1912-43-2

Basic information

• Product Name: 2-METHYLINDOLE-3-ACETIC ACID
• Synonyms: IFLAB-BB F0345-1687;(2-METHYL-1H-INDOL-3-YL)-ACETIC ACID;2-METHYL-3-INDOLEACETIC ACID;2-METHYLINDOLE-3-ACETIC ACID;AKOS BC-0002;2-METHYLINDOLE-3-ACETIC ACID, 98+%;2-Me-IAA;2-METHYLINDOLE-3-ACETIC ACID(2MeIAA)
• CAS NO: 1912-43-2
• Molecular Formula: C₁₁H₁₁NO₂
• Molecular Weight: 189.21
• EINECS: -0
• Product Categories: Indoles and derivatives;Imidazol&Benzimidazole;Building Blocks;Heterocyclic Building Blocks;Indoles
• Mol File: 1912-43-2.mol
• Article Data: 9

Chemical Properties

• Melting Point: 205 °C (dec.)(lit.)
• Boiling Point: 418.158 °C at 760 mmHg
• Flash Point: 206.695 °C
• Appearance: /
• Density: 1.3 g/cm³
• Storage Temp.: 2-8°C(protect from light)
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 4.19±0.30(Predicted)
• BRN: 152701
• CAS DataBase Reference: 2-METHYLINDOLE-3-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2-METHYLINDOLE-3-ACETIC ACID(1912-43-2)
• EPA Substance Registry System: 2-METHYLINDOLE-3-ACETIC ACID(1912-43-2)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 22-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 1912-43-2(Hazardous Substances Data)

Usage

Description

2-METHYLINDOLE-3-ACETIC ACID, also known as 2-Methyl-3-indoleacetic acid, is a plant growth hormone derivative of Indole-3-acetic acid. It is characterized by its ability to induce cell division and cell elongation, which in turn promotes overall plant growth. The relative activity of this compound in enhancing growth (elongation) in plant cells has been evaluated and recognized for its potential applications in the agricultural industry.

Uses

Used in Agricultural Applications:
2-METHYLINDOLE-3-ACETIC ACID is used as a plant growth regulator for promoting plant growth. It facilitates cell division and elongation, leading to enhanced growth and development in various plant species. This makes it a valuable tool for improving crop yields and overall plant health in the agricultural industry.

InChI:InChI=1/C11H11NO2/c1-7-9(6-11(13)14)8-4-2-3-5-10(8)12-7/h2-5,12H,6H2,1H3,(H,13,14)

Synthetic route

Levulinic acid phenylhydrazone (588-60-3) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With hydrogenchloride; acetic acid for 4h; Heating;	87%
With zinc(II) chloride at 125℃;
With methanol; sulfuric acid

levulinic acid (123-76-2) + phenylhydrazine (100-63-0) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With acetic acid for 4h; Reflux;	78%

diazoacetic acid ethyl ester (623-73-4) + 2-methyl-1H-indole (95-20-5) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
at 200℃; Verseifen des entstandenen Aethylesters mit Kalilauge;

2-methyl-1H-indole (95-20-5) + formaldehyd (50-00-0) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With potassium cyanide; ethanol
With potassium cyanide; ethanol

ethyl (2-methylindol-3-yl)acetate (21909-49-9) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With potassium hydroxide
With water; sodium hydroxide for 21h; Reflux;	2.74 g

2-(2-methyl-1H-indol-3-yl)acetonitrile (4071-16-3) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With potassium hydroxide

2-methylgramine (37125-92-1) + sodium cyanide (143-33-9) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With ethanol

4,4'-(2,3-diphenyl-tetrazanediylidene)-di-valeric acid bis-(N'-phenyl-hydrazide) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With hydrogenchloride; ethanol

Ethyl 4-Phenylhydrazonopentanoate (3397-38-4) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With zinc(II) chloride at 140℃; Behandeln des entstandenen Aethylesters mit alkoh. Kalilauge;
With boron trifluoride diethyl etherate at 125℃; Erwaermen des Reaktionsprodukts mit wss. NaOH;

2-methyl-1H-indole-3-carbaldehyde (5416-80-8) + methyl methylsulfinylmethyl sulfide (33577-16-1) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With hydrogenchloride; N-benzyl-trimethylammonium hydroxide 1.) THF, reflux, 10 h, 2.) aq. ethanol, room temp., 1 h; Multistep reaction;

