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N-?????????

N-?????????
N-????????? ??? ???
?? ??:
516-12-1
???:
N-?????????
???(??):
N-?????????
???:
N-Iodosuccinimide
???(??):
NIS;1-iodopyrrolidine-2,5-dione;Iodosuccinimide;N-lodosuccinimide;N-IodosucciniMide (NIS);1-iodo-5-pyrrolidinedione;1-IODO-2,5-PYRROLIDINEDIONE;N-iododiimide;succiniodimide;N-Iodouccinimide
CBNumber:
CB0342078
???:
C4H4INO2
??? ??:
224.98
MOL ??:
516-12-1.mol
MSDS ??:
SDS

N-????????? ??

???
202-206 °C(lit.)
?? ?
249.6±23.0 °C(Predicted)
??
2,245 g/cm3
?? ??
2-8°C
???
???, ???????? ? ??????? ?????. ???? ?????? ???.
??? ??
??? ??
?? ?? (pKa)
-2.57±0.20(Predicted)
??
??-????? ????
???
??? ????
??
Moisture Sensitive
Merck
14,5045
BRN
113917
???
??? ???
InChI
1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2
InChIKey
LQZMLBORDGWNPD-UHFFFAOYSA-N
SMILES
IN1C(=O)CCC1=O
CAS ??????
516-12-1(CAS DataBase Reference)
??
  • ?? ? ?? ??
  • ?? ? ???? ?? (GHS)
??? ?? Xn,Xi
?? ???? ?? 22-36/37/38
????? 26-36-37/39
WGK ?? 3
RTECS ?? WN2817000
F ?????? 8-9
?? ?? ?? Harmful/Keep Cold/Moisture Sensitive
TSCA No
?? ?? IRRITANT
HS ?? 29251995
???? ??? 11 - Combustible Solids
Hazard Classifications Aquatic Acute 1
Aquatic Chronic 1
Eye Irrit. 2
Muta. 2
Skin Irrit. 2
Skin Sens. 1B
????(GHS): Exclamation Mark (GHS07)Health Hazard (GHS08)Environment (GHS09)
?? ?: Warning
??·?? ??:
?? ??·?? ?? ?? ?? ?? ?? ? ?? ?? P- ??
H315 ??? ??? ??? ????? ?? ????? ?? 2 ?? P264, P280, P302+P352, P321,P332+P313, P362
H317 ????? ?? ??? ??? ? ?? ?? ??? ?? ?? 1 ?? P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H319 ?? ?? ??? ??? ?? ? ?? ?? ??? ?? ?? 2A ?? P264, P280, P305+P351+P338,P337+P313P
H341 ???? ??? ??? ??? ??? (????? ???? ????? ???? ???? ???? ??? ?? ????? ??? ???? ??) ???? ???? ?? ?? 2 ?? P201,P202, P281, P308+P313, P405,P501
H410 ??? ??? ?? ????? ?? ??? ?? ????? ?? - ?? ?? 1 ?? P273, P391, P501
??????:
P201 ?? ? ?? ???? ?????.
P273 ???? ???? ???.
P280 ????/???/???/?????? ?????.
P302+P352 ??? ??? ??? ?? ????.
P305+P351+P338 ?? ??? ? ?? ?? ???? ????. ???? ?????? ?????. ?? ????.
P308+P313 ?? ?? ??? ???? ???? ??· ??? ????.
NFPA 704
1
2 0

N-????????? MSDS


1-Iodo-2,5-pyrrolidinedione

N-????????? C??? ??, ??, ??

??? ??

white-yellow to brown crystalline powder

??

N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis.

??

ChEBI: N-iodosuccinimide is a five-membered cyclic dicarboximide compound having an iodo substituent on the nitrogen atom. It is a dicarboximide and a pyrrolidinone. It derives from a succinimide.

?? ??

To a solution of 39.2g of succinimide in 1200ml of boiling water was added 51.0g of freshly precipitated silver oxide, the mixture was filtered and the silver salt was allowed to crystallize. Filtration and washing with cold water furnished 45.0g of the silver salt of succinimide suitable for the iodination step.
The finely powdered salt (49.5g) was added in portions with stirring to a solution of 50.8g of iodine in 300ml of acetone, the temperature being maintained at 5-10°C. After decolorization (30 min.), the silver iodide was filtered, the solvent was removed under reduced pressure at room temperature and the residue was washed with ether, yielding 43g of N-iodosuccinimide with mp 189-191°C. An analytical sample (85% recovery) was obtained by dissolving in the minimum quantity of hot dioxane and precipitating with carbon tetrachloride; colorless needles, mp 200-201°C.
Ref: JACS 75, 3493 (1953)

?? ??

N-Iodosuccinimide (NIS) is an iodinating agent that is used for various electrophilic iodinations and as source for iodine in radical reactions.
N-Iodosuccinimide is the least reactive of the N-haloamides in aromatic substitution. N-Iodosuccinimide does not act as an iodinating agent in pure dimethyl sulfoxide or N-ethylacetamide. On the other hand, butyl disulfide and a number of other sulfur-containing compounds are effective catalysts at low concentration for the iodination of guanosine derivatives using N-iodosuccinimide. This catalytic effect is observed when dimethyl sulfoxide is used as the solvent,but not when N-ethylacetamide is used.
https://www.organic-chemistry.org/chemicals/oxidations/n-iodosuccinimide-nis.shtm

Purification Methods

Crystallise it from dioxane/CCl4. It iodinates arenes in triflic acid. [Olah et al J Org Chem 58 3194 1993, Beilstein 21/9 V 544.]

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