[ CAS No. 112-90-3 ]

Name: 112-90-3|(Z)-Octadec-9-en-1-amine|70%
Brand: Ambeed
SKU: A778776
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Quality Control of [ 112-90-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 112-90-3 ]

CAS No. :	112-90-3	MDL No. :	MFCD00066507
Formula :	C₁₈H₃₇N	Boiling Point :	364.4°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	267.49 g/mol	Pubchem ID :	-
Synonyms :	1. Oleylamine

Calculated chemistry of of [ 112-90-3 ]

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.89
Num. rotatable bonds :	15
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	90.87
TPSA :	26.02 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.54 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.75
Log Po/w (XLOGP3) :	3.37
Log Po/w (WLOGP) :	5.98
Log Po/w (MLOGP) :	4.79
Log Po/w (SILICOS-IT) :	6.12
Consensus Log Po/w :	5.0

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.63
Solubility :	0.625 mg/ml ; 0.00234 mol/l
Class :	Soluble
Log S (Ali) :	-3.59
Solubility :	0.068 mg/ml ; 0.000254 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-6.07
Solubility :	0.000227 mg/ml ; 0.000000849 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.17

Safety of [ 112-90-3 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P273-P280-P305+P351+P338-P310	UN#:	2735
Hazard Statements:	H302-H314-H412	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 112-90-3 ]

* 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 [ 112-90-3 ]
Downstream synthetic route of [ 112-90-3 ]

[ 112-90-3 ] Synthesis Path-Upstream 1~2

1
[ 112-90-3 ]
[ 10010-93-2 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 46, p. 14737 - 14742[2] Angew. Chem., 2017, vol. 129, # 46, p. 14932 - 14937,6

2
[ 112-90-3 ]
[ 20154-03-4 ]

Reference： [1] Angewandte Chemie - International Edition, 2017, vol. 56, # 46, p. 14737 - 14742[2] Angew. Chem., 2017, vol. 129, # 46, p. 14932 - 14937,6

[ 112-90-3 ] Synthesis Path-Downstream 1~32

1
[ 112-90-3 ]
[ 112-80-1 ]
(9Z)-N-[(9Z)-9-octadecen-1-yl]-9-octadecenamide [ No CAS ]

Reference： [1]Green Chemistry,2018,vol. 20,p. 375 - 381
[2]Journal of the American Chemical Society,2006,vol. 128,p. 16522 - 16523

2
[ 112-90-3 ]
[ 10305-42-7 ]
N-oleyl-N'-propylsulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
58%	With triethylamine; In toluene; at 0 - 20℃;	Example 6 - Preparation of lambdaHcis-g-octadecenvD-N'-propylsulfamide, also known as N- oleyl-N'-propylsulfamiotade (6)0 20 g (1 2 mmol) of freshly distilled lambda/-propylsulfamoyl chloride were added dropwise to a solution of the amine and TEA in dry toluene at 0 0C under nitrogen atmosphere The reaction mixture was stirred at room temperature, and the white solid(TEA HCI) was filtered, the solvent was evaporated to dryness and the crude was purified by column chromatography on silica gel with CH2CI2 MeOH/NH3 9 1 , providing the desired product (0 27g) as a white solid Yield 58%, m p 82-83C1H NMR (400 MHz, CDCI3) delta 5 30 (m, 2H, CH=CH), 4 25 (br s, 2H, NH), 2 97 (m, 4H, CH2NHSO2NHCH2), 1 97 (m, 4H, CH2CH=CHCH2), 1 54 (sextet, 2H, J = 7 3 Hz, CH2- <n="19"/>CH3 (Pr)); 1.51 (m, 2H, CH2CH2NHSO2); 1.21 (bm, 22H1 -CH2-); 0.91 (t, 3H, J = 7.3 Hz1 CH2-CH3(Pr)); 0.84 (t, 3H1 J = 6.6 Hz, CH2-CH3 (oleyl)).13C NMR (100 MHz1 CDCI3) delta: 129.9, 129.7 (CH=CH); 44.9 (NHSO2NHCH2 (Pr)); 43.2 (oleyl-CH2NHSO2); 31.8 (CH2-CH2CH3); 29.8-28.9, 26.7 (-CH2-); 27.1 , (CH2-CH=CH- CH2); 22.8 (CH2-CH3 (Pr)); 22.6 (CH2-CH3 (oleyl)); 14.1 (CH3 (oleyl)); 1 1.2 (CH3(Pr)). Anal (C21H44N2SO2) % theor. (% found): C: 64.86 (65.06); H: 11.32 (11.60); N: 7.20 (7.34); S: 8.23 (8.33).

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 389 - 393
[2]Patent: WO2007/85469,2007,A1 .Location in patent: Page/Page column 17-18

3
[ 112-90-3 ]
N-oleylsulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With SULFAMIDE; In ethanol; water; for 6.5h;Heating / reflux;	Example 1 - Preparation of lambda/-(cis-9-octadecenyl)sulfamide (1 ), also known as N- oleylsulfamide.To a stirred solution of 0.20 g of sulfamide (2.1 mmol) in 20 ml of H2O under reflux it is added dropwise 0.1 ml (2.1 mmol) of lambda/-oleylamine in 10 ml of EtOH for 30 minutes. The reaction mixture is stirred and refluxed for 6 hours. Then the solvent is evaporated and the white solid is purified in a chromatography column, using CH2CI2:MeOH/NH39.4:0.6 as eluyent; 0.52 g of white solid are obtained. Yield 72%; mp = 68-70 C; 1H NMR (300 MHz, CDCI3) : 5.32 (m, 2H); 4.59 (br s, 2H); 4.38 (br s, 1 H); 3.09 (q, J = 7.0 Hz, 2H); 1.97 (m, 4H); 1.55 (m, 2H); 1.24 (m, 22H); 0.85 (t, J = 6.7 Hz, 3H). 13C NMR (75 MHz, CDCI3) : 129.9; 129.7; 43.6; 31.8; 29.7-26.6; 27.1 ; 27.2; 22.6; 14.1. MS (ES+) [M+HJ+ 347 (100%). Anal. (C18H38N2SO2, 346.57): C, H, N, S.