C18H17N3O4S → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran for 10h; Heating; Yield given;

ethyl bromoacetate (105-36-2) + 1-acetyl-2-methyl-indolin-3-one → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
ueber zwei Stufen;

2-methyl-1H-indole (95-20-5) + water → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 4 steps 1: diethyl ether / 0.33 h / 0 °C 2: sat. aq. NaHCO3 / diethyl ether / 0.5 h / Heating 3: methanol / 8 h / Heating 4: NaBH4 / tetrahydrofuran / 10 h / Heating View Scheme

(2-methyl-3-indolyl)glyoxyloyl chloride (22980-10-5) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: sat. aq. NaHCO3 / diethyl ether / 0.5 h / Heating 2: methanol / 8 h / Heating 3: NaBH4 / tetrahydrofuran / 10 h / Heating View Scheme

(2-methyl-indol-3-yl)-glyoxylic acid (62454-47-1) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / 8 h / Heating 2: NaBH4 / tetrahydrofuran / 10 h / Heating View Scheme

2-methyl-1H-indole (95-20-5) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous acetic acid 2: aqueous ethanol View Scheme
Multi-step reaction with 2 steps 1: ethyl magnesium iodide; diethyl ether / Behandeln der Reaktionsloesung mit Chloracetonitril 2: aqueous KOH View Scheme

levulinic acid (123-76-2) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethanol; concentrated H2SO4 2: methanol. KOH View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol / 24 h / Reflux 2: sodium hydroxide; water / 21 h / Reflux View Scheme

4-oxopentanoic acid ethyl ester (539-88-8) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: diethyl ether 2: zinc chloride / 140 °C / Behandeln des entstandenen Aethylesters mit alkoh. Kalilauge View Scheme

4-phenylhydrazono-valeric acid-(N'-phenyl-hydrazide) (23228-67-3) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: yellow mercury oxide; alcohol 2: fuming hydrochloric acid; alcohol View Scheme

phenylhydrazine hydrochloride (59-88-1) + levulinic acid (123-76-2) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Fischer indole synthesis;

phenylhydrazine (100-63-0) → 2-methyl-3-indoleacetic acid (1912-43-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sulfuric acid / ethanol / 24 h / Reflux 2: sodium hydroxide; water / 21 h / Reflux View Scheme

2-methyl-3-indoleacetic acid (1912-43-2) + ethanol (64-17-5) → ethyl (2-methylindol-3-yl)acetate (21909-49-9)

Conditions	Yield
With hydrogenchloride	98%
With hydrogenchloride In ethanol	98%
With sulfuric acid for 1h; Heating;

2-methyl-3-indoleacetic acid (1912-43-2) + benzyl chloroformate (501-53-1) → 2-(1-(benzyloxycarbonyl)-2-methyl-1H-indol-3-yl)acetic acid (924635-06-3)

Conditions	Yield
Stage #1: 2-methyl-3-indoleacetic acid With lithium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.5h; Stage #2: benzyl chloroformate In tetrahydrofuran at -78℃; for 1h;	98%

2-methyl-3-indoleacetic acid (1912-43-2) + N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) → N-methoxy-N-methyl-2-(2-methyl-1H-indol- 3-yl)acetamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;	98%
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃;
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃;
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 1h;

methanol (67-56-1) + 2-methyl-3-indoleacetic acid (1912-43-2) → methyl 2-(2-methyl-1H-indol-3-yl)acetate (78564-10-0)

Conditions	Yield
With methanesulfonic acid for 24h;	97%
With hydrogenchloride at 70℃; for 4h;	90.7%
With hydrogenchloride In water at 70℃; for 4h;	90.7%

2-methyl-3-indoleacetic acid (1912-43-2) → methyl 2-(2-methyl-1H-indol-3-yl)acetate (78564-10-0)

Conditions	Yield
With methanesulfonic acid In methanol; ethyl acetate	97%

2-methyl-3-indoleacetic acid (1912-43-2) + (E)-3-((S)-4-pyrrolidin-2-yl-phenyl)-acrylic acid methyl ester hydrochloride (1189152-80-4) → (E)-3-(4-{(S)-1-[2-(2-methyl-1H-indol-3-yl)-acetyl]-pyrrolidin-2-yl}-phenyl)-acrylic acid methyl ester (1189153-37-4)

