Home Cart Sign in  
HazMat Fee +

There will be a HazMat fee per item when shipping a dangerous goods. The HazMat fee will be charged to your UPS/DHL/FedEx collect account or added to the invoice unless the package is shipped via Ground service. Ship by air in Excepted Quantity (each bottle), which is up to 1g/1mL for class 6.1 packing group I or II, and up to 25g/25ml for all other HazMat items.

Type HazMat fee for 500 gram (Estimated)
Excepted Quantity USD 0.00
Limited Quantity USD 15-60
Inaccessible (Haz class 6.1), Domestic USD 80+
Inaccessible (Haz class 6.1), International USD 150+
Accessible (Haz class 3, 4, 5 or 8), Domestic USD 100+
Accessible (Haz class 3, 4, 5 or 8), International USD 200+
Chemical Structure| 13325-10-5 Chemical Structure| 13325-10-5
Chemical Structure| 13325-10-5

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4-Aminobutan-1-ol is a primary amine with a hydroxyl group, commonly used in the synthesis of pharmaceuticals, peptides, and polymers.

Synonyms: 4-Amino-1-butanol

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Product Citations

Agnieszka Gunia-Krzyżak ; Justyna Popiół ; Karolina Słoczyńska ; Dorota Żelaszczyk ; Paulina Koczurkiewicz-Adamczyk ; Katarzyna Wójcik-Pszczoła , et al.

Abstract: Hyperpigmentation disorders may result from inappropriate melanin deposition and/or excessive melanin synthesis. They are classified mainly as aesthetic problems, but they can significantly affect human health by decreasing self-esteem. There are available only limited treatment options for hyperpigmentation disorder, among others, cosmetic products applied topically. Depigmenting ingredients were found to be ineffective and characterized by various side effects. As a result, many efforts are made to discover novel, potent, and safe melanogenesis inhibitors for possible use in topical cosmetic depigmenting formulations. Cinnamic acid derivatives constitute a widely tested group for that purpose. This article reports research in the group of N-alkyl cinnamamide derivatives (un)substituted in phenyl ring. Among tested series, (E)-3-(4-chlorophenyl)-N-(5-hydroxypentyl)acrylamide (compound 21) showed the most promising inhibitory properties in mushroom tyrosinase assay (IC50=36.98±1.07µM for monophenolase activity, IC50=146.71±16.82µM for diphenolase activity) and melanin production inhibition in B16F10 mouse melanoma cell line at concentration 6.25 µM resulting probably from decreasing of Tyr, Mitf, Tyrp-1, and Tyrp-2 genes expression. This compound also showed melanin production inhibitory properties in pigmented reconstructed human epidermis when used in 1% and 2% solutions in 50% PEG400. In vitro evaluation of its safety profile showed no cytotoxicity to human keratinocytes HaCaT, human skin fibroblasts BJ, and human primary epidermal melanocytes HEMa, no mutagenicity in the Ames test, no genotoxicity in micronucleus test, no phototoxicity, as well as no skin irritation potential tested in PEG400 solution. This compound was also shown to penetrate across the epidermis to reach the possible site of action. The performed research led to classify (E)-3-(4-chlorophenyl)-N-(5-hydroxypentyl)acrylamide as a novel potential depigmenting cosmetic ingredient.

Keywords: Cinnamamide ; cinnamic acid derivatives ; hyperpigmentation ; tyrosinase inhibition ; melanogenesis inhibition ; reconstructed human epidermis

Purchased from AmBeed: ; ;

Alternative Products

Product Details of 4-Aminobutan-1-ol

CAS No. :13325-10-5
Formula : C4H11NO
M.W : 89.14
SMILES Code : OCCCCN
Synonyms :
4-Amino-1-butanol
MDL No. :MFCD00008230
InChI Key :BLFRQYKZFKYQLO-UHFFFAOYSA-N
Pubchem ID :25868

Safety of 4-Aminobutan-1-ol

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8
UN#:2735
Packing Group:

Application In Synthesis of 4-Aminobutan-1-ol

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 13325-10-5 ]