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 389 - 393
[2]Patent: WO2007/85469,2007,A1 .Location in patent: Page/Page column 16

4
[ 112-90-3 ]
[ 112-82-3 ]
[ 52986-14-8 ]

Yield	Reaction Conditions	Operation in experiment
83%	With sodium hydroxide; In methanol; dichloromethane; chloroform;	1-bromohexadecane (15.27 g, 50 mmol) was rapidly added to oleylamine (26.75 g, 100 mmol) at 100 C. The reaction mixture was heated at 120 C. for 30 minutes and than cooled to room temperature. Chloroform(200 ml) was added followed by 1 N NaOH (50 ml). The mixture was then extracted with H2O (200 ml), the organic layer dried (Na2SO4) and concentrated to a syrup. Silica gel column chromatography using 5-20% gradient methanol in dichloromethane afforded 20.5 g of palmityloleylamine as a syrup (yield, 83%). The identity of the product was confirmed using NMR spectroscopy. 1H NMR (CDCl3) d 5.34 (m, 2H, CH=CH), 2.58 (m, 4H), 2.00 (m, 4H), 1.47 (m, 4H), 1.25 (m, 48H), 0.86 (m, 6H). FAB-MS: 493 [M+H]+. (Other reagents could include oleyl-bromide and hexadecane amine)
83%	With sodium hydroxide; In methanol; dichloromethane; chloroform;	Synthesis of palmityloleylamine (1) 1-bromohexadecane (15.27 g, 50 mmol) was rapidly added to oleylamine (26.75 g, 100 mmol) at 100 C. The reaction mixture was heated at 120 C. for 30 minutes and than cooled to room temperature. Chloroform(200 ml) was added followed by 1 N NaOH (50 ml). The mixture was then extracted with H2O (200 ml), the organic layer dried (Na2SO4) and concentrated to a syrup. Silica gel column chromatography using 5-20% gradient methanol in dichloromethane afforded 20.5 g of palmityloleylamine as a syrup (yield, 83%). The identity of the product was confirmed using NMR spectroscopy. 1H NMR (CDCl3) d 5.34 (m, 2H, CH=CH), 2.58 (m, 4H), 2.00 (m, 4H), 1.47 (m, 4H), 1.25 (m, 48H), 0.86 (m, 6H). FAB-MS: 493 [M+H]+. (Other reagents could include oleyl-bromide and hexadecane amine)
83%	at 100 - 120℃; for 0.5h;	N-oleyl-palmityl amine is an important starting material for the compounds according to the present invention. The N-oleyl-palmityl amine can, in principle, be synthesised as described in US 6,395,713. The respective reaction scheme is depicted in Fig. 2. However, the starting material is oleyl amine of technical grade as provided by, e. g., Fluka. An analysis of this starting material by gas chromatography shows a purity of > 70 %, whereby 30 % of the material consist of amine having different chain lengths. The reason for this could be that the material as such is obtained from plant sources. Combining both oleyl amine and 1-bromohexadecane (palmitylbromid) yields N-oleyl-palmityl amine after reacting both starting materials at 100 to 120 C for 30 minutes. The yield is about 83 %.

83%

at 100 - 120℃; for 0.5h;Product distribution / selectivity;

N-oleyl-palmityl amine is an important starting material for the compounds according to the present invention. The N-oleyl-palmityl amine can, in principle, be synthesised as described in US 6,395,713. The respective reaction scheme is depicted in Fig. 2. However, the starting material is oleyl amine of technical grade as provided by, e. g. , Fluka. An analysis of this starting material by gas chromatography shows a purity of No. 70 %, whereby 30 % of the material consist of amine having different chain lengths. The reason for this could be that the material as such is obtained from plant sources. Combining both oleyl amine and 1-bromohexadecane (palmitylbromid) yields N-oleyl-palmityl amine after reacting both starting materials at 100 to 120 C for 30 minutes. The yield is about 83 %.

Reference： [1]Patent: US2003/73640,2003,A1
[2]Patent: US6395713,2002,B1
[3]Patent: WO2006/69782,2006,A2 .Location in patent: Page/Page column 26
[4]Patent: WO2005/105152,2005,A2 .Location in patent: Page/Page column 27; figure 2

5
C₁₆H₁₄O₇ [ No CAS ]
[ 112-90-3 ]
2-(3,4-dihydroxy-phenyl)-N-heptadec-8-enyl-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In hexane; ethyl acetate; at -20℃; for 193h;	Preparation of 2-(3,4-dihydroxy-phenyl)-N-heptadec-8-enyl-acetamideOverview: Dihydroxyphenylacetic acid was first converted to its anhydride in the presence of DDC (dicyclohexyl carbodiimide). The resulting intermediate was then reacted with oleylamine in the presence of 4-dimethylaminopyridine in DMF.1.5 g of 2,4-dihydroxyphenylacetic acid (1.8 mole) was dissolved in 20 niL of 50:50 v/v ethyl acetate and hexane. Then 1.5 mL of DCC (-1.4 mmole) was added and the reaction continued for 1 hr at room temperature under argon that was bubbled into the solution. A white precipitate of dicyclohexyl urea formed during the reaction. After 3 hr, the urea precipitate was removed and 1.8 mL (5.6 mmol) of oleylamine (C18-content 80-90%; Fisher), was initially dissolved in 10 mL of hexane in the presence of 4-dimethylaminopyridine (0.5 g) and added to the reaction product of the 2,4-dihydroxyphenylacetic acid and DCC. The reaction continued at room temperature for 1 hr and then stored at -20 0C for one week.The resulting mixture was extracted with water followed by 2x with 5 M NaCl and dried under argon. The white pellet was dissolved in 10 mL of CHCl3/MeOH (18:1) and the product isolated by chromatography (silica gel/hexane). 1H NMR data in CD3Cl is provided in Figure 6A.

