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402788

Sigma-Aldrich

Acetaldehyde

ACS reagent, ≥99.5%

Synonym(s):

Ethanal

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About This Item

Linear Formula:
CH3CHO
CAS Number:
75-07-0
Molecular Weight:
44.05
Beilstein:
505984
EC Number:
200-836-8
MDL number:
MFCD00006991
UNSPSC Code:
12352100
eCl@ss:
39021102
PubChem Substance ID:
24865119
NACRES:
NA.21

biological source

synthetic

Quality Level

200

grade

ACS reagent

vapor density

1.52 (vs air)

vapor pressure

14.63 psi ( 20 °C)

Assay

≥99.5%

form

liquid

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.)

functional group

aldehyde

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.

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Signal Word

Danger

Hazard Statements

H224,H319,H335,H341,H350

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

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Certificates of Analysis (COA)

Lot/Batch Number
STBK6462
SHBN8701
SHBN6006
STBK2413
SHBN1273

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Acetaldehyde diethyl acetal 99%

Sigma-Aldrich

A902

Acetaldehyde diethyl acetal

Acetaldehyde solution certified reference material, 1000 μg/mL in water, ampule of 100 × 1.2 mL

Supelco

CRM868095

Acetaldehyde solution

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)
Eagleson M.
Concise Encyclopedia Chemistry, 4-4 (1994)
Proline-catalysed Mannich reactions of acetaldehyde.
Yang JW, et al.
Nature, 452(7186), 453-455 (2008)
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)
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)
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