Reaction Mechanism of SmI2-mediated Reactions
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SAMARIUM(II) IODIDE

Reaction Mechanism of SmI2-mediated Reactions
Product Name
SAMARIUM(II) IODIDE
CAS No.
32248-43-4
Chemical Name
SAMARIUM(II) IODIDE
Synonyms
SAMARIUM IODIDE;Samarium iodide (SmI2);Diiodosamarium(II);SAMARIUM(II) IODIDE;Samarium(ll) iodide;0.1MinTHF,stabilized;Samarium(II) diiodide;Samarium(Ii)Iodide,0.1;SaMariuM(II) Iodide samarium(ii) iodide solution
CBNumber
CB5168664
Molecular Formula
I2Sm
Formula Weight
404.17
MOL File
32248-43-4.mol
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SAMARIUM(II) IODIDE Property

Melting point:
526 ±3°
Boiling point:
solid: 1580℃ [CRC10]
Density 
0.922 g/mL at 25 °C
Flash point:
−2 °F
storage temp. 
2-8°C
solubility 
reacts with H2O
form 
powder
color 
Deep blue-green
Sensitive 
Air & Moisture Sensitive
Merck 
14,8349
Exposure limits
ACGIH: TWA 50 ppm; STEL 100 ppm (Skin)
OSHA: TWA 200 ppm(590 mg/m3)
NIOSH: IDLH 2000 ppm; TWA 200 ppm(590 mg/m3); STEL 250 ppm(735 mg/m3)
InChIKey
UAWABSHMGXMCRK-UHFFFAOYSA-L
CAS DataBase Reference
32248-43-4(CAS DataBase Reference)
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Safety

Hazard Codes 
F,Xi,Xn
Risk Statements 
11-19-36/37-40
Safety Statements 
16-29-33-36/37-26
RIDADR 
UN 2056 3/PG 2
WGK Germany 
3
1-10
HazardClass 
3
PackingGroup 
II
HS Code 
28276000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H225Highly Flammable liquid and vapour

H260In contact with water releases flammable gases which may ignite spontaneously

H302Harmful if swallowed

H314Causes severe skin burns and eye damage

H315Causes skin irritation

H318Causes serious eye damage

H319Causes serious eye irritation

H335May cause respiratory irritation

H351Suspected of causing cancer

H371May cause damage to organs

H372Causes damage to organs through prolonged or repeated exposure

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P223Keep away from any possible contact with water, because of violent reaction and possible flash fire.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P370+P378In case of fire: Use … for extinction.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

P403+P235Store in a well-ventilated place. Keep cool.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
347116
Product name
Samarium(II) iodide solution
Purity
0.1 M in THF, contains samarium chips as stabilizer
Packaging
4x25ml
Price
$126
Updated
2024/03/01
Sigma-Aldrich
Product number
347116
Product name
Samarium(II) iodide solution
Purity
0.1 M in THF, contains samarium chips as stabilizer
Packaging
1l
Price
$403
Updated
2024/03/01
TCI Chemical
Product number
S0494
Product name
Samarium(II) Iodide (ca. 0.1mol/L in Tetrahydrofuran)
Packaging
25mL
Price
$63
Updated
2024/03/01
TCI Chemical
Product number
S0494
Product name
Samarium(II) Iodide (ca. 0.1mol/L in Tetrahydrofuran)
Packaging
100mL
Price
$249
Updated
2024/03/01
Alfa Aesar
Product number
022360
Product name
Samarium(II) iodide, 0.07 - 0.12M in THF, stab.
Packaging
100ml
Price
$73.65
Updated
2024/03/01
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SAMARIUM(II) IODIDE Chemical Properties,Usage,Production

Reaction

SmI2 has been used extensively in literature due to its large reduction potential. Known as a single-electron transfer reagent.

Mechanism of SmI2-mediated Reactions

Radicals and anions from organohalides

Reduction of halides: iodides > bromides > chloride


reaction carried out at 60 °C

Description

Samarium(II) iodide, SmI2, when employed as a solution for organic synthesis, is known as “Kagan’s reagent.” SmI2 is a green solid and its solutions are green as well. It is a strong one-electron reducing agent that is used in organic synthesis. Solid, solvent-free SmI2 forms by high-temperature decomposition of samarium(III) iodide (SmI3).

