3748-13-8

Basic information

• Product Name: 1,3-DIISOPROPENYLBENZENE
• Synonyms: M-DIISOPROPENYL BENZENE;1,3-DIISOPROPENYLBENZENE;META-DIISOPROPENYLBENZENE;1,3-DIISOPROPENYLBENZENE 95+%;1,3-Diisopropenylbenzene (stabilized with TBC);1,3-Bis(isopropenyl)benzene;1,3-di(prop-1-en-2-yl)benzene;1,3-Diisopropenylbenzene
• CAS NO: 3748-13-8
• Molecular Formula: C₁₂H₁₄
• Molecular Weight: 158.24
• EINECS: 223-146-9
• Product Categories: Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Monomers;Polymer Science;Styrene and Functionalized Styrene Monomers
• Mol File: 3748-13-8.mol
• Article Data: 6

Chemical Properties

• Melting Point: -40 °C
• Boiling Point: 231 °C(lit.)
• Flash Point: 93 °C
• Appearance: /
• Density: 0.925 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0968mmHg at 25°C
• Refractive Index: n20/D 1.556(lit.)
• Storage Temp.: 2-8°C
• Solubility: Acetonitrile (Slightly), Chloroform (Slightly)
• Water Solubility: 5.6mg/L at 25℃
• Stability: Light Sensitive
• CAS DataBase Reference: 1,3-DIISOPROPENYLBENZENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIISOPROPENYLBENZENE(3748-13-8)
• EPA Substance Registry System: 1,3-DIISOPROPENYLBENZENE(3748-13-8)

Safety Data

• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-61-60
• RIDADR: UN 3082 9/PG 3
• WGK Germany: 2
• RTECS: CY8535000
• Hazardous Substances Data: 3748-13-8(Hazardous Substances Data)

Usage

General Description

1,3-Diisopropenylbenzene, also known by its other name m-Divinylbenzene, is an organic compound with the formula C6H4(CH2C(CH3)=CH2)2. It is a colorless liquid with a distinctive sweet odor. 1,3-Diisopropenylbenzene falls under the aromatic hydrocarbons category and belongs to the family of benzene and its derivatives. It is predominantly used in chemical synthesis as a building block for various other chemicals due to its high reactivity. Being a divinyl compound, it frequently acts as a crosslinking agent in the production of various polymers and resins. Due to its chemical properties, it needs to be handled with care as it can cause irritation to the eyes, skin, and respiratory tract.

InChI:InChI=1/C12H14/c1-9(2)11-6-5-7-12(8-11)10(3)4/h5-8H,1,3H2,2,4H3

Synthetic route

1,3-diacetylbenzene (6781-42-6) + Methyltriphenylphosphonium bromide (1779-49-3) → 1,3-bis(1-methylethenyl)-benzene (3748-13-8)

Conditions	Yield
Stage #1: Methyltriphenylphosphonium bromide With n-butyllithium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: 1,3-diacetylbenzene In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	68%

C18H25ClO4PdS2 → 1,3-bis(1-methylethenyl)-benzene (3748-13-8) + [Pd(μ-methyl thioglycolate(-1H))2]8

Conditions	Yield
In diethyl ether; [D3]acetonitrile; water at 90℃; for 10h; Inert atmosphere; Schlenk technique;	A 6% B 65%

poly(methacrylic acid 1,3-phenylenebis(1-methylethylidene) ester) → poly(methacrylic acid) Mw=18000, PDI=3.5 + 1,3-bis(1-methylethenyl)-benzene (3748-13-8)

Conditions	Yield
at 180℃; for 0.166667h; Product distribution; Further Variations:; Temperatures; with or without irradiation;

1,3-bis(1',1'-dimethylhydroxymethyl)benzene (1999-85-5) → 1,3-bis(1-methylethenyl)-benzene (3748-13-8)

Conditions	Yield
sulfuric acid In 4-methyl-2-pentanone at 90℃; under 760.051 Torr; for 0.666667h; Product distribution / selectivity;

methanol (67-56-1) + carbon monoxide (201230-82-2) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → dimethyl 3,3'-(1,3-phenylene)dibutyrate

Conditions	Yield
With 1,3-bis(tert-butyl(pyridin-2-yl)phosphanyl)propane; palladium(II) acetylacetonate; toluene-4-sulfonic acid for 20h; Sealed tube; Inert atmosphere; Autoclave;	99%
With platinum(II) bis(acetylacetonate); C28H36P2; toluene-4-sulfonic acid at 120℃; under 30402 Torr; for 20h; Sealed tube; Inert atmosphere; Autoclave;	86%

carbon monoxide (201230-82-2) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 3,3'-(1,3-phenylene)dibutyric acid

Conditions	Yield
With sulfuric acid; α,α′-bis(2-pyridyl(tert-butyl)phosphino)-o-xylene; water; palladium(II) acetylacetonate; acetic acid at 20 - 100℃; under 30003 Torr; for 20h; Inert atmosphere; Autoclave;	99%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + 2-pyridylmethyl formate (401515-97-7) → 3-(3-isopropenyl-phenyl)-butyric acid pyridin-2-ylmethyl ester

Conditions	Yield
With dodecacarbonyl-triangulo-triruthenium In tetrahydrofuran at 135℃; for 12h;	91%
With tetra-(n-butyl)ammonium iodide; dodecacarbonyl-triangulo-triruthenium In tetrahydrofuran at 90℃; for 12h;	85%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1,3-bis(1-azido-2-chloropropan-2-yl)benzene

