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270822

Di-tert-butyl acetylenedicarboxylate

Name: Di-<I>tert</I>-butyl acetylenedicarboxylate
Brand: ALDRICH

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

UNSPSC Code:

12352100

NACRES:

NA.22

PubChem Substance ID:

24856403

EC Number:

266-135-4

Beilstein/REAXYS Number:

1957547

MDL number:

MFCD00008808

Assay:

98%

Form:

solid

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Properties

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

Description

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

GHS05,GHS07

signalword

Danger

hcodes

H314,H335

pcodes

P260 - P271 - P280 - P303 + P361 + P353 - P304 + P340 + P310 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

8A - Combustible corrosive hazardous materials

wgk

WGK 3

ppe

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

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A new method of anomeric protection and activation based on the conversion of glycosyl azides into glycosyl fluorides.

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

Highly chemo-, regio-, and enantioselective rhodium-catalyzed cross-cyclotrimerization of two different alkynes with alkenes.

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

Global Trade Item Number

SKU	GTIN
270822-5G	04061832618821
270822-1G	04061825922263