RESORCINOL

DESCRIPTION:

Resorcinol (or resorcin) is a phenolic compound. 
Resorcinol is an organic compound with the formula C6H4(OH)2. 
Resorcinol is one of three isomeric benzenediols, the 1,3-isomer (or meta-isomer). 
Resorcinol crystallizes from benzene as colorless needles that are readily soluble in water, alcohol, and ether, but insoluble in chloroform and carbon disulfide.[6]

CAS Number    : 108-46-3 
European Community (EC) Number:  203-585-2

SYNONYMS:
Benzene-1,3-diol[1],Resorcinol[1],Resorcin,m-Dihydroxybenzene,1,3-Benzenediol,,3-Dihydroxybenzene,3-Hydroxyphenol,m-Benzenediol,resorcin,resorcinol,resorcinol disodium salt,resorcinol, monocopper (2+) salt,resorcinol,108-46-3,benzene-1,3-diol,1,3-Benzenediol,1,3-Dihydroxybenzene,Resorcin,m-Hydroquinone,m-Hydroxyphenol,m-Dihydroxybenzene,3-Hydroxyphenol,Resorcine,m-Benzenediol,m-Dioxybenzene,Dihydroxybenzol,Resorzin,Developer O,Developer R,Developer RS
,RS,Fourrine EW,Pelagol RS,Pelagol Grey RS,Resorcinolum,Fourrine 79,Nako TGG,Durafur developer G,C.I. Oxidation Base 31,Phenol, m-hydroxy-,C.I. Developer 4,Benzene, m-dihydroxy-,Rcra waste number U201,Benzene, 1,3-dihydroxy-,3-Hydroxycyclohexadien-1-one,FEMA No. 3589,Acnomel,Resorcinum,Rezamid,Sulforcin,Resorcinol (USP),NCI,C05970,NSC,1571C.I. 76505,CCRIS 4052,HSDB 722,UNII-YUL4LO94HK,YUL4LO94HK,RCRA waste no. U201,NSC-1571,EINECS 203-585-2,.alpha.-Resorcinol,Resorcin (JAN),Resorcin (TN),Resorcinol [USP],EPA Pesticide Chemical Code 071401,BRN 0906905,1,3-Dihydroxybenzol,DTXSID2021238,CHEBI:27810,AI3-03996,MFCD00002269,CHEMBL24147,DTXCID601238,C.I.-76505,EC 203-585-2,4-06-00-05658 (Beilstein Handbook Reference),Resorcinol [UN2876] [Poison],NCGC00091501-01,RESORCIN [JAN],BENZENE,1,3-DIHYDROXY RESORCINOL,RESORCINOL (IARC),RESORCINOL [IARC],RESORCINOL (MART.),RESORCINOL [MART.],RESORCINOL (USP-RS),RESORCINOL [USP-RS],RCO,Caswell No. 723,RESORCINOL (EP MONOGRAPH),RESORCINOL [EP MONOGRAPH],RESORCINOL (USP MONOGRAPH),RESORCINOL [USP MONOGRAPH],Rezorsine,m-phenylenediol,Reso,Rodol RS,CAS-108-46-3,FLUORESCEIN IMPURITY A (EP IMPURITY),FLUORESCEIN IMPURITY A [EP,IMPURITY],HEXYLRESORCINOL IMPURITY B (EP IMPURITY),HEXYLRESORCINOL IMPURITY B [EP IMPURITY],UN2876,Remazol,RS 11H,RS 11L,m-hydroxy-phenol,3-hydroxy-phenol,Resorcinol, ACS,3aqt,3-Hydroxy phenol,Resorcinol, 8CI,benzen-1,3-diol,Resorcinol, Reagent,1,3-benzene diol,Resorcine, technical,1,3-dihyroxybenzene,Acnomel (Salt/Mix),Eskamel (Salt/Mix),Rezamid (Salt/Mix),phenol derivative, 3,26982-54-7,Benzene,3-dihydroxy-,NAKO-TGG,Sulforcin (Salt/Mix),1,3-dihydroxy-benzene,Spectrum_000173,M-Dihydroxybenzene,(S),RESORCINOL [MI],Spectrum2_001310,Spectrum3_000895,Spectrum4_000990,Spectrum5_001152,RESORCINOL [FHFI],RESORCINOL [HSDB],RESORCINUM [HPUS],WLN: QR CQ,DURAFOR DEVELOPER G,RESORCINOL [VANDF],bmse000415,1,3,Dihydroxybenzene, XII,NCIOpen2_003867,RESORCINOL [WHO-DD],SCHEMBL15515,KBioGR_001399,KBioSS_000653,Resorcinol, >=98%, FG,Resorcinol, Flake, Technical,Resorcinol, LR, >=99%,BIDD:ER0285,DivK1c_000041
SPECTRUM1500527,SPBio_001379,Resorcinol, BioXtra, >=99%,BDBM26189,FEMA 3589,HMS500C03,KBio1_000041,KBio2_000653,KBio2_003221,KBio2_005789,KBio3_001810,Resorcinol, reagent grade, 98%,NSC1571,4e49,NINDS_000041,HMS1920P06,HMS2092G07,Pharmakon1600-01500527,1,3-Dihydroxybenzene (Resorcinol),Resorcinol (1,3-Dihydroxybenzene),HY-B0907,Resorcinol, ReagentPlus(R), 99%,Tox21_111140,Tox21_202417,Tox21_300140,CCG-39248,NSC757310,Resorcinol 10 microg/mL in Methanol,Resorcinol, Crystalline Powder, USP,STL185604,AKOS000119813,Resorcinol, ACS reagent, >=99.0%,Tox21_111140_1,DB11085,NSC-757310,UN 2876,IDI1_000041,NCGC00091501-02,NCGC00091501-03,NCGC00091501-04,NCGC00091501-05,NCGC00091501-06,NCGC00253918-01,NCGC00259966-01,Resorcinol, p.a., 99.0-100.5%,Resorcinol, tested according to Ph.Eur.,AC-14363,BP-21158,DA-67166,LS-13122,Resorcinol, SAJ first grade, >=98.0%,SBI-0051505.P003,1ST000085,Resorcinol, JIS special grade, >=99.0%,NS00007013,R0008,S4579,3-Hydroxycyclohexadien-1-one;3-Hydroxyphenol,EN300-19643,1,3-BENZENEDIOL; 1,3-DIHYDROXYBENZENE,C01751,D00133,AB00052085_03,A801880,Q408865,SR-05000002092,FLUORESCEIN SODIUM IMPURITY A [EP IMPURITY],Q-201666,SR,05000002092-1,BRD-K74190368-001-02-7,BRD-K74190368-001-04-3,F1908-0097,Resorcinol, certified reference material, TraceCERT(R),Z104474576,Resorcinol, European Pharmacopoeia (EP) Reference Standard,Resorcinol, United States Pharmacopeia (USP) Reference Standard,InChI=1/C6H6O2/c7-5-2-1-3-6(8)4-5/h1-4,7-8,Hymecromone impurity A, European Pharmacopoeia (EP) Reference Standard,Resorcinol, Pharmaceutical Secondary Standard; Certified Reference Material

