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,
A Bifunctional Copper Catalyst Enables Ester Reduction with H2: Expanding the Reactivity Space of Nucleophilic Copper Hydrides
Kaicharla, Trinadh,Ngoc, Trung Tran,Teichert, Johannes F.,Tzaras, Dimitrios-Ioannis,Zimmermann, Birte M.
supporting information, p. 16865 - 16873 (2021/10/20)
Employing a bifunctional catalyst based on a copper(I)/NHC complex and a guanidine organocatalyst, catalytic ester reductions to alcohols with H2 as terminal reducing agent are facilitated. The approach taken here enables the simultaneous activation of esters through hydrogen bonding and formation of nucleophilic copper(I) hydrides from H2, resulting in a catalytic hydride transfer to esters. The reduction step is further facilitated by a proton shuttle mediated by the guanidinium subunit. This bifunctional approach to ester reductions for the first time shifts the reactivity of generally considered "soft"copper(I) hydrides to previously unreactive "hard"ester electrophiles and paves the way for a replacement of stoichiometric reducing agents by a catalyst and H2.
Hydroboration of aldehydes, ketones and CO2under mild conditions mediated by iron(iii) salen complexes
James, Alexander P.,Lau, Samantha,Provis-Evans, Cei B.,Webster, Ruth L.
supporting information, p. 10696 - 10700 (2021/08/17)
The hydroboration of aldehydes, ketones and CO2is demonstrated using a cheap and air stable [Fe(salen)]2-μ-oxo pre-catalyst with pinacolborane (HBpin) as the reductant under mild conditions. This catalyst system chemoselectively hydroborates aldehydes over ketones and ketones over alkenes. In addition, the [Fe(salen)2]-μ-oxo pre-catalyst shows good efficacy at reducing “wet” CO2with HBpin at room temperature.
