Cas no 877-03-2 (5-Bromo-1H-indole-3-carbaldehyde)

5-Bromo-1H-indole-3-carbaldehyde structure

877-03-2 structure

Product Name:5-Bromo-1H-indole-3-carbaldehyde

CAS No:877-03-2

MF:C₉H₆BrNO

MW:224.054041385651

MDL:MFCD00152016

CID:40167

PubChem ID:24874042

Update Time:2024-10-26

5-Bromo-1H-indole-3-carbaldehyde Chemical and Physical Properties

Names and Identifiers

- 5-Bromoindole-3-carboxaldehyde
- 5-Bromo-1H-indole-3-carbaldehyde
- 5-Bromo-3-formylindole
- 5-Bromoindole-3-carboxyaldehyde
- 5-Bromoindole-3-carbaldehyde
- 1H-Indole-3-carboxaldehyde, 5-bromo-
- 5-bromoindole-3-aldehyde
- 5-bromo-3-formyl-1h-indole
- 5-BROMO-1H-INDOLE-3-CARBOXALDEHYDE
- NSC66831
- PubChem9122
- KSC494E7J
- 5-bromo-indole-3-carboxaldehyde
- 5-Bromo-1H-indole-3-carbaldehye
- 5-Bromo-1H-indole-3-carboxaldehyde (ACI)
- Indole-3-carboxaldehyde, 5-bromo- (6CI, 7CI, 8CI)
- NSC 66831
- AB00275453-04
- AKOS000289141
- AS-11393
- SY014468
- ALBB-035498
- MFCD00152016
- AB04031
- NSC-66831
- B-8600
- DB-001973
- Z57627647
- 5-Bromo-1H-indole-3-carbaldehyde #
- NS00039212
- 877-03-2
- 5-Bromoindole-3-carboxaldehyde, 98%
- STK980631
- SCHEMBL671217
- EN300-18251
- NCGC00328903-01
- 8JS5DEX3ZE
- AC-23641
- DTXSID80236562
- CS-W002437
- B4840
- EINECS 212-884-7
- MDL： MFCD00152016
- Inchi： 1S/C9H6BrNO/c10-7-1-2-9-8(3-7)6(5-12)4-11-9/h1-5,11H
- InChI Key： PEENKJZANBYXNB-UHFFFAOYSA-N
- SMILES： O=CC1C2C(=CC=C(C=2)Br)NC=1
- BRN： 124725

Computed Properties

Exact Mass: 222.96300
Monoisotopic Mass: 222.963276
Isotope Atom Count: 0
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 1
Heavy Atom Count: 12
Rotatable Bond Count: 1
Complexity: 185
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
XLogP3: 2.4
Topological Polar Surface Area: 32.9
Surface Charge: 0
Tautomer Count: 3

Experimental Properties

Color/Form: White to Yellow Solid
Density: 1.727
Melting Point: 204.0 to 208.0 deg-C
Boiling Point: 395.6 °C at 760 mmHg
Flash Point: 193℃
Refractive Index: 1.752
PSA: 32.86000
LogP: 2.74290
Solubility: Not determined

5-Bromo-1H-indole-3-carbaldehyde Security Information

Symbol:
Prompt：warning
Signal Word：Warning
Hazard Statement： H315,H319,H335
Warning Statement： P261,P305+P351+P338
Hazardous Material transportation number：NONH for all modes of transport
WGK Germany：3
Hazard Category Code： 36/37/38
Safety Instruction： S26-S36-S37/39
Hazardous Material Identification：
HazardClass：IRRITANT
Storage Condition：Store at room temperature
Risk Phrases：R36/37/38

5-Bromo-1H-indole-3-carbaldehyde Customs Data

HS CODE：2933990090
Customs Data：

China Customs Code:
2933990090

Overview:

2933990090. Other heterocyclic compounds containing only nitrogen heteroatoms. 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, Please indicate the appearance of Urotropine, 6- caprolactam please indicate the appearance, Signing date

Summary:

2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

5-Bromo-1H-indole-3-carbaldehyde Pricemore >>

Related Categories	No.	Product Name	Cas No.	Purity	Specification	Price	update time
SHANG HAI XIAN DING Biotechnology Co., Ltd.	BD103-5g	5-Bromo-1H-indole-3-carbaldehyde	877-03-2	98%	5g	￥142.0	2022-06-10
SHANG HAI XIAN DING Biotechnology Co., Ltd.	BD103-25g	5-Bromo-1H-indole-3-carbaldehyde	877-03-2	98%	25g	￥467.0	2022-06-10
SHANG HAI XIAN DING Biotechnology Co., Ltd.	BD103-1g	5-Bromo-1H-indole-3-carbaldehyde	877-03-2	98%	1g	￥49.0	2022-06-10
SHANG HAI XIAN DING Biotechnology Co., Ltd.	B4840-1g	5-Bromo-1H-indole-3-carbaldehyde	877-03-2	98.0%(GC)	1g	￥165.0	2022-06-10
SHANG HAI XIAN DING Biotechnology Co., Ltd.	B4840-5g	5-Bromo-1H-indole-3-carbaldehyde	877-03-2	98.0%(GC)	5g	￥725.0	2022-06-10
SHANG HAI MAI KE LIN SHENG HUA Technology Co., Ltd.	B803876-25g	5-Bromoindole-3-carboxaldehyde	877-03-2	97%	25g	526.00	2021-05-17
XI GE MA AO DE LI QI （ SHANG HAI ） MAO YI Co., Ltd.	518743-5G	5-Bromo-1H-indole-3-carbaldehyde	877-03-2		5g	￥745.3	2023-12-05
Matrix Scientific	009757-5g	5-Bromo-3-formylindole, 97%	877-03-2	97%	5g	$14.00	2023-09-09
Matrix Scientific	009757-25g	5-Bromo-3-formylindole, 97%	877-03-2	97%	25g	$49.00	2023-09-09
SHANG HAI YI EN HUA XUE JI SHU Co., Ltd.	R001600-1g	5-Bromo-1H-indole-3-carbaldehyde	877-03-2	97%	1g	￥26	2024-05-21

5-Bromo-1H-indole-3-carbaldehyde Production Method

Production Method 1

92557-51-2

877-03-2

Reaction Conditions

1.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Catalysts: Trifluoromethanesulfonic acid Solvents: 1,4-Dioxane ; 23 min, rt

Reference

IBX-TfOH mediated oxidation of alcohols to aldehydes and ketones under mild reaction conditions

Kumar, Kamlesh; et al, Tetrahedron Letters, 2020, 61(15),

Production Method 2

92557-51-2

877-03-2

Reaction Conditions

1.1 Reagents: 1-Hydroxy-1,2-benziodoxol-3(1H)-one 1-oxide Catalysts: (±)-Camphorsulfonic acid Solvents: Dichloromethane , 1,4-Dioxane ; 10 min, rt
1.2 5 min, rt; 10 - 30 min, rt

Reference

(±)-Camphor sulfonic acid assisted IBX based oxidation of 1° and 2° alcohols

Kumar, Kamlesh; et al, Tetrahedron Letters, 2021, 81,

Production Method 3

830-93-3

877-03-2

Reaction Conditions

1.1 Reagents: Oxygen , Pyridinium chlorochromate Solvents: Dimethylformamide ; 0.5 h, 100 °C; cooled
1.2 Reagents: Hydrochloric acid Solvents: Water

Reference

Cu-mediated oxidative dimerization of skatole to tryptanthrin, an indolo[2,1-b]quinazolone alkaloid

Itoh, Tomoki; et al, Heterocycles, 2015, 91(7), 1423-1428

Production Method 4

10075-50-0

1535-67-7

877-03-2

Reaction Conditions

1.1 Catalysts: Bismuth triflate Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 5 min, rt
1.2 Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 12 h, rt
1.3 Reagents: 2-Iodoxybenzoic acid Solvents: Dimethyl sulfoxide , Water ; 1 h, rt
1.4 Reagents: Sodium sulfite Solvents: Water ; rt
1.5 Reagents: Sodium bicarbonate Solvents: Water ; basified, rt

Reference

Bi(OTf)3 Enabled C-F Bond Cleavage in HFIP: Electrophilic Aromatic Formylation with Difluoro(phenylsulfanyl)methane

