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Acetone hydrazone information


Acetone hydrazone
Names
IUPAC name
Propan-2-ylidenehydrazine
Other names
Isopropylidenehydrazine
Identifiers
CAS Number
  • 5281-20-9 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 71270
EC Number
  • 226-110-0
PubChem CID
  • 78937
CompTox Dashboard (EPA)
  • DTXSID10967276 Edit this at Wikidata
InChI
  • InChI=1S/C3H8N2/c1-3(2)5-4/h4H2,1-2H3
    Key: JIQXKYSNGXUDJU-UHFFFAOYSA-N
SMILES
  • CC(=NN)C
Properties
Chemical formula
C3H8N2
Molar mass 72.111 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
GHS02: FlammableGHS05: CorrosiveGHS06: ToxicGHS08: Health hazardGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H226, H301, H311, H314, H331, H351, H411
Precautionary statements
P203, P210, P233, P240, P241, P242, P243, P260, P261, P264, P270, P271, P273, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P318, P321, P330, P361+P364, P363, P370+P378, P391, P403+P233, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Acetone hydrazone (isopropylidenehydrazine) is the product of condensation of acetone and hydrazine, as typical for hydrazone formation. It is an intermediate in the synthesis of 2-diazopropane [fr].[2]

Acetone hydrazone can be produced on large scale by reaction of acetone azine with hydrazine, a more convenient reaction than direct reaction of acetone and hydrazine.[3] Likewise, it is susceptible to disproportionation to revert to acetone azine and hydrazine, especially in the presence of water.[3]

The chemical is one of the metabolic products of the antihypertensive pharmaceutical hydralazine, and itself also have antihypertensive effects.[4]

  1. ^ "Acetone hydrazone". pubchem.ncbi.nlm.nih.gov.
  2. ^ Andrews, S. D.; Day, A. C.; Raymond, P.; Whiting, M. C. (1970). "2-Diazopropane". Organic Syntheses: 27; Collected Volumes, vol. 6, 1988, p. 392.
  3. ^ a b Day, A. C.; Whiting, M. C. "Acetone Hydrazone". Organic Syntheses; Collected Volumes, vol. 6, p. 10.
  4. ^ Cohn JN, McInnes GT, Shepherd AM (2011). "Direct-acting vasodilators". Journal of Clinical Hypertension. 13 (9): 690–692. doi:10.1111/j.1751-7176.2011.00507.x. PMC 8108999. PMID 21896152.

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Acetone hydrazone

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Acetone hydrazone (isopropylidenehydrazine) is the product of condensation of acetone and hydrazine, as typical for hydrazone formation. It is an intermediate...

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Hydrazone

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Collected Volumes, vol. 6, p. 242. Day, A. C.; Whiting, M. C. (1970). "Acetone hydrazone". Organic Syntheses. 50: 3; Collected Volumes, vol. 6, p. 10. Fischer...

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Acetone azine

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ammonia to produce acetone hydrazone. The hydrazone then condenses with a further molecule of acetone to produce the azine. The acetone azine product is...

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Hydrazine

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carbonyl is its reaction with acetone to give the acetone azine. The latter reacts further with hydrazine to yield acetone hydrazone: 2 (CH3)2CO + N2H4 → 2 H2O...

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Hydralazine

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Metabolic products include the N-acetyl derivative, pyruvic acid hydrazone, and acetone hydrazone, each of which may also contribute to reducing blood pressure...

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Diazo

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2-diazopropane [fr] from acetone hydrazone. Other oxidizing reagents are lead tetraacetate, manganese dioxide and the Swern reagent. Tosyl hydrazones RRC=N-NHTs are...

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Azine

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doi:10.1002/14356007.a13_177. Day, A. C.; Whiting, M. C. (1970). "Acetone Hydrazone". Organic Syntheses. 50: 3. doi:10.15227/orgsyn.050.0003. Lasri, Jamal;...

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Ketone

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(which contains a carbon–oxygen double bond C=O). The simplest ketone is acetone (where R and R' is methyl), with the formula (CH3)2CO. Many ketones are...

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Triamcinolone acetonide

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16α-17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16,17-acetal with acetone, is a synthetic halogenated cyclic ketal pregnane corticosteroid. It is...

