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2-Bromo-4′-methylpropiophenone

Organic Synthesisα-BrominationRegioselectivity

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

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Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

Buy 2-bromo-4-methylpropiophenone Cas 1451-82-7

⚠ Attention: For research use only. Not for human or veterinary use.
Molecular FormulaC10H11BrO
Molecular Weight227.10 g/mol
CAS No.1451-82-7
Cat. No.B029744
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Technical Parameters


Basic Identity
Product Name 2-Bromo-4′-methylpropiophenone
CAS 1451-82-7
Synonyms
2-Bromo-1-(4-methylphenyl)-1-propanone, 4-Methylphenyl 1-Bromoethyl Ketone
Molecular Formula C10H11BrO
Molecular Weight 227.10 g/mol
Structural Identifiers
SMILES CC1=CC=C(C=C1)C(=O)C(C)Br
InChI InChI=1S/C10H11BrO/c1-7-3-5-9(6-4-7)10(12)8(2)11/h3-6,8H,1-2H3
InChIKey OZLUPIIIHOOPNQ-UHFFFAOYSA-N
Commercial & Availability
Standard Pack Sizes 5 mg / 1 g / 5 g / 25 g / Bulk Custom
Availability In Stock
Custom Synthesis Available on request

2-Bromo-4′-methylpropiophenone: Key Intermediate Overview


2-Bromo-4′-methylpropiophenone (CAS 1451-82-7) is an aromatic ketone belonging to the α-bromoketone class, characterized by a bromine atom at the α-position and a 4-methyl substituent on the phenyl ring [1]. It is an off-white to white crystalline solid with a molecular weight of 227.10 g/mol and is soluble in chloroform and methanol . This compound serves as a versatile electrophilic building block in organic synthesis, enabling nucleophilic substitution and cross-coupling reactions .

Workflow
α-Bromoketone electrophilic building block for nucleophilic substitution and cross-coupling reactions.
Format
Off-white crystalline solid simplifies weighing, handling, and storage in multi-step syntheses.
Use Context
Supports synthesis of β-amino ketones, heterocyclic scaffolds, and certified reference standards for forensic analysis.

Why 2-Bromo-4′-methylpropiophenone Cannot Be Directly Substituted


The specific combination of an α-bromo substituent and a 4-methyl group on the phenyl ring dictates both the reactivity and the final product profile. Direct substitution with a non-brominated analog like 4′-methylpropiophenone would entirely preclude nucleophilic substitution at the α-position, drastically altering the synthetic pathway . Furthermore, changing the halogen from bromine to chlorine (as in 2-chloro-4′-methylpropiophenone) significantly reduces electrophilicity and can necessitate harsher reaction conditions or different catalysts, impacting yield and selectivity . Even altering the methyl group’s position or identity changes the electronic environment of the aromatic ring, affecting the rate and regioselectivity of subsequent reactions [1].

Replacing with non-brominated 4′-methylpropiophenone removes the α-bromo electrophilic site, preventing key nucleophilic substitutions.
Substituting 2-chloro-4′-methylpropiophenone alters electrophilicity; reaction conditions and catalyst requirements may shift, impacting yield and selectivity.
Changing the methyl group position or identity modifies the ring electronic environment, which can alter reaction rate and regioselectivity of subsequent steps.

2-Bromo-4′-methylpropiophenone: Performance vs. Structural Analogs


α-Bromination Yield and Selectivity Advantage

In a study on the regioselective α-bromination of aralkyl ketones, 4′-methylacetophenone (1e) achieved an α-bromination yield of 90% with 90% selectivity for the α-position over other potential bromination sites [1]. This performance surpasses that of unsubstituted acetophenone (89% yield, 89% selectivity) and significantly outperforms other substituted analogs like 4′-methoxy (72% yield, 72% selectivity) and 4′-cyano (73% yield, 73% selectivity) derivatives under identical conditions [1]. This demonstrates that the 4-methyl substituent provides an optimal electronic effect for efficient and selective α-bromination.

