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122068

trans-4-Methoxy-3-buten-2-one

technical grade, 90%

Synonym(s):

(E)-4-Methoxy-3-buten-2-one

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10 g
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$108.00
50 g

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250 g
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$1,260.00
$945.00

About This Item

Linear Formula:
CH3OCH=CHCOCH3
CAS Number:
51731-17-0
Molecular Weight:
100.12
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24847477
EC Number:
257-364-0
Beilstein/REAXYS Number:
2070991
MDL number:
MFCD00008778
Assay:
90%

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grade

technical grade

Quality Level

100

assay

90%

refractive index

n20/D 1.468 (lit.)

bp

200 °C (lit.)

density

0.982 g/mL at 25 °C (lit.)

functional group

ether, ketone

storage temp.

2-8°C

SMILES string

[H]\C(OC)=C(\[H])C(C)=O

InChI

1S/C5H8O2/c1-5(6)3-4-7-2/h3-4H,1-2H3/b4-3+

InChI key

VLLHEPHWWIDUSS-ONEGZZNKSA-N

General description

trans-4-Methoxy-3-buten-2-one acts as substrate and undergoes zinc triflate-catalyzed Mukaiyama-Michael reaction with 3-TBSO-substituted vinyldiazoacetate to yield functionalized 3-keto-2-diazoalkanoates[1].

Application

trans-4-Methoxy-3-buten-2-one was used as starting reagent for enantioselective total synthesis of (-)-epibatidine.

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trans-4-Methoxy-3-buten-2-one technical grade, 90%

Sigma-Aldrich

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trans-4-Methoxy-3-buten-2-one

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Sigma-Aldrich

161314

3-Butyn-2-one

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene 95%

Sigma-Aldrich

212830

trans-1-Methoxy-3-trimethylsiloxy-1,3-butadiene

3-Methoxy-2-cyclopenten-1-one 99%

Sigma-Aldrich

393274

3-Methoxy-2-cyclopenten-1-one

assay

90%

assay

95%

assay

95%

assay

99%

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

refractive index

n20/D 1.468 (lit.)

refractive index

n20/D 1.406 (lit.)

refractive index

n20/D 1.454 (lit.)

refractive index

-

density

0.982 g/mL at 25 °C (lit.)

density

0.87 g/mL at 25 °C (lit.)

density

0.885 g/mL at 25 °C (lit.)

density

-

bp

200 °C (lit.)

bp

85 °C (lit.)

bp

68-69 °C/14 mmHg (lit.)

bp

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

145.4 °F - closed cup

flash_point_c

63 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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Certificates of Analysis (COA)

Lot/Batch Number
BCCM5645
STBH2666
STBF1967V
STBB1528V
STBB1528

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Yu Liu et al.
Organic letters, 12(19), 4304-4307 (2010-09-03)
Enedione-diazoesters formed from 3-TBSO-2-diazo-3-butenoates undergo base-catalyzed pericyclization that with dinitrogen extrusion and methyl migration provide a novel and efficient route to 2-carboalkoxyresorcinols. Intercepting the intermediate enolate anion with methyl vinyl ketone leads to the corresponding 4-substituted 2-carboalkoxyresorcinol and suggests generalization
Bifunctional thiourea-catalyzed enantioselective double Michael reaction of ?, d-unsaturated ?-ketoester to nitroalkene: asymmetric synthesis of (-)-epibatidine.
Hoashi Y, et al.
Tetrahedron Letters, 45(50), 9185-9188 (2004)

Global Trade Item Number

SKUGTIN
122068-10G04061838720559
122068-250G04061837374517
122068-50G04061837374524

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