1124-13-6

Basic information

• Product Name: TRANS-CYCLOBUTANE-1,2-DICARBOXYLIC ACID
• Synonyms: SPECS AB-131/40227215;RARECHEM AL BO 2332;TRANS-1,2-CYCLOBUTANEDICARBOXYLIC ACID;TRANS-CYCLOBUTANE-1,2-DICARBOXYLIC ACID;(e)-2-cyclobutanedicarboxylicacid;1,2-Cyclobutanedicarboxylic acid;1,2-Cyclobutanedicarboxylic acid, (E)-;1,2-Cyclobutanedicarboxylic acid, trans-
• CAS NO: 1124-13-6
• Molecular Formula: C6H8O4
• Molecular Weight: 144.13
• EINECS: 214-392-8
• Product Categories: C6;Carbonyl Compounds;Carboxylic Acids
• Mol File: 1124-13-6.mol
• Article Data: 5

Chemical Properties

• Melting Point: 125-131 °C
• Boiling Point: 397.8°C at 760 mmHg
• Flash Point: 194.4°C
• Appearance: /
• Density: 1.407g/cm³
• Vapor Pressure: 1.55E-06mmHg at 25°C
• Refractive Index: 1.4556 (589.3 nm 25℃)
• Storage Temp.: 2-8°C
• PKA: pK1:3.79 ;pK2:5.61 (25°C)
• BRN: 3198993
• CAS DataBase Reference: TRANS-CYCLOBUTANE-1,2-DICARBOXYLIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: TRANS-CYCLOBUTANE-1,2-DICARBOXYLIC ACID(1124-13-6)
• EPA Substance Registry System: TRANS-CYCLOBUTANE-1,2-DICARBOXYLIC ACID(1124-13-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• RTECS: GU1680000
• Hazardous Substances Data: 1124-13-6(Hazardous Substances Data)

Usage

General Description

The interaction of the carboxyl groups in the fragmentation of the molecular ions of cis-cyclobutane-1,2-dicarboxylic acid helps to distinguish it from trans-cyclobutane-1,2-dicarboxylic acid.

Purification Methods

Crystallise the acid from *C6H6 or *C6H6/EtOAc. The diphenacyl ester has m 98o (from EtOH) and the p-bromodiphenacyl ester has m 158o (from EtOH). The cis-acid isomerizes to the trans-acid on heating in conc HCl at 190o. [Reed J Chem Soc 685 1951, Fison et al. J Am Chem Soc 51 1536 1929, Fison et al. J Am Chem Soc 56 1774 1934, pK: Bode Chem Ber 67 332 1934, Beilstein 9 IV 2788.]

InChI:InChI=1/C11H11Cl2NO/c12-8-5-2-6-9(13)10(8)14-11(15)7-3-1-4-7/h2,5-7H,1,3-4H2,(H,14,15)

Upstream product

• 16177-46-1 cis-1,2-divinylcyclobutane 
• 98493-33-5 1,2-bis-methanesulfonyl-cyclobutane-1,2-dicarboxylic acid diamide 
• 4933-62-4 all-cis-3,4-Dibrom-cyclobutan-dicarbonsaeure-(1,2)-anhydrid 
• 89799-95-1 3,3,4,4-Tetrachloro-cyclobut-1-ene-1,2-dicarboxylic acid 
• 4462-96-8 3-oxabicyclo[3.2.0]heptane-2,4-dione 
• 7732-18-5 water 
• 7209-06-5 2-chloro-adipic acid diethyl ester 
• 7209-01-0 diethyl 2-bromoadipate 
• 2144-31-2 cyclobutane-1,1,2-tricarboxylic acid 
• 124-04-9 Adipic acid 
• 868-72-4 dimethyl 2,5-dibromohexanedioate 
• 29548-86-5 2,5-dibromohexanedioyl dichloride 
• 14132-45-7 dimethyl 1-cyanocyclobutane-1,2-dicarboxylate 
• 111-50-2 Adipic acid dichloride 

Downstream Products

• 4462-96-8 3-oxabicyclo[3.2.0]heptane-2,4-dione 
• 1124-13-6 (+/-)-(1S,2S)-cyclobutane-1,2-dicarboxylic acid 
• 5387-06-4 (+/-)-cis-2-benzoyl-cyclobutane-carboxylic acid-⁽¹⁾ 
• 10268-82-3 diethyl trans-1,2-cyclobutanedicarboxylate 
• 79455-23-5 trans-cyclobutane-dicarbanilide-(1.2) 
• 7371-64-4 trans-(cyclobutane-1,2-diyl)dimethanol 
• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 70014-01-6 1,2-dibenzoyl-cyclobutane 
• 3668-43-7 trans-cyclobutane-1,2-dicarbonyl dichloride 
• 704890-11-9 (-)-(1S,2S)-cyclobutane-1,2-dicarboxylic acid di(-)-menthyl ester 
• 22334-15-2 (+/-)-trans-cyclobutane-dicarboxylic acid-(1.2)-diamide 
• 1359850-68-2 C₁₈H₂₀F₂N₆OS 
• 1359850-66-0 C₁₈H₂₀F₂N₆OS 
• 1160960-99-5 C₅₉H₆₁N₁₃O₁₂S₆ 

Relevant articles and documents

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MACROCYCLIC SPIROETHERS AS MCL-1 INHIBITORS

Provided are compounds represented by Formula (I-A) and the pharmaceutically acceptable salts and solvates thereof, wherein R8, R9a, R9b, R9c, R9d, X, Y, Z, Z1, W, and (aa) are as defined as set forth in the specification. Provided are also compounds of Formula (I-A) for use to treat a condition or disorder responsive to Mcl-1 inhibition such as cancer.

Elimination and Addition Reactions. Part 43. Eliminative Fission of Cyclobutanes and the Relationship between Strain and Reactivity in Cyclobutanes and Cyclopropanes

Eliminative fission of cyclobutanes has been compared with that of analogous cyclopropanes; reactivity differences of 103.7-104.8 have been determined.In both sets of compounds, mechanisms have been shown to involve rate-determining ring fission.The possibilities that the large reactivity differences between the comparably strained systems are due either to peculiarity in the cyclobutane structures or to their abnormally slow deprotonation are rejected.Analysis of strain in the two systems suggests that as ring fission occurs, dispersal of the excess of enthalpy of the cyclobutanes is a less sensitive function of extension of a bond in the ring than for the cyclopropanes.The behaviour of these systems is compared with cleavage of cyclopropanes and cyclobutanes in other reactions; the results are remarkably similar.Calculations using the MINDO3 programme have been carried out for eliminative fissions of cyclopropylmethyl and cyclobutylmethyl carbanions.These reproduce remarkably closely the difference between the heats of formation of the species at the energy maxima for fission of each ring size; the maximum for fission of the cyclobutane is considerably displaced along the reaction co-ordinate towards product.