[ CAS No. 1912-33-0 ] {[proInfo.proName]}

Name: 1912-33-0|Methyl 2-(1H-indol-3-yl)acetate|97%
Brand: Ambeed
SKU: A110895
Price: 10.0 USD
Availability: InStock
Rating: 93 (35 reviews)

,{[proInfo.pro_purity]}

Cat. No.: {[proInfo.prAm]}

DV 2D 3D

3d Animation Molecule Structure of 1912-33-0

Structure of 1912-33-0 * Storage: {[proInfo.prStorage]}

Please Login or Create an Account to: See VIP prices and availability

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

* Shipping: {[proInfo.prShipping]}

For Research Only 120K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 1912-33-0 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1912-33-0 ]

SDS Specification

Alternatived Products of [ 1912-33-0 ]

Product Details of [ 1912-33-0 ]

CAS No. :	1912-33-0	MDL No. :	MFCD00005636
Formula :	C₁₁H₁₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	KTHADMDGDNYQRX-UHFFFAOYSA-N
M.W :	189.21	Pubchem ID :	74706
Synonyms :

Calculated chemistry of [ 1912-33-0 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.18
Num. rotatable bonds :	3
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	54.16
TPSA :	42.09 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) :	-6.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.82
Log Po/w (XLOGP3) :	1.74
Log Po/w (WLOGP) :	1.88
Log Po/w (MLOGP) :	1.4
Log Po/w (SILICOS-IT) :	2.7
Consensus Log Po/w :	1.91

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.39
Solubility :	0.776 mg/ml ; 0.0041 mol/l
Class :	Soluble
Log S (Ali) :	-2.24
Solubility :	1.09 mg/ml ; 0.00575 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.77
Solubility :	0.0324 mg/ml ; 0.000171 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.65

Safety of [ 1912-33-0 ]

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

Application In Synthesis of [ 1912-33-0 ]

* 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 [ 1912-33-0 ]
Downstream synthetic route of [ 1912-33-0 ]

[ 1912-33-0 ] Synthesis Path-Upstream 1~6

1
[ 1912-33-0 ]
[ 4363-93-3 ]

Reference： [1] Tetrahedron, 1985, vol. 41, # 11, p. 2109 - 2114

2
[ 1912-33-0 ]
[ 879-37-8 ]

Reference： [1] Journal of the Chemical Society, 1952, p. 650,658

3
[ 1912-33-0 ]
[ 74-88-4 ]
[ 58665-00-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6 h;	N-Methyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, methyl iodide (223 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-methyl-3-indoleacetic acid methyl ester (140 mg, yield: 65percent); ¹H NMR (400 MHz, CDCl₃): δ 7.60 (d, J=7.9 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 7.9 Hz, 1H), 7.12 (dd, J=8.2, 7.9 Hz, 1H), 7.03 (s, 1H), 3.75 (s, 3H), 3.77 (s, 2H), 3.69 (s, 3H); ¹³C NMR (100 MHz, CDCl₃): δ 172.6, 136.9, 127.7, 121.7 (2C), 119.26, 118.9, 109.3, 106.8, 51.9, 32.7, 31.0.
19%	Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) for 1 h; Stage #2: for 18 h;	To a suspension of sodium hydride (104 mg, 7.61 [MMOL)] in DMF (11 mL) was added a solution of 1 H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 [MMOL)] in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 [MMOL).] The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3 x 100 mL). The combined organic layers were dried with [NA2SO4,] and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19percent) of [(1-METHYL-1H-INDOL-3-YL)-ACETIC] acid methyl ester after purification. HPLC: Rt = 8.91 (Method A). MS (ES+): mass calculated for [C12H13NO2,] 203.09 ; m/z found 204.09 [[M+H] +. 1H] NMR (400 MHz, [CDCI3)] : 7.60 (d, J = 7.9 Hz, [1 H),] 7.30 (d, [J =] 8.2 Hz, 1 H), 7.23 (t, J = 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 [(S,] [1 H),] 3.77 (s, 2H), 3.76 (s, [3H),] 3.69 (s, 3H).
19%	Stage #1: With sodium hydride In DMF (N,N-dimethyl-formamide) for 1 h; Stage #2: for 18 h;	To a suspension of20 sodium hydride (104 mg, 7.61 mmol) in DMF (11 ml) was added a solution of1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 ml). Themixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8mmol). The reaction mixture was stirred for an additional 18 h, quenched,diluted with saturated ammonium chloride (200 ml), and then extracted with25 diethyl ether (3 x 100 ml). The combined organic layers were dried withNasSCU, and the solvent was removed under reduced pressure. The cruderesidue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg(19percent) of (1 -methyl-1 H-indol-3-yl)-acetic acid methyl ester after purification.HPLC: R_t = 8.91 (Method A). MS (ES+): mass calculated for C₁₂H₁₃NO₂, 203.09; m/z found 204.09 [M+Hf. ¹H NMR (400 MHz, CDCI₃): 7.60 (d, J= 7.9Hz, 1H), 7.30 (d, J= 8.2 Hz, 1H), 7.23 (t, J= 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H),7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).