Chemical Properties

Deep bleu-green solution

Uses

Samarium(II) iodide solution (SmI2) can be used as a reagent in the synthesis of:

  • Benzannulated pyrrolizidines and indolizidines by SmI2-induced cyclizations of indole derivatives.
  • Chiral 4-substituted 2-oxazolidinones and 5,5-disubstituted oxazolidinones through asymmetric Reformatsky type reaction.
  • γ-Aminoalkyl substituted γ-butyrolactones via ketyl-alkene coupling reaction.

It can also be used in:
  • Reduction of conjugated double and triple bonds into alkenes using SmI2/H2O/amine mixtures.
  • Conversion of β-hydroxyketones into 1,3-diols by SmI2/H2O/Et3N.
  • Selective reduction of 6-membered lactones to the corresponding diols/triols using SmI2-H2O reagent system.

SmI2 is an effective single-electron reducing agent for the promotion of ketone-olefin, ketyl aryl cyclizations, and pinacol coupling reactions under mild conditions. Often both intramolecular and intermolecular couplings proceed in a highly stereoselective fashion. It is also used in the synthesis of new heteroleptic samarium aryloxide/cyclopentadienide complexes.

Uses

In organic synthesis and electron transfer reactions; in discharge lamps.

Purification Methods

A possible impurity is SmI3 from which it is made. If present, grind the solid to a powder and heat it in a stream of pure H2. The temperature (~ 500-600o) should be below the m (~ 628o) of SmI3, since the molten compounds react very slowly. [Wetzel in Handbook of Preparative Inorganic Chemistry (Ed. Brauer) Academic Press Vol II pp 1149, 1150 1965.]

SAMARIUM(II) IODIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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SAMARIUM(II) IODIDE Suppliers

Huangshi Bo’Er Chemical Co., Ltd.
Tel
0714-6401888 18671400300
Fax
0714-6401888
Email
273568016@qq.com
Country
China
ProdList
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Panjin Infinity Scientific CO. LTD
Tel
400-1062016 18612996721
Fax
QQ25788917
Email
hao@infsci.com
Country
China
ProdList
327
Advantage
58
Infinity SCI
Tel
400-400-1062016 17800804092
Email
admin@infsci.com
Country
China
ProdList
626
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55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
021-61259108 18621169109
Fax
86-21-61259102
Email
market03@meryer.com
Country
China
ProdList
40228
Advantage
62
Beijing Donghualituo Techonlogy Development Co.,Ltd.
Tel
010-88425576
Fax
(+86)-10-88425546
Email
sales@dhltchem.com
Country
China
ProdList
793
Advantage
59
Alfa Aesar
Tel
400-6106006
Fax
021-67582001/03/05
Email
saleschina@alfa-asia.com
Country
China
ProdList
30123
Advantage
84
TCI (Shanghai) Development Co., Ltd.
Tel
021-67121386
Fax
021-67121385
Email
Sales-CN@TCIchemicals.com
Country
China
ProdList
24529
Advantage
81
Beijing HwrkChemical Technology Co., Ltd
Tel
010-89508211 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
8415
Advantage
55
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44689
Advantage
61
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View Lastest Price from SAMARIUM(II) IODIDE manufacturers

Career Henan Chemical Co
Product
SAMARIUM(II) IODIDE 32248-43-4
Price
US $1.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
20kg
Release date
2019-07-04

32248-43-4, SAMARIUM(II) IODIDERelated Search:


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  • Samarium(ll) iodide
  • 32248-43-4
  • SmIxx2
  • I2Sm
  • SmI2
  • Synthetic Reagents
  • Others
  • Reduction
  • Classes of Metal Compounds
  • Sm (Samarium) Compounds
  • Transition Metal Compounds
  • Other Metal
  • metal halide
  • OthersChemical Synthesis
  • Catalysis and Inorganic Chemistry
  • Reduction
  • Salts
  • Samarium Salts
  • SamariumMetal and Ceramic Science
  • Synthetic Reagents
  • Crystal Grade Inorganics
  • Classes of Metal Compounds
  • Sm (Samarium) Compounds
  • Transition Metal Compounds