodil, bitter orange, camphor, angelica, fennel,mustard, Scotch blended whiskey, Japanese whiskey, rose wine, blackberry brandy and rum.

Uses

Acetaldehyde is used as a general solvent in organic and polymer chemical reactions. It also plays a role in fruit and food quality, ripening and deterioration.

Toxicity

GRAS(FEMA;FDA,§182.60,2000). LD501930mg/kg(rat,oral)

Reactivity Profile

Acetaldehyde undergoes a vigorously exothermic condensation reaction in contact with strong acids, bases or traces of metals. Can react vigorously with oxidizing reagents such as dinitrogen pentaoxide, hydrogen peroxide, oxygen, silver nitrate, etc. Contamination often leads either to reaction with the contaminant or polymerization, both with the evolution of heat. Can react violently with acid anhydrides, alcohols, ketones, phenols, ammonia, hydrogen cyanide, hydrogen sulfide, halogens, phosphorus, isocyanates, concentrated sulfuric acid, and aliphatic amines. Reactions with cobalt chloride, mercury(II) chlorate or perchlorate form sensitive, explosive products [Sax, 9th ed., 1996, p. 5]. An oxygenation reaction of Acetaldehyde in the presence of cobalt acetate at -20°C exploded violently when stirred. The event was ascribed to peroxyacetate formation [Phillips B. et al., J. Am. Chem. Soc., 1957, 79, p. 5982].

General Description

A clear colorless liquid with a pungent choking odor. Flash point -36°F. Boiling point 69°F. Density 6.5 lb / gal. Vapors are heaver than air and irritate the mucous membranes and especially the eyes. Used to make other chemicals.

Chemical Properties

Colourless clear liquid
InChI:InChI=1/C2H4O/c1-2-3/h2H,1H3

75-07-0 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (33244)  Acetaldehyde, 99%    75-07-0 *4x500ml 1935.0CNY Detail
Alfa Aesar (33244)  Acetaldehyde, 99%    75-07-0 500ml 547.0CNY Detail
Alfa Aesar (33244)  Acetaldehyde, 99%    75-07-0 100ml 148.0CNY Detail

75-07-0SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name acetaldehyde

1.2 Other means of identification

Product number -
Other names FORMOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. The predominant use of acetaldehyde is as an intermediate in the synthesis of other chemicals. Acetaldehyde is used in the production of perfumes, polyester resins, and basic dyes. Acetaldehyde is also used as a fruit and fish preservative, as a flavoring agent, and as a denaturant for alcohol, in fuel compositions, for hardening gelatin, and as a solvent in the rubber, tanning, and paper industries.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:75-07-0 SDS

75-07-0Synthetic route

ethanol
64-17-5

ethanol

acetaldehyde
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%
ethene
74-85-1

ethene

acetaldehyde
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℃;
vinyl acetate
108-05-4

vinyl acetate

benzyl alcohol
100-51-6

benzyl alcohol

A

Benzyl acetate
140-11-4

Benzyl acetate

B

acetaldehyde
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;
hydridopentacarbonylrhenium(I)
16457-30-0

hydridopentacarbonylrhenium(I)

pentacarbonyl(methyl)manganese(I)

pentacarbonyl(methyl)manganese(I)

[D3]acetonitrile
2206-26-0

[D3]acetonitrile

A

(CO)5ReMn(CO)4(C(2)H3CN)
98688-79-0

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

B

acetaldehyde
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)

pentacarbonyl(methyl)manganese(I)

A

Os(CO)4(Mn(CO)5)2
33292-90-9

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

B

acetaldehyde
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
acetonitrile
75-05-8

acetonitrile

acetaldehyde
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;
vinyl acetate
108-05-4

vinyl acetate

(2E)-3-phenyl-2-propen-1-ol
4407-36-7

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

A

Cinnamyl acetate
21040-45-9

Cinnamyl acetate

B

acetaldehyde
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+)

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

A

chromium (III) ion

chromium (III) ion

B

acetaldehyde
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
ethylidene diacetate
542-10-9

ethylidene diacetate

acetaldehyde
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

NiMe2(PEt3)2

A

(CO)2Ni(P(C2H5)3)2
16787-33-0

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

B

acetaldehyde
75-07-0

acetaldehyde

C

dimethylglyoxal
431-03-8

dimethylglyoxal

D

acetone
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%
N-fluoro-N-(1-(m-tolyl)ethyl)benzenesulfonamide