Resorcinol is commonly used in hair dyes and acne medication. 
In higher doses it is toxic and can disrupt the function of the central nervous system and lead to respiratory problems. 
It has also been shown to disrupt the endocrine system, specifically thyroid function.

Resorcinol is primarily used by the rubber industry, especially in the production of tires; it is also used in high quality wood bonding, dyes, chemical fertilizers and in the manufacturing of certain chemicals.

Consumers are primarily exposed through cosmetic products such as hair dyes/bleaches, skin peels and treatments for a number of dermatological problems including acne and eczema.

In permanent hair dyes, resorcinol reacts with a developer (usually peroxide)to bond the dye permanently to the hairs.
 Resorcinol is usually used with other chemicals to get a specific dye color.[5] 

Typical resorcinol concentrations are about 1.25 percentalthough it can be found in concentrations up to 5 percent.
Resorcinol is used in acne and skin treatment medication to remove hard scaly or rough skin. 
The concentration in acne medicine is usually about two percent. 

When resorcinol is used as a dermatological treatment, it is likely to be applied to damaged skin, which allows more resorcinol to enter the body.[6]

Resorcinol does not occur naturally, but instead is an organic compound that is produced through a several-step process originating from the chemical compound benzene. 

Because of this lengthy process, the production of resorcinol is often very expensive, but phenolic resin producers have found additional production routes to create a supply of resorcinol. 
When any large number of resins are melted with the chemical potassium hydroxide or distilled with Brazilwood extract, resorcinol is a part of the final product such a process creates. 
Like the previously mentioned tires, resorcinol can also be found in products like dye or adhesives when combined with formaldehyde.

