82700-43-4

Basic information

• Product Name: 2-Benzylidenemalonaldehyde
• Synonyms: 2-Benzylidenemalonaldehyde;Benzylidenemalonaldehyde
• CAS NO: 82700-43-4
• Molecular Formula: C₁₀H₈O₂
• Molecular Weight: 0
• Mol File: 82700-43-4.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Benzylidenemalonaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Benzylidenemalonaldehyde(82700-43-4)
• EPA Substance Registry System: 2-Benzylidenemalonaldehyde(82700-43-4)

Safety Data

• Hazardous Substances Data: 82700-43-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 3163, 1982 DOI: 10.1016/S0040-4039(00)88585-8

Upstream product

• 99554-14-0 2-(2,4,6-Cycloheptatrien-1-yl)-1,3-propandial 
• 83920-13-2 5-Formyl-4-phenyl-α-(phenylmethylen)-4H-1,3-dioxin-2-acetaldehyd 
• 100-52-7 benzaldehyde 
• 1611-78-5 1,3-bis-dimethylaminotrimethinium perchlorate 
• 7338-50-3 6-phenylfulvene 

Downstream Products

• 83920-13-2 5-Formyl-4-phenyl-α-(phenylmethylen)-4H-1,3-dioxin-2-acetaldehyd 
• 99554-15-1 2-Brom-2-(α-brombenzyl)-1,3-propandial 
• 104409-69-0 2-Dimethylamino-4-phenyl-4H-[1,3]oxazine-5-carbaldehyde 
• 99554-16-2 <α-(Phenylthio)benzyl>malonaldehyd 
• 99554-16-2 <α-(Phenylthio)benzyl>malonaldehyd 
• 99554-18-4 (E)-2-(α-Methoxybenzyl)-3-(4-nitroanilino)-2-propenal 
• 99554-20-8 (Z)-2-(α-Methoxybenzyl)-3-(4-nitroanilino)-2-propenal 
• 99554-19-5 (E)-2-(α-Ethoxybenzyl)-3-(4-nitroanilino)-2-propenal 
• 99554-21-9 (Z)-2-(α-Ethoxybenzyl)-3-(4-nitroanilino)-2-propenal 
• 88382-33-6 4-Formyl-3-phenyl-3H-furan-2,2-dicarboxylic acid diethyl ester 
• 146514-79-6 6-Ethoxy-4-phenyl-5,6-dihydro-4H-pyran-3-carbaldehyde 
• 108155-43-7 (2-Diethoxymethyl-3,3-diethoxy-propenyl)-benzene 

Relevant articles and documents

Reaction of Benzylidenemalonaldehyde with Water and Hydroxide Ion

A stopped-flow kinetic study of the title reaction is reported from which rate and equilibrium constants of various elementary processes are deduced.

Kinetics of Amine Addition to Benzylidenemalonodialdehyde in 50percent Me2SO-50percent water

The kinetics of the reaction of benzylidenemalonodialdehyde with piperidine, morpholine, n-butylamine, 2-methoxyethylamine, glycinamide, glycine ethyl ester, cyanomethylamine, and semicarbazide have been determined in 50percent aqueous Me2SO at 20 deg C.The reaction leads to a zwitterionic adduct, PhCH(RR'NH(1+))C(CHO)2(1-) (TA(+/-)), that is in fast acid-base equilibrium with the anionic adduct, PhCH(RR'N)C(CHO)2(1-) (TA(1-)).With strongly basic amines at high pH there is also attack of the amine on one of the carbonyl groups, which acts as a rapid preequilibrium.Rate constants for the formation of TA(+/-) (k1) and its reverse (k-1), as well as equilibrium constants (K1 = k1/k-1) and the pKa of TA(+/-) were determined for all the amines.Intrinsic rate constants (k0 = k1 = k-1 when K1 = 1) were calculated.The intrinsic rate constants are lower than those for amine addition to benzylidene Meldrum's acid.This is consistent with the greater role played by resonance in stabilizing TA(+/-) derived from benzylidenemalonodialdehyde.However, k0 for piperidine/morpholine addition to benzylidenemalonodialdehyde is much higher than for the reaction of benzylideneacetylacetone with the same amines, indicating that the rate-depressing effect of intramolecular hydrogen bonding in TA(+/-) derived from benzylidenemalonodialdehyde is much smaller than that in TA(+/-) derived from benzylideneacetylacetone.Even though semicarbazide is an α-effect nucleophile, no enhancement of k1 was observed, but K1, estimated on the basis of a structure-reactivity relationship, is larger than expected based on the pKa of the amine.This result is attributed to a low νnucn value.

Syntheses with Aliphatic Dialdehydes, XLI. - Benzylidenemalonaldehyde - Synthesis, Structure, and Reactions

Unexpectedly, the oxidation of (cycloheptatrienyl)malonaldehyde (1) with silver(I) oxide or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone does not give (cycloheptatrienylidene)malonaldehyde (2), but yields the hitherto unknown benzylidenemalonaldehyde (3) whi