19%	With sodium hydride In DMF (N,N-dimethyl-formamide) for 19 h;	A. (1-Methyl-1H-indol-3-yl)-acetic acid methyl ester. To a suspension of sodium hydride (104 mg, 7.61 mmol) in DMF (11 mL) was added a solution of 1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 mmol). The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3*100 mL). The combined organic layers were dried with Na₂SO₄, and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19percent) of (1-methyl-1H-indol-3-yl)-acetic acid methyl ester after purification. HPLC: R_t=8.91 (Method A). MS (ES+): mass calculated for Cl₂H₁₃NO₂, 203.09; m/z found 204.09 [M+H]⁺. ¹H NMR (400 MHz, CDCl₃): 7.60 (d, J=7.9 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 7.23 (t, J=8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).
2.71 g	Stage #1: With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1 h; Stage #2: at 0℃; for 0.25 h;	To a suspension of NaH (ca. 60wtpercent, 728 mg, 18.21 mmol) in THF (30 mL) and DMF (15 mL) at 0 °Cwas added a solution of the crude methyl ester in THF (30 mL) dropwise. After stirring at 0 °C for 1 h,MeI (2.06 mL, 33.11 mmol) was added dropwise. The reaction mixture was stirred at 0 °C for 15 min.The reaction was quenched successively with H2O (2 mL) and sat. aq. NH4Cl (6 mL). The layers wereseparated, and the aqueous layer was extracted with AcOEt (2 x 60 mL). The organic layers werecombined, washed with brine (60 mL), dried over MgSO4, and concentrated in vacuo. The residue waspurified by flash chromatography (silica gel, hexane/AcOEt = 10:1) to afford 26 (2.71 g, 81percent yield from3-indoleacetic acid) as a colorless oil.
1.4 g	With sodium hydride In tetrahydrofuran at 0 - 20℃; for 3 h;	To a stirred solution of 2-(1H-indol-3-yl)acetic acid (19-1) (3.0 g, 17.1 mmol) in DMF (20.0 mL ) was added K₂CO₃ (7.09 g, 51.3 mmol) and the reaction mixture was stirred for 15 minutes. Methyl iodide (3.19 mL, 51.3 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 16 hours. TLC showed formation of a new spot (Rf-0.5 in 20percent ethyl acetate/hexane). The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated. ¹HNMR and LCMS showed only the acid group was converted to its methyl ester, N-methylation didn't took place. The residue was again dissolved in THF (15.0 mL) and to it was added NaH (1.0 eq) at 0°C. MeI (1.0 eq) was then added to the reaction mixture and the reaction mixture was stirred at room temperature for 3 hours. TLC showed a new spot formation (Rf-0.6 in 10percent ethyl acetate/hexane). The reaction was diluted with cold water and ethyl acetate. The organic layer was separated and washed with water, brine, dried over sodium sulfate, concentrated and the resulting residue was purified by column chromatography (silica 100-200, 0percent-2percent ethyl acetate/hexane) to afford methyl 2-(1-methyl-1H-indol-3-yl)acetate 19-2 (1.40 g, 6.88 mmol, 40.3 percent) as a yellow oil. LC MS: ES+ 204.3.

Reference： [1] Organic letters, 2000, vol. 2, # 17, p. 2639 - 2641
[2] Tetrahedron Asymmetry, 2009, vol. 20, # 20, p. 2374 - 2389
[3] Journal of Organic Chemistry, 1980, vol. 45, # 16, p. 3172 - 3176
[4] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 13, p. 2843 - 2866
[5] Patent: US2015/353489, 2015, A1, . Location in patent: Paragraph 0240; 0241
[6] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4716 - 4722
[7] Patent: WO2004/7463, 2004, A1, . Location in patent: Page 183-184
[8] Patent: WO2005/5393, 2005, A2, . Location in patent: Page/Page column 183-184
[9] Patent: US2006/4195, 2006, A1, . Location in patent: Page/Page column 80
[10] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 2219 - 2224
[11] Organic Letters, 2010, vol. 12, # 21, p. 4956 - 4959
[12] Organic and Biomolecular Chemistry, 2012, vol. 10, # 10, p. 2101 - 2112
[13] Tetrahedron, 2013, vol. 69, # 45, p. 9481 - 9493
[14] Patent: WO2017/197046, 2017, A1, . Location in patent: Page/Page column 303

4
[ 87-51-4 ]
[ 616-38-6 ]
[ 1912-33-0 ]
[ 58665-00-2 ]

Reference： [1] Organic Process Research and Development, 2001, vol. 5, # 6, p. 604 - 608

5
[ 1912-33-0 ]
[ 24424-99-5 ]
[ 370562-34-8 ]

Reference： [1] European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4716 - 4722
[2] Tetrahedron, 2009, vol. 65, # 44, p. 9015 - 9020
[3] Tetrahedron, 2004, vol. 60, # 44, p. 10039 - 10047
[4] Tetrahedron Letters, 2000, vol. 41, # 32, p. 6149 - 6152
[5] Journal of Organic Chemistry, 2001, vol. 66, # 20, p. 6595 - 6603
[6] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4329 - 4339
[7] Journal of Organic Chemistry, 2011, vol. 76, # 2, p. 500 - 511
[8] Journal of Organic Chemistry, 2014, vol. 79, # 5, p. 2111 - 2114

6
[ 1912-33-0 ]
[ 152213-63-3 ]

Reference： [1] Chemistry Letters, 2011, vol. 40, # 10, p. 1079 - 1081

[ 1912-33-0 ] Synthesis Path-Downstream 1~19

1
[ 1912-33-0 ]
[ 526-55-6 ]

Yield	Reaction Conditions	Operation in experiment
96%	With lithium aluminium tetrahydride In tetrahydrofuran
81%	With isopropyl alcohol In hexane at 0 - 20℃; for 0.583333h; Inert atmosphere;
69%	With tetrabutylammonium borohydride In dichloromethane for 10h; Heating;

