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Merck
CN

T60607

Triethyl orthopropionate

97%

Synonym(s):

1,1,1-Triethoxypropane

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About This Item

Linear Formula:
CH3CH2C(OC2H5)3
CAS Number:
115-80-0
Molecular Weight:
176.25
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24900343
EC Number:
204-108-0
Beilstein/REAXYS Number:
906798
MDL number:
MFCD00009226

Key Documents

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Product Name

Triethyl orthopropionate, 97%

InChI key

FGWYWKIOMUZSQF-UHFFFAOYSA-N

InChI

1S/C9H20O3/c1-5-9(10-6-2,11-7-3)12-8-4/h5-8H2,1-4H3

SMILES string

CCOC(CC)(OCC)OCC

assay

97%

refractive index

n20/D 1.402 (lit.)

bp

155-160 °C (lit.)

density

0.876 g/mL at 25 °C (lit.)

Quality Level

200

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Application

Triethyl orthopropionate is commonly used in the Claisen rearrangement to construct new C-C bonds. It can react with pyrrole and chloroacetic acid to form 1,1,1- [tri-(pyrrol-2-yl)]propane.

pictograms

FlameExclamation mark
GHS02,GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2

Storage Class

3 - Flammable liquids

wgk

WGK 1

flash_point_f

140.0 °F - closed cup

flash_point_c

60 °C - closed cup

ppe

Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
MKCW3498
MKCF3049
MKBT2971V
MKBN8814V
MKBD4119V

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The Johnson-Claisen rearrangement of 3-hydroxy-2-methylenealkanenitriles: Stereoselective synthesis of functionalized trisubstituted alkenes.
Basavaiah D and Pandiaraju S
Tetrahedron Letters, 36(5), 757-758 (1995)
Acyclic stereoselection. 44. Diastereoselectivity in the ortho ester Claisen rearrangement of chiral propargylic alcohols. Use of. beta.-allenic esters as chiral methylmalonaldehyde synthons.
Henderson M A and Heathcock C H
The Journal of Organic Chemistry, 53(20), 4736-4745 (1988)
Stereoselectivity in the ortho ester Claisen rearrangements of the E and Z isomers of. gamma.-(1, 3-dioxan-4-yl) allyl alcohols.
Tadano K, et al.
The Journal of Organic Chemistry, 55(7), 2108-2113 (1990)
Reactions between pyrrole and orthoesters: preparation of tri-(pyrrol-2-yl) alkanes.
Reese C B and Yan H
Tetrahedron Letters, 42(32), 5545-5547 (2001)
Claisen rearrangement of (Z)-3-deoxy-3-C-[(hydroxymethyl) methylene]-1, 2: 5, 6-di-O-isopropylidene-. alpha.-D-ribo-hexofuranose with triethyl orthopropionate.
Tadano K, et al.
The Journal of Organic Chemistry, 54(5), 1223-1227 (1989)

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