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2-(Butylamino)ethanol, also known as N-Butylethanolamine, is a secondary amine that features a hydroxyl (-OH) group. It is characterized as a colorless liquid and is utilized in various chemical syntheses due to its unique structural properties.

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  • 111-75-1 Structure
  • Basic information

    1. Product Name: 2-(BUTYLAMINO)ETHANOL
    2. Synonyms: butylethanalamine;Butylethanolamine;Butylmonoethanolamine;N-Butyl monoethanolamine;n-Butylaminoethanol;Buthylethanolamine;N-n-Buthylethanolamine;2-(BUTYLAMINO)ETHANOL, 98+%
    3. CAS NO:111-75-1
    4. Molecular Formula: C6H15NO
    5. Molecular Weight: 117.19
    6. EINECS: 203-904-5
    7. Product Categories: N/A
    8. Mol File: 111-75-1.mol
  • Chemical Properties

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

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

111-75-1 Usage

Uses

Used in Pharmaceutical Synthesis:
2-(Butylamino)ethanol is used as a synthetic intermediate for the production of specific pharmaceutical compounds. Its ability to form stable bonds with other molecules makes it a valuable component in the creation of various drugs.
Used in Chemical Research:
In the field of chemical research, 2-(Butylamino)ethanol is used as a reagent in the synthesis of complex organic molecules. Its presence can influence the reaction pathways and outcomes, contributing to the development of new chemical entities.
Used in the Synthesis of 4-alkylamino-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidines:
2-(Butylamino)ethanol serves as a key component in the synthesis of this class of pyrrolo[2,3-d]pyrimidines, which are of interest in medicinal chemistry for their potential therapeutic properties.
Used in the Synthesis of N-butyl-N-(2-nitroxyethyl)nitramine (BuNENA):
2-(Butylamino)ethanol is used as a starting material in the synthesis of BuNENA, which is relevant in the field of explosives and propellants due to its high energy density and stability.

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

Check Digit Verification of cas no

The CAS Registry Mumber 111-75-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,1 and 1 respectively; the second part has 2 digits, 7 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 111-75:
(5*1)+(4*1)+(3*1)+(2*7)+(1*5)=31
31 % 10 = 1
So 111-75-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H15NO/c1-2-3-4-7-5-6-8/h7-8H,2-6H2,1H3

111-75-1 Well-known Company Product Price

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  • Aldrich

  • (471496)  2-(Butylamino)ethanol  ≥98%

  • 111-75-1

  • 471496-500ML

  • 651.69CNY

  • Detail
  • Aldrich

  • (471496)  2-(Butylamino)ethanol  ≥98%

  • 111-75-1

  • 471496-2L

  • 1,002.69CNY

  • Detail
  • Aldrich

  • (471496)  2-(Butylamino)ethanol  ≥98%

  • 111-75-1

  • 471496-20L

  • 5,365.62CNY

  • Detail

111-75-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(Butylamino)Ethanol

1.2 Other means of identification

Product number -
Other names 2-(BUTYLAMINO)ETHANOL

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. CBI
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:111-75-1 SDS

111-75-1Synthetic route

oxirane
75-21-8

oxirane

N-butylamine
109-73-9

N-butylamine

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
In ethanol; water at 30 - 40℃;78%
With water
2-isobutyl-3-butyloxazolidine
1630-71-3

2-isobutyl-3-butyloxazolidine

A

i-Amyl alcohol
123-51-3

i-Amyl alcohol

B

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C

1-butyl-3-isopropylpyrrole
91322-90-6

1-butyl-3-isopropylpyrrole

Conditions
ConditionsYield
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

4-Butyl-1-oxa-4-aza-spiro[4.5]decane

A

1-butyl-4,5,6,7-tetrahydro-1H-indole
51265-35-1

1-butyl-4,5,6,7-tetrahydro-1H-indole

B

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C

cyclohexanol
108-93-0

cyclohexanol

Conditions
ConditionsYield
With potassium hydroxide Heating; CH3ONa as reagent;A 62%
B n/a
C n/a
1-bromo-butane
109-65-9

