51421-17-1

Basic information

• Product Name: 4-METHYL-BENZYL-HYDRAZINE
• Synonyms: 4-METHYL-BENZYL-HYDRAZINE;(4-methylbenzyl)hydrazine(SALTDATA: HCl);[(4-methylphenyl)methyl]hydrazine
• CAS NO: 51421-17-1
• Molecular Formula: C₈H₁₂N₂
• Molecular Weight: 136.19
• Mol File: 51421-17-1.mol

Chemical Properties

• Boiling Point: 281.9°C at 760 mmHg
• Flash Point: 144.1°C
• Appearance: /
• Density: 1.012g/cm³
• Vapor Pressure: 0.00347mmHg at 25°C
• Refractive Index: 1.554
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• CAS DataBase Reference: 4-METHYL-BENZYL-HYDRAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-METHYL-BENZYL-HYDRAZINE(51421-17-1)
• EPA Substance Registry System: 4-METHYL-BENZYL-HYDRAZINE(51421-17-1)

Safety Data

• Hazardous Substances Data: 51421-17-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H12N2/c1-7-2-4-8(5-3-7)6-10-9/h2-5,10H,6,9H2,1H3

Upstream product

• 52693-87-5 4-methylbenzaldehyde hydrazone 
• 104-87-0 4-methyl-benzaldehyde 
• 106-42-3 para-xylene 
• 1068-57-1 acetic acid hydrazide 
• 104-82-5 4-Methylbenzyl chloride 
• 102955-76-0 3,3-bis-(4-methyl-benzyl)-carbazic acid benzyl ester 

Downstream Products

• 1354328-29-2 C₄₈H₄₆N₂O₄ 
• 1354328-31-6 C₆₃H₆₅N₅O₈ 
• 537672-68-7 N'-(4-bromobenzoyl)-4-methylbenzylhydrazine 
• 425675-44-1 1-[(4-methylphenyl)methyl]hydrazinecarboxamide 
• 25811-87-4 1-(4-methyl-benzyl)-semicarbazide 
• 1128073-03-9 ethyl 2-(4-(4-(2-carbamoyl-2-(4-methylbenzyl)hydrazinyl)-4-oxobutyl)phenoxy)-2-methylpropanoate 
• 425675-46-3 2-[4-[3-[4,5-dihydro-1-[(4-methylphenyl)methyl]-5-oxo-1H-1,2,4-triazol-3-yl]propyl]phenoxy]-2-methylpropanoic acid ethyl ester 
• 425671-29-0 LY 518674 
• 1623023-33-5 7-methyl-1-(4-methylbenzyl)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2c]pyrazole-3-carboxylic acid 

Relevant articles and documents

Heteroaromatic moieties in the sphingosine backbone of α- Galactosylceramides for noncovalent interactions with CD1d

A series of α-GalCer analogues containing heterocyclic and aromatic moieties in the sphingosine backbone were synthesized to improve the selectivity in the Th1/Th2 cytokine profile via noncovalent interaction with three aromatic residues at the binding pocket of CD1d. In vitro and in vivo biological evaluations revealed the treatment of α-GalCer analogue (6) induced the selective stimulation of natural killer T cells to facilitate the secretion of Th2 cytokines.

A convergent kilogram-scale synthesis of the PPARα Agonist LY518674: Discovery of a novel acid-mediated triazolone synthesis

The first kilogram-scale synthesis of the PPARα agonist LY518674 (1) is described. The de novo convergent synthetic approach involved coupling of two rapidly assembled components, triazolone formation via a novel acid-promoted cyclization reaction, and final step saponification, delivering the compound in 32.5% overall yield via eight total steps with a six-step longest linear sequence. A regioselective alkylation on the dianion of 4-hydroxyphenylbutyric acid allowed the direct preparation of one of the convergent coupling partners, carboxylic acid 12, and an unusual solvent effect enabled the installation of a urea group on a protected hydrazine, permitting the regiospecific preparation of the other coupling partner, semicarbazide mesylate 17. Sulfonic acids were found to effect the desired triazolone ring formation, affording 25 from the coupled precursor acyl semicarbazide 23. Following saponification of 25 to 1, a wide solubility differential between ethyl acetate extracts of 1 and solutions of 1 in anhydrous ethyl acetate was harnessed in the final crystallization step to deliver the final compound in high yield and purity. The novel acid-mediated triazolone formation was further evaluated on a range of additional substrates, showing the new methodology to be largely complementary to existing base-mediated triazolone syntheses.

Mechanisms of benzyl group transfer in the decay of (E)-arylmethanediazoates and aryldiazomethanes in aqueous solutions

