Bromobenzene

An aromatic organohalide, C6H5Br, 157.01 g/mol. Boiling point 313 °F at 760 mmHg, melting point -30.6 °C (SOLIDIFIES), as published. Appears in 6 documented reactions.

verified recordOrganic — aromatic organohalide7 measured properties6 documented reactions

Identifiers

Molecular formula: C₆H₅Br
Molecular weight: 157.01 g/mol
Exact mass: 155.957462 g/mol
IUPAC name: bromobenzene
SMILES: Brc1ccccc1
InChI: InChI=1S/C6H5Br/c7-6-4-2-1-3-5-6/h1-5H
InChIKey: QARVLSVVCXYDNA-UHFFFAOYSA-N

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Measured properties

Published measurements, each with its source. Two readings of one property are both shown, in the units each used.

Boiling Point: 313 °F at 760 mmHg (NTP, 1992)measured · CAMEO Chemicals; boiling point equals 313 °Fmeasured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
Melting Point: -24 °F (NTP, 1992)measured · CAMEO Chemicals; -30.6 °C (SOLIDIFIES)measured · Hazardous Substances Data Bank (HSDB)
Density: 1.49 at 77 °F (USCG, 1999) - Denser than water; will sinkmeasured · CAMEO Chemicals; @ 10 °C/4 °C: 1.5083; @ 15 °C/4 °C: 1.5017; @ 20 °C/4 °C: 1.4952; @ 30 °C/4 °C: 1.4815; @ 71 °C/4 °C: 1.426; @ 0 °C/4 °C: 1.5220measured · Hazardous Substances Data Bank (HSDB)
Solubility: less than 1 mg/mL at 68.9 °F (NTP, 1992)measured · CAMEO Chemicals; MISCIBLE WITH CHLOROFORM, BENZENE, PETROLEUM HYDROCARBONS; SOL IN ALCOHOL (10.4 G/100 G @ 25 °C), IN ETHER (71.3 G/100 G @ 25 °C); PRACTICALLY INOL IN WATER (0.045 G/100 G @ 30 °C)measured · Hazardous Substances Data Bank (HSDB)
Vapor Pressure: 5 mmHg at 82 °F ; 10 mmHg at 104 °F; 20 mmHg at 128.8 °F (NTP, 1992)measured · CAMEO Chemicals; 4.18 [mmHg]measured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
LogP: log Kow = 2.99measured · Hazardous Substances Data Bank (HSDB); 2.99measured · ILO-WHO International Chemical Safety Cards (ICSCs)
Flash Point: 123.8 °F (NTP, 1992)measured · CAMEO Chemicals; Flash point equals 124 °Fmeasured · Haz-Map, Information on Hazardous Chemicals and Occupational Diseases

Calculated properties

Derived from the structure, not from a sample; kept apart from the measurements above.

Molecular weight: 157.01 g/molcalculated · reference compound database; Average mass of one molecule, from reference compound database.
Exact mass: 155.95746 Dacalculated · reference compound database; Mass of the most common isotopic form.
XLogP3: 3calculated · reference compound database; Estimated oil/water partition, computed by reference compound database.
Polar surface area: 0 Å²calculated · reference compound database; Polar surface area as computed by reference compound database.
Complexity: 46calculated · reference compound database; A rough measure of how intricate the structure is.
H-bond donors: 0calculated · reference compound database
H-bond acceptors: 0calculated · reference compound database
logP: 2.4491calculated · chemistry engine; Estimated preference for oil over water. Higher means more oil-like.
Topological polar surface area: 0 Å²calculated · chemistry engine; Surface area from polar atoms; relates to how easily a molecule crosses membranes.
H-bond donors: 0calculated · chemistry engine; Atoms that can donate a hydrogen bond.
H-bond acceptors: 0calculated · chemistry engine; Atoms that can accept a hydrogen bond.
Rotatable bonds: 0calculated · chemistry engine; Single bonds the molecule can freely twist around.
Molar refractivity: 34.142 cm³/molcalculated · chemistry engine; Relates to the molecule's polarisability.
Fraction sp³ carbons: 0calculated · chemistry engine; Share of carbon atoms with tetrahedral bonding.
QED drug-likeness: 0.542calculated · chemistry engine; Quantitative estimate of drug-likeness (0–1).