[ 13325-10-5 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 13325-10-5 ]
  • [ 1655-06-7 ]
  • (1S,2S)-2-Hydroxy-cyclohexanecarboxylic acid (4-hydroxy-butyl)-amide [ No CAS ]
  • (1S,2S)-2-Hydroxy-cyclohexanecarboxylic acid 4-amino-butyl ester [ No CAS ]
  • 2
  • [ 13325-10-5 ]
  • [ 18162-48-6 ]
  • [ 245660-15-5 ]
YieldReaction ConditionsOperation in experiment
100% With pyridine; for 12h;Inert atmosphere; Preparation of this compound was according to the procedure reported by Krivickas S. J. et al. TBDMSCl (8.2 g, 54 mmol, 1.2 eq) was added to a mixture of 4-aminobutanol (4 g, 45 mmol) and pyridine (8 mL). Stirring was allowed for 12 h. TLC (MeOH/CHCl3 = 5/5) indicated the consumption of 4-aminobutanol (Rf = 0.13) and formation of product 4 (Rf = 0.40). The mixture was then concentrated under reduced pressure at 40 oC to provide a residue, which was dissolved by CH2Cl2 (50 mL). After extraction with satd. NaHCO3 (aq), the organic layer was dried over Na2SO4 and filtered through celite pad to provide the filtrate, which was concentrated under reduced pressure. The residue obtained was purified by flash chromatography using silica gel (50 g) with eluents of Et3N/MeOH/CHCl3=2/10/90 to provide colorless oil 4 in quantitative yield (8.8 g). Spectroscopic data is available in the literature. Anal. C10H25NOSi, MW: 203.4, ESI+ Q-TOF MS, M = 203.2 (m/z), [M+H]+ = 204.2; 1H-NMR (500 MHz, CD3OD): d 0.06 (s, 6H, HTBDMS), 0.90 (s, 9H, HTBDMS), 1.55-1.59 (m, 4H), 2.74 (dd, 2H), 3.66 (dd, 2H).
100% With pyridine; In dichloromethane; for 12h; 2. 4-(tert-butyldimethylsilanyloxy)butan-1-amine (compound of formula 7) Preparation of this compound was according to the procedure reported by Krivickas S. J. et al. Tert-Butyldimethylsiyl Chloride (TBDMSCl) (8.2 g, 54 mmol, 1.2 eq) was added to a mixture of 4-aminobutanol (4 g, 45 mmol) and pyridine (8 mL). Stirring was allowed for 12 h. TLC (MeOH/CHCl3=5/5) indicated the consumption of 4-aminobutanol (Rf=0.13) and formation of compound of formula 7 (Rf=0.40). The mixture was then concentrated under reduced pressure at 40 C. to provide a residue, which was dissolved by CH2Cl2 (50 mL). After extraction with satd. NaHCO3 (aq), the organic layer was dried over Na2SO4 and filtered through celite pad to provide the filtrate, which was concentrated under reduced pressure. The residue obtained was purified by flash chromatography using silica gel (50 g) with eluents of Et3N/MeOH/CHCl3=2/10/90 to provide a colorless oil compound of formula 7 in quantitative yield (8.8 g). Spectroscopic data is available in the literature. Anal. C10H25NOSi, MW: 203.4, ESI+Q-TOF MS, M=203.2 (m/z), [M+H]+=204.2; 1H-NMR (500 MHz, CD3OD): δ 0.06 (s, 6H, HTBDMS), 0.90 (s, 9H, HTBDMS), 1.55-1.59 (m, 4H), 2.74 (dd, 2H), 3.66 (dd, 2H).
100% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; To a solution of 4-aminobutan-l-ol (2 g, 22 mmol) in dichloromethane (25 mL) at 0C were added triethyl amine (5.67 g, 56 mmol) followed by TBS chloride (5 g, 33 mmol) and the resulting reaction mixture was stirred at room temperature for 16h. The progress of the reaction was monitored by TLC and indicates the completion of the reaction. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium chloride solution and dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 4- ((tert-butyldimethylsilyl)oxy)butan-l -amine (4.5 g, 100%). DIMS (ESI): m/z 204.14 (M+l).
100% With triethylamine; In dichloromethane; at 0 - 20℃; for 16h; To a solution of 4-aminobutan-l-ol (2 g, 22 mmol) in dichloromethane (25 mL) at 0C were added triethyl amine (5.67 g, 56 mmol) followed by TBS chloride (5 g, 33 mmol) and the resulting reaction mixture was stirred at room temperature for 16h. The progress of the reaction was monitored by TLC and indicates the completion of the reaction. The reaction mixture was diluted with dichloromethane and washed with water, saturated sodium chloride solution and dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to afford 4- ((tert-butyldimethylsilyl)oxy)butan-l -amine (4.5 g, 100%). DIMS (ESI): m/z 204.14 (M+l).
92% With triethylamine; In dichloromethane; at 0 - 20℃; for 4h; To the solution of 4-aminobutanol (20 g, 0.224 mol) in dichloromethane (200 ml) was added triethylamine at 0 C. tert-butyldimethylchlorosilane (33.8 g, 0.224 mol) was added at the same temperature and stirred at room temperature for 4 h. The reaction mixture was diluted with water. The organic layer was washed with water, brine, dried over anh. sodium sulfate and concentrated. The crude product (42 g, 92%) was used for next step without purification.
88% With 1H-imidazole; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; General procedure: A reaction vessel containing a stirring bar under argon` (balloon) was charged with the appropriate alcohol, imidazole (2.5 equivalents) and was dissolved in anhydrous CH2Cl2 (0.2 M). The suspension was cooled to 0 C and tert-butyldimethylsilyl chloride (1.1 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 3 h.
