4-Iodopyridine supplier | CasNO.15854-87-2

Name
4-Iodopyridine
EINECS -0
CAS No. 15854-87-2
Article Data18
CAS DataBase
Density 1.957 g/cm³
Solubility
Melting Point 80 °C
Formula C₅H₄IN
Boiling Point 215.4 °C at 760 mmHg
Molecular Weight 204.998
Flash Point 84.1 °C
Transport Information
Appearance White to off-white crystals
Safety 26-36
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 4-Iodo Pyridine;4-Lodopyridine;
PSA 12.89000
LogP 1.68620

Synthetic route

: 626-61-9
4-Chloropyridine

: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
With acetyl chloride; sodium iodide In acetonitrile at 18 - 80℃; Microwave irradiation;	91%
With hydrogen iodide at 145℃; im Rohr;
With trimethylstannylsodium; iodine 1.) DME, 3 h, cooling 2.) CHCl3, 15 min, room temp.; Yield given. Multistep reaction;

: 504-24-5
4-aminopyridine

: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
Stage #1: 4-aminopyridine With tetrafluoroboric acid; sodium nitrite at -10℃; for 0.5h; Stage #2: With potassium iodide In acetone	70%
With N-iodo-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 4h;	70%
Stage #1: 4-aminopyridine With sodium nitrate; tetrafluoroboric acid In water at -10℃; for 0.5h; Stage #2: With potassium iodide In water; acetone	70%

: 1120-87-2
4-bromopyridin

: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
Stage #1: 4-bromopyridin With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 1.5h; Substitution; Stage #2: With iodine In tetrahydrofuran at 20℃; for 18h; Substitution;	51%

: 110-86-1
pyridine

: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
Stage #1: pyridine With (THF)Li(TMP)Zn(tBu)2 In tetrahydrofuran at 0℃; for 2h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; regioselective reaction;	50%
With n-butyllithium; potassium tert-butylate; iodine; lithium bromide THF / HMPT / hexane 1) -100 deg C; Yield given. Multistep reaction;

: 626-61-9
4-Chloropyridine

: 10034-85-2
hydrogen iodide

: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
at 145℃; im Rohr;

: 7379-35-3
4-chlorpyridine hydrochloride

: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
With sodium iodide In acetonitrile at 80℃; for 24h;	1.5 g
With sodium iodide In acetonitrile at 80℃; for 24h;

: 19524-06-2
4-bromopyridine hydrochloride

A: 5029-67-4
2-iodopyridine

B: 15854-87-2
4-iodopyridine

: 110-86-1
pyridine

A: 1120-90-7
3-iodopyridine

B: 15854-87-2
4-iodopyridine

Conditions

Conditions	Yield
Stage #1: pyridine With Na4(TMP)4Zn4(tBu)4{(C5H3)2Fe} In chloroform-d1 Stage #2: With iodine In chloroform-d1

: 944882-44-4, 406683-20-3
N-[(tert-butoxy)carbonylamino][7-chloro-4-oxo-2-(pyrrolidinylcarbonyl)(3-hydroxyquinolyl)]-N-prop-2-ynylcarboxamide

: 15854-87-2
4-iodopyridine

: 944882-45-5, 406683-21-4
N-[(tert-butoxy)carbonylamino][7-chloro-4-oxo-2-(pyrrolidinylcarbonyl)(3-hydroxyquinolyl)]-N-(3-(4-pyridyl)prop-2-ynyl)carboxamide

Conditions

Conditions	Yield
With 2,6-di-tert-butyl-4-methyl-phenol; triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In dichloromethane at 20℃; Sonogashira reaction;	100%

: 15854-87-2
4-iodopyridine

: zinc(II)-5-(4-ethynylphenyl)-15-(2,4,6-trimethylphenyl)porphyrin

: C42H30IN5Zn

Conditions

Conditions	Yield
In dichloromethane-d2	100%
In dichloromethane-d2	100%
In dichloromethane-d2	100 %Spectr.