Betterley, Nolan M.; et al, Asian Journal of Organic Chemistry, 2018, 7(8), 1642-1647

Production Method 5

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Potassium iodide , Water Catalysts: Red 21 Solvents: Acetonitrile ; 48 h, rt

Reference

Visible-Light-Promoted Indole C-3 Formylation Using Eosin Y as a Photoredox Catalyst

Zhao, Yin; et al, Synlett, 2022, 33(7), 659-663

Production Method 6

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Pivalic acid , tert-Butyl peroxybenzoate Catalysts: Tetrabutylammonium iodide Solvents: Dimethyl sulfoxide ; 8 h, 80 °C
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

nBu4NI-catalyzed C3-formylation of indoles with N-methylaniline

Li, Lan-Tao; et al, Chemical Communications (Cambridge, 2012, 48(42), 5187-5189

Production Method 7

487-89-8

877-03-2

Reaction Conditions

1.1 Reagents: N-Bromosuccinimide Catalysts: Scandium triflate Solvents: 1,1,1,3,3,3-Hexafluoro-2-propanol ; 2 - 10 h, 110 °C

Reference

Sunlight Induced and Alternative Sc(OTf)3 Catalyzed Remote C-H Halogenation of Indoles

Liu, Shanshan ; et al, Chemistry - A European Journal, 2023, 29(36),

Production Method 8

487-89-8

877-03-2

Reaction Conditions

1.1 Reagents: Sodium bisulfite Solvents: Ethanol , Water ; 20 h, rt
2.1 rt → 70 °C; 2 h, 70 °C; 0.5 h, 70 °C → 90 °C; cooled
3.1 Reagents: Bromine Solvents: Water ; rt → 5 °C; < 5 °C; 1 h, 0 °C; 1 h, 0 °C → rt
3.2 Reagents: Sodium bisulfite Solvents: Water
3.3 Reagents: Sodium hydroxide ; overnight, reflux; reflux → 10 °C
4.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ; 5 min, 0 °C
4.2 Solvents: Dimethylformamide ; 0 °C → rt; 3 h, rt
4.3 Reagents: Potassium hydroxide Solvents: Water ; overnight, reflux

Reference

Integrated structure-based activity prediction model of benzothiadiazines on various genotypes of HCV NS5b polymerase (1a, 1b and 4) and its application in the discovery of new derivatives

Ismail, Mohamed A. H.; et al, Bioorganic & Medicinal Chemistry, 2012, 20(7), 2455-2478

Production Method 9

10075-50-0

93-61-8

877-03-2

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of fully conjugated carbocycles and heterocycles

Jones, Gurnos; et al, Organic Reactions (Hoboken, 1997, 49,

Production Method 10

22190-33-6

877-03-2

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ; rt; 2 h, rt
1.2 Reagents: Sodium hydroxide Solvents: Water ; basified, cooled

Reference

Synthesis, biological evaluation, and molecular docking studies of novel 1-benzene acyl-2-(1-methylindol-3-yl)-benzimidazole derivatives as potential tubulin polymerization inhibitors

Wang, Yan-Ting; et al, European Journal of Medicinal Chemistry, 2015, 99, 125-137

Production Method 11

26807-69-2

877-03-2

Reaction Conditions

1.1 Reagents: Bromine Solvents: Water ; rt → 5 °C; < 5 °C; 1 h, 0 °C; 1 h, 0 °C → rt
1.2 Reagents: Sodium bisulfite Solvents: Water
1.3 Reagents: Sodium hydroxide ; overnight, reflux; reflux → 10 °C
2.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ; 5 min, 0 °C
2.2 Solvents: Dimethylformamide ; 0 °C → rt; 3 h, rt
2.3 Reagents: Potassium hydroxide Solvents: Water ; overnight, reflux

Reference

Integrated structure-based activity prediction model of benzothiadiazines on various genotypes of HCV NS5b polymerase (1a, 1b and 4) and its application in the discovery of new derivatives

Ismail, Mohamed A. H.; et al, Bioorganic & Medicinal Chemistry, 2012, 20(7), 2455-2478

Production Method 12

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride Solvents: Dimethylformamide ; 5 min, 0 °C
1.2 Solvents: Dimethylformamide ; 0 °C → rt; 3 h, rt
1.3 Reagents: Potassium hydroxide Solvents: Water ; overnight, reflux; reflux → rt

