873-76-7 Usage
Description
4-Chlorobenzyl alcohol is a white crystalline powder that serves as an intermediate in organic synthesis and the pharmaceutical industry. It is known for its ability to react with o-xylene in the presence of HAuCl4 or AuCl3 at 80°C to generate the corresponding benzylated product. Additionally, it can undergo acetylation in the presence of catalytic amounts of Ce(OTf)4 in acetic acid to produce the desired esters with excellent yields. Furthermore, it can be used as a raw material to produce its corresponding carboxylic acids and ketones through oxidation reactions using hydrogen peroxide and cobalt(II) complex. It can also undergo formylation and acetylation in the presence of Silphos [PCl3?n(SiO2)n] in ethyl formate and ethyl acetate.
Uses
Used in Organic Synthesis:
4-Chlorobenzyl alcohol is used as a reagent for the protection of carboxyl groups as their 4-chlorobenzyl esters, which are more stable to acid than the corresponding benzyl esters.
Used in Paint and Coating Industry:
4-Chlorobenzyl alcohol is used as a solvent in paint stripper and waterborne coatings, contributing to their effectiveness and performance.
Used as a Curing Agent:
In certain applications, 4-Chlorobenzyl alcohol acts as a curing agent, facilitating the hardening and setting of materials.
Used in Pharmaceuticals:
4-Chlorobenzyl alcohol is utilized in the pharmaceutical industry, potentially for the development of new drugs or as a component in existing medications.
Used in Cosmetics:
It is also used in cosmetics, likely for its properties that can enhance the formulation or effectiveness of beauty products.
Used in Preservatives:
4-Chlorobenzyl alcohol may be employed as a preservative, helping to maintain the shelf life and stability of various products.
Used in Flavoring & Fragrance Industry:
It is used in the flavoring and fragrance industry, possibly for its ability to contribute to the scent or taste profiles of different products.
Referrence
Mertins, K.; Lovel, I.; Kischel, J.; Zapf, A.; Beller, M., Gold-catallyzed benzylation of arenes and heteroarenes. Adv. Synth. Catal. 2006, 348, 691-695.
Iranpoor, N.; Shekarriz, M., Catalytic Esterification of Alcohols, Carboxylic Acids and Transesterification Reactions with Cerium(IV) Triflate. Bull. Chem. Soc. Jpn. 1999, 72, 455-458.
Das, S.; Punniyamurthy, T., Cobalt(II)-catalyzed oxidation of alcohols into carboxylic acids and ketones with hydrogen peroxide. Tetrahedron Lett. 2003, 44, 6033-6035.
Iranpoor, N.; Firouzabadi, H.; Jamalian, A., Silphos PCl3-n(SiO2)(n) : a heterogeneous phosphine reagent for formylation and acetylation of alcohols and amines with ethyl formate and acetate. Tetrahedron Lett. 2005, 46, 7963-7966.
Check Digit Verification of cas no
The CAS Registry Mumber 873-76-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 8,7 and 3 respectively; the second part has 2 digits, 7 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 873-76:
(5*8)+(4*7)+(3*3)+(2*7)+(1*6)=97
97 % 10 = 7
So 873-76-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H7ClO/c8-7-3-1-6(5-9)2-4-7/h1-4,9H,5H2
873-76-7Relevant articles and documents
Hydrogenation of Esters by Manganese Catalysts
Li, Fu,Li, Xiao-Gen,Xiao, Li-Jun,Xie, Jian-Hua,Xu, Yue,Zhou, Qi-Lin
, (2022/01/13)
The hydrogenation of esters catalyzed by a manganese complex of phosphine-aminopyridine ligand was developed. Using this protocol, a variety of (hetero)aromatic and aliphatic carboxylates including biomass-derived esters and lactones were hydrogenated to primary alcohols with 63–98% yields. The manganese catalyst was found to be active for the hydrogenation of methyl benzoate, providing benzyl alcohol with turnover numbers (TON) as high as 45,000. Investigation of catalyst intermediates indicated that the amido manganese complex was the active catalyst species for the reaction. (Figure presented.).
A mild and selective Cu(II) salts-catalyzed reduction of nitro, azo, azoxy, N-aryl hydroxylamine, nitroso, acid halide, ester, and azide compounds using hydrogen surrogacy of sodium borohydride
Kalola, Anirudhdha G.,Prasad, Pratibha,Mokariya, Jaydeep A.,Patel, Manish P.
supporting information, p. 3565 - 3589 (2021/10/12)
The first mild, in situ, single-pot, high-yielding well-screened copper (II) salt-based catalyst system utilizing the hydrogen surrogacy of sodium borohydride for selective hydrogenation of a broad range of nitro substrates into the corresponding amine under habitancy of water or methanol like green solvents have been described. Moreover, this catalytic system can also activate various functional groups for hydride reduction within prompted time, with low catalyst-loading, without any requirement of high pressure or molecular hydrogen supply. Notably, this system explores a great potential to substitute expensive traditional hydrogenation methodologies and thus offers a greener and simple hydrogenative strategy in the field of organic synthesis.
Redox-active ligand based Mn(i)-catalyst for hydrosilylative ester reduction
Chakraborty, Soumi,Das, Arpan,Mandal, Swadhin K.
supporting information, p. 12671 - 12674 (2021/12/04)
Herein a Mn(i) catalyst bearing a redox-active phenalenyl (PLY) based ligand is reported for the efficient hydrosilylation of esters to alcohols using the inexpensive silane source polymethylhydrosiloxane (PMHS) under mild conditions. Mechanistic investigations suggest a strong ligand-metal cooperation where a ligand-based single electron transfer (SET) process initiates the reaction through Si-H bond activation.