Conditions	Yield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide for 16h;	93%

2-methyl-3-indoleacetic acid (1912-43-2) + N-(3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)-2-hydroxyacetamide → 2-((3,5-dimethyl-1-phenyl-1H-pyrazol-4-yl)amino)-2-oxoethyl 2-(2-methyl-1H-indol-3-yl)acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 18h;	93%

2-methyl-3-indoleacetic acid (1912-43-2) + benzyl glycolate (30379-58-9) → benzyl 2-(2-(2-methyl-1H-indol-3-yl)acetoxy)acetate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 3h;	91%
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 4h;	88%

2-methyl-3-indoleacetic acid (1912-43-2) + tert-butyldimethylsilyl chloride (18162-48-6) → C17H27NOSi

Conditions	Yield
Stage #1: 2-methyl-3-indoleacetic acid With lithium aluminium tetrahydride In tetrahydrofuran at 0℃; Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In dichloromethane at 20℃;	90%

2-methyl-3-indoleacetic acid (1912-43-2) + 4-methyl-1,2-diaminobenzene (496-72-0) → 5-methyl-2-((2-methyl-1H-indole-3-yl)methyl)-1H-benzimidazole

Conditions	Yield
With polyphosphoric acid In ethylene glycol Reflux;	87%

2-methyl-3-indoleacetic acid (1912-43-2) + 1,2-diamino-benzene (95-54-5) → 2-((2-methyl-1H-indole-3-yl)methyl)-1H-benzimidazole (41278-00-6)

Conditions	Yield
With polyphosphoric acid In ethylene glycol Reflux;	86%

2-methyl-3-indoleacetic acid (1912-43-2) → (3aS,8aR)-3a-hydroxy-8a-methyl-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indol-2-one

Conditions	Yield
With oxygen; Fre protein of Escherichia coli; TsrE protein of Escherichia coli; NADPH; flavin adenine dinucleotide In aq. buffer at 20℃; for 0.5h; pH=7.5; Kinetics; Catalytic behavior; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	84%

2-methyl-3-indoleacetic acid (1912-43-2) → 2-(2-methyl-1H-indol-3-yl)acetaldehyde (54765-13-8)

Conditions	Yield
With diisobutylaluminium hydride at -78℃;	83.9%
Multi-step reaction with 2 steps 1: 5percent H2SO4 / 1 h / Ambient temperature 2: 83.9 percent / 25percent DIBAL / CH2Cl2; 1,2-dimethoxy-ethane; toluene / 1 h / -78 °C View Scheme

2-methyl-3-indoleacetic acid (1912-43-2) + ethyl 3,4-diaminobenzoate (37466-90-3) → C20H19N3O2

Conditions	Yield
With polyphosphoric acid In ethylene glycol Reflux;	83%

2-methyl-3-indoleacetic acid (1912-43-2) + (R)-2-amino-N-methyl-N,3-diphenylpropanamide 2,2,2-trifluoroacetate → (R)-N-methyl-2-(2-(2-methyl-1H-indol-3-yl)-acetamido)-N,3-diphenylpropanamide

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5h;	82%

2-methyl-3-indoleacetic acid (1912-43-2) + sodium 4-methylbenzenesulfinate (824-79-3) → 3-p-toluenesulfonylmethyl-2-methyl-1H-indole

Conditions	Yield
With copper(II) acetate monohydrate In N,N-dimethyl-formamide at 115℃; for 6h; Schlenk technique; Inert atmosphere; regioselective reaction;	81%

2-methyl-3-indoleacetic acid (1912-43-2) + benzylamine (100-46-9) → N-benzyl-2-(2-methyl-1H-indol-3-yl)acetamide (1241355-28-1)

Conditions	Yield
Stage #1: 2-methyl-3-indoleacetic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In dichloromethane at 23℃; for 0.333333h; Stage #2: benzylamine In dichloromethane at 23℃; for 18h;	80%

2-methyl-3-indoleacetic acid (1912-43-2) + (S)-2-amino-N-methyl-N,3-diphenylpropanamide 2,2,2-trifluoroacetate → (S)-N-methyl-2-(2-(2-methyl-1H-indol-3-yl)-acetamido)-N,3-diphenylpropanamide (1352879-65-2)