: 15854-87-2
4-iodopyridine

: zinc(II)-5-(4-ethynylphenyl)-15-(2,4,6-trimethylphenyl)porphyrin

: [(zinc(II)-5-(4-ethynylphenyl)-15-(2,4,6-trimethylphenyl)porphyrin)(4-iodopyridine)]

Conditions

Conditions	Yield
In dichloromethane-d2; [D3]acetonitrile	100%

: zinc(II)-bis(5,15-(2,4,6-trimethylphenyl))porphyrin

: 15854-87-2
4-iodopyridine

: C43H36IN5Zn

Conditions

Conditions	Yield
In chloroform-d1	100%

: 15854-87-2
4-iodopyridine

: 54010-75-2
zinc trifluoromethanesulfonate

: 192226-54-3
2,9-dimesityl-[1,10]-phenanthroline

: C30H28N2*Zn(2+)*C5H4IN*2CF3O3S(1-)

Conditions

Conditions	Yield
In dichloromethane-d2; [D3]acetonitrile	100%

...Expand

: 15854-87-2
4-iodopyridine

: 54010-75-2
zinc trifluoromethanesulfonate

: 240797-81-3
10-phenyl-1,4-dioxa-7,13-dithia-10-aza-cyclopentadecane

: [Zn(10-phenyl-1,4-dioxa-7,13-dithia-10-azacyclopentadecane)(4‐iodopyridine)](OTf)2

Conditions

Conditions	Yield
In dichloromethane; acetonitrile	100%

...Expand

: 64443-05-6
tetrakis(actonitrile)copper(I) hexafluorophosphate

: 15854-87-2
4-iodopyridine

: 192226-54-3
2,9-dimesityl-[1,10]-phenanthroline

: C35H32CuIN3(1+)

Conditions

Conditions	Yield
In dichloromethane-d2	100%

...Expand

: 15854-87-2
4-iodopyridine

: C38H32N4Zr

: C38H32N4Zr*C5H4IN

Conditions

Conditions	Yield
In dichloromethane-d2	100%

: 15854-87-2
4-iodopyridine

: 1066-54-2
trimethylsilylacetylene

: 133810-35-2
4-(2-(trimethylsilyl)ethynyl)pyridine

Conditions

Conditions	Yield
Sonogashira coupling;	99%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	92%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In tetrahydrofuran at 50℃; Sonogashira Cross-Coupling; Inert atmosphere;	89%

: 15854-87-2
4-iodopyridine

: 930-69-8
sodium thiophenolate

: 33399-48-3
4-(phenylthio)pyridine

Conditions

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 110℃; for 0.05h; microwave irradiation;	99%

: 15854-87-2
4-iodopyridine

: 100-46-9
benzylamine

: 13556-71-3
N-benzyl-4-aminopyridine

Conditions

Conditions	Yield
With cesium acetate; copper In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	99%

: 15854-87-2
4-iodopyridine

: 108-27-0
5-methylpyrrolidin-2-one

: 5-methyl-1-(pyridin-4-yl)pyrrolidin-2-one

Conditions

Conditions	Yield
With copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; potassium carbonate In 1,4-dioxane at 150℃; Sealed tube; Inert atmosphere;	99%

: 15854-87-2
4-iodopyridine

: 5720-07-0
4-methoxyphenylboronic acid

: 939-23-1
p-phenylpyridine

Conditions

Conditions	Yield
With potassium carbonate In 1,2-dimethoxyethane at 100℃; for 24h; Suzuki Coupling;	99%

: 15854-87-2
4-iodopyridine

: 141-32-2
acrylic acid n-butyl ester

: (E)-3-Pyridin-4-yl-acrylic acid butyl ester

Conditions

Conditions	Yield
With tetrabutylammonium acetate; polyurea-encapsulated Pd(OAc)2 In isopropyl alcohol at 90℃; Heck reaction;	98%

