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Acetone Cyanohydrin

Also known as 2-hydroxy-2-methylpropanenitrile, Acetone cyanhydrin, 2-Hydroxyisobutyronitrile, 2-Methyllactonitrile

Acetone Cyanohydrin, also known as 2-hydroxy-2-methylpropanenitrile, is a specialized nitrile intermediate with formula C4H7NO and molecular weight 85.10.

Organic chemical intermediates Nitrile intermediates
C₄H₇NO
C₄H₇NO

Product identity

CAS number
75-86-5
Molecular formula
C4H7NO
Molecular weight
85.10 g/mol
Category
Organic chemical intermediates
Subcategory
Nitrile intermediates
Common aliases
2-hydroxy-2-methylpropanenitrile, Acetone cyanhydrin, 2-Hydroxyisobutyronitrile

Product overview

What is Acetone Cyanohydrin?

Acetone Cyanohydrin is an organic nitrile compound identified by CAS number 75-86-5 and IUPAC name 2-hydroxy-2-methylpropanenitrile. Its molecular formula is C4H7NO, and its stated molecular weight is 85.10. Other recognized names include Acetone cyanhydrin, 2-Hydroxyisobutyronitrile, 2-Methyllactonitrile, and 2-Cyano-2-propanol. The molecule combines a nitrile group with a tertiary alcohol function on the same carbon framework.

Acetone Cyanohydrin contains a carbon–nitrogen triple bond and a hydroxyl-bearing tertiary carbon, giving it reactivity distinct from acetone and from simpler nitriles. The nitrile group can participate in transformations that introduce nitrogen-containing functionality, while the adjacent hydroxyl group influences polarity and reaction behaviour. Its response to heat, acids, bases, nucleophiles, and formulation conditions requires careful assessment because cyanohydrin chemistry can involve decomposition pathways.

The established context for Acetone Cyanohydrin is specialty chemical synthesis, particularly as a precursor used to build more complex organic intermediates. Its structure supports routes toward compounds containing nitrile-derived, amide-related, or other nitrogen-functional architectures, depending on the reaction system. Such uses are process-specific: suitability depends on the intended transformation, catalyst or reagent combination, concentration, temperature profile, and applicable handling controls.

Selection of Acetone Cyanohydrin should therefore focus on the exact synthetic objective and the process chemistry rather than on name recognition alone. Buyers and formulators should compare the required reaction pathway with the behaviour of alternative nitrile or cyanohydrin intermediates, then evaluate compatibility with equipment and operating conditions. A product-specific technical and safety assessment remains important before laboratory, pilot, or manufacturing use. For commercial selection, the compound name should be considered separately from the specification and supplied form required for the intended process.

Technical profile

Product properties

Review the product identity and general physical profile before specifying the grade required for your operation.

IUPAC name
2-hydroxy-2-methylpropanenitrile
Category
Organic chemical intermediates
Subcategory
Nitrile intermediates
Molecular formula
C4H7NO
Molecular weight
85.10 g/mol

Uses and markets

Applications and industries

The correct product specification depends on the intended process, grade requirements and operating conditions.

Detailed product information

Detailed Acetone Cyanohydrin product information

Molecular structure and reactive functionality

Acetone Cyanohydrin is a compact cyanohydrin in which a nitrile group and tertiary hydroxyl group are attached to the same carbon framework. This arrangement distinguishes it from acetone, which contains a carbonyl group, and from acetonitrile, which lacks the hydroxyl-bearing tertiary center. The combined functionality makes Acetone Cyanohydrin useful for designing transformations that retain, modify, or replace nitrile-derived reactivity. Chemical behaviour should be assessed under the specific reaction conditions used.

The nitrile carbon can serve as a synthetic entry point for nitrogen-containing products, while the hydroxyl group affects polarity, hydrogen bonding, and susceptibility to acid- or base-mediated changes. Acetone Cyanohydrin therefore cannot be treated as an inert solvent or general-purpose diluent. Reaction design should consider possible decomposition, competing pathways, reagent compatibility, and temperature exposure. Mechanistic assumptions based only on the presence of a nitrile group may be incomplete.

Reactivity in organic synthesis

In organic synthesis, Acetone Cyanohydrin can function as a building block when a route requires the combination of a nitrile-derived carbon with a substituted alcohol centre. Transformations may be planned around the nitrile group, the hydroxyl group, or sequential use of both functions. The practical outcome depends on catalysts, solvents, water content, concentration, and thermal profile, so a literature reaction should not automatically be treated as a universal manufacturing recipe.

Compared with acetonitrile, Acetone Cyanohydrin offers an additional hydroxyl-bearing tertiary carbon and a more highly substituted framework. Compared with acetone, it provides nitrile functionality but lacks the ordinary ketone carbonyl of acetone. These structural differences change reaction selection and expected product classes. Chemists evaluating Acetone Cyanohydrin should define the desired bond changes first, then test selectivity and conversion under appropriately controlled development conditions.

Process behaviour and analytical considerations

Analytical work on Acetone Cyanohydrin commonly begins by confirming identity through complementary techniques appropriate to nitrile-containing organic compounds. Infrared analysis can help examine functional-group features, while nuclear magnetic resonance and chromatographic methods can support structural and compositional assessment. The selected method should distinguish Acetone Cyanohydrin from residual acetone, related nitriles, decomposition products, solvent signals, and other process-specific impurities rather than relying on a single response.

