| | 1-Bromobutane Basic information |
| | 1-Bromobutane Chemical Properties |
| Melting point | -112 °C | | Boiling point | 100-104 °C(lit.) | | density | 1.276 g/mL at 25 °C(lit.) | | vapor density | 4.7 (vs air) | | vapor pressure | 150 mm Hg ( 50 °C) | | refractive index | n20/D 1.439(lit.) | | Fp | 23 °C | | storage temp. | Store below +30°C. | | solubility | 0.6g/l | | form | Liquid | | color | Clear colorless to light yellow | | Odor | characteristic odor | | explosive limit | 2.8-6.6%, 100°F | | Water Solubility | 0.608 g/L (30 ºC) | | Merck | 14,1553 | | BRN | 1098260 | | Stability: | Stable. Flammable - note low flash point. Incompatible with strong oxidizing agents, strong bases. | | InChIKey | MPPPKRYCTPRNTB-UHFFFAOYSA-N | | LogP | 2.75 | | CAS DataBase Reference | 109-65-9(CAS DataBase Reference) | | NIST Chemistry Reference | Butane, 1-bromo-(109-65-9) | | EPA Substance Registry System | 1-Bromobutane (109-65-9) |
| | 1-Bromobutane Usage And Synthesis |
| Chemical Properties | 1-bromobutane appears as a clear colorless to slightly yellow liquid with aroma. Flash point 65°F. Denser than water and insoluble in water, soluble in organic solvents such as alcohol, ether and chloroform.Vapors heavier than air. | | Uses | 1-Bromobutane is used as an intermediate in organic synthesis and as a solvent for cleaning and degreasing. It acts as an alkylating agent as well as to prepare organometallic compounds such as n-butyllithium. It is also involved in the synthesis of procaine and tetracaine. It reacts with magnesium metal to prepare the Grignard reagent, which is used to form carbon-carbon bonds. | | Application | 1-Bromobutane may be used as a derivatization reagent for multiple functional groups (amino, carboxyl, and phenolic hydroxyl groups) of amino acids to improve hydrophobicities and basicities of the amino acids. It may also be used as an internal standard for the quantification of 1- and 2-bromopropane in human urine by headspace gas chromatography. | | Synthesis Reference(s) | Journal of the American Chemical Society, 86, p. 964, 1964 DOI: 10.1021/ja01059a073
Organic Syntheses, Coll. Vol. 1, p. 25, 1941
Synthesis, p. 326, 1982 | | General Description | 1-Bromobutane, an alkyl halide, is an alkylating agent. Its rotational constants, nuclear quadrupole constants and centrifugal distortion constants have been stated based on microwave spectral data. The rate coefficient for the reaction of 1-bromobutane with hydrogen atoms has been reported to be 2.4±1.2x1010cm3mol-1s-1. | | Air & Water Reactions | Highly flammable. Insoluble in water. | | Reactivity Profile | 1-Bromobutane is incompatible with strong bases and oxidizers [USCG, 1999]. | | Hazard | Flammable, dangerous fire risk.
| | Health Hazard | Irritating to the eyes, nose, throat, and upper respiratory tract. Symptoms of exposure include burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, nausea, and vomiting. Irritating to the skin. | | Safety Profile | Moderately toxic by
intraperitoneal route. Mddly toxic by
inhalation. Dangerous fire hazard when
exposed to heat, flame, or oxidizers. Violent
reaction with bromobenzene + sodium
above 30℃. Can react with oxidizing
materials. To fight fire, use CO2, dry
chemical, mist or spray. See also
BROMIDES. | | Synthesis | 1-bromobutane is a primary alkyl halide (primary alkyl) and therefore it is produced from bimolecular nucleophilic substitution reactions (Sn2).
The preparation method of 1-bromobutane is as follows: stirring n-butanol, sodium bromide, water and sulfuric acid evenly, heating under reflux for 3 hours, steaming out the crude bromobutane, washing with water, treating with cold concentrated sulfuric acid, and distilling to obtain the finished product.
Reaction equation: CH3CH2CH2CH2OH+NaBr+H2SO4→CH3CH2CH2CH2Br+Na2SO4+H2O
This halide is easily prepared by reacting butan-1-ol (primary alcohol) with sodium bromide solution and excess of concentrated sulfuric acid. The reaction between sodium bromide and sulphuric acid origins hydrobromic acid. | | Shipping | UN1126 & UN23391- & 2-Bromobutane,
Hazard Class: 3; Labels: 3—Flammable liquid. | | Purification Methods | Wash the bromide with conc H2SO4, water, 10% Na2CO3 and again with H2O. Dry it over CaCl2, CaSO4 or K2CO3, and distil it. Redistil it after drying with P2O5, or pass it through two columns containing 5:1 silica gel/Celite mixture and store it with freshly activated alumina. [Beilstein 1 IV 258.] | | Incompatibilities | Vapor may form explosive mixture with
air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep
away from alkaline materials, strong bases, strong acids,
oxoacids, epoxides. May accumulate static electrical
charges and cause ignition of its vapors. | | Waste Disposal | Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal,
state, and local environmental regulations must be observed |
| | 1-Bromobutane Preparation Products And Raw materials |
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