111-75-1

Basic information

• Product Name: 2-(BUTYLAMINO)ETHANOL
• Synonyms: butylethanalamine;Butylethanolamine;Butylmonoethanolamine;N-Butyl monoethanolamine;n-Butylaminoethanol;Buthylethanolamine;N-n-Buthylethanolamine;2-(BUTYLAMINO)ETHANOL, 98+%
• CAS NO: 111-75-1
• Molecular Formula: C₆H₁₅NO
• Molecular Weight: 117.19
• EINECS: 203-904-5
• Mol File: 111-75-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 28.94°C (estimate)
• Boiling Point: 198-200 °C(lit.)
• Flash Point: 170 °F
• Appearance: /
• Density: 0.891 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0875mmHg at 25°C
• Refractive Index: n20/D 1.444(lit.)
• Storage Temp.: 2-8°C
• Solubility: 1000g/l
• PKA: 14.81±0.10(Predicted)
• Explosive Limit: 1.5-8.6%(V)
• Water Solubility: 1000g/L at 20℃
• BRN: 1732522
• CAS DataBase Reference: 2-(BUTYLAMINO)ETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(BUTYLAMINO)ETHANOL(111-75-1)
• EPA Substance Registry System: 2-(BUTYLAMINO)ETHANOL(111-75-1)

Safety Data

• Hazard Codes: C
• Statements: 22-34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2735 8/PG 2
• WGK Germany: 1
• RTECS: KK0175000
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 111-75-1(Hazardous Substances Data)

Usage

Chemical Properties

Colorless liquid

Uses

2-(Butylamino)ethanol (N-Butylethanolamine) may be employed for the synthesis of 4-alkylamino-2,5,6-trimethyl -7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidines and N-butyl-N-(2-nitroxyethyl)nitramine (BuNENA).

General Description

2-(Butylamino)ethanol is a secondary amine having a -OH group.

Safety Profile

Moderately toxic by ingestion and intraperitoneal routes. A skin and severe eye irritant. See also AMINES. Combustible when exposed to heat or flame. To fight fire, use alcohol foam, foam, Con, dry chemical. Incompatible with oxihzing materials. When heated to decomposition it emits toxic fumes of NOx

InChI:InChI=1/C6H15NO/c1-2-3-4-7-5-6-8/h7-8H,2-6H2,1H3

Synthetic route

oxirane (75-21-8) + N-butylamine (109-73-9) → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
In ethanol; water at 30 - 40℃;	78%
With water

2-isobutyl-3-butyloxazolidine (1630-71-3) → i-Amyl alcohol (123-51-3) + 2-butylamino-ethanol (111-75-1) + 1-butyl-3-isopropylpyrrole (91322-90-6)

Conditions	Yield
With potassium hydroxide Reflux;	A n/a B n/a C 73%

4-Butyl-1-oxa-4-aza-spiro[4.5]decane (51370-34-4) → 1-butyl-4,5,6,7-tetrahydro-1H-indole (51265-35-1) + 2-butylamino-ethanol (111-75-1) + cyclohexanol (108-93-0)

Conditions	Yield
With potassium hydroxide Heating; CH3ONa as reagent;	A 62% B n/a C n/a

1-bromo-butane (109-65-9) + ethanolamine (141-43-5) → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
at 50 - 60℃;
at 50 - 60℃;

ethanolamine (141-43-5) + butyraldehyde (123-72-8) → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
With ethanol; platinum Hydrogenation;

N-butylamine (109-73-9) + 2-chloro-ethanol (107-07-3) → 2-butylamino-ethanol (111-75-1)

1-Butyltriazoline → N-butylaziridine (1120-85-0) + 2-butylamino-ethanol (111-75-1) + acetaldehyde (75-07-0) + N-butylamine (109-73-9)

Conditions	Yield
With water at 25℃; Rate constant; Mechanism; pH 10.75 (lysine buffer); H/D isotope effect;

ethanol (64-17-5) + ethanolamine (141-43-5) + butyraldehyde (123-72-8) + platinum oxide → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
Hydrogenation;

