109-73-9

Basic information

• Product Name: Butylamine
• Synonyms: Butylamin;Butylamine, n;femanumber3130.;Monobutilamina;Monobutylamine;n-Butilamina;N-Butylamin;n-C4H9NH2
• CAS NO: 109-73-9
• Molecular Formula: C₄H₁₁N
• Molecular Weight: 73.14
• EINECS: 203-699-2
• Product Categories: Pharmaceutical Intermediates;Anilines, Aromatic Amines and Nitro Compounds;Alkylamines;Monofunctional & alpha,omega-Bifunctional Alkanes;Monofunctional Alkanes;Amines;Building Blocks;C2 to C5;Chemical Synthesis;Nitrogen Compounds;Organic Building Blocks
• Mol File: 109-73-9.mol
• Article Data: 339

Chemical Properties

• Melting Point: −49 °C(lit.)
• Boiling Point: 78 °C(lit.)
• Flash Point: 30 °F
• Appearance: Clear/Liquid
• Density: 0.74 g/mL at 25 °C(lit.)
• Vapor Density: 2.5 (vs air)
• Vapor Pressure: 68 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.401(lit.)
• Storage Temp.: 2-8°C
• Solubility: water: miscible
• PKA: 10.77(at 20℃)
• Explosive Limit: 1.5-9.8%(V)
• Water Solubility: MISCIBLE
• Sensitive: Air Sensitive
• Stability: Stable. Incompatible with oxidizing agents, aluminium, copper, copper alloys, acids. Highly flammable.
• Merck: 14,1543
• BRN: 605269
• CAS DataBase Reference: Butylamine(CAS DataBase Reference)
• NIST Chemistry Reference: Butylamine(109-73-9)
• EPA Substance Registry System: Butylamine(109-73-9)

Safety Data

• Hazard Codes: F,C
• Statements: 11-20/21/22-35
• Safety Statements: 3-16-26-29-36/37/39-45
• RIDADR: UN 1125 3/PG 2
• WGK Germany: 1
• RTECS: EO2975000
• F: 34
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 109-73-9(Hazardous Substances Data)

Usage

Description

n-Butylamine is one of the four isomeric amines of butane, the others being sec-butylamine, tert-butylamine, and isobutylamine. It is a colourless to yellow liquid and is highly flammable. It is stable and incompatible with oxidising agents, aluminium, copper, copper alloys, and acids. n-Butylamine finds its uses in the manufacture of pesticides (such as thiocarbazides), pharmaceuticals, and emulsifiers. It is also a precursor for the manufacture of N,N′-dibutylthiourea, a rubber vulcanisation accelerator, and n-butylbenzenesulphonamide, a plasticiser of nylon.

Chemical Properties

n-Butylamine is a derivative of ammonia in which one of the hydrogen atoms is replaced with an alkyl group of four carbons. As such, it reacts with water and acids to form bases and salts, respectively. Acting as a very weak acid, it can react with acyl halides, anhydrides, and esters. With carbon disulfide and carbon dioxide, it forms the butyl ammonium salt of dithiocarbamic and carbamic acids, respectively. With isocyanic acid and alkyl or aryl isocyanates, it forms substituted ureas. When reacted with nitrous acid, rc-butylamine forms butyl alcohol with the release of nitrogen (Schweizer et al 1978). In the presence of water, rc-butylamine may corrode some metals (General Electric Co 1986) and attack glass (Schweizer et al 1978). Liquid n-butylamine also will attack some forms of plastics, rubber, and coatings (NIOSH 1981).

Physical properties

Butylamine has an ammoniacal odor (fishy, pungent). Clear, colorless liquid with a strong or pungent, ammonia-like odor. Slowly becomes pale yellow on prolonged storage. Experimentally determined detection and recognition odor threshold concentrations were 240 μg/m3 (80 ppbv) and 720 μmg/m3 (240 ppbv), respectively (Hellman and Small, 1974).

Occurrence

Reported found in mulberry leaves, kale, tomato, tilsit cheese, cheddar and other cheeses, caviar, fish, cooked chicken, cooked beef, beer, sherry and red wine.

