2 6-DICHLORO-4-IODOPYRIDINE97
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2 6-DICHLORO-4-IODOPYRIDINE97
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CAS No:
98027-84-0
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Formula:
C5H2Cl2IN
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Chemical Name:
2 6-DICHLORO-4-IODOPYRIDINE97
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Synonyms:
2,6-Dichloro-4-iodopyridine 97%;2 6-DICHLORO-4-IODOPYRIDINE97;2,6-Dichloro-4-iodopyridine;Pyridine, 2,6-dichloro-4-iodo-
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CAS No:
2 6-DICHLORO-4-IODOPYRIDINE97 Basic Attributes
273.884
272.860901
1592732-453-0
DTXSID00471453
2933399090
Safety Information
IRRITANT
NONH for all modes of transport
3
22-37/38-41-43
26-36-36/37/39
Xn
P261-P280-P305 + P351 + P338
H302-H315-H317-H318-H335
|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
2 6-DICHLORO-4-IODOPYRIDINE97 Use and Manufacturing
Reagents and conditions: a) n-BuLi, ArBr; ZINC12 ; then 2, 6- dibromopyridine and cat. Pd (PPH3) 4 (95percent); b) LiOH, THF/H2O (100percent); C) (COCI) 2; NaN3 ; TFA; d) K2CO3, CH30H (78percent); e) HCI, CH3CN, NAN02 ; KI (52percent); f) n-BuLi, ArBr; ZINC12 ; then 13 and cat. Pd (PPh3) 4 (98percent); g) ArB (OH} 2, cat. Pd2 (dba) 3, cat. P (T-BU) 3, CS2CO3, (82percent); h) as (F) (71percent) ; i) as (g) (31percent) ; j) n-BuLi, ArBr; ZINC12 ; then 12 (80percent) ; k) 2- aminophenol, EDCI (97percent); 1) 230°C (87percent); m) ArB (OH) 2, cat. Pd2 (dba) 3, cat. [HP (T-BU) 3] BF4, CS2CO3 (78percent). Synthesis of 4 begins with pyridine derivative citrazinic acid. Treatment with POC13 at elevated temperature afforded the corresponding 2-6, dichloroisonicotinoyl chloride. To facilitate purification, the reaction was quenched with methanol; methyl ester 1 was isolated in 76percent yield after passage through a plug of silica gel to remove colored impurities. Saponification then provided acid 2 in quantitative yield without purification. Transformation to 3 was effected by conversion to the acyl azide, thermal Curtius rearrangement, and hydrolysis of the resulting trifluoroacetamide to provide 2, 6-DICHLORO-4-AMINOPYRIDINE (3), (Pfister, J. R. , Wymann, W. E. Synthesis 1983, 38). While this method for converting 2 to 3 is nominally 3 steps, it requires only a single extractive workup and the steps can thus be carried out in rapid succession. 3 was converted directly to 4 by diazotization and reaction with potassium iodide (it is necessary to stir 3 in cold hydrochloric acid for several hours prior to diazotization in order to obtain an acceptable yield) providing 4 in reasonable yield and excellent purity after trituration with acetone. This short sequence of reactions allows preparation of 4 IN-35percent overall yield, requires no chromatography beyond a single filtration through a plug of silica gel, and has allowed the routine preparation of 5-10 g quantities of this intermediate. Unlike many 4-halopyridines, 4 is stable for several months at room temperature if protected from light. 4 can be ready transformation to fluorophores of the present invention.
Computed Properties
Molecular Weight:273.88
XLogP3:3.4
Hydrogen Bond Acceptor Count:1
Exact Mass:272.86090
Monoisotopic Mass:272.86090
Topological Polar Surface Area:12.9
Heavy Atom Count:9
Complexity:91
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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