Resorcinol is a very white crystalline solid that becomes pink on exposure to light if not completely pure. 
Burns although ignition is difficult. 
Density approximately 1.28 g / cm3. 

Irritating to skin and eyes. 
Toxic by skin absorption. Used to make plastics and pharmaceuticals.

Resorcinol is a benzenediol that is benzene dihydroxylated at positions 1 and 3. 

Resorcinol has a role as an erythropoietin inhibitor and a sensitiser. 
Resorcinol is a benzenediol, a member of resorcinols and a phenolic donor.

Resorcinol is a 1,3-isomer (or meta-isomer) of benzenediol with the formula C6H4(OH)2. 
Resorcinol is used as an antiseptic and disinfectant in topical pharmaceutical products in the treatment of skin disorders and infections such as acne, seborrheic dermatitis, eczema, psoriasis, corns, calluses, and warts. 

Resorcinol exerts a keratolytic activity. 
Resorcinol works by helping to remove hard, scaly, or roughened skin. 

Although it is primarily indicated for use as a topical application, resorcinol also possesses a well-documented anti-thyroidal activity that is generally not relied upon for any kind of formal therapeutic indication.

PRODUCTION OF RESORCINOL
Resorcinol is produced in several steps from benzene, starting with dialkylation with propylene to give 1,3-diisopropylbenzene. 
Oxidation and Hock rearrangement of this disubstituted arene gives acetone and resorcinol.[6]

Production of resorcinol via Hock Rearrangement
Resorcinol is an expensive chemical, produced in only a very few locations around the world (as of 2010 only four commercial plants were known to be operative: in the United States, Germany, China, and Japan), and as such it is the determining factor in the cost of PRF adhesives.[7] 
Production in the United States ended in 2017 with the closure of Indspec Chemical's plant in Petrolia, Pennsylvania.[8]

Many additional routes exist for resorcinol. 
It was formerly produced by disulfonation of benzene followed by hydrolysis of the 1,3-disulfonate. 

This method has been discarded because it cogenerates so much sulfur-containing waste. 

Resorcinol can also be produced when any of a large number of resins (such as galbanum and asafoetida) are melted with potassium hydroxide, or by the distillation of Brazilwood extract. 

It may be synthesized by melting 3-iodophenol, phenol-3-sulfonic acid with potassium carbonate. 
Diazotization of 3-aminophenol or on 1,3-diaminobenzene followed by hydrolysis provides yet another route.[9] 

Many ortho- and para-compounds of the aromatic series (for example, the bromophenols, benzene-para-disulfonic acid) also yield resorcinol on fusion with potassium hydroxide.

Reactions[edit]
Partial hydrogenation of resorcinol gives dihydroresorcinol, also known as 1,3-cyclohexanedione.
It reduces Fehling's solution and ammoniacal silver solutions. 

It does not form a precipitate with lead acetate solution, as does the isomeric pyrocatechol. 

Iron(III) chloride colors its aqueous solution a dark-violet, and bromine water precipitates tribromoresorcinol. 

These properties are what give it its use as a colouring agent for certain chromatography experiments.
Sodium amalgam reduces it to dihydroresorcin, which when heated to 150 to 160 °C with concentrated barium hydroxide solution gives γ-acetylbutyric acid.

When fused with potassium hydroxide, resorcinol yields phloroglucin, pyrocatechol, and diresorcinol. 
It condenses with acids or acid chlorides, in the presence of dehydrating agents, to oxyketones, for example, with zinc chloride and glacial acetic acid at 145 °C it yields resacetophenone (HO)2C6H3COCH3.[12] 

With the anhydrides of dibasic acids, it yields fluoresceins. 
When heated with calcium chloride—ammonia to 200 °C it yields meta-dioxydiphenylamine.[13]

With sodium nitrite it forms a water-soluble blue dye, which is turned red by acids, and is used as a pH indicator under the name of lacmoid.[14] 
It condenses readily with aldehydes, yielding with formaldehyde, on the addition of catalytic hydrochloric acid, methylene diresorcin [(HO)C6H3(O)]2CH2. 

Reaction with chloral hydrate in the presence of potassium bisulfate yields the lactone of tetra-oxydiphenyl methane carboxylic acid.[15] 
In alcoholic solution it condenses with sodium acetoacetate to form 4-methylumbelliferone.[16]

In presence of Sulfuric acid, with twice amount of Succinic acid, Resorcinol creates Fluorescence effect on water.[17]
In addition to electrophilic aromatic addition, resorcinol (and other polyols) undergo nucleophilic substitution via the enone tautomer.