Uses

n-Butylamine is used as an intermediatefor various products, including dyestuffs,pharmaceuticals, rubber chemical, synthetictanning agents, and emulsifying agents. It isused for making isocyanates for coatings.

Uses

Intermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, synthetic tanning agents

Uses

Intermediate for pharmaceuticals, dyestuffs, rubber chemicals, emulsifying agents, insecticides, synthetic tanning agents.

Definition

ChEBI: A primary aliphatic amine that is butane substituted by an amino group at position 1.

Production Methods

n-Butylamine is usually manufactured by the catalytic alkylation of ammonia with butyl alcohol, or similarly from butyraldehyde and ammonia in the presence of Raney nickel. U.S. production in 1982 was approximately 1109 metric tons (SRI 1985). Some n-butylamine is also produced as a result of fertilizer manufacture, fish processing, rendering plant operations, and sewage treatment and has been reported to be a component of animal waste (Graedel 1978).

Preparation

Catalytic alkylation of ammonia with butyl alcohol.

Aroma threshold values

Detection: 50 ppm

General Description

A clear colorless liquid with an ammonia-like odor. Flash point 10°F. Less dense (6.2 lb / gal) than water. Vapors heavier than air. Produces toxic oxides of nitrogen during combustion.

Air & Water Reactions

Highly flammable. Dissolves in water with evolution of heat. The resulting solutions are basic.

Reactivity Profile

N-BUTYL AMINE reacts violently with strong oxidizing agents and acids. Attacks copper and copper compounds [Handling Chemicals Safely 1980 p. 123]. Reacts with hypochlorites to give N-chloroamines which may be explosive when isolated [Bretherick 1979 p. 108].

Hazard

Skin irritant. Flammable, dangerous fire risk. Eye and upper respiratory tract irritant.

Health Hazard

n-Butylamine is a severe irritant to the eyes,skin, and respiratory tract. Contact of theliquid with the skin and eyes can producesevere burns. Irritation effect on rabbits’ eyeswas as severe as that produced by ethylamine(ACGIH 1986). Exposure can cause irritationof the nose and throat, and at high concen trations, pulmonary edema. Scherberger andassociates (1960) have reported erythema ofthe face and neck occurring within 3 hoursafter exposure to n-butylamine, along with aburning and itching sensation.n-Butylamine is more toxic than is eithern-propylamine or ethylamine. A 4-hourexposure to 3000-ppm concentration in airwas lethal to rats. Toxic symptoms in animalsfrom ingestion include increased pulse rate,labored breathing, and convulsions. Cyanosisand coma can occur at near-lethal dose.LD50 value, oral (rats): 366 mg/kgLD50 value, skin (guinea pigs): 366 mg/kg.

Chemical Reactivity

Reactivity with Water No reaction; Reactivity with Common Materials: May corrode some metals in presence of water; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Flush with water; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.

Industrial uses

n-Butylamine is an important intermediate in the production of pharmaceuticals, dyestuffs, synthetic tanning agents, insecticides, emulsifying agents, rubber accelerators, vulcanizing agents, and antioxidants (HSDB 1988). A flavor ingredient in seafood and chocolate, n-butylamine is also reported to be used in alcoholic beverages, ice cream, candy, baked goods, gelatins, and puddings all at a concentration of 0.1 p.p.m. (Fenaroli 1975). It is estimated that 50% of the n-butylamine produced is used for rubber processing chemicals and 50% as an intermediate in pesticide production (SRI 1982).

Potential Exposure

Alert: (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

Carcinogenicity

The concentrated liquid produced severe eye damage and skin burns in animals.

Environmental fate

Photolytic. Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions. Chemical/Physical. Reacts with mineral acids forming water-soluble salts. At an influent concentration of 1.0 g/L, treatment with GAC resulted in effluent concentration of 480 mg/L. The adsorbability of the carbon used was 103 mg/g carbon (Guisti et al., 1974).

