[ CAS No. 1015460-59-9 ] {[proInfo.proName]}

Name: 1015460-59-9|7-Bromo-5H-pyrido[4,3-b]indole|95%
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SKU: A223708
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Quality Control of [ 1015460-59-9 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 1015460-59-9 ]

CAS No. :	1015460-59-9	MDL No. :	MFCD18803689
Formula :	C₁₁H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	JYFKMOCKASWCPZ-UHFFFAOYSA-N
M.W :	247.09	Pubchem ID :	71079324
Synonyms :

Calculated chemistry of [ 1015460-59-9 ]

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	13
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	1.0
Molar Refractivity :	61.3
TPSA :	28.68 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	Yes
Log Kp (skin permeation) :	-5.67 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	3.01
Log Po/w (WLOGP) :	3.48
Log Po/w (MLOGP) :	2.31
Log Po/w (SILICOS-IT) :	3.71
Consensus Log Po/w :	2.88

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.96
Solubility :	0.0274 mg/ml ; 0.000111 mol/l
Class :	Soluble
Log S (Ali) :	-3.28
Solubility :	0.131 mg/ml ; 0.000528 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.44
Solubility :	0.000889 mg/ml ; 0.0000036 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.57

Safety of [ 1015460-59-9 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H317-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 1015460-59-9 ]

* 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 [ 1015460-59-9 ]
Downstream synthetic route of [ 1015460-59-9 ]

[ 1015460-59-9 ] Synthesis Path-Upstream 1~6

1
[ 89364-04-5 ]
[ 1015460-59-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2015, vol. 25, # 15, p. 2953 - 2957
[2] Journal of Medicinal Chemistry, 2016, vol. 59, # 10, p. 4778 - 4789
[3] Patent: CN106588915, 2017, A,
[4] Patent: US2018/125821, 2018, A1,

2
[ 5467-74-3 ]
[ 1015460-59-9 ]

3
[ 27246-81-7 ]
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[ 1015460-62-4 ]

Reference： [1] Synlett, 2008, # 1, p. 77 - 82

4
[ 62829-47-4 ]
[ 27246-81-7 ]
[ 1015460-59-9 ]
[ 1015460-62-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7350 - 7370

5
[ 27246-81-7 ]
[ 244-69-9 ]
[ 1015460-59-9 ]
[ 1015460-62-4 ]

Reference： [1] Synlett, 2008, # 1, p. 77 - 82

6
[ 62829-47-4 ]
[ 27246-81-7 ]
[ 1015460-59-9 ]
[ 1015460-62-4 ]

Reference： [1] Journal of Medicinal Chemistry, 2017, vol. 60, # 17, p. 7350 - 7370

[ 1015460-59-9 ] Synthesis Path-Downstream 1~81

1
N-acetyl-3-bromo-4-piperidone hydrobromide [ No CAS ]
[ 27246-81-7 ]
[ 244-69-9 ]
[ 1015460-59-9 ]
[ 1015460-62-4 ]

Reference： [1]Synlett,2008,p. 77 - 82

2
[ 1015460-59-9 ]
3-(5-(tert-butoxycarbonyl)-5H-pyrido[4,3-b]indol-7-yl)pyridine-1-oxide [ No CAS ]

Reference： [1]Patent: WO2015/47902,2015,A1

3
[ 1015460-59-9 ]
5-(5-(tert-butoxycarbonyl)-5H-pyrido[4,3-b]indol-7-yl)-N,N,N-trimethylpyridin-2-aminium-4-methylbenzenesulfonate [ No CAS ]

Reference： [1]Patent: WO2015/47902,2015,A1

4
[ 1015460-59-9 ]
[ 24424-99-5 ]
C₂₃H₂₈N₂O₄ [ No CAS ]