N-fluoro-N-(1-(m-tolyl)ethyl)benzenesulfonamide

A

N-m-tolyl-benzenesulfonamide
13587-57-0

N-m-tolyl-benzenesulfonamide

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃;A 98%
B n/a
isobutyl vinyl ether
109-53-5

isobutyl vinyl ether

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With sulfuric acid; water In neat (no solvent) at 80 - 100℃; for 3.5h; Temperature;97%
Hydrolysis;
2-methyl-23-crown-8
88099-81-4

2-methyl-23-crown-8

A

heptaethylene glycol
5617-32-3

heptaethylene glycol

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With water; hydrogenchloride In 1,4-dioxane Rate constant; Equilibrium constant; Ambient temperature; effect of alkali and alkaline earth metal chlorides and concentrations of alkali-metal chlorides and HCl;A n/a
B 97%
vinyl acetate
108-05-4

vinyl acetate

1-Phenylethanol
98-85-1, 13323-81-4

1-Phenylethanol

A

1-phenylethyl acetate
93-92-5, 50373-55-2

1-phenylethyl acetate

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
[(nBuSn)12(μ3-O)14(μ2-OH)6](2+)*2(2,5-Me2C6H3SO3(1-)) at 75℃; for 5.5h;A 97%
B n/a
In isopropyl ether at 23℃; Enzymatic reaction;
4-chloro-N-fluoro-N-(1-phenylethyl)benzenesulfonamide

4-chloro-N-fluoro-N-(1-phenylethyl)benzenesulfonamide

A

4-chloro-N-phenyl-benzenesulfonamide
7454-47-9

4-chloro-N-phenyl-benzenesulfonamide

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃;A 97%
B n/a
vinyl acetate
108-05-4

vinyl acetate

2-benzyl-1,3-propanediol
2612-30-8

2-benzyl-1,3-propanediol

A

(R)-3-acetoxy-2-benzyl-1-propanol
110270-49-0

(R)-3-acetoxy-2-benzyl-1-propanol

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
Lipase P at 25℃; for 1.5h;A 96%
B n/a
2-methyl-26-crown-9
88099-82-5

2-methyl-26-crown-9

A

octaethylene glycol
5117-19-1

octaethylene glycol

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With water; hydrogenchloride In 1,4-dioxane Rate constant; Equilibrium constant; Ambient temperature; effect of alkali-metal chlorides;A n/a
B 96%
N-fluoro-N-(1-phenylethyl)benzenesulfonamide

N-fluoro-N-(1-phenylethyl)benzenesulfonamide

A

N-phenylbenzenesulfonamide
1678-25-7

N-phenylbenzenesulfonamide

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃; Reagent/catalyst;A 96%
B n/a
N-(1-(3,4-dimethylphenyl)ethyl)-N-fluorobenzenesulfonamide

N-(1-(3,4-dimethylphenyl)ethyl)-N-fluorobenzenesulfonamide

A

N-(3,4-dimethylphenyl)benzenesulfonamide

N-(3,4-dimethylphenyl)benzenesulfonamide

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃;A 96%
B n/a
N-fluoro-N-(1-(naphthalen-2-yl)ethyl)benzenesulfonamide

N-fluoro-N-(1-(naphthalen-2-yl)ethyl)benzenesulfonamide

A

N-(naphthalen-2-yl)benzenesulfonamide
7504-85-0

N-(naphthalen-2-yl)benzenesulfonamide

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃;A 96%
B n/a
percarbonate de O,O-α-cumyle et O-vinyle
83206-73-9

percarbonate de O,O-α-cumyle et O-vinyle

A

carbon dioxide
124-38-9

carbon dioxide

B

1-methyl-1-phenylethyl alcohol
617-94-7

1-methyl-1-phenylethyl alcohol

C

2-phenoxypropene
698-91-9

2-phenoxypropene

D

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
In various solvent(s) Product distribution; other solvent;A n/a
B n/a
C 95%
D n/a
N-fluoro-4-nitro-N-(1-phenylethyl)benzenesulfonamide

N-fluoro-4-nitro-N-(1-phenylethyl)benzenesulfonamide

A

N-nosylaniline
1576-44-9

N-nosylaniline

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃;A 95%
B n/a
(4aS,10aR)-2,4a,9-Trimethyl-4a,10a-dihydro-1,3,4-trioxa-phenanthrene
87051-08-9

