22205-09-0

Basic information

• Product Name: 4-(4-AMINOBUTYL)PHENOL
• Synonyms: 4-(4-AMINOBUTYL)PHENOL;4-(4-Aminobutyl)phenol HBr
• CAS NO: 22205-09-0
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.2322
• Mol File: 22205-09-0.mol

Chemical Properties

• Melting Point: 106-108 °C
• Boiling Point: 315.275 °C at 760 mmHg
• Flash Point: 144.473 °C
• Appearance: /
• Density: 1.05 g/cm³
• PKA: 10.10±0.15(Predicted)
• CAS DataBase Reference: 4-(4-AMINOBUTYL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(4-AMINOBUTYL)PHENOL(22205-09-0)
• EPA Substance Registry System: 4-(4-AMINOBUTYL)PHENOL(22205-09-0)

Safety Data

• Hazardous Substances Data: 22205-09-0(Hazardous Substances Data)

Usage

Uses

Used in Hair Dye Industry:
4-(4-aminobutyl)phenol is used as a hair dye ingredient for its ability to bond with hair and provide long-lasting color. It enhances the performance and effectiveness of hair dyes, offering consumers a wide range of color options and improved color retention.
Used in Pharmaceutical Industry:
In the pharmaceutical sector, 4-(4-aminobutyl)phenol serves as a key intermediate in the synthesis of various drugs. Its unique chemical structure allows for the development of new pharmaceutical compounds with potential therapeutic applications.
Used as a Corrosion Inhibitor in Metalworking Fluids:
4-(4-aminobutyl)phenol is utilized as a corrosion inhibitor in metalworking fluids to prevent the degradation of metal surfaces during manufacturing processes. Its presence in these fluids helps to extend the life of machinery and equipment, reducing maintenance costs and improving overall efficiency.
Safety Precautions:
Due to the potential for skin and eye irritation, low to moderate toxicity, and environmental hazard associated with 4-(4-aminobutyl)phenol, it is essential to exercise caution when handling this compound. Proper protective equipment, such as gloves and safety goggles, should be worn during its use. Additionally, it is crucial to follow safety guidelines and regulations to minimize the risk of exposure and environmental contamination.

Upstream product

• 501677-83-4 benzoic acid-[4-(4-amino-phenyl)-butylamide] 
• 2222-15-3 4-(4-Methoxyphenyl)-butyramide 
• 4521-28-2 4-(4-Methoxyphenyl)butyric acid 
• 7643-92-7 4-Amino-1-(4-methoxy-phenyl)-butan-1-one 
• 100-66-3 methoxybenzene 
• 861604-96-8 N-[4-(4-nitro-phenyl)-butyl]-benzamide 
• 93406-12-3 N-benzoyl-4-phenylbutylamine 
• 3153-44-4 4-(4-methoxy-phenyl)-4-oxo-butyric acid 
• 211692-37-4 2-[(E)-4-(4-Methoxy-phenyl)-but-3-enyl]-isoindole-1,3-dione 
• 52244-70-9 4-(4-methoxyphenyl)butan-1-ol 
• 23002-61-1 1-(4-chlorobutyl)-4-methoxybenzene 
• 211692-42-1 2-[4-(4-methoxy-phenyl)-butyl]-isoindole-1,3-dione 
• 847200-99-1 2-[4-(4-hydroxyphenyl)butyl]isoindole-1,3-dione 
• 72457-26-2 4-(4-Methoxyphenyl)butylamine 

Downstream Products

• 409127-82-8 4-(4-(quinolin-4-yl-amino)butyl)phenol 
• 587880-74-8 [4-(4-Benzyloxycarbonylaminobutyl)phenoxy]acetic acid ethyl ester 
• 587880-76-0 (4-{4-[N'-(3,5-Diamino-6-chloropyrazine-2-carbonyl)guanidino]butyl}phenoxy)acetic acid ethyl ester 
• 847201-18-7 [4-(4-cyanomethoxyphenyl)butyl]carbamic acid tert-butyl ester 
• 868077-61-6 N-(3-[4-(3-piperidinopropoxy)phenyl]butyl)-2-amino-5-nitropyridine 
• 868077-51-4 4-(4-[5-nitropyridin-2-yl-amino]butyl)phenol 
• 465529-53-7 tert-butyl (4-(4-hydroxyphenyl)butyl)carbamate 

Relevant articles and documents

COMPOUNDS FOR TREATMENT OF CYSTIC FIBROSIS

Described herein are compounds, compositions, and methods of their use for the treatment of cystic fibrosis.

