[ CAS No. 118-31-0 ]

Name: 118-31-0|Naphthalen-1-ylmethanamine|98%
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Quality Control of [ 118-31-0 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 118-31-0 ]

CAS No. :	118-31-0	MDL No. :	MFCD00004048
Formula :	C₁₁H₁₁N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NVSYANRBXPURRQ-UHFFFAOYSA-N
M.W :	157.21	Pubchem ID :	8355
Synonyms :

Calculated chemistry of [ 118-31-0 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	10
Fraction Csp3 :	0.09
Num. rotatable bonds :	1
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	51.62
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.78
Log Po/w (XLOGP3) :	2.11
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	2.56
Log Po/w (SILICOS-IT) :	2.61
Consensus Log Po/w :	2.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.69
Solubility :	0.318 mg/ml ; 0.00202 mol/l
Class :	Soluble
Log S (Ali) :	-2.29
Solubility :	0.812 mg/ml ; 0.00516 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.11
Solubility :	0.0123 mg/ml ; 0.0000785 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.0

Safety of [ 118-31-0 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 118-31-0 ]

* 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.

Upstream synthesis route of [ 118-31-0 ]
Downstream synthetic route of [ 118-31-0 ]

[ 118-31-0 ] Synthesis Path-Upstream 1~5

1
[ 67-56-1 ]
[ 55210-79-2 ]
[ 118-31-0 ]
[ 16413-71-1 ]
[ 14489-75-9 ]

Reference： [1] Green Chemistry, 2018, vol. 20, # 14, p. 3339 - 3345

2
[ 118-31-0 ]
[ 74-89-5 ]
[ 14489-75-9 ]

Yield	Reaction Conditions	Operation in experiment
85%	at 16 - 45℃; for 40 h;	In the is provided with a stirrer, thermometer, condenser, dropping funnel in the reaction container, adding the mass fraction is 85percent third eyeball 130 ml, methylamine (3) 210 ml, reducing the temperature of the solution to 16 °C, control the stirring speed 130rpm, slowly adding amine methylnaphthalene (2) 0.31mol, dropping time control in 4h, the temperature of the solution elevated to 45 °C, and 36h, evaporate third eyeball, the mass fraction of the residue to 70percent cyclohexane 230 ml, are sequentially used for quality fraction is 35percent potassium sulfite washing solution, sodium bromide solution, phosphorus pentoxide dehydration, 1.8kPa vacuum distillation, collecting 110 - - 115 °C fraction, the mass fraction of the 95percent nitromethane recrystallizing, to obtain crystal N-methyl-1-naphthalene methylamine 45.06g, yield 85percent.

Reference： [1] Patent: CN105503614, 2016, A, . Location in patent: Paragraph 0014; 0015

3
[ 67-56-1 ]
[ 55210-79-2 ]
[ 118-31-0 ]
[ 16413-71-1 ]
[ 14489-75-9 ]

Reference： [1] Green Chemistry, 2018, vol. 20, # 14, p. 3339 - 3345

4
[ 118-31-0 ]
[ 333-27-7 ]
[ 14489-75-9 ]

Reference： [1] Chemical Communications, 2014, vol. 50, # 15, p. 1836 - 1838

5
[ 118-31-0 ]
[ 76391-12-3 ]
[ 13485-59-1 ]

Reference： [1] Patent: US5319098, 1994, A,
[2] Patent: US5424454, 1995, A,

[ 118-31-0 ] Synthesis Path-Downstream 1~68

1
[ 2243-82-5 ]
[ 118-31-0 ]

Reference： [1]Archiv der Pharmazie,1927,vol. 265,p. 411

2
[ 1194-21-4 ]
[ 118-31-0 ]
2-amino-4-<(naphthylmethyl)amino>pyrimidin-6-one [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 1024 - 1031

3
[ 86-86-2 ]
[ 118-31-0 ]

Reference： [1]Chemistry Letters,1989,p. 463 - 464

4
[ 118-31-0 ]
[ 86-53-3 ]