Reference： [1]Patent: WO2006/86422,2006,A2 .Location in patent: Page/Page column 45

6
[ 112-90-3 ]
[ 96-24-2 ]
3-oleyldithiocarbamoyl-1,2-propanediol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
73%	With sodium hydroxide; In CS2; hexane; water;	Thus, CS2 (6.0 ml) was reacted with oleylamine (33.44 grams; 80% pure) in hexane (25 ml), followed by the addition of aqueous NaOH (4.0 grams in 40 ml H2 O) and 3-chloro-1,2-propanediol (11.05 grams). After an aqueous work up, the reaction product obtained was found to be contaminated with a small amount of N-oleylisothiocyanate which was easily separated from the desired diol by column chromatography and elution with 60% ethyl acetate in hexane. The isolated grey waxy 3-oleyldithiocarbamoyl-1,2-propanediol (30.48 grams; 73% yield) was then borated with boric acid (2.26 grams) by the procedure described in Example II above to give the desired compound as a yellow viscous liquid.

Reference： [1]Patent: US5672727,1997,A

7
[ 112-90-3 ]
[ 14227-17-9 ]
[ 135627-22-4 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 7 (Z)-2-(9-Octadecenylamino)-N-(2,4,6-trimethoxyphenyl)acetamide The title compound was prepared according to the procedure for Example 1 by substituting oleyl amine for benzhydryl amine and <strong>[14227-17-9]2,4,6-<strong>[14227-17-9]trimethoxy aniline</strong></strong> for 2,6-diisopropyl aniline. 11.45 g (58%). NMR (CDCl3) delta 0.88 (3H, t), delta 1.2-1.52 (24H, m), delta 2.01 (4H, m), delta 2.71 (2H, t), delta 3.42 (2H, m), delta 3.68 (3H, s), delta 3.79 (6H, s), delta 5.33 (2H, m), delta 6.13, (2H, d), delta 8.31 (1H, bs) IR (film) 3310, 3003, 2928, 1669, 1346, 1062, 954, 811 cm-1.

Reference： [1]Patent: US5153226,1992,A

8
[ 112-90-3 ]
[ 41130-29-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In tert-butyl methyl ether; at 20 - 30℃; for 0.75 - 1h;	To the stirred crude amine solution in TBME (~90 L) pf step 1.3, 6.7 Kg (1.2 eq) (+/-2%) of concentrated (37%) hydrochloric acid are added via dosing pump, over 15-30 minutes, at a temperature of 20-30C (exothermic addition). Approximate volume is 95 L. The clear monophasic solution is stirred for at least 30 minutes at 20-30 C and acetonitrile (225.0 L, 176.85 Kg) (+/-5 %) is charged to the paired reactor. The hydrochloride salt solution is charged to the acetonitrile over 30-60 minutes to form a white precipitate. Approximate volume is 320 L. The precipitate is cooled to 0-6C, hold for at least 1 hour and filtered. The cake volume is about 90 L. The precipitate is washed with 2 x 35 L of chilled acetonitrile and the solid is dried at 25-30C to constant weight (DSC performed). The dried solid is transferred back into the reactor and 10 weight volumes (-135 L, 100 Kg) of TBME are added. The reaction medium is stirred until a solution is obtained. Approximate volume is 150 L. 2 equivalents (~50.5 L) of 2M sodium hydroxide solution in water are added over 15-30 minutes at 15-25C (addition is slightly endothermic). Approximate volume is 200 L and the biphasic mixture is stirred for at least 1 hour at 15-25C and allows separating. The lower aqueous layer is removed and discarded. The organic solution is washed with water (2 x 35L), azeo-dried by distillation at atmospheric (b.p. TBME 58C) and then concentrated to dryness under full house vacuum until residual levels of TBME are within ICH guidelines by headspace GC.

Reference： [1]Patent: EP1746084,2007,A1 .Location in patent: Page/Page column 4-5
[2]Angewandte Chemie - International Edition,2017,vol. 56,p. 8746 - 8750
Angew. Chem.,2017,vol. 129,p. 8872 - 8876,5

9
[ 112-90-3 ]
N-oleylsulfamide [ No CAS ]
N,N'-dioleylsulfamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
22%	With SULFAMIDE; In water; at 20℃; for 48h;Heating / reflux;	Example 13 - Preparation of lambda/,A/'-bis(9-cis-octadecenyl)sulfamide, also known as N, N'- dioleylsulfamide (13).0.68 ml of N-oleylamine (1.4 mmol) are added dropwise to 0.20 g of N- propylsulfamide (1.4 mmol) in 2 ml of water at room temperature. The colourless mixture reaction is stirred under reflux for 48 h, showing an orange colour. The solvent is evaporated and the crude is purified in a chromatography column, using CH2CI2 as eluyent. 0.12 g of white solid (compound 1 ) and 0.26 g of white solid (compound 13) were obtained. Yield (compound 13): 22%; m.p. 85-880C.1H-NMR (400 MHz, CDCI3) delta: 5.32 (m, 4H, CH=CH); 4.25 (bs, 2H, NH); 3.00 (m, 8H,CH2NHSO2); 1.99 (m, 8H, CH2-CH=CH-CH2); 1.53 (sextet, J = 7.3 Hz, 4H, CH2CH3); 1.26 (bm, 44H); 0.87 (t, 3H, J = 7.3 Hz, CH3).13C-NMR (100 MHz, CDCI3) delta: 129.9, 129.7 (CH=CH;; 43.2 (CH2NHSO2); 31.9 (CH2-CH2CH3); 29.7, 29.6, 29.5, 29.4, 29.3, 29.2, 27.2, 26.7 (-CH2); 22.6 (CH2-CH3); 14.0(CH3)

