| Identification | More | [Name]
Dibutylamine | [CAS]
111-92-2 | [Synonyms]
DBA
DIBUTYLAMINE
DIBUTYLAMINE IN TOLUENE
DI-N-BUTYLAMINE
DNBA
LABOTEST-BB LTBB000395
N-BUTYL-1-BUTANAMINE
N-DIBUTYLAMINE
n,n-dibutylamine
(n-C4H9)2NH
1-Butanamine,N-butyl-
ai3-15329
ai3-52649
butanamine,N-butyl
Butylamine, di-N-
Dibutilamina
Dibutylamin
Di-n-butylamin
di-Normal-butylamine
N,N-Di-n-butylamine | [EINECS(EC#)]
203-921-8 | [Molecular Formula]
C8H19N | [MDL Number]
MFCD00009429 | [Molecular Weight]
129.24 | [MOL File]
111-92-2.mol |
| Chemical Properties | Back Directory | [Appearance]
Dibutylamine is a colorless liquid with an odor
of ammonia. | [Melting point ]
−62 °C(lit.)
| [Boiling point ]
159 °C(lit.)
| [density ]
0.767 g/mL at 25 °C(lit.)
| [vapor density ]
4.46 (vs air)
| [vapor pressure ]
1.9 mm Hg ( 20 °C)
| [refractive index ]
n20/D 1.417(lit.)
| [Fp ]
106 °F
| [storage temp. ]
Flammables area | [solubility ]
water: soluble3.8g/L at 20°C | [form ]
Liquid | [pka]
11.25(at 21℃) | [color ]
White | [Odor]
Weak ammonia. | [PH]
11.1 (1g/l, H2O, 20℃) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, most common metals, strong acids. Vapours may flow over surfaces to a distant source of ignition. Can form explosive mixtures with air. | [explosive limit]
0.6-6.8%(V) | [Water Solubility ]
4.05 g/L (25 ºC) | [Merck ]
14,3032 | [BRN ]
506001 | [Dielectric constant]
3.0（20℃） | [InChIKey]
JQVDAXLFBXTEQA-UHFFFAOYSA-N | [LogP]
2.1 at 23℃ | [CAS DataBase Reference]
111-92-2(CAS DataBase Reference) | [NIST Chemistry Reference]
1-Butanamine, N-butyl-(111-92-2) | [EPA Substance Registry System]
111-92-2(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R10:Flammable.
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S23:Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer) . | [RIDADR ]
UN 2248 8/PG 2
| [WGK Germany ]
1
| [RTECS ]
HR7780000
| [F ]
10 | [Autoignition Temperature]
594 °F | [TSCA ]
Yes | [HazardClass ]
8 | [PackingGroup ]
II | [HS Code ]
29211990 | [Safety Profile]
Poison by ingestion and
subcutaneous routes. Moderately toxic by
skin contact and inhalation. Corrosive. A
severe skin and eye irritant. Mutation data
reported. Flammable liquid when exposed to
heat or flame; can react with oxidizing
materials. To fight fire, use alcohol foam,
foam, CO2, dry chemical. Exothermic
reaction with cellulose nitrate does not
proceed to ignition. When heated to
decomposition it emits toxic fumes of NOx. | [Hazardous Substances Data]
111-92-2(Hazardous Substances Data) | [Toxicity]
LD50 orally in rats: 550 mg/kg (Smyth) |
| Hazard Information | Back Directory | [General Description]
A yellow-colored liquid with a amine-like odor. Denser than water. Very corrosive, may burn skin, eyes, and mucous membranes. Flash point 125°F. Combustible. Produce toxic oxides of nitrogen when burned. Used to make other chemicals. | [Reactivity Profile]
DI-N-BUTYLAMINE(111-92-2) 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 may be generated in combination with strong reducing agents, such as hydrides. | [Air & Water Reactions]
Flammable. Soluble in water. | [Health Hazard]
Inhalation causes irritation of nose, throat, and lungs; coughing; nausea; headache. Ingestion causes irritation of mouth and stomach. Contact with eyes causes irritation. Contact with skin causes irritation and dermatitis. | [Potential Exposure]
Used as a corrosion inhibitor; and
intermediate for emulsifiers, rubber products, dyes; and
insecticides. | [Fire Hazard]
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires. | [First aid]
If this chemical gets into the eyes, remove any
contact lenses at once and irrigate immediately for at least
15 minutes, occasionally lifting upper and lower lids. Seek
medical attention immediately. If this chemical contacts the
skin, remove contaminated clothing and wash immediately
with soap and water. Seek medical attention immediately.