Reference

Enantioselective Bronsted Acid-Catalyzed N-Acyliminium Cyclization Cascades

Muratore, Michael E.; et al, Journal of the American Chemical Society, 2009, 131(31), 10796-10797

Production Method 13

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Phosphorus oxychloride

Reference

N-Pyridinylindole-3-(alkyl)carboxamides and derivatives as potential systemic and topical inflammation inhibitors

Duflos, M.; et al, European Journal of Medicinal Chemistry, 2001, 36(6), 545-553

Production Method 14

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Dimethylformamide , Phosphorus oxychloride Solvents: Dimethylformamide

Reference

Synthesis of N(10)-acetyleudistomin L

Still, Ian W. J.; et al, Tetrahedron Letters, 1989, 30(9), 1041-4

Production Method 15

10075-50-0

877-03-2

Reaction Conditions

Reference

Chemoselective Cu-catalyzed synthesis of diverse N-arylindole carboxamides, β-oxo amides and N-arylindole-3-carbonitriles using diaryliodonium salts

Kumar Mehra, Manish; et al, Organic & Biomolecular Chemistry, 2021, 19(5), 1109-1114

Production Method 16

10075-50-0

877-03-2

Reaction Conditions

Reference

Fluorescent Porous Silica Microspheres for Highly and Selectively Detecting Hg2+ and Pb2+ Ions and Imaging in Living Cells

Sun, Wei; et al, ACS Omega, 2019, 4(19), 18381-18391

Production Method 17

10075-50-0

298-12-4

877-03-2

Reaction Conditions

1.1 Reagents: Sodium perchlorate Catalysts: Aniline , Platinum Solvents: Dimethyl sulfoxide , Water ; 7 h, rt

Reference

Synthesis of 3-Formylindoles via Electrochemical Decarboxylation of Glyoxylic Acid with an Amine as a Dual Function Organocatalyst

Lin, Dian-Zhao; et al, Organic Letters, 2019, 21(15), 5862-5866

Production Method 18

10075-50-0

298-12-4

877-03-2

Reaction Conditions

1.1 Reagents: Potassium persulfate Solvents: Acetonitrile ; 8 h, 80 °C; 80 °C → rt
1.2 Reagents: Sodium carbonate Solvents: Water ; rt

Reference

Site-Selective Decarboxylative Direct Formylation of Nitrogen Heterocycles (Azaindoles, Indoles, Pyrroles) and Anilines Utilizing Glyoxylic Acid

Laha, Joydev K. ; et al, Advanced Synthesis & Catalysis, 2023, 365(8), 1238-1246

Production Method 19

10075-50-0

298-12-4

877-03-2

Reaction Conditions

1.1 Reagents: Sodium acetate , Oxygen Solvents: Acetonitrile ; 24 h, rt

Reference

Synthesis of C-1 Deuterated 3-Formylindoles by Organophotoredox Catalyzed Direct Formylation of Indoles with Deuterated Glyoxylic Acid

Dong, Yue; et al, Organic Letters, 2022, 24(28), 5034-5039

Production Method 20

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Iodine Solvents: Dimethylformamide ; 12 h, 100 °C

Reference

Iodine-catalyzed C3-formylation of indoles via C-N bond cleavage of tertiary amines under aerobic conditions

Lu, Lin; et al, Tetrahedron, 2015, 71(22), 3637-3641

Production Method 21

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Sodium carbonate , Oxygen Catalysts: Iodine Solvents: 1,4-Dioxane , Water ; rt; 36 h, 100 °C; 100 °C → rt

Reference

I2-mediated C3-formylation of indoles by tertiary amine and H2O

Zhang, Bo; et al, Tetrahedron Letters, 2014, 55(41), 5618-5621

Production Method 22

81387-89-5

877-03-2

Reaction Conditions

1.1 Reagents: Chloro(1-methylethyl)magnesium Solvents: Tetrahydrofuran ; 5 min, 0 °C; 5 min, 0 °C
1.2 Reagents: Butyllithium Solvents: Hexane ; 5 min, < -20 °C; 0.5 h, < -20 °C
1.3 Solvents: Tetrahydrofuran ; 0.5 h, -20 °C
1.4 Reagents: Water ; 10 min, < -20 °C

