589-18-4 Usage
Description
4-Methylbenzyl alcohol, also known as p-methylbenzyl alcohol or 4-methylbenzyl alcohol, is an organic compound with the chemical formula C8H9O. It is a colorless liquid with a strong, floral odor and is soluble in water. It is commonly used as a fragrance ingredient and as a precursor in the synthesis of various chemicals.
Uses
Used in Perfumery:
4-Methylbenzyl alcohol is used as a fragrance ingredient in perfumes and colognes due to its strong, floral scent. It is often used in combination with other fragrance ingredients to create complex and long-lasting scents.
Used in Flavoring:
4-Methylbenzyl alcohol is used as a flavoring agent in food and beverages, particularly in products with a floral or fruity taste. It is used to enhance the flavor profile and provide a pleasant aroma.
Used as a Laboratory Reagent:
4-Methylbenzyl alcohol is used as a laboratory reagent in various chemical reactions and processes. It is used as a solvent, a reducing agent, and a starting material for the synthesis of other organic compounds.
Used in the Preparation of Polycarbonates:
4-Methylbenzyl alcohol is used as a raw material in the production of polycarbonates, which are high-performance polymers with a wide range of applications, including automotive parts, electronic devices, and construction materials.
Used in the Preparation of 4-Methylbenzaldehyde:
4-Methylbenzyl alcohol is also used as a raw material in the synthesis of 4-methylbenzaldehyde, which is an important intermediate in the production of various pharmaceuticals, agrochemicals, and fragrances.
Production Methods
p-Tolyl alcohol is commercially prepared by reducing p-tolyl
aldehyde. It is used mainly in fragrances, and the
major route of exposure is likely to be dermal contact.
Synthesis Reference(s)
The Journal of Organic Chemistry, 52, p. 946, 1987 DOI: 10.1021/jo00381a047
Air & Water Reactions
Slightly soluble in water.
Reactivity Profile
4-Methylbenzyl alcohol can react with acids, acid chlorides, acid anhydrides and oxidizing agents.
Health Hazard
ACUTE/CHRONIC HAZARDS: When heated to decomposition 4-Methylbenzyl alcohol emits acrid smoke and toxic fumes of carbon monoxide and carbon dioxide.
Fire Hazard
Flash point data for 4-Methylbenzyl alcohol are not available. 4-Methylbenzyl alcohol is probably combustible.
Flammability and Explosibility
Notclassified
Purification Methods
Crystallise the alcohol from pet ether (b 80-100o, 1g/mL), Et2O, pentane or H2O (m 61-62.1o). It can also be distilled in a vacuum. [Beilstein 6 H 498, 6 I 248, 6 II 469, 6 III 1779.]
Check Digit Verification of cas no
The CAS Registry Mumber 589-18-4 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,8 and 9 respectively; the second part has 2 digits, 1 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 589-18:
(5*5)+(4*8)+(3*9)+(2*1)+(1*8)=94
94 % 10 = 4
So 589-18-4 is a valid CAS Registry Number.
InChI:InChI=1/C8H10O/c1-7-2-4-8(6-9)5-3-7/h2-5,9H,6H2,1H3
589-18-4Relevant articles and documents
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Davidson,Weiss
, p. 80 (1938)
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An efficient method for the cleavage of tert-butyldiphenylsilyl ethers catalyzed by 1,3-dibromo-5,5-dimethylhydantoin
Han, Zong
, p. 51 - 62 (2022/02/14)
An efficient method for the deprotection of tert-butyldiphenylsilyl (TBDPS) ethers using 1,3-dibromo-5,5-dimethylhydantoin (DBH) as catalyst and dimethyl sulfoxide (DMSO) as solvent has been established. This method is useful for many kinds of compounds,
Iron-catalyzed chemoselective hydride transfer reactions
Coufourier, Sébastien,Ndiaye, Daouda,Gaillard, Quentin Gaignard,Bettoni, Léo,Joly, Nicolas,Mbaye, Mbaye Diagne,Poater, Albert,Gaillard, Sylvain,Renaud, Jean-Luc
supporting information, (2021/06/07)
A Diaminocyclopentadienone iron tricarbonyl complex has been applied in chemoselective hydrogen transfer reductions. This bifunctional iron complex demonstrated a broad applicability in mild conditions in various reactions, such as reduction of aldehydes over ketones, reductive alkylation of various functionalized amines with functionalized aldehydes and reduction of α,β-unsaturated ketones into the corresponding saturated ketones. A broad range of functionalized substrates has been isolated in excellent yields with this practical procedure.
Application of bis(phosphinite) pincer nickel complexes to the catalytic hydrosilylation of aldehydes
Chang, Jiarui,Fang, Fei,Tu, Chenhao,Zhang, Jie,Ma, Nana,Chen, Xuenian
, (2020/10/27)
A series of bis(phosphinite) (POCOP) pincer ligated nickel complexes, [2,6-(tBu2PO)2C6H3]NiX (X = SH, 1; SCH2Ph, 2; SPh, 3; NCS, 4; N3, 5), were used to catalyse the hydrosilylation of aldehydes. It was found that both complexes 1 and 2 are active in catalysing the hydrosilylation of aldehydes with phenylsilane and complex 1 is comparatively more active. The expected alcohols were isolated in good to excellent yields after basic hydrolysis of the resultant hydrosilylation products. However, no reaction was observed when complex 3 or 4 or 5 was used as the catalyst. The results are consistent with complexes 1 and 2 serving as catalyst precursors, which generate the corresponding nickel hydride complex [2,6-(tBu2PO)2C6H3]NiH in situ, and the nickel hydride complex is the active species that catalyses this hydrosilylation process. The in situ generation of the nickel hydride species was supported by both experimental results and DFT calculation.