(4aS,10aR)-2,4a,9-Trimethyl-4a,10a-dihydro-1,3,4-trioxa-phenanthrene

(1S,2R)-1,4-Dimethyl-1,2-dihydro-naphthalene-1,2-diol
114390-56-6

(1S,2R)-1,4-Dimethyl-1,2-dihydro-naphthalene-1,2-diol

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With acetic acid; zinc In diethyl ether at -5℃; for 1.5h;A 94%
B n/a
trans-2-Butene
624-64-6

trans-2-Butene

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With oxygen; ozone In gas Product distribution; gas-phase ozonolysis of alkenes; formation of OH radicals; use of CO as scavenger for OH radicals;94%
With ozone at 24.85℃; under 760 Torr; for 0.166667h; Oxidation;
chloroethane
75-00-3

chloroethane

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With oxygen; kieselguhr; copper(l) chloride In dichloromethane for 1.5h; Oxidation; Heating;94%
2-methyl-3-oxo-1,4-dioxaspiro<4.5>decane
27131-71-1

2-methyl-3-oxo-1,4-dioxaspiro<4.5>decane

A

cyclohexanone
108-94-1

cyclohexanone

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
at 800℃; Product distribution; other temperatures;A 93%
B n/a
β-isopropoxyethyl vinyl sulfoxide
80857-63-2

β-isopropoxyethyl vinyl sulfoxide

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
at 280 - 290℃; for 1.5h; Product distribution;93%
3-(anthracene-9-yl)acrylaldehyde
38982-12-6

3-(anthracene-9-yl)acrylaldehyde

A

acetaldehyde
75-07-0

acetaldehyde

B

9-anthracene aldehyde
642-31-9

9-anthracene aldehyde

Conditions
ConditionsYield
With tetra(n-butyl)ammonium hydroxide; water at 150℃; for 0.166667h; Reagent/catalyst; Microwave irradiation; Green chemistry;A n/a
B 93%
N-fluoro-N-(1-(p-tolyl)ethyl)benzenesulfonamide

N-fluoro-N-(1-(p-tolyl)ethyl)benzenesulfonamide

A

N-p-tolyl-benzenesulfonamide
6311-65-5

N-p-tolyl-benzenesulfonamide

B

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With formic acid at 50℃;A 93%
B n/a
ethyl bromide
74-96-4

ethyl bromide

acetaldehyde
75-07-0

acetaldehyde

Conditions
ConditionsYield
With C30H38Cl2Ir2N4 In dimethyl sulfoxide at 30℃; for 4.5h;93%
2-methylfuran
534-22-5

2-methylfuran

acetaldehyde
75-07-0

acetaldehyde

1,1-bis<2-(5-methyl)-furyl>-ethane
3209-79-8

1,1-bis<2-(5-methyl)-furyl>-ethane

Conditions
ConditionsYield
With ion-exchange resin Lewatit SPC 108 (acid form) In 1,4-dioxane; water at 20℃; for 1h;100%
With N-(trifluoromethanesulfonyl)phosphoramidic acid diphenyl ester In toluene at 20 - 95℃; for 5h;81%
With o-benzenedisulfonimide In toluene at 90℃; for 5h;80%
With hydrogenchloride
With improved graphene oxide In neat (no solvent) at 60℃; for 6h;
1.3-propanedithiol
109-80-8

1.3-propanedithiol

acetaldehyde
75-07-0

acetaldehyde

2-methyl-1,3-dithian
6007-26-7

2-methyl-1,3-dithian

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In dichloromethane at 0℃; for 1h;100%
acid74%
With toluene-4-sulfonic acid In benzene for 6h; Heating;70%
N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide
14316-14-4

N-(2-hydroxy-ethyl)-4-methyl-benzenesulfonamide

acetaldehyde
75-07-0

acetaldehyde

2-methyl-3-tosyloxazolidine

2-methyl-3-tosyloxazolidine

Conditions
ConditionsYield
With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve;100%
With hydrogenchloride; benzene
acetaldehyde
75-07-0

acetaldehyde

2-oxo-propionic acid
127-17-3

2-oxo-propionic acid

3-hydroxy-2-butanon
513-86-0, 52217-02-4

3-hydroxy-2-butanon

Conditions
ConditionsYield
With sodium hydroxide; thiamine diphosphate chloride hydrochloride In methanol at 37℃; for 5.5h;100%
Vergaerung durch Essigbakterien;
durch Hefe; Ausbeute ist groesser,wenn zu der gaerenden Brenztraubensaeure-Loesung gleich nach Beginn der Gaerung noch Acetalehyd zugesetzt wird;
acetaldehyde
75-07-0