N-<2-hydroxy-ethyl>-N-butyl-aniline → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
With sodium nitrite und Zersetzung des Reaktionsprodukts mit konz.NaOH;
With sodium nitrite und Zersetzung des Reaktionsprodukts mit konz.NaOH;

n-butyldiethanolamine (102-79-4) + ammonia (7664-41-7) + hydrogen + Raney nickel → N-butylpiperazine (5610-49-1) + 2-butylamino-ethanol (111-75-1) + N-(2-aminoethyl)-N-butyl-1,2-ethanediamine (30935-67-2)

Conditions	Yield
at 200℃; under 51485.6 Torr;

ethanolamine (141-43-5) + butan-1-ol (71-36-3) → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
With mesoporous Cs-B-Zr mixed oxide In neat (no solvent) at 220℃; under 32253.2 Torr; for 0.5h; Autoclave; Inert atmosphere; Green chemistry;

C6H13NO → 2-butylamino-ethanol (111-75-1)

Conditions	Yield
With sodium tetrahydroborate

2-butylamino-ethanol (111-75-1) + Methyl 4-bromobutyrate (4897-84-1) → methyl 4-(butyl(2-hydroxyethyl)amino)butanoate

Conditions	Yield
Stage #1: 2-butylamino-ethanol With potassium carbonate In acetonitrile at 20℃; for 0.166667h; Stage #2: Methyl 4-bromobutyrate In acetonitrile Reflux;	100%

dichloro-acetic acid (79-43-6) + 2-butylamino-ethanol (111-75-1) → C6H15NO*C2H2Cl2O2

Conditions	Yield
In methanol at 20℃; for 24h;	98%

2-butylamino-ethanol (111-75-1) + salicylic acid (69-72-7) → 2-hydroxy-N-butylethanaminium salicylate

Conditions	Yield
In methanol at 0 - 50℃;	97.59%

2-butylamino-ethanol (111-75-1) + 4-Ethyl-4-hydroxyhex-2-ynenitrile (107291-76-9) → 2-[Butyl-(2,2-diethyl-5-imino-2,5-dihydro-furan-3-yl)-amino]-ethanol (134965-81-4)

Conditions	Yield
In dichloromethane at 40℃; for 24h;	95%

carbon disulfide (75-15-0) + 2-butylamino-ethanol (111-75-1) → C7H14NOS2(1-)*K(1+)

Conditions	Yield
With potassium hydroxide In ethanol at 0 - 20℃; for 5h; Inert atmosphere; Schlenk technique;	95%
With potassium hydroxide In ethanol at 0 - 20℃; for 5h; Schlenk technique; Inert atmosphere;	95%

triethylsilane (617-86-7) + 2-butylamino-ethanol (111-75-1) → 1-triethylsilyloxy-2-(butylamino)ethane (20467-03-2)

Conditions	Yield
With nickel at 130℃; for 2h;	93%
With sodium

tetrahydrofuran-2-carbaldehyde (7681-84-7) + 2-butylamino-ethanol (111-75-1) → 2-(2'-tetrahydrofuryl)-3-butyl-1,3-oxazolidine (78749-73-2)

Conditions	Yield
	92%

2-butylamino-ethanol (111-75-1) + acetyl chloride (75-36-5) → 1-acetoxy-2-(acetyl-butyl-amino)-ethane (19520-95-7)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 18h; Acetylation;	92%

carbon disulfide (75-15-0) + 2-butylamino-ethanol (111-75-1) + silver(l) oxide (20667-12-3) → C7H14NOS2(1-)*Ag(1+)

Conditions	Yield
In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere; Schlenk technique;	89%

2-butylamino-ethanol (111-75-1) + methyl 2-(4-benzoylphenoxy)acetate (57682-09-4) → C21H25NO4 (1129771-59-0)

Conditions	Yield
With potassium hydroxide at 105℃; for 2h;	87%

2-butylamino-ethanol (111-75-1) + carbon monoxide (201230-82-2) → 4-butyl-2,3-morpholinedione

