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10025-82-8 - Indium(III) chloride, anhydrous, 98+% - L18758 - Alfa Aesar

L18758 Indium(III) chloride, anhydrous, 98+%

CAS Number
10025-82-8
Synonyms

Size Price ($) Quantity Availability
5g 40.17
25g 144.20
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Indium(III) chloride, anhydrous, 98+%

MDL
MFCD00011058
EINECS
233-043-0

Chemical Properties

Formula
InCl3
Formula Weight
221.18
Melting point
586°
Boiling Point
800°
Density
3.460
Sensitivity
Hygroscopic
Solubility
Soluble in water and tetrahydrofuran. Sparingly soluble in alcohol and insoluble in ether.

Applications

Indium(III) chloride is used in famous organic reactions such as Friedel-Crafts acylation and Diels-Alder reaction as a lewis acid catalyst. It is an efficient catalyst for thioacetalization and its chemoselectivity. It catalyzes the enantioselective ring-opening of meso-aziridines with thiols.

Notes

Hygroscopic. Incompatible with strong acids and strong oxidizing agents. The molten state of indium(III) chloride may conduct electricity.

Literature References

Mild, water tolerant Lewis acid catalyst, e.g. in allylation reactions of sensitive aldehydes with allyltributyltin: J. Org Chem., 61, 105 (1996). The allylstannane can also be generated in situ from the allyl halide in water: Tetrahedron Asym., 7, 1535 (1996). Catalyzes the Mukaiyama aldol reaction, under either solvent-free conditions: Tetrahedron Lett., 39, 1579 (1998), or in water: Chem. Commun., 1819 (1996); 861 (1998); Tetrahedron Lett., 38, 3465 (1997). For Diels-Alder reactions in water, see: Chem. Commun., 2315 (1996).

Promotes efficient azidolysis of ɑß-epoxy carboxyl derivatives in water at pH 4, with results superior to Yb(OTf)3 or Sc(OTf)3: J. Org. Chem., 66, 3554 (2001).

In combination with a dithiol, catalyzes the efficient transthioacetalization of acetals to dithioacetals: Synlett, 727 (2002).

Aldoximes can be dehydrated to nitriles; ketoximes undergo the Beckmann rearrangement to amides: Chem. Commun., 1196 (2000).

Indium enolates are readily formed by transmetallation of Li enolates. These undergo Reformatsky-type reactions with aldehydes to give ß-hydroxy esters. ɑ-Bromo enolates give Darzens-type ɑß-epoxy carbonyl compounds: J. Chem. Soc., Perkin 1, 825 (2000).

Catalyst for conjugate addition of indoles to electron-deficient alkenes: Synthesis, 2165 (2001):

The combination with NaBH4 has been reported to be an effective radical reducing system, replacing the environmentally unfavorable TBTH (Tri-n-butyl­tin hydride, A13298), e.g. in dehalogenation and cyclization reactions: J. Am. Chem. Soc., 124, 906 (2002).

In combination with Triethyl­silane, A10320 and a radical initiator, generates a radical reagent, analogous to Tri-n-butyl­tin hydride, A13298: Org. Lett., 6, 4981 (2004).

For a brief feature on InCl3, see: Synlett, 531 (2002). For reviews of the use of In compounds in organic synthesis, see: Eur. J. Org. Chem., 2347 (2000); J. Chem. Soc., Perkin 1, 3015 (2000).

/n

Onishi, Y.; Nishimoto, Y.; Yasuda, M.; Baba, A. Indium Chloride Catalyzed Alkylative Rearrangement of Propargylic Acetates Using Alkyl Chlorides, Alcohols, and Acetates: Facile Synthesis of alpha-Alkyl-alpha,beta-Unsaturated Carbonyl Compounds. Org. Lett. 2014, 16 (4), 1176-1179.

Akiyama, K.; Yamamoto, K.; Mineno, T.; Okawa, M.; Kinjo, J.; Yoshimitsu, H.; Nohara, T.; Ono, M. Five New Resin Glycoside Derivatives Isolated from the Convolvulin Fraction of Seeds of Quamoclit pennataafter Treatment with Indium(III) Chloride in Methanol. Chem. Pharm. Bull. 2014, 62 (1), 125-133.

GHS Hazard and Precautionary Statements

Hazard Statements: H314-H318-H302

Causes severe skin burns and eye damage. Causes serious eye damage. Harmful if swallowed.

Precautionary Statements: P260-P280-P303+P361+P353-P305+P351+P338-P301+P330+P331-P304+P340-P310-P301+P312-P405-P501a

Do not breathe dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Immediately call a POISON CENTER or doctor/physician. Call a POISON CENTER or doctor/physician if you feel unwell. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,4958
Hazard Class
8
Packing Group
II
Harmonized Tariff Code
2827.39
TSCA
Yes
RTECS
NL1400000

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