17768-41-1

Basic information

• Product Name: 1-Adamantanemethylamine
• Synonyms: 1-Adamantylmethanamine;Tricyclo[3.3.1.1(3,7)-]decane-1-methanamine;1-ADMA;1-ADAMANTYLMETHYLAMINE;1-AMINOMETHYLADAMANTANE;AKOS BC-0196;AKOS B014406;tricyclo(3.3.1.13,7)dec-1-ylmethylamine
• CAS NO: 17768-41-1
• Molecular Formula: C₁₁H₁₉N
• Molecular Weight: 165.28
• EINECS: 241-752-1
• Product Categories: Adamantane derivatives;Adamantanes
• Mol File: 17768-41-1.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 83-85 °C0.3 mm Hg(lit.)
• Flash Point: 198 °F
• Appearance: Colorless to pale yellow/Liquid
• Density: 0.933 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0697mmHg at 25°C
• Refractive Index: n20/D 1.5137(lit.)
• Storage Temp.: 2-8°C(protect from light)
• PKA: 10.71±0.29(Predicted)
• Sensitive: Air Sensitive
• CAS DataBase Reference: 1-Adamantanemethylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Adamantanemethylamine(17768-41-1)
• EPA Substance Registry System: 1-Adamantanemethylamine(17768-41-1)

Safety Data

• Hazard Codes: Xi,C
• Statements: 34
• Safety Statements: 24/25-45-36/37/39-27-26
• RIDADR: UN 2735
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 17768-41-1(Hazardous Substances Data)

Usage

Chemical Properties

clear colourless to very slightly yellow liquid

General Description

1-Adamantanemethylamine is a large amine present on the wall of 6,7-diaminoquinoxaline. The thermodynamic complex formation constant of 1-adamantanemethylamine was studied.

Purification Methods

Dissolve the amine in Et2O, dry over KOH and distil it. The N-Tosyl derivative has m 134-135o (from EtOH). [Stetter & Goebel Chem Ber 96 550 1963.]

InChI:InChI=1/C11H19N/c12-7-11-4-8-1-9(5-11)3-10(2-8)6-11/h8-10H,1-7,12H2/p+1

Upstream product

• 23074-42-2 1-adamantanecarbonitrile 
• 313231-15-1 N-(adamantan-1-ylmethyl)phthalimide 
• 768-95-6 1-adamanthanol 
• 2094-72-6 1-Adamantanecarbonyl chloride 
• 123933-30-2 O-methyl adamantane-1-carbothioate 
• 711-01-3 methyl adamantane-1-carboxylate 
• 828-51-3 1-Adamantanecarboxylic acid 
• 170952-87-1 N-hydroxyiminomethyl 1-adamantanecarboxylate 
• 4942-47-6 (adamant-1-yl)-acetic acid 
• 5511-18-2 adamantane-1-carboxamide 
• 768-90-1 1-Adamantyl bromide 

Downstream Products

• 100025-85-2 N'-<4-Aethyl-benzolsulfonyl>-N--harnstoff 
• 99831-60-4 N'-<4-Acetyl-benzolsulfonyl>-N--harnstoff 
• 14504-80-4 3-Hydroxyhomoadamantan 
• 89661-86-9 [(S)-1-{(R)-1-[(S)-1-({[(Adamantan-1-ylmethyl)-carbamoyl]-methyl}-carbamoyl)-2-phenyl-ethylcarbamoyl]-ethylcarbamoyl}-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 1027664-33-0 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzofuran-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid diallyl ester 
• 1026292-72-7 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-benzo[b]thiophene-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid di-tert-butyl ester 
• 338450-87-6 5-[(S)-2-({5-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-6-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester 
• 167992-88-3 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-isophthalic acid dibenzyl ester 
• 1026556-36-4 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-(2-fluoro-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 1027934-40-2 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-benzoimidazole-5-carbonyl}-amino)-3-(4-hydroxy-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 1026318-99-9 5-[(S)-2-({6-[(Adamantan-1-ylmethyl)-carbamoyl]-1H-benzoimidazole-5-carbonyl}-amino)-3-(2-fluoro-phenyl)-propionylamino]-isophthalic acid dibenzyl ester 
• 1026901-39-2 2,2-Dimethyl-propionic acid 5-{3-[(S)-2-({6-[(adamantan-1-ylmethyl)-carbamoyl]-1H-indole-5-carbonyl}-amino)-3-phenyl-propionylamino]-5-[1-(2,2-dimethyl-propionyloxymethyl)-1H-tetrazol-5-yl]-phenyl}-tetrazol-1-ylmethyl ester 
• 167992-94-1 2,2-Dimethyl-propionic acid 5-{3-[(S)-2-({6-[(adamantan-1-ylmethyl)-carbamoyl]-1H-benzoimidazole-5-carbonyl}-amino)-3-phenyl-propionylamino]-5-[1-(2,2-dimethyl-propionyloxymethyl)-1H-tetrazol-5-yl]-phenyl}-tetrazol-1-ylmethyl ester 

Relevant articles and documents

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In order to systematically explore and better understand the structure-activity relationship (SAR) of a diarylmethane backbone in the design of potent uric acid transporter 1 (URAT1) inhibitors, 33 compounds (1a-1x and 1ha-1hi) were designed and synthesized, and their in vitro URAT1 inhibitory activities (IC50) were determined. The three-round systematic SAR exploration led to the discovery of a highly potent novel URAT1 inhibitor, 1h, which was 200-and 8-fold more potent than parent lesinurad and benzbromarone, respectively (IC50 = 0.035 μM against human URAT1 for 1h vs. 7.18 μM and 0.28 μM for lesinurad and benzbromarone, respectively). Compound 1h is the most potent URAT1 inhibitor discovered in our laboratories so far and also comparable to the most potent ones currently under development in clinical trials. The present study demonstrates that the diarylmethane backbone represents a very promising molecular scaffold for the design of potent URAT1 inhibitors.