Yield	Reaction Conditions	Operation in experiment
99%	With copper(I) chloride; 4 A molecular sieve; oxygen In pyridine at 60℃; for 24h;
98%	With dmap; copper(l) iodide; 9-azabicyclo[3.3.1]nonane N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; for 15h;
90%	With potassium hydroxide; nickel copper formate; (Bu₄N)₂S₂O₈ In 1,2-dichloro-ethane at 20℃; for 12h;

90%	With 2,2,6,6-tetramethyl-piperidine-N-oxyl; free radical; trichloroisocyanuric acid In dichloromethane at 10℃; for 1.5h;
89%	With sodium hypochlorite In ethanol for 0.25h; Ambient temperature;
89%	With 1-methyl-1H-imidazole; oxygen; copper(ll) bromide In dimethyl sulfoxide at 100℃; for 24h;	1 Typical procedure for CuBr2/NMI catalyzed aerobic oxidation of primary amines General procedure: To a 100 mL eggplant type Schlenk flask were added CuBr2 (67.0 mg, 0.3 mmol), corresponding amine (3 mmol) and a solution of NMI (73.8 mg, 0.9 mmol) in DMSO (6 mL). The flask was evacuated and purged with oxygen for three times before the flask was attached to a balloon filled with oxygen. Then the flask was heated at 100 °C for 24 h. After the flask was cooled down and the reaction mixture turned into green color, water (15 mL) and dichloromethane (15 mL) was added into the mixture. The water layer was extracted with dichloromethane (5 mL x 3) and the organic layers were combined. After removing the solvent, residue was purified by column chromatography (PE/EA = 100:1) to give the product.
83%	With tris(2,2’-bipyridine)dichlororuthenium(II) hexahydrate; oxygen; copper(I) bromide; lithium tert-butoxide In dimethyl sulfoxide at 20℃; for 18h; Schlenk technique; Irradiation;
81%	With pyridine; tert.-butylhydroperoxide; iodine; potassium carbonate In water at 80℃; for 0.0666667h;
79%	With tert.-butylhydroperoxide; ammonium fluoride; iodine; oxygen In water; dimethyl sulfoxide at 70℃; for 2h; Schlenk technique; Sealed tube;
70%	With fluorosulfonyl fluoride; dihydrogen peroxide; caesium carbonate In ethanol; water at 20℃; for 3h;	General procedure: In this case, optimized reaction conditions are a littlebit different from those for the oxidation of anilines: 30% H2O2(6.0 equiv), Cs2CO3 (10.0 equiv), SO2F2 (balloon), EtOH/H2O = 3/1(v/v), room temperature for 3 h.
	With pyridine; copper(l) iodide; oxygen at 60℃; for 24h; mol. sieves; Yield given;
	Multi-step reaction with 2 steps 1: dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen / toluene / 12 h / 110 °C / 760.05 Torr / Sealed tube 2: dichloro[1,3-bis(2-methylphenyl)-2-imidazolidinylidene](benzylidene) (tricyclohexylphosphine) ruthenium(II); oxygen; ammonium acetate / 5,5-dimethyl-1,3-cyclohexadiene / 1 h / 130 °C / 760.05 Torr / Sealed tube
99 %Chromat.	With C₆₈H₆₄Cl₂N₆P₂Ru₂⁽⁴⁺⁾2F₆P^(1-)2Cl^(1-); caesium carbonate In N,N-dimethyl-formamide at 100℃; for 24h; Inert atmosphere; Green chemistry;
	With sodium periodate; C₃₁H₂₉Br₂N₃Ru In water; ethyl acetate at 80℃; for 24h;