Reference： [1]Patent: WO2007/85469,2007,A1 .Location in patent: Page/Page column 20

10
[ 112-90-3 ]
[ 814-68-6 ]
[ 23586-43-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	With triethylamine; In dichloromethane; at -10 - 0℃; for 4.33333h;	To a solution of oleylamine 78 (26.75 g, 100 mmol) and triethylamine (20 g, 200 mmol) in anhydrous CH2Cl2 (200 mL) at -10 C, a solution of acryloyl chloride (9.9 g, 110 mmol) in CH2Cl2 (100 mL) was added dropwise over a period of 20 min. After the completion of the addition the reaction mixture was stirred for 4 h at 0 C after which the TLC of the reaction mixture showed the completion of the reaction. The reaction mixture was washed with satd. NaHCO3 solution (200 mL), water (200 mL), brine (100 mL) and dried over NaSO4. Concentration of the organic layer provided the product 79 (32 g, 100%) which was used as such in the next step. 1H NMR CDCl3 delta 0.91 (t, J = 6.5Hz, 3H), 1.05-1.35 (m, <n="128"/>24H), 1.42 (t, 2H), 1.96 (m, 4H), 5.31 (t, 1H), 5.33-5.36 (m, 1H), 5.54 (dd, 1H), 6.02 (dd, 1H), 6.18 (dd, 1H), 8.03 (bs, 1H).
	With triethylamine; In dichloromethane;	Example 2Acryloylamido alkane or alkenes: Oleylamine was treated with acryloyl chloride in the presence of TEA in CH2Cl2. After routine work up, the resulted acryloylamido-olean was purified by chromatograph on silica gel (Hexane: ethyl acetate 10:90).

Reference： [1]Patent: WO2008/42973,2008,A2 .Location in patent: Page/Page column 126-127
[2]Patent: WO2008/137470,2008,A1 .Location in patent: Page/Page column 8

11
[ 112-90-3 ]
[ 13076-17-0 ]
[ 1186629-30-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	In N,N-dimethyl-formamide; at 80℃; for 34h;	(300mg, 2.08mmol) L-Lactide was added to a solution of (1.6g, 4.16mmol) of oleyl amine in 10ml DMF. The reaction mixture was heated to 80 0C for (34 hrs). Thorough out this period of time the color turned from colorless to yellow. Reaction was followed by TLC (100% Eth. Ac). When reaction was over, the product was obtained by column chromatography (CHC13/Hexane = 20:80; v/v). Yield = 85%1H-NMR(CDCl3, delta ppm): 0.96(t, 3H) ,1.25-1.39(m, 16H) ,1.43-1.46(d, 3H) ,1.6-1.7(m, 4H) ,2-2.1 (dt, 4H), 3.2(dt, 2H) ,4.2(q, IH) ,5.32-5.35(dt, 2H).

Reference： [1]Patent: WO2009/109973,2009,A2 .Location in patent: Page/Page column 63

12
[ 147962-41-2 ]
[ 112-90-3 ]
N-oleyl-N'-propylsulfamide [ No CAS ]
N,N'-dioleylsulfamide [ No CAS ]

Reference： [1]European Journal of Medicinal Chemistry,2009,vol. 44,p. 4889 - 4895

13
[ 112-90-3 ]
[ 175281-76-2 ]
[ 1356856-98-8 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 128 - 131

14
[ 112-90-3 ]
[ 124-30-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogen;palladium on activated charcoal; In ethanol; at 30℃; under 6000.6 Torr; for 4h;	a) Octadecylamine 2 g of oleylamine in 120 ml of ethanol are hydrogenated at 30 C. under 8 bar of hydrogen in the presence of palladium-on-charcoal. After reacting for 4 h and evaporating the solvent, 1.6 g of product are obtained in the form of a white powder. m/z: ES+ 270.7

Reference： [1]Patent: US8268810,2012,B2 .Location in patent: Page/Page column 42; 44
[2]RSC Advances,2015,vol. 5,p. 16497 - 16500

15
[ 112-90-3 ]
[ 17355-75-8 ]
[ 1428261-48-6 ]

Yield	Reaction Conditions	Operation in experiment
84%		General procedure: To a solution of the corresponding amine (5 equiv) in dry DCM was added a solution of Al(Me)3 in heptane (2 M, 5 equiv) under N2 atmosphere. The mixture was stirred at rt for 1 h. Then, a solution of alkyl carboxylate (1 equiv) in dry DCM was added dropwise. The mixture was refluxed for 14-48 h, and then was carefully poured onto 1 N HCl. The biphasic solution was heated to 40 C for 30 min and cooled to rt. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluent n-hexane/EtOAc, 9:1 for pyrazoles and 1:1 for triazoles), except 8b which was recrystallized from hexane.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1708 - 1716

16
[ 741287-00-3 ]
[ 112-90-3 ]
[ 1428261-51-1 ]