88% With 1H-imidazole; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; General procedure: A reaction vessel containing a stirring bar under argon` (balloon) was charged with the appropriate alcohol, imidazole (2.5 equivalents) and was dissolved in anhydrous CH2Cl2 (0.2 M). The suspension was cooled to 0 C and tert-butyldimethylsilyl chloride (1.1 equivalents) was added to the reaction vessel. The reaction was stirred at room temperature for 3 h.
33% With 1H-imidazole; In dichloromethane; at 20℃; for 1h; Synthesis of O-(tert-butyldimethylsilyl)-4-amino-1-butanol. Synthesisof O-(tert-butyldimethylsilyl)-4-amino-1-butanol was adapted from a previous procedure.2Briefly, 4-amino-1-butanol (1.93 mL, 0.021 mol) and imidazole (2.72 g, 0.040 mol) weredissolved in 20 mL CH2Cl2. Tert-butyldimethylchlorosilane (TBDMS-Cl, 3.17 g, 0.021 mol) wasdissolved in 10 mL CH2Cl2 and slowly added to the ethanolamine/imidazole mixture over 5minutes. The reaction was stirred at RT for 1 hour. Deionized water (20 mL) was added, theorganic layer collected, and the aqueous layer washed twice more with CH2Cl2. The combinedorganic layers were dried over CaCl2 and concentrated in vacuo to yield a pale yellow oil (1.4 g;33% yield). ESI [M+H]+1 expected 204.18 Da, observed 204.13 Da
33% With 1H-imidazole; In dichloromethane; at 20℃; for 1.08333h; Synthesis of O-(tert-butyldimethylsilyl)-4-amino-1-butanol was adapted from a previous procedure. (Corson et al. ACS Med. Chem. Lett. 2016, 7(12).) Briefly, 4-amino-1-butanol (1.93 mL, 0.021 mol) and imidazole (2.72 g, 0.040 mol) were dissolved in 20 mL CH2Cl2. Tert-butyldimethylchlorosilane (TBDMS-Cl, 3.17 g, 0.021 mol) was dissolved in 10 mL CH2Cl2 and slowly added to the ethanolamine/imidazole mixture over 5 minutes. The reaction was stirred at room temperature for 1 hour. Deionized water (20 mL) was added, the organic layer collected, and the aqueous layer washed twice more with CH2Cl2. The combined organic layers were dried over CaCl2) and concentrated in vacuo to yield a pale yellow oil (1.4 g; 33% yield). ESI [M+H]+1 expected 204.18 Daltons (Da), observed 204.13 Da.
1H-imidazole; REFERENCE EXAMPLE 2 4-(tert-Butyldimethylsilyloxy)-1-butylamine In a manner similar to that in Reference Example 1, 4-amino-1-butanol was reacted with tert-butyldimethylsilyl chloride in the presence of imidazole to give 4-(tert-butyldimethylsilyloxy)-1-butylamine. 1H-NMR (CDCl3)δ(ppm): 0.09 (s, 6H), 0.91 (s, 9H), 1.58 (m, 4H), 3.32 (q, J=6.3 Hz, 2H), 3.64 (t, J=5.8 Hz, 1H).
With dmap; triethylamine; In dichloromethane; at 0 - 20℃; for 24h; Part A; Triethylamine (17.7 mL, 127 mmol), 4-dimethylaminopyridine (70 mg), and t~ butyldimethylsilyJ chloride (18.3 g, 121 mmol) were added to a 0 0C solution of 4-amino- 1-butanol (10.3 g, 116 mmol) in dichloromethane (100 mL). The mixture was allowed to warm to room temperature and was stirred for 1 day. The mixture was poured onto water (100 mL). The organic layer was washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 21.6 g of 4-[tert- butyl(dimethyl)sily]]oxy}butan-]-amine as an oil that contained minor impurities.
With triethylamine; In dichloromethane; at 0 - 22℃; for 18h; To a solution of 4-aminobutanol (2.08 mL, 22.44 mmol, Aldrich) in DCM (20 mL) is added TEA (3.44 mL, 24.68 mmol) at 0C. Tert-butyldimethylchlorosilane (3.72 g, 24.68 mmol, Aldrich) is added at the same temperature and stirred at RT for 18 hours. The reaction mixture is diluted with water. The organic layer is washed with water and brine, dried over Mg504, filtered and concentrated to give crude 38a, which is used as such for the next step.
With 1H-imidazole; In dichloromethane; at 20℃; for 2h; A mixture of 4-hydroxybutylamine (4.0 g, 44.9 mmol), tørt-butyldimethyl-silyl chloride (7.4 g, 49.3 mmol) and imidazole (6.7 g, 98.7 mmol) in dichloromethane (150 mL) was stirred at room temperature for 2 hours. The product mixture was washed successively with aqueous NaHCO3, water, EPO <DP n="67"/>and brine. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. This intermediate silylated aminoalcohol was used without further purification. To a mixture of the amine (1.0 g, 4.9 mmol) and benzyloxyacetaldehyde (0.74 g, 4.9 mmol) in dichloroethane (15 mL) at room temperature, sodium triacetoxyborohydride (1.3 g, 6.3 mmol) was added. The reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic extract was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with 2% methanol in dichloromethane. Collection and concentration of appropriate fractions afforded the title silyloxybutyl-amine. lH NMR (400 MHz, CDCI3) δ 7.33 -7.25 (m, 5H), 4.51 (s, 2H), 3.60 (m, 4H), 2.79 (br t, J = 4.9 Hz, 2H)52.60 (br t, 2 H), 1.52 (br signal, 5 H), 0.87 (s, 9H), 0.03 (s, 6H).