acetaldehyde

ethanol
64-17-5

ethanol

Conditions
ConditionsYield
With perchloric acid; 9,10-dihydro-10-methylacridine In acetonitrile at 59.9℃; for 1h; Product distribution; other aldehydes and ketones; primary kinetic isotope effects (kH/kD);100%
With tris(triphenylphosphine)ruthenium(II) chloride; formic acid; tributyl-amine In various solvent(s) for 0.5h; Ambient temperature;89%
With ammonium chloride; zinc In tetrahydrofuran; water at 20℃; for 0.333333h;84%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

acetaldehyde
75-07-0

acetaldehyde

2-<(trimethylsilyl)oxy>propanenitrile
41309-99-3

2-<(trimethylsilyl)oxy>propanenitrile

Conditions
ConditionsYield
With Zr(IV) metal-organic framework with 1,4-benzenedicarboxylate in anhydrous form In dichloromethane at 40℃; for 46h; Inert atmosphere; Reflux;100%
With Eu2(benzene-1,2,3,4,5,6-hexacarboxylate)(H2O)3 In acetonitrile at 20 - 100℃; for 3h;99%
With {[Zn3(1,2-bis(4-pyridyl)ethene)4(μ-OOCC2H5)4](1,2-bis(4-pyridyl)ethene)(ClO4)2}n In dichloromethane Catalytic behavior; Reagent/catalyst; Solvent;82%
acetaldehyde
75-07-0

acetaldehyde

phenylacetylene
536-74-3

phenylacetylene

Conditions
ConditionsYield
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h;100%
Stage #1: phenylacetylene With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Inert atmosphere; Schlenk technique;
Stage #2: acetaldehyde In diethyl ether; hexane at -78 - 20℃; for 1h; Inert atmosphere; Schlenk technique;
98%
Stage #1: phenylacetylene With n-butyllithium In tetrahydrofuran; hexane for 0.5h; Cooling with ice;
Stage #2: acetaldehyde In tetrahydrofuran; hexane
87%
2-Methylthiophene
554-14-3

2-Methylthiophene

acetaldehyde
75-07-0

acetaldehyde

2-methyl-5-(1-(5-methylthiophen-2-yl)ethyl)thiophene
19077-07-7

2-methyl-5-(1-(5-methylthiophen-2-yl)ethyl)thiophene

Conditions
ConditionsYield
With ion-exchange resin Lewatit SPC 108 (acid form) In 1,4-dioxane; water at 20℃; for 1.5h;100%
4-amino-1,2,4-triazole
584-13-4

4-amino-1,2,4-triazole

acetaldehyde
75-07-0

acetaldehyde

4-(Ethylideneamino)-1,2,4-triazole
33761-49-8

4-(Ethylideneamino)-1,2,4-triazole

Conditions
ConditionsYield
With sulfuric acid In ethanol for 4h; Heating;100%
With molecular sieve for 3h; Ambient temperature;39%
3-(tetrahydropyran-2'-yloxy)propyne
6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

acetaldehyde
75-07-0

acetaldehyde

5-<(Tetrahydro-2H-pyran-2-yl)oxy>-3-pentyn-2-ol
14092-30-9

5-<(Tetrahydro-2H-pyran-2-yl)oxy>-3-pentyn-2-ol

Conditions
ConditionsYield
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h;
Stage #2: acetaldehyde In tetrahydrofuran; hexane at -78℃; for 1h; Further stages.;
100%
With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at -78 - 20℃; for 2h;95%
Stage #1: 3-(tetrahydropyran-2'-yloxy)propyne With n-butyllithium In tetrahydrofuran; hexane at -78 - 0℃; Inert atmosphere;
Stage #2: acetaldehyde In tetrahydrofuran; hexane at -78 - 20℃; Inert atmosphere;
89%
trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

2,4-Dichloroaniline
554-00-7

2,4-Dichloroaniline

acetaldehyde
75-07-0

acetaldehyde

2-(2,4-Dichloro-phenylamino)-propionitrile
145100-49-8

2-(2,4-Dichloro-phenylamino)-propionitrile

Conditions
ConditionsYield
With water In dichloromethane for 24h; Ambient temperature;100%
N-Hydroxytryptamine
4761-34-6

