| Identification | Back Directory | [Name]
5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylamine | [CAS]
92050-16-3 | [Synonyms]
Tamibarotene Impurity 1
5,5,8,8-TetraMethyl-6,7-dihydronaphthalen-2-aMine
5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine
5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine
2-Amino-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalene
2-Naphthalenamine,5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-
5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylamine
5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-ylamine ISO 9001：2015 REACH
2-aMino-5,5,8,8-tetraMethyl-5,6,7,8-tetrahydronaphthalene, 2-aMino-5,6,7,8-tetrahydro-5,5,8,8-tetraMethylnaphthalene | [Molecular Formula]
C14H21N | [MDL Number]
MFCD12828202 | [MOL File]
92050-16-3.mol | [Molecular Weight]
203.327 |
| Chemical Properties | Back Directory | [Melting point ]
63-65℃ | [Boiling point ]
310.2±31.0 °C(Predicted) | [density ]
0.944 | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [pka]
5.16±0.60(Predicted) | [Appearance]
Off-white to light brown Solid | [InChI]
InChI=1S/C14H21N/c1-13(2)7-8-14(3,4)12-9-10(15)5-6-11(12)13/h5-6,9H,7-8,15H2,1-4H3 | [InChIKey]
AMDKYPNODLTUMY-UHFFFAOYSA-N | [SMILES]
C1=C2C(C(C)(C)CCC2(C)C)=CC=C1N |
| Hazard Information | Back Directory | [Synthesis]
General procedure for the synthesis of 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (74) from 2-nitro-5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (73): 1,1,4,4-tetramethyl-6-nitro-1,2,3,4-tetrahydronaphthalene (73) (2.5 g, 10.7 mmol) was dissolved in ethyl acetate (210 mL) in ethyl acetate using 10% Pd/C as a catalyst, and the hydrogenation reaction was repeated twice at a flow rate of 1.0 mL/min in a ThalesNano H-Cube?reactor at 70°C and 2-5 bar hydrogen pressure. Upon completion of the reaction, the reaction solution was concentrated in vacuum to afford a yellow crystalline solid 5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine (74) (2.1532 g, 99% yield), with a melting point of 205°C. The product was characterized as follows: 1H NMR (400 MHz, CDCl3) δ 7.11 (d, J = 8.4 Hz, 1H), 6.65 (d, J = 2.4 Hz, 1H), 6.54 (dd, J = 8.4, 2.4 Hz, 1H), 3.62 (br s, 2H), 1.66 (s, 4H), 1.26 (s, 6H), 1.25 (s, 6H); 13C NMR (100.6 MHz, CDCl3) δ 145.8, 143.3, 135.4, 127.3, 113.7, 112.9, 35.2, 34.1, 33.5, 31.9, 31.7; IR (neat) 3405, 3208, 2952, 2920, 1612, 1499 cm-1; LC-MS (CI) m/z (M+H)+ Calculated C14H22N 204.1752, Measured C14H22N 204.1752. 204.1747. | [References]
[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 9, p. 2352 - 2356
[2] Patent: WO2015/130973, 2015, A1. Location in patent: Page/Page column 34; 35
[3] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8924 - 8940
[4] Patent: US2018/207156, 2018, A1. Location in patent: Paragraph 0114; 0119
[5] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 15, p. 7277 - 7290 |
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