Acetone Cyanohydrin may be particularly sensitive to the relationship between composition, temperature, acidity, basicity, and residence time. Analytical sampling plans should therefore minimise changes between collection and measurement, especially when the material is being studied in reactive mixtures. Results are most useful when the method, sample preparation, and reference comparison are suited to the intended synthesis. A method developed for another nitrile may require revalidation for this compound.

Selecting Acetone Cyanohydrin for synthesis routes

Selection decisions for Acetone Cyanohydrin should start with the target molecule, the planned reaction mechanism, and the functional groups that must survive each step. Its value is greatest where the nitrile and tertiary hydroxyl arrangement provides a direct or adaptable route to the desired intermediate. If only a simple nitrile or ketone function is needed, a different compound may offer a more straightforward reaction profile and fewer competing pathways.

Acetone Cyanohydrin should also be compared with structurally related cyanohydrins and nitriles on the basis of substitution, polarity, transformation options, and behaviour under the proposed process conditions. A particular grade’s suitability cannot be inferred solely from the chemical name. Route trials, analytical monitoring, equipment compatibility review, and product-specific safety assessment help determine whether Acetone Cyanohydrin fits laboratory, pilot, or production chemistry.

Frequently asked questions

Questions about Acetone Cyanohydrin

What is Acetone Cyanohydrin used for in chemical synthesis?

Acetone Cyanohydrin is principally used as a specialized organic intermediate. Its structure combines a nitrile group with a tertiary hydroxyl group, allowing chemists to plan transformations that produce more complex nitrogen-containing molecules or related functional architectures. The exact application depends on the reaction sequence, reagents, catalyst system, solvent, temperature, and desired downstream product. It is not a universal substitute for acetone, acetonitrile, or another cyanohydrin. A route that appears suitable in a laboratory reference may require separate development before scale-up. Users should evaluate reaction selectivity, possible decomposition, analytical control, equipment compatibility, and applicable safety requirements for the intended process.

How does Acetone Cyanohydrin differ from acetone?

Acetone and Acetone Cyanohydrin have different functional groups and therefore behave differently in synthesis. Acetone contains a ketone carbonyl group, whereas Acetone Cyanohydrin contains a nitrile group and a hydroxyl group attached to the same substituted carbon framework. The cyanohydrin can provide access to nitrile-derived transformations that acetone cannot provide directly. Conversely, reactions designed for acetone’s carbonyl chemistry should not be assumed to work with Acetone Cyanohydrin. Differences in polarity, hydrogen bonding, reaction pathways, and stability under process conditions can affect solvent choice, catalyst selection, selectivity, and analytical interpretation.

How does Acetone Cyanohydrin compare with acetonitrile?

Acetonitrile is a small nitrile solvent with the formula CH3CN, while Acetone Cyanohydrin is a substituted cyanohydrin containing both nitrile and hydroxyl functionality. Acetone Cyanohydrin therefore offers a more complex carbon skeleton and a second reactive or interaction site that acetonitrile does not possess. The two compounds should not be treated as interchangeable solvents or synthetic equivalents. Acetonitrile is often selected for solvent properties, whereas Acetone Cyanohydrin is generally considered for its role as a functionalized intermediate. Reaction planning should compare the required molecular fragment, expected transformation, compatibility, and process behaviour rather than focusing only on the shared nitrile group.

What chemical features control Acetone Cyanohydrin reactivity?

The principal features are the nitrile group, the tertiary hydroxyl group, and the substituted carbon framework connecting them. The nitrile can undergo transformations that introduce or reveal nitrogen-containing functionality, while the hydroxyl group affects hydrogen bonding, polarity, and interactions with acids, bases, catalysts, and other reagents. The tertiary arrangement also influences steric accessibility and the range of possible reaction pathways. Temperature, water content, residence time, concentration, and the surrounding chemical environment can alter observed behaviour. For that reason, Acetone Cyanohydrin should be evaluated in the complete reaction system, not by considering one functional group in isolation.

Which analytical methods can help identify Acetone Cyanohydrin?

Identification and composition assessment can use complementary analytical methods selected for the sample matrix and intended decision. Infrared spectroscopy can provide evidence for characteristic functional-group features, while nuclear magnetic resonance can help confirm the carbon and hydrogen environment. Chromatographic methods may separate Acetone Cyanohydrin from residual acetone, solvents, related nitriles, and process-derived impurities. The appropriate detector, sample preparation, calibration approach, and reference materials depend on the laboratory method. Because reactive samples may change during collection or preparation, analysts should consider timing, temperature, container compatibility, and matrix effects. A method used for another nitrile may need compound-specific suitability work.

What should be considered before using Acetone Cyanohydrin in a process?

Before use, the process team should define the intended reaction, expected products, operating range, and potential decomposition or side-reaction pathways. Acetone Cyanohydrin should be assessed for compatibility with the selected reagents, solvent system, catalysts, equipment materials, sampling method, and waste-treatment approach. The chemical’s nitrile and hydroxyl functionality may respond differently from those of a related compound, so substitution assumptions require evidence from route development. Personnel should consult the current product-specific safety information and applicable local requirements, establish suitable engineering and emergency controls, and confirm analytical methods before advancing from small-scale experiments to larger operations.

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