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Merck
CN

B103209

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
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
24891548
EC Number:
203-788-6
Beilstein/REAXYS Number:
1071237
MDL number:
MFCD00002915
Assay:
99%
Form:
crystals

Key Documents

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InChI

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

InChI key

DLDJFQGPPSQZKI-UHFFFAOYSA-N

SMILES string

OCC#CCO

vapor pressure

<0.1 mmHg ( 55 °C)

assay

99%

form

crystals

bp

238 °C (lit.)

Quality Level

200

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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.

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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

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

ppe

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

Regulatory Information

危险化学品
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Certificates of Analysis (COA)

Lot/Batch Number
SDBB7387
SDBB6881
SDBB6052
STBL3568
STBL2790

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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)
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)
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
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