Methyl 7‑bromoheptanoate CAS 54049‑24‑0

Product Overview

Methyl 7‑bromoheptanoate is a typical bifunctional aliphatic ester intermediate with linear seven‑carbon chain structure. One terminal carries active bromine leaving group and the other end is methyl‑ester group.
Two functional groups can undergo independent chemical transformation. This characteristic makes it widely applied for constructing long‑carbon‑chain fragments in medicinal‑chemistry, especially for PROTAC linkers, drug‑molecule side‑chains and isotope‑labeled pharmaceutical intermediates. It is a commonly‑used laboratory fine‑chemical raw material for academic research and early‑stage drug‑development projects.

Basic Product Information

1. Product Name: Methyl 7‑bromoheptanoate
2. CAS NO.: 54049‑24‑0
3. Synonym: 7‑Bromoheptanoic acid methyl ester
4. Molecular Formula: C₈H₁₅BrO₂
5. Molecular Weight: 223.11
6. Structural formula:
7. Purity: ≥98%
8. Appearance: Colorless to pale‑yellow transparent liquid
9. Density: 1.257 g/cm³ (25℃)
10. Boiling point: 112℃ /5 Torr; 229.2℃ /760 mmHg
11. Refractive index: n₂₀/D 1.461
12. Flash Point: 118.2℃
13. Solubility: Miscible with dichloromethane, THF, ethyl acetate; insoluble in water
14. HS Code: 2915900090
15. MDL Number: MFCD02258672

Frequently Asked Questions (FAQ)

Question 1: What core advantage distinguishes Methyl 7‑bromoheptanoate from other bromo‑alkyl ester intermediates?
Answer: It provides fixed seven‑carbon linear spacer. The bromo‑terminal can do nucleophilic substitution meanwhile methyl‑ester group can be hydrolyzed or reduced. Two functional groups can be modified step‑by‑step without mutual interference. Chemists can precisely introduce this uniform long‑chain fragment into target molecules without multi‑step carbon‑chain extension.

Question 2: What risks should we pay attention to during laboratory handling?
Answer: This substance belongs to irritant chemical. It may irritate skin, eyes and respiratory mucosa when liquid splashes or volatile mist is inhaled. Operators shall wear chemical‑resistant gloves, goggles and fume‑hood operation. Avoid contacting with strong bases; excessive alkaline condition will trigger ester hydrolysis and elimination side‑reaction to generate alkene impurities.

Question 3: Which synthetic routes are available for this compound, and which one fits lab preparation?
Answer: The mainstream lab route is esterification of 7‑bromoheptanoic acid with methanol under acid catalysis, with simple operation and moderate yield. Alternative approach is bromination of methyl 7‑hydroxyheptanoate. The second route avoids free carboxylic‑acid raw‑material, yet brominating reagent is corrosive. For small‑batch lab work, acid‑catalyzed esterification is more preferred.

Question 4: How does storage condition affect product quality over time?
Answer: Under long‑term room‑temperature storage, trace elimination degradation may slowly occur and produce alkenyl‑ester impurities. Tightly sealed and shaded dry environment is required. Avoid frequent opening of container. It is not mandatory for cold storage, but 2‑8℃ refrigeration can effectively extend shelf‑life and suppress impurity growth.

Question 5: What kind of downstream transformation can be achieved via its bromine and ester sites?
Answer: Terminal bromine participates in SN2 substitution with amine, phenol and other nucleophiles to build C‑N / C‑O linkage. Methyl ester can be hydrolyzed into carboxylic acid, reduced to alcohol, or converted into amide. Two reactive sites support divergent synthesis: users can modify bromine first and then transform ester group, or reverse the operation sequence according to synthetic route design.

Application Cases

Application Case 1: Synthesis of alkyl‑chain PROTAC linker fragments
This reagent serves as key raw‑material for preparing aliphatic linkers of PROTAC molecules. After nucleophilic substitution of bromine atom with target‑protein‑ligand fragment, methyl‑ester is hydrolyzed to carboxyl group for further connecting E3‑ligand moiety. The 7‑carbon linear spacer adjusts molecular flexibility and spatial distance between two ligands, which is critical to maintain protein‑degradation activity. This route is widely adopted in early‑stage PROTAC screening work.

Application Case 2: Preparation of isotope‑labeled tianeptine pharmaceutical intermediates
It is applied for synthesizing isotope‑labelled tianeptine reference substance. Derivatives prepared from deuterated methyl‑7‑bromoheptanoate can be used as internal standard for quantitative LC‑MS drug‑detection. The long alkyl‑ester skeleton matches tianeptine side‑chain structure, providing reliable tool for pharmacokinetic and bio‑analytical research.

Application Case 3: Construction of long‑chain fragments for central‑nervous‑system drug candidates
Many neuro‑active drug molecules require flexible long‑alkyl side‑chains. Methyl 7‑bromoheptanoate introduces seven‑carbon aliphatic segment through substitution reaction. After ester‑group conversion, it can build amide‑type candidate compounds for anti‑depressant and anti‑ulcer molecule screening, helping adjust compound lipophilicity and blood‑brain‑barrier penetration property.

Application Case 4: Building blocks for bio‑imaging fluorescent‑probe synthesis
The bifunctional structure is used for assembling small‑molecule fluorescent probes for biological imaging. Bromine end couples with fluorophore; methyl‑ester site can be hydrolyzed into carboxyl group for bioconjugation with peptide or protein. The linear alkyl‑chain adjusts probe’s hydrophilic‑lipophilic balance, improving cell‑membrane permeability of imaging agents.

Application Case 5: Exploratory research of functional polymer monomer
In material‑chemistry exploratory study, it acts as modified monomer precursor. After substituting bromine with special functional groups, it participates in poly‑ester or poly‑urethane synthesis. The bromine element can endow partial flame‑retardant property to polymer materials. Most relevant works stay at laboratory‑formula exploration stage, rather than large‑scale industrial‑monomer production.

Safety and Storage

1. Keep containers tightly sealed, store in cool, dry, shaded and well‑ventilated cabinet. Recommended storage temperature: 2‑8℃ for long‑term preservation; room‑temperature short‑term storage is acceptable.
2. Keep away from strong alkali, strong oxidizing agents. Prevent moisture from entering package.
3. Avoid inhalation of vapors, skin and eye contact. Operate inside fume hood.
4. Not classified as dangerous goods for transportation, but prevent package breakage and liquid leakage during transit. Keep away from direct sunlight and high‑temperature environment.

Product Manager Information

Product Manager: Emma Song
Email: emma@coreychem.com