1-bromo-butane

ethanolamine
141-43-5

ethanolamine

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
at 50 - 60℃;
at 50 - 60℃;
ethanolamine
141-43-5

ethanolamine

butyraldehyde
123-72-8

butyraldehyde

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
With ethanol; platinum Hydrogenation;
N-butylamine
109-73-9

N-butylamine

2-chloro-ethanol
107-07-3

2-chloro-ethanol

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

1-Butyltriazoline

1-Butyltriazoline

A

N-butylaziridine
1120-85-0

N-butylaziridine

B

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C

acetaldehyde
75-07-0

acetaldehyde

D

N-butylamine
109-73-9

N-butylamine

Conditions
ConditionsYield
With water at 25℃; Rate constant; Mechanism; pH 10.75 (lysine buffer); H/D isotope effect;
ethanol
64-17-5

ethanol

ethanolamine
141-43-5

ethanolamine

butyraldehyde
123-72-8

butyraldehyde

platinum oxide

platinum oxide

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
Hydrogenation;
N-<2-hydroxy-ethyl>-N-butyl-aniline

N-<2-hydroxy-ethyl>-N-butyl-aniline

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
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

n-butyldiethanolamine

ammonia
7664-41-7

ammonia

hydrogen

hydrogen

Raney nickel

Raney nickel

A

N-butylpiperazine
5610-49-1

N-butylpiperazine

B

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C

N-(2-aminoethyl)-N-butyl-1,2-ethanediamine
30935-67-2

N-(2-aminoethyl)-N-butyl-1,2-ethanediamine

Conditions
ConditionsYield
at 200℃; under 51485.6 Torr;
ethanolamine
141-43-5

ethanolamine

butan-1-ol
71-36-3

butan-1-ol

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
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

C6H13NO

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Conditions
ConditionsYield
With sodium tetrahydroborate
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

Methyl 4-bromobutyrate
4897-84-1

Methyl 4-bromobutyrate

methyl 4-(butyl(2-hydroxyethyl)amino)butanoate

methyl 4-(butyl(2-hydroxyethyl)amino)butanoate

Conditions
ConditionsYield
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

dichloro-acetic acid

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C6H15NO*C2H2Cl2O2

C6H15NO*C2H2Cl2O2

Conditions
ConditionsYield
In methanol at 20℃; for 24h;98%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

salicylic acid
69-72-7

salicylic acid

2-hydroxy-N-butylethanaminium salicylate

2-hydroxy-N-butylethanaminium salicylate

Conditions
ConditionsYield
In methanol at 0 - 50℃;97.59%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

4-Ethyl-4-hydroxyhex-2-ynenitrile
107291-76-9

4-Ethyl-4-hydroxyhex-2-ynenitrile

2-[Butyl-(2,2-diethyl-5-imino-2,5-dihydro-furan-3-yl)-amino]-ethanol
134965-81-4

2-[Butyl-(2,2-diethyl-5-imino-2,5-dihydro-furan-3-yl)-amino]-ethanol

Conditions
ConditionsYield
In dichloromethane at 40℃; for 24h;95%
carbon disulfide
75-15-0

carbon disulfide

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C7H14NOS2(1-)*K(1+)

C7H14NOS2(1-)*K(1+)