Metabolism

Considering the industrial importance of this amine, it is surprising that no thorough studies of its metabolism have been completed. Aliphatic amines, in general, are well-absorbed from the gut and respiratory tract and readily metabolised (Beard and Noe 1981; Magos and Manson 1983). After oral administration of n-butylamine hydrochloride to humans, little n-butylamine was recovered in the urine (Rechenberger 1940) suggesting that extensive metabolism occurs. Deamination of n-butylamine has been shown to occur in slices of rat liver and brain cortex (Pugh and Quastel 1937). It is assumed that monoamine oxidase plays a role in the detoxication process by catalyzing the deamination of n-butylamine to ammonia, hydrogen peroxide, and butyraldehyde. The ammonia produced is then converted to urea and the hydrogen peroxide is reduced by catalase. The aldehyde is probably converted to the corresponding carboxylic acid by aldehyde oxidase (Beard and Noe, 1981).

storage

n-Butylamine should be protected against physical damage. Store in a cool, dry, wellventilated location, away from any area where the fi re hazard may be acute. Outside or detached storage is preferred. Separate from incompatibles. Containers should be bonded and grounded for transfer to avoid static sparks.

Shipping

UN1125 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 Methods

Dry it with solid KOH, K2CO3, LiAlH4, CaH2 or MgSO4, then reflux it with, and fractionally distil it from P2O5, CaH2, CaO or BaO. Further purification is by precipitation as the hydrochloride, m 213-213.5o, from ethereal solution by bubbling HCl gas into it. This is re-precipitated three times from EtOH by adding ether, followed by liberation of the free amine using excess strong base. The amine is extracted into ether, which is separated, dried with solid KOH, the ether removed by evaporation and then the amine is distilled. It is stored in a desiccator over solid NaOH [Bunnett & Davis J Am Chem Soc 82 665 1960, Lycan et al. Org Synth Coll Vol II 319 1943]. [Beilstein 4 IV 540.] SKIN IRRITANT.

Incompatibilities

May 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 Disposal

Use 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.

InChI:InChI=1/C4H11N/c1-2-3-4-5/h2-5H2,1H3/p+1

Synthetic route

(E)-2-((butylimino)methyl)phenol (2565-54-0) + cyclohexylamine (108-91-8) → N-(2-hydroxybenzylidene)cyclohexylamine (19028-72-9) + N-butylamine (109-73-9)

Conditions	Yield
In [D3]acetonitrile at 25℃; Equilibrium constant; Molecular sieve;	A 100% B n/a

C13H18N2O + cyclohexylamine (108-91-8) → C15H20N2O + N-butylamine (109-73-9)

Conditions	Yield
In [D3]acetonitrile at 25℃; Equilibrium constant; Molecular sieve;	A 100% B n/a

C12H18N2O2S + cyclohexylamine (108-91-8) → C14H20N2O2S + N-butylamine (109-73-9)

Conditions	Yield
In [D3]acetonitrile at 25℃; Equilibrium constant; Molecular sieve;	A 100% B n/a

propyl cyanide (109-74-0) → N-butylamine (109-73-9)

Conditions	Yield
With sodium tetrahydroborate In water; dimethyl sulfoxide at 60℃; for 4.5h; High pressure; Green chemistry;	99.9%
With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 30 - 60℃;	93%
With [DBUH(+)][C4H9COO(-)]; water; potassium formate at 70℃; for 3h; Ionic liquid;	82%

1-nitrobutane (627-05-4) + 12percent nickel/Al-SBA-15 fiber → N-butylamine (109-73-9)

Conditions	Yield
With hydrogen In ethanol at 109.84℃; under 18751.9 Torr; for 7.5h; Autoclave; Green chemistry; chemoselective reaction;	99%

butan-1-ol (71-36-3) → N-butylamine (109-73-9)

Conditions	Yield
With ammonia; hydrogen at 200℃; under 3750.38 Torr; Reagent/catalyst; Temperature; Pressure;	97.7%
With ammonia; nickel at 200℃;
With ammonia at 350 - 400℃; als Katalysatoren, eignen sich Cr2O3,NiO und SiO2 auf Al2O3;

butyraldehyde (123-72-8) → N-butylamine (109-73-9)

