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4-Amino-1-butanol

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CAS:13325-10-5
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4-Amino-1-butanol Basic information
Product Name:4-Amino-1-butanol
Synonyms:NH2-(CH2)4-OH;N-ABU(4)-OL;4-HYDROXY-N-BUTYLAMINE;4-HYDROXYBUTYLAMINE;4-AMINO-1-BUTANOL;4-AMINOBUTANOL;4-AMINOBUTYL ALCOHOL;4-AMINO-N-BUTYL ALCOHOL
CAS:13325-10-5
MF:C4H11NO
MW:89.14
EINECS:236-364-4
Product Categories:Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds;omega-Aminoalkanols;omega-Functional Alkanols, Carboxylic Acids, Amines & Halides;Amino Alcohols;Organic Building Blocks;Oxygen Compounds;Miscellaneous
Mol File:13325-10-5.mol
4-Amino-1-butanol Structure
4-Amino-1-butanol Chemical Properties
Melting point 16-18 °C (lit.)
Boiling point 206 °C (lit.)
density 0.967 g/mL at 25 °C (lit.)
refractive index n20/D ~1.462(lit.)
Fp 226 °F
storage temp. Store below +30°C.
solubility Acetonitrile (Slightly), Chloroform (Sparingly), Methanol (Slightly)
form Liquid
pka15.10±0.10(Predicted)
color Clear colorless to slightly yellow
Water Solubility MISCIBLE
Sensitive Air Sensitive & Hygroscopic
BRN 1731411
Stability:Unstable in Aqueous Solution
CAS DataBase Reference13325-10-5(CAS DataBase Reference)
NIST Chemistry ReferenceNH2(CH2)4OH(13325-10-5)
EPA Substance Registry System1-Butanol, 4-amino- (13325-10-5)
Safety Information
Hazard Codes C
Risk Statements 34-22
Safety Statements 26-36/37/39-45-25
RIDADR UN 2735 8/PG 3
WGK Germany 3
34
HazardClass 8
PackingGroup III
HS Code 29221980
MSDS Information
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4-Amino-1-butanol Usage And Synthesis
Description4-Amino-1-butanol (4AB) is an important pharmaceutical intermediate compound and a precursor of biodegradable polymers for gene delivery. It can be used in organic synthesis and biological properties studies, among others. In addition, 4-Amino-1-butanol (4AB) has been shown to have a higher CO2 solubility than 2-amino-1-ethanol (MEA), which is potentially useful in solving problems related to flue gas purification[1-2].
Chemical PropertiesVery light clear yellow liquid
Uses4-Amino-1-butanol is a useful intermediate in a variety of organic synthesis. It is mainly used in personal-care products, preparation of water soluble cationic flocculants and ion exchange resins as well as in the preparation of beta-lactam antibiotics. It is used for the production of efficient anionic emulsifiers, nonionic polyethylene emulsions, water treatment, metal treatment and absorption of carbon dioxide gas. It is used as a pigment dispersion aid and curing agent in selected textile -resins.
Uses4-Amino-1-butanol was used:
  • As a linker in the synthesis of highly branched poly(β-amino esters)(HPAEs) for gene delivery.
  • As a side chain to modulate antimicrobial and hemolytic activities of copolymers.
  • In the total synthesis of (+)-fawcettimine,(+)-fawcettidine, and (?)-lycojapodine A.

Preparation4-Amino-1-butanol (4AB) can be prepared by microbiological methods. we report for the first time the fermentative production of 4AB from glucose by metabolically engineered Corynebacterium glutamicum harboring a newly designed pathway comprising a putrescine (PUT) aminotransferase (encoded by ygjG) and an aldehyde dehydrogenase (encoded by yqhD) from Escherichia coli, which convert PUT to 4AB. Application of several metabolic engineering strategies such as fine-tuning the expression levels of ygjG and yqhD, eliminating competing pathways, and optimizing culture condition further improved 4AB production. Fed-batch culture of the final metabolically engineered C. glutamicum strain produced 24.7?g/L of 4AB[1].
Synthesis
Butanal, 4-hydroxy-, oxime

412274-79-4

4-Amino-1-butanol

13325-10-5

The general procedure for synthesizing 4-amino-1-butanol from the compound (CAS:412274-79-4) was as follows: intermediate D (5.15 g, 50 mmol) from Example 2 was added to a 100 mL three-necked flask containing 50 mL of anhydrous tetrahydrofuran. Lithium aluminum hydride (2.28 g, 60 mmol) was accurately weighed and added to the flask in slow batches, followed by turning on magnetic stirring. The reaction system was heated to reflux and maintained for 1 hour. Upon completion of the reaction, ethyl acetate was carefully added to quench the excess lithium aluminum hydride. Subsequently, 10% sodium hydroxide solution was slowly added dropwise until the drop was stopped when light yellow solid precipitation was observed. Solid impurities were removed by diafiltration and the organic phase was separated to obtain the organic phase. The organic phase was purified by rotary evaporation to remove the solvent and then purified by distillation under reduced pressure to give the final yellow oily liquid product 4-amino-1-butanol (3.3 g, calculated yield).

References[1] CINDY PRICILIA SURYA PRABOWO. Microbial production of 4-amino-1-butanol, a four-carbon amino alcohol[J]. Biotechnology and Bioengineering, 2020. DOI:10.1002/bit.27438.
[2] ZULKIFLI IDRIS . Equilibrium solubility of carbon dioxide in aqueous solutions of 3-amino-1-propanol, 4-amino-1-butanol and 5-amino-1-pentanol at low partial pressures[J]. Fluid Phase Equilibria, 2015. DOI:10.1016/j.fluid.2014.11.028.
Tag:4-Amino-1-butanol(13325-10-5) Related Product Information
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