Nitration with concentrated nitric acid in the presence of cold concentrated sulfuric acid yields trinitroresorcin (styphnic acid), an explosive.

Occurrence and use
Derivatives of resorcinol are found in different natural sources. 
Alkylresorcinols are found in rye.[18] Polyresorcinols are found as pseudotannins in plants.[17]

Adhesives
Resorcinol is mainly used in the production of resins. 
As a mixture with phenol, it condenses with formaldehyde to afford adhesives. 

Such resins are used as adhesives in the rubber industry and others are used for wood glue.[6] 
In relation to its conversion resins with formaldehyde, resorcinol is the starting material for resorcinarene rings.

Medical uses
It is present in over-the-counter topical acne treatments at 2% or less concentration, and in prescription treatments at higher concentrations.[19] 
Monoacetylresorcinol, C6H4(OH)(O–COCH3), is used under the name of Euresol.[20] 

It is used in hidradenitis suppurativa with limited evidence showing it can help with resolution of the lesions.[21] 
Resorcinol is one of the active ingredients in products such as Resinol, Vagisil, and Clearasil.

In the 1950s and early 1960s the British Army used it, in the form of a paste applied directly to the skin. 
One such place where this treatment was given to soldiers with chronic acne was the Cambridge Military Hospital, Aldershot, England. It was not always successful.
4-Hexylresorcinol is an anesthetic found in throat lozenges.

Chemical uses
Resorcinol is used as a chemical intermediate for the synthesis of pharmaceuticals and other organic compounds. 
Resorcinol is used in the production of diazo dyes and plasticizers and as a UV absorber in resins.

Resorcinol is an analytical reagent for the qualitative determination of ketoses (Seliwanoff's test).
Resorcinol is the starting material for the initiating explosive lead styphnate.[22]

Related compounds[edit]
Resazurin, C12H7NO4, obtained by the action of nitrous acid on resorcinol,[23] forms small dark red crystals possessing a greenish metallic glance. 
When dissolved in concentrated sulfuric acid and warmed to 210 °C, the solution on pouring into water yields a precipitate of resorufin, C12H7NO3, an oxyphenoxazone, which is insoluble in water but is readily soluble in hot concentrated hydrochloric acid, and in solutions of caustic alkalis. 

The alkaline solutions are of a rose-red color and show a cinnabar-red fluorescence. 
A tetrabromresorufin is used as a dyestuff under the name of Fluorescent Resorcin Blue.

Thioresorcinol is obtained by the action of zinc and hydrochloric acid on meta-benzenedisulfonyl chloride. It melts at 27 °C and boils at 243 °C. 

Resorcinol disulfonic acid, (HO)2C6H2(HSO3)2, is a deliquescent mass obtained by the action of sulfuric acid on resorcin.[24] 
It is readily soluble in water and ethanol.

Resorcinol is also a common scaffold that is found in a class of anticancer agents, some of which (luminespib, ganetespib, KW-2478, and onalespib) were in clinical trials as of 2014.[25][26] 

Part of the resorcinol structure binds to inhibits the N-terminal domain of heat shock protein 90, which is a drug target for anticancer treatments.[25]

History, etymology, and nomenclature
Austrian chemist Heinrich Hlasiwetz (1825–1875) is remembered for his chemical analysis of resorcinol and for his part in the first preparation of resorcinol, along with Ludwig Barth, which was published in 1864.[27]: 10 [28]

Benzene-1,3-diol is the name recommended by the International Union of Pure and Applied Chemistry (IUPAC) in its 1993 Recommendations for the Nomenclature of Organic Chemistry.[29]

Resorcinol is so named because of its derivation from ammoniated resin gum, and for its relation to the chemical orcinol.

