PRODUCT IDENTIFICATION
TOXICITY
SMILES
ClCCCC
CLASSIFICATION
Organohalide
EXTRA NOTES
PHYSICAL AND CHEMICAL PROPERTIES
78 - 79 C
REFRACTIVE INDEX
1.4018
-6 C
USA.gov - n-Butyl chloride
Wikipedia Linking - 1-Chlorobutane
Google Scholar Search - n-Butyl chloride
U.S. National Library of Medicine - n-Butyl chloride
PubChem Compound Summary - n-Butyl chloride
KEGG (Kyoto Encyclopedia of Genes and Genomes) - n-Butyl chloride
ChEBI (http://www.ebi.ac.uk/chebi/) - n-Butyl chloride
NCBI (http://www.ncbi.nlm.nih.gov/) - n-Butyl chloride
Material Safety Data Sheet - n-Butyl chloride
EPA - Substance Registry Services - n-Butyl chloride
Local:
Halogenoalkanes, also known as haloalkanes or alkyl halides, are organic
compounds in which one or more hydrogen atoms in an alkane have been replaced by
halogen atoms, fluorine, chlorine, bromine or iodine. In carbon-halogen bond,
halogens have significantly greater electronegativities than carbon except
iodine. In result, this functional group is polarized so that the carbon is
electrophilic and the halogen is nucleophilic. Halogenoalkanes are can be
classified depending on the halogen atom position on the chain of carbon atoms.
The carbon which is attached with the halogen atom is linked up with only one
other alkyl group in primary halogenoalkanes, whereas directly linked up with
two and three other alkyl groups in secondary halogenoalkanes and tertiary
halogenoalkanes respectively. In some case, primary halogenoalkanes are counted
even though there are no alkyl groups attached to the carbon with the halogen on
it. Three characteristics provide important influences on the chemical behavior
of halogenoalkanes, these are electronegativity, covalent bond strength and the
relative stability of the corresponding halide anions. Fluoroalkanes have the
strongest of the carbon-halogen covalent bonds so that they are unreactive. This
is stronger single bond than a carbon-carbon bond. The carbon-chlorine covalent
bond is slightly weaker than a carbon-carbon bond, and the bonds to the other
halogens are weaker. The stability may be estimated from the relative acidities
of the H-X acids. All the hydrohalic acids are very strong, but with small
differences in the direction HCl < HBr < HI, with the exception of HF.
Halogenoarenes, also called haloarene, or aryl Halide, are an organic compound
in which one or more hydrogen atoms in an aromatic ring have been replaced by
halogen atoms. The Haloarenes exhibit many differences compare to haloalkanes in
the method of preparation and their chemical and phisical properties.
Haloalkanes are used in as refrigerants, solvents, blowing agents, aerosol
propellants, fire extinguishing media , and in semiconductor device fabrication.
One of big consumption of halogenoalkanes (properly speaking, halogenoalkenes)
is as a raw material to prepare plastics such as PVC [poly(chloroethene)] from
chloroethene and PTFE [poly(tetrafluoroethene)] from tetrafluoroethene.
Halogenoalkanes and halogenoarenes react with lots of compounds resulting in a
wide range of different target substances. They are useful intermediates in
making other organic compounds.
- Summary of substitution and elimination reaction based on alkyl group structure
| Alkyl Halides |
SN1 and E1 |
SN2 and E2 |
| Primary (RCH2X) | Neither SN1 nor E1 occur | both SN2 and E2
will occur (SN2 preferred. E2 preferred when sterically hindered base is used) |
| Secondary (R2CHX) | will
occur slowly in high dielectric ionizing solvents
( SN1 preferred) |
both SN2 and E2
will occur (SN2 preferred if base is weaker than acetate, pKa = 4.8, E2 preferred if base is strong) |
| Tertiary (R3CX) | both SN1 and E1
will occur (SN1 preferred) |
No SN2 will occur E2 will dominate if base is strong |
|
Allyl (H2C=CHCH2X) |
will occur slowly in high dielectric ionizing solvents | Rapid SN2 for primary and secondary halides but slow for tertiary. E2 when nucleophile is basic. |
|
Benzyl (C6H5CH2X) |
will occur slowly in high dielectric ionizing solvents | Rapid SN2 for primary and secondary halides but slow for tertiary. E2 when nucleophile is basic. |
- SN1 and SN2 reaction order based on alkyl group structure
- SN2 : CH3X (100%) > RCH2X > R2CHX > R3CX
- SN1 : CH3X < RCH2X < R2CHX < R3CX (100%)
- Nucleophilicity order
- F- < Cl- < Br- < I- In a protic solvent which decrease SN2 rate due to solvating nucleophile
- F- > Cl- > Br- > I- In a polar aprotic solvent which increase SN2 reaction due to no solvating nucleophile
- F- > Cl- > Br- > I- SN2 in the gas phase
- Leaving group Among halogens: I > Br > Cl > F
n-Butyl ChloridE (also called 1-Chlorobutane) is a clear, colorless , flammable liquid belonging to the family of organic halogen compounds. It is hard to dissolve in water, but can be mixed with alcohol and ether. This chemical is on the special health hazard substance list because it is flammable and gives off irritating or toxic fumes (or gases) in a fire. It is used as a solvent, as a medicine to control worms, for organometallic compound synthesis and to make other chemicals. n-Butyl chloride is used as an alkylating agent in organosynthesis, organometallic compounds manufacturing and as a solvent. n-Butyl chloride is also used as an antihelmintic in veterinary medicine.
APPEARANCE
99.0% min
0.1% max
0.25% max ( as Dibutyl Ether)
BOILING POINT
77 - 79 C
HAZARD OVERVIEW
GHS (Globally Harmonised System) Classification: Flammable liquids. Acute toxicity (Oral). Hazard statements: Highly flammable liquid and vapour. May be harmful if swallowed.
GHS
Danger
PICTOGRAMS
HAZARD STATEMENTS
H225-H303
P STATEMENTS
P210
RISK PHRASES
11
SAFETY PHRASES
9-16-29
PRICE INFORMATION