Resorcinol

Base Information

• Chemical Name: Resorcinol
• CAS No.: 108-46-3
• Molecular Formula: C6H6O2
• Molecular Weight: 110.112
• Hs Code.: 2907 21 00
• European Community (EC) Number: 203-585-2
• ICSC Number: 1033
• NSC Number: 757310,1571
• UN Number: 2876
• UNII: YUL4LO94HK
• DSSTox Substance ID: DTXSID2021238
• Nikkaji Number: J2.863K
• Wikipedia: Resorcinol
• Wikidata: Q408865
• NCI Thesaurus Code: C77056
• RXCUI: 35382
• Metabolomics Workbench ID: 45222
• ChEMBL ID: CHEMBL24147
• Mol file: 108-46-3.mol

Synonyms:resorcin;resorcinol;resorcinol disodium salt;resorcinol, monocopper (2+) salt

Chemical Property of Resorcinol

Chemical Property:

• Appearance/Colour: crystals or powder
• Vapor Pressure: 1 mm Hg ( 21.1 °C)
• Melting Point: 109-112 °C(lit.)
• Refractive Index: 1.612
• Boiling Point: 279.999 °C at 760 mmHg
• PKA: 9.81(at 25℃)
• Flash Point: 131.928 °C
• PSA: 40.46000
• Density: 1.27 g/cm³
• LogP: 1.09780
• Storage Temp.: 0-6°C
• Sensitive.: Light Sensitive
• Solubility.: H2O: soluble1M at 20°C, clear, faintly yellow
• Water Solubility.: 140 g/100 mL
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 110.036779430
• Heavy Atom Count: 8
• Complexity: 64.9
• Transport DOT Label: Poison

Purity/Quality:

99%MIN, ^*data from raw suppliers

Resorcinol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,N
• Hazard Codes: Xn,N
• Statements: 22-36/38-50-50/53-41-38
• Safety Statements: 26-61-39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Phenols
• Canonical SMILES: C1=CC(=CC(=C1)O)O
• Recent ClinicalTrials: Effectiveness of Three Dimensional Correction During in Bracing in Adolescent Idiopathic Scoliosis
• Inhalation Risk: A harmful contamination of the air will not or will only very slowly be reached on evaporation of this substance at 20 °C; on spraying or dispersing, however, much faster.
• Effects of Short Term Exposure: The substance is irritating to the eyes, skin and respiratory tract. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization in rare cases.
• Uses: Manufacture of rubber products, wood adhesives, dyes, explosives, and cosmetics; in photography. 1. It can be used as the raw materials for the production of synthetic resins, adhesives, dyes and ultraviolet absorbing agent. It can also be used as the dipped cord of tire. Medically it can be used as the disinfection antiseptic agent. 2. Resorcinol is also known as 1, 3-hydroquinone. In the field of pesticides, it can be used as the intermediate 3-chloro-4-methyl coumarin and herbicide oxyfluorfen in the synthesis of pesticides coumaphos. It can also be used for the production of dyes, specialty coatings, pharmaceuticals, photographic material, synthetic resins, adhesives, and cosmetics. 3. Resorcinol is mainly used for the field of rubber adhesives, synthetic resins, dyes, preservative, pharmaceutical and analytical reagents. Resorcinol is similar with phenol and cresol. It can generate condensation polymer through the reaction with formaldehyde. It can be used for making glue silk and the adhesive agent of tire cord for nylon-purpose, making wood glue, and being as the adhesive for vinyl material and metal. Resorcinol is the intermediate of many kinds of azo dyes and fur dyes as well as the raw material of pharmaceutical intermediates, p-nitrogen salicylic acid. Resorcinol has bactericidal effects and can be used as preservatives for being supplied to cosmetics and dermatological drugs pastes and ointments. The resorcinol derivatives, β-methylumbelliferone can be used as the intermediate for optical bleach; tri-nitro resorcinol is detonator. There is also a considerable amount of resorcinol being used in the production of benzophenone-class ultraviolet absorbers. This product can irritate the skin and mucous membranes, can cause poisoning disease through the rapid absorption by the skin. Minimum lethal dose of rat being subject to subcutaneous injection is 450mg/kg. 4. It can be applied to the fields of photographic film, medicines, dyes and chemical fiber industry. 5. It can also be used as reagents for analysis. 6. It can be used for characterization and determination of zinc, lead, tartaric acid, nitrate and nitrite through colorimetric method; it can also applied to the colorimetric reaction for measuring sugar and Furfuryl alcohol; as the reagent for detecting ketone sugars and lignin; it can also applied to the salt reagent of diazonium compound as well as to organic synthesis. Resorcinol is used in the manufacture of resorcinol–formaldehyde resins, resin adhesives, dyes, drugs, andexplosives; in tanning; in cosmetics; and in dyeing and printing textiles. In very mild solutions, resorcinol is used as an anti-septic and soothing preparation for itchy skin. In slightly higher concentrations, resorcinol removes the top layer of the stratum corneum and is used particularly in cases of acne. In still higher concentrations, it can act as an aggressive surface skin exfoliant. Resorcinol can also be used as a preservative. While it is a beneficial skin care ingredient when used in low concentrations, it causes irritation in higher concentrations with a strong burning sensation and a reddening of the skin. used in high concentrations as a peel, resorcinol may cause a variety of problems, including swelling. It is is obtained from various resins. A benzene derivative used as keratolytic and antiseborrheic. Also used in veterinary medicine as a topical antipruritic and antiseptic (has been used as intestinal antiseptic). anthelmintic An aromatic alcohol used as a chemical intermediate
• description: Resorcinol has bactericidal, fungicidal and anti-itching effect with the bactericidal effect being 1/3 of the phenol and also a low irritating and corrosive property. At low concentration, it can play the role promoting the regeneration of horny while having keratin exfoliation effect at high concentration. It is mainly used for rubber adhesives, plastics, synthetic resins, synthetic fibers, dyes, preservatives, anti-itch, anti-fungal agent, analytical reagent and can also be used to treat ringworm, eczema, seborrheic dermatitis, acne and psoriasis. Figure 1 3D structure of resorcinol. The above information is edited by the lookchem of Dai Xiongfeng.
• Indications: It can be used for the treatment of seborrheic dermatitis, acne, superficial skin fungal infections, tinea versicolor, calluses, corns, and common warts. Resorcinol (resorcin), a phenol derivative, is less keratolytic than salicylic acid. This drug is an irritant and sensitizer and reported to be both bactericidal and fungicidal. Solutions containing 1% to 2% have been used in preparations for seborrhea, acne, and psoriasis.