	With lithium aluminium tetrahydride; diethyl ether
	With lithium aluminium tetrahydride
	With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 2h;	19 EXAMPLE 19; 1-Acetyl-2,3-dihydro-3-[2-(methanesulphonyl)ethyl]-1H-indole, 19a To a solution of indole-3-acetic acid (100 g) in methanol (1 l) was added ether saturated with HCl (200 ml), and the solution was left at room temperature for 3 hours. The solution as evaporated in vacuo, and the residue was dissolved in THF 1.2 l) and added slowly with cooling to a stirred suspension of LiAlH4 (28.6 g) in THF (1 l). After stirring for 2 hours at room temperature, the mixture was cooled in an ice bath, and water (57 ml), 15% NaOH (29 ml), and water (143 ml) was added. The mixture was filtered and evaporated in vacuo, and the residue (84.9 g) was dissolved in dioxane (1.5 l). Borane trimethylamine complex (200 g) was added, and to the stirred mixture was added concentrated hydrochloric acid (150 ml) during 1 hour. The mixture was heated to 40° C. for 30 minutes and then to reflux for 2.5 hours. Then 6 M hydrochloric acid (460 ml) was added and reflux was continued for 30 minutes. The solution was concentrated in vacuo, and the residue was poured on ice. The solution was washed with ether and was made basic with concentrated NaOH and then extracted with ether. The organic phase was dried over MgSO4 and was evaporated in vacuo. The residue was dissolved in CH2Cl2 (680 ml) and triethylamine (68 ml). Acetyl chloride (36 ml) was added at 5° C. during 1 hour. After further stirring for 1 hour at room temperature, the mixture was washed with dilute hydrochloric acid, and NaHCO3 solution. After drying over MgSO4 and evaporation in vacuo, the residue was dissolved in methanol (500 ml), and 30% Na-methanolat (10 ml) was added. The mixture was stirred for 4 hours at room temperature and was then evaporated in vacuo and was dissolved in CH2Cl2 and was washed with saturated NaCl solution, dried over MgSO4 and evaporation in vacuo. The residue (75.4 g) was dissolved in CH2Cl2 (1 l) and triethylamine (100 ml). With cooling was added a solution of methanesulphonic chloride (27 ml) in CH2Cl2 (175 ml) at 10° C. After stirring for 30 minutes at 0° C. and 1 hour at room temp the mixture was evaporated in vacuo and was purified on silica gel eluted with ethyl acetate to give the title product as an oil (74 g).
72 %Chromat.	Stage #1: Indole-3-acetic acid methyl ester With diethoxymethylane; zinc diacetate In tetrahydrofuran at 65℃; for 24h; Inert atmosphere; Stage #2: With methanol; potassium hydroxide chemoselective reaction;
	With diisobutylaluminium hydride In tetrahydrofuran; toluene at 20℃;

Reference： [1]Zarezin, Danil P.; Shmatova, Olga I.; Kabylda, Adil M.; Nenajdenko, Valentine G. [European Journal of Organic Chemistry, 2018, vol. 2018, # 34, p. 4716 - 4722]
[2]An, Jie; Work, D. Neil; Kenyon, Craig; Procter, David J. [Journal of Organic Chemistry, 2014, vol. 79, # 14, p. 6743 - 6747]
[3]Wakamatsu, Takeshi; Inaki, Harumi; Ogawa, Akemi; Watanabe, Masako; Ban, Yoshio [Heterocycles, 1980, vol. 14, # 10, p. 1441 - 1444]
[4]Vitali; Mossini [Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 84,86] Fish et al. [Journal of the American Chemical Society, 1956, vol. 78, p. 3668,3670]
[5]Alvarez, Ricardo G.; Hunter, Iain S.; Suckling, Colin J.; Thomas, Michael; Vitinius, Ute [Tetrahedron, 2001, vol. 57, # 40, p. 8581 - 8587]
[6]Current Patent Assignee: H. LUNDBECK A/S - US6352988, 2002, B2 Location in patent: Page column 28-29
[7]Location in patent: experimental part Das, Shoubhik; Moeller, Konstanze; Junge, Kathrin; Beller, Matthias [Chemistry - A European Journal, 2011, vol. 17, # 27, p. 7414 - 7417]
[8]Location in patent: experimental part Revelant, Germain; Dunand, Sandrine; Hesse, Stephanie; Kirsch, Gilbert [Synthesis, 2011, # 18, p. 2935 - 2940]

2
[ 1912-33-0 ]
[ 879-37-8 ]

Reference： [1]Journal of the Chemical Society,1952,p. 650,658

3
[ 1912-33-0 ]
[ 5448-47-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With hydrazine hydrate In methanol at 60℃;	3.1 Example 3: 2-(5-((lH-indol-3-yl)methyl)-4-butyl-4H-l,2,4-triazol-3-yl)-5-(4-methylpiperazin- l-yl)-l,3,4-thiadiazole. 0115] Step 1. General procedure for preparation of Intermediate 15. 15 A solution of methyl 2-(lH-indol-3-yl)acetate (20.0 g, 0.106 mol), and ΝΗ2ΝΗ2·Η20 (12.5 g, 0.53 mol) in MeOH (200 mL) was stirred at 60 °C overnight. TLC Rf 0.5 (petroleum ether/EtOAc, 4/1) showed the reaction was complete. The reaction mixture was concentrated and CH2CI2 was added to the residue to recrystallize the product. The mixture was filtered and the filter cake was dried by vacuum at 50 °C to give Intermediate 15 (20 g, 100%) as yellow solid. 1H NMR (400 MHz, MeOD) δ 3.61 (s, 2H), 6.99-7.02 (m, 1H), 7.07-7.11 (m, 1H), 7.15 (s, 1H), 7.32-7.34 (d, J = 8.4 Hz, 1H), 7.53-7.55 (d, J = 8.0 Hz, 1H).
87%	With hydrazine hydrate Microwave irradiation;	Microwave-assisted synthesis of intermediate 3 General procedure: Compound 2 (5 mmol) was added to hydrazine- hydrate (80) (3 mL)at room temperature, and the mixture was irradiated continually for 5-8 min at 300 W. The reaction progress was monitored by TLC. After the reaction was complete and the mixture was sufficiently cooled, intermediate 3 (yield 83-98) was formed.
85%	With hydrazine In methanol