Conditions	Yield
With ammonia; hydrogen In methanol at 30℃; for 15h; Autoclave;	96%
With ammonium hydroxide; Ni6AlO(z); hydrogen at 80℃; under 2250.23 Torr; for 3h; Autoclave;	83%
With (S)-1-phenyl-ethylamine; pyridoxal 5'-phosphate; pQR1108 In aq. phosphate buffer; dimethyl sulfoxide at 30℃; for 18h; pH=8; Enzymatic reaction;	42%

1-nitrobutane (627-05-4) → N-butylamine (109-73-9)

Conditions	Yield
Stage #1: 1-nitrobutane In water; acetonitrile at 20℃; for 0.0833333h; Stage #2: With sodium tetrahydroborate In water; acetonitrile at 20℃; for 0.333333h;	95%
Stage #1: 1-nitrobutane In water at 20℃; for 0.0166667h; Stage #2: With sodium tetrahydroborate In water at 50℃; for 0.166667h;	93%
With triethylamine In water at 80℃; for 6h; Inert atmosphere; Green chemistry; chemoselective reaction;	91%

N,N'-di-n-butylurea (1792-17-2) + sodium p-toluenesulfonamide (18522-92-4) → N-[(butylamino)carbonyl]-4-methyl-benzenesulfonamide (64-77-7) + N-butylamine (109-73-9)

Conditions	Yield
at 150℃; for 8h; Product distribution; other time;;	A 94.5% B n/a
at 150℃; for 5h;	A 94.5% B n/a

butan-1-ol (71-36-3) → propyl cyanide (109-74-0) + N-butylamine (109-73-9)

Conditions	Yield
With ammonia; zinc(II) oxide at 420℃;	A 92.2% B n/a
With ammonia; zinc(II) oxide at 340℃; Product distribution; 1:4 molar ratio n-butyl alcohol/NH3, other temperature (300-420 deg C), other catalyst (oxidized form of SMS-4 Zn-Cr-O);;	A 86.7% B 6%

butyraldehyde oxime (110-69-0) → N-butylamine (109-73-9)

Conditions	Yield
With sodium tetrahydroborate; nickel; sodium hydroxide In methanol; water at 20 - 30℃;	90%
With nickel at 80 - 105℃; Hydrogenation;
With lithium aluminium tetrahydride; diethyl ether
With ethanol; aluminium amalgam
With sodium n-propoxide In propan-1-ol at 69.84℃; for 2h; Reagent/catalyst;	98 %Chromat.

1-bromo-butane (109-65-9) → N-butylamine (109-73-9)

Conditions	Yield
With 5-methyl-1,3,4-thiadiazol-2-amine; triethylamine In ethanol; water at 25℃; for 1h;	89%
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 75℃; for 10h;	85%
With 2-methoxy-ethanol; sodium tetraamidoalanate In benzene at 50℃; for 6h; Product distribution; further educt/reagent ratios, temperatures, reaction times;	57%

tert-butyl butylcarbamate (59255-58-2) → N-butylamine (109-73-9)

Conditions	Yield
With water at 100℃; for 13h;	87%

N-Benzyl-N-butylamine (2403-22-7) → benzaldehyde (100-52-7) + N-butylamine (109-73-9)

Conditions	Yield
With dipotassium peroxodisulfate; tris(2,2'-bipyridyl)ruthenium dichloride In water; acetonitrile at 20℃; for 12h; Irradiation;	A 87% B n/a

N-butyl-4-toluenesulfonamide (1907-65-9) → N-butylamine (109-73-9)

Conditions	Yield
With cesium fluoride supported on Celite at 120℃; for 2.5h; chemoselective reaction;	86%

5-chloro-valeric acid (1119-46-6) → piperidine (110-89-4) + piperidin-2-one (675-20-7) + 1-pentanamine (110-58-7) + N-butylamine (109-73-9)

Conditions	Yield
Stage #1: 5-chloro-valeric acid With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 6.5h; Cooling with ice; Green chemistry;	A 85% B 9% C 2% D 2%

n-Butyl chloride (109-69-3) → N-butylamine (109-73-9)