If this chemical has been inhaled, remove from exposure,
begin rescue breathing (using universal precautions, includ-
ing resuscitation mask) if breathing has stopped and CPR
if heart action has stopped. Transfer promptly to a medical
facility. When this chemical has been swallowed, get
medical attention. If victim is conscious, administer water or milk. Do not induce vomiting. Medical observation is
recommended for 24 to 48 hours after breathing overexpo-
sure, as pulmonary edema may be delayed. As first aid for
pulmonary edema, a doctor or authorized paramedic may
consider administering a drug or other inhalation therapy. | [Shipping]
UN2248 Di-n-butylamine, Hazard class: 8;
Labels: 8-Corrosive material, 3-Flammable liquid. | [Incompatibilities]
May form explosive mixture with air.
Aqueous solution is a strong base. Incompatible with acids,
acid chlorides; acid anhydrides; halogens, isocyanates,
vinyl acetate; acrylates, substituted allyls; alkylene
oxides, epichlorohydrin, ketones, aldehydes, alcohols, gly-
cols, phenols, cresols, caprolactum solution; strong oxidi-
zers; reactive organic compounds. Attacks copper alloys,
zinc, tin, tin alloys; galvanized steel. Also, carbon dioxide
is listed as incompatible by the state of New Jersey. | [Description]
Dibutylamine is a colorless liquid with anodor of ammonia. Molecular weight = 129.28; Boilingpoint = 159-161℃; Freezing/Melting point = - 61.9 to259℃; Flash point = 42-47℃; Autoignitiontemperature = 260℃. Explosive Limits: LEL = 1.1%;UEL—unknown. Hazard Identification (based on NFPA704 M Rating System): Health 3, Flammability 2,Reactivity 0. Slightly soluble in water. | [Chemical Properties]
Dibutylamine is a colorless liquid with an odor
of ammonia. | [Chemical Properties]
n-Dibutylamine is a strong base and undergoes reactions with acids. It reacts with
carbon disulfide and carbon dioxide to form alkyl ammonium salts of dithiocarbamic
acid and carbamic acid, respectively.
n-Dibutylamine is nitrosated by nitrite at low pHs to form the mutagenic and
carcinogenic product, N-nitrosodibutylamine (Sithole and Guy 1986). | [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. | [Uses]
Dibutylamine is a secondary dialkylamine. It is a versatile intermediate with a variety of applications.
Dibutylamine is extensively used in palladium-catalyzed cross-coupling with aryl halides to synthesize arylamines, popularly known as Buchwald–Hartwig amination.
It can be used in the oxone-mediated annulation of 2-aminobenzamides and 1,2-diaminobenzenes to synthesize 2,3-dihydroquinazolin-4(1H)-ones and 1H-benzimidazoles, respectively.
It can also be used in the one-pot multicomponent reactions to synthesize tetra- and penta-substituted polyfunctional dihydropyrroles.
Dibutylamine was employed as organocatalyst during the synthesis of 2-amino-3-cyano-4H-chromen-4-ylphosphonates via Knoevenagel, Pinner and phospha-Michael reactions. Di-n-butylamine (Dibutylamine) may be used to investigate the performance of a dry sampler, with an impregnated denuder in series with a glass fibre filter for airborne isocyanates. It was used in the preparation of 1M dibutylammonium phosphate buffer. | [Production Methods]
n-Dibutylamine is prepared by two major methods. The first involves passing
ammonia and butanol over an alumina or silica catalyst at a temperature of
300-500°C and under pressure. The second method employs passing ammonia,
butanol, and hydrogen over a dehydrogenation catalyst. In each instance the
resulting mixtures are separated by continuous distillation and extraction (Schweizer
et al 1978). n-Dibutylamine can also be prepared from butyl bromide and
ammonia or by reaction of butyl chloride and ammonia (HSDB 1989). The amine
also is naturally present in food (Neurath et al 1977) and its emissions are
produced in soil and sewage. The amine is also found in the expired air of normal,
healthy, nonsmoking adults (Krotoszynski et al 1979).