Yield	Reaction Conditions	Operation in experiment
68%		General procedure: To a solution of the corresponding amine (5 equiv) in dry DCM was added a solution of Al(Me)3 in heptane (2 M, 5 equiv) under N2 atmosphere. The mixture was stirred at rt for 1 h. Then, a solution of alkyl carboxylate (1 equiv) in dry DCM was added dropwise. The mixture was refluxed for 14-48 h, and then was carefully poured onto 1 N HCl. The biphasic solution was heated to 40 C for 30 min and cooled to rt. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluent n-hexane/EtOAc, 9:1 for pyrazoles and 1:1 for triazoles), except 8b which was recrystallized from hexane.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1708 - 1716

17
[ 112-90-3 ]
[ 1134647-60-1 ]
[ 1442019-83-1 ]

Yield	Reaction Conditions	Operation in experiment
53%		General procedure: To a solution of the corresponding amine (5 equiv) in dry DCM was added a solution of Al(Me)3 in heptane (2 M, 5 equiv) under N2 atmosphere. The mixture was stirred at rt for 1 h. Then, a solution of alkyl carboxylate (1 equiv) in dry DCM was added dropwise. The mixture was refluxed for 14-48 h, and then was carefully poured onto 1 N HCl. The biphasic solution was heated to 40 C for 30 min and cooled to rt. The organic layer was separated, dried over MgSO4 and evaporated. The residue was purified by flash chromatography (eluent n-hexane/EtOAc, 9:1 for pyrazoles and 1:1 for triazoles), except 8b which was recrystallized from hexane.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 1708 - 1716

18
[ 112-90-3 ]
[ 3173-56-6 ]
[ 1450603-58-3 ]

Yield	Reaction Conditions	Operation in experiment
51%	In N,N-dimethyl acetamide; at 20℃;	General procedure: To a solution of 1i (200mg, 0.75mmol) in dry DMA (3mL) was added benzyl isocyanate (102muL, 0.82mmol). The reaction was stirred at room temperature overnight. Ethyl acetate (80mL) was added and the solution was washed with saturated aq. NaHCO3 (30ml), brine (30ml), and was dried over Na2SO4 and concentrated to dryness. The crude was purified by flash chromatography on silica gel eluting with hexane/EtOAc (4:1) to yield a white solid (152mg, 51%). Mp 74-76; 1H NMR (400MHz, CDCl3) delta 7.23-7.35 (m, 5H), 5.33-5.36 (m, 2H), 4.68 (br s, 1H), 4.36 (s, 3H), 3.14 (t, J=6.8Hz,2H), 1.98-2.03 (m, 4H), 1.43-1.47 (m, 2H), 1.26-1.32 (m, 22H), 0.88 (t, J=6.8Hz, 3H); 13C NMR (CDCl3, 100MHz) delta 158.33, 139.43, 130.26, 130.20, 130.15, 130.07, 129.97, 128.89, 127.70, 44.86, 40.93, 32.13, 30.40, 29.98, 29.76, 29.70, 29.55, 27.45, 27.08, 22.91, 14.32; LCMS, C26H44N2O, [M+H]: 401.

Reference： [1]Bioorganic and Medicinal Chemistry,2013,vol. 21,p. 5188 - 5197

19
[ 112-90-3 ]
[ 120341-33-5 ]
C₄₆H₈₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	General procedure: Oleylamine (5.35g, 20mmol) was added to the anhydrous dichloromethane solution (200mL) of 4 (10 mmol), 1-Ethyl-3-(3-dimethyllaminopropyl)carbodiimide hydrochloride (EDC·HCl, 4.22g, 22mmol), 1-Hydroxybenzotrizole (HOBt, 2.97g, 22mmol) and N,N-Diisopropylethylamine (DIEA, 5.16g, 44mmol) in ice-salt-bath at 0C for 1 h and then at room temperature overnight. The mixture was then washed with saturated aqueous NaHCO3 solution (2×80 mL) and saturated brine (80 mL).The organic phase was dried over Na2SO4, filtered, and concentrated to afford an oil solid, which was further purified by column chromatography on silica gel (EA/PE=1:1, v/v) to yield the synthetic precursor 5a and 5c (Rf = 0.6, EA/PE = 2 : 1, v/v).

Reference： [1]Molecular Pharmaceutics,2016,vol. 13,p. 1809 - 1821
[2]Bioorganic and Medicinal Chemistry Letters,2014,vol. 24,p. 1771 - 1775

20
[ 112-90-3 ]
[ 1632125-04-2 ]
[ 1632124-88-9 ]