Conditions	Yield
With copper(ll) sulfate pentahydrate; ammonium hydroxide In PEG1000-DIL; methyl cyclohexane at 75℃; for 10h;	84%
With dibutyl ether; ammonia; water at 175℃;
With ammonia; water at 170℃;
With ammonia; water; dibutylamine at 175℃;
With tributyl-amine; ammonia; water at 175℃;

butyric acid (107-92-6) → butanamide (541-35-5) + N-butyl-butyramide (10264-16-1) + dibutylamine (111-92-2) + N-butylamine (109-73-9)

Conditions	Yield
Stage #1: butyric acid With cyclopentyl methyl ether; ammonia at 200℃; under 4500.45 Torr; Sealed tube; Green chemistry; Stage #2: With cyclopentyl methyl ether; ammonia; hydrogen at 200℃; under 42004.2 Torr; for 6.5h; Cooling with ice; Green chemistry;	A 6% B n/a C 5% D 80%

CuCl2(C4H9NH2)2 (52518-95-3) + bis(carbomethoxy)palladium bipyridine → dichloro(2,2'-bipyridine)palladium(II) (14871-92-2) + CuCl(bipyridine) (39583-95-4) + methyl N-butylcarbamate (2594-21-0) + n-butylamine hydrochloride (3858-78-4) + N-butylamine (109-73-9)

Conditions

Yield

With nitrogen In tetrahydrofuran byproducts: CuCl; Pd-compd. in THF and CuCl2(BuNH2)2 in a Cu/Pd molar ratio of 4:1 are loaded sep. in the 2 branches of an inverted-Y glass reactor. Reactor is closed under N2, contents are mixed and stirred for 1 h.; IR, GC-MS and GLC anal. of liq. phase shows presence of BuNH2COOCH3. Filtn. of solid residue (anaerobic conditions), sepn. of PdCl2(bipy) from CuCl by addn. of MeOH soln. contg. bipy, IR, elem. anal. Removal of MeOH(vac.) gives CuCl(bipy). Elem. anal.;

A n/a B n/a C 79% D n/a E n/a

C28H38N4O5 (81539-78-8) → 2,2'-diphthalimido-diethyl ether (43113-25-3) + N-butylamine (109-73-9)

Conditions	Yield
at 250℃;	A 62% B 75%

{(n-C4H9NH2)2BH2}{SC2H5} (24473-71-0) → tert-butylamine borane complex (1087352-20-2) + N,N',N''-tri-n-butylborazine (2080-01-5) + HB(NH-n-C4H9)2 (2387-02-2) + N-butylamine (109-73-9) + ethanethiol (75-08-1)

Conditions	Yield
In not given byproducts: H2; thermal decomposition between 40 and 50°C;;	A 33% B 15% C 15% D n/a E 75%
In not given

1-butyl-6-tolyl-2,5-dithiobiurea (125908-37-4) → 2-(4'-methylphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione (14731-25-0) + N-butylamine (109-73-9)

Conditions	Yield
With sodium hydroxide In water Heating;	A 74% B n/a

1-butyl-6-phenyl-2,5-dithiobiurea (2834-31-3) → N-butylamine (109-73-9) + 5-phenylamino-3H-[1,3,4]thiadiazole-2-thione (10253-83-5)

Conditions	Yield
With sodium hydroxide In water Heating;	A n/a B 73%

1-methyl-pyrrolidin-2-one (872-50-4) + ammonium hydroxide (1336-21-6) + propyl cyanide (109-74-0) → N-butylamine (109-73-9)

Conditions	Yield
In methanol	73%

butyl-N,N-diformylamine (55756-14-4) → N-butylamine (109-73-9)

Conditions	Yield
With hydrogenchloride In water for 2h; Heating;	72%

1-butyl-6-(4'-ethoxyphenyl)-2,5-dithiobiurea (125908-43-2) → 2-(4'-ethoxyphenylamino)-Δ2-1,3,4-thiadiazoline-5-thione (68161-60-4) + N-butylamine (109-73-9)

