3722-05-2

Basic information

• Product Name: Cyclopropane, 1,1-dichloro-2-(chloromethyl)-
• Synonyms: 2-chloromethyl-1,1-dichlorocyclopropane;2-chloromethyl-gem-dichlorocyclopropane;2,2-Dichloro-1-chloromethylcyclopropane;Cyclopropane,1,1-dichloro-2-(chloromethyl);1-chloromethyl-2,2-dichlorocyclopropane;1,1-dichloro-2-chloromethylcyclopropane
• CAS NO: 3722-05-2
• Molecular Formula: C4H5Cl3
• Molecular Weight: 159.443
• Mol File: 3722-05-2.mol

Chemical Properties

• Boiling Point: 56 °C(Press: 17 Torr)
• Density: 1.3205 g/cm3
• CAS DataBase Reference: Cyclopropane, 1,1-dichloro-2-(chloromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Cyclopropane, 1,1-dichloro-2-(chloromethyl)-(3722-05-2)
• EPA Substance Registry System: Cyclopropane, 1,1-dichloro-2-(chloromethyl)-(3722-05-2)

Safety Data

• Hazardous Substances Data: 3722-05-2(Hazardous Substances Data)

Upstream product

• 75-25-2 Bromoform 
• 107-05-1 3-chloroprop-1-ene 
• 67-66-3 chloroform 
• 106-95-6 allyl bromide 
• 75-27-4 bromodichloromethane 
• 107-18-6 allyl alcohol 

Downstream Products

• 24063-87-4 1,1-dichloro-2-(2-cyano-2-phenylethyl)cyclopropane 
• 1320363-63-0 2'-methylene-spiro[1,3-benzodioxolane-2,1'-cyclopropane] 
• 1227168-87-7 2-[(2,2-dichlorocyclopropyl)methoxy]phenol 
• 1246434-44-5 1,2-bis[(2,2-dichlorocyclopropyl)methoxy]benzene 
• 15954-38-8 (3,3-dichloro-1-methylprop-2-ene-1-yl)benzene 
• 1378866-59-1 1-(3,3-dichloro-1-methylprop-2-ene-1-yl)-4-methylbenzene 
• 1378866-58-0 1-(3,3-dichloro-1-methylprop-2-ene-1-yl)-2-methylbenzene 
• 1339375-31-3 N-benzyl-1-(2,2-dichlorocyclopropyl)methylamine 
• 144765-26-4 1-Chloro-4-(2,2-dichloro-cyclopropylmethoxy)-benzene 
• 144765-27-5 C₁₆H₁₂Cl₂O₂ 
• 397845-77-1 C₁₁H₁₂Cl₂O 
• 144765-30-0 C₁₈H₁₈O₂ 
• 1320363-65-2 C₁₄H₁₈Cl₂O₂ 
• 68618-71-3 (2',2'-dichlorocyclopropyl)-methylamine 

Relevant articles and documents

Steuerung einer Reaktionsverzweigung durch geeignete Phasentransfer-Katalysatoren. Anwendungen der Phasentransfer-Katalyse 37.

The influence of phase transfer catalyst structure on a branching of reaction paths is recorded.An almost complete change-over of mechanisms can be achieved.Reaction of allyl bromide with bromoform/sodium hydroxide/catalyst yields carbene adduct 1 and displacement products 2 and 3.Two new and unusual catalysts, AsPh4Cl and Cl, give substitution:addition 10:1, whereas NMe4Cl and benzo-15-crown-5 lead to 1:4, both at high conversions.

Reaktionssteuerung durch die Struktur eines Phasentransfer-Katalysators bei Tribrommethyl-Anion-/Dibromcarben-Umsetzungen

Control of Reactions with Tribromomethyl Anions/Dibromocarbene by the Nature of the Phase Transfer Catalyst Conversion of (substituted) allyl bromides with bromoform/sodium hydroxide/phase transfer catalyst may be directed towards dibromocarbene addition or substitution by tribromomethyl anion by choice of the catalyst.The observed effects (addition: substitution in the primary step variable between maximally 92:1 and 1:91) are by far the largest reported for specific catalyst influences.Small, hard cations favor the carbene route, sterically shielded and highly delocalized ones favor the substitution process.

REACTION OF DICHLOROCARBENE WITH ALLYL AND CINNAMYL ALCOHOLS

In the reaction of dichlorocarbene, generated by the phase-transfer method, with allyl and cinnamyl alcohols both the products from addition of the dichlorocarbene to the double bond and the products from substitution of the hydroxyl group by a chlorine atom and simultaneous addition of dichlorocarbene at the double bond are formed.

REACTION OF ALLYL HALIDES WITH HALOFORMS AND ALKALI UNDER THE CONDITIONS OF INTERPHASE CATALYSIS

The reaction of allyl halides with haloforms and alkali in the presence of interphase transfer catalysts gives cyclopropanes and 4,4,4-trihalogeno-1-butenes.The latter are formed by nucleophilic substitution of the halogen in the allyl halide by the trihalogenomethyl anion.