1000-30-2

Basic information

• Product Name: 2,2,5-trimethylhex-4-enal
• Synonyms: 2,2,5-trimethylhex-4-enal;2,2,5-Trimethyl-4-hexenal;4-Hexenal,2,2,5-trimethyl-
• CAS NO: 1000-30-2
• Molecular Formula: C₉H₁₆O
• Molecular Weight: 140.22274
• EINECS: 213-670-6
• Mol File: 1000-30-2.mol

Chemical Properties

• Boiling Point: 183.3°Cat760mmHg
• Flash Point: 57.5°C
• Appearance: /
• Density: 0.835g/cm³
• Vapor Pressure: 0.777mmHg at 25°C
• Refractive Index: 1.434
• CAS DataBase Reference: 2,2,5-trimethylhex-4-enal(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2,5-trimethylhex-4-enal(1000-30-2)
• EPA Substance Registry System: 2,2,5-trimethylhex-4-enal(1000-30-2)

Safety Data

• Hazardous Substances Data: 1000-30-2(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 19, p. 491, 1978 DOI: 10.1016/S0040-4039(01)91464-9

InChI:InChI=1/C9H16O/c1-8(2)5-6-9(3,4)7-10/h5,7H,6H2,1-4H3

Upstream product

• 6852-60-4 N-tert-butyl-2-methylpropanimine 
• 870-63-3 prenyl bromide 
• 91076-35-6 N-(2-methylpropylidene)-2-methyl-2-propanamine 
• 4541-35-9 2,2,5,5-tetramethylcyclopentanone 
• 115-18-4 2-methyl-3-buten-2-ol 
• 78-84-2 isobutyraldehyde 
• 503-60-6 3,3-dimethyl-allyl chloride 
• 78-79-5 isoprene 
• 53516-62-4 N-butyl-N-isobutyl-2-methylprop-1-enamine 
• 53965-16-5 2,2,5,5-tetramethylpent-4-en-1-ol 
• 83974-01-0 ethyl 2,2,5,5-tetramethylpent-4-enoate 

Downstream Products

• 127861-74-9 1-(5-Hydroxy-2,2,5-trimethyl-cyclohexyl)-propan-2-one 
• 128600-86-2 1,2-dichloro-3,3,6,6-tetramethyl-1-cyclohexene 
• 1891-45-8 7-epihimachalol 
• 67682-25-1 4-Brom-benzolsulfonsaeure-<1,2,2,5-tetramethyl-hex-4-enylester> 
• 1070859-40-3 C₂₁H₃₃N 

Relevant articles and documents

PREPARATION OF PRECURSORS OF CARBENES OF CAAC TYPE AND PREPARING SAID CARBENES THEREFROM

Precursors of carbenes of CAAC type (Cyclic)(Alkyl)(Amino)(Carbenes) are prepared and carbenes are produced therefrom; novel synthesis intermediates are provided for preparing the precursors of CAAC-type carbenes.

Intramolecular cyclopropanation of unsaturated terminal epoxides and chlorohydrins

Lithium 2,2,6,6-tetramethylpiperidide (LTMP)-induced intramolecular cyclopropanation of unsaturated terminal epoxides provides an efficient and completely stereoselective entry to bicyclo[3.1.0]hexan-2-ols and bicyclo[4.1.0]heptan-2-ols. Further elaboration of C-5 and C-6 stannyl-substituted bicyclo[3.1.0]-hexan-2-ols via Sn-Li exchange/electrophile trapping or Stille coupling generates a range of substituted bicyclic cyclopropanes. An alternative straightforward cyclopropanation protocol using a catalytic amount of 2,2,6,6-tetramethylpiperidine (TMP) allows for a convenient (1 g-7.5 kg) synthesis of bicyclo[3.1.0]-hexan-2-ol and other bicyclic adducts. The synthetic utility of this chemistry has been demonstrated in a concise asymmetric synthesis of (+)-β-cuparenone. The related unsaturated chlorohydrins also undergo intramolecular cyclopropanation via in situ epoxide formation.

Mechanistic dichotomy in CpRu(CH3CN)3PF6 catalyzed enyne cycloisomerizations

Enynes are easily accessible building blocks as a result of the rich chemistry of alkynes and thus represent attractive substrates for ring formation, A ruthenium catalyst for cycloisomerization effects such reaction of 1,6- and 1,7-enynes typically at room temperature in acetone or DMF under neutral conditions. The reaction is effective for forming five- and six-membered rings of widely divergent structure. The alkyne may bear both election-donating and election-withdrawing substituents. The alkene may be di- or trisubstituted. Introduction of a quaternary center at the propargylic position of an ynoate, however, completely changes the nature of the reaction. In the case of a 1,6-enynoate, a seven-membered ring forms in excellent yield under equally mild conditions. Evidence is presented to indicate a complete change in mechanism. In the former case, the reaction involves the intermediacy of a ruthenacyclopentene. In the latter case, a C-H insertion to form a π-allylruthenium intermediate is proposed and supported by deuterium-labeling studies. A rationale is presented for the structural dependence of the mechanism.

A novel photochemical synthesis of 5,6-dihydro-4H-1,2-oxazines by DCA-sensitized irradiation of γ,δ-unsaturated oximes

On DCA-sensitized irradiation 6,6-diphenylhex-5-en-2-one oxime 5a, 5,5-diphenylpent-4-enal oxime 5b and 2,2-dimethyl-5-phenylpent-4-enal oxime 5c undergo a novel photochemical cyclization yielding 3-methyl-6-diphenylmethyl-5,6-dihydro-4H-1,2-oxazine 9a, 6

Cyclic and Acyclic Products from the Addition of 1-Aza-Allyl Anions to Dienes and α,β-Unsaturated Ketones - Regioselectivity

Addition of 1-aza-allyl-lithium compound 1 to isoprene at low temperature yields two regioisomeric γ,δ-unsaturated imines 3, whereas at THF reflux temperature the cyclic regioisomeric cyclohexene derivatives 4 are formed.With 2,3-dimethylbutadiene, the ac

Synthesis of 2,2,5,5-Tetramethylcyclopentanecarboxylic Acid - A Building Block of an Amino Acid Sweetener

The title compound 2 is synthesized in three steps from readily available 2,5-dichloro-2,5-dimethylhexane (8) and vinylidene chloride (9).The key steps are carbocationic adition and cyclization reactions.