Conditions	Yield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 1h;	80%
Stage #1: 2-methyl-3-indoleacetic acid With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 20℃; for 0.333333h; Stage #2: (S)-2-amino-N-methyl-N,3-diphenylpropanamide 2,2,2-trifluoroacetate In N,N-dimethyl-formamide at 20℃;

2-methyl-3-indoleacetic acid (1912-43-2) + podofilox (518-28-5) → C33H31NO9

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	79%

ethyl bromide (74-96-4) + 2-methyl-3-indoleacetic acid (1912-43-2) → C13H15NO2

Conditions	Yield
Stage #1: 2-methyl-3-indoleacetic acid With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: ethyl bromide In N,N-dimethyl-formamide	79%

2-methyl-3-indoleacetic acid (1912-43-2) + 19-nor-Δ1,3,5(10)-22α-spirostatriene-3-ol (24036-91-7) → (22R,25R)-3β-(2-methyl-1H-indole-3-acetic carboxylate)-1,3,5(10)-trien-20α-spirostan

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 3h; Inert atmosphere;	74%

2-methyl-3-indoleacetic acid (1912-43-2) + methyl iodide (74-88-4) → methyl 2-(2-methyl-1H-indol-3-yl)acetate (78564-10-0)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide for 10h; Ambient temperature;	73%

2-methyl-3-indoleacetic acid (1912-43-2) + isopropyl bromide (75-26-3) → C14H17NO2

Conditions	Yield
Stage #1: 2-methyl-3-indoleacetic acid With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5h; Stage #2: isopropyl bromide In N,N-dimethyl-formamide	72%

2-methyl-3-indoleacetic acid (1912-43-2) + acetylacetaldehyde dimethyl acetal (5436-21-5) → 2-<1-(3-Oxo-1-butenyl)-2-methyl-3-indolyl>essigsaeure (88114-69-6)

Conditions	Yield
With hydrogenchloride	70%

2-methyl-3-indoleacetic acid (1912-43-2) + C18H22N4O2 → C29H31N5O3

Conditions	Yield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃;	69%

2-methyl-3-indoleacetic acid (1912-43-2) + shikonin (517-89-5) → (R)-1-(5,8-dihydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)-4-methylpent-3-enyl 2-(2-methyl-1H-indol-3-yl)acetate (1397292-76-0)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at -10 - 0℃; for 12h; Inert atmosphere;	68%

2-methyl-3-indoleacetic acid (1912-43-2) + N-(benzylidene)-p-methylbenzenesulfonamide (51608-60-7) → 4-methyl-N-(2-(2-methyl-1H-indol-3-yl)-1-phenylethyl)-benzenesulfonamide

Conditions	Yield
With dipotassium hydrogenphosphate; Ir(dF(CF3)ppy)2(bpy)PF6 In acetonitrile at 25℃; for 18h; Irradiation;	62%

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 50-00-0 formaldehyd 
• 123-76-2 levulinic acid 
• 539-88-8 4-oxopentanoic acid ethyl ester 
• 100-63-0 phenylhydrazine 
• 59-88-1 phenylhydrazine hydrochloride 
• 23228-67-3 4-phenylhydrazono-valeric acid-(N'-phenyl-hydrazide) 
• 62454-47-1 (2-methyl-indol-3-yl)-glyoxylic acid 
• 22980-10-5 (2-methyl-3-indolyl)glyoxyloyl chloride 
• 105-36-2 ethyl bromoacetate 
• 5416-80-8 2-methyl-1H-indole-3-carbaldehyde 
• 33577-16-1 methyl methylsulfinylmethyl sulfide 
• 588-60-3 Levulinic acid phenylhydrazone 
• 3397-38-4 Ethyl 4-Phenylhydrazonopentanoate 

Downstream Products

• 16390-26-4 2-(1-(4-chlorobenzoyl)-2-methyl-1H-indol-3-yl)acetic acid 
• 16401-80-2 (1-benzoyl-2-methyl-indol-3-yl)-acetic acid 
• 1616347-95-5 1'-benzyl-2-methyl-2'-methylenespiro[indole-3,4'-piperidin]-6'-one 
• 1241355-28-1 N-benzyl-2-(2-methyl-1H-indol-3-yl)acetamide 
• 1375277-91-0 PF₇₄-22 
• 1352879-65-2 (S)-N-methyl-2-(2-(2-methyl-1H-indol-3-yl)-acetamido)-N,3-diphenylpropanamide 

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