α-Bromination Yield & Selectivity
Reported
Target: 90% yield, 90% α-selectivity. Comparators: unsubstituted acetophenone (89%, 89%), 4′-methoxy (72%, 72%), 4′-cyano (73%, 73%) under identical conditions.
Supports compound-specific α-bromination efficiency for process selection.
Cross-study comparable data; verify under target conditions.
Organic Synthesisα-BrominationRegioselectivity

Synthesis Yield: Comparison of Bromination Methods

The synthesis of 2-bromo-4′-methylpropiophenone is reported with an isolated yield of 60.6% using a specific bromination protocol with 4′-methylpropiophenone [1]. An alternative method reports a yield range of 70-80% after aqueous workup [2]. In contrast, the synthesis of a closely related analog, m-chloro-α-bromopropiophenone, achieves a notably higher 96.1% yield under optimized conditions [3]. This 15.5-35.5 percentage point difference underscores the significant impact of the aromatic substituent (methyl vs. chloro) on reaction efficiency and highlights the need for precise, compound-specific protocols.

Synthesis Yield Comparison
Reported
Target: 60.6% (Method A), 70–80% (Method B). Comparator: m-chloro-α-bromopropiophenone 96.1%.
Yield context for cost modeling; method-specific optimization may be required.
Compound-specific protocol review recommended.
Process Chemistryα-Bromoketone SynthesisMethod Optimization

α-Bromination Regioselectivity: 4′-Methyl vs. Other Substituents

The data in Table 3 [1] clearly show that the 4′-methyl group directs α-bromination with high regioselectivity (90%), which is superior to that observed with strong electron-donating (4′-methoxy, 72%) or electron-withdrawing (4′-cyano, 73%) groups. This indicates an optimal electronic environment that favors the desired α-bromoketone product while minimizing ring bromination and other side products.

α-Regioselectivity Comparison
Reported
Target: 90% α-selectivity, 6% ring. Comparators: 4′-methoxy (72%, 19% ring), 4′-cyano (73%, 11% ring), 4′-nitro (49%, 16% ring).
4′-Methyl directs high α-bromination selectivity, minimizing side products.
Review electronic substituent effects.
Regioselective BrominationElectronic EffectsSubstituent Influence

Solid Form Advantage Over Liquid Precursor

2-Bromo-4′-methylpropiophenone is a solid at room temperature with a melting point of 75-82°C [REFS-1, REFS-2], while its precursor, 4′-methylpropiophenone, is a liquid with a melting point of 7.2°C . The solid state simplifies handling, weighing, and storage in an industrial or research setting, offering a logistical and practical advantage over liquid analogs that may require more complex containment or have higher volatility.

Solid Form vs. Liquid Precursor
Data to verify
Target: solid, mp 75–82 °C. Precursor 4′-methylpropiophenone: liquid, mp 7.2 °C.
Solid form may simplify handling and storage.
Verify lot-specific physical properties.
Physicochemical PropertiesHandling and StorageProcess Development

Reference Standard for Forensic Analysis

2-Bromo-4′-methylpropiophenone is an established analytical reference standard categorized as a precursor in the synthesis of cathinones . It is specifically used for the development and validation of presumptive color spot test methods for detecting piperazine analogues in seized illicit materials [1]. This certified application provides a defined, quality-controlled use case that is not shared by all structural analogs, making it a procurable standard for forensic and analytical method development.

Reference Standard Use
Class-level
Categorized as certified reference standard for cathinone synthesis; applied in spot test method development.
Supports forensic analytical method validation.
Class-level application; confirm standard certification.
Analytical ChemistryForensic ScienceReference Standards

2-Bromo-4′-methylpropiophenone: Key Applications


β-Amino Ketone Synthesis

The high electrophilicity of the α-bromo group makes this compound an ideal substrate for the synthesis of β-amino ketones, a class of compounds with potential biological activity. The efficient α-bromination selectivity of its precursor [1] directly supports this pathway. A documented application is its reaction with methylamine to form the β-amino ketone core of 4-methylmethcathinone .

Forensic Reference Standard

As a commercially available analytical reference standard, it is used to develop and validate methods for detecting synthetic cathinones and other controlled substance analogs [2]. Its role in a published method for the presumptive color spot test of piperazine analogues validates its utility in forensic science and regulatory compliance [2].