N-Hydroxytryptamine

acetaldehyde
75-07-0

acetaldehyde

C12H14N2O

C12H14N2O

Conditions
ConditionsYield
With acetic acid In methanol for 12h;100%
2-Aminobenzyl alcohol
5344-90-1

2-Aminobenzyl alcohol

acetaldehyde
75-07-0

acetaldehyde

2-methyl-1,4-dihydro-2H-benz[d][1,3]oxazine
59689-24-6

2-methyl-1,4-dihydro-2H-benz[d][1,3]oxazine

Conditions
ConditionsYield
With calcium chloride In dichloromethane100%
With magnesium sulfate In tetrahydrofuran at 60℃; for 3h;75%
In benzene
danishefsky's diene
54125-02-9

danishefsky's diene

acetaldehyde
75-07-0

acetaldehyde

2-methyl-2,3-dihydro-4H-pyran-4-one
19185-89-8

2-methyl-2,3-dihydro-4H-pyran-4-one

Conditions
ConditionsYield
With boron trifluoride diethyl etherate In diethyl ether at -70℃; for 1h;100%
With boron trifluoride diethyl etherate In diethyl ether at -78℃; for 2h;89%
With boron trifluoride In diethyl ether at -78℃; for 2h; hetero-Diels-Alder reaction;88%
methylene bis phosphonate de diethyle
63366-56-3

methylene bis phosphonate de diethyle

acetaldehyde
75-07-0

acetaldehyde

2-ethoxy-2-(2',2'-diethoxy-3',5'-dimethyl-1',4',2'-dioxaphospholanyl)methylene-3,5-dimethyl-1,4,2-dioxaphospholane
123146-81-6

2-ethoxy-2-(2',2'-diethoxy-3',5'-dimethyl-1',4',2'-dioxaphospholanyl)methylene-3,5-dimethyl-1,4,2-dioxaphospholane

Conditions
ConditionsYield
In neat (no solvent) 1) 20 deg C, 2h, 2) 0.5 mm Hg, 20 deg C;100%
N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)hydroxylamine
68385-34-2

N-(2-hydroxy-1,1-dimethyl-2-phenylethyl)hydroxylamine

acetaldehyde
75-07-0

acetaldehyde

3-hydroxy-2,2,4-trimethyl-5-phenyloxazolidine

3-hydroxy-2,2,4-trimethyl-5-phenyloxazolidine

Conditions
ConditionsYield
In ethanol100%
O-mesitoylhydroxylamine
37477-17-1

O-mesitoylhydroxylamine

acetaldehyde
75-07-0

acetaldehyde

mesityloylacetaldoxime
84298-25-9

mesityloylacetaldoxime

Conditions
ConditionsYield
With magnesium sulfate In diethyl ether at 0℃; for 82h;100%
2-(2'-Hydroxy-5'-nitrophenyl)ethylamine hydrochloride
129295-70-1

2-(2'-Hydroxy-5'-nitrophenyl)ethylamine hydrochloride

acetaldehyde
75-07-0

acetaldehyde

N,N-Diethyl-2-(2'-hydroxy-5'-nitrophenyl)ethylamine hydrochloride
129295-72-3

N,N-Diethyl-2-(2'-hydroxy-5'-nitrophenyl)ethylamine hydrochloride

Conditions
ConditionsYield
With sodium cyanoborohydride In methanol pH 6-8;100%
Ethyl isocyanoacetate
2999-46-4

Ethyl isocyanoacetate

acetaldehyde
75-07-0

acetaldehyde

5-Methyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester
55942-37-5

5-Methyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester

Conditions
ConditionsYield
triethylamine; copper(l) chloride In tetrahydrofuran for 10h; Ambient temperature;100%
(4aR,7R,8aR)-4,4,7-Trimethyl-hexahydro-1-oxa-3-thia-naphthalene
79618-03-4

(4aR,7R,8aR)-4,4,7-Trimethyl-hexahydro-1-oxa-3-thia-naphthalene

acetaldehyde
75-07-0

acetaldehyde

1-((2R,4aR,7R,8aR)-4,4,7-Trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-ethanol
79563-69-2, 112067-00-2, 112067-01-3

1-((2R,4aR,7R,8aR)-4,4,7-Trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-ethanol

Conditions
ConditionsYield
With n-butyllithium 1.) THF, -78 deg C;100%
1R,2S-N,N-dimethyl-2-phenyl-3-methyl-1,3-diaminoethane
130857-96-4

