tert-Butylamine

tert-Butylamine Basic information
Product Name:tert-Butylamine
Synonyms:tert-Butylamine purified by redistillation, >=99.5%;t-Butylamine 〔2-Amino-2-methylpropane〕;1,1-dimethylethanamine;2-Methyl-2-aminopropane;2-methyl-2-propanamin;2-Methyl-2-propanamine;2-Propanamine,2-methyl-;2-AMINOISOBUTANE
CAS:75-64-9
MF:C4H11N
MW:73.14
EINECS:200-888-1
Product Categories:Amines;Building Blocks;C2 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks;75-64-9;K00001
Mol File:75-64-9.mol
tert-Butylamine Structure
tert-Butylamine Chemical Properties
Melting point -67 °C (lit.)
Boiling point 46 °C (lit.)
density 0.696 g/mL at 25 °C (lit.)
vapor density 2.5 (vs air)
vapor pressure 5.7 psi ( 20 °C)
refractive index n20/D 1.377(lit.)
Fp −36.4 °F
storage temp. Store below +30°C.
solubility water: miscible1000g/L at 25°C
form Liquid
pka10.68(at 25℃)
color Clear
PH12 (100g/l, H2O, 20℃)
OdorLike ammonia.
Odor Threshold0.17ppm
explosive limit1.5-9.2%(V)
Water Solubility MISCIBLE
Sensitive Air Sensitive
Merck 14,1545
BRN 605267
Stability:Stable. Incompatible with strong acids, strong oxidizing agents. Highly flammable.
CAS DataBase Reference75-64-9(CAS DataBase Reference)
NIST Chemistry Reference2-Propanamine, 2-methyl-(75-64-9)
EPA Substance Registry Systemtert-Butylamine (75-64-9)
Safety Information
Hazard Codes F,C,T
Risk Statements 11-20/22-35-25-20-52/53
Safety Statements 16-26-36/37/39-45-28A-61
RIDADR UN 3286 3/PG 2
WGK Germany 1
RTECS EO3330000
2-10
Autoignition Temperature716 °F
TSCA Yes
HazardClass 3
PackingGroup II
HS Code 29211980
Hazardous Substances Data75-64-9(Hazardous Substances Data)
ToxicityLD50 orally in Rabbit: 80 mg/kg
MSDS Information
ProviderLanguage
2-Amino-2-methylpropane English
SigmaAldrich English
ACROS English
ALFA English
tert-Butylamine Usage And Synthesis
Chemical Propertiestert-Butylamine is a colorless liquid with a typical amine-like odor. It is one of the four isomeric amines of butane, the others being n-butylamine, sec-butylamine and isobutylamine. Butylamines are highly flammable, colorless liquids (n-turns yellow on standing) with ammoniacal or fishlike odors. tert-Butylamine is used in the preparation of insecticides, pharmaceuticals, oil additives, and rubber accelerators.
Usestert-butylamine is used as a precursor for the preparation of rubber accelerators, pharmaceuticals and dyes. It is employed in synthesis of N-tert-butyl-acetamide, isoquinolines, pyridines, decumbenine, sulfontes, sulfonamides and methyl beta-ketophosphonate. It is also used in the study the effect of amines in influencing atmospheric sulfuric acid - water nucleation, hydroamination of terminal alkynes and measuring the surface acidity of solid catalyst. It acts as an indicator molecule in the study of NMR -based pH determination method.
Preparationtert-Butylamine is produced commercially by direct amination of isobutylene using zeolite catalysts:
NH3 + CH2=C(CH3)2 → H2NC(CH3)3
The Ritter reaction of isobutene with hydrogen cyanide is not useful because it produces too much waste.
(CH3)2C=CH2 + HCN + H2O → (CH3)3CNHCHO
(CH3)3CNHCHO + H2O → (CH3)3CNH2 + HCO2H
In the laboratory, it can be prepared by the hydrogenolysis of 2,2-dimethylethylenimine, or via tert-butylphthalimide.