Reference： [1]Patent: WO2015/47902,2015,A1

5
[ 1015460-59-9 ]
[ 24424-99-5 ]
tert-butyl 7-bromo-5H-pyrido[4,3-b]indole-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
87%	With dmap; In dichloromethane; at 20℃; for 6h;	990 mg (4.0 mmol) of 7-bromo-5-hydro-pyrido [4,3-b] indole,586 mg (4.8 mmol) of dimethylaminopyridine,1.4 g (6.4 mmol) of di-tert-butyl dicarbonate,Was dissolved in 100 mL of dichloromethane,After 6 h at room temperature, the solvent was removed in vacuo,The solid was isolated by column chromatography to give 1.2 g of pale yellow solid (yield: 87%)
86%	With dmap; In tetrahydrofuran; at 20℃; for 4h;Inert atmosphere;	A round bottomed flask is charged with <strong>[1015460-59-9]7-bromo-5H-pyrido[4,3-b]indole</strong> (15.00 g, 60.7 mmol), di-tert-butyl dicarbonate (19.87 g, 91.1 mmol, 1.5 eq), and dimethylaminopyridine (0.204 g, 1.8 mmol, 0.03 eq). Tetrahydrofuran (550 mL) is added and the resulting brown solution is allowed to stir at room temperature. The reaction is determined to be complete by LCMS after 4 hours. The reaction is concentrated to a brown solid. The solids are triturated in approximately 500 mL hexanes (with stirring), isolated by filtration, washed with hexanes, and then dried under high vacuum to afford the title compound as a dark tan solid (18.03 g, 86%). The material is used in the subsequent step without further purification. 1H NMR (400 MHz, DMSO-d6): delta 9.37 (d, 7=1.2 Hz, 1H), 8.59 (d, Jo=6.0 Hz, 1H), 8.36 (d, 7=1.2 Hz, 1H), 8.19 (dd, 7=8.4 Hz, 7=0.4 Hz, 1H), 7.99 (dd, J,=6.0 Hz, Jm=1.2 Hz, 1H), 7.59 (dd, J,=8.4 Hz, Jm=1.6 Hz, 1H), 1.66 (s, 9H). 13C NMR (100.6 MHz, CDCl3): delta 150.06, 147.46, 143.37, 142.47, 139.07, 127.07, 122.51, 122.71, 121.27, 120.92, 119.67, 110.97, 85.67, 28.24. HRMS: Calc for C16H15N2O2Br (M+H)+ 347.0395, found 347.0400, Err= 1.4 ppm.
86%	With dmap; In dichloromethane; at 20℃; for 6h;Inert atmosphere;	The mixture of compound 2 (495mg, 2.0mmol), DMAP (293mg, 2.4mmol), and (Boc)2O (698mg, 3.2mmol) in CH2Cl2 (70mL) was stirred at rt for 6h, and then was concentrated to dryness. The solid residue was purified by silica gel chromatography using an eluent (2:98 MeOH/CH2Cl2) to give a white solid product 7 (597mg, 86%). Rf=0.79 (1:12 MeOH/CH2Cl2), mp 156-158C. 1H NMR (CDCl3): delta 1.77 (s, 9H, 3×CH3), 7.53 (dd, J=1.5, 8.0Hz, 1H, Ar-H), 7.89 (d, J=8.0Hz, 1H, Ar-H), 8.08 (d, J=6.0Hz, 1H, Ar-H), 8.54 (d, J=0.5Hz, 1H, Ar-H), 8.64 (d, J=6.0Hz, 1H, Ar-H), 9.23 (d, J=1.0Hz, 1H, Ar-H). MS (ESI): 347 ([M+H]+, 100%).(i).

Reference： [1]Patent: CN106588915,2017,A .Location in patent: Paragraph 0023; 0024
[2]Patent: WO2015/47902,2015,A1 .Location in patent: Page/Page column 14; 15
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[4]PLoS ONE,2019,vol. 14

6
[ 89364-04-5 ]
[ 1015460-59-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[2]Journal of Medicinal Chemistry,2016,vol. 59,p. 4778 - 4789
[3]Patent: CN106588915,2017,A
[4]Patent: US2018/125821,2018,A1
[5]PLoS ONE,2019,vol. 14

7
[ 5467-74-3 ]
[ 1015460-59-9 ]

