Cas no 837392-62-8 (1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole)

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole is a boronic ester derivative of 1-methylindole, commonly employed as an intermediate in Suzuki-Miyaura cross-coupling reactions. The presence of the dioxaborolane group enhances stability and handling under ambient conditions, while the indole scaffold provides versatility in pharmaceutical and agrochemical synthesis. This compound exhibits high reactivity with aryl and heteroaryl halides, facilitating efficient C-C bond formation. Its crystalline solid form ensures consistent purity and ease of quantification in synthetic applications. The electron-rich indole core further enables functionalization at multiple positions, making it a valuable building block for complex molecular architectures. Suitable for use under inert atmospheres to prevent hydrolysis of the boronate moiety.
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole structure
837392-62-8 structure
Product Name:1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
CAS No:837392-62-8
MF:C15H20BNO2
MW:257.135804176331
MDL:MFCD05663865
CID:68901
PubChem ID:16217778
Update Time:2025-06-07

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Chemical and Physical Properties

Names and Identifiers

    • 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
    • 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indazole
    • 1-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indole
    • 1-Methylindole-5-boronic acid, pinacol ester
    • 1-Methylindole-5-borate pinacol ester
    • 1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (ACI)
    • 1-Methylindole-5-boronic acid pinacol ester
    • 4,4,5,5-Tetramethyl-2-(1-methyl-1H-indol-5-yl)-1,3,2-dioxaborolane
    • 4,4,5,5-Tetramethyl-2-(1-methyl-5-indolyl)-1,3,2-dioxaborolane
    • FT-0699039
    • AKOS004114854
    • AB21975
    • SY014930
    • 1-Methyl-5-indolylboronic acid, pinacol ester
    • A849892
    • 837392-62-8
    • N-methylindole-5-boronic acid pinacol ester
    • SCHEMBL484221
    • 1-METHYLINDOLE-5-BORONIC ACID,PINACOL ESTER
    • JQLYKUPEQYNDFF-UHFFFAOYSA-N
    • 1-Methyl-1H-indole-5-boronic acid pinacol ester
    • 1-Methylindole-5-boronic acid pinacol ester, 97%
    • 1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
    • EN300-212562
    • 1-Methyl-5-indoleboronic acid pinacol ester
    • (1-METHYL-1H-INDOL-5-YL)BORONIC ACID PINACOL ESTER
    • J-504961
    • DS-13512
    • BCP32947
    • Z2044774134
    • MFCD05663865
    • AM87226
    • DTXSID80584555
    • CS-W021356
    • 1-Methyl-5-(4 pound not4 pound not5 pound not5-tetramethyl-1 pound not3 pound not2-dioxaborolan-2-yl)-1H-indole
    • DTXCID80535320
    • MDL： MFCD05663865
    • Inchi： 1S/C15H20BNO2/c1-14(2)15(3,4)19-16(18-14)12-6-7-13-11(10-12)8-9-17(13)5/h6-10H,1-5H3
    • InChI Key： JQLYKUPEQYNDFF-UHFFFAOYSA-N
    • SMILES： O1C(C)(C)C(C)(C)OB1C1C=C2C=CN(C2=CC=1)C

Computed Properties

  • Exact Mass: 257.15900
  • Monoisotopic Mass: 257.1587090g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 0
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 19
  • Rotatable Bond Count: 1
  • Complexity: 342
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 23.4?2

Experimental Properties

  • Color/Form: No data avaiable
  • Density: 1.1±0.1 g/cm3
  • Melting Point: 110-114?°C (lit.)
  • Boiling Point: 391.3℃ at 760 mmHg
  • Flash Point: 190.5±20.4 °C
  • PSA: 23.39000
  • LogP: 2.47750
  • Vapor Pressure: 0.0±0.9 mmHg at 25°C

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Security Information

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Customs Data

  • HS CODE：2934999090
  • Customs Data：

    China Customs Code:

    2934999090

    Overview:

    2934999090. Other heterocyclic compounds. VAT:17.0%. Tax refund rate:13.0%. Regulatory conditions:nothing. MFN tariff:6.5%. general tariff:20.0%

    Declaration elements:

