16176-74-2|2-(1H-Indol-4-yl)acetic acid| Ambeed

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Quality Control of [ 16176-74-2 ] Purity: 98% SDS Specification

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Product Details of [ 16176-74-2 ]

CAS No. :	16176-74-2
Formula :	C₁₀H₉NO₂
M.W :	175.18
SMILES Code :	OC(=O)CC1=C2C=CNC2=CC=C1
MDL No. :	MFCD09837549
InChI Key :	XYJNAOLVFGLFTJ-UHFFFAOYSA-N
Pubchem ID :	12553829

Safety of [ 16176-74-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P280-P305+P351+P338-P310

Computational Chemistry of [ 16176-74-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.1
Num. rotatable bonds	2
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	49.84
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	53.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	0.98
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.51
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.79
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.11
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.21
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.52

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.26
Solubility	0.968 mg/ml ; 0.00552 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.23
Solubility	1.02 mg/ml ; 0.00585 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-3.06
Solubility	0.153 mg/ml ; 0.000875 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.3 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.41

Application In Synthesis of [ 16176-74-2 ]

* 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.

Downstream synthetic route of [ 16176-74-2 ]

[ 16176-74-2 ] Synthesis Path-Downstream 1~35

1
[ 30933-66-5 ]
[ 16176-74-2 ]

References: [1]Chemische Berichte,1956,vol. 89,p. 270,277.

2
[ 107-10-8 ]
[ 16176-74-2 ]
[ 84401-06-9 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

3
[ 16176-74-2 ]
[ 75-04-7 ]
[ 84401-05-8 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

4
[ 16176-74-2 ]
[ 142-84-7 ]
[ 84401-09-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.
[2]Journal of Medicinal Chemistry,1981,vol. 24,p. 238 - 240.

5
[ 16176-74-2 ]
[ 124-40-3 ]
[ 84401-07-0 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

6
[ 16176-74-2 ]
[ 109-89-7 ]
[ 84401-08-1 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

7
[ 84401-14-9 ]
[ 16176-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

10
[ 16176-74-2 ]
[ 3300-51-4 ]
2-(1<i>H</i>-indol-4-yl)-<i>N</i>-(4-trifluoromethyl-benzyl)-acetamide [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2006,vol. 14,p. 4740 - 4749.

11
[ 16176-74-2 ]
[ 76149-15-0 ]

References: [1]Journal of Medicinal Chemistry,1981,vol. 24,p. 238 - 240.
[2]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

12
[ 2124-55-2 ]
[ 16176-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

13
[ 16176-74-2 ]
[ 84401-01-4 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

14
[ 16176-74-2 ]
[ 84401-03-6 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

15
[ 84401-11-6 ]
[ 16176-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

16
[ 344320-85-0 ]
[ 16176-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

17
[ 84401-13-8 ]
[ 16176-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

18
[ 84401-12-7 ]
[ 16176-74-2 ]

References: [1]Journal of Heterocyclic Chemistry,1982,vol. 19,p. 1195 - 1199.

19
[ 858232-89-0 ]
[ 16176-74-2 ]

References: [1]Chemische Berichte,1956,vol. 89,p. 270,277.

20
(1-acetyl-indol-4-yl)-acetaldehyde oxime [ No CAS ]
[ 16176-74-2 ]

References: [1]Chemische Berichte,1956,vol. 89,p. 270,277.

21
[ 16176-74-2 ]
N-(2,3-Dimethylphenyl)-4-indole carboxamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: Preparation of N-(2,3-Dimethylphenyl)-4-indole carboxamide (11) Starting with <strong>[16176-74-2]indole-4-acetic acid</strong> (0.20 g) the above compound was prepared using the method described in Step 1, of Example 1. NMR (300 MHz, CDCl3) delta 8.51 (1H, s), 7.83 (1H, s), 7.72 (1H, d, J=8 Hz), 7.65 (1H, d, J=8 Hz), 7.58 (1H, d, J=8 Hz), 7.37 (1H, t, J=3 Hz), 7.30 (1H, d, J=8 Hz), 7.18 (1H, t, J=8 Hz), 7.06 (2H, m), 2.35 (3H, s), 2.25 (3H, s).

References: [1]Patent: US5631280,1997,A .

22
[ 16176-74-2 ]
[ 502434-10-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6935 - 6948.

23
[ 16176-74-2 ]
[ 100-51-6 ]
1-(4-((2S)-4-methyl-3,4-dihydro-2H-1,4-benzoxazin-2-ylmethoxy)benzoyl)-1H-indol-4-yl acetic acid benzyl ester [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6935 - 6948.