Rate constants are reported for the buffer-independent decay of ten (E)-arylmethanediazoates in aqueous media at 25 °C, ionic strength 1 M (NaClO4), 4% 2-propanol, in the region of pH 4-12. The rate constants are proportional to hydrogen ion concentration at high pH and become pH independent in the low-pH region. Varying concentrations of oxyanion, amine, and hydrazine buffers over the range 0.05-0.2 M increased the pseudo-first-order rate constant for decay of the diazoates by less than 10%. The azide - water selectivities, ka/ks, for partitioning of the benzyl groups in the decay of (E)-(3,5-bis(trifluoromethyl)phenyl)methanediazoate and the (3,5-bis(trifluoromethyl)phenyl)diazomethane are determined to be 0.20 and 0.21 M-1, respectively, in phosphate buffered water and 0.27 and 0.26 M-1, respectively, in 20/80 DMSO-water. It is concluded that these two reactants decompose, in these media, via a common free diazonium ion intermediate that is formed in the case of the diazoate upon unassisted N-O bond cleavage of the diazoic acid. A common rate-limiting step is indicated for all the diazoates by the correlation line for the plot of log k1, the pH independent rate constant, against σ that has a slope q = -1.23. Product ratios for trapping of benzyl groups derived from other pairs of arylmethanediazoates and aryldiazomethanes with less electron withdrawing groups are different outside experimental error, indicating the importance of different nitrogen-separated ion pairs in these reactions. The (E)-(p-methoxy)phenyl)methane-16O-diazoate decomposes in 16O/18O water to give alcohol that has an "excess" abundance of 16O compared to solvent. Decomposition of the same compound in 50/50 trifluoroethanol-water with varying concentrations of azide indicates that azide ion appears to trap a limiting amount, ～80%, of the p-methoxybenzyl group. Quantitative analysis of the data indicates that 16% of the p-methoxybenzyl cation is trapped by solvent at the nitrogen-separated ion pair stage, in the absence of azide ion. There is a 9-fold enhancement of selectivity for trifluoroethanol at the ion pair stage that is ascribed to a proton switch initiated by the leaving hydroxide ion in the ion pair. The values of Ka/ks ～ 0.2 M-1 and kT/kH ～ 0.5-0.6 for the trifluoroethanol-water selectivity and kET/kT ～ 1 for the ethanol-trifluoroethanol selectivity are independent of substituent in the decay of arylmethanediazoates (X = H and EWG) in water, water-trifluoroethanol (50/50), and water-trifluoroethanol-ethanol (50/40/10), respectively. It is concluded from this that the productdetermining steps do not involve chemical bonding but rather rotational/translational reorientation of the nucleophiles in the first solvation sphere of the carbocation intermediates. It is concluded that the values of kH/kT = 0.5-0.6 indicate preferential solvation of the cation precursor by trifluoroethanol. It is shown that a preferential interaction for trifluoroethanol of 1 kcal/mol is required to generate the observed selectivities.

1-Substituted-3-amino-pyrazol-5-ones

Pharmaceutical compositions are prepared which comprise a diuretically effective amount, a saluretically effect amount or an antihypertensive amount of a compound of the formula SPC1 Or a pharmaceutically acceptable non-toxic salt thereof, wherein R is aryl which is either unsubstituted or substituted by A. 1, 2 or 3 identical or different substituents selected from the group consisting of halogen, alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 8 carbon atoms, alkenoxy of 2 to 6 carbon atoms, cycloalkyl of 5 to 7 carbon atoms, trifluoromethyl, trifluoromethoxy and phenyl; B. 1 or 2 identical or different substituents selected from the group consisting of nitro, cyano, lower alkylamino of 1 to 4 carbon atoms, a carbonamido moiety of the formula EQU1 and a sulphonamido moiety of the formula EQU2 wherein R1 and R2 are each hydrogen or straight or branched chain alkyl of 1 to 4 carbon atoms, or R1 and R2 together with the nitrogen atom to which they are attached are linked together to form a 5-, 6- or 7-membered heterocyclic ring wherein the nitrogen atom is the only heteroatom or wherein oxygen is also present as a ring member; C. one substituent selected from the group consisting of dialkylamino of 1 to 4 carbon atoms in each alkyl moiety, nitro, cyano and SOn -alkyl of 1 to 4 carbon atoms, wherein n is 0, 1 or 2; D. one substituent selected from the group consisting of a moiety of the formula EQU3 wherein R1 and R2 are as above defined, nitro, cyano, a carbonamido moiety of the formula EQU4 wherein R1 and R2 are as above defined, a sulphonamide moiety of the formula EQU5 wherein R1 and R2 are as above defined, and SOn -alkyl of 1 to 4 carbon atoms, wherein n is 0, 1 or 2, and 1 or 2 substituents selected from the group consisting of alkyl of 1 to 8 carbon atoms, alkoxy of 1 to 6 carbon atoms, halogen and trifluoromethyl; E. an annellated-branched or unbranched, saturated or unsaturated, 5-, 6- or 7-membered isocyclic or heterocyclic ring having 1 or more heteroatoms selected from the group consisting of oxygen and sulphur and wherein said aryl moiety is either unsubstituted or chlorosubstituted; F. --O--(CH2)n' --N(alkyl)2, wherein the alkyl groups contain a total of 2 to 4 carbon atoms and n'is 2 or 3; or G. two different substituents selected from the group consisting of alkyl of 1 to 8 carbon atoms, phenyl, halogen, alkoxy of 1 to 8 carbon atoms, trifluoromethyl, trifluoromethoxy, lower alkylamino, nitro, cyano, SOn --alkyl of 1 to 4 carbon atoms, wherein n is 0, 1 or 2, a carbonamido moiety of the formula EQU6 and a sulphonamido moiety of the formula EQU7 wherein R3 and R4 are each hydrogen or alkyl of 1 to 4 carbon atoms; in combination with a pharmaceutically acceptable non-toxic inert diluent or carrier. Diuretic therapy, saluretic therapy and antihypertensive therapy is effected in humans and animals by administering an effective amount of the active ingredient as above defined.