Technology Process of Resorcinol

There total 313 articles about Resorcinol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 56.0%

1,3-diisopropylbenzene (99-62-7) → 3-isopropylhydroxybenzene (618-45-1) + recorcinol (108-46-3)

Guidance literature:

1,3-diisopropylbenzene; With N-hydroxyphthalimide; 2,2'-azobis(isobutyronitrile); oxygen; In acetonitrile; at 75 ℃; for 20h; under 760.051 Torr;

With sulfuric acid; In acetonitrile; at 75 ℃; for 4h; Further stages.;

DOI:10.1002/1615-4169(20011231)343:8<809::AID-ADSC809>3.0.CO;2-1

Reference yield: 48.9%

3,5-dihydroxyphenol (108-73-6) → 1,3-cylohexanedione (504-02-9) + recorcinol (108-46-3)

Guidance literature:

With potassium hydroxide; Raney Ni-Al alloy; In water; at 90 ℃; for 6h;

DOI:10.3184/030823409X465394

Reference yield: 38.0%

3-(4-Hydroxy-phenyl)-1-(2,4,6-trihydroxy-phenyl)-propan-1-on (60-82-2) → 3-(4-hydroxyphenyl)propan-1-ol (10210-17-0) + 4-hydroxyphenylpropionic acid (501-97-3) + recorcinol (108-46-3)

Guidance literature:

With sodium hydroxide; sodium tetrahydroborate; In water; at 100 ℃; Product distribution;

upstream raw materials:

7-hydroxy-2H-chromen-2-one

3,5-dihydroxyphenol

3-monochlorophenol

4-bromo-phenol

Downstream raw materials:

benzoate d'hydroxy-3 phenyle

resorcinol dibenzoate

resorcin bis(tetrahydropyranyl)ether

β-(2,4-dihydroxybenzoyl)acrylic acid

Refernces

• 1、 Jassoy. "-". . p. 544. Retrieved 1890.
• 2、 Sheng, Xiang,Patskovsky, Yury,Vladimirova, Anna,Bonanno, Jeffrey B.,Almo, Steven C.,Himo, Fahmi,Raushel, Frank M.. "Mechanism and Structure of γ-Resorcylate Decarboxylase". . p. 3167 - 3175. Retrieved 2018.
• 3、 Fittig,Mager. "-". . p. 364. Retrieved 1875.
• 4、 Fray. "-". . p. 316. Retrieved 1958.
• 5、 Nagai,Nagumo,Lee,et al.. "Protosappanin A, a novel biphenyl compound from sappan lignum". . p. 1 - 6. Retrieved 1986.
• 6、 Sang, Dayong,Wang, Jiahui,Zheng, Yun,He, Jianyuan,Yuan, Caili,An, Qing,Tian, Juan. "Carbodiimides as Acid Scavengers in Aluminum Triiodide Induced Cleavage of Alkyl Aryl Ethers". . p. 2721 - 2726. Retrieved 2017.
• 7、 Matsuura,Omura. "-". . p. 173,182. Retrieved 1974.
• 8、 Valdés, Cristian,Alzate-Morales, Jans,Osorio, Edison,Villase?or, Jorge,Navarro-Retamal, Carlos. "A characterization of the two-step reaction mechanism of phenol decomposition by a Fenton reaction". . p. 16 - 22. Retrieved 2015.
• 9、 Feng, Shao-Hong,Zhang, Shu-Juan,Yu, Han-Qing,Li, Qian-Rong. "Radiation-induced Degradation of Nitrobenzene in Aqueous Solutions". . p. 718 - 719. Retrieved 2003.
• 10、 Brede, Ortwin,Kapoor, Sudhir,Mukherjee, Tulsi,Hermann, Ralf,Naumov, Sergej. "Diphenol radical cations and semiquinone radicals as direct products of the free electron transfer from catechol, resorcinol and hydroquinone to parent solvent radical cations". . p. 5096 - 5104. Retrieved 2002.