Conditions	Yield
With sodium hydroxide In water Heating;	A 72% B n/a

Butane-1,4-diol (110-63-4) → pyrrolidine (123-75-1) + 1-butylpyrrolidine (767-10-2) + 4-(pyrrolidin-1-yl)butan-1-ol (93264-47-2) + 1,4-di-(1-pyrrolidinyl)butane (41726-75-4) + N-butylamine (109-73-9)

Conditions	Yield
With ammonia; hydrogen; iron RFC at 260℃; Product distribution; Mechanism; other temp. (280, 300, 310 deg C);	A 71% B 12% C n/a D n/a E 9%

phthalic anhydride (85-44-9) + N-butylamine (109-73-9) → N-butylphthalimide (1515-72-6)

Conditions	Yield
for 0.0333333h; microwave irradiation;	100%
In decaethylene glycol at 120℃; for 6h;	98%
In water at 90 - 180℃; for 0.8h; Inert atmosphere;	96.2%

2-chloro-5-nitropyridine (4548-45-2) + N-butylamine (109-73-9) → N-(5-nitropyridin-2-yl)butylamine (26820-54-2)

Conditions	Yield
In dimethyl sulfoxide at 25℃;	100%
With ethanol
In methanol for 2h; Heating;
In dimethyl sulfoxide at 25℃; Kinetics;
In acetonitrile at 25℃; Kinetics; Further Variations:; amine concentration;

4-bromo-1,8-naphthalenedicarboxylic anhydride (81-86-7) + N-butylamine (109-73-9) → 4-bromo-N-butylnaphthalimide (92874-17-4)

Conditions	Yield
In ethanol at 78℃; for 4h;	100%
In ethanol for 26h; Reflux;	100%
for 3h; Reflux;	94.5%

4-Nitrophenyl isocyanate (100-28-7) + N-butylamine (109-73-9) → N-butyl-N'-(4'-nitrophenyl)urea (21260-50-4)

Conditions	Yield
In 1,4-dioxane at 20℃; for 1h;	100%
In 1,4-dioxane at 20 - 40℃; for 3h;	100%
In 1,4-dioxane	96%

2,4-Dinitrofluorobenzene (70-34-8) + N-butylamine (109-73-9) → 2,4-dinitro-N-butylaniline (13059-86-4)

Conditions	Yield
With 2-hydroxypyridin In benzene at 25℃; Rate constant; other catalysts, other solvents, var. conc. of catalysts;	100%
With 1-(1-butyl)-3-methylimidazolium tetrafluoroborate In acetonitrile at 25℃; Kinetics; Further Variations:; Reagents; Solvents;	100%
at 25℃; for 2h;	56%

benzaldehyde (100-52-7) + N-butylamine (109-73-9) → N-benzylidenebutan-1-amine (1077-18-5)

Conditions	Yield
With aluminum oxide for 5h; Milling;	100%
at 20℃; for 2h;	100%
With HC(CMeN(2,6-Et2C6H3)2)Al(μ-S)2AlHC(CMeN(2,6-Et2C6H3))2 In chloroform-d1 at 20℃; for 2h; Inert atmosphere;	99%

phenyl isocyanate (103-71-9) + N-butylamine (109-73-9) → N-butyl-N'-phenylurea (3083-88-3)

Conditions	Yield
Stage #1: phenyl isocyanate; N-butylamine In dichloromethane at 60℃; Stage #2: With isatoic anhydride-N-(CH2)3-C8F17 In dichloromethane at 60℃; for 2.5h;	100%
at 20℃;	98%
In hexane at 25℃; Cooling with ice;	98%

1-amino-4-bromo-9,10-dioxoanthracene-2-sulphonic acid (116-81-4) + N-butylamine (109-73-9) → 1-amino-4-(butylamino)-9,10-dioxo-9,10-dihydroanthracene-2-sulfonic acid (101139-67-7)

Conditions	Yield
With sodium hydrogencarbonate; copper(II) sulfate; iron(II) sulfate In water at 70 - 90℃; for 4h;	100%
With copper(I) sulfate; water; sodium carbonate; copper(II) sulfate at 80 - 90℃;