Conditions
ConditionsYield
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

triethylsilane

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

1-triethylsilyloxy-2-(butylamino)ethane
20467-03-2

1-triethylsilyloxy-2-(butylamino)ethane

Conditions
ConditionsYield
With nickel at 130℃; for 2h;93%
With sodium
tetrahydrofuran-2-carbaldehyde
7681-84-7

tetrahydrofuran-2-carbaldehyde

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

2-(2'-tetrahydrofuryl)-3-butyl-1,3-oxazolidine
78749-73-2

2-(2'-tetrahydrofuryl)-3-butyl-1,3-oxazolidine

Conditions
ConditionsYield
92%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

acetyl chloride
75-36-5

acetyl chloride

1-acetoxy-2-(acetyl-butyl-amino)-ethane
19520-95-7

1-acetoxy-2-(acetyl-butyl-amino)-ethane

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 18h; Acetylation;92%
carbon disulfide
75-15-0

carbon disulfide

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

silver(l) oxide
20667-12-3

silver(l) oxide

C7H14NOS2(1-)*Ag(1+)

C7H14NOS2(1-)*Ag(1+)

Conditions
ConditionsYield
In dichloromethane at 0 - 20℃; for 10h; Inert atmosphere; Schlenk technique;89%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

methyl 2-(4-benzoylphenoxy)acetate
57682-09-4

methyl 2-(4-benzoylphenoxy)acetate

C21H25NO4
1129771-59-0

C21H25NO4

Conditions
ConditionsYield
With potassium hydroxide at 105℃; for 2h;87%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

carbon monoxide
201230-82-2

carbon monoxide

4-butyl-2,3-morpholinedione

4-butyl-2,3-morpholinedione

Conditions
ConditionsYield
With dichloro bis(acetonitrile) palladium(II); copper(l) iodide; oxygen In acetonitrile for 20h; Ambient temperature;86%
chloroform
67-66-3

chloroform

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

2-(N-butyl-N-formylamino)ethanol

2-(N-butyl-N-formylamino)ethanol

Conditions
ConditionsYield
With potassium fluoride on basic alumina In acetonitrile at 20℃; for 24h;86%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

(1-Isothiocyanato-2-methyl-propyl)-benzene
74788-58-2

(1-Isothiocyanato-2-methyl-propyl)-benzene

1-Butyl-1-(2-hydroxy-ethyl)-3-(2-methyl-1-phenyl-propyl)-thiourea
74787-94-3

1-Butyl-1-(2-hydroxy-ethyl)-3-(2-methyl-1-phenyl-propyl)-thiourea

Conditions
ConditionsYield
In chloroform for 1h; Heating;85.7%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

1-bromomethyl-4-iodobenzene
16004-15-2

1-bromomethyl-4-iodobenzene

2-[Butyl-(4-iodo-benzyl)-amino]-ethanol
106790-67-4

2-[Butyl-(4-iodo-benzyl)-amino]-ethanol

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 80℃; for 4h;85%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

3-Chloro-2-methylpropene
563-47-3

3-Chloro-2-methylpropene

2-[Butyl-(2-methyl-allyl)-amino]-ethanol

2-[Butyl-(2-methyl-allyl)-amino]-ethanol

Conditions
ConditionsYield
With sodium carbonate In ethanol; water Heating;83%
2-acetoxyacetophenone
2243-35-8

2-acetoxyacetophenone

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

4-butyl-2-phenyl-morpholine
21532-12-7

4-butyl-2-phenyl-morpholine

Conditions
ConditionsYield
With formic acid at 180℃; for 20h;82%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

5-bromo-6-oxo-1,6-dihydropyridine-2-carboxylic acid
1214385-51-9

5-bromo-6-oxo-1,6-dihydropyridine-2-carboxylic acid

7-bromo-2-butyl-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione
1420476-85-2

7-bromo-2-butyl-3,4-dihydro-1H-pyrido[1,2-a]pyrazine-1,6(2H)-dione

Conditions
ConditionsYield
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

2-butylamino-ethanol

isoquinoline-5-sulfonyl chloride hydrochloride
105627-79-0

isoquinoline-5-sulfonyl chloride hydrochloride

Isoquinoline-5-sulfonic acid butyl-(2-hydroxy-ethyl)-amide
116970-52-6

Isoquinoline-5-sulfonic acid butyl-(2-hydroxy-ethyl)-amide

Conditions
ConditionsYield
With sodium hydrogencarbonate 1) H2O, 2) CHCl3, RT, 1 h;79%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide
77545-45-0

