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2-Ethynylpyridine

2-Ethynylpyridine structure

CAS No:
1945-84-2
Formula:
C7H5N
Chemical Name:
2-Ethynylpyridine
Synonyms:
Pyridine,2-ethynyl-;2-Ethynylpyridine;2-Pyridylacetylene;Pyridin-2-ylacetylene;2-Pyridylethyne;2-Pyridinylethyne
Categories:
Pharmaceutical Intermediates > Antineoplastics

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Description

clear dark brown liquid

2-Ethynylpyridine Basic Attributes

Molecular Weight：

103.12

Exact Mass：

103.12

BRN：

1098904

DSSTox ID：

DTXSID40173085

HScode：

29339900

Characteristics

PSA：

12.9

XLogP3：

Appearance：

Clear dark brown Liquid

Density：

1.021 g/mL at 25 °C(lit.)

Melting Point：

76-78 °C

Boiling Point：

86-88 °C @ Press: 14 Torr

Flash Point：

170 °F

Refractive Index：

n20/D 1.56(lit.)

Water Solubility：

Soluble in water.

Storage Conditions：

2-8°C

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36-37/39

Marks：

Precautionary statement(s)：

P261-P305 + P351 + P338

Hazard Statements：

H315-H319-H335

GHS Classification：

|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 45 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

ethynylpyridine

2-Ethynylpyridine Use and Manufacturing

Methods of Manufacturing

2-((Trimethylsilyl)ethynyl)pyridine (175mg, 1.0 mmol) was dissolved in MeOH/Dichloromethane (2mL/lmL). The solution was cooled to 0 °C and KOH (112mg, 2.0 mmol) was added. The reaction mixture stirred for 0.5 h, and then quenched with Ha)2-Ethynyl-pyridineA solution of 2-trimethylsilanylethynyl-pyridine (3.05 g, 14 mmol) in MeOH (8.5 mL) was added dropwise to potassium hydroxide solution (1 N, 14 mL) and the reaction mixture was stirred at room temperature for 1 h and then acidified with HC1 (3 N, 8.5 mL) and the mixture concentrated. The residue was then diluted with water and make alkaline with solid sodium carbonate, extracted with diethyl ether and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (1.3 g, 75percent) as a brown liquid. MS: m/e = 176.0[M+H]Example 104-Methyl-2-[(E)-2-(3-methyl-5-pyridin-2-yl-3H-[1, 2, 3]triazol-4-yl)-vinyl]-thiazole-5-carboxylic acid isopropylamide a) 2-Ethynyl-pyridine; To a mixture of 2-pyridinecarbaldehyde (0.96 mL, 10 mmol) in MeOH (43 mL) was added potassium carbonate (2.76 g, 20 mmol) followed by a solution of (1-diazo-2-oxo-propyl)-phosphonic acid dimethyl ester (2.14 g, 11 mmol) in MeOH (14 mL) at room temperature and the resulting mixture stirred for 1.5 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (728 mg, 71percent) as a yellow liquid. MS: m/e=103.0 [M]To a mixture of 2-pyridinecarbaldehyde (0.96 mL, 10 mmol) in MeOH (43 mL) was added potassium carbonate (2.76 g, 20 mmol) followed by a solution of (l-diazo-2-oxo-propyl)- phosphonic acid dimethyl ester (2.14 g, 11 mmol) in MeOH (14 mL) at room temperature and the resulting mixture stirred for 1.5 h. The mixture was then poured into sodium carbonate solution (1 M) and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, diethylether) afforded the title compound (728 mg, 71percent) as a yellow liquid. MS: m/e = 103.0 [M]

Uses

2-ethynylpyridine can be used to synthesize self-doped ion-conjugated polymer poly(2-ethynylpyridinium N-benzoylsulfonate).

Computed Properties

Molecular Weight:103.12
XLogP3:1
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:103.042199164
Monoisotopic Mass:103.042199164
Topological Polar Surface Area:12.9
Heavy Atom Count:8
Complexity:109
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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