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B103209

Sigma-Aldrich

2-Butyne-1,4-diol

99%

Synonym(s):

1,4-Butynediol, 1,4-Dihydroxy-2-butyne, 2-Butynediol, Bis(hydroxymethyl)acetylene

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About This Item

Linear Formula:
HOCH2C≡CCH2OH
CAS Number:
110-65-6
Molecular Weight:
86.09
Beilstein:
1071237
EC Number:
203-788-6
MDL number:
MFCD00002915
UNSPSC Code:
12352100
PubChem Substance ID:
24891548
NACRES:
NA.22

vapor pressure

<0.1 mmHg ( 55 °C)

Quality Level

200

Assay

99%

form

crystals

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.

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral - Eye Dam. 1 - Skin Corr. 1B - Skin Sens. 1 - STOT RE 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 2

Flash Point(F)

305.6 °F - closed cup

Flash Point(C)

152 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
Asymmetric total synthesis of (?)-isolaurallene.
Crimmins M T and Emmitte K A
Journal of the American Chemical Society, 123(7), 1533-1534 (2001)
R A Jedrychowski et al.
Journal of applied toxicology : JAT, 12(2), 117-122 (1992-04-01)
2-Butyne-1,4-diol was given to male and female Wistar Imp:DAK rats by oral gavage for 28 consecutive days in daily doses of 1, 10 or 50 mg kg-1 day-1. After 28 days all animals were necropsied. Blood samples were obtained and
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