Bromoethane

Overview

A two-carbon primary halogenoalkane used to connect reaction pathways.

The polar C–Br bond makes carbon electrophilic; nucleophilic substitution replaces the leaving group, with selectivity and yield dependent on nucleophile and solvent.

Identifiers

Formula

C2H5Br

Functional group

Bromoalkanes

Molar mass

108.97 g/mol

Also known as

ETHYL BROMIDE, 1-Bromoethane, Ethane, bromo-, Bromic ether, Monobromoethane, Hydrobromic ether

Properties

Melting Point

-118.4 °C

Boiling Point

38.2 °C

Density

1.4604 g/cu cm at 20 °C

Water solubility

In water, 9,000 mg/L at 25 °C

Related compounds

• Bromoalkanes

  A two-carbon primary halogenoalkane used to connect reaction pathways.

Connected reactions

• Hydrolysis: Bromoethane → Ethanol

  Hydroxide attacks the saturated carbon bearing bromine while the C-Br bond breaks. This primary-substrate SN2 route replaces bromide with OH and preserves both carbon atoms; aqueous conditions favour this branch over elimination.

• Elimination: Bromoethane → Ethene

  The base removes a hydrogen from the carbon next to bromine. The C-H electrons form the C=C pi bond as bromide departs, so elimination removes H and Br without changing the two-carbon skeleton.

• Cyanide substitution: Bromoethane → Propanenitrile

  The carbon end of cyanide attacks the primary carbon of bromoethane as bromide leaves. The new C-C bond joins cyanide’s carbon to the original chain, giving a three-carbon nitrile rather than acetonitrile.

• Ammonia substitution: Bromoethane → Ethylamine

  Ammonia attacks the carbon bearing bromine to give an alkylammonium intermediate. A further ammonia molecule removes a proton to release ethylamine; the product can undergo additional alkylation if haloalkane remains.

References

1. PubChem Compound Summary: Bromoethane (CID 6332)National Center for Biotechnology Information · PubChem

   Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.

2. OpenStax Organic Chemistry: Characteristics of the SN2 reactionJohn McMurry · OpenStax · 2023

   Supports the qualitative structural interpretation of the recorded molecular structure; no new physical measurement or verified preparative yield is claimed.

3. Hazardous Substances Data Bank (HSDB): Bromoethane — melting pointHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6332#section=Melting-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Rumble J. (ed.). CRC Handbook of Chemistry and Physics. 99th ed. Cleveland: CRC Press Inc., 2018., p. 3-8

4. Hazardous Substances Data Bank (HSDB): Bromoethane — boiling pointHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6332#section=Boiling-Point. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Rumble J. (ed.). CRC Handbook of Chemistry and Physics. 99th ed. Cleveland: CRC Press Inc., 2018., p. 3-8

5. Hazardous Substances Data Bank (HSDB): Bromoethane — densityHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6332#section=Density. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Rumble J. (ed.). CRC Handbook of Chemistry and Physics. 99th ed. Cleveland: CRC Press Inc., 2018., p. 3-8

6. Hazardous Substances Data Bank (HSDB): Bromoethane — solubilityHazardous Substances Data Bank (HSDB)

   Retrieved through PubChem PUG View on 2026-09-08. https://pubchem.ncbi.nlm.nih.gov/compound/6332#section=Solubility. Source value, complete property clause or compact miscibility statement retained; absent pressure, temperature or phase conditions are not inferred. Original reference: Horvath AL; Halogenated Hydrocarbons. New York, NY: Marcel Dekker p. 610 (1999)