68%	With hydrazine hydrate In ethanol for 28h; Heating;
66%	With hydrazine hydrate In ethanol for 6h; Heating;
60%	With hydrazine In ethanol Reflux;
59%	With hydrazine hydrate In ethanol Heating;
	With water; hydrazine hydrate
	With ethanol; hydrazine hydrate
9.2 g	With hydrazine hydrate In 1,2-dimethoxyethane at 115℃; for 20h;	1.2 (2) in a 500 ml round bottom flask methyl indole acetic acid is added in 9.46g (48mmol), ethylene glycol monomethyl ether (40 ml), 5 ml of hydrazine hydrate, 115 °C heating reflux reaction about 20 hours, thin layer chromatography (TLC) detecting raw material point dematerialised, stop the reaction, cooling to room temperature, adding water (50 ml), static separating white solid, filtering to get the crude product, using ethanol is recrystallized to get indole acetic acid hydrazide white solid 9.2 g.
	With hydrazine hydrate In ethanol for 3h; Reflux;
	With hydrazine hydrate In methanol; water for 16h; Reflux;
	With hydrazine hydrate In methanol for 6h; Reflux;	4.2. General procedure for the synthesis of indolederivatives (1-22) Indole derivatives were synthesized by refluxing methyl 2-(1H-indol-3-yl) acetate (5 mmol) with hydrazine hydrate (5 mL) in methanol (15 mL) for 6 hrs yielded 2-(1H-indol-3-yl)acetohydrazide as intermediate product (I). The completionof reaction was monitored using TLC. The excess solventwere evaporated under vacuum to obtain the crude productand recrystallized in methanol to obtained pure product.Equimolar intermediate product (I) then further treated withdifferent aldehydes (1-22) in methanol (15 mL) for 3-4 hrs inthe presence of catalytic amount of acetic acid yieldedindole derivatives (1-22). The completion of reaction wasmonitored with the help of TLC. The crude was then recrystallizedin methanol to obtained pure product (Hanna et al.,2007; Ju et al., 2019; Liu et al., 2019; Mirfazli et al., 2016). 4.3. 2-(1h-indol-3-yl)-N’-(4-nitrobenzylidene)acetohydrazide (1)Yield: (88%); mp 289-291 C match (Hanna et al., 2007; Juet al., 2019; Liu et al., 2019; Mirfazli et al., 2016); 1HNMR;(400 MHz, DMSO-d6): d 11.70 (s, 1H, NH), 11.52 (s, 1H, NH),8.70 (s, 1H), 8.36 (d, 2H, J8.0 Hz), 7.89 (d, 2H, J8.0 Hz),7.60 (t, 1H, J7.0 Hz), 7.22 (d, 1H, J7.5 Hz), 6.92-6.86 (m,3H), 3.69 (s, 2H, CH2);13CNMR (100, MHz, DMSO) d171.0,150.5, 144.3, 139.5, 136.3, 127.2, 125.0, 125.0, 124.2,124.2, 123.5, 121.4, 119.5,118.6, 111.2, 109.5, 36.0, HR-EIMSm/z, calcd for C17H14N4O3 [M] 322.1066 found 322.1053.

Reference： [1]Current Patent Assignee: UCB - WO2014/14937, 2014, A1 Location in patent: Paragraph 0115
[2]Ye, Ying; Suo, Yourui; Yang, Fang; Yang, Yongjing; Han, Lijuan [Journal of Chemical Research, 2015, vol. 39, # 5, p. 296 - 299]
[3]Yar, Muhammad; Bajda, Marek; Mehmood, Rana Atif; Sidra, Lala Rukh; Ullah, Nisar; Shahzadi, Lubna; Ashraf, Muhammad; Ismail, Tayaba; Shahzad, Sohail Anjum; Khan, Zulfiqar Ali; Naqvi, Syed Ali Raza; Mahmood, Nasir [Letters in drug design and discovery, 2014, vol. 11, # 3, p. 331 - 338]
[4]Khan, Khalid Mohammed; Rahat, Shagufta; Choudhary, Muhammad Iqbal; Atta-ur-Rahman; Ghani, Usman; Perveen, Shahnaz; Khatoon, Shagufta; Dar, Ahsana; Malik, Abdul [Helvetica Chimica Acta, 2002, vol. 85, # 2, p. 559 - 570]
[5]Kelarev; Shvekhgeimer [Chemistry of Heterocyclic Compounds, 1982, vol. 18, # 3, p. 258 - 261]
[6]Yar, Muhammad; Sidra, Lala Rukh; Pontiki, Eleni; Mushtaq, Nafeesa; Ashraf, Muhammad; Nasar, Rumana; Khan, Islam Ullah; Mahmood, Nasir; Naqvi, Syed Ali Raza; Khan, Zulfiqar Ali; Shahzad, Sohail Anjum [Journal of the Iranian Chemical Society, 2014, vol. 11, # 2, p. 369 - 378]
[7]Demange, Luc; Boeglin, Damien; Moulin, Aline; Mousseaux, Delphine; Ryan, Joanne; Bergé, Gilbert; Gagne, Didier; Heitz, Annie; Perrissoud, Daniel; Locatelli, Vittorio; Torsello, Antonio; Galleyrand, Jean-Claude; Fehrentz, Jean-Alain; Martinez, Jean [Journal of Medicinal Chemistry, 2007, vol. 50, # 8, p. 1939 - 1957]
[8]Katritzky [Journal of the Chemical Society, 1955, p. 2586,2591] Yale et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 1933,1934] Tanaka [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 362,365; dtsch. Ref. S. 143][Chem.Abstr., 1941, p. 1481]
[9]Katritzky [Journal of the Chemical Society, 1955, p. 2586,2591] Yale et al. [Journal of the American Chemical Society, 1953, vol. 75, p. 1933,1934] Tanaka [Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1940, vol. 60, p. 362,365; dtsch. Ref. S. 143][Chem.Abstr., 1941, p. 1481]
[10]Current Patent Assignee: YUNNAN UNIVERSITY; KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY - CN105732468, 2016, A Location in patent: Paragraph 0068
[11]Eldehna, Wagdy M.; Hassan, Ghada S.; Al-Rashood, Sara T.; Alkahtani, Hamad M.; Almehizia, Abdulrahman A.; Al-Ansary, Ghada H. [Marine Drugs, 2020, vol. 18, # 4]
[12]Iškauskienė, Monika; Kadlecová, Alena; Voller, Jiří; Janovská, Lucie; Malinauskienė, Vida; Žukauskaitė, Asta; Šačkus, Algirdas [Archiv der Pharmazie, 2021, vol. 354, # 6]
[13]Taha, Muhammad; Ismail, Sukinah; Imran, Syahrul; Almandil, Noor Barak; Alomari, Munther; Rahim, Fazal; Uddin, Nizam; Hayat, Shawkat; Zaman, Khalid; Ibrahim, Mohamad; Alghanem, Bandar; Islam, Imadul; Farooq, Rai Khalid; Boudjelal, Mohamed; Khan, Khalid Mohammed [Journal of Biomolecular Structure and Dynamics, 2021]

