N-Boc-5-bromoindole

HCID 2728482

Notes Reactions

Substructure search Find similar structures

Basic information

CAS: 182344-70-3
Standard SMILES: CC(C)(C)OC(=O)n1ccc2cc(Br)ccc21
InChIKey: PBWDRTGTQIXVBR-UHFFFAOYSA-N
Molecular formula: C13H14BrNO2
Average molar mass: 296.16 g/mol
Monoisotopic mass: 295.02079079

Names & identifiers

Preferred name: N-Boc-5-bromoindole
IUPAC: tert-butyl 5-bromoindole-1-carboxylate
English name: TERT-BUTYL 5-BROMOINDOLE-1-CARBOXYLATE
Molecular formula: C13H14BrNO2
Molecular weight: 296.16

Names & synonyms

182344-70-3N-Boc-5-bromoindoleDTXSID90369512RefChem:363489DTXCID50320548627-270-8tert-Butyl 5-Bromo-1H-indole-1-carboxylatetert-Butyl 5-bromoindole-1-carboxylate5-BROMO-1-TERT-BUTOXYCARBONYLINDOLE1-BOC-5-bromoindole1H-INDOLE-1-CARBOXYLIC ACID, 5-BROMO-, 1,1-DIMETHYLETHYL ESTERMFCD02090067

Show more names

N-Boc-5-bromoindole 13C613C6]-N-Boc-5-Bromoindole5-Bromo-1-(t-Butoxycarbonyl)-1H-indole

1-(t-butoxycarbonyl)-5-bromoindoleAKOS015837005TS-01076tert-butyl 5-bromoindolecarboxylatetert-Butyl5-bromo-1H-indole-1-carboxylateMaybridge3_005555FT-06540071-Boc-5-bromo-1H-indole

Database identifiers

CAS: 182344-70-3
PubChem CID: 2728482
DTXSID: DTXSID90369512
EC Number: 627-270-8
Nikkaji: J1.406.753A

Properties

Computed structural properties

XLogP: 4
Topological polar surface area: 31.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 17
Formal charge: 0
Complexity: 300

Physicochemical properties

Melting point: 56 · 56-57 °C(lit.)
Boiling point: 367.9 · 367.9±34.0 °C(Predicted)
Density: 1.37 · 1.37±0.1 g/cm3(Predicted)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
form: Solid
color: White to off-white
InChI: InChI=1S/C13H14BrNO2/c1-13(2,3)17-12(16)15-7-6-9-8-10(14)4-5-11(9)15/h4-8H,1-3H3
InChIKey: PBWDRTGTQIXVBR-UHFFFAOYSA-N
SMILES: N1(C(OC(C)(C)C)=O)C2=C(C=C(Br)C=C2)C=C1
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 315 · H315-H319-H335
Precautionary statements: 261 · P261-P264-P271-P280-P302+P352-P305+P351+P338
target organs: Respiratory system
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xi
Risk Statements: 36 · 36/37/38
Safety Statements: 26 · 26-36
WGK Germany: 3 · 3
HS Code: 2933998090 · 2933998090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 2 Skin · Eye Irrit. 2Skin Irrit. 2STOT SE 3

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 40 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
hs_code: 2933998090
risk_code: 36/37/38
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xi
safety_code: 26-36
Storage Class: 11 - Combustible Solids
target organs: Respiratory system
Hazard statements: H315-H319-H335
Hazard Classifications: Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements: P261-P264-P271-P280-P302+P352-P305+P351+P338

Chemistry & industry

Applications · 2 items

UsesN-Boc-5-bromoindole is formed as an intermediate for the synthesis of di-Boc-protected 5-aminoindole via a Buchwald-Hartwig amination with tBu-carbamate followed by regioselective bromination[1].

General DescriptionN-Boc-5-bromoindole can undergo Sonogashira coupling reaction with N,N-diisopropylprop-2-ynylamine to afford the corresponding propargylic diisopropylamine. N-Boc-5-bromoindole is formed as an intermediate during the synthesis of 2-(5-substituted-1H-indol-3-yl)-N-hydroxyacetamide derivatives.