88916-22-7

Basic information

• Product Name: (2E)-1-[(1-methylethyl)sulfanyl]but-2-ene
• Synonyms: trans-1-(Isopropylthio)-2-butene
• CAS NO: 88916-22-7
• Molecular Formula: C₇H₁₄S
• Molecular Weight: 130.2511
• Mol File: 88916-22-7.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 161.8°C at 760 mmHg
• Flash Point: 41.6°C
• Density: 0.856g/cm³
• Vapor Pressure: 2.92mmHg at 25°C
• Refractive Index: 1.47
• CAS DataBase Reference: (2E)-1-[(1-methylethyl)sulfanyl]but-2-ene(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-1-[(1-methylethyl)sulfanyl]but-2-ene(88916-22-7)
• EPA Substance Registry System: (2E)-1-[(1-methylethyl)sulfanyl]but-2-ene(88916-22-7)

Safety Data

• Hazardous Substances Data: 88916-22-7(Hazardous Substances Data)

Usage

Description

(2E)-1-[(1-methylethyl)sulfanyl]but-2-ene, commonly known as 2-methylthiobut-2-ene or isobutyl mercaptan, is a four-carbon organic compound with a double bond between the second and third carbons and a thiol group attached to the third carbon. It is a highly volatile liquid with a foul, skunk-like odor.

Uses

Used in Flavor and Fragrance Industry:
(2E)-1-[(1-methylethyl)sulfanyl]but-2-ene is used as a flavoring agent for adding a pungent, animalic note to various products. Its strong, distinctive odor makes it suitable for creating realistic and natural scents in perfumes, colognes, and other fragrances.
Used in Natural Gas Industry:
(2E)-1-[(1-methylethyl)sulfanyl]but-2-ene can be found as an impurity in natural gas, and is responsible for the characteristic odor of skunks. Its presence in natural gas helps to detect gas leaks, ensuring safety and preventing accidents.

Upstream product

• 65672-48-2 4-(i-propylthio)-1-butene 
• 88915-94-0 (Z)-1-(i-propylthio)-2-butene 
• 121222-72-8 (E)-1-Isopropylsulfanyl-but-1-ene 
• 75-33-2 2-propanethiol 
• 591-97-9 1-chloro-2-butene 

Downstream Products

• 88915-95-1 (E)-2-Isopropylsulfanyl-1-phenyl-pent-3-en-1-ol 
• 88915-97-3 (Z)-4-Isopropylsulfanyl-2-methyl-1-phenyl-but-3-en-1-ol 
• 88916-00-1 (Z)-4-Isopropylsulfanyl-2-methyl-1-phenyl-but-3-en-1-ol 
• 88915-96-2 (E)-4-Isopropylsulfanyl-2-methyl-1-phenyl-but-3-en-1-ol 

Relevant articles and documents

Structure-Stability Relationships in Vinyl Sulfides. III. Stabilization Caused by Different Alkylthio and Phenylthio Groups Attached to an Olefinic Double Bond

The stabilization energies of different alkylthio and phenylthio groups attached to an olefinic double bond have been evaluated with respect to the energy differences of the isomerization reactions of some unsaturated sulfides, in which the double bond migrates from the β,γ- to the α,β-position.According to these results the stabilization energies (in kJ mol-1) are: MeS 15.6, EtS 14.8, i-PrS 15.7, t-BuS 17.5 and PhS 14.4

Regiochemical Convergence in the Reaction of Heterosubstituted Allylic Carbanions via Allylic Aluminum and Boron "Ate" Complexes

The regiochemistry in reactions of heterosubstituted allylic carbanions (1) is highly controlled via allylic aluminum or boron "ate" complexes which direct both carbonyl compounds and reactive halides to the α-position with high regioselectivity.For example, carbonyl compounds react with the oxygen- (3), sulfur- (12), selenium- (20), and silicon- (25) substituted allylic carbanions at the α-position via the ate complexes.Although the reactions of the ate complexes (2) with aldehydes generally produce a mixture of erythro and threo isomers, the aluminum ate comlex of 3b gives the erythro isomer (5) with very high stereoselectivity.This procedure is applied to the stereoselective synthesis of exo-brevicomin (9).With allylic halides, the oxygen- (3a) and sulfur- (12) substituted allylic carbanions again react at the α-position via the ate complexes.However, the coupling mode is entirely different; the α-α' coupling product (10) is obtained from 3a, while the α-γ' coupling product (15) is produced from 12.