Reference： [1]Capdevielle, Patrice; Lavigne, Andre; Maumy, Michel [Synthesis, 1989, # 6, p. 453 - 454]
[2]Kim, Jinho; Stahl, Shannon S. [ACS Catalysis, 2013, vol. 3, # 7, p. 1652 - 1656]
[3]Chen, Fen-Er; Peng, Zuo-Zhong; Fu, Han; Liu, Ji-Dong; Shao, Lan-Ying [Journal of Chemical Research - Part S, 1999, # 12, p. 726 - 727]
[4]Chen, Fen-Er; Kuang, Yun-Yan; Dai, Hui-Fang; Lu, Liang; Huo, Ming [Synthesis, 2003, # 17, p. 2629 - 2631]
[5]Yamazaki, Shigekazu [Synthetic Communications, 1997, vol. 27, # 20, p. 3559 - 3564]
[6]Shen, Yifan; Zhou, Yu; Jiang, Lili; Ding, Guangni; Luo, Luo; Zhang, Zhaoguo; Xie, Xiaomin [Tetrahedron, 2018, vol. 74, # 31, p. 4266 - 4271]
[7]Tao, Chuanzhou; Wang, Bin; Sun, Lei; Liu, Zhou; Zhai, Yadong; Zhang, Xiulian; Wang, Jian [Organic and Biomolecular Chemistry, 2017, vol. 15, # 2, p. 328 - 332]
[8]Location in patent: scheme or table Zhang, Jintang; Wang, Zhentao; Wang, Ye; Wan, Changfeng; Zheng, Xiaoqi; Wang, Zhiyong [Green Chemistry, 2009, vol. 11, # 12, p. 1973 - 1978]
[9]Guo, Songjin; Wan, Gen; Sun, Song; Jiang, Yan; Yu, Jin-Tao; Cheng, Jiang [Chemical Communications, 2015, vol. 51, # 24, p. 5085 - 5088]
[10]Liao, Xudong; Zhou, Yi; Ai, Chengmei; Ye, Cuijiao; Chen, Guanghui; Yan, Zhaohua; Lin, Sen [Tetrahedron Letters, 2021, vol. 84]
[11]Capdevielle; Lavigne; Sparfel; Baranne-Lafont; Cuong; Maumy [Tetrahedron Letters, 1990, vol. 31, # 23, p. 3305 - 3308]
[12]Utsumi, Tatsuki; Noda, Kenta; Kawauchi, Daichi; Ueda, Hirofumi; Tokuyama, Hidetoshi [Advanced Synthesis and Catalysis, 2020, vol. 362, # 17, p. 3583 - 3588]
[13]Chen, Hua; Fu, Haiyan; Ji, Li; Li, Ruixiang; Nie, Xufeng; Zheng, Yanling [Journal of Catalysis, 2020, vol. 391, p. 378 - 385]
[14]Bera, Jitendra K.; Din Reshi, Noor U; Pal, Nilay Kumar; Pal, Saikat; Pal, Sourav; Yadav, Suman [Applied Organometallic Chemistry, 2022]

5
[ 118-31-0 ]
[ 21286-54-4 ]
C-((1R,2S,4S)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-yl)-N-naphthalen-1-ylmethyl-methanesulfonamide [ No CAS ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 5651 - 5666
[2]Tetrahedron,1998,vol. 54,p. 5651 - 5666

6
[ 118-31-0 ]
[ 14527-26-5 ]
1-(1-naphthylmethyl)guanidinium sulfate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1999,vol. 42,p. 3101 - 3108

7
[ 10009-70-8 ]
[ 118-31-0 ]
[ 110990-08-4 ]
[ 183056-94-2 ]
S-acetyl 2-mercapto-2-methyl propionamide-derivatized polystyrene resin [ No CAS ]
(R)-6-Amino-2-((R)-2-bromo-propionylamino)-hexanoic acid (2-mercapto-ethyl)-naphthalen-1-ylmethyl-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 1817 - 1825