Yield	Reaction Conditions	Operation in experiment
53 mg	With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃;	A solution of 17 (119 mg, 0.23 mmol) in EtOH:1M NaOH (1:1, 3 mL) was stirred for 2 h at r.t. Then, the mixture was neutralized withIRA-120 (H+) resin, filtered and concentrated. The residue thus obtained was dissolved in DMF(2 mL) and oleyl amine (67 mg, 0.25 mmol), DIPEA (118 L, 0.69 mmol) and PyBOP (130 mg,0.25 mmol) were added. After stirring at r.t. overnight, the mixture was evaporated to dryness and the residue was dissolved in CH2Cl2 and washed with 1M HCl, sat. aq. soln. of NaHCO3 and sat. aq. soln. of NaCl. The dried organic phase (MgSO4) was purified by chromatography over silica gel (AcOEt:petroleum ether 1:3) to give 18 as an oil (53 mg, 30%). [alpha]D 29 -1.7 (c 1.05,CH2Cl2); IR (nu cm-1) 3299, 2921, 2852, 1643, 1110, 1092, 823, 738, 701, 614. 1H NMR (300MHz, CDCl3, ppm, J Hz) 7.73-7.67 (m, 4H, H-arom.), 7.42-7.35 (m, 6H, H-arom.), 6.56 (brt, 1H, NH), 5.38-5.32 (m, 2H, CH=CH), 4.62 (dd, 1H, J 6.5, J 4.8, H-3), 4.50 (br dd, 1H, H-4),3.97 (dd, 1H, 2J1?a,1?b 10.0, J1?a,2 7.0, H-1?a), 3.76 (dd, 1H, J1?b,2 5.0, H-1?b), 3.20 (q, 2H, JH,H 6.4,CH2-NH), 2.83 (m, 1H, H-5), 2.70 (m, 1H, H-2), 2.63-2.35 (m, 4H, H-1??a, H-1??b, CH2-N),2.02-1.98 (m, 4H, CH2-CH=CH-CH2), 1.39 (s, 3H, C(CH3)2), 1.48-1.09 (m, 31H, 14CH2,C(CH3)2), 1.05 (s, 9H, C(CH3)3), 0.88 (t, 3H, JH,H 6.3, CH3), 0.83 (t, 3H, JH,H 7.2, CH3). 13CNMR (75.4 MHz, CDCl3, ppm) 171.3 (C=O), 135.7, 135.5, 133.7, 133.5 (C-arom.), 129.9,129.7 (CH=CH), 129.6, 129.5, 127.6, 127.5 (C-arom.), 110.7 (C(CH3)2), 79.2 (C-4), 79.0 (C-3),67.6 (C-2), 63.4 (C-5), 62.5 (C-1?), 49.4 (C-1??), 35.2 (CH2-N), 32.6 (CH2), 31.9 (CH2), 29.7-29.2 (CH2), 27.2, 27.1 (CH2), 26.7 (C(CH3)3), 25.7, 25.0 (C(CH3)2), 22.6 (CH2), 20.6 (CH2), 19.1(C(CH3)3), 14.1, 14.0 (2CH3). CIMS m/z 775 [100%, (M+H)+]. HRCIMS m/z found 775.5804, calc. for C48H79N2O4Si: 775.5809.

Reference： [1]ARKIVOC,2014,vol. 2014,p. 197 - 214

21
[ 112-90-3 ]
[ 81438-31-5 ]
4-(2-hydroxy-3-octadec-8-enylaminopropoxy)chromen-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	In ethanol; at 20℃; for 6h;	General procedure: To a solution of oxiranylmethoxy-chromen-2-one 1 (0.5 g,2.29 mmol) in ethanol was added the appropriate amine (3.43 mmol) and the reaction was stirred at room temperature (except for 10, reaction was performed under refluxing condition) for 4-6 h. The reaction mixture was evaporated under vacuum and the crude product was purified by column chromatography using 3% methanol in chloroform as mobile phase to give desired products 2-11 in excellent yields.

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 94,p. 211 - 217

22
[ 112-90-3 ]
[ 24689-27-8 ]
7-(2-hydroxy-3-oleylaminopropoxy)-4-methyl-2H-1-benzopyran-2-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	In ethanol; at 20℃;	General procedure: To a solution of compound 2 (0.30 g, 1.29 mmol) inethanol (10 ml), corresponding amine was added in equimolaramount. The reaction mixture was stirred at room temperaturefor 4-6 h (except for compound 6 and 12: carriedout at 80 C for 8 h). The solvent was removed under reducedpressure and residue was purified by column chromatography (SiO2) using chloroform:methanol (9:1) as eluent toafford the desired compound in excellent yield.

Reference： [1]Medicinal Chemistry,2015,vol. 11,p. 128 - 134

23
[ 112-90-3 ]
[ 79-10-7 ]
(Z)-3-(octadec-9-en-1-ylamino)propanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63 g	at 40 - 100℃; for 2h;	Example 2 Process for Obtaining the Corrosion Inhibiting Composition Consisting of 3-(octadec-9-enylamino)propanoic acid (2) In a three-necked balloon flask of 500 ml equipped with a magnetic stirrer, a dropping funnel, a thermometer and a condenser were added 50 g (0.187 mol) of oleylamine at a temperature of 40 C. with vigorous stirring slowly added 13.48 g (0.187 mol) of acrylic acid. The reaction is exothermic and the temperature under these conditions rises gradually to 90 C. The reaction mixture was stirred under these conditions for 2 hours and then increased to 100 C. Purification of amino propionic acid was performed using an extraction of the amine did not react with hexane, thus obtaining 63 g of corrosion inhibitor compound with a yield of 92% as a very viscous pale yellow, features spectroscopy are: FTIR (cm-1): 2921, 2854, 1642, 1575, 1463, 1349, 1288, 1209, 1116, 963, 833. 1H NMR (CDCl3), 200 MHz, 8 (ppm): 5.31, 3.02, 2.73, 2.47, 1.98, 1.25, 0.85. 13C NMR (CDCl3), 50 MHz, 8 (ppm): 176.8, 129.9, 129.7, 47.5, 44.8, 40.8, 31.8, 29.7, 29.5, 29.2, 27.2, 22.6 and 14.1.
	With 10H-phenothiazine; In methanol; water; at 30 - 80℃; for 5h;	Step 1: 1 mole of acrylic acid (or 80% acrylic in water) and 0.2 g of phenothiazine (optional) are added into 100 ml methanol (or other alcohol or glycol or glycol ether) and cooled by ice bath and the temperature kept lower than 30 C. To that solution, 1 mole of oleylamine (e.g. as 50 wt % solution) is added drop-wise for 1 hour. After addition it is heated up to 80 C. and kept at 80 C. for 4 hours. Removing methanol by rotary evaporator, N-oleyl-beta-alanine is obtained.