Conditions	Yield
With chlorine azide In water; toluene at 20℃; for 0.0188889h; Flow reactor;	91%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1,3-diisopropylbenzene (99-62-7)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In dichloromethane under 3750.38 Torr; for 19h;	88%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + ethenetetracarbonitrile (670-54-2) → 1,1,2,2,5,5,6,6-Octacyano-1,1a,2,3,5a,5,6,7-octahydro-4,8-dimethylphenanthrene (134782-06-2)

Conditions	Yield
In acetonitrile at 28℃; for 1h;	87%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + benzyl 2-triethylsilyl-2-oxoacetate (443988-54-3) → benzyl 2-hydroxy-4-(3-(prop-1-en-2-yl)phenyl)-2-(triethylsilyl)-pent-4-enoate

Conditions	Yield
With zinc(II) chloride In dichloromethane; water at 20℃; for 17h; Schlenk technique;	82%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + malononitrile (109-77-3) → 2-methyl-2-(3-(prop-1-en-2-yl)phenyl)cyclopropane-1,1-dicarbonitrile (1551163-36-0)

Conditions	Yield
With [bis(acetoxy)iodo]benzene; potassium carbonate In 1,2-dichloro-ethane at 50℃; for 1h;	81%

2,2'-azobis(isobutyronitrile) (78-67-1) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 2,2-dimethyl-4-(3-(prop-1-en-2-yl)phenyl)pent-4-enenitrile

Conditions	Yield
With iodine In dimethyl sulfoxide at 80℃; for 6h; Sealed tube; Inert atmosphere;	81%

p-cresol (106-44-5) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) + aluminium hydride (7784-21-6) → 1,3-Di[2-(2-hydroxy-5-methylphenyl)-2-propyl]-benzene

Conditions	Yield
In n-heptane; acetone	80%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + N,N-dimethyl-aniline (121-69-7) → C20H25N

Conditions	Yield
With C31H51N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 120℃; for 43h; Inert atmosphere; regioselective reaction;	78%

methanol (67-56-1) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1-(3-(1,1-dimethoxyethyl)phenyl)ethanone (1219696-78-2) + 1,3-diacetylbenzene (6781-42-6) + 1-(3-(prop-1-en-2-yl)phenyl)ethanone (87771-42-4)

Conditions	Yield
With ozone at 20℃; for 3.26667h;	A 5% B 75% C 2%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + N,N-dimethyl-aniline (121-69-7) → C28H36N2

Conditions	Yield
With C31H51N2ScSi2; N,N'-dimethylaniliniumtetrakis(pentafluorophenyl)borate In toluene at 120℃; for 38h; Inert atmosphere; regioselective reaction;	73%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + benzyl 2-trimethylsilyl-2-oxoacetate (443988-53-2) → dibenzyl 4,4′-(1,3-phenylene)bis(2-hydroxy-2-(trimethylsilyl)-pent-4-enoate)

Conditions	Yield
With zinc(II) chloride In dichloromethane; water at 20℃; for 2h; Schlenk technique;	72%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 2-(3-isopropenylphenyl)propan-1-ol (457928-66-4)

Conditions	Yield
Stage #1: 1,3-bis(1-methylethenyl)-benzene With dimethylsulfide borane complex In tetrahydrofuran at 0 - 20℃; Stage #2: With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran	55%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + N-(4-Methoxy-phenyl)-4-methyl-benzenesulfonamide (1150-26-1) → C26H27NO3S

Conditions	Yield
With [n-Bu4N][BF4]; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,2-dichloro-ethane; acetonitrile at 20℃; for 2h; Electrolysis; Inert atmosphere; Electrochemical reaction; regioselective reaction;	53%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + 2-oxopyrrolidine-1-carboxamide (40451-67-0) → BTMI (133861-85-5)

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile at 65℃; for 6h; Product distribution / selectivity;	51%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + phenylacetylene (536-74-3) → 1,3-bis(1-methyl-3-phenylcyclobut-2-en-1-yl)benzene (1235454-13-3)

Conditions	Yield
With (acetonitrile)[2-di-tert-butyl(2′,4′,4′,6'-triisopropylbiphenyl)phosphine]gold(I) hexafluoroantimonate In dichloromethane at 20℃; for 20h; Inert atmosphere; regioselective reaction;	48%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1-(3-chloroprop-1-en-2-yl)-3-(prop-1-en-2-yl)benzene + 1,3-bis(3-chloroprop-1-en-2-yl)benzene

Conditions	Yield
With N-chloro-succinimide; chloro-trimethyl-silane; ytterbium(III) triflate In tetrahydrofuran; dichloromethane at 20℃; for 3h; Inert atmosphere;	A 47% B 20%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + α-methoxycarbonylmaleic anhydride (69327-00-0) → 1,5-Dicarbomethoxy-1,1a,2,3,5a,5,6,7-octahydro-4,8-dimethylphenanthrene-1,2,5,6-tetracarboxylic Acid Dianhydride (134782-08-4)

Conditions	Yield
In acetonitrile at 28℃; other condition: ether as solvent; Further byproducts given;	45%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1-(3-(prop-1-en-2-yl)phenyl)ethanone (87771-42-4)

Conditions	Yield
Stage #1: 1,3-bis(1-methylethenyl)-benzene With ozone In methanol; dichloromethane at -78℃; Stage #2: With triphenylphosphine	45%
With dihydrogen peroxide; [Co4(SO4)3(F)3(2,4,6-tris-(4