3’,6’-dichlorospiro[3H-2,1-benzoxathiol-3,9’-[9H]xanthene]-1,1-dioxide

C31H38N2O6S

C31H38N2O6S

Conditions
ConditionsYield
In isopropyl alcohol at 80℃; for 8h;78%
3-(4-hydroxy-3-methoxyphenyl)acrylic acid
1135-24-6

3-(4-hydroxy-3-methoxyphenyl)acrylic acid

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

2‑(butylamino)ethanol ferulate

2‑(butylamino)ethanol ferulate

Conditions
ConditionsYield
In water for 24h;77.66%
In water for 24h; Reflux;
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

4-butyl-2,3-morpholinedione

4-butyl-2,3-morpholinedione

Conditions
ConditionsYield
With potassium hydroxide 1) 110 deg C, 2 h; 2) 100 deg C, 2 h;75%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

C17H25N3O2
1346549-28-7

C17H25N3O2

C23H40N4O3
1346549-30-1

C23H40N4O3

Conditions
ConditionsYield
In chloroform for 4h; Inert atmosphere;75%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

propargyl bromide
106-96-7

propargyl bromide

N-Butyl-N-(2-hydroxyethyl)-propargylamin
13105-74-3

N-Butyl-N-(2-hydroxyethyl)-propargylamin

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; toluene at 0 - 20℃;75%
Glyoxal
131543-46-9

Glyoxal

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

N-butylmorpholine-2-one
68182-84-3

N-butylmorpholine-2-one

Conditions
ConditionsYield
In water for 1h; Heating;73%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

4-chloro-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine

4-chloro-2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)-7H-pyrrolo[2,3-d]pyrimidine

A

2-[butyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amino]ethan-1-ol

2-[butyl[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yl]amino]ethan-1-ol

B

butyl[2-[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yloxy]ethyl]amine

butyl[2-[2,5,6-trimethyl-7-(2,4,6-trimethylphenyl)pyrrolo[2,3-d]pyrimidin-4-yloxy]ethyl]amine

Conditions
ConditionsYield
In dimethyl sulfoxide at 130℃; for 6h;A 71%
B 24%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

3-chloroprop-1-ene
107-05-1

3-chloroprop-1-ene

2-(allyl-butyl-amino)-ethanol
152563-34-3

2-(allyl-butyl-amino)-ethanol

Conditions
ConditionsYield
With sodium carbonate In ethanol; water Heating;70%
2-chloro-6-methoxy-3-nitropyridine
38533-61-8

2-chloro-6-methoxy-3-nitropyridine

2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

2-[butyl-(6-methoxy-3-nitro-pyridin-2-yl)amino]ethanol
677277-87-1

2-[butyl-(6-methoxy-3-nitro-pyridin-2-yl)amino]ethanol

Conditions
ConditionsYield
In 1,4-dioxane; water for 2h; Heating / reflux;70%
2-butylamino-ethanol
111-75-1

2-butylamino-ethanol

α-bromoacetophenone
70-11-1

α-bromoacetophenone

4-Butyl-2-phenyl-morpholin-2-ol; hydrochloride
126806-92-6

4-Butyl-2-phenyl-morpholin-2-ol; hydrochloride

Conditions
ConditionsYield
In diethyl ether68%

111-75-1Relevant articles and documents

METHOD FOR PRODUCING CIS- AND TRANS-ENRICHED MDACH

-

, (2017/09/23)

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.

Benzazepine Dicarboxamide Compounds

-

Paragraph 0477; 0478, (2016/09/26)

This invention relates to novel benzazepine dicarboxamide compounds of the formula wherein R1 to R4 are as defined in the description and in the claims, as well as pharmaceutically acceptable salts thereof. These compounds are TLR agonists and may therefore be useful as medicaments for the treatment of diseases such as cancer, autoimmune diseases, inflammation, sepsis, allergy, asthma, graft rejection, graft-versus-host disease, immunodeficiencies, and infectious diseases.

