N-Iodosuccinimide

Iupac Name：1-iodopyrrolidine-2,5-dione

Molecular Weight：224.985

Modify Date.: 2022-11-08 17:36

Introduction: N-Iodosuccinimide is a iodo substituted succinimide that is used as an iodinating agent in chemical synthesis. View more+

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1. Names and Identifiers

1.1 Name: N-Iodosuccinimide
1.2 Synonyms: 1-IODO-2,5-PYRROLIDINEDIONE 1-iodo-5-pyrrolidinedione 1-Iodopyrrolidine-2,5-dione, 2,5-Dioxo-1-iodopyrrolidine 2,5-Pyrrolidinedione, 1-iodo- N-Iodosuccinimide , (1-Iodo-2,5-pyrrolidinedione) NIS Succinimide, N-iodo- Succiniodimide

1.3 CAS No.: 516-12-1

1.4 CID: 120273

1.5 EINECS(EC#): 208-221-6

1.6 Molecular Formula: C4H4INO2 (isomer)

1.7 Inchi: InChI=1S/C4H4INO2/c5-6-3(7)1-2-4(6)8/h1-2H2

1.8 InChkey: LQZMLBORDGWNPD-UHFFFAOYSA-N

1.9 Canonical Smiles: C1CC(=O)N(C1=O)I

1.10 Isomers Smiles: C1CC(=O)N(C1=O)I

2. Properties

2.1 Density: 2.31

2.1 Melting point: 197-204℃ (dec.)

2.1 Boiling point: 249.6 °C at 760 mmHg

2.1 Refractive index: 1.653

2.1 Flash Point: 104.8 °C

2.1 Precise Quality: 224.92900

2.1 PSA: 37.38000

2.1 logP: 0.42330

2.1 Solubility: Soluble in dioxane, tetrahydrfuran and acetonitrile. Insoluble in ether and carbon tetrachloride.

2.2 Appearance: white to off-white powder

2.3 Storage: Keep Cold. Moisture Sensitive. Light Sensitive.

2.4 Chemical Properties: white-yellow to brown crystalline powder

2.5 Color/Form: White-yellow to brown

2.6 pKa: -2.57±0.20(Predicted)

2.7 Water Solubility: decomposes

2.8 Stability: Stable at room temperature in closed containers under normal storage and handling conditions.

2.9 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A five-membered cyclic dicarboximide compound having an iodo substituent on the nitrogen atom.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 56 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 7 of 56 companies. For more detailed information, please visit ECHA C&L website

Of the 9 notification(s) provided by 49 of 56 companies with hazard statement code(s):

H302 (93.88%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (97.96%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (97.96%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (93.88%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 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.] N-Iodosuccinimide Preparation Products And Raw materials Preparation Products

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

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xn

4.1 Signal Word: Warning

4.1 Risk Statements: R22;R36/37/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H302; H315; H319; H335

4.1 RIDADR: 25kgs

4.1 WGK Germany: 3

4.1 RTECS: WN2817000

4.1 Safety: Hazard Codes Xn,Xi
Risk Statements 22-36/37/38
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36-37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
S37/39:Wear suitable gloves and eye/face protection.

4.2 Sensitive: Moisture Sensitive

4.3 Specification: N-Iodosuccinimide (CAS NO.516-12-1) is a white-yellow to brown crystalline powder,be sensitive to water and ligh.In organic synthesis for ketones, aldehydes of iodide, primarily as a pharmaceutical intermediates in the biological drug, its production method is without light conditions, in reaction of succinimide and silver oxide, Preparation N-succinic imide silver, in dry dioxane in the reaction ti get N-iodo succinimide.

4.4 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	180mg/kg (180mg/kg)		U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#02815,

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Skin irritation, Category 2

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H315 Causes skin irritation H319 Causes serious eye irritation H335 May cause respiratory irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : in DMSO-d6

13C NMR : Predict

1H NMR : parameter in DMSO-d6

1H NMR : Predict

Predict 1H proton NMR

IR : KBr disc

IR : nujol mull

7. Synthesis Route

516-12-1Total: 4 Synthesis Route

128-08-5 407 Suppliers

516-12-1 219 Suppliers

Literatures:
Chaikovskii; Skorokhodov; Filimonov Russian Journal of Organic Chemistry, 2001 , vol. 37, # 10 p. 1503 - 1504
Yield: ~77%

123-56-8 202 Suppliers

516-12-1 219 Suppliers

Literatures:
Soundararajan, R.; Krishnamurthy, S.; Srinivasan, Vilanoor S.; Balasubramanian, T.R. Journal of Organometallic Chemistry, 1983 , vol. 255, # 3 p. 295 - 298
Yield: null

128-09-6 244 Suppliers

516-12-1 219 Suppliers

Literatures:
Poriel, Cyril; Lachia, Mathilde; Wilson, Claire; Davies, James R.; Moody, Christopher J. Journal of Organic Chemistry, 2007 , vol. 72, # 8 p. 2978 - 2987
Yield: null

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8. Precursor and Product

precursor:

7553-56-2

128-08-5

128-09-6

123-56-8

product :

82621-86-1

875781-18-3

116625-47-9

642460-96-6

66222-29-5

69381-32-4

3027-06-3

155928-39-5

123-56-8

123148-78-7

132131-24-9

33348-34-4

34671-29-9

908267-60-7

36044-42-5

77256-26-9

View all

9. Other Information

9.0 Usage: N-Iodosuccinimide is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. It is also used to hydrolyze thioglycosides to 1-hydroxyglycosides with triluoroacetic acid. It is involved in the preparation of iodobenzene from 1,6-diynes. Further, it acts as an iodinating agent in chemical synthesis.

10. Computational chemical data

Molecular Weight: 224.985g/mol
Molecular Formula: C₄H₄INO₂
Compound Is Canonicalized: True
XLogP3-AA: -0.2
Exact Mass: 224.92868
Monoisotopic Mass: 224.92868
Complexity: 129
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 0
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 37.4
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBiMAAAAgAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgAAAAAACACBgAAAAAIAAAAIAAEQEAAAAAAAAAAAAAEAAAAAABAAgAAEAAAABCCAAAAFAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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