55123-01-8

Basic information

• Product Name: (2S)-2-(1-Methylethyl)oxirane
• Synonyms: (2S)-2-(1-Methylethyl)oxirane;(S)-Isopropyloxirane;(2S)-2-propan-2-yloxirane
• CAS NO: 55123-01-8
• Molecular Formula: C₅H₁₀O
• Molecular Weight: 86.13
• Mol File: 55123-01-8.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 75 ºC
• Flash Point: -8 ºC
• Appearance: /
• Density: 0.893
• CAS DataBase Reference: (2S)-2-(1-Methylethyl)oxirane(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-(1-Methylethyl)oxirane(55123-01-8)
• EPA Substance Registry System: (2S)-2-(1-Methylethyl)oxirane(55123-01-8)

Safety Data

• Hazardous Substances Data: 55123-01-8(Hazardous Substances Data)

Usage

General Description

(2S)-2-(1-Methylethyl)oxirane, also known as isopropyl epoxide, is a chemical compound with the molecular formula C5H10O. It is a colorless liquid with a fruity odor, and it is commonly used as an intermediate in the synthesis of pharmaceuticals and other organic compounds. Isopropyl epoxide is primarily used as a reactive intermediate in the manufacture of pesticides, flavoring agents, and fragrances. It is also used in the production of epoxide resins, which are widely utilized in the production of adhesives, coatings, and plastics. Isopropyl epoxide is considered to have low toxicity, but it should be handled with care due to its potential to irritate the skin and respiratory system.

Upstream product

• 1438-14-8 2-isopropyloxirane 
• 140388-27-8 (R)-2-chloro-3-methylbutan-1-ol 
• 563-45-1 3-Methyl-1-butene 
• 204686-68-0 Toluene-4-sulfonic acid (S)-3-methyl-2-(tetrahydro-pyran-2-yloxy)-butyl ester 
• 204686-66-8 methyl (2S)-3-methyl-2-(tetrahydro-2H-pyran-2-yloxy)butanoate 
• 204686-67-9 (2S)-3-methyl-2-(tetrahydropyran-2-yloxy)butan-1-ol 
• 204686-71-5 (S)-2-Isopropyl-1,4-dioxa-spiro[4.5]decane 
• 24347-63-5 methyl (S)-2-hydroxy-3-methylbutanoate 
• 17407-55-5 (S)-2-Hydroxy-3-methylbutanoic acid 
• 72-18-4 L-valine 
• 24347-56-6 (S)-3-methylbutane-1,2-diol 
• 90211-82-8 (2S)-1-tosyloxy-3-methylbutan-2-ol 

Downstream Products

• 160069-23-8 (S)-1-(N,N-dibenzylamino)-3-methyl-2-butanol 
• 1416148-66-7 (S)-3-mesyloxy-4-methyl-1-phenylpentane 
• 1416148-68-9 (S)-3-mesyloxy-4-methyl-1-phenylpentane 
• 27460-26-0 24(R)-Hydroxycholesterol 
• 15272-24-9 edulitine 
• 159973-38-3 (+)-(2'R)-3-(2'-hydroxy-3'-methylbutyl)-2,4,8-trimethoxyquinoline 
• 90211-85-1 (24R)-6β-methoxy-22-phenylsulfonyl-24-hydroxy-3α,5α-cyclocholestane 

Relevant articles and documents

Azidolysis of epoxides catalysed by the halohydrin dehalogenase from Arthrobacter sp. AD2 and a mutant with enhanced enantioselectivity: an (S)-selective HHDH

Halohydrin dehalogenase from Arthrobacter sp. AD2 catalysed azidolysis of epoxides with high regioselectivity and low to moderate (S)-enantioselectivity (E?=?1–16). Mutation of the asparagine 178 to alanine (N178A) showed increased enantioselectivity towards styrene oxide derivatives and glycidyl ethers. Conversion of aromatic epoxides was catalysed by HheA-N178A with complete enantioselectivity, however the regioselectivity was reduced. As a result of the enzyme-catalysed reaction, enantiomerically pure (S)-β-azido alcohols and (R)-α-azido alcohols (ee???99%) were obtained.

Cyclopropenone catalyzed substitution of alcohols with mesylate ion

The cyclopropenone catalyzed nucleophilic substitution of alcohols by methanesulfonate ion with inversion of configuration is described. This work provides an alternative to the Mitsunobu reaction that avoids the use of azodicarboxylates and generation of hydrazine and phosphine oxide byproducts. This transformation is shown to be compatible with a range of functionality. A cyclopropenone scavenge strategy is demonstrated to aid purification.

Stereoselective Synthesis of Squalamine Dessulfate

Squalamine dessulfate (24R) and the unnatural product squalamine dessulfate (24S) have been synthesized from stigmasterol.The key step is establishing the C24 stereochemistry is attachment of the sidechain at C22 using either (2R)- or (2S)-1,2-epoxy-3-met