4
[ 85676-99-9 ]
[ 17697-12-0 ]
[ 1912-33-0 ]
[ 1666-13-3 ]
(2-Phenylselanyl-1H-indol-3-yl)-acetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 29% 2: 89%	In tetrahydrofuran for 2h;

Reference： [1]Barton, Derek H. R.; Lusinchi, Xavier; Milliet, Pierre [Tetrahedron, 1985, vol. 41, # 21, p. 4727 - 4738]

5
[ 1912-33-0 ]
[ 74-88-4 ]
[ 58665-00-2 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 6h;	N-Methyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, methyl iodide (223 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-methyl-3-indoleacetic acid methyl ester (140 mg, yield: 65%); 1H NMR (400 MHz, CDCl3): delta 7.60 (d, J=7.9 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 7.9 Hz, 1H), 7.12 (dd, J=8.2, 7.9 Hz, 1H), 7.03 (s, 1H), 3.75 (s, 3H), 3.77 (s, 2H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 172.6, 136.9, 127.7, 121.7 (2C), 119.26, 118.9, 109.3, 106.8, 51.9, 32.7, 31.0.
65%	With sodium hydride; In N,N-dimethyl-formamide; at 20℃; for 6h;Inert atmosphere;	N-Methyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, methyl iodide (223 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain N-methyl-3-indoleacetic acid methyl ester (140 mg, yield: 65%); 1H NMR (400 MHz, CDCl3): delta 7.60 (d, J=7.9 Hz, 1H), 7.29 (d, J=8.2 Hz, 1H), 7.23 (dd, J=8.2, 7.9 Hz, 1H), 7.12 (dd, J=8.2, 7.9 Hz, 1H), 7.03 (s, 1H), 3.75 (s, 3H), 3.77 (s, 2H), 3.69 (s, 3H); 13C NMR (100 MHz, CDCl3): delta 172.6, 136.9, 127.7, 121.7 (2C), 119.26, 118.9, 109.3, 106.8, 51.9, 32.7, 31.0.
19%		To a suspension of sodium hydride (104 mg, 7.61 [MMOL)] in DMF (11 mL) was added a solution of 1 H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 [MMOL)] in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 [MMOL).] The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3 x 100 mL). The combined organic layers were dried with [NA2SO4,] and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19%) of [(1-METHYL-1H-INDOL-3-YL)-ACETIC] acid methyl ester after purification. HPLC: Rt = 8.91 (Method A). MS (ES+): mass calculated for [C12H13NO2,] 203.09 ; m/z found 204.09 [[M+H] +. 1H] NMR (400 MHz, [CDCI3)] : 7.60 (d, J = 7.9 Hz, [1 H),] 7.30 (d, [J =] 8.2 Hz, 1 H), 7.23 (t, J = 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 [(S,] [1 H),] 3.77 (s, 2H), 3.76 (s, [3H),] 3.69 (s, 3H).

