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253871

Sigma-Aldrich

1-Nonyne

99%

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About This Item

Linear Formula:
CH3(CH2)6C≡CH
CAS Number:
3452-09-3
Molecular Weight:
124.22
EC Number:
222-375-1
MDL number:
MFCD00009567
UNSPSC Code:
12352100
PubChem Substance ID:
24855336
NACRES:
NA.22

vapor pressure

16 mmHg ( 37.7 °C)

Assay

99%

form

liquid

refractive index

n20/D 1.422 (lit.)

bp

150-151 °C (lit.)

mp

−50 °C (lit.)

density

0.757 g/mL at 25 °C (lit.)

SMILES string

CCCCCCCC#C

InChI

1S/C9H16/c1-3-5-7-9-8-6-4-2/h1H,4-9H2,2H3

InChI key

OSSQSXOTMIGBCF-UHFFFAOYSA-N

General description

1-Nonyne reacts with thianthrene cation radical tetrafluoroborate to form trans-1,2-bis(5-thianthreniumyl)alkene tetrafluoroborate.

Application

1-Nonyne has been used in enantioselective synthesis of cladospolide B, C and (ent)-cladospolide D.

Pictograms

FlameExclamation mark
GHS02,GHS07

Signal Word

Warning

Hazard Statements

H226,H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 3

Flash Point(F)

93.2 °F - closed cup

Flash Point(C)

34 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Yalan Xing et al.
Organic letters, 11(5), 1107-1110 (2009-02-06)
The enantioselective synthesis of cladospolide B, C, and (ent)-cladospolide D has been achieved in 11-15 steps from 1-nonyne. The route relies upon an alkyne zipper reaction to relay an ynone and dienoate functional groups across a nine carbon fragment, which
Paramashivappa Rangappa et al.
The Journal of organic chemistry, 70(24), 9764-9770 (2005-11-19)
[structure: see text] Thianthrene cation radical tetrafluoroborate (Th*+ BF4(-)) added to the terminal alkynes 1-pentyne, 1-hexyne, 1-heptyne, 1-octyne, 1-nonyne, and 1-decyne to form trans-1,2-bis(5-thianthreniumyl)alkene tetrafluoroborates (1-6). Similarly, addition of phenoxathiin cation radical tetrafluoroborate (PO*+ BF4(-)) to the same alkynes gave

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