Reference

Halogen-metal exchange on bromoheterocyclics with substituents containing an acidic proton via formation of a magnesium intermediate

Tian, Qingqiang; et al, Molecules, 2017, 22(11), 1952/1-1952/12

Production Method 23

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: tert-Butyl hydroperoxide , Pivalic acid Catalysts: Ruthenium trichloride Solvents: N-Methylacetamide ; 0 °C; 24 h, 25 °C

Reference

Mild and Selective Ru-Catalyzed Formylation and Fe-Catalyzed Acylation of Free (N-H) Indoles Using Anilines as the Carbonyl Source

Wu, Wenliang; et al, Journal of the American Chemical Society, 2011, 133(31), 11924-11927

Production Method 24

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Ammonia , Oxygen Catalysts: Iron chloride (FeCl3) Solvents: Dimethylformamide , Water ; 7.5 h, 130 °C

Reference

Iron-Catalyzed C3-Formylation of Indoles with Formaldehyde and Aqueous Ammonia under Air

Wang, Qing-Dong; et al, Synlett, 2017, 28(19), 2670-2674

Production Method 25

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Iodine Solvents: Dimethylformamide ; 4 h, 120 °C

Reference

Iodine-catalyzed C3-formylation of indoles using hexamethylenetetramine and air

Wang, Qing-Dong; et al, Tetrahedron Letters, 2017, 58(30), 2877-2880

Production Method 26

10075-50-0

877-03-2

Reaction Conditions

1.1 Reagents: Acetic acid , Methylcyclohexylamine Catalysts: Bismuth vanadate (BiVO4) , Carbon nitride (C3N4) Solvents: Methanol ; 58 h, rt

Reference

A stable and recyclable Z-scheme g-C3N4/rGO/BiVO4 heterojunction photocatalyst for site-selective C-3 formylation of indoles with methanol as a formyl source under visible light

Lei, Zhenkai; et al, Green Chemistry, 2023, 25(1), 348-356

Production Method 27

1240045-42-4

877-03-2

Reaction Conditions

1.1 Reagents: Sodium carbonate , Boronic acid Catalysts: Tetrakis(triphenylphosphine)palladium Solvents: 1,4-Dioxane ; reflux
1.2 Reagents: Phosphorus oxychloride ; 0 - 23 °C

Reference

Novel benzofuran-3-one indole inhibitors of PI3 kinase-α and the mammalian target of rapamycin: hit to lead studies

Bursavich, Matthew G.; et al, Bioorganic & Medicinal Chemistry Letters, 2010, 20(8), 2586-2590

Production Method 28

224156-28-9

877-03-2

Reaction Conditions

1.1 -
2.1 Reagents: Phosphorus oxychloride

Reference

The Vilsmeier reaction of fully conjugated carbocycles and heterocycles

Jones, Gurnos; et al, Organic Reactions (Hoboken, 1997, 49,

5-Bromo-1H-indole-3-carbaldehyde Raw materials

5-Bromo-1H-indole-3-carbaldehyde Preparation Products

5-Bromo-1H-indole-3-carbaldehyde (877-03-2)

5-Bromo-1H-indole-3-carbaldehyde Related Literature

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Cas no 877-03-2 (5-Bromo-1H-indole-3-carbaldehyde)

5-Bromo-1H-indole-3-carbaldehyde Chemical and Physical Properties

Names and Identifiers

Computed Properties

Experimental Properties

5-Bromo-1H-indole-3-carbaldehyde Security Information

5-Bromo-1H-indole-3-carbaldehyde Customs Data

China Customs Code:

Overview:

Declaration elements:

Summary:

5-Bromo-1H-indole-3-carbaldehyde Pricemore >>

5-Bromo-1H-indole-3-carbaldehyde Production Method

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5-Bromo-1H-indole-3-carbaldehyde Raw materials

5-Bromo-1H-indole-3-carbaldehyde Preparation Products

5-Bromo-1H-indole-3-carbaldehyde Related Literature

Related Categories

877-03-2 (5-Bromo-1H-indole-3-carbaldehyde) Related Products