8
[ 1015460-59-9 ]
[ 351019-18-6 ]
7-(6-fluoropyridin-3-yl)-5H-pyrido[4,3-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%		Step 3: 7-(6-Fluoropyridin-3-yl)-5H-pyrido[4,3-b]indole A mixture of <strong>[1015460-59-9]7-bromo-5H-pyrido[4,3-b]indole</strong> (400 mg, 1.63 mmol), (6-fluoropyridin-3-yl)boronic acid (344 mg, 2.44 mmol), PdCl2(dppf) (120 mg, 0.163 mmol), tBu3PHBF4 (95 mg, 0.326 mmol) and Cs2CO3 (1.1 g, 3.26 mmol) in dioxane/water (20 mL, 20:1) was heated to 90 C. for 4 hours under N2. The solid was filtered and the filtrate was evaporated. The residue was purified by chromatography (silica gel, 200-300 mesh, CH2Cl2: MeOH=30:1) to afford 7-(6-Fluoropyridin-3-yl)-5H-pyrido[4,3-b]indole (250 mg, 59% yield).
53%	With palladium diacetate; potassium carbonate; CyJohnPhos; In 1,2-dimethoxyethane; water; for 48h;Reflux;	Palladium(II) acetate (18mg, 0.08mmol) was added to a solution containing compound 2 (198mg, 0.8mmol), (6-fluoropyridin-3-yl)boronic acid (158mg, 1.12mmol), dicyclohexylphosphinobiphenyl (30.8mg, 0.088mmol) and K2CO3 (332mg, 2.4mmol) in DME (50mL) and water (6mL). The reaction mixture was refluxed for 48h, cooled down to room temperature (rt), diluted with water and extracted with ethyl acetate (50mL×3). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in reduced pressure. The residue was purified by silica gel chromatography using an eluent (2:98 MeOH/CH2Cl2) to obtain a white solid product 3 (112mg, 53%). Rf=0.33 (1:12 MeOH/CH2Cl2), mp >300C. 1H NMR (acetone-d6): delta 7.20 (ddd, J=0.5, 3.5, 8.5Hz, 1H, Ar-H), 7.50 (dd, J=0.8, 6.0Hz, 1H, Ar-H), 7.61 (dd, J=1.5, 8.0Hz, 1H, Ar-H), 7.89 (d, J=1.0Hz, 1H, Ar-H), 8.30-8.33 (m, 1H, Ar-H), 8.35 (d, J=8.0Hz, 1H, Ar-H), 8.47 (d, J=5.0Hz, 1H, Ar-H), 8.58 (dd, J=0.5, 2.0Hz, 1H, Ar-H), 9.39 (s, 1H, Ar-H), 10.95 (br s, 1H, NH). MS (ESI): 264 ([M+H]+, 100%). MS (ESI): 262 ([M-H]-, 20%).(

Reference： [1]Patent: US2018/125821,2018,A1
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[3]Journal of Medicinal Chemistry,2016,vol. 59,p. 4778 - 4789
[4]PLoS ONE,2019,vol. 14

9
3-(4-bromophenyl)-4-nitropyridine [ No CAS ]
[ 1015460-59-9 ]