N-butylamine (109-73-9) + 2-Bromoacetyl bromide (598-21-0) → 2-bromo-N-butylacetamide (67056-04-6)

Conditions	Yield
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 6.5h;	100%
In dichloromethane at 0 - 20℃; for 1.5h; Inert atmosphere;	96%
With potassium carbonate In dichloromethane; water at 0 - 20℃; for 12.5h;	95%

N-butylamine (109-73-9) + ethyl acrylate (140-88-5) → ethyl N-(n-butyl)-b-aminopropionate (10494-81-2)

Conditions	Yield
In ethanol at 20℃; for 2h; Michael addition;	100%
With poly(ethylene glycol) 2000; ruthenium trichloride at 50℃; for 8h; aza-Michael addition;	96%
Stage #1: N-butylamine With cerous nitrate for 4h; Reflux; Stage #2: ethyl acrylate for 8h; Time;	93.8%

N-butylamine (109-73-9) + 2-nitrobenzyl chloride (610-14-0) → N-butyl-2-nitrobenzamide (79903-04-1)

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	100%
With sodium hydroxide

N-butylamine (109-73-9) + phosphonic acid diethyl ester (762-04-9) → diethyl N-butylphosphoramidate (20465-03-6)

Conditions	Yield
With potassium carbonate; potassium hydrogencarbonate; tetrabutylammomium bromide In tetrachloromethane; dichloromethane at 15 - 20℃; for 2h;	100%
With copper(ll) bromide In ethyl acetate at 25℃; for 3h;	92%
Stage #1: phosphonic acid diethyl ester With pyridine In acetonitrile Stage #2: N-butylamine With iodine In acetonitrile for 0.0833333h;	85%
In tetrachloromethane; xylene

2-Chloro-3-nitropyridine (5470-18-8) + N-butylamine (109-73-9) → N-(3-nitropyridin-2-yl)butylamine (26820-68-8)

Conditions	Yield
In dimethyl sulfoxide at 25℃;	100%
In methanol for 2h; Heating;
With potassium carbonate
In dimethyl sulfoxide at 25℃; Kinetics;
In acetonitrile at 25℃; Kinetics; Further Variations:; amine concentration;

4-fluorobenzaldehyde (459-57-4) + N-butylamine (109-73-9) → (E)-N-(4-fluorobenzylidene)butan-1-amine

Conditions	Yield
In benzene at 80℃; for 2h;	100%
In neat (no solvent) at 60℃; for 0.0666667h; Microwave irradiation;	98%
In diethyl ether Ambient temperature;	87%

acetic acid (64-19-7) + N-butylamine (109-73-9) → N-butylacetamide (1119-49-9)

Conditions	Yield
zirconium(IV) oxide at 200℃; Product distribution; the liquid- and vapor-phase amidation were investigated with different heterogeneous catalysts;	100%
zirconium(IV) oxide at 200℃;	100%
With (1-methyl-3-(3-sulfopropyl)-1H-imidazol-3-ium)3[PW12O403-] In neat (no solvent) at 100℃; for 0.0833333h; Green chemistry;	93%

N,N-dimethyl-formamide dimethyl acetal (4637-24-5) + N-butylamine (109-73-9) → N2-n-butyl-N1,N1-dimethylformamidine (3717-82-6)

Conditions	Yield
at 60℃;	100%

ethyl acetate (141-78-6) + N-butylamine (109-73-9) → N-butylacetamide (1119-49-9)

Conditions	Yield
zirconium(IV) oxide at 200℃;	100%
With tin(IV) oxide at 200℃; further conditions: liquid phase, reflux;	79%
With aluminum oxide; monoaluminum phosphate at 77℃;	75%
With potassium tert-butylate at 95℃; for 0.05h; microwave irradiation;	70%

butanoic acid ethyl ester (105-54-4) + N-butylamine (109-73-9) → N-butyl-butyramide (10264-16-1)