8
[ 118-31-0 ]
[ 110990-08-4 ]
[ 183056-94-2 ]
2-bromo-3-(1H-indol-3-yl)-propionic acid [ No CAS ]
S-acetyl 2-mercapto-2-methyl propionamide-derivatized polystyrene resin [ No CAS ]
(R)-6-Amino-2-[(S)-2-bromo-3-(1H-indol-3-yl)-propionylamino]-hexanoic acid (2-mercapto-ethyl)-naphthalen-1-ylmethyl-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 1817 - 1825

9
[ 118-31-0 ]
[ 110990-08-4 ]
[ 183056-94-2 ]
2-bromo-3-(1H-indol-3-yl)-propionic acid [ No CAS ]
S-acetyl 2-mercapto-2-methyl propionamide-derivatized polystyrene resin [ No CAS ]
(R)-6-Amino-2-[(R)-2-bromo-3-(1H-indol-3-yl)-propionylamino]-hexanoic acid (2-mercapto-ethyl)-naphthalen-1-ylmethyl-amide [ No CAS ]

Reference： [1]Journal of the American Chemical Society,1999,vol. 121,p. 1817 - 1825

10
[ 4780-79-4 ]
[ 118-31-0 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: 1-naphthalene methanol With resin-bound CH₂OCONHCOOtBu; diethylazodicarboxylate In tetrahydrofuran for 12h; Stage #2: With trifluoroacetic acid In 1,2-dichloro-ethane for 4h;
59%	With potassium <i>tert</i>-butylate; ammonia In toluene at 150℃; for 24h;
	Multi-step reaction with 2 steps 1: 2.7 g / PPh₃; DEAD / tetrahydrofuran / 22 h / 0 - 20 °C 2: NaBH₄; AcOH / propan-1-ol; H₂O / 5 h / 80 - 90 °C

	Multi-step reaction with 2 steps 1: acetic acid; hydrogen bromide / 0.5 h / 0 °C 2: ammonia / ethanol; water / 4 h / 20 °C
	Multi-step reaction with 2 steps 1: hydrogen bromide / acetic acid / 0.5 h / 0 °C 2: ammonium hydroxide / ethanol / 4 h / 20 °C

Reference： [1]Subramanyam [Tetrahedron Letters, 2000, vol. 41, # 34, p. 6537 - 6540]
[2]Beller, Matthias; Gawande, Manoj B.; Jagadeesh, Rajenahally V.; Kadam, Ravishankar G.; Li, Xinmin; Ma, Zhuang; Petr, Martin; Zbořil, Radek; Zhou, Bei [Chemical Science, 2022, vol. 13, # 1, p. 111 - 117]
[3]Walker, Joel R; Curley Jr., Robert W [Tetrahedron, 2001, vol. 57, # 31, p. 6695 - 6701]
[4]Kiruthika, Selvarangam E.; Perumal, Paramasivan Thirumalai [Organic Letters, 2014, vol. 16, # 2, p. 484 - 487]
[5]Kiruthika, Selvarangam E.; Nandakumar, Avanashiappan; Perumal, Paramasivan Thirumalai [Organic Letters, 2014, vol. 16, # 17, p. 4424 - 4427]

11
[ 6404-26-8 ]
[ 118-31-0 ]
N-(1-naphthylmethyl)-N-α-(tert-butyloxycarbonyl)-N-ω-acetyl-lysinamide [ No CAS ]

Reference： [1]Pharmazie,2000,vol. 55,p. 601 - 606

12
[ 2004-07-1 ]
[ 118-31-0 ]
2-amino-N⁶-(1''-naphthylmethyl)adenosine [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 4135 - 4150

13
[ 57476-50-3 ]
[ 118-31-0 ]
3-[(naphthalen-1-ylmethylimino)-methyl]-indole-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1035 - 1038

14
[ 104-03-0 ]
[ 118-31-0 ]
[ 101555-63-9 ]
[ 18637-83-7 ]
N-naphthalen-1-ylmethyl-2-[4-(1,3,4-trioxo-octahydro-pyrido[1,2-a]pyrazin-2-yl)-phenyl]-acetamide [ No CAS ]