Yield	Reaction Conditions	Operation in experiment
71%	With triethyl phosphite; at 110℃; for 3h;Inert atmosphere;	1.68 g of 3- (4-bromobenzene) -4-nitropyridineDissolved in 60mLTriethyl phosphite,Under nitrogen protection, heating at 110 for 3h,cool down,The triethyl phosphite was removed under reduced pressure,The resulting solid was separated by column chromatography,To give 1.05 g of brown-yellow solid (yield: 71%).
70%	With triethyl phosphite; at 110℃; for 3h;Inert atmosphere;	A solution of compound 1 (0.84g, 3.0mmol) in 30mL of triethyl phosphate was heated at 110C for 3h under N2. The reaction was monitored with TLC for every 1h. After the starting material was disappeared, the reaction mixture was cooled down, and volatiles were removed in vacuo. The residue was purified by silica gel chromatography using an eluent (2:98 MeOH/CH2Cl2) to give a light brown color solid product 2 (0.52g, 70%). Rf=0.48 (1:12 MeOH/CH2Cl2), mp 258-260C (dec.). 1H NMR (DMSO-d6): delta 7.42 (dd, J=2.0, 8.5Hz, 1H, Ar-H), 7.49 (dd, J=1.0, 5.5Hz, 1H, Ar-H), 7.76 (d, J=2.0Hz, 1H, Ar-H), 8.1 (d, J=8.5Hz, 1H, Ar-H), 8.4 (d, J=5.5Hz, 1H, Ar-H), 9.36 (s, 1H, Ar-H), 11.82 (s, 1H, NH). MS (ESI): 247 ([M+H]+, 100%).
62%		Step 2: 7-bromo-5H-pyrido[4,3-b]indole A mixture of 3-(4-bromophenyl)-4-nitropyridine (20.0 g, 71.7 mmol) in triethyl phosphate (400 ml) was stirred at 110 C. for 2 hours under nitrogen atmosphere. TLC showed the reaction was complete. The volatiles were evaporated under reduced pressure to give a residue which was purified by recrystallization (methanol) to afford 7-bromo-5H-pyrido[4,3-b]indole (11.0 g, yield 62%) as brown solid.

Reference： [1]Patent: CN106588915,2017,A .Location in patent: Paragraph 0021; 0022
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[3]Patent: US2018/125821,2018,A1
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 4778 - 4789
[5]PLoS ONE,2019,vol. 14

10
[ 1015460-59-9 ]
7-(6-aminopyrid-3-yl)-5H-pyrido[4,3-b]indole [ No CAS ]

11
[ 1015460-59-9 ]
[ 1415379-89-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957

12
[ 1015460-59-9 ]
[ 1533432-50-6 ]

13
[ 1015460-59-9 ]
7-(6-[¹⁸F]-fluoropyridin-3-yl)-5H-pyrido[4,3-b]indole [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[3]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[4]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[5]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[6]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[7]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[8]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[9]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957
[10]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957

14
[ 1015460-59-9 ]
trimethyl-(6-nitro-3-pyridyl)stannane [ No CAS ]
[ 1415379-89-3 ]

Yield	Reaction Conditions	Operation in experiment
26%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	Method B (from 4): A mixture of compound 2 (99mg, 0.4mmol), 4 (184mg, 0.64mmol), Pd(PPh3)4 (46mg, 0.04mmol), and Cs2CO3 (391mg, 1.2mmol) in 1,4-dioxane (100mL) was stirred at 100C under N2 atmosphere for 20h. After cooling to RT, the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography using an eluent (3:97 MeOH/CH2Cl2) to obtain a yellow solid product 5 (30mg, 26%). Analytical data was identical with Method A.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957

15
[ 1015460-59-9 ]
2-nitro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine [ No CAS ]
[ 1415379-89-3 ]

Yield	Reaction Conditions	Operation in experiment
7%	With tetrakis(triphenylphosphine) palladium(0); caesium carbonate; In 1,4-dioxane; at 100℃; for 20h;Inert atmosphere;	Method A: A mixture of compound 2 (99mg, 0.4mmol), 2-nitro-5-pyridineboronic acid pinacol ester (160mg, 0.64mmol), Pd(PPh3)4 (46mg, 0.04mmol), and Cs2CO3 (391mg, 1.2mmol) in 1,4-dioxane (100mL) was stirred at 100C under N2 atmosphere for 20h. After cooling to RT, the volatiles were removed under reduced pressure. The residue was purified by silica gel chromatography using an eluent (3:97 MeOH/CH2Cl2) to afford a yellow solid product 5 (8mg, 7%). Rf=0.32 (1:12 MeOH/CH2Cl2), mp >300C. 1H NMR (DMSO-d6): delta 7.52 (d, J=5.5Hz, 1H, Ar-H), 7.76 (dd, J=1.5, 8.0Hz, 1H, Ar-H), 7.98-8.04 (m, 1H, Ar-H), 8.42-8.47 (m, 3H, Ar-H), 8.61 (dd, J=2.5, 8.5Hz, 1H, Ar-H), 9.12 (d, J=2.0Hz, 1H, Ar-H), 9.42 (s, 1H, Ar-H), 11.96 (s, 1H, NH). MS (ESI): 291 ([M+H]+, 100%). MS (ESI): 289 ([M-H]-, 40%).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 2953 - 2957

