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2-Iodopyridine

2-Iodopyridine structure

CAS No:
5029-67-4
Formula:
C5H4IN
Chemical Name:
2-Iodopyridine
Synonyms:
Pyridine,2-iodo-;2-Iodopyridine;2-Pyridyl iodide;NSC 5075
Categories:
Pharmaceutical Intermediates > Antiparkinson Agents

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Description

Light yellow liquid

2-Iodopyridine Basic Attributes

Molecular Weight：

205

Exact Mass：

205.00

NSC Number：

5075

HScode：

2933399090

Characteristics

PSA：

12.9

XLogP3：

1.4

Appearance：

Pale yellow Solid

Density：

1.9735 g/cm³ @ Temp: 20 °C

Melting Point：

118-120 °C

Boiling Point：

93 °C @ Press: 13 Torr

Flash Point：

84.1±19.8 °C

Refractive Index：

1.630

Water Solubility：

Slightly soluble in water.

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

36/37/38

safety instructions：

26-36

Marks：

Hazard note：

Irritant

Stability/Shelf Life：

Stable at normal temperatures and pressures.

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 41 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH Entry Terms：

2-iodopyridine

2-Iodopyridine Use and Manufacturing

Aromatic Finkelstein Reaction; General ProcedureThe reaction was carried out under argon using standard Schlenktechniques due to the moisture and oxygen sensitivity of the copper(I) iodide. A two-neck pear-shaped flask equipped with a refluxcondenser was charged with the (het)aryl bromide starting material, NaI (2 equiv per bromine to exchange), and CuI (5 molpercent per bromineto exchange). N, N′-Dimethylethylenediamine (L1) or N, N′-dimethyl-1, 2-cyclohexanediamine (L2) (10 molpercent per bromine toexchange) and anhydrous 1, 4-dioxane (0.5 mL per 1 mmol NaI)were added. The resulting suspension was heated to 110 °C for 18h. After cooling to r.t., the mixture was poured into aq 25percent NH3 solution.The blue solution was diluted to a doubled volume with H2Oand was extracted three times with CH2Cl2. In the case of the 2, 2′-bipyridines, the combined organic phases were additionally washedwith aq EDTA solution. Otherwise, the combined organic phaseswere solely washed with brine and dried with MgSO4. The solventwas removed under reduced pressure to give the desired product inpure form. If needed, the crude product can be purified by columnchromatography or recrystallization.General procedure: A Schlenk tube was charged with Cu2O (7.2 mg, 10 molpercent), l-proline (11.5 mg, 20 molpercent), aryl (or heteroaryl) bromide (1 or 3, 0.50 mmol), potassium iodide (KI) (249 mg, 0.75 mmol), and EtOH(1.5 mL) under nitrogen atmosphere. The Schlenk tube was sealedwith a teflon valve, and then the reaction mixture was stirred at110C for a period (the reaction progress was monitored by GCanalysis). After the reaction was completed, GC yield of high volatileproduct was determined using an appropriate internal standard(chlorobenzene or 1-chloro-4-methylbenzene) or the solvent wasremoved under reduced pressure. The residue obtained was puri-fied via silica gel chromatography (eluent: petroleum ether/ethylacetate = 10/1) to afford aryl iodides 2a–2o or heteroaryl iodides4a–4g.EXAMPLE 10

Computed Properties

Molecular Weight:205.00
XLogP3:1.4
Hydrogen Bond Acceptor Count:1
Exact Mass:204.93885
Monoisotopic Mass:204.93885
Topological Polar Surface Area:12.9
Heavy Atom Count:7
Complexity:56
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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