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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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Sigma-Aldrich

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244341

2-Butyn-1-ol

Homologation method for preparation of substituted pentacenes and naphthacenes.
Takahashi T, et al.
The Journal of Organic Chemistry, 71(21), 7967-7977 (2006)
Małgorzata Kupczewska-Dobecka et al.
Medycyna pracy, 60(5), 347-357 (2009-12-17)
Derived No Effect Level (DNEL(inh)) has been set for occupational exposure to but-2-yno-1,4-diol according to REACH principles. Maximum allowable concentration (MAC) and DNEL(inh) have been compared. Experimental data from two inhalation studies on rats and three oral studies have been
Douglass F Taber et al.
The Journal of organic chemistry, 73(4), 1605-1607 (2008-01-17)
The conversion of 2-butyn-1,4-diol to (Z)-2,4-diiodobut-2-en-1-ol proceeded efficiently using in situ generated trimethylsilyl iodide. Coupling with Grignard reagents and other nucleophiles delivered (2Z)-2-iodo allylic alcohols. The geometry of the products was established by nOe.
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)
J Hellwig et al.
Toxicology letters, 92(3), 221-230 (1997-08-22)
Developmental toxicity of 2-butin-1,4-diol was determined in groups of 18-22 pregnant Wistar rats at dose levels of 10, 40 and 80 mg/kg bw/day administered by gavage from days 6 to 15 pc. At 80 mg/kg bw/day food consumption and maternal
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