102-40-9

Basic information

• Product Name: m-Bis(2-hydroxyethoxy)benzene
• Synonyms: 1,3-DI(2-HYDROXYETHOXY)BENZENE;1,3-BIS(2-HYDROXYETHOXY)BENZENE;RESORCINOL BIS-(2-HYDROXYETHYL)ETHER;RESORCINOL BIS(BETA-HYDROXYETHYL) ETHER;RESORCINOL DIHYDROXYETHYL ETHER;2,2’-[1,3-phenylenebis(oxy)]bis-ethano;2,2'-[1,3-phenylenebis(oxy)]bisethanol;O,O'-Bis(2'-hydroxyethyl) resorcinol
• CAS NO: 102-40-9
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.22
• EINECS: 203-028-3
• Product Categories: Aromatic Ethers
• Mol File: 102-40-9.mol
• Article Data: 8

Chemical Properties

• Melting Point: 90 °C
• Boiling Point: 234 °C / 30mmHg
• Flash Point: 182.378 °C
• Appearance: /
• Density: 1.198 g/cm³
• Vapor Pressure: 2.19E-06mmHg at 25°C
• Refractive Index: 1.54
• Solubility: Slightly soluble in water
• PKA: 13.95±0.10(Predicted)
• Water Solubility: 18g/L at 20℃
• CAS DataBase Reference: m-Bis(2-hydroxyethoxy)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: m-Bis(2-hydroxyethoxy)benzene(102-40-9)
• EPA Substance Registry System: m-Bis(2-hydroxyethoxy)benzene(102-40-9)

Safety Data

• Hazardous Substances Data: 102-40-9(Hazardous Substances Data)

Usage

General Description

m-Bis(2-hydroxyethoxy)benzene, also known as 1,3-Bis(2-hydroxyethoxy)benzene or simply Bisphenol C, is a chemical compound. It is primarily used as a chemical intermediate in the synthesis of various polymers and resins, such as epoxy resins and polyester resins. It can impart flexibility, strength, and durability to these materials, making them suitable for a wide range of applications, including coatings, adhesives, and composite materials.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C10H14O4/c11-4-6-13-9-2-1-3-10(8-9)14-7-5-12/h1-3,8,11-12H,4-7H2

Synthetic route

ethylene glycol (107-21-1) + recorcinol (108-46-3) → 1,3-bis(2-hydroxyethoxy)benzene (102-40-9)

Conditions	Yield
With sodium carbonate; urea; zinc(II) oxide at 170 - 190℃;	99%

diethyl 2,2′‐(1,3‐phenylenebis(oxy))diacetate (66644-04-0) → 1,3-bis(2-hydroxyethoxy)benzene (102-40-9)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 3h; Heating;	81%

2-chloro-ethanol (107-07-3) + recorcinol (108-46-3) → 1,3-bis(2-hydroxyethoxy)benzene (102-40-9)

Conditions	Yield
With sodium hydroxide In ethanol; water for 72h; Heating;	69%
With potassium hydroxide at 100℃;
With sodium ethanolate

recorcinol (108-46-3) + biphenyldiol-(2.4') → 1,3-bis(2-hydroxyethoxy)benzene (102-40-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 47 percent / KOH / ethanol / 72 h / Heating 2: 81 percent / LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + 2,4-bis(3,5-di-tert-butyl-4-hydroxyphenyl)-1,3,2,4-dithiadiphosphetane-2,4-disulfide (58851-58-4) → O,O'-benzene-1,3-bis[ethoxy-2-(3,5-di-tert-butyl-4-hydroxyphenyldithiophosphonic acid)] (1379612-23-3)

Conditions	Yield
In benzene at 20℃; Inert atmosphere;	91%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + 2,4-(4-phenoxyphenyl)-1,3-dithia-2λ(5),4λ(5)-diphosphetane 2,4-disulfides (92825-37-1, 88816-02-8) → O,O'-benzene-1,3-bis[ethoxy-2-(4-phenoxyphenyldithiophosphonic acid)] (1379612-26-6)

Conditions	Yield
In benzene at 20℃; for 2h; Inert atmosphere;	91%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 1,3-bis(2-bromoethoxy)benzene (58929-74-1)

Conditions	Yield
With bromine; triphenylphosphine In acetonitrile at 20℃;	83.7%
With bromine; triphenylphosphine In acetonitrile 1.) 5 deg C up to RT; 2.) RT, 4 h;	66%
With phosphorus tribromide

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + Phenyl glycidyl ether (122-60-1) → C28H34O8

Conditions	Yield
With potassium tert-butylate In tetrahydrofuran at 70℃;	82%

pyrrol-2-yl trichloromethyl ketone (35302-72-8) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 1,3-bis[2-(pyrrol-2-carbonyloxy)ethoxy]benzene (1282042-48-1)

Conditions	Yield
With triethylamine In acetonitrile for 20h; Reflux;	63%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + p-toluenesulfonyl chloride (98-59-9) → 1,3-bis(2-tosyloxyethoxy)benzene (136028-18-7)