19%		To a suspension of20 sodium hydride (104 mg, 7.61 mmol) in DMF (11 ml) was added a solution of1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 ml). Themixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8mmol). The reaction mixture was stirred for an additional 18 h, quenched,diluted with saturated ammonium chloride (200 ml), and then extracted with25 diethyl ether (3 x 100 ml). The combined organic layers were dried withNasSCU, and the solvent was removed under reduced pressure. The cruderesidue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg(19%) of (1 -methyl-1 H-indol-3-yl)-acetic acid methyl ester after purification.HPLC: Rt = 8.91 (Method A). MS (ES+): mass calculated for C12H13NO2, 203.09; m/z found 204.09 [M+Hf. 1H NMR (400 MHz, CDCI3): 7.60 (d, J= 7.9Hz, 1H), 7.30 (d, J= 8.2 Hz, 1H), 7.23 (t, J= 8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H),7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).
19%	With sodium hydride; In DMF (N,N-dimethyl-formamide); for 19h;	A. (1-Methyl-1H-indol-3-yl)-acetic acid methyl ester. To a suspension of sodium hydride (104 mg, 7.61 mmol) in DMF (11 mL) was added a solution of 1H-indol-3-yl-acetic acid methyl ester (0.50 g, 2.6 mmol) in DMF (5.0 mL). The mixture was stirred for 1 h followed by addition of methyl iodide (1.1 g, 7.8 mmol). The reaction mixture was stirred for an additional 18 h, quenched, diluted with saturated ammonium chloride (200 mL), and then extracted with diethyl ether (3*100 mL). The combined organic layers were dried with Na2SO4, and the solvent was removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexanes) giving 100 mg (19%) of (1-methyl-1H-indol-3-yl)-acetic acid methyl ester after purification. HPLC: Rt=8.91 (Method A). MS (ES+): mass calculated for Cl2H13NO2, 203.09; m/z found 204.09 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.60 (d, J=7.9 Hz, 1H), 7.30 (d, J=8.2 Hz, 1H), 7.23 (t, J=8.2 Hz, 1H), 7.13 (t, 7.4 Hz, 1H), 7.04 (s, 1H), 3.77 (s, 2H), 3.76 (s, 3H), 3.69 (s, 3H).
2.71 g		To a suspension of NaH (ca. 60wt%, 728 mg, 18.21 mmol) in THF (30 mL) and DMF (15 mL) at 0 Cwas added a solution of the crude methyl ester in THF (30 mL) dropwise. After stirring at 0 C for 1 h,MeI (2.06 mL, 33.11 mmol) was added dropwise. The reaction mixture was stirred at 0 C for 15 min.The reaction was quenched successively with H2O (2 mL) and sat. aq. NH4Cl (6 mL). The layers wereseparated, and the aqueous layer was extracted with AcOEt (2 x 60 mL). The organic layers werecombined, washed with brine (60 mL), dried over MgSO4, and concentrated in vacuo. The residue waspurified by flash chromatography (silica gel, hexane/AcOEt = 10:1) to afford 26 (2.71 g, 81% yield from3-indoleacetic acid) as a colorless oil.
1.4 g	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 3h;	To a stirred solution of 2-(1H-indol-3-yl)acetic acid (19-1) (3.0 g, 17.1 mmol) in DMF (20.0 mL ) was added K2CO3 (7.09 g, 51.3 mmol) and the reaction mixture was stirred for 15 minutes. Methyl iodide (3.19 mL, 51.3 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 16 hours. TLC showed formation of a new spot (Rf-0.5 in 20% ethyl acetate/hexane). The reaction was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate and concentrated. 1HNMR and LCMS showed only the acid group was converted to its methyl ester, N-methylation didn't took place. The residue was again dissolved in THF (15.0 mL) and to it was added NaH (1.0 eq) at 0C. MeI (1.0 eq) was then added to the reaction mixture and the reaction mixture was stirred at room temperature for 3 hours. TLC showed a new spot formation (Rf-0.6 in 10% ethyl acetate/hexane). The reaction was diluted with cold water and ethyl acetate. The organic layer was separated and washed with water, brine, dried over sodium sulfate, concentrated and the resulting residue was purified by column chromatography (silica 100-200, 0%-2% ethyl acetate/hexane) to afford methyl 2-(1-methyl-1H-indol-3-yl)acetate 19-2 (1.40 g, 6.88 mmol, 40.3 %) as a yellow oil. LC MS: ES+ 204.3.

Reference： [1]Organic letters,2000,vol. 2,p. 2639 - 2641
[2]Tetrahedron Asymmetry,2009,vol. 20,p. 2374 - 2389
[3]Journal of Organic Chemistry,1980,vol. 45,p. 3172 - 3176
[4]Bioorganic and Medicinal Chemistry,2003,vol. 11,p. 2843 - 2866
[5]Patent: US2015/353489,2015,A1 .Location in patent: Paragraph 0240; 0241
[6]Patent: US2019/224165,2019,A1 .Location in patent: Paragraph 0093; 0094; 0219-0220
[7]European Journal of Organic Chemistry,2018,vol. 2018,p. 4716 - 4722
[8]Patent: WO2004/7463,2004,A1 .Location in patent: Page 183-184
[9]Patent: WO2005/5393,2005,A2 .Location in patent: Page/Page column 183-184
[10]Patent: US2006/4195,2006,A1 .Location in patent: Page/Page column 80
[11]Journal of the Chemical Society. Perkin transactions I,1983,p. 2219 - 2224
[12]Organic Letters,2010,vol. 12,p. 4956 - 4959
[13]Organic and Biomolecular Chemistry,2012,vol. 10,p. 2101 - 2112
[14]Tetrahedron,2013,vol. 69,p. 9481 - 9493
[15]Patent: WO2017/197046,2017,A1 .Location in patent: Page/Page column 303

6
[ 1912-33-0 ]
[ 2591-98-2 ]

Reference： [1]Tetrahedron,1985,vol. 41,p. 2109 - 2114
[2]Journal of the American Chemical Society,2008,vol. 130,p. 933 - 944
[3]Synthesis,2011,p. 2935 - 2940
[4]Chemistry - An Asian Journal,2016,vol. 11,p. 390 - 394
[5]European Journal of Organic Chemistry,2018,vol. 2018,p. 4716 - 4722

7
[ 700-06-1 ]
[ 1912-33-0 ]
[ 114648-66-7 ]
[ 92001-33-7 ]

Reference： [1]Journal of Chemical Research, Miniprint,1984,p. 1578 - 1586

8
[ 1912-33-0 ]
[ 24424-99-5 ]
[ 370562-34-8 ]

Yield	Reaction Conditions	Operation in experiment
78%	With dmap; triethylamine; In dichloromethane; at 20℃; for 16h;	As shown in Fig. 24K, to a solution of compound 1 (20 g, 0.106 mol, 1.0 eq) in DCM (20 mL) was successively added B C O (24.4 g, 0.112 mol, 1.056 eq), DMAP (646 mg, 5.29 mmol, 0.05 eq) and TEA (534 mg, 5.29 mmol, 0.05 eq). The mixture was stirred at room temperature for 16 h. TLC analysis of the reaction mixture showed full conversion to the desired product. Then the mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography to afford compound 2 (24 g, 78%).