N-Alkylation of Alkylolamines with Alcohols Over Mesoporous Solid Acid–Base Cs–B–Zr Catalyst

Chen, Aimin,Wang, Houyong,Liu, Rui,Bo, Yingying,Hu, Jun

, p. 1182 - 1193 (2016/07/06)

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.]

Synthesis of pyrrole N-derivatives from oxazolidines

Sadykov, E. Kh.,Stankevich,Lobanova,Klimenko

, p. 219 - 224 (2014/04/17)

Transformations of oxazolidine derivatives synthesized from industrially produced amino alcohols, aldehydes, and ketones under basic or acidic catalysis lead to the formation of N-alkyl- and N-(hydroxyalkyl)-substituted pyrroles in 19-81% yields.

Endothelin antagonists

-

, (2008/06/13)

A compound of the formula (I): or a pharmaceutically acceptable salt thereof is disclosed, as well as processes for and intermediates in the preparation thereof, and a method of antagonizing endothelin.

Acid-Catalyzed Decomposition of 1-Alkyltriazolines: A Mechanistic Study

Smith, Richard H.,Wladkowski, Brian D.,Taylor, Jesse E.,Thompson, Erin J.,Pruski, Brunon,et al.

, p. 2097 - 2103 (2007/10/02)

1-Alkyltriazolines are five-membered cyclic triazenes containing the unusual Z-configuration for the triazene moiety.The hydrolytic decomposition of these compounds in aqueous or mixed acetonitrile-aqueous buffers leads predominantly to the formation of the corresponding 1-alkylaziridines and lesser amounts of 2-(alkylamino)ethanols, alkylamines, and acetaldehyde.The latter two products presumably result from hydrolysis of a rearrangement produkt, N-ethylidenealkylamine.Neither the nature of the 1-alkyl group nor the pH of the medium greatly influences the product distribution, although decomposition in purely aqueous buffers slightly reduces the aziridine yields.The rate of hydrolysis of 1-alkyltriazolines is about twice as fast as that of the analogous acyclic 1,3,3-trialkyltriazenes and varies in the order tert-butyl > isopropyl > ethyl > butyl > methyl > propyl > benzyl.The mechanism of the decomposition is specific acid-catalyzed (A1) involving rapid reversible protonation followed by rate-limiting formation of a 2-(alkylamino)ethyldiazonium ion.The slopes of the log kobs versus pH plots are near -1.0.The solvent deuterium isotope effect, kH2O/kD2O, is in all cases methyl > ethyl.

OXAZOLIDINES. 1. BASIC CATALYTIC DISPROPORTIONATION OF CYCLOHEXANOSPIRO-2-OXAZOLIDINES: SYNTHESIS OF N-SUBSTITUTED 4,5,6,7-TETRAHYDROINDOLES

Kukharev, B.F.,Stankevich, V.K.,Kukhareva, V.A.

, p. 437 - 439 (2007/10/02)

It has been shown that the basic catalytic disproportionation of cyclohexanospiro-2-oxazolidines in the presence of potasium hydroxide or sodium methylate leads to N-substituted 4,5,6,7-tetrahydroindoles with a yield of up to 73percent.The influence of the character of substituents at the nitrogen atom of oxazolidine on the course of the reaction has been established.

Syntheses of α-C-Functionalized N-Nitrodialkylamines: Esters of methanol and 1-ethanol

Plesch, Winfried,Wiessler, Manfred

, p. 1494 - 1503 (2007/10/02)

The α-acetoxynitramines 5 and 6 - important derivatives for studying the biological properties of N-nitrodialkylamines 4 - have been synthesized, and the stability of the ester bond has been investigated.The reaction of N-nitroalkylamines 7 with 1-halogenoethyl acetates 9, thought to afford 6, yielded the diazene N-oxides 10 as the main products.

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