: 864949-08-6
2-methyl-3,8-nonadiyn-2-ol

: 15854-87-2
4-iodopyridine

: 2-methyl-9-(pyridin-4-yl)nona-3,8-diyn-2-ol

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 20℃; for 16h; Sonogashira Cross-Coupling;	98%

: 937207-38-0
(5'-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[2,2':3',2''-terthiophene]-5,5''-diyl)bis(trimethylsilane)

: 15854-87-2
4-iodopyridine

: 1185651-82-4
4-[5,5''-bis(trimethylsilyl)-[2,2';3',2'']terthien-5'-yl]-pyridine

Conditions

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; potassium phosphate; tri tert-butylphosphoniumtetrafluoroborate In tetrahydrofuran; water at 20℃; Suzuki cross-coupling; Inert atmosphere;	97%

: 15854-87-2
4-iodopyridine

: 504-24-5
4-aminopyridine

Conditions

Conditions	Yield
With copper(l) iodide; ascorbic acid In ammonia at 25℃; for 18h; liquid NH3;	97%

: 15854-87-2
4-iodopyridine

: 4526-06-1
trimethylsilyl-1,3-butadiyne

: 1480304-73-1
4-[(trimethylsilyl)buta-1,3-diyn-1-yl]pyridine

Conditions

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine In tetrahydrofuran at 20℃; for 3h; Sonogashira Cross-Coupling; Inert atmosphere;	97%

: 67237-53-0
3-ethynylthiophene

: 15854-87-2
4-iodopyridine

: 4-(thien-3-ylethynyl)pyridine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; diisopropylamine In tetrahydrofuran at 80℃; for 12h; Inert atmosphere;	97%

: 773837-37-9
sodium cyanide

: 15854-87-2
4-iodopyridine

: 100-48-1
pyridine-4-carbonitrile

Conditions

Conditions	Yield
With C18H14CuIN4 In acetonitrile at 20℃; for 24h; Inert atmosphere; Sealed tube; UV-irradiation;	97%

: 273-53-0
benzoxazole

: 15854-87-2
4-iodopyridine

: 2295-47-8
2-(pyridin-4-yl)benzoxazole

Conditions

Conditions	Yield
With copper(l) iodide; 2-(N-butyl-benzimidazol-2-yl)-6-(diphenylphosphinoxy)phenylchloropalladium(II); caesium carbonate In N,N-dimethyl-formamide at 120℃; for 18h; Inert atmosphere;	97%

: 15854-87-2
4-iodopyridine

: 107-19-7
propargyl alcohol

: 93524-95-9
3-(pyridin-4-yl)propane-2-yn-1-ol

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine Sonogashira coupling;	96%
With copper(l) iodide; iodophenylbis(triphenylphosphine)palladium; triethylamine In chloroform at 60℃; for 0.5h;	83%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 60℃;	80%

: 15854-87-2
4-iodopyridine

: 1628644-36-9
3,8-bis((4-ethynylphenyl)ethynyl)-1,10-phenanthroline

: C42H22N4

Conditions

Conditions	Yield
With copper(l) iodide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 60℃; for 168h;	96%

: 136466-94-9
(2,6-difluoropyridin-3-yl)boronic acid

: 15854-87-2
4-iodopyridine

: 1000982-00-2
2,6-difluoro-3-(4'-pyridyl)pyridine

Conditions

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane; water at 85℃; for 5h; Suzuki coupling;	95%

: 887925-07-7
N-ethynyl-4-methyl-N-{2-[(triisopropylsilanyl)-ethynyl]-phenyl}-benzenesulfonamide

: 15854-87-2
4-iodopyridine

: 1024670-31-2
2-(2-(triisopropylsilyl)ethynyl)-N-(2-(pyridin-4-yl)ethynyl)-N-tosylbenzenamine

Conditions

Conditions	Yield
With copper(l) iodide; triethylamine; tetrakis(triphenylphosphine) palladium(0) In toluene at 60℃; Sonogashira cross-coupling;	95%

