1-Methoxypropa-1,2-diene

HCID 139403

Notes Reactions

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Basic information

CAS: 13169-00-1
Standard SMILES: C=C=COC
InChIKey: RRWJXAJEGRDMQH-UHFFFAOYSA-N
Molecular formula: C4H6O
Average molar mass: 70.09 g/mol

Names & identifiers

Preferred name: 1-Methoxypropa-1,2-diene
IUPAC: 1-methoxypropa-1,2-diene
English name: Methoxyallene; 95%discontinued 05/24/01
Molecular formula: C4H6O
Molecular weight: 70.09

Names & synonyms

1-methoxypropa-1,2-dieneRefChem:433596626-628-0Methoxyallene13169-00-11-Methoxyallene1,2-Propadiene, 1-methoxy-1,2-Propadiene,1-methoxy- (9CI)METHOXYALLENE; 95per centDISCONTINUED 05/24/011-METHOXY-1,2-PROPADIENE1,2-Propadiene, 3-methoxy-methoxyallen

Show more names

3-MethoxyalleneMethoxypropadiene1-MethoxypropadieneAllenyl methyl etherPropadienylmethyl ether

methoxyallyl1-methoxy-1,2-propanedieneNSC363923NSC 363923CH2=C=CHOCH3Methoxyallene, technical gradeSCHEMBL1992420SCHEMBL28320944

Database identifiers

CAS: 13169-00-1
PubChem CID: 139403
EC Number: 626-628-0
Nikkaji: J340.838H

Properties

Computed structural properties

XLogP: 0.4
Topological polar surface area: 9.2 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 1
Rotatable bonds: 1
Heavy atoms: 5
Formal charge: 0
Complexity: 50.7

Experimental & physicochemical properties

SpringerMaterials PropertiesCoriolis coupling

Physicochemical properties

Boiling point: 48.2 ℃ · 48.2℃ (760 torr)
Density: 0.832 g/mL · 0.832 g/mL at 25 °C
refractive index: 20 · n20/D 1.429
Flash point: -29 °C · -29 °C
storage temp.: 2 · 2-8°C
solubility: 2 Cl2, · sol THF, ether, pentane, hexane, CH2Cl2, CHCl3, DMSO
form: liquid
InChI: 1S/C4H6O/c1-3-4-5-2/h4H,1H2,2H3
InChIKey: RRWJXAJEGRDMQH-UHFFFAOYSA-N
SMILES: COC=C=C
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02
Signal word: Danger
Hazard statements: 225 · H225
Precautionary statements: 210 · P210
PPE: Eyeshields, Faceshields, Gloves
Hazard Codes: F
Risk Statements: 11 · 11
RIDADR: 1993 · UN 1993 3/PG 2
WGK Germany: 3 · 3
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 2 · Flam. Liq. 2

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P280, P303+P361+P353, P370+P378, P403+P235, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 2 notifications to the ECHA C&L Inventory.

Hazard information

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

Safety data

PPE: Eyeshields, Faceshields, Gloves
wgk: 3
ridadr: UN 1993 3/PG 2
risk_code: 11
Signal word: Danger
Symbol(GHS): GHS02
hazard_code: F
Storage Class: 3 - Flammable liquids
Hazard statements: H225
Hazard Classifications: Flam. Liq. 2
Precautionary statements: P210

Chemistry & industry

Applications · 2 items

UsesReactant involved in:• ;Multicomponent reactions with nitriles and carboxylic acids followed by cyclocondensation for synthesis of enantiopure pyridines1• ;Intermolecular hydroamination2• ;One-pot synthesis of alkoxy and (alkylsulfanyl)-substituted pyrroles and dihydropyridines3• ;Intermolecular [4+2] cycloaddition with dienes4• ;Allenyl cyclization and subsequent transformation into dicarbonyl, cyclopentenones, and butenolide compounds5• ;Insertion reactions of C-C pi-bonds into alkylidenesilacyclopropanes6

UsesReactant involved in:Multicomponent reactions with nitriles and carboxylic acids followed by cyclocondensation for synthesis of enantiopure pyridinesIntermolecular hydroaminationOne-pot synthesis of alkoxy and (alkylsulfanyl)-substituted pyrroles and dihydropyridinesIntermolecular [4+2] cycloaddition with dienesAllenyl cyclization and subsequent transformation into dicarbonyl, cyclopentenones, and butenolide compoundsInsertion reactions of C-C pi-bonds into alkylidenesilacyclopropanes

Preparation methods · 1 item

PreparationMethoxyallene can be prepared on a tens-of-grams scale by the base-catalyzed isomerization of 1-methoxy-2-propyne (methyl propargyl ether). Related 1-alkoxy-1,2-propadiene ethers can be prepared similarly. A convenient version of this preparation has been reported.