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 4716 - 4722
[2]Tetrahedron,2009,vol. 65,p. 9015 - 9020
[3]Tetrahedron,2004,vol. 60,p. 10039 - 10047
[4]Patent: WO2019/200232,2019,A1 .Location in patent: Paragraph 0932
[5]Tetrahedron Letters,2000,vol. 41,p. 6149 - 6152
[6]Journal of Organic Chemistry,2001,vol. 66,p. 6595 - 6603
[7]Journal of Medicinal Chemistry,2007,vol. 50,p. 4329 - 4339
[8]Journal of Organic Chemistry,2011,vol. 76,p. 500 - 511
[9]Journal of Organic Chemistry,2014,vol. 79,p. 2111 - 2114

9
[ 87-51-4 ]
[ 1912-33-0 ]
[ 58665-00-2 ]
[ 616-38-6 ]
[ 23304-43-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide;	Example 17 Preparation of 1-methylindole-3acetic acid methyl ester and 1-indole-3-acetic acid methyl ester. To a three-necked round bottom flask was charged indole-3-acetic acid (3.0 g, 17.12 mmol), potassium carbonate (powder, 1.5 g), N,N-dimethylformamide (20 mL) and dimethyl carbonate (4.3 mL, 51.07 mmol). The resulting mixture was heated to reflux (~130 C.) for 6 h at which time analysis of the reaction by HPLC indicated the starting material had been consumed. After the reaction mixture was cooled to room temperature, it was partitioned between water (50 mL) and tert-butyl methyl ether (60 mL). The separated organic layer was washed with water (2*50 mL) and the solvent was evaporated under reduced pressure. The crude product, shown by HPLC analysis to contain 1-methylindole-3-acetic acid methyl ester (89%) and 1-indole-3-acetic acid methyl ester (8%), was separated into the individual components by using column chromatography over silica gel. Total yield 3.2 g, 2.8 g for 1-methylindole-3-acetic acid methyl ester and 0.40 g for 1-indole-3-acetic acid methyl ester.

Reference： [1]Patent: US6326501,2001,B1

10
[ 67-56-1 ]
[ 526-55-6 ]
[ 1912-33-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	With water; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 110℃; for 24h;

Reference： [1]Owston, Nathan A.; Parker, Alexandra J.; Williams, Jonathan M. J. [Chemical Communications, 2008, vol. 8, # 5, p. 624 - 625]

11
[ 1912-33-0 ]
[ 152213-63-3 ]

Reference： [1]Chemistry Letters,2011,vol. 40,p. 1079 - 1081

12
[ 1912-33-0 ]
[ 1218918-62-7 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 2299 - 2309

13
[ 19213-72-0 ]
[ 1912-33-0 ]
[ 157496-76-9 ]

Reference： [1]Angewandte Chemie - International Edition,2012,vol. 51,p. 8304 - 8308

14
[ 1912-33-0 ]
[ 2532-74-3 ]

Reference： [1]Tetrahedron,2013,vol. 69,p. 9481 - 9493

15
[ 87-51-4 ]
[ 616-38-6 ]
[ 1912-33-0 ]
[ 58665-00-2 ]

Reference： [1]Organic Process Research and Development,2001,vol. 5,p. 604 - 608

16
[ 87-51-4 ]
[ 119-36-8 ]
[ 1912-33-0 ]
[ 69-72-7 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: indole-3-acetic acid With potassium carbonate In N,N-dimethyl acetamide at 110℃; for 0.5h; Stage #2: methyl salicylate at 110℃; for 24h;	Methyl 2-Methoxybenzoate (3a); Typical Procedure General procedure: A mixture of 2-methoxybenzoic acid (3.8 g, 25 mmol) and K2CO3 (2.07 g, 15 mmol) in DMA (50 mL) was stirred at 110 °C for 0.5 h. Methyl salicylate (5.70 g, 37.5 mmol) was added and the resulting mixture was stirred for 24 h. The solvent was then removed in vacuo. After cooling to r.t., K2CO3 (2.42 g, 17.5 mmol) and water (50mL) were added to hydrolyze the excess methyl salicylate. The resulting mixture was heated at 60 °C until methyl salicylate disappeared on TLC. Then, the solution was extracted with EtOAc (3 ×20 mL). The organic layer was washed with water, sat. aq NaCl solution,and dried (anhyd MgSO4). Evaporation of solvent in vacuoafforded methyl 2-methoxybenzoate (3.82 g, 92%). More than 90% of salicylic acid was recovered as a white precipitate by acidifying the aqueous phase with 1 M HCl.

Reference： [1]Chen, Si; Jia, Lei; Li, Xiaonan; Luo, Meiming [Synthesis, 2014, vol. 46, # 2, p. 263 - 268]

17
[ 1912-33-0 ]
[ 638-45-9 ]
N-hexyl-3-indoleacetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	1 N-Hexyl-3-indoleacetic acid methyl ester N-Hexyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.
51%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Hexyl-3-indoleacetic acid methyl ester N-Hexyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): δ 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.
51%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Hexyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.

With hydrogenchloride

N-Hexyl-3-indoleacetic Acid Methyl Ester N-Hexyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, hexyl iodide (334 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-hexyl-3-indoleacetic acid methyl ester (147 mg, yield: 51%); 1H NMR (400 MHz, CDCl3): δ 7.60 (d, J=7.8 Hz, 1H) 7.31, (d, J=8.2 Hz, 1H), 7.20 (ddd, J=8.6, 5.6 Hz, 1H), 7.11 (ddd, J=8.0, 7.3 Hz, 1H), 7.08 (s, 2H), 4.06 (t, J=7.2 Hz, 2H), 3.77 (s, 2H), 3.69 (s, 3H), 1.81 (m, 2H), 1.30 (m, 6H), 0.87 (t, J=6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3): 172.6, 136.1, 127.7, 126.7, 121.5, 119.0, 119.0, 109.4, 106.6, 51.9, 46.3, 31.4, 31.1, 30.2, 22.6, 22.5, 14.0.

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - US2015/353489, 2015, A1 Location in patent: Paragraph 0256; 0257
[2]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2019/224165, 2019, A1 Location in patent: Paragraph 0093; 0094; 0235-0236
[3]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1 Location in patent: Paragraph 0084-0085; 0228-0229
[4]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1

18
[ 1912-33-0 ]
[ 4282-40-0 ]
N-heptyl-3-indoleacetic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h;	1 N-Heptyl-3-indoleacetic acid methyl ester N-Heptyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was acidified (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with brine and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl4): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.
49%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Heptyl-3-indoleacetic acid methyl ester N-Heptyl-3-indoleacetic acid methyl ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl3): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.
49%	With sodium hydride In N,N-dimethyl-formamide at 20℃; for 6h; Inert atmosphere;	1 N-Heptyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl3): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.

