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252360

Sigma-Aldrich

Morpholine

ACS reagent, ≥99.0%

Synonym(s):

Tetrahydro-1,4-oxazine

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About This Item

Empirical Formula (Hill Notation):
C4H9NO
CAS Number:
Molecular Weight:
87.12
Beilstein:
102549
EC Number:
MDL number:
UNSPSC Code:
12352100
eCl@ss:
39162409
PubChem Substance ID:
NACRES:
NA.21

grade

ACS reagent

Quality Level

vapor density

3 (vs air)

vapor pressure

31 mmHg ( 38 °C)
7 mmHg ( 20 °C)

Assay

≥99.0%

form

liquid

autoignition temp.

590 °F

expl. lim.

10.8 %

color

APHA: ≤15

refractive index

n20/D 1.454 (lit.)

bp

126.0-130.0 °C
129 °C (lit.)

mp

−7-−5 °C (lit.)

density

0.996 g/mL at 25 °C (lit.)

SMILES string

C1COCCN1

InChI

1S/C4H9NO/c1-3-6-4-2-5-1/h5H,1-4H2

InChI key

YNAVUWVOSKDBBP-UHFFFAOYSA-N

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Application

Morpholine may be used in the preparation of derivatives such as 4-benzoyloxymorpholine and 1-morpholinopropan-1-one. It may also be used in the preparation of (S)-3,3′-bis-morpholinomethyl-5,5′,6,6′,7,7′,8,8′-octahydro-1,1′-bi-2-naphthol, a bifunctional chiral catalyst for asymmetric synthesis. As a base, morpholine can be used in the preparation of 1,3-disubstituted allenes from terminal alkynes and aldehydes.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Repr. 2 - Skin Corr. 1B

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

87.8 °F - closed cup

Flash Point(C)

31 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Preparation of (S)-3,3'-bis-morpholinomethyl-5,5',6,6',7,7',8,8'-octahydro-1,1'-bi-2-naphthol
MTurlington M and Pu L
Organic Syntheses, 87, 59-59 (2010)
Copper-catalyzed electrophilic amination of diorganozinc reagents: 4-phenylmorpholine
Berman AM and Johnson JS
Organic Syntheses, 83, 31-31 (2006)
Synthesis of acylsilanes from morpholine amides. Synthesis of 1-(dimethyl(phenyl)silyl)propan-1-one
Lettan II RB, et al.
Organic Syntheses, 84, 22-22 (2007)
Factors influencing the rate of formation of nitrosomorpholine from morpholine and nitrite: acceleration by thiocyanate and other anions.
T Y Fan et al.
Journal of agricultural and food chemistry, 21(2), 237-240 (1973-03-01)
First telomerisation of piperylene with morpholine using palladium-carbene catalysts.
Neubert P, et al.
Catalysis Communications, 77, 70-74 (2016)

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