Production Methodstert-Butylamine is manufactured by reacting isobutylamine with sulfuric acid followed by cyanide to tert-butylformamide. Hydrolysis yields t-butylamine. It is used as a solvent and in organic syntheses.
DefinitionChEBI: Tert-butylamine is a primary aliphatic amine that is ethylamine substituted by two methyl groups at position 1. It is a conjugate base of a tert-butylammonium.
General DescriptionTert-butylamine appears as a clear colorless liquid with an ammonia-like odor. Flash point 70°F. Less dense (at 6.2 lb / gal) than water. Vapors heavier than air. Toxic oxides of nitrogen produced during combustion.
Air & Water ReactionsHighly flammable. May be sensitive to air . Soluble in water.
Reactivity Profiletert-Butylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen is generated in combination with strong reducing agents, such as hydrides. Undergoes highly exothermic reaction with 2,2-dibromo-1,3-dimethylcyclopropanoic acid [J. Chem. Soc., 1, 1979, 2324].
HazardSkin irritant. Flammable, dangerous fire risk.
Health HazardInhalation causes irritation of nose, mouth, and lungs. Ingestion causes irritation of mouth and stomach. Contact with liquid causes severe irritation of eyes and moderate irritation of skin.
Fire HazardSpecial Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire.
Safety ProfilePoison by ingestion. Moderately toxic to humans by inhalation. A corrosive liquid. See also n-BUTYLAMINE and AMINES. Very dangerous fire hazard when exposed to heat or flame. Very exothermic reaction with 2,2-dibromo-l,3 dimethylcyclopropanoic acid. To fight fire, use alcohol foam. When heated to decomposition it emits toxic fumes of NOx.
Potential ExposureAlert: (n-isomer): Possible risk of forming tumors, suspected of causing genetic defects, suspected reprotoxic hazard, Primary irritant (w/o allergic reaction), (sec-isomer): Drug. n-Butylamine is used in pharmaceuticals; dyestuffs, rubber, chemicals, emulsifying agents; photography, desizing agents for textiles; pesticides, and synthetic agents. sec-Butylamine is used as a fungistate. tert-Butylamine is used as a chemical intermediate in the production of tert-Butylaminoethyl methacrylate (a lube oil additive); as an intermediate in the production of rubber and in rust preventatives and emulsion deterrents in petroleum products. It is used in the manufacture of several drugs
ShippingUN1125 n-Butylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material. UN2014 Isobutylamine, Hazard Class: 3; Labels: 3—Flammable liquid, 8—Corrosive material
Purification MethodsDry it with KOH or LiAlH4, and/or distil it from CaH2 or BaO. [Beilstein 4 IV 657.]
IncompatibilitiesMay form explosive mixture with air. May accumulate static electrical charges, and may causeignition of its vapors. n-Butylamine is a weak base; reacts with strong oxidizers and acids, causing fire and explosion hazard. Incompatible with organic anhydrides; isocyanates, vinyl acetate; acrylates, substituted allyls; alkylene oxides; epichlorohydrin, ketones, aldehydes, alcohols, glycols, phenols, cresols, caprolactum solution. Attacks some metals in presence of moisture. The tert-isomer will attack some forms of plastics
Waste DisposalUse a licensed professional waste disposal service to dispose of this material. Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner andscrubber. All federal, state, and local environmental regulations must be observed.
4-tert-Butylcatechol Dimethyl sulfone Lithium bis(trimethylsilyl)amide tert-Butyllithium tert-Butyl methyl ether Recombinant Human Telomerase Poly(dimethylsiloxane) tert-Butyldimethylsilyl chloride ALTRENOGEST Methyl 4-tert-butylbenzoate N,N-Dimethylethylamine 2-Dimethylaminoethanol Butylamine Dimethyl sulfoxide Tris(hydroxymethyl)aminomethane AMINO ACIDS N,N-Dimethylacetamide tert-Butylamine

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