2-Bromo 4-methylpropiophenone

Synonyms: 4-Methylphenyl 1-Bromoethyl Ketone, 2-Bromo-1-(4-methylphenyl)-1-propanone

2-bromo-4-methylpropiophenon is an organic chemical compound with molecular formula C10H11BrO. The substance is considered as bromoketone, a brominated derivative of ketone. The CAS 1451-82-7.

The chemical is a white to yellow crystalline powder soluble in methanol and chloroform. The other properties of 2-bromo-4-methylpropiophenone include:

  • molecular weight: 227.101 g/mol,
  • melting point: 75 – 77°C,
  • boiling point: 273°C,
  • density: 1.357

The substance is mainly used as an intermediate in laboratory researches.

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Safe Handling and Storage

The compound is marked as irritant; therefore, must be handled only if wearing personal protective set. Any inhalation of fume, vapor, or dust should be carefully avoided. It is strongly recommended to work with the chemical outdoors or in well-ventilated areas.

2-bromo-4-methylpropiophenone must be kept in a tightly closed container. The storage facility should be well ventilated, and the temperature should not exceed 4°C.

What is 2-Bromo-4-Methylpropiophenone CAS 1451-82-7? How does it work?

2-Bromo-4′-methylpropiophenone, chemical formula C10H11BrO.

Properties: 2-Bromo-4′-methylpropiophenone is an organic compound that appears as a white crystalline powder. It has a distinctive odor and low toxicity. It is stable at room temperature but decomposes under high temperature or light conditions.

Uses: 2-Bromo-4′-methylpropiophenone has uses in the chemical and pharmaceutical industries. It is often used as an intermediate in the synthesis of other organic compounds, especially in the synthesis of amphetamines, which play an important role. In addition, it can be used in the synthesis of dyes, fragrances and rubber additives, etc.

Preparation: 2-Bromo-4′-methylpropiophenone can be prepared by reacting bromine with ethyl acetate. The intermediate of 2-Bromo-4′-methylpropiophenone is first obtained by reacting ethyl acetate with bromine, and then subsequent reaction and purification are carried out to obtain the final product.

SAFETY INFORMATION: The use of 2-bromo-4′-methylpropiophenone requires safety precautions. It is an irritant and contact with skin and eyes may cause inflammation. Inhalation of gases or dust should be avoided during use and it needs to be operated under well-ventilated conditions. Also, appropriate personal protective equipment such as gloves, goggles, and protective clothing should be worn. When stored, it should be kept in a dry, cool place away from sources of ignition and oxidizing agents.

Name: 2-bromo-4-methylpropiophenone
2-Bromo-4′-methylpropiophenone
2-Bromo-4-methyl propiophenone
2-Bromo-1-(4-methylphenyl)propan-1-one
2-Bromo-1-(4-methylphenyl)-1-propanone
CAS :1451-82-7
EINECS :1592732-453-0
Chemical formula :C10H11BrO
Molecular weight : 227.101
Density : 1.357
Melting point : 75-77 °C
Boiling point : 273 °C
Flash point : 59 °C
Storage conditions : Refrigerator

2-Bromo-4-Methyl Propiophenone CAS 1451-82-7 Price And Quantity

  • Price 4200 INR/Kilograms
  • Minimum Order Quantity 1 Kilograms

2-Bromo-4-Methyl Propiophenone CAS 1451-82-7 Trade Information

  • Payment Terms Cash Advance (CA)
  • Delivery Time 7 Days
  • Main Domestic Market All India

Product Description

We are occupied in bringing a large stock of  2-Bromo-4-Methyl Propiophenone CAS 1451-82-7. It is formulated with a premium quality of two mixture acids. This chemical is safe to use for a longer time. Apart from this, provided acid is cherished by our clients for its chemical properties. It has a great melting and boiling point.  2-Bromo-4-Methyl Propiophenone CAS 1451-82-7 is used in the laboratories and pharmaceutical industries. It can be customized in various packaging options as per the demands of consumers.

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