N-Nitrosamines and their precursors including n-dibutylamine are present in
rubber products in which the accelerators and stabilizers used in the vulcanization
process were derived from dialkylamines. Analysis of a single extraction of rubber
nipples and baby pacifiers with artificial saliva (containing sodium nitrite) showed
n-dibutylamine levels up to 3890 p.p.b. and N-nitrosodibutylamine concentrations
as high as 427 p.p.b. (Thompson et al 1984). | [Chemical Reactivity]
Reactivity with Water No reaction; Reactivity with Common Materials: May corrode some metals and attack some forms of plastics; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent. | [Industrial uses]
Primary industrial uses of n-dibutylamine include flotation reagents, dyestuffs,
rubber vulcanization accelerators, and corrosion inhibitors (HSDB 1989). In 1985
US production totalled approximately 2000 tons. | [Metabolism]
There is little information available on the absorption, distribution and metabolism
of ra-dibutylamine. Aliphatic amines such as dibutylamine are well absorbed from
the gut. Both monoamine oxidase and diamine oxidase, which are present in most
tissues, are capable of metabolizing many exogenous amines. Although the
metabolism of primary amines is more rapid than secondary, the rate of oxidation
by the enzyme increases with chain length of the amine, reaching a maximum
of five carbon atoms (Beard and Noe 1981). Therefore, n-dibutylamine may
be metabolized by these enzyme systems although definitive evidence is lacking.
The highly carcinogenic and mutagenic N-nitrosodibutylamine is formed by
reaction of nitrite with n-dibutylamine, the highest rates of nitrosation occurring at
low pH (Sithole and Guy 1986). The n-dibutylamine present in ingested foods is
nitrosated in the stomach by endogenous nitrite from saliva, etc. together with the
sodium nitrite present in some preserved foods to form the highly toxic Nnitrosamine
(Airoldi et al 1987). Food additives such as butylated hydroxyanisole
inhibited in vitro the nitrosation of n-dibutylamine but this inhibition was not seen
in vivo in rats that were given both n-dibutylamine and sodium nitrite.
The endogenous formation of N-nitrosodibutylamine was studied in rats after
administration of sodium nitrite or sodium nitrate and n-dibutylamine (Airoldi et
al 1984). Urinary excretion of N-nitrosodibutylamine and its metabolites N-butyl-
N-(4-hydroxybutyl)-nitrosamine (BBN) and N-butyl-N-(3-carboxypropyl)nitrosamine
(BCPN) than was determined. Rats were supplied with 0.2% sodium nitrite
or 0.5% sodium nitrate in drinking water and given n-dibutylamine by gavage at 3
doses of 50 mg/kg, 8 h apart. Analysis of the 24 h urine by GC equipped with a
thermal energy analyzer failed to detect N-nitrosodibutylamine or its metabolite
BBN. However, BCPN was found in the urine of both the sodium nitrite and
sodium nitrate groups, indicating that in vivo nitrosation of n-dibutylamine had
occurred. | [storage]
Color Code—White: Corrosive or Contact Hazard;Store separately in a corrosion-resistant location. Prior toworking with dibutylamine you should be trained on itsproper handling and storage. Before entering confined spacewhere this chemical may be present, check to make surethat an explosive concentration does not exist. Store intightly closed containers in a cool, well-ventilated areaaway from incompatible materials listed above. Metal containers involving the transfer of this chemical should begrounded and bonded. Where possible, automatically pumpliquid from drums or other storage containers to processcontainers. Drums must be equipped with self-closingvalves, pressure vacuum bungs, and flame arresters. Useonly nonsparking tools and equipment, especially whenopening and closing containers of this chemical. Sources ofignition, such as smoking and open flames, are prohibitedwhere this chemical is used, handled, or stored in a mannerthat could create a potential fire or explosion hazard.Wherever this chemical is used, handled, manufactured, orstored, use explosion-proof electrical equipment andfittings. | [Purification Methods]
Dry this strong base with LiAlH4, CaH2 or KOH pellets, filter and distil it from BaO or CaH2. [Beilstein 4 IV 550.] | [Toxicity evaluation]
Animal studies have demonstrated that dibutylamine is severely irritating to the eyes. An acute oral rat LD50 value of 550 mg/kg has been reported. The 4 h LC50 in rats is 1150 mg/m3. The 1 h LC50 in rats is ＞557 ppm.
In a 90 day exposure of rats to 0, 50, 150, or 450 mg/m3, resulted in nasal metaplasia as well as a form of mucous cell hyperplasia. |
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