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Sigma-Aldrich

4-Formylmorpholine

99%

Synonym(s):

4-Morpholinecarboxaldehyde

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About This Item

Empirical Formula (Hill Notation):
C5H9NO2
CAS Number:
4394-85-8
Molecular Weight:
115.13
Beilstein:
110293
EC Number:
224-518-3
MDL number:
MFCD00006170
UNSPSC Code:
12352100
PubChem Substance ID:
24855051
NACRES:
NA.22

Quality Level

200

Assay

99%

form

solid

refractive index

n20/D 1.485 (lit.)

bp

236-237 °C (lit.)

mp

20-23 °C (lit.)

density

1.145 g/mL at 25 °C (lit.)

SMILES string

[H]C(=O)N1CCOCC1

InChI

1S/C5H9NO2/c7-5-6-1-3-8-4-2-6/h5H,1-4H2

InChI key

LCEDQNDDFOCWGG-UHFFFAOYSA-N

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General description

Treatment of 4-formylmorpholine with sulphur tetrafluoride in the presence of potassium fluoride gives 4-(trifluoromethyl)morpholine in excellent yields. 4-Formylmorpholine reacts with series of 2-alkyl-2-cyclohexen-1-ones in the presence of POCl3 to give the corresponding 3-alkyl-2-chloro-5,6-dihydrobenzaldehydes and allylic alcohols (by-product).

Application

4-Formylmorpholine has been used in the preparation of:
  • adenine hydrochloride labelled with 14C
  • terphenyl dialdehyde

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

WGK

WGK 1

Flash Point(F)

DIN 51758

Flash Point(C)

DIN 51758

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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Cyclic host having double bonds as bridging units.
Paek K-S and Cram DJ.
Bull. Korean Chem. Soc., 10(6), 569-569 (1989)
Studies in vilsmeier chemistry, V. Vilsmeier reactions of 2-alkyl-2-cyclohexen-1-ones: A novel route to dihydrobenzaldehydes, the formation of allyl alcohols as by-products, and the X-ray crystallographic structure of 3-chloro-2-methyl-2-cyclohexen-1-ol.
Katritzky AR, et al.
Chemische Berichte, 121(5), 999-1003 (1988)
209. A synthesis of adenine labelled with 14C.
Clark VM and Kalckar HM.
Journal of the Chemical Society, 1029-1030 (1950)
Reaction of tertiary formamides with sulphur tetrafluoride. Direct synthesis of (trifluoromethyl) amines.
Dmowski W and Kaminski M.
Journal of Fluorine Chemistry, 23(3), 207-218 (1983)

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