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232548

Sigma-Aldrich

3-Ethoxymethacrolein

96%

Synonym(s):

3-Ethoxy-2-methylpropenal

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About This Item

Linear Formula:
C2H5OCH=C(CH3)CHO
CAS Number:
42588-57-8
Molecular Weight:
114.14
EC Number:
255-899-4
MDL number:
MFCD00006975
UNSPSC Code:
12352100
PubChem Substance ID:
24853909
NACRES:
NA.22

Quality Level

100

Assay

96%

form

liquid

refractive index

n20/D 1.4792 (lit.)

bp

78-81 °C/14 mmHg (lit.)

density

0.96 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

CCOC=C(C)C=O

InChI

1S/C6H10O2/c1-3-8-5-6(2)4-7/h4-5H,3H2,1-2H3

InChI key

KDOAHVPFGIYCEU-UHFFFAOYSA-N

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Application

3-Ethoxymethacrolein was used in the synthesis of:
  • 5,10-dideaza-5,6,7,8-tetrahydrofolic acid (DDATHF)
  • quinolines via modified Friedlander synthesis
  • 3-[2-isopropyl-5-methylcyclohexyloxy-(1R, 2S, 5R)]-2-methyl-2E-propenal

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H302 + H312 + H332

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Flam. Liq. 3

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

95.9 °F - closed cup

Flash Point(C)

35.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of quinolines via ortho-lithiated N-acylanilines. A modified Friedlaender synthesis.
Cho IS, et al.
The Journal of Organic Chemistry, 56(26), 7288-7291 (1991)
Photooxygenation of chiral dienol ethers: asymmetric synthesis of alkoxydioxines.
Dussault PH, et al.
Tetrahedron, 55(38), 11437-11454 (1999)
E C Taylor et al.
Investigational new drugs, 14(3), 281-285 (1996-01-01)
A new and extremely efficient synthesis of DDATHF from 4-vinylbenzoic acid and bromomalondialdehyde as precursors has been developed which proceeds in 48% overall yield.

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