16
[ 1015460-59-9 ]
[ 616-38-6 ]
7-bromo-5-methyl-5H-pyrido[4,3-b]indole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%		Preparative Example 23 (0778) (0779) Step A (0780) To a solution of custom made <strong>[1015460-59-9]7-bromo-5H-pyrido[4,3-b]indole</strong> (0.49 g, 1.98 mmol) in N,N?-dimethylformamide (5 mL) was added cesium carbonate (0.32 g, 0.99 mmol) and the mixture was stirred at room temperature for 10 minutes and dimethylcarbonate was added dropwise (334 muL, 3.96 mmol). The reaction mixture was heated at 160 C. for 3 hours and after cooling, water (20 mL) and ethyl acetate (20 mL) were added to the mixture. The phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The organic phases were combined and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was purified on a HP-Sil column using a Biotage Isolera One purification system employing a dichloromethane/methanol gradient (100/0->90/10) to afford the crude title compound (0.36 g, 69%). (0781) 1H NMR (400 MHz, DMSO-d6) delta=9.36 (s, 1H), 8.52 (d, 1H), 8.21 (d, 1H), 7.95 (d, 1H), 7.62 (d, 1H), 7.45 (dd, 1H), 3.88 (s, 3H). (0782) MS (ESI): m/z=263.95 [M+H]+.
		To a solution of custom made 7-bromo-5H-pyrido[4,3-£>]indole (0.49 g, 1.98 mmol) in Lambda/,Lambda/'- dimethylformamide (5 mL) was added cesium carbonate (0.32 g, 0.99 mmol) and the mixture was stirred at room temperature for 10 minutes and dimethylcarbonate was added dropwise (334 mu, 3.96 mmol). The reaction mixture was heated at 160C for 3 hours and after cooling, water (20 mL) and ethyl acetate (20 mL) were added to the mixture. The phases were separated and the aqueous phase was extracted with ethyl acetate (2 X 20 mL). The organic phases were combined and dried over Na2S04. The solvent was removed under reduced pressure and the residue was purified on a HP-Sil column using a Biotage Isolera One purification system employing a dichloromethane/methanol gradient (100/0 -> 90/10) to afford the crude title compound (0.36 g, 69 %). 1H NMR (400 MHz, DMSO-cf6) delta = 9.36 (s, 1 H), 8.52 (d, 1 H), 8.21 (d, 1 H), 7.95 (d, 1 H), 7.62 (d, 1 H), 7.45 (dd, 1 H), 3.88 (s, 3H) MS (ESI): m/z = 263.95 [M+H]+

Reference： [1]Patent: US2017/2005,2017,A1 .Location in patent: Paragraph 0778; 0779; 0780; 0781; 0782
[2]Patent: WO2015/110263,2015,A1 .Location in patent: Page/Page column 162

17
[ 1015460-59-9 ]
7-(6-fluoropyridin-3-yl)-5H-pyrido[4,3-b]indole-6,8,9-t₃ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4778 - 4789

18
[ 1015460-59-9 ]
6,8,9-tribromo-7-(6-fluoropyridin-3-yl)-5H-pyrido[4,3-b]indole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2016,vol. 59,p. 4778 - 4789

19
[ 1015460-59-9 ]
tert-butyl 7-(6-aminopyrid-3-yl)-5H-pyrido[4,3-b]indole-5-carboxylate [ No CAS ]

Reference： [1]Patent: CN106588915,2017,A

20
[ 62829-47-4 ]
[ 27246-81-7 ]
[ 1015460-59-9 ]
[ 1015460-62-4 ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 7350 - 7370

21
[ 1015460-59-9 ]
tert-butyl 4-(5-methylpyrido[4,3-b]indol-7-yl)piperazine-1-carboxylate [ No CAS ]