24
[ 16176-74-2 ]
[ 100-51-6 ]
[ 1351163-97-7 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine; p-toluenesulfonyl chloride; In toluene; at 0 - 20℃; for 2.0h;	To a stirred solution of <strong>[16176-74-2]2-(1H-indol-4-yl)acetic acid</strong> 45 (11.0 g, 62.9 mmol) in pyridine (45 mL) were added benzyl alcohol (6.9 mL, 66.0 mmol) and a solution of p-toluenesulfonyl chloride (13.2 g, 69.2 mmol) in toluene (38 mL) at 0 °C. After stirring vigorously for 2 h at room temperature, the reaction mixture was diluted with water and extracted with MTBE (.x.2). The combined organic layers were washed with NaHCO3 aq, water and brine, dried over Na2SO4 and concentrated in vacuo to give 46 as a dark brown oil, which was used for the next reaction without further purification; TLC Rf = 0.45 (n-hexane/EtOAc, 2:1).

References: [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 6935 - 6948.

25
[ 16176-74-2 ]
[ 856782-91-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3079 - 3082.

26
[ 16176-74-2 ]
[ 1373432-69-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3079 - 3082.

27
[ 16176-74-2 ]
[ 1373432-66-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3079 - 3082.

28
[ 16176-74-2 ]
[ 75-08-1 ]
[ 1373432-56-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With dmap; dicyclohexyl-carbodiimide; In dichloromethane;	General procedure: indole-3-acetic acid (Ac10, 100 mg, 571 mumol) was dissolved in DCM (3.0 mL). To this solution was added DMAP (0.1 equivalents, 7 mg, 57.0 mumol), DCC (1.2 equivalents, 141 mg, 685 mumol) and ethanethiol (1.1 equivalents, 46 muL, 38.6 mg, 628 mumol). The mixture was stirred and monitored by TLC (15 percent EtOAc in hexane) until the starting material was consumed. The mixture was then filtered through celite and the solvent removed in vacuo. The product was purified by column chromatography (15 percent EtOAc in hexane) affording the thioester Te10 (125 mg, 571 mumol, 99 percent).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3079 - 3082.

29
[ 16176-74-2 ]
C₁₀H₁₁NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 2.0h;Inert atmosphere;	using a dry double-mouth bottle as a reaction container, 1.0 equivalent of Compound 1 is completely dissolved in an anhydrous tetrahydrofuran solution under nitrogen protection conditions.After stirring at 0 ° C for about 1 minute, 2.0 equivalents of lithium aluminum hydride was slowly added to the reaction solution, and stirring was continued for about 2 hours.After the TLC monitoring reaction of the raw materials was completed, carefully add an equal volume of ice water with lithium aluminum hydride and an equal volume of 1 M sodium hydroxide solution (ie, add 1 mL of ice water and 1 mL of 1 M sodium hydroxide solution), and then react with diatomaceous earth. The solid in the liquid is filtered off.The filtrate was extracted three times with ethyl acetate. The combined organic phases were extracted with brine.Dry over anhydrous sodium sulfate,Concentrated under reduced pressure to obtain crude product and purified by column chromatographyCompound 2 was obtained. (2) The yield of this step was 69percent, and the property of Compound 2 was a yellow liquid.

References: [1]Patent: CN108440376,2018,A .Location in patent: Paragraph 0035; 0036; 0039; 0040.

30
[ 16176-74-2 ]
C₁₀H₁₀ClNO [ No CAS ]

References: [1]Patent: CN108440376,2018,A .

31
[ 16176-74-2 ]
C₁₀H₁₀ClNO₂ [ No CAS ]

References: [1]Patent: CN108440376,2018,A .

32
[ 16176-74-2 ]
[ 139122-19-3 ]

References: [1]Patent: CN108440376,2018,A .

33
[ 16176-74-2 ]
[ 139122-20-6 ]

References: [1]Patent: CN108440376,2018,A .

34
[ 16176-74-2 ]
[ 91374-21-9 ]

References: [1]Patent: CN108440376,2018,A .

35
[ 16176-74-2 ]
[ 91374-20-8 ]

References: [1]Patent: CN108440376,2018,A .

Historical Records

Technical Information

• Arndt-Eistert Homologation • Hunsdiecker-Borodin Reaction • Passerini Reaction • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Carboxylic Acids • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Ugi Reaction

Related Functional Groups of
[ 16176-74-2 ]

Carboxylic Acids

A198576 [4662-03-7]

2-(2-Phenyl-1H-indol-3-yl)acetic acid

Similarity: 0.91

A362283 [32588-36-6]

Indole-2-acetic acid

Similarity: 0.87

A175020 [30448-16-9]

7-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.85

A243469 [209920-43-4]

6-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.85

A308491 [39689-58-2]

2-(1H-Indol-6-yl)acetic acid

Similarity: 0.85

Related Parent Nucleus of
[ 16176-74-2 ]

Indoles

A198576 [4662-03-7]

2-(2-Phenyl-1H-indol-3-yl)acetic acid

Similarity: 0.91

A362283 [32588-36-6]

Indole-2-acetic acid

Similarity: 0.87

A175020 [30448-16-9]

7-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.85

A243469 [209920-43-4]

6-Methyl-1H-indole-3-carboxylic acid

Similarity: 0.85

A308491 [39689-58-2]

2-(1H-Indol-6-yl)acetic acid

Similarity: 0.85

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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

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CAS No.: 16176-74-2

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