Conditions	Yield
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; oxygen In acetonitrile for 20h; Ambient temperature;	86%

chloroform (67-66-3) + 2-butylamino-ethanol (111-75-1) → 2-(N-butyl-N-formylamino)ethanol

Conditions	Yield
With potassium fluoride on basic alumina In acetonitrile at 20℃; for 24h;	86%

2-butylamino-ethanol (111-75-1) + (1-Isothiocyanato-2-methyl-propyl)-benzene (74788-58-2) → 1-Butyl-1-(2-hydroxy-ethyl)-3-(2-methyl-1-phenyl-propyl)-thiourea (74787-94-3)

Conditions	Yield
In chloroform for 1h; Heating;	85.7%

2-butylamino-ethanol (111-75-1) + 1-bromomethyl-4-iodobenzene (16004-15-2) → 2-[Butyl-(4-iodo-benzyl)-amino]-ethanol (106790-67-4)

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 4h;	85%

2-butylamino-ethanol (111-75-1) + 3-Chloro-2-methylpropene (563-47-3) → 2-[Butyl-(2-methyl-allyl)-amino]-ethanol

Conditions	Yield
With sodium carbonate In ethanol; water Heating;	83%

2-acetoxyacetophenone (2243-35-8) + 2-butylamino-ethanol (111-75-1) → 4-butyl-2-phenyl-morpholine (21532-12-7)

Conditions	Yield
With formic acid at 180℃; for 20h;	82%

2-butylamino-ethanol (111-75-1) + 5-bromo-6-oxo-1,6-dihydropyridine-2-carboxylic acid (1214385-51-9) → 7-bromo-2-butyl-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione (1420476-85-2)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane Reflux;	82%

2-butylamino-ethanol (111-75-1) + isoquinoline-5-sulfonyl chloride hydrochloride (105627-79-0) → Isoquinoline-5-sulfonic acid butyl-(2-hydroxy-ethyl)-amide (116970-52-6)

Conditions	Yield
With sodium hydrogencarbonate 1) H2O, 2) CHCl3, RT, 1 h;	79%

2-butylamino-ethanol (111-75-1) + 3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide (77545-45-0) → C31H38N2O6S

Conditions	Yield
In isopropyl alcohol at 80℃; for 8h;	78%

3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1135-24-6) + 2-butylamino-ethanol (111-75-1) → 2‑(butylamino)ethanol ferulate

Conditions	Yield
In water for 24h;	77.66%
In water for 24h; Reflux;

2-butylamino-ethanol (111-75-1) + oxalic acid diethyl ester (95-92-1) → 4-butyl-2,3-morpholinedione

Conditions	Yield
With potassium hydroxide 1) 110 deg C, 2 h; 2) 100 deg C, 2 h;	75%

2-butylamino-ethanol (111-75-1) + C17H25N3O2 (1346549-28-7) → C23H40N4O3 (1346549-30-1)

Conditions	Yield
In chloroform for 4h; Inert atmosphere;	75%

2-butylamino-ethanol (111-75-1) + propargyl bromide (106-96-7) → N-Butyl-N-(2-hydroxyethyl)-propargylamin (13105-74-3)

Conditions	Yield
With potassium carbonate In dichloromethane; toluene at 0 - 20℃;	75%

Glyoxal (131543-46-9) + 2-butylamino-ethanol (111-75-1) → N-butylmorpholine-2-one (68182-84-3)

Conditions	Yield
In water for 1h; Heating;	73%

2-butylamino-ethanol (111-75-1) + 4-chloro-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine → 2-[butyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amino]ethan-1-ol + butyl[2-[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yloxy]ethyl]amine

Conditions	Yield
In dimethyl sulfoxide at 130℃; for 6h;	A 71% B 24%

2-butylamino-ethanol (111-75-1) + 3-chloroprop-1-ene (107-05-1) → 2-(allyl-butyl-amino)-ethanol (152563-34-3)

