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3-Dimethylaminophenol
[CAS# 99-07-0]

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Complete supplier list of 3-Dimethylaminophenol
Identification
Classification Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Pyridine compound >> Iodopyridine
Name 3-Dimethylaminophenol
Synonyms N,N-Dimethyl-3-aminophenol
Molecular Structure CAS # 99-07-0, 3-Dimethylaminophenol, N,N-Dimethyl-3-aminophenol
Molecular Formula C8H11NO
Molecular Weight 137.18
CAS Registry Number 99-07-0
EC Number 202-727-0
SMILES CN(C)C1=CC(=CC=C1)O
Properties
Density 1.1±0.1 g/cm3 Calc.*
Melting point 82 - 84 ºC (Expl.)
Boiling point 266.5 ºC 760 mmHg (Calc.)*, 265 - 268 ºC (Expl.)
Flash point 132.7±18.5 ºC (Calc.)*, 148 ºC (Expl.)
Index of refraction 1.59 (Calc.)*
* Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbols symbol   GHS07 Warning    Details
Hazard Statements H315-H319-H335    Details
Precautionary Statements P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501    Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Specific target organ toxicity - single exposureSTOT SE3H335
Eye irritationEye Irrit.2H319
Acute toxicityAcute Tox.4H302
Acute toxicityAcute Tox.4H332
Acute toxicityAcute Tox.4H312
Eye irritationEye Irrit.2AH319
SDS Available
up Discovory and Applicatios
3-Dimethylaminophenol is an aromatic compound with the molecular formula C8H11NO. It consists of a phenol (benzene ring with a hydroxyl group, –OH) substituted at the 3-position by a dimethylamino group (–N(CH3)2). This structure combines both acidic and basic functionalities, making it an important intermediate in organic synthesis and industrial applications.

The compound is typically synthesized by nitration of phenol followed by reduction and subsequent dimethylation of the resulting aminophenol. Its physical form is usually a solid or oily liquid, with solubility in polar organic solvents due to the polar hydroxyl and amino groups.

3-Dimethylaminophenol has been extensively used in the preparation of dyes, photographic developers, and as an intermediate in the synthesis of pharmaceuticals and agrochemicals. The electron-donating dimethylamino group activates the aromatic ring toward electrophilic substitution, facilitating various functionalization reactions. The phenolic hydroxyl group can also participate in hydrogen bonding and influence the compound’s reactivity.

In medicinal chemistry, derivatives of 3-dimethylaminophenol have been explored for antioxidant properties, due to their ability to donate hydrogen atoms from the phenol group, neutralizing free radicals. It has also been utilized in the synthesis of local anesthetics and antiseptics.

The compound's chemical reactivity includes oxidation to quinone-type structures, alkylation or acylation at the amino group, and formation of azo dyes through coupling reactions with diazonium salts. These reactions underpin its application in dye chemistry and materials science.

Safety considerations for 3-dimethylaminophenol include its potential toxicity and irritant effects. It should be handled with appropriate protective equipment to avoid skin contact and inhalation.

In summary, 3-dimethylaminophenol is a versatile aromatic compound used mainly in dye manufacturing, pharmaceutical synthesis, and as an antioxidant agent. Its combined hydroxyl and dimethylamino substituents confer distinctive chemical reactivity valuable in various industrial and research contexts.

References

2024. 7-Dimethylamino-4-Hydroxycoumarin and Derivatives: Enhanced β-Chain Hydrogen-Bonding. Journal of Chemical Crystallography, 54(3).
DOI: 10.1007/s10870-024-01020-7

2023. Synthesis of positional isomer and analogues of neostigmine methylsulfate: an anticholinesterase agent. Chemical Papers, 77(11).
DOI: 10.1007/s11696-023-02891-4

2011. Silver Triflate Catalyzed Acetylation of Alcohols, Thiols, Phenols, and Amines. Synthesis, 2011(14).
DOI: 10.1055/s-0030-1259999
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