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402788

Sigma-Aldrich

Acetaldehyde

ACS reagent, ≥99.5%

Synonym(s):
Ethanal
Linear Formula:
CH3CHO
CAS Number:
Molecular Weight:
44.05
Beilstein:
505984
EC Number:
MDL number:
eCl@ss:
39021102
PubChem Substance ID:
NACRES:
NA.21

Quality Level

biological source

synthetic

grade

ACS reagent

vapor density

1.52 (vs air)

vapor pressure

14.63 psi ( 20 °C)

assay

≥99.5%

autoignition temp.

365 °F

expl. lim.

60 %

impurities

≤0.008 meq/g Titr. acid

evapn. residue

≤0.005%

refractive index

n20/D 1.332 (lit.)

bp

21 °C (lit.)

mp

−125 °C (lit.)

solubility

alcohols: soluble
water: miscible

density

0.785 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CC=O

InChI

1S/C2H4O/c1-2-3/h2H,1H3

InChI key

IKHGUXGNUITLKF-UHFFFAOYSA-N

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General description

Acetaldehyde is an industrially important solvent used as an intermediate for the synthesis of a wide range of compounds. On oxidation it forms acetic acid and ethanol on reduction. The interaction of Criegee intermediate (CH2OO) with acetaldehyde has been measured. Its effect as a neuroactive agent has been studied. Alkynylation reaction of acetaldehyde by asymmetric catalysis has been reported.

Application

Acetaldehyde may be used in the synthesis of 1,3-diamines by one-pot cross double-Mannich reaction and β-amino aldehydes by proline-catalyzed Mannich reaction.

Packaging

5 mL in ampule
100 mL in aluminum bottle
1 L in aluminum bottle

Signal Word

Danger

Hazard Classifications

Carc. 1B - Eye Irrit. 2 - Flam. Liq. 1 - Muta. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

-38.0 °F - closed cup

Flash Point(C)

-38.89 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

Proline-catalysed Mannich reactions of acetaldehyde.
Yang JW, et al.
Nature, 452(7186), 453-455 (2008)
Direct measurement of Criegee intermediate (CH2OO) reactions with acetone, acetaldehyde, and hexafluoroacetone.
Taatjes CA, et al.
Physical Chemistry Chemical Physics, 14(30), 10391-10400 (2012)
Eagleson M.
Concise Encyclopedia Chemistry, 4-4 (1994)
One-pot cross double-Mannich reaction of acetaldehyde catalyzed by a binaphthyl-based amino sulfonamide.
Kano T, et al.
Chemical Communications (Cambridge, England), 49(11), 1118-1120 (2013)
Asymmetric Catalytic Alkynylation of Acetaldehyde: Application to the Synthesis of (+)-Tetrahydropyrenophorol.
Trost BM and Quintard A.
Angewandte Chemie (International Edition in English), 51(27), 6704-6708 (2012)

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