2,3-Dibromo-N-methylmaleimide

HCID 18155CAS 3005-27-4

Substructure search Find similar structures

Basic information

Standard SMILES: CN1C(=O)C(Br)=C(Br)C1=O
InChIKey: CKITYUQKOJMMOI-UHFFFAOYSA-N
Molecular formula: C5H3Br2NO2
Average molar mass: 268.89 g/mol
Monoisotopic mass: 266.85305254

Names & identifiers

Preferred name: 2,3-Dibromo-N-methylmaleimide
IUPAC: 3,4-dibromo-1-methylpyrrole-2,5-dione
English name: 2,3-Dibromo-N-methylmaleimide
Molecular formula: C5H3Br2NO2
Molecular weight: 268.89

Names & synonyms

2,3-Dibromo-N-methylmaleimideRefChem:441983625-814-93005-27-4N-Methyl-2,3-dibromomaleimide3,4-dibromo-1-methylpyrrole-2,5-dioneN-Methyl-dibromomaleinimideMALEIMIDE, DIBROMO-N-METHYL-3,4-dibromo-1-methyl-2,5-dihydro-1H-pyrrole-2,5-dione3,4-Dibromo-1-methyl-1H-pyrrole-2,5-dione1H-Pyrrole-2,5-dione, 3,4-dibromo-1-methyl-Maleimide, 2,3-dibromo-N-methyl-

Show more names

3,4-dibromo-1-methyl-pyrrole-2,5-dioneSKL607dibromo-n-methyl-maleimidN-METHYLDIBROMOMALEINIMIDE2,3-DibroMo-N-MethylMaleiMide 99%

MFCD00102284NSC 120444BRN 01291493,4-Dibromo-N-methylmaleimideDibromo-N-methylmaleimideV5U5TK6UT53,4-Dibromo-N-methylpyrrole-2,5-dione5-21-10-00050 (Beilstein Handbook Reference)

Database identifiers

CAS: 3005-27-4
PubChem CID: 18155
DTXSID: DTXSID10184108
UNII: V5U5TK6UT5
EC Number: 625-814-9
Nikkaji: J171.280B

Properties

Computed structural properties

XLogP: 1.3
Topological polar surface area: 37.4 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 2
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 222

Physicochemical properties

Melting point: 120 · 120-124 °C (lit.)
Boiling point: 105 °C · 105°C (rough estimate)
Density: 2.2935 · 2.2935 (rough estimate)
refractive index: 1.64 · 1.6400 (estimate)
storage temp.: Inert atmosphere,Room Temperature
pka: -6.23 · -6.23±0.60(Predicted)
Appearance: White to yellow Solid
InChI: 1S/C5H3Br2NO2/c1-8-4(9)2(6)3(7)5(8)10/h1H3
InChIKey: CKITYUQKOJMMOI-UHFFFAOYSA-N
SMILES: CN1C(=O)C(Br)=C(Br)C1=O
CAS DataBase Reference: 3005 · 3005-27-4(CAS DataBase Reference)
FDA UNII: 5 U5TK6UT5 · V5U5TK6UT5
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312-P501
PPE: 95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes: Xn
Risk Statements: 22 · 22
Safety Statements: 36 · 36
WGK Germany: 3 · 3
RTECS: 5125000 · ON5125000
HS Code: 2933998090 · 2933998090
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P351+P338, P330, P337+P317, 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 CategoriesAcute Tox. 4 (100%)

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 3
rtecs: ON5125000
hs_code: 2933998090
risk_code: 22
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: Xn
safety_code: 36
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312-P501

Chemistry & industry

Applications · 1 item

Uses2,3-Dibromo-N-methylmaleimide can be used to synthesize bis-indolylmaleimides via reaction with indolyl magnesium bromide. It can also undergo mono-cross coupling with triorganoindium derivatives which can be further coupled with naphthodithiophene to form an intermediate for [5]thiahelicene synthesis.