15963-46-9

Basic information

• Product Name: Methyl 3-chlorocyclobutanecarboxylate
• Synonyms: Methyl 3-chlorocyclobutanecarboxylate;3-Chlorocyclobutanecarboxylic acid methyl ester;methyl 3-chlorocyclobutane-1-carboxylate
• CAS NO: 15963-46-9
• Molecular Formula: C₆H₉ClO₂
• Molecular Weight: 148.58746
• Mol File: 15963-46-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 185℃
• Flash Point: 77℃
• Appearance: /
• Density: 1.18
• Vapor Pressure: 0.7mmHg at 25°C
• Refractive Index: 1.461
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• CAS DataBase Reference: Methyl 3-chlorocyclobutanecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 3-chlorocyclobutanecarboxylate(15963-46-9)
• EPA Substance Registry System: Methyl 3-chlorocyclobutanecarboxylate(15963-46-9)

Safety Data

• Hazardous Substances Data: 15963-46-9(Hazardous Substances Data)

Usage

General Description

Methyl 3-chlorocyclobutanecarboxylate is a chemical compound with the molecular formula C6H9ClO2. It is an ester, derived from the reaction of methyl alcohol and 3-chlorocyclobutanecarboxylic acid. Methyl 3-chlorocyclobutanecarboxylate is widely used in the pharmaceutical industry as a building block for the synthesis of various drugs and pharmaceutical products. It is also used in the production of flavors and fragrances. Methyl 3-chlorocyclobutanecarboxylate is a colorless, oily liquid with a faint odor, and it is considered to be stable under normal conditions. However, it should be handled with care as it can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation. Overall, this compound plays a significant role in the synthesis of various important chemical products.

InChI:InChI=1/C6H9ClO2/c1-9-6(8)4-2-5(7)3-4/h4-5H,2-3H2,1H3

Upstream product

• 186581-53-3 diazomethane 
• 35207-71-7 3-chlorocyclobutane-1-carboxylic acid 
• 67-56-1 methanol 
• 23745-75-7 3-chlorobicyclobutane-1-carbonitrile 
• 765-85-5 methyl cyclobutanecarboxylate 
• 30494-32-7 3-chlorocyclobutane carboxylic acid chloride 
• 89582-02-5 3-Chlor-1,1-cyclobutandicarbonsaeure-dichlorid 
• 51816-01-4 cyclobutane-1,1-dicarboxylic acid dichloride 
• 89639-43-0 3-chlorocyclobutane-1,1-dicarboxylic acid 
• 5445-51-2 cyclobutane-1,1'-dicarboxylic acid 
• 20249-18-7 3-chlorocyclobutanecarbonitrile 

Downstream Products

• 15963-47-0 3-chlorocyclobutanemethanol 
• 1212823-38-5 cis-3-aminocyclobutane-1-carboxylic acid methyl ester 
• 766458-70-2 methyl (1r,3r)-3-aminocyclobutane-1-carboxylate 
• 74307-75-8 (1r,3r)-3-aminocyclobutane-1-carboxylic acid 
• 74316-27-1 cis-3-aminocyclobutane-1-carboxylic acid 
• 1263284-46-3 3-phenoxycyclobutanecarboxylic acid 
• 30493-99-3 Bicyclo<1,1,0>butan-1-carboxylsaeure 
• 124490-70-6 3-benzyloxymethyl-1-cyclobutene 
• 124490-69-3 [[(3-Chlorocyclobutyl)methoxy]methyl]benzene 
• 4935-01-7 methyl bicyclo<1.1.0>butane-1-carboxylate 

Relevant articles and documents

Bridgehead substituents effect on the reactivity of bicyclobutane in its reactions with nucleophiles. A comparison with olefinic systems

The reactivity of bridgehead substituted bicyclobutanes towards nucleophilic attack was compared with that of the analogous vinylic compounds. Ab initio calculations suggest that the substituents exert nearly the same energetic effects on the ground state of the two systems. The observed difference in the reactivity of the two systems stems, therefore, from the different nature of corresponding transition states.

Prediction and Experimental Verification of the Stereoselective Electrocyclization of 3-Formylcyclobutene

3-Formylcyclobutene has been synthesized from cyclobutene-1, 1-dicarboxylic acid; it opens at 25-70 deg C with an activation energy of 27 +/- 1 kcal/mol to give exclusively (> 98percent) the Z product, in accord with predictions.

Atomic motions and protonation stereochemistry in nucleophilic additions to bicyclobutanes

Several nucleophilic reactions on bicyclobutanes activated at the gehead carbon by electron withdrawing groups (SO2Ph, CO2Me, COPh, and CN) were performed in MeOH. In all cases, the less stable 1,3-disubstituted cyclobutanes isomer was preferentially obtained (compared to the equilibrium ratio). The results for the two charge localizing groups CN and SO2Ph oppose the existing knowledge regarding the protonation stereochemistry of such carbanions. Ab initio calculations (6-31G*) have shown that as the nucleophile approaches the bicyclobutane, the bridgehead activating group moves inward toward an axial position. With a charge localizing group (CN and S(H)SO2) the carbanion remains pyramidal, whereas with C(H)=O as an activating group, the carbanion is nearly planar. It is suggested therefore that under conditions where the carbanion undergoes rapid protonation, it is trapped in its initial pyramidal geometry. Whereas, in cases where the lifetime of the carbamon is long enough to allow appreciable equilibration, protonation may result in a different product distribution. This hypothesis was tested by slowing down the protonation rates. As a result, the more stable isomer was indeed preferentially obtained.