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468037

cis-1,4-Diacetoxy-2-butene

Name: <I>cis</I>-1,4-Diacetoxy-2-butene
Brand: ALDRICH

95%

Synonym(s):

cis-2-Butene-1,4-diol diacetate

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About This Item

Linear Formula:

CH₃CO₂CH₂CH=CHCH₂O₂CCH₃

CAS Number:

25260-60-0

Molecular Weight:

172.18

MDL number:

MFCD00059339

UNSPSC Code:

12352100

PubChem Substance ID:

24870459

NACRES:

NA.22

Assay

95%

refractive index

n20/D 1.443 (lit.)

bp

120-121 °C/18 mmHg (lit.)

density

1.08 g/mL at 25 °C (lit.)

SMILES string

[H]\C(COC(C)=O)=C(/[H])COC(C)=O

InChI

1S/C8H12O4/c1-7(9)11-5-3-4-6-12-8(2)10/h3-4H,5-6H2,1-2H3/b4-3-

InChI key

VZUAUHWZIKOMFC-ARJAWSKDSA-N

General description

cis-1,4-Diacetoxy-2-butene is an ester. Ruthenium olefin metathesis catalysts having cyclic (alkyl)(amino)carbenes effectively catalyzes the cross-metathesis of cis-1,4-diacetoxy-2-butene with allylbenzene. cis-1,4-Diacetoxy-2-butene on pyrolysis affords 1-acetoxy-1,3-butadiene, a diacetate and an isomeric 1,2-diacetoxy-3-butene. Mechanism of pyrolysis has been investigated.

Application

cis-1,4-Diacetoxy-2-butene may be used in the preparation of hindered Diels-Alder adducts. It may be used for the synthesis of 1,2,3,4-tetrahydro-2-vinylquinoxalines, via Palladium-catalyzed tandem allylation of 1,2-phenylenediamines.

Pictograms

GHS07

Signal Word

Warning

Hazard Statements

H315

Precautionary Statements

P264 - P280 - P302 + P352 - P332 + P313 - P362 + P364

Hazard Classifications

Skin Irrit. 2

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Diels-alder adducts of 3,6-dibromophencyclone with symmetrical 1,4-disubstituted-cis-2-butenes: comparisons with the adduct of phencyclone and N-benzylmaleimide, and one-dimensional and two-dimensional nuclear magnetic resonance studies and ab initio structure calculations.

Kerstin Rosmarion et al.

Applied spectroscopy, 59(3), 366-375 (2005-05-20)

Hindered Diels-Alder adducts have been prepared from 3,6-dibromophencyclone, 2, with cis-1,4-diacetoxy-2-butene, 3; cis-2-butene-1,4-diol, 4; and N-benzylmaleimide, 5. The adduct from the parent phencyclone, 1, with N-benzylmaleimide was prepared for comparison. One- and two-dimensional (1D and 2D) proton and carbon-13 NMR

Pyrolysis of Esters. V. Mechanism of 1, 4-Elimination1.

Bailey WJ and BARCLAY Jr R.

The Journal of Organic Chemistry, 21(3), 328-331 (1956)

Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes.

Donde R Anderson et al.

Organometallics, 27(4), 563-566 (2008-06-28)

The evaluation of ruthenium olefin metathesis catalysts 4-6 bearing cyclic (alkyl)(amino)carbenes (CAACs) in the cross-metathesis of cis-1,4-diacetoxy-2-butene (7) with allylbenzene (8) and the ethenolysis of methyl oleate (11) is reported. Relative to most NHC-substituted complexes, CAAC-substituted catalysts exhibit lower E/Z

Palladium-catalyzed tandem allylation of 1, 2-phenylenediamines with cis-1, 4-diacetoxy-2-butene.

Yang SC, et al.

Tetrahedron Letters, 45(25), 4951-4954 (2004)

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