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270822

Sigma-Aldrich

Di-tert-butyl acetylenedicarboxylate

98%

Synonym(s):

2-Butynedioic acid di-tert-butyl ester, Di-tert-butyl 2-butynedioate

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About This Item

Linear Formula:
(CH3)3COCOC≡CCOOC(CH3)3
CAS Number:
66086-33-7
Molecular Weight:
226.27
Beilstein/REAXYS Number:
1957547
EC Number:
266-135-4
MDL number:
MFCD00008808
UNSPSC Code:
12352100
PubChem Substance ID:
24856403
NACRES:
NA.22

Quality Level

200

assay

98%

form

solid

bp

80-82 °C/0.05 mmHg (lit.)

mp

33-37 °C (lit.)

functional group

ester

SMILES string

CC(C)(C)OC(=O)C#CC(=O)OC(C)(C)C

InChI

1S/C12H18O4/c1-11(2,3)15-9(13)7-8-10(14)16-12(4,5)6/h1-6H3

InChI key

FBCRUXRGQFLOMC-UHFFFAOYSA-N

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General description

The cross-cyclotrimerization of di-tert-butyl acetylenedicarboxylate, silylacetylenes and acrylamides was studied with cationic rhodium(I)/(R)-tol-binap complex as catalyst. Glycosyl azides were subjected to 1,3-dipolar cycloaddition with di-tert-butyl acetylenedicarboxylate.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

hcodes

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk_germany

WGK 3

ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCBH4571V
BCBC2276V
BCBC2276
1452172
1364618

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W Bröder et al.
Carbohydrate research, 249(1), 221-241 (1993-10-18)
Glycosyl azides provide reliable anomeric protection stable to conditions for hydrolytic removal of ester groups, for reductive opening or release of acetalic diol protection, for the introduction of ether-type protection, and for glycosylation processes. The utility of this anomeric protection
Jun Hara et al.
Angewandte Chemie (International ed. in English), 53(11), 2956-2959 (2014-02-08)
It has been established that a cationic rhodium(I)/(R)-tol-binap complex catalyzes the cross-cyclotrimerization of silylacetylenes, di-tert-butyl acetylenedicarboxylates, and acrylamides with excellent chemo-, regio-, and enantioselectivities. Unsymmetrical alkynoates can also be employed in place of di-tert-butyl acetylenedicarboxylate for this process, but with

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