Indane or indan is an
organic compound with the formula C
6H
4(CH
2)
3. It is a colorless liquid
hydrocarbon. It is a
petrochemical, a bicyclic compound. It occurs at the level of about 0.1% in
coal tar. It is usually produced by hydrogenation of
indene.
[Karl Griesbaum, Arno Behr, Dieter Biedenkapp, Heinz-Werner Voges, Dorothea Garbe, Christian Paetz, Gerd Collin, Dieter Mayer, Hartmut Höke "Hydrocarbons" in Ullmann's Encyclopedia of Industrial Chemistry 2002 Wiley-VCH, Weinheim. ]
Reactions
Indane can also be converted in a catalytic reactor to other aromatics such as
xylene.
Indane is used in the synthesis of
sulofenur.
Derivatives
Derivatives include compounds such as 1-methylindane and 2-methylindane (where one methyl group is attached to the five carbon ring), 4-methylindane and 5-methylindane (where one methyl group is attached to the benzene ring), and various dimethylindanes. Other derivatives can be obtained indirectly, e.g. the reaction of
diethyl phthalate
Diethyl phthalate (DEP) is a phthalate ester. It occurs as a colourless liquid without significant odour but has a bitter, disagreeable taste. It is more dense than water and insoluble in water; hence, it sinks in water.
Synthesis and application ...
with
ethyl acetate, using metallic
sodium and
ethanol as a catalyst. The reaction yields indanedione ethyl ester, which can react with the sodium ions yielding a salt. This can be reversed by adding an aqueous solution of
hydrochloric acid.
A family of indane derivatives are
empathogen-entactogens. They are very close derivatives of other empathogen-entactogens such as
MDMA and
MDA
MDA, mda, or ''variation'', may refer to:
Places
* Moldova, a country in Europe with the ISO 3166-1 country code MDA Politics
* Meghalaya Democratic Alliance (2018), ruling coalition government in the Indian State of Meghalaya led by National Pe ...
. Examples include
MDAI
MDAI (5,6-methylenedioxy-2-aminoindane) is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly binding selectivity, selective serotonin releasing agent (SSRA) ''in vitro'' a ...
and
MDMAI
5,6-Methylenedioxy-''N''-methyl-2-aminoindane (MDMAI), is a drug developed in the 1990s by a team led by David E. Nichols at Purdue University. It acts as a non-neurotoxic and highly selective serotonin releasing agent (SSRA) in animals and a ...
.
Nichols also created an indane isomer of
amphetamine
Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
,
2-aminoindane,
NM-2-AI
NM-2-AI (''N''-methyl-2-aminoindane) is a psychoactive drug and research chemical that has been sold online as a designer drug. It is a rigid analogue of methamphetamine. It is a derivative of 2-aminoindane.
NM-2-AI acts as a non-neurotoxic an ...
, and an iodized derivative
5-IAI
5-Iodo-2-aminoindane (5-IAI) is a drug which acts as a releasing agent of serotonin, norepinephrine, and dopamine. It was developed in the 1990s by a team led by David E. Nichols at Purdue University. 5-IAI fully substitutes for MDMA in rodents ...
.
See also
*
Indene
*
1,3-indandione
References
{{Reflist