1R,2S-N,N-dimethyl-2-phenyl-3-methyl-1,3-diaminoethane

acetaldehyde
75-07-0

acetaldehyde

(1S,2S,3R,4S,5R)-1,2,3,4-Tetramethyl-5-phenyl-imidazolidine
130827-40-6

(1S,2S,3R,4S,5R)-1,2,3,4-Tetramethyl-5-phenyl-imidazolidine

Conditions
ConditionsYield
In chloroform for 24h; Ambient temperature;100%
1-mercaptomethyl-2-(α-mercaptoethyl)benzene
136103-76-9

1-mercaptomethyl-2-(α-mercaptoethyl)benzene

acetaldehyde
75-07-0

acetaldehyde

cis-2,4-dimethyl-1,3-dithia-5,6-benzocycloheptene
136103-74-7

cis-2,4-dimethyl-1,3-dithia-5,6-benzocycloheptene

Conditions
ConditionsYield
With hydrogenchloride In 1,4-dioxane for 0.25h;100%
methyl 5-methoxybenzocyclobutene-1-carboxylate
97051-77-9

methyl 5-methoxybenzocyclobutene-1-carboxylate

acetaldehyde
75-07-0

acetaldehyde

methyl 1-(1-hydroxyethyl)-5-methoxybenzocyclobutene-1-carboxylate
126444-40-4, 126444-58-4

methyl 1-(1-hydroxyethyl)-5-methoxybenzocyclobutene-1-carboxylate

Conditions
ConditionsYield
With n-butyllithium; diisopropylamine; lithium diisopropyl amide In tetrahydrofuran; hexane at -78℃; for 0.833333h;100%
potassium cyanide
151-50-8

potassium cyanide

acetaldehyde
75-07-0

acetaldehyde

2-amino-1-phenylpropane
60-15-1, 156-34-3, 51-64-9, 300-62-9

2-amino-1-phenylpropane

2-<(1-methyl-2-phenylethyl)amino>propanenitrile
3535-04-4

2-<(1-methyl-2-phenylethyl)amino>propanenitrile

Conditions
ConditionsYield
With sodium hydrogensulfite In methanol; water Ambient temperature;100%
acetaldehyde
75-07-0

acetaldehyde

N-benzyl hydroxylalmine
622-30-0

N-benzyl hydroxylalmine

5(Z)-N-ethylidene-1-phenylmethanamine N-oxide
243140-08-1

5(Z)-N-ethylidene-1-phenylmethanamine N-oxide

Conditions
ConditionsYield
In dichloromethane at 20℃; for 1h;100%
With sodium sulfate In dichloromethane Ambient temperature;55%
acetaldehyde
75-07-0

acetaldehyde

N-benzyl hydroxylalmine
622-30-0

N-benzyl hydroxylalmine

N-ethylidenebenzylamine N-oxide
20135-15-3, 243140-08-1, 139189-66-5

N-ethylidenebenzylamine N-oxide

Conditions
ConditionsYield
With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
With magnesium sulfate In dichloromethane at 20℃; for 1h; Inert atmosphere;100%
acetaldehyde
75-07-0

acetaldehyde

1-Phenylazo-ethylamine
81549-01-1

1-Phenylazo-ethylamine

3,5-dimethyl-1-phenyl-1H-1,2,4-triazole
41217-48-5

3,5-dimethyl-1-phenyl-1H-1,2,4-triazole

Conditions
ConditionsYield
In chloroform Ambient temperature;100%
acetaldehyde
75-07-0

acetaldehyde

(1S*,2R*)-cis-bicyclo<3.3.0>oct-3,7-diene-2-spiro-4'-<(α,α-bis(phenylsulfenyl))-γ-butyrolactone>
86993-52-4

(1S*,2R*)-cis-bicyclo<3.3.0>oct-3,7-diene-2-spiro-4'-<(α,α-bis(phenylsulfenyl))-γ-butyrolactone>

(1S*,2R*)-cis-bicyclo<3.3.0>oct-3,7-diene-2-spiro-4'-<α-(1-hydroxyethyl)-α-(Phenylsulfenyl)-γ-butyrolactone>
86971-75-7

(1S*,2R*)-cis-bicyclo<3.3.0>oct-3,7-diene-2-spiro-4'-<α-(1-hydroxyethyl)-α-(Phenylsulfenyl)-γ-butyrolactone>

Conditions
ConditionsYield
With ethylmagnesium bromide In tetrahydrofuran; diethyl ether 1.) 0 deg C;100%
With ethylmagnesium bromide100%

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