Reference： [1]Patent: US2015/112096,2015,A1 .Location in patent: Paragraph 0051
[2]Patent: US2020/10754,2020,A1 .Location in patent: Paragraph 0082

24
[ 112-90-3 ]
[ 302-79-4 ]
[ 538-75-0 ]
[ 65646-61-9 ]
N-oleylretinamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With dmap; In dimethyl sulfoxide; at 25℃;	General procedure: The synthesis of the target compounds was achieved by dissolving a long chain fatty amine (0.011 mol), ATRA (0.011 mol) and DCC (0.011 mol) in DMSO (50 mL). A catalytic amount of DMAP (0.001 mol) was added, and the solution was stirred at room temperature. After completion of the reaction, the reaction mixture was filtered (to remove solid dicyclohexylurea), and the filtrate was dried under reduced pressure. The amidic derivatives 3a and 3b and the acyl urea derivative 4 of ATRA were obtained by column chromatography using gradient elution with hexane and chloroform. The identity of the desired compounds was confirmed using infrared (IR) and 1H and 13C nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry as shown below.

Reference： [1]Molecules,2015,vol. 20,p. 8181 - 8197

25
[ 112-90-3 ]
[ 13726-67-5 ]
C₄₅H₈₅N₃O₄ [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2014,vol. 11,p. 4164 - 4178

26
[ 112-90-3 ]
[ 34404-28-9 ]
C₄₆H₈₇N₃O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68.4%		General procedure: N-Boc-D-Aspartic acid (5 mmol)25 or N-Boc-D-glutamic acid,26which was prepared according to literature procedure, was dissolvedin CH2Cl2 (50 mL), cooled to 0 C. 1-Hydroxybenzotriazole(HOBt) (1.83 g, 12 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimidehydrochloride (EDCHCl) (2.3 g, 12 mmol) and DIEA(2.58 g, 2 mmol) were gradually added for activation of carboxylicacid. After 0.5 h stirring, oleyl amine (3.57 g, 90%, 12 mmol) wasadded, and resulting mixture was stirred at room temperatureovernight. The solvent was then removed under reduced pressure.EtOAc was added to dissolve the residue, and the solution waswashed with water, saturated aqueous NaHCO3 solution and saturatedbrine. The organic layer was dried over anhydrous sodiumsulfate and concentrated to give a white solid. The crude productwas purified by silica gel column chromatography (PE/EA = 1/1,v/v).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763
[2]RSC Advances,2017,vol. 7,p. 8823 - 8831

27
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.2 g		Example 20 Preparation of C18(oleic)-norArg-C18 N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide (0607) Fmoc-Dab(Boc)-resin. To 5 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 50 ml of dry DCM in 60 ml reaction vessel for solid phase synthesis, 5.726 g (13 mmol, 2 eq) of Fmoc-Dab(Boc)-OH (Mw=440.5, (Fmoc-(N-gamma-Boc)-L-alpha,gamma-diaminobutyric acid, AnaSpec, 28246) and 2.26 ml (13 mmol, 2.0 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added. (0608) Dab(Boc)-resin. After 3 hrs the resin was washed 3× with DCM/MeOH/DIPEA (17:2:1), 3×DCM, 2×DMF, 3×DCM and Fmoc group was deprotected with 50 ml of 20percent piperidine/DMF twice for 15 min. (0609) C18:1-Dab(Boc)-resin. After Fmoc deprotection the resin was washed with 3×DCM, 2×MeOH and 3×DCM and for the coupling reaction 3.7 g (13 mmol) of oleic acid (Sigma, Mw=282.47, d=0.891), 5.37 g (13 mmol) of HCTU (Mw=413.7) and 2.62 ml (13 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. (0610) After 1 hr of reaction the resin was washed with 3×DCM, 2×MeOH and 3×DCM and progress of reaction was checked by Kaiser test which was negative (no free amine groups present). (0611) C18:1-Dab(Boc)-OH (Mw=566.56) was cleaved from the resin by 1percent TFA/DCM (5×50 ml for 2 min was filtered to flask with 2 ml 10percent pyridine/MeOH) and solvent was evaporated. (0612) C18:1-Dab(Boc)-C18:1 (Mw=734.95). Second coupling was carried out in solution. To the oily residue from the previous reaction, 3.725 g (9.75 mmol) of oleyl amine (Sigma, Mw=267.49, 70percent), 4.033 g (9.75 mmol) of HCTU (Mw=413.7) and 1.69 ml (9.75 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. After 4 hr 100 ml of AcOEt was added and organic layer was washed in separatory funnel with 3×0.5 M HCl, 3×10percent NaCO3 and 3×NaCl. AcOEt layer was dried with anhydrous MgSO4 and evaporated. (0613) C18:1-Dab-C18 (Mw=635.9). To the oily residue from the previous reaction, 100 ml of 80percent TFA/DCM 2.5percent TIS was added and after 20 min solvent was evaporated. (0614) C18:1-norArg(diBoc)-C18:1 (Mw=874.13). The residue was dissolved in 50 ml of DCM and pH was adjusted to 9 with TEA. 2.348 g (6 mM, 1 eq) of 1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine (Mw=391.36, Aldrich 15033) was added and after 4 hrs DCM was evaporated. (0615) C18:1-norArg-C18:1 (Mw=674.1) To the oily residue from the previous reaction 100 ml of 95percent TFA/DCM 2.5percent TIS was added and after 3 hrs solvent was evaporated. Crude product was purified on TELEDYNE Isco CombiFlash Rf instrument using 48 g normal phase silica gel column, 100percent DCM for 3 CV (column volume) and 0-20percent MeOH for 10 CV, detection 214 nm, flow 45 ml/min. DCM/MeOH was evaporated and residue was precipitated by 0.1M HCl. Yield: 3.2 g.