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C3H8N2

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C3H8N2 (molar mass: 72.11 g/mol, exact mass: 72.0688 u) may refer to: Acetone hydrazone Imidazolidine Pyrazolidine This set index page lists chemical structure...

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Benzylideneacetone

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Benzylideneacetone can be efficiently prepared by the base-induced condensation of acetone and benzaldehyde: CH3C(O)CH3 + C6H5CHO → C6H5CH=CHC(O)CH3 + H2O However...

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Peroxide process

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with a second molecule of ammonia to give the hydrazone: Me(Et)CONH + NH3 → Me(Et)C=NNH2 + H2O The hydrazone then condenses with a second equivalent of ketone...

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Uncoupler

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phenylhydrazone (CCP) Carbonyl cyanide m-chlorophenyl hydrazone (CCCP) Carbonyl cyanide-p-trifluoromethoxyphenyl hydrazone (FCCP) CDE (4β-cinnamoyloxy,1β,3α-dihydroxyeudesm-7...

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Oxime

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oximes are 102- to 103-fold more resistant to hydrolysis than analogous hydrazones. Oximes can be synthesized by condensation of an aldehyde or a ketone...

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Organic peroxides

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Methyl ethyl ketone peroxide, benzoyl peroxide and to a smaller degree acetone peroxide are used as initiators for radical polymerization of some thermosets...

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Carbonyl group

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within a carbonyl compound decreases. The pKa values of acetaldehyde and acetone are 16.7 and 19 respectively, Infrared spectroscopy: the C=O double bond...

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Acetyl group

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formation (ΔfH⦵298) −15 to −9 kJ mol−1 Related compounds Related compounds Acetone Carbon monoxide Acetic acid Except where otherwise noted, data are given...

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Organic selenocyanates

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treatment of potassium selenocyanate with alkyl halides in alcohol or acetone solution. Aryl selenocyanates are generally prepared by treatment of potassium...

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Nicolaou Taxol total synthesis

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aldehyde 4.2 and hydrazone 3.6 using a Shapiro coupling reaction. Retrosynthetic Scheme II indicates that both the aldehyde and the hydrazone used in the Shapiro...

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Functional group

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-amine Trimethylamine 4° ammonium ion R4N+ ammonio- -ammonium Choline Hydrazone R'R"CN2H2 hydrazino- -hydrazine Imine Primary ketimine RC(=NH)R' imino-...

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Urea

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Nitrogen Amine Enamine Ammonium Hydrazo Nitrene Imine Oxime Hydrazone Azo Amide Imidate Amidine Carbamate Imide Nitrile Isonitrile Cyanate Isocyanate...

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Thioketone

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group. Thus the simplest thioketone is thioacetone, the sulfur analog of acetone. Unhindered alkylthioketones typically tend to form polymers or rings....

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Pharmacokinetics of progesterone

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(hydroxyprogesterone enanthate) Hydroxyprogesterone heptanoate benzilic acid hydrazone Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone...

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Methyl group

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can be deprotonated. For example, the acidity of the methyl groups in acetone ((CH3)2CO) is about 1020 times more acidic than methane. The resulting...

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Algestone acetonide

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(hydroxyprogesterone enanthate) Hydroxyprogesterone heptanoate benzilic acid hydrazone Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone...

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Azo compound

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azo compounds pose the risk of explosion. AIBN is produced by converting acetone cyanohydrin to the hydrazine derivative followed by oxidation: 2 (CH3)2C(CN)OH...

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Proline organocatalysis

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These proline-derived auxiliaries and catalysts, including the Enders hydrazone reaction and Corey–Itsuno reduction, have been reviewed, as have MacMillan’s...

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Hydrazines

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formed by the oxidation of diphenylamine with potassium permanganate in acetone. Hydrazines can be divided into three groups according to the degree of...

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Apigenin

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(hydroxyprogesterone enanthate) Hydroxyprogesterone heptanoate benzilic acid hydrazone Mecigestone (pentarane B) Medrogestone Medroxyprogesterone Medroxyprogesterone...

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Acetal

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sometimes called a formal or the methylenedioxy group. The acetal formed from acetone is sometimes called an acetonide. Used in a more general sense, the term...

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