  • 3
  • [ 60159-37-7 ]
  • [ 13325-10-5 ]
  • C11H17ClN2O [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% 4-Amino-l-butanol (0.13 ml, 0.0014 mol) was added at room temperature to a mixture of l-(4-chloro-2-pyridinyl)- ethanone (200 mg, 0.0013 mol), pαrø-toluene sulfonic acid (123 mg, 0.00065 mol), and 3A molecular sieves in MeOH (4 ml). The mixture was stirred 6 hours at room temperature, cooled down to O0C, and sodium borohydride (98 mg, 0.0026 mol) was slowly added. The mixture was stirred at room temperature for 18 hours. Molecular sieves were filtered off, and the mixture was poured out into water and the solvent was evaporated. The aqueous layer was basified with a saturated solution of sodium hydrogen carbonate, and extracted 3 times with DCM. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was evaporated. The residue was purified by column chromatography over silica gel (40-63 μm) (eluent: DCM/MeOH 95/5). The pure fractions were collected and the solvent was evaporated, yielding 269 mg (91%) of intermediate 20 as a yellow oil.
  • 4
  • [ 6624-49-3 ]
  • [ 13325-10-5 ]
  • [ 600709-80-6 ]
  • 5
  • [ 1194-21-4 ]
  • [ 13325-10-5 ]
  • 2-amino-6<N-(4-hydroxybutyl)amino>pyrimidin-4(3H)-one [ No CAS ]
  • 6
  • [ 13325-10-5 ]
  • [ 34662-29-8 ]
  • [ 889884-86-0 ]
YieldReaction ConditionsOperation in experiment
49% In N,N-dimethyl-formamide; at 0 - 20℃; for 72h; To a stirring solution of <strong>[34662-29-8]2-chloro-4-cyanonitrobenzene</strong> from step i (2.48 g, 13.6 mmol) in 12 ml DMF was cooled in ice. 4-aminobutanol (5.50 ml, 59.3 mmol) was added and the reaction mixture was slowly allowed to warm to room temperature after which stirring was continued at room temperature for 72 h. H2O was added and the aqueous layer was extracted with CH2Cl2 (2×) The combined organic layers were washed with H2O (3×), dried (by a Water Repelling Filter) and evaporated under reduced pressure. The residue was chromatographed with Et2O/petroleum ether 4:1 as eluent to give 2.6 g (49%) of the amino-alkylated product
  • 7
  • [ 13325-10-5 ]
  • [ 78078-92-9 ]
  • [ 1234567-15-7 ]
  • 8
  • [ 13325-10-5 ]
  • [ 914348-80-4 ]
  • C14H15FN2OS [ No CAS ]
 

Historical Records

Technical Information

Categories