B103209

Sigma-Aldrich

2-Butyne-1,4-diol

99%

Linear Formula:
HOCH2C≡CCH2OH
CAS Number:
Molecular Weight:
86.09
Beilstein/REAXYS Number:
1071237
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor pressure

<0.1 mmHg ( 55 °C)

assay

99%

bp

238 °C (lit.)

mp

53-58 °C (lit.)

SMILES string

OCC#CCO

InChI

1S/C4H6O2/c5-3-1-2-4-6/h5-6H,3-4H2

InChI key

DLDJFQGPPSQZKI-UHFFFAOYSA-N

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Application

2-Butyne-1,4-diol is extensively used in the cycloaddition reactions such as the homologation method for the preparation of substituted acenes, rhodium and iridium-catalyzed [2+ 2+ 2] inter and intramolecular cyclotrimerization. It can also be used in the total synthesis of (−)-isolaurallene, (−)-amphidinolide P and bistramide A.

Packaging

1 kg in poly bottle
100, 500 g in poly bottle

Signal Word

Danger

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

UN 2716 6.1 / PGIII

WGK Germany

WGK 3

Flash Point(F)

305.6 °F - closed cup

Flash Point(C)

152 °C - closed cup

Certificate of Analysis

Certificate of Origin

Asymmetric total synthesis of (?)-isolaurallene.
Crimmins M T and Emmitte K A
Journal of the American Chemical Society, 123(7), 1533-1534 (2001)
Total synthesis of (?)-amphidinolide P.
Williams D R, et al.
Organic Letters, 2(7), 945-948 (2000)
A highly efficient and flexible synthesis of substituted carbazoles by rhodium?catalyzed inter?and intramolecular alkyne cyclotrimerizations.
Witulski B and Alayrac C
Angewandte Chemie (International Edition in English), 114(17), 3415-3418 (2002)
Synthesis of silafluorenes by iridium-catalyzed [2+ 2+ 2] cycloaddition of silicon-bridged diynes with alkynes.
Matsuda T, et al.
Organic Letters, 9(1), 133-136 (2007)
Contact dermatitis to Butin-2-diol 1,4.
O Baadsgaard et al.
Contact dermatitis, 13(1), 34-34 (1985-07-01)

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