Conditions	Yield
at 40℃; for 1h; lipase SP 382 (from Candida sp.);	100%
Stage #1: N-butylamine With TurboGrignard In tetrahydrofuran at 20℃; for 0.1h; Microreactor; Stage #2: butanoic acid ethyl ester In tetrahydrofuran at 20℃; for 0.233333h; Bodroux reaction; Microreactor;	82%

1-chloro-4-methyl-2-nitro-benzene (89-60-1) + N-butylamine (109-73-9) → N-butyl-4-methyl-2-nitroaniline (216591-86-5)

Conditions	Yield
at 92℃; for 96h; Inert atmosphere;	100%
for 3.5h; Heating;

ethyl 5-oxo-2-phenyl-2,5-dihydroisoxazole-4-carboxaldehyde (4504-12-5) + N-butylamine (109-73-9) → N,N'-dibutyl-N''-phenylmethanetricarboxamide (146848-35-3)

Conditions	Yield
In acetone at 25℃;	100%
Irradiation; silica glass;	80%
In acetone at 20℃; for 0.25h; Irradiation;	37%

methanol (67-56-1) + N-butylamine (109-73-9) → N,N-dimethylbutylamine (927-62-8)

Conditions	Yield
chloro(cyclopentadienyl)bis(triphenylphosphine)ruthenium (II) at 100℃;	100%
With Diethyl phosphonate Rate constant; Ambient temperature;
at 150℃; under 7500.75 Torr;

1,1,1,3,3,3-hexachloro-propan-2-one (116-16-5) + N-butylamine (109-73-9) → chloroform (67-66-3) + trichloro-acetic acid butylamide (31464-96-7)

Conditions	Yield
In hexane	A n/a B 100%

4-hydroxy-4-methylhex-2-ynenitrile (32837-88-0) + N-butylamine (109-73-9) → 4-[(E)-Butylimino]-5-ethyl-5-methyl-4,5-dihydro-furan-2-ylamine (134965-70-1)

Conditions	Yield
In dichloromethane at 40℃; for 24h;	100%

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) + N-butylamine (109-73-9) → (N,N-dimethylamino)-naphthalene-N-butyl-1-sulfonamide (55032-39-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 3.5h; Inert atmosphere;	100%
	90%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	88%

o-formylbenzonitrile (7468-67-9) + N-butylamine (109-73-9) → 3-(butylamino)isoindolin-1-one (93680-02-5)

Conditions	Yield
at 20℃; for 6h;	100%
With N,N,N,N-tetraethylammonium tetrafluoroborate In acetonitrile at 20℃; Electrolysis;	85%

Upstream product

• 102-82-9 Tributylamine 
• 104-88-1 4-Chlorobenzaldehyde 
• 109-69-3 1-Chlorobutane 
• 1332-58-7 KAOLIN 
• 1336-21-6 Ammonium hydroxide 

Downstream Products

• 458-37-7 Curcumin 
• 64902-72-3 Chlorsulfuron 
• 1609-86-5 tert-Butylisocyanate 
• 83055-99-6 Bensulfuron methyl 
• 2836-82-0 2-Fluorophenylacetone 
• 79902-63-9 Simvastatin 
• 111-36-4 Butyl isocyanate 
• 102-82-9 Tributylamine 
• 17354-14-2 Solvent Blue 35 
• 2180-92-9 Bupivacaine 
• 5211-62-1 2-Methoxyphenylacetone 
• 28860-95-9 S-(-)-Carbidopa 

Recommend Products

• 111-75-1  2-butylamino-ethanol 
• 75-21-8  oxirane 
• 109-73-9  N-butylamine 
• 102-79-4  n-butyldiethanolamine 
• 871-71-6  N-butylformamide 
• 64-17-5  ethanol 
• 123-91-1  1,4-dioxane 
• 107-21-1  ethylene glycol 
• 109-94-4  formic acid ethyl ester 
• 589-33-3  N-butylpyrrole 
• 696-59-3  cis,trans-2,5-dimethoxytetrahydrofuran 
• 693-03-8  n-butyl magnesium bromide 
• 110-89-4  piperidine 
• 98549-27-0  oxalomonoimidic acid butylamide-nitrile