    Product Name, component content, use to

    Summary:

    2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
Chemenu
CM134319-1g
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 0.95
1g
 $61 2021-08-05
Ambeed
A149663-250mg
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 97%
250mg
 $18.0 2025-04-16
Ambeed
A149663-1g
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 97%
1g
 $34.0 2025-04-16
Ambeed
A149663-5g
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 97%
5g
 $77.0 2025-04-16
Ambeed
A149663-10g
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 97%
10g
 $143.0 2025-04-16
Ambeed
A149663-25g
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 97%
25g
 $341.0 2025-04-16
SHANG HAI XIAN DING Biotechnology Co., Ltd.
B-BM429-200mg
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8 97%
200mg
 91.0CNY 2021-08-04
TRC
M338053-10mg
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8
10mg
 $ 50.00 2022-06-03
TRC
M338053-50mg
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8
50mg
 $ 65.00 2022-06-03
TRC
M338053-100mg
1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole
 837392-62-8
100mg
 $ 80.00 2022-06-03

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Production Method

Production Method 1

Reaction Conditions
1.1 Reagents: Potassium acetate Catalysts: [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium Solvents: 1,4-Dioxane ;  48 h, 80 °C
Reference
Synthesis of Unnatural Arundines Using a Magnetically Reusable Copper Ferrite Catalyst
Ha, Pha T.; et al, Synlett, 2018, 29(15), 2031-2034

Production Method 2

Reaction Conditions
1.1 Catalysts: Palladium diacetate ,  2-(Dicyclohexylphosphino)biphenyl Solvents: 1,4-Dioxane ;  rt; 30 min, rt
1.2 Reagents: Triethylamine Solvents: 1,4-Dioxane ;  rt; 2 - 8 h, 80 °C
Reference
Convenient synthesis of 1H-indol-1-yl boronates via palladium(0)-catalyzed borylation of bromo-1H-indoles with 'pinacolborane'
Stadlwieser, Josef F.; et al, Helvetica Chimica Acta, 2006, 89(5), 936-946

Production Method 3

Reaction Conditions
1.1 Reagents: 4-(Dimethylamino)pyridine ,  Pivalic anhydride Catalysts: Palladium diacetate ,  1,4-Bis(diphenylphosphino)butane Solvents: 1,4-Dioxane ;  rt; 15 h, 160 °C
Reference
Palladium-Catalyzed Decarbonylative Borylation of Carboxylic Acids: Tuning Reaction Selectivity by Computation
Liu, Chengwei; et al, Angewandte Chemie, 2018, 57(51), 16721-16726

Production Method 4

Reaction Conditions
1.1 Reagents: Triethylamine ,  N,N-Bis(1-methylethyl)boranamine Catalysts: Palladium diacetate ,  Potassium iodide ,  X-Phos Solvents: Ethyl acetate ;  16 h, 50 °C; -5 °C
1.2 Solvents: Methanol ;  1 h, rt
1.3 Solvents: Diethyl ether ;  4 h, rt
Reference
Borylation of Unactivated Aryl Chlorides under Mild Conditions by Using Diisopropylaminoborane as a Borylating Reagent
Guerrand, Helene D. S.; et al, Chemistry - A European Journal, 2014, 20(19), 5573-5579

Production Method 5

Reaction Conditions
1.1 Reagents: Potassium tert-butoxide Catalysts: Iron(III) acetylacetonate Solvents: Toluene ;  16 h, 130 °C; 130 °C → rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
Reference
Iron-catalyzed borylation of aryl chlorides in the presence of potassium t-butoxide
Yoshida, Takumi; et al, ACS Catalysis, 2017, 7(5), 3199-3203

Production Method 6

Reaction Conditions
1.1 Reagents: Sodium hydride Solvents: Dimethyl sulfoxide ,  1,2-Dimethoxyethane ;  rt
1.2 rt; 30 min, rt
1.3 rt
2.1 Catalysts: Palladium diacetate ,  2-(Dicyclohexylphosphino)biphenyl Solvents: 1,4-Dioxane ;  rt; 30 min, rt
2.2 Reagents: Triethylamine Solvents: 1,4-Dioxane ;  rt; 2 - 8 h, 80 °C
Reference
Convenient synthesis of 1H-indol-1-yl boronates via palladium(0)-catalyzed borylation of bromo-1H-indoles with 'pinacolborane'
Stadlwieser, Josef F.; et al, Helvetica Chimica Acta, 2006, 89(5), 936-946