Conditions	Yield
With sodium carbonate In ethanol; water Heating;	70%

2-chloro-6-methoxy-3-nitropyridine (38533-61-8) + 2-butylamino-ethanol (111-75-1) → 2-[butyl-(6-methoxy-3-nitro-pyridin-2-yl)amino]ethanol (677277-87-1)

Conditions	Yield
In 1,4-dioxane; water for 2h; Heating / reflux;	70%

2-butylamino-ethanol (111-75-1) + α-bromoacetophenone (70-11-1) → 4-Butyl-2-phenyl-morpholin-2-ol; hydrochloride (126806-92-6)

Conditions	Yield
In diethyl ether	68%

Upstream product

• 141-43-5 ethanolamine 
• 123-72-8 butyraldehyde 
• 71-36-3 butan-1-ol 
• 1630-71-3 2-isobutyl-3-butyloxazolidine 
• 102-79-4 n-butyldiethanolamine 
• 7664-41-7 ammonia 
• 64-17-5 ethanol 
• 51370-34-4 4-Butyl-1-oxa-4-aza-spiro[4.5]decane 
• 109-73-9 N-butylamine 
• 107-07-3 2-chloro-ethanol 
• 109-65-9 1-bromo-butane 
• 75-21-8 oxirane 

Downstream Products

• 94912-22-8 benzilic acid-(2-butylamino-ethyl ester) 
• 78749-73-2 2-(2'-tetrahydrofuryl)-3-butyl-1,3-oxazolidine 
• 19520-95-7 2-(N-Acetyl-N-butyl-amino)-ethyl-acetat 
• 51938-14-8 N-Butylethanolnitrosamine 
• 126806-93-7 4-Butyl-2-ethoxy-2-phenyl-morpholine; hydrochloride 
• 126806-94-8 4-Butyl-2-phenyl-2-propoxy-morpholine; hydrochloride 
• 126806-95-9 2-Butoxy-4-butyl-2-phenyl-morpholine; hydrochloride 
• 344332-62-3 benzyl-butyl-(2-chloro-ethyl)-amine 
• 1120-85-0 N-butylaziridine 

Relevant articles and documents

METHOD FOR PRODUCING CIS- AND TRANS-ENRICHED MDACH

A process for preparing trans-enriched MDACH, including: distilling an MDACH starting mixture in the presence of an auxiliary, which is an organic compound having a molar mass of 62 to 500 g/mol, a boiling point at least 5° C. above the boiling point of cis,cis-2,6-diamino-1-methylcyclohexane, and 2 to 4 functional groups, each of which is independently an alcohol group or a primary, secondary or tertiary amino group. The MDACH starting mixture includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, based on the total amount of MDACH present in the MDACH starting mixture. The MDACH starting mixture includes both trans and cis isomers. Trans-enriched MDACH includes 0 to 100% by weight of 2,4-MDACH and 0 to 100% by weight of 2,6-MDACH, where the proportion of trans isomers in the mixture is higher than the proportion of trans isomers in the MDACH starting mixture.

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Abstract: The mesoporous solid acid–base Cs–B–Zr mixed oxides were synthesized using the co-precipitation method followed by a subsequent thermal treatment. The catalytic activity of solid Cs–B–Zr mixed oxide was tested for solvent free acid–base catalysed direct alkylolamines with alcohols as green alkylating agent. The effects of Cs/B/Zr ratio, calcination temperature, reaction conditions, and reaction substrate on the catalytic performance of the catalysts were investigated. The XRD, N2 adsorption–desorption, ICP-OES, FT-IR and NH3/CO2-TPD results showed that the mesoporous structure and acid–base properties of the catalysts play important roles in the reaction. A suitable number of acid and basic sites on the catalyst lead to a high activity for the N-alkylation reaction. Graphical Abstract: A direct N-alkylation of amino alcohol with alcohols has been developed using mixed oxide Cs–B–Zr as an acid–base bifunctionalized catalyst.[Figure not available: see fulltext.]

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