Dimethylmethylenammoniumchlorid

Dimethylmethylenammonium chloride

HCID 11051579

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Grundinformationen

CAS: 30354-18-8
Standard-SMILES: C=[N+](C)C.[Cl-]
InChIKey: ZJTROANVDZIEGB-UHFFFAOYSA-M
Summenformel: C3H8ClN
Durchschnittliche Molmasse: 93,55 g/mol

Namen und Bezeichner

Bevorzugter Name: Dimethylmethylenammonium chloride
IUPAC: dimethyl(methylidene)azanium chloride
Lokaler Name: Dimethylmethylenammoniumchlorid
Englischer Name: Eschenmoser's salt
Summenformel: C3H8ClN
Molmasse: 93.56

Namen und Synonyme

Dimethylmethylenammonium chlorideEINECS 250-142-4RefChem:588574250-142-430354-18-8N,N-Dimethylmethyleneiminium chloriden-methyl-n-methylenemethanaminium chlorideMFCD00011809Methanaminium, N-methyl-N-methylene-, chloride (9CI)dimethyl(methylidene)azanium;chlorideN,N-Dimethylmethyleneiminium Chloride (Technical Grade)N,N-dimethyl(methylene)ammonium chloride

Weitere Namen anzeigen

ESCHENMOSER SALTEschenmoser's saltMethylenedimethylammonium chlorideDIMETHYL(METHYLIDENE)AZANIUM BROMIDEN,N-dimethylmethyleneammonium bromidedimethyl(methylidene)azanium:chloride

N,N-dimethyl-methylene ammonium chlorideDIMETHYL(METHYLENE)AMMONIUM CHLORIDEDimethylformiminium chloridedimethyl(methylidene)azanium chlorideSCHEMBL443366DTXSID60952697N,N-Dimethylmethaniminium chlorideDimethyl(methylene)iminium chloride

Datenbank-Bezeichner

CAS: 30354-18-8
PubChem CID: 11051579
DTXSID: DTXSID60952697
EC Number: 250-142-4

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 3 Å²
H-Brücken-Donoren: 0
H-Brücken-Akzeptoren: 1
Frei drehbare Bindungen: 0
Schwere Atome: 5
Formalladung: 0
Komplexität: 26,3

Physikochemische Eigenschaften

Schmelzpunkt: 146 · 146-148 °C(lit.)
Flammpunkt: 180 °F · 180 °F
storage temp.: 30 °C · Store below +30°C.
Löslichkeit: Chloroform (Very Slightly, Heated), DMSO (Sparingly, Heated, Sonicated)
Aggregatzustand: Solid
Farbe: White to Off-White
BRN: 505955 · 505955
Stabilität: Hygroscopic, Unstable in Protic Solvent
InChI: 1S/C3H8N.ClH/c1-4(2)3;/h1H2,2-3H3;1H/q+1;/p-1
InChIKey: ZJTROANVDZIEGB-UHFFFAOYSA-M
SMILES: [Cl-].C[N+](C)=C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H228 (100%): Flammable solid [Danger Flammable solids]

P210, P240, P241, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory InformationMethanaminium, N-methyl-N-methylene-, chloride: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesFlam. Sol. 2 (100%)

Sicherheitsdaten

F: 3-10-21
wgk: 3
ridadr: UN 1325 4.1/PG 3
risk_code: 36/37/38
hazard_code: Xi
safety_code: 26-36
Speicherklasse: 4.1B - Flammable solid hazardous materials
Hazard Classifications: Eye Irrit. 2Flam. Sol. 2Skin Irrit. 2STOT SE 3

Chemie und Industrie

Anwendungen · 1 Eintrag

VerwendenN,N-Dimethylmethyleneiminium chloride (Bhme′s salt) is a dimethylaminomethylating agent that can be used as one of the key reagents in the following applications:Electrophilic aminomethylation of aldehydes and ketones to synthesize corresponding Mannich products, also known as Mannich reaction.Preparation of dihydronaphthyridinones as HIV-1 integrase inhibitors.Preparation of cyanotetrahydrooxo-β-carbolines via cyclocondensation of cyanomethyl indole-2-carboxylate with ammonia.Asymmetric synthesis of phalarine via stereospecific Pictet-Spengler cyclocondensation and traceless chirality transfer from L-tryptophan.Synthesis of functionalized diarylpyrrolizines as inhibitors of microsomal prostaglandin E2 synthase-1 (mPGES-1) and 5-lipoxygenase (5-LOX).Synthesis of (±)-phalarine with the rearrangement of an azaspiroindolenine and Gassman oxindole preparation as key steps.