Reference： [1]Patent: US9339461,2016,B2 .Location in patent: Page/Page column 86-87

28
[ 112-90-3 ]
[ 2483-46-7 ]
C₃₄H₆₅N₃O₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
82%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20℃;	General procedure: Step 2: Oleylamine (1.2 equiv.) was added to the anhydrous dichloromethane solution of the product obtained in last step (1 equiv.), HOBt (1.2 equiv.), EDCI (1.2 equiv.) and DIEA (2 equiv.) in ice-salt-bath at 0C. The mixture was stirred at 0C for 1h and then at room temperature overnight. The reaction solution was washed with saturated aqueous NaHCO3 solution (2×50mL) and brine (50mL). The organic solvent was dried over Na2SO4, filtered, and concentrated to afford an oil solid, which was further purified by column chromatography on silica gel (EA/PE=1/2, v/v) to yield pure compound 1 (85%) or 2 (66%).

Reference： [1]European Journal of Medicinal Chemistry,2017,vol. 136,p. 585 - 595

29
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-((Z)-octadec-9-en-1-ylamino)-1-oxobutan-2-yl)oleamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		C18:1-norArg-C18:1 was synthesized as follows. Fmoc-N gamma-Boc-L-2,3-diaminobutyric acid was dissolved in dichloromethane (DCM), 2eq of diisopropylethyl amine (DIPEA) and the resulting solution was added to 2-chlorotrityl choride resin. After one hour, the resin was washed with DCM and Fmoc group was removed by treatment with 20percent piperidine in DMF yielding the free alpha-amine. Oleic acid was preactivated with 2-(6-Chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU) and 2 equivalents of DIPEA and added to the resin and the reaction was deemed complete by negative Kaiser test. The lipidated compound was cleaved from the resin by multiple treatments with 1percent trifluoroacetic acid (TFA) in dichloromethane followed by evaporation under reduced pressure yielding free carboxylate intermediate. The second alkyl chain was attached by preactivating the free carboxyl group with (1-Ethyl-3-(3-dimethyllaminopropyl)-carbodiimide hydrochloride) (EDC) and N-Hydroxybenzotriazole (HOBt) in a 1:1 mixture of DMF and DCM for 10 minutes followed by addition of oleyl amine in same solvent and subsequent stirring for 30 minutes. Crude compound was purified by flash chromatography (Hexane/AcOEt gradient). The pure dialkylated intermediate was dissolved in 1M HCl/ethyl acetate solution and the Boc group was removed within one hour followed by removal of the solvent under reduced pressure. The resulting white solid was taken up in DCM to which was added TEA facilitate dissolution followed by treatment with 1, 3 Di-Boc-2-(trifluoromethylsulfonyl) guanidine for one hour. Upon completion of the reaction DCM was washed with 2 M sodium bisulfate, saturated sodium bicarbonate and dried over MgSO4 and removed under reduced pressure. The resulting residue was dissolved in absolute ethanol and two Boc groups were removed by adding dissolved compound drop wise to 12N HCl. Final product precipitated during reaction and was crystallized from EtOH.

Reference： [1]Patent: US2017/216227,2017,A1 .Location in patent: Paragraph 0339

30
[ 112-90-3 ]
C₁₅H₁₂F₉N₆P [ No CAS ]
C₅₄H₁₀₈N₃P [ No CAS ]
[ 10010-93-2 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 14737 - 14742
Angew. Chem.,2017,vol. 129,p. 14932 - 14937,6

31
[ 112-90-3 ]
[ 1397-89-3 ]
C₆₅H₁₀₈N₂O₁₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		AmB-OA was synthesized by coupling oleyl amine (OA) to the free carboxyl groups of AmB. The covalent modification of these groups involved four sequential steps: (i) protection of the free amine group with BOC; (ii) activation of the free carboxyl group with (EDC), (iii) conjugation with OA, and (iv) acid treatment (6N HCl) to deprotect the amine group of conjugate (Fig. 1). Briefly, BOC anhydride (100 mul,10 mol ratio) was added to AmB (150 mg, 1 mol ratio) dissolved in DMSO (7 ml) in a round bottom flask and stirred for 8-10 h at room temperature (rt). The reaction was performed in the presence of anhydrous triethylamine as base. To the resultant mixture, EDC(37.34 mg, 1.2 mol ratio) in DMSO (1 ml) was added and allowed to stirat 350 rpm for 18 h at rt. Finally, 52.1 mul, ?70% (1.2 mol ratio), OAdissolved in methanol (1 ml) was added to the above mixture and stirred further for 24 h. The prepared conjugate was precipitated in ice cold ether followed by washing with cold water and separated by centrifugation at 22,000×g for 10 min (the yield was ?90%). The obtained product was further treated with acid (6N HCl, 10 mg/ml) to remove the BOC protection (yield ?80%). The differential solubility of AmB and AmB-OA was employed to separate unreacted AmB from the final product. Purification of the conjugate was performed by repeated washings with water and dried using lyophilization (Jain et al., 2011b).

Reference： [1]International Journal of Pharmaceutics,2018,vol. 544,p. 1 - 13

32
[ 112-90-3 ]
[ 1397-89-3 ]
C₆₆H₁₁₀N₂O₁₆ [ No CAS ]

Reference： [1]Molecular Pharmaceutics,2019,vol. 16,p. 4519 - 4529

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P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 112-90-3 ]

Quality Control of [ 112-90-3 ]

Related Doc. of [ 112-90-3 ]

Product Details of [ 112-90-3 ]

Calculated chemistry of of [ 112-90-3 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 112-90-3 ]

Application In Synthesis of [ 112-90-3 ]

[ 112-90-3 ] Synthesis Path-Upstream 1~2

[ 112-90-3 ] Synthesis Path-Downstream 1~32

Related Functional Groups of [ 112-90-3 ]

Alkenyls

Amines

Aliphatic Chain Hydrocarbons

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 112-90-3 ]