Search for histamine H3 receptor antagonists with combined inhibitory potency at Nτ-methyltransferase: Ether derivatives

With the recent development of new hybrid compounds having histamine H 3 receptor antagonist with combined histamine Nτ- methyltransferase (HMT) inhibitory potency an innovative approach was described in the research of novel lead compounds modulating histaminergic neurotransmission. Several compounds containing an ether moiety derived from the recently published 4-(3-piperidinopropoxy)phenylaminoquinoline derivatives (like FUB 836), were synthesized in this study and tested for their affinity at cloned human histamine H3 (hH3) receptors and on the inhibition of rat HMT. Besides different heterocycles, e.g. nitro- or amino-substituted pyridines, quinolines, benzothiazole or pyrroline, three classes of compounds were produced: heteroaromatic 3-piperidinopropyl ethers, keto- or imino-substituted 4-(3-piperidinopropyl)phenyl ethers and 4-(3-piperidinopropyl)phenyl ethers with substituted (alkyl)aminopyridines. Whereas the (3-piperidinopropoxy)heterocycles showed only moderate activities on both test models, the 4-(3-piperidinopropoxy)phenyl derivatives were identified as potent histamine H3 receptor ligands and/or HMT inhibitors. Ki values up to 0.42 nM were found for the affinity to the hH 3 receptor. HMT inhibitory potency was identified with IC 50 values about 0.3 μM for the most potent compounds in this series. Comparison of the pyridine-containing derivatives to recently published quinoline analogues showed a decrease in potencies for the pyridines. The dual activity, H3 receptor affinity and HMT inhibition, was moderate to good. For all compounds affinities at hH3 receptors were higher than their inhibitory HMT potencies. The described new histamine H3 receptor antagonists with an ether moiety represent a further promising step in our investigations for a dual activity.

Development of a new class of nonimidazole histamine H3 receptor ligands with combined inhibitory histamine N-methyltransferase activity

In search of novel ways to enhance histaminergic neurotransmission in the central nervous system, a new class of nonimidazole histamine H3 receptor ligands were developed that simultaneously possess strong inhibitory activity on the main histamine metabolizing enzyme, histamine N-methyltransferase (HMT). The novel compounds contain an aminoquinoline moiety, which is an important structural feature for HMT inhibitory activity, connected by different spacers to a piperidino group (for H3 receptor antagonism). Variation of the spacer structure provides two different series of compounds. One series, having only an alkylene spacer between the basic centers, led to highly potent HMT inhibitors with moderate to high affinity at human histamine H3 receptors. The second series possesses a p-phenoxypropyl spacer, which may be extended by another alkylene chain. This latter series also showed strong inhibitory activity on HMT, and in most cases, the H3 receptor affinity even surpassed that of the first series. One of the most potent compounds with this dual mode of action is 4-(4-(3-piperidinopropoxy)phenylamino)quinoline (34) (hH3, Ki = 0.09 nM; HMT, IC50 = 51 nM). This class of compounds showed high antagonist potency and good H3 receptor selectivity in functional assays in guinea pig on H1, H2, and H3 receptors. Because of low or missing in vivo activity of two selected compounds, the proof of concept of these valuable pharmacological tools for the supposed superior overall enhancing effect on histaminergic neurotransmission failed to appear hitherto.

Synthesis and pharmacological characterization of novel 6-fluorochroman derivatives as potential 5-HT(1A) receptor antagonists

A series of novel 6-fluorochroman derivatives was prepared and evaluated as antagonists for the 5-HT(1A) receptor. N-2-[[(6-Fluorochroman-8- yl)oxy]ethyl]-4-(4-methoxyphenyl)butylamine (3; J. Med. Chem. 1997, 40, 1252- 1257) was chosen as a lead, and structural modifications were done on the aliphatic portion of the chroman ring, the tether linking the middle amine and the terminal aromatic ring, the aromatic ring, and lastly the amine. Radioligand binding assays proved that the majority of the novel compounds behaved as good to excellent ligands at the 5-HT(1A) receptor, some of which were selective with respect to α1-adrenergic and D2-dopaminergic receptors. The antagonist activity of the compounds was assessed in the forskolinstimulated adenylate cyclase assays in CHO cells expressing the human 5-HT(1A) receptors. Among the modifications attempted, introduction of an oxo or an optically active hydroxy moiety at the chroman C-4 position was effective in ameliorating the receptor selectivity. Six analogues were selected through the in vitro screens and further evaluated for their in vivo activities. A 4-oxochroman derivative (31n), having a terminal 1,3- benzodioxole ring, demonstrated antagonist activities toward 8-OH-DPAT- induced behavioral and electrophysiological responses in rats.

Use of a dipeptide chemical library in the development of non-peptide tachykinin NK3 receptor selective antagonists

The use of a dipeptide library as the source of a micromolar chemical lead compound for the human tachykinin NK3 receptor is described. The screening of a dipeptide library through a cloned human NK3 receptor binding assay resulted in the identification of Boc(S)Phe(S)PheNH2 (1), which has subsequently been developed, following a 'peptoid' design strategy, into a series of high-affinity NK3 receptor selective antagonists. The structure- activity relationship of the C-terminal portion of this dipeptide lead was first explored and led to the identification of the urea derivative Boc(S)Phe(R)αMePheNH(CH2)7NHCONH2 (41, PD157672). This modified dipeptide has a K(o) of 7 nM in blocking senktide-induced increases in intracellular calcium levels in human NK3 receptors stably expressed in CHO cells. Subsequent optimization of the N-terminal BocPhe group and the αMePhe residue side chain of 41 led to the identification of [S-(R*,S*)]-[2-(2,3- difluorophenyl)-1-methyl-1-[(7-ureidoheptyl)carbamoyl]ethyl]carbamic acid 2- methyl-1-phenylpropyl ester (60, PD161182), a non-peptide NK3 receptor selective antagonist. Compound 60 blocks the senktide-evoked increases in intracellular calcium levels in cloned human NK3 receptors stably expressed in CHO cells with K(e) of 0.9 nM.