Conditions	Yield
With triethylamine In dichloromethane for 96h; Ambient temperature;	60%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + p-toluenesulfonyl chloride (98-59-9) → 2-(3-(2-hydroxyethoxy)phenoxy)ethyl 4-methylbenzenesulfonate

Conditions	Yield
With pyridine at 0℃; for 2h;	56%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + hexanal (66-25-1) → 4,6,10,12,16,18,22,24-octakis(2-hydroxyethoxy)-2,8,14,20-tetrapentylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene

Conditions	Yield
With hydrogenchloride In ethanol at 90℃;	55%
With hydrogenchloride In ethanol; water at 90℃; for 48h;

tridecanal (10486-19-8) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 2,2',2'',2''',2'''',2''''',2'''''',2'''''''-(((2R,4S)-2,4,6,8-tetradodecyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-14,16,34,36,54,56,74,76-octayl)octakis(oxy))octakis(ethan-1-ol)

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 90℃; for 48.25h;	47%

Dodecanal (112-54-9) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 2,2',2'',2''',2'''',2''''',2'''''',2'''''''-(((2R,4S)-2,4,6,8-tetraundecyl-1,3,5,7(1,3)-tetrabenzencyclooctaphane-14,16,34,36,54,56,74,76-octayl)octakis(oxy))octakis(ethan-1-ol)

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 90℃; for 48.25h;	46%

caprinaldehyde (112-31-2) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 2,2',2'',2''',2'''',2''''',2'''''',2'''''''-(((2R,4S)-2,4,6,8-tetranonyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-14,16,34,36,54,56,74,76-octayl)octakis(oxy))octakis(ethan-1-ol) (1227741-79-8)

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 90℃; for 48.25h;	44%
With hydrogenchloride In ethanol; water at 90℃; for 48h;

undecylaldehyde (112-44-7) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 2,2',2'',2''',2'''',2''''',2'''''',2'''''''-(((2R,4S)-2,4,6,8-tetrakis(decyl)-1,3,5,7(1,3)-tetrabenzeacyclooctaphane-14,16,34,36,54,56,74,76-octayl)octakis(oxy))octakis(ethan-1-ol)

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 90℃; for 48.25h;	44%

nonan-1-al (124-19-6) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 2,2',2'',2''',2'''',2''''',2'''''',2'''''''-(((2R,4S)-2,4,6,8-tetraoctyl-1,3,5,7(1,3)-tetrabenzenacyclooctaphane-14,16,34,36,54,56,74,76-octayl)octakis(oxy))octakis(ethan-1-ol) (374563-16-3)

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 90℃; for 48.25h;	42%
With hydrogenchloride In ethanol; water at 90℃; for 48h;

Octanal (124-13-0) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 4,6,10,12,16,18,22,24-octakis(2-hydroxyethoxy)-2,8,14,20-tetraheptylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene

Conditions	Yield
With hydrogenchloride In ethanol at 0 - 90℃; for 48.25h;	40%
With hydrogenchloride In ethanol at 90℃;	25%
With hydrogenchloride In ethanol; water at 90℃; for 48h;

Octanal (124-13-0) + 1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → C74H116O16

Conditions	Yield
With hydrogenchloride In ethanol; water at 0 - 90℃; for 48h;	40%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + propionaldehyde (123-38-6) → 4,6,10,12,16,18,22,24-octakis(2-hydroxyethoxy)-2,8,14,20-tetraethylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene

Conditions	Yield
With hydrogenchloride In ethanol at 90℃; for 48h;	37%
With hydrogenchloride In ethanol; water at 90℃; for 48h;

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + isobutyraldehyde (78-84-2) → 4,6,10,12,16,18,22,24-octakis(2-hydroxyethoxy)-2,8,14,20-tetraisopropylpentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(25),3,5,7(28),9,11,13(27),15,17,19(26),21,23-dodecaene

Conditions	Yield
With hydrogenchloride In ethanol at 90℃;	20%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + 4-bromo-benzaldehyde (1122-91-4) → 3,5,10,12,17,19,25,26-octakis(β-hydroxyethoxy)-1,8,15,22-tetrakis(p-bromophenyl)<14>metacyclophane

Conditions	Yield
With hydrogenchloride In ethanol; water for 2.5h; Heating;	7%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + benzaldehyde (100-52-7) → 3,5,10,12,17,19,25,26-octakis(β-hydroxyethoxy)-1,8,15,22-tetraphenyl<14>metacyclophane

Conditions	Yield
With hydrogenchloride In ethanol; water for 2.5h; Heating;	5%

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 2,3,5,6-tetrahydrobenzo[1,2-b;5,4-b']difuran (57052-75-2)

Conditions	Yield
With phosphorus pentaoxide; 2,4-dimethylpentan-3-one

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 1,3-bis-(2-chloro-ethoxy)-benzene (63807-84-1)

Conditions	Yield
With phosphorus pentachloride at 100℃;