: 15854-87-2
4-iodopyridine

: 1268247-73-9
3-bromoisothiazole-4-carbonitrile

: 1268247-94-4
3-bromo-5-(pyridin-4-yl)isothiazole-4-carbonitrile

Conditions

Conditions	Yield
With bis(triphenylphosphine)palladium(II) dichloride; silver fluoride; triphenylphosphine In acetonitrile at 20 - 82℃; for 20h;	95%

: 15854-87-2
4-iodopyridine

: potassium ferrocyanide

: 100-48-1
pyridine-4-carbonitrile

Conditions

Conditions	Yield
With mesoporous silica SBA-15 supported Cu2O nanoparticles In N,N-dimethyl-formamide at 120℃; for 8h; Green chemistry;	95%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 12h;	92%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 15h; Schlenk technique; Green chemistry;	90%

: 623-73-4
diazoacetic acid ethyl ester

: 15854-87-2
4-iodopyridine

: ethyl 2-diazo-2-(pyridin-4-yl) acetate

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); triethylamine; silver carbonate In toluene at 20℃; for 4h; Schlenk technique; Inert atmosphere;	95%

: 15854-87-2
4-iodopyridine

: 137-26-8
Thiram

: 89478-23-9
dimethyl-dithiocarbamic acid pyridin-4-yl ester

Conditions

Conditions	Yield
With copper(I) oxide; caesium carbonate In dimethyl sulfoxide at 80℃; for 18h; Sealed tube;	95%

: 15854-87-2
4-iodopyridine

: 111409-83-7
1-(triisopropylsilyl)butadiyne

: 4-((triisopropylsilyl)-buta-1,3-diyn-1-yl)pyridine

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; for 40h; Inert atmosphere;	95%

4-Iodopyridine Specification

The IUPAC name of this chemical is 4-iodopyridine. With the CAS registry number 15854-87-2, it is also named as Pyridine, 4-iodo-. The product's categories are blocks; iodides; pyridines; pyridines, pyrimidines, purines and pteredines; pharmacetical; halides; pyridines derivates; halogenated; organohalides; halopyridines; iodopyridines. It is white to off-white crystals which turns brown on storage. In addition, this chemical is sensitive to light and it should be stored in the freezer.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.76; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.75; (4)ACD/LogD (pH 7.4): 1.76; (5)ACD/BCF (pH 5.5): 12.45; (6)ACD/BCF (pH 7.4): 12.76; (7)ACD/KOC (pH 5.5): 210.15; (8)ACD/KOC (pH 7.4): 215.33; (9)#H bond acceptors: 1; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 0; (12)Index of Refraction: 1.629; (13)Molar Refractivity: 37.25 cm³; (14)Molar Volume: 104.7 cm³; (15)Polarizability: 14.76×10^-24 cm³; (16)Surface Tension: 48.9 dyne/cm; (17)Enthalpy of Vaporization: 43.33 kJ/mol; (18)Vapour Pressure: 0.217 mmHg at 25°C; (19)Exact Mass: 204.938842; (20)MonoIsotopic Mass: 204.938842; (21)Topological Polar Surface Area: 12.9; (22)Heavy Atom Count: 7; (23)Complexity: 50.

Uses of p-Iodopyridine: It can be used as pharmaceutical intermediate. And it is also used in organic synthesis. For example: It reacts with 1-methyl-pyrrole to get 4-(1-methyl-2-pyrrolyl)pyridine. This reaction needs solvent CH₂Cl₂ at ambient temperature and irradiation. The reaction time is 5 hours. The yield is 69%.

When you are using this chemical, please be cautious about it as the following:
It is irritating to eyes, respiratory system and skin. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you want to contact this product, you must wear suitable protective clothing.

People can use the following data to convert to the molecule structure.
1. SMILES: Ic1ccncc1;
2. InChI: InChI=1/C5H4IN/c6-5-1-3-7-4-2-5/h1-4H.

Product Name

4-Iodopyridine

Synthetic route

4-Iodopyridine Specification

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