2,6-dichloro-4-iodopyridine
- Product Name
- 2,6-dichloro-4-iodopyridine
- CAS No.
- 98027-84-0
- Chemical Name
- 2,6-dichloro-4-iodopyridine
- Synonyms
- 2,6-Dichloro-4-iodopyridine;2,6-Dichloro-4-iodopyr;2,6-Dichloro-4-iodopyridine>Pyridine, 2,6-dichloro-4-iodo-;2 6-DICHLORO-4-IODOPYRIDINE 97;2,6-Dichloro-4-iodopyridine 97%;2 6-DICHLORO-4-IODOPYRIDINE 97 ISO 9001：2015 REACH
- CBNumber
- CB2498902
- Molecular Formula
- C5H2Cl2IN
- Formula Weight
- 273.89
- MOL File
- 98027-84-0.mol
2,6-dichloro-4-iodopyridine Property
- Melting point:
- 161-165 °C
- Boiling point:
- 291.6±35.0 °C(Predicted)
- Density
- 2.129±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- form
- powder to crystaline
- pka
- -3.19±0.10(Predicted)
- color
- White to Gray to Brown
- Sensitive
- Light Sensitive
- InChIKey
- NGSKFMPSBUAUNE-UHFFFAOYSA-N
Safety
- Hazard Codes
- Xn
- Risk Statements
- 22-37/38-41-43
- Safety Statements
- 26-36-36/37/39
- WGK Germany
- 3
- HazardClass
- IRRITANT
- HS Code
- 29333990
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Danger
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H317May cause an allergic skin reaction
H318Causes serious eye damage
H335May cause respiratory irritation
- Precautionary statements
-
P280Wear protective gloves/protective clothing/eye protection/face protection.
P302+P352IF ON SKIN: wash with plenty of soap and water.
N-Bromosuccinimide Price
- Product number
- 654078
- Product name
- 2,6-Dichloro-4-iodopyridine
- Purity
- 97%
- Packaging
- 1g
- Price
- $34.1
- Updated
- 2025/07/31
- Product number
- D4774
- Product name
- 2,6-Dichloro-4-iodopyridine
- Purity
- >98.0%(GC)
- Packaging
- 1g
- Price
- $65
- Updated
- 2025/07/31
- Product number
- D4774
- Product name
- 2,6-Dichloro-4-iodopyridine
- Purity
- >98.0%(GC)
- Packaging
- 5g
- Price
- $220
- Updated
- 2025/07/31
- Product number
- D435253
- Product name
- 2,6-Dichloro-4-iodopyridine
- Packaging
- 50mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- FD32638
- Product name
- 2,6-Dichloro-4-iodopyrimidine
- Packaging
- 5G
- Price
- $100
- Updated
- 2021/12/16
2,6-dichloro-4-iodopyridine Chemical Properties,Usage,Production
Chemical Properties
Off-white powder
Uses
2,6-dichloro-4-iodopyridine has useful structural, electronic, and optical properties， can be used for polysubstituted pyridines.
Synthesis
2587-02-2
98027-84-0
The general procedure for the synthesis of 2,6-dichloro-4-iodopyridine from 4-amino-2,6-dichloropyridine is as follows: Reagents and conditions: a) n-BuLi, ArBr; ZnCl2; followed by addition of 2,6-dibromopyridine and catalyst Pd(PPh3)4 (95% yield). b) LiOH, THF/H2O (100% yield). c) (COCl)2; NaN3; TFA. d) K2CO3, CH3OH (78% yield). e) HCl, CH3CN, NaNO2; KI (52% yield). f) n-BuLi, ArBr; ZnCl2; followed by the addition of 13 and catalyst Pd(PPh3)4 (98% yield). g) ArB(OH)2, catalyst Pd2(dba)3, catalyst P(t-Bu)3, Cs2CO3 (82% yield);. h) Same as step f (71% yield). i) Same as step g (31% yield). j) n-BuLi, ArBr; ZnCl2; followed by addition of 12 (80% yield); and k) 2-aminophenol, EDCI (97% yield); l) 230°C (87% yield); n-BuLi, ArBr; ZnCl2; followed by 12 (80% yield) l) 230°C (87% yield). m) ArB(OH)2, catalyst Pd2(dba)3, catalyst [HP(t-Bu)3]BF4, Cs2CO3 (78% yield). The synthesis of 4 began with the pyridine derivative citric acid. Treatment with POCl3 at elevated temperatures afforded the corresponding 2,6-dichloroisonicotinoyl chloride. To facilitate purification, the reaction was quenched with methanol; after passing a silica plug to remove colored impurities, the methyl ester 1 was isolated in 76% yield. Saponification then provided acid 2 in quantitative yield without purification. Conversion to 3 was achieved by conversion to acyl azides, thermal Curtius rearrangement and hydrolysis of the resulting trifluoroacetamide to give 2,6-dichloro-4-aminopyridine (3) (Pfister, JR, Wymann, WE Synthesis 1983,38). Although this method for converting 2 to 3 is nominally a 3-step process, it requires only a single post-extraction treatment so that these steps can be performed in rapid succession. Direct conversion of 3 to 4 by diazotization and reaction with potassium iodide (which must be stirred in cold hydrochloric acid for 3 h prior to diazotization to obtain acceptable yields) provides 4 in reasonable yields and with excellent purity after grinding with acetone. This short reaction sequence permits the preparation of 4 in 35% overall yield, does not require chromatography except for a single filtration through a silicone plug, and permits the routine preparation of 5-10 g amounts of this intermediate. Unlike many 4-halopyridines, 4 is stable at room temperature for several months if protected from light.4 can be readily converted to the fluorophore of this invention.
References
[1] Organic Letters, 2001, vol. 3, # 26, p. 4263 - 4265
[2] Patent: WO2004/46103, 2004, A2. Location in patent: Page 33-34; 39-40
[3] Organic Letters, 2003, vol. 5, # 7, p. 967 - 970
[4] Roczniki Chemii, 1959, vol. 33, p. 387,392
[5] Chem.Abstr., 1959, p. 18954
2,6-dichloro-4-iodopyridine Preparation Products And Raw materials
Raw materials
Preparation Products
2,6-dichloro-4-iodopyridine Suppliers
- Tel
- --
- Fax
- --
- brunschwig@brunschwig.nl
- Country
- The Netherlands
- ProdList
- 4996
- Advantage
- 67
View Lastest Price from 2,6-dichloro-4-iodopyridine manufacturers
- Product
- 2,6-Dichloro-4-iodopyridine 98027-84-0
- Price
- US $200.00-1.00/KG
- Min. Order
- 1KG
- Purity
- 99%, 99.5% Sublimated
- Supply Ability
- g-kg-tons, free sample is available
- Release date
- 2023-12-31
- Product
- 2 6-DICHLORO-4-IODOPYRIDINE 97 98027-84-0
- Price
- US $1.10/g
- Min. Order
- 1g
- Purity
- 99.00%
- Supply Ability
- 100 Tons min
- Release date
- 2021-09-01
- Product
- 2 6-DICHLORO-4-IODOPYRIDINE 97 98027-84-0
- Price
- US $2.00/KG
- Min. Order
- 1KG
- Purity
- 99%
- Supply Ability
- customise
- Release date
- 2018-08-09