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 1,3-bis-(2-acetoxy-ethoxy)-benzene (133633-37-1)

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 1,3-bis-(2-benzoyloxy-ethoxy)-benzene

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + trityl chloride (76-83-5) → 1,3-bis-(2-trityloxy-ethoxy)-benzene

Conditions	Yield
With pyridine

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) + acetylene (74-86-2) → 1,3-bis-(2-vinyloxy-ethoxy)-benzene (84040-78-8)

1,3-bis(2-hydroxyethoxy)benzene (102-40-9) → 1,3-Bis(2'-hydroxyethoxy)benzene-2-d

Conditions	Yield
With sulfuric acid-d2 In acetonitrile for 1h; Quantum yield; Irradiation; different medium acidity; photoprotonation rate constant;
With sulfuric acid-d2 In acetonitrile at 15℃; Quantum yield; Irradiation; var. pD;
With sulfuric acid-d2 In acetonitrile for 1h;

Upstream product

• 107-21-1 ethylene glycol 
• 108-46-3 recorcinol 
• 66644-04-0 diethyl 2,2′‐(1,3‐phenylenebis(oxy))diacetate 
• 107-07-3 2-chloro-ethanol 

Downstream Products

• 136028-18-7 1,3-bis(2-tosyloxyethoxy)benzene 
• 313656-02-9 2-[3-(2-{[3-(1-Piperazinyl)-2-pyrazinyl]oxy}ethoxy)phenoxy]ethanol, Maleate 
• 1450928-37-6 C₂₂H₂₄N₂O₄ 
• 1450928-36-5 C₂₂H₂₀N₂O₈ 
• 1379612-26-6 O,O'-benzene-1,3-bis[ethoxy-2-(4-phenoxyphenyldithiophosphonic acid)] 
• 1379612-23-3 O,O'-benzene-1,3-bis[ethoxy-2-(3,5-di-tert-butyl-4-hydroxyphenyldithiophosphonic acid)] 
• 1282042-48-1 1,3-bis[2-(pyrrol-2-carbonyloxy)ethoxy]benzene 
• 84040-78-8 1,3-bis-(2-vinyloxy-ethoxy)-benzene 

Relevant articles and documents

Enhanced Basicity of the 2-Position of 1,3-Dialkoxybenzenes in S1: Acid Catalyzed Photochemical Proton/Deuteron Exchange

The photochemistry of several 1,3-dialkoxy-substituted benzenes 1-8 has been studied in aqueous H2SO4 (D2SO4) solution.In contrast to ground state behaviour, all of these compounds (with the exception of 7) are photoprotonated efficiently (via S1) and almost exclusively at the 2-position (and to a much lesser extent at the 5-position) to give dialkoxy-substituted cyclohexadienyl cation intermediates (2,6-dialkoxybenzenonium ions), resulting in proton/deuteron exchange of the 2-position of the benzene ring for all systems except 4 (and 7).In the ground state, protonation takes place predominantly at the 4-position for 1-4 and at the 6-position for 5 and 6.In the case of 4, photoprotonation at the 2-position is implicated by observation of fluorescence quenching by acid but deuterium exchange at this position is not possible.Photoprotonation (quenching) rate constants (kH) were calculated by Stern-Volmer analysis of steady state fluorescence quenching by proton and are in the range 0.9-3E9 M-1 s-1.Quantum yields for deuterium incorporation in 4:1 aqueous D2SO4-CH3CN are reported for several substrates at selected acidities.The sigmoid dependence of plots of fluorescence quenching vs acidity is used to give estimated pKBH(1+)* of ca. 0.1-0.5 for these substrates, indicating that they are much more basic in S1 than in S0.

A new class of flavonoids bearing macrocyclic polyethers by stereoselective photochemical cycloaddition reaction

A new class of flavonoids bearing cyclic polyethers involving a phenyl ring was conveniently provided by the intramolecular photochemical dimerization of 2-chromonecarboxylic esters. Irradiation of 2-chromonecarboxylate with a polyether tethered at both ends promoted intramolecular [2 + 2] cyclobutane formation leading to 14- to 27-membered cyclic polyethers. The efficiency depended on the substituted position of the phenyl ring, with ortho- and meta-substituted derivatives giving cycloadducts in good chemical yields and quantum efficiencies, whereas the para-derivatives were inert toward photolysis. X-ray crystallographic analysis revealed that the stereochemistry of the macrocyclic cycloadducts exhibited C2-symmetry.

Path selection for conformational interconversions in [2]catenanes

The conformational interconversions of several [2]catenanes containing a dibenzo-34-crown-10 ether (BPP34C10) interlocked with rings containing two 4,4′-dipyridyls tethered by different aryl spacers have been studied. Blocking groups on the tethers enabled the two pathways for circumrotation of the BPP34C10 to be open or blocked. The activation barrier for migration along the open tethers varied from 11 to 13 kcal/mol. This study demonstrates an ability to select the pathway for conformational interconversions in [2]catenanes.