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Sigma-Aldrich

6-Heptynoic acid

90%

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About This Item

Linear Formula:
HC≡C(CH2)4COOH
CAS Number:
30964-00-2
Molecular Weight:
126.15
Beilstein:
1747024
MDL number:
MFCD00239430
UNSPSC Code:
12352100
PubChem Substance ID:
24868034
NACRES:
NA.22

Assay

90%

refractive index

n20/D 1.451 (lit.)

bp

93-94 °C/1 mmHg (lit.)

density

0.997 g/mL at 25 °C (lit.)

SMILES string

OC(=O)CCCCC#C

InChI

1S/C7H10O2/c1-2-3-4-5-6-7(8)9/h1H,3-6H2,(H,8,9)

InChI key

OFCPMJGTZUVUSM-UHFFFAOYSA-N

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General description

6-Heptynoic acid is an alkynoic acid with an acetylene bond. It undergoes condensation with various pyrroles to afford optical diverse fluorescent dyes with a terminal alkyne.

Application

6-Heptynoic acid may be used for the following syntheses:
  • alkyne functionalized Boradiazaindacenes (BODIPY)dyes
  • natural products epothilone B and D
  • hymenialdisine (HMD) and aldisine (AD) affinity resins
  • alkynyl esters

Pictograms

Corrosion
GHS05

Signal Word

Danger

Hazard Statements

H314

Hazard Classifications

Skin Corr. 1B

Storage Class Code

8A - Combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

235.4 °F - closed cup

Flash Point(C)

113 °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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Yongqin Wan et al.
Chemistry & biology, 11(2), 247-259 (2004-05-05)
Hymenialdisine (HMD) is a sponge-derived natural product kinase inhibitor with nanomolar activity against CDKs, Mek1, GSK3beta, and CK1 and micromolar activity against Chk1. In order to explore the broader application of the pyrrolo[2,3-c]azepine skeleton of HMD as a general kinase
A novel catalyst with a cuboidal PdMo3S4 core for the cyclization of alkynoic acids to enol lactones.
Wakabayashi T, et al.
Angewandte Chemie (International Edition in English), 35(18), 2123-2124 (1996)
R E Taylor et al.
Organic letters, 3(14), 2221-2224 (2001-07-07)
[reaction: see text] A highly convergent total synthesis of the natural products epothilone B and D is described. The route is highlighted by efficient generation of a C12-C13 trisubstituted olefin which exploits a sequential Nozaki-Hiyama-Kishi coupling and a stereoselective thionyl
Lauren Ray et al.
Nature communications, 7, 13609-13609 (2016-12-22)
Type I modular polyketide synthases assemble diverse bioactive natural products. Such multienzymes typically use malonyl and methylmalonyl-CoA building blocks for polyketide chain assembly. However, in several cases more exotic alkylmalonyl-CoA extender units are also known to be incorporated. In all
Martijn Verdoes et al.
Bioorganic & medicinal chemistry letters, 17(22), 6169-6171 (2007-09-25)
The synthesis of three acetylene functionalized BODIPY dyes is described. These dyes are used to fluorescently modify an azido functionalized epoxomicin analogue employing the Huisgen 1,3-dipolar cycloaddition, resulting in a panel of fluorescent epoxomicin derived proteasome probes.
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