PROPERTIES OF RESORCINOL
Chemical formula    C6H6O2
Molar mass    110.111 g/mol
Appearance    White solid[2]
Odor    Faint[2]
Density    1.28 g/cm3, solid
Melting point    110 °C (230 °F; 383 K)
Boiling point    277 °C (531 °F; 550 K)
Solubility in water    110 g/100 mL at 20 °C
Vapor pressure    0.0002 mmHg (25 °C)[2]
Acidity (pKa)    9.15[3]
Magnetic susceptibility (χ)    −67.26×10−6 cm3/mol
Refractive index (nD)    1.578[4]
Dipole moment    2.07±0.02 D[5]
Thermochemistry
Std enthalpy of
formation (ΔfH⦵298)    -368.0 kJ•mol−1[4]
Enthalpy of fusion (ΔfH⦵fus)    20.4 kJ•mol−1[4]
Molecular Weight
110.11 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
XLogP3
0.8
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Hydrogen Bond Donor Count
2
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Hydrogen Bond Acceptor Count
2
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Rotatable Bond Count
0
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Exact Mass
110.036779430 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Monoisotopic Mass
110.036779430 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Topological Polar Surface Area
40.5Ų
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Heavy Atom Count
8
Computed by PubChem
Formal Charge
0
Computed by PubChem
Complexity
64.9
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Isotope Atom Count
0
Computed by PubChem
Defined Atom Stereocenter Count
0
Computed by PubChem
Undefined Atom Stereocenter Count
0
Computed by PubChem
Defined Bond Stereocenter Count
0
Computed by PubChem
Undefined Bond Stereocenter Count
0
Computed by PubChem
Covalently-Bonded Unit Count
1
Computed by PubChem
Compound Is Canonicalized
Yes

SAFETY INFORMATION ABOUT RESORCINOL
First aid measures:
Description of first aid measures:
General advice:
Consult a physician. 
Show this safety data sheet to the doctor in attendance.
Move out of dangerous area:
 
If inhaled:
If breathed in, move person into fresh air. 
If not breathing, give artificial respiration.
Consult a physician.
In case of skin contact:
Take off contaminated clothing and shoes immediately. 
Wash off with soap and plenty of water.
Consult a physician.
 
In case of eye contact:
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
Continue rinsing eyes during transport to hospital.
 
If swallowed:
Do NOT induce vomiting. 
Never give anything by mouth to an unconscious person. 
Rinse mouth with water. 
Consult a physician.
 
Firefighting measures:
Extinguishing media:
Suitable extinguishing media:
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas
 
Advice for firefighters:
Wear self-contained breathing apparatus for firefighting if necessary.
Accidental release measures:
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. 
 
Avoid breathing vapours, mist or gas. 
Evacuate personnel to safe areas.
 
Environmental precautions:
Prevent further leakage or spillage if safe to do so.
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Methods and materials for containment and cleaning up:
Soak up with inert absorbent material and dispose of as hazardous waste. 
Keep in suitable, closed containers for disposal.
 
Handling and storage:
Precautions for safe handling:
Avoid inhalation of vapour or mist.
 
Conditions for safe storage, including any incompatibilities:
Keep container tightly closed in a dry and well-ventilated place. 
Containers which are opened must be carefully resealed and kept upright to prevent leakage.
Storage class (TRGS 510): 8A: Combustible, corrosive hazardous materials
 
Exposure controls/personal protection:
Control parameters:
Components with workplace control parameters
Contains no substances with occupational exposure limit values.
Exposure controls:
Appropriate engineering controls:
Handle in accordance with good industrial hygiene and safety practice.
Wash hands before breaks and at the end of workday.
 
Personal protective equipment:
Eye/face protection:
Tightly fitting safety goggles. 
Faceshield (8-inch minimum). 
Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
 
Skin protection:
Handle with gloves. 
Gloves must be inspected prior to use. 
Use proper glove
removal technique (without touching glove's outer surface) to avoid skin contact with this product. 
Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. 
Wash and dry hands.
 
Full contact:
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0.11 mm
Break through time: 480 min
Material tested:Dermatril (KCL 740 / Aldrich Z677272, Size M)
It should not be construed as offering an approval for any specific use scenario.
 
Body Protection:
Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection:
Where risk assessment shows air-purifying respirators are appropriate use a fullface respirator with multi-purpose combination (US) or type ABEK (EN 14387) respirator cartridges as a backup to engineering controls. 
 
If the respirator is the sole means of protection, use a full-face supplied air respirator. 
Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Prevent further leakage or spillage if safe to do so. 
Do not let product enter drains.
Discharge into the environment must be avoided.
 
Stability and reactivity:
Chemical stability:
Stable under recommended storage conditions.
Incompatible materials:
Strong oxidizing agents:
Hazardous decomposition products:
Hazardous decomposition products formed under fire conditions. 
Carbon oxides, Nitrogen oxides (NOx), Hydrogen chloride gas.
 
Disposal considerations:
Waste treatment methods:
Product:
Offer surplus and non-recyclable solutions to a licensed disposal company. 
Contact a licensed professional waste disposal service to dispose of this material.
Contaminated packaging:
Dispose of as unused product