With hydrogenchloride

N-Heptyl-3-indoleacetic Acid Methyl Ester N-Heptyl-3-indoleacetic Acid Methyl Ester 3-Indoleacetic acid methyl ester (200 mg, 1.1 mmol) was dissolved in N,N-dimethylformamide (3 mL). To the solution, sodium hydride (60 mg) was added. To this solution, heptyl iodide (358 mg, 1.58 mmol) was added, and the mixture was stirred at room temperature for 6 hours. After the reaction was confirmed by TLC to be complete, the reaction solution was rendered acidic (pH=3 to 4) by the addition of 6 N hydrochloric acid, and water (5 ml) was added thereto, followed by extraction with ethyl acetate (5 ml) three times. The organic layer was washed twice with saturated saline and dehydrated over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then, the residue was purified using silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain N-heptyl-3-indoleacetic acid methyl ester (148 mg, yield: 49%); 1H NMR (400 MHz, CDCl3): δ 3.69 (3H, s), 7.60 (1H, d, J=7.8), 7.31 (1H, d, J=8.2) 7.11 (1H, dd, J=8.2, 6.7), 7.08 (1H, s), 4.06 (2H, t, J=7.1), 3.77 (2H, s) 3.59 (1H, dd, J=8.2, 6.7), 1.82 (2H, m), 1.29 (8H, m), 0.87 (3H, t, J=7.1); 13C NMR (100 MHz, CDCl3): δ 172.57, 136.16, 127.70, 126.66, 121.54, 118.98, 118.98, 109.43, 106.64, 51.89, 46.31, 31.67, 31.11, 30.24, 28.89, 26.96, 22.55, 14.02.

Reference： [1]Current Patent Assignee: TOHOKU UNIVERSITY - US2015/353489, 2015, A1 Location in patent: Paragraph 0260; 0261
[2]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2019/224165, 2019, A1 Location in patent: Paragraph 0093; 0094; 0239-0240
[3]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1 Location in patent: Paragraph 0084-0085; 0232-0233
[4]Current Patent Assignee: KAKE EDUCATIONAL INSTITUTION; TOHOKU UNIVERSITY - US2022/106270, 2022, A1

19
[ 67-56-1 ]
[ 1912-33-0 ]
[ 558-13-4 ]
[ 156362-00-4 ]

Yield	Reaction Conditions	Operation in experiment
51%	With Ru(2,2'-bipyridine)3(PF₆)2*H₂O; diisopropylamine at 20℃; for 21h; Schlenk technique; Inert atmosphere; Irradiation; regioselective reaction;

Reference： [1]Yang, Qing-Qing; Marchini, Marianna; Xiao, Wen-Jing; Ceroni, Paola; Bandini, Marco [Chemistry - A European Journal, 2015, vol. 21, # 50, p. 18052 - 18056]

Recommend Products

Same Skeleton Products

Related Products

Isomers

Technical Information

• Acyl Group Substitution • Alcohols Convert Acyl Chlorides into Esters • Alcoholysis of Anhydrides • Amines Convert Esters into Amides • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Ester Cleavage • Ester Hydrolysis • Grignard Reagents Transform Esters into Alcohols • Hantzsch Pyridine Synthesis • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Specialized Acylation Reagents-Carbodiimides and Related Reagents • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification

Historical Records

Related Functional Groups of
[ 1912-33-0 ]

Esters

[ 778-82-5 ]

Ethyl 2-(1H-indol-3-yl)acetate

Similarity: 0.96

[ 5548-09-4 ]

Methyl 3-(1H-indol-3-yl)propanoate

Similarity: 0.96

[ 58665-00-2 ]

Methyl 2-(1-methyl-1H-indol-3-yl)acetate

Similarity: 0.95

[ 5622-50-4 ]

Methyl 2-(1,2,3,4-tetrahydroquinolin-6-yl)acetate

Similarity: 0.90

[ 942-24-5 ]

Methyl indole-3-carboxylate

Similarity: 0.88

Related Parent Nucleus of
[ 1912-33-0 ]

Indoles

[ 778-82-5 ]

Ethyl 2-(1H-indol-3-yl)acetate

Similarity: 0.96

[ 5548-09-4 ]

Methyl 3-(1H-indol-3-yl)propanoate

Similarity: 0.96

[ 58665-00-2 ]

Methyl 2-(1-methyl-1H-indol-3-yl)acetate

Similarity: 0.95

[ 1912-47-6 ]

2-(5-Methyl-1H-indol-3-yl)acetic acid

Similarity: 0.91

[ 1912-43-2 ]

2-Methylindole-3-acetic acid

Similarity: 0.89

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	Inquiry	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price) ]}	{[ item.pr_usastock ]}		{[ item.pr_chinastock ]}	{[ item.pr_remark ]}

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
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. 1912-33-0 ] {[proInfo.proName]}

Quality Control of [ 1912-33-0 ]

Related Doc. of [ 1912-33-0 ]

Product Details of [ 1912-33-0 ]

Calculated chemistry of [ 1912-33-0 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 1912-33-0 ]

Application In Synthesis of [ 1912-33-0 ]

[ 1912-33-0 ] Synthesis Path-Upstream 1~6

[ 1912-33-0 ] Synthesis Path-Downstream 1~19

Technical Information

Related Functional Groups of [ 1912-33-0 ]

Esters

Related Parent Nucleus of [ 1912-33-0 ]

Indoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 1912-33-0 ]

Related Parent Nucleus of
[ 1912-33-0 ]