Production Method 7

Reaction Conditions
1.1 Reagents: Potassium methoxide Catalysts: (T-4)-Dichlorobis[1,3-dihydro-1,3-bis(2,4,6-trimethylphenyl)-2H-imidazol-2-ylide… Solvents: tert-Butyl methyl ether ;  8 h, 50 °C
Reference
Efficient Synthesis of Aryl Boronates via Cobalt-Catalyzed Borylation of Aryl Chlorides and Bromides
Verma, Piyush Kumar; et al, ACS Catalysis, 2018, 8(5), 4049-4054

Production Method 8

Reaction Conditions
1.1 Solvents: Tetrahydrofuran ;  12 h, rt
Reference
Iron-catalysed enantioselective Suzuki-Miyaura coupling of racemic alkyl bromides
Iwamoto, Takahiro; et al, Chemical Communications (Cambridge, 2019, 55(8), 1128-1131

Production Method 9

Reaction Conditions
1.1 Solvents: Diethyl ether ;  overnight, rt
Reference
Palladium-catalyzed allylic cross-coupling reactions of primary and secondary homoallylic electrophiles
Stokes, Benjamin J.; et al, Journal of the American Chemical Society, 2012, 134(28), 11408-11411

Production Method 10

Reaction Conditions
1.1 Reagents: Oxygen Catalysts: Cobalt salophen complex ,  Ruthenium(2+), tris(1,10-phenanthroline-5,6-dione-κN1,κN10)-, (OC-6-11)-, hexafl… Solvents: Methanol ;  6 h, 65 °C
Reference
Replacement of Stoichiometric DDQ with a Low Potential o-Quinone Catalyst Enabling Aerobic Dehydrogenation of Tertiary Indolines in Pharmaceutical Intermediates
Li, Bao; et al, Organic Letters, 2019, 21(4), 1176-1181

Production Method 11

Reaction Conditions
1.1 Reagents: Potassium methoxide Solvents: 1,2-Dimethoxyethane ;  10 min, 30 °C
1.2 1 h, 30 °C; 30 °C → 0 °C
1.3 Reagents: Tetrabutylammonium fluoride ;  3 h, 0 °C
Reference
Formal Nucleophilic Boryl Substitution of Organic Halides with Silylborane/Alkoxy Base System
Yamamoto, Eiji; et al, Topics in Catalysis, 2014, 57(10-13), 940-945

Production Method 12

Reaction Conditions
1.1 Reagents: Potassium methoxide Solvents: 1,2-Dimethoxyethane ;  10 min, 30 °C
1.2 30 °C; 1 h, 30 °C
Reference
Anomalous Reactivity of Silylborane: Transition-Metal-Free Boryl Substitution of Aryl, Alkenyl, and Alkyl Halides with Silylborane/Alkoxy Base Systems
Yamamoto, Eiji; et al, Journal of the American Chemical Society, 2012, 134(49), 19997-20000

Production Method 13

Reaction Conditions
1.1 Reagents: Zinc ,  Lithium chloride Catalysts: Cobalt dibromide ;  15 min, 400 °C; cooled
1.2 Reagents: Chlorotrimethylsilane Catalysts: Trichlorotris(tetrahydrofuran)chromium ,  1,1′-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis[1,1-diphenylphosphine] Solvents: Tetrahydrofuran ;  5 min, cooled
1.3 48 h, 60 °C; 60 °C → rt
1.4 Solvents: Ethyl acetate ,  Water ;  rt
Reference
The drastic effect of cobalt and chromium catalysts in the borylation of arylzinc reagents
Komeyama, Kimihiro; et al, Chemical Communications (Cambridge, 2016, 52(43), 7009-7012

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Raw materials

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Preparation Products

1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole Related Literature

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837392-62-8 (1-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole) Related Products

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