Dinitro-''ortho''-cresol (DNOC) is an
organic compound with the
structural formula
The structural formula of a chemical compound is a graphic representation of the molecular structure (determined by structural chemistry methods), showing how the atoms are possibly arranged in the real three-dimensional space. The chemical bondi ...
CH
3C
6H
2(NO
2)
2OH. It is a yellow solid that is only slightly soluble in water. DNOC and some related derivatives have been used as
herbicide
Herbicides (, ), also commonly known as weedkillers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page fo ...
s.
Preparation
This compound is prepared by di
sulfonation of
''o''-cresol. The resulting disulfonate is then treated with nitric acid to give DNOC. A variety of related
derivatives
The derivative of a function is the rate of change of the function's output relative to its input value.
Derivative may also refer to:
In mathematics and economics
* Brzozowski derivative in the theory of formal languages
* Formal derivative, an ...
are known including those where the methyl group is replaced by ''sec''-butyl (
dinoseb), ''tert''-butyl (
dinoterb), and 1-methylheptyl (
dinocap). These are prepared by the direct
nitration of the
alkyphenols.
Applications and safety
This
toxicant is an
uncoupler, which means that it interferes with
adenosine triphosphate (ATP) production.
Symptoms of dinitro-''ortho''-cresol poisoning, due to ingestion or other forms of exposure, include confusion,
headache
Headache is the symptom of pain in the face, head, or neck. It can occur as a migraine, tension-type headache, or cluster headache. There is an increased risk of depression in those with severe headaches.
Headaches can occur as a result ...
, shortness of breath, and
sweating.
References
{{reflist
External links
World Health Organization
Uncoupling agents
Nitrotoluenes
Cresols
Dinitrophenols