What it is made of

Elements

Br Bromine1 atom · 50.9% by mass
C Carbon6 atoms · 45.9% by mass
H Hydrogen5 atoms · 3.2% by mass

Percentages are of the molecular weight above, worked out the same way the molar mass calculator does it.

Structure

Heavy atoms, hydrogen excluded: 7
Total atoms, hydrogen included: 12
Rings: 1
Aromatic rings: 1
Stereocentres: 0
Formal charge: 0

Functional groups

Halide (C–X)
A halogen atom attached to carbon.
Aromatic ring
A flat six-membered ring with delocalised electrons.

Matched by structural pattern, not by a measurement.

The molecule in three dimensions

Rotate and inspect the atoms. Loaded only when you ask, so the page stays light.

The drawing above is a diagram of what is bonded to what. A molecule is not flat, and the model here is one low-energy shape generated from the connectivity — useful for seeing which groups can reach each other, and not a measured structure. A real sample is a population of conformations, interconverting.

Reactions it appears in

6 documented reactions involve Bromobenzene, each with a written procedure and a source, and all of them are buchwald–hartwig amination. A few are shown.

Buchwald–Hartwig amination

Buchwald–Hartwig amination · as a reactant

A recorded experiment with its conditions, its yield where one was published, and a link to the source.

Buchwald–Hartwig amination

Buchwald–Hartwig amination · as a reactant

A recorded experiment with its conditions, its yield where one was published, and a link to the source.

Buchwald–Hartwig amination

Buchwald–Hartwig amination · as a reactant

A recorded experiment with its conditions, its yield where one was published, and a link to the source.

All 6 buchwald–hartwig amination records

Other names for it

The systematic name on this record is bromobenzene.

The sources also call it Monobromobenzene, Phenyl bromide, Benzene, bromo-, PhBr, BROMO-BENZENE.

Structurally related

Nothing structurally close to Bromobenzene has a page here yet.

Seen alongside it in reaction records

Molecules that appear in the same recorded reactions as Bromobenzene. This says nothing about structure: most of them are the bases, solvents, ligands and catalysts the chemistry needed, and they are here because somebody put them in the same flask.

1,4-Dioxane

used as a reactant

C₄H₈O₂, 88.106 g/mol.

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

C₃₉H₃₂OP₂, 578.632 g/mol.

1,2-Bis(diphenylphosphino)ethane

used as a reactant

C₂₆H₂₄P₂, 398.426 g/mol.

(1-Hydroxy-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzene

formed as a product

C₂₃H₃₆O, 328.54 g/mol.

(+/-)1-(2-Furyl)-1-(2-methoxyphenyl)ethanol

formed as a product

C₁₃H₁₄O₃, 218.252 g/mol.

1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

formed as a product

C₁₇H₂₅NO, 259.393 g/mol.

Where these values came from

reference compound database7961
compound record
chemistry engine
structure perception

compound record.

What this page does not claim

Identifiers are copied from the source record, measured values are reported as published, and calculated values are marked as calculated. Nothing here is a hazard, purity or handling assessment — how the library is checked.

Bromobenzene

Identifiers

Measured properties

Calculated properties

What it is made of

Elements

Structure

Functional groups

The molecule in three dimensions

Reactions it appears in

Buchwald–Hartwig amination

Buchwald–Hartwig amination

Buchwald–Hartwig amination

Other names for it

Structurally related

Seen alongside it in reaction records

1,4-Dioxane

1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

1,2-Bis(diphenylphosphino)ethane

(1-Hydroxy-4-(2-(trans-4-n-propylcyclohexyl)ethyl)cyclohexyl)benzene

(+/-)1-(2-Furyl)-1-(2-methoxyphenyl)ethanol

1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

Where these values came from

What this page does not claim

Where to next

More molecules under B

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