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2-Chloro-3',4'-dihydroxyacetophenone
[CAS 99-40-1]

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Identification
ClassificationBiochemical >> Carbohydrate >> Double sugar
Name2-Chloro-3',4'-dihydroxyacetophenone
Synonyms4-(Chloroacetyl)catechol
Molecular Structure2-Chloro-3',4'-dihydroxyacetophenone molecular structure (CAS 99-40-1)
Molecular FormulaC8H7ClO3
Molecular Weight186.59
CAS Registry Number99-40-1
EC Number202-754-8
SMILESC1=CC(=C(C=C1C(=O)CCl)O)O
Properties
Density1.4±0.1 g/cm3 Calc.*
Melting point174 - 176 °C (Expl.)
Boiling point418.7±35.0 °C 760 mmHg (Calc.)*
Flash point207.0±25.9 °C (Calc.)*
Index of refraction1.612 (Calc.)*
*Calculated using Advanced Chemistry Development (ACD/Labs) Software.
Safety Data
Hazard Symbolssymbol symbol   GHS06;GHS07 Danger  Details
Risk StatementsH301-H315-H319-H335-H412  Details
Safety StatementsP261-P264-P264+P265-P270-P271-P273-P280-P301+P316-P302+P352-P304+P340-P305+P351+P338-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501  Details
Hazard Classification
up    Details
HazardClassCategory CodeHazard Statement
Skin irritationSkin Irrit.2H315
Eye irritationEye Irrit.2H319
Specific target organ toxicity - single exposureSTOT SE3H335
Chronic hazardous to the aquatic environmentAquatic Chronic3H412
Acute toxicityAcute Tox.3H301
Eye irritationEye Irrit.2AH319
SDSAvailable
up chemBlink Chemical Story
2-Chloro-3',4'-dihydroxyacetophenone is systematically 2-chloro-1-(3,4-dihydroxyphenyl)ethanone. It combines a catechol ring with an alpha-chloroketone side chain. The pairing explains its synthetic value: two phenolic hydroxyl groups reproduce the 3,4-dihydroxy aromatic pattern familiar from catecholamine chemistry, while the chloromethyl ketone provides an electrophilic handle for nucleophilic substitution and heterocycle-forming sequences. Literature records reach back many decades, and modern reports prepare it from catechol and chloroacetyl chloride under Lewis-acid conditions. It appears as an intermediate in medicinal and heterocyclic chemistry rather than as a finished therapeutic agent. Public exact-CAS literature does not justify assigning one dominant commercial end use, so its most reliable story is functional-group chemistry and its role as a versatile building block.

The exact registry identity matters because free forms, salts, hydrates, stereoisomers, metabolites, intermediates and finished medicines can have separate CAS numbers even when their names are closely related. This distinction affects molecular weight, analytical standards, formulation, manufacturing specifications and interpretation of published data. A reliable database story therefore follows the exact substance rather than silently borrowing every property of a related compound.

Structure also shows how chemists use functional groups as deliberate tools. Aromatic and heterocyclic frameworks establish molecular shape and electronics, while amines, hydroxyl groups, carbonyls, carboxyl functions or ionic centers determine reactivity and intermolecular interactions. In multistep synthesis, a compound may be valuable precisely because one position can be transformed selectively while the rest of a complex framework survives.

Modern development is also an analytical-control problem. Researchers must establish identity and purity, distinguish relevant stereoisomers or salt forms, monitor process-related species and define reproducible specifications. These requirements explain why an intermediate, metabolite or reagent can be scientifically important even when it is never administered as an independent medicine.

A Chemical Story must distinguish documented use from structural possibility. A familiar scaffold may suggest an activity, but resemblance is not evidence that the exact CAS substance has been tested or approved for that purpose. Verified history and demonstrated applications therefore take priority over attractive but unsupported extrapolation.

Seen broadly, practical performance emerges from the entire molecular system rather than one recognizable group. Structure, stereochemistry, physical form, synthetic route, metabolism and reaction environment can all determine what a substance actually does. Connecting those molecular details to its documented role is what turns a registry entry into a meaningful chemical story.

The exact registry identity matters because free forms, salts, hydrates, stereoisomers, metabolites, intermediates and finished medicines can have separate CAS numbers even when their names are closely related. This distinction affects molecular weight, analytical standards, formulation, manufacturing specifications and interpretation of published data. A reliable database story therefore follows the exact substance rather than silently borrowing every property of a related compound.

Structure also shows how chemists use functional groups as deliberate tools. Aromatic and heterocyclic frameworks establish molecular shape and electronics, while amines, hydroxyl groups, carbonyls, carboxyl functions or ionic centers determine reactivity and intermolecular interactions. In multistep synthesis, a compound may be valuable precisely because one position can be transformed selectively while the rest of a complex framework survives.

Modern development is also an analytical-control problem. Researchers must establish identity and purity, distinguish relevant stereoisomers or salt forms, monitor process-related species and define reproducible specifications. These requirements explain why an intermediate, metabolite or reagent can be scientifically important even when it is never administered as an independent medicine.

References:
1. PubChem. 2-Chloro-3',4'-dihydroxyacetophenone, CID 66834.
2. Journal of the American Chemical Society literature record for CAS 99-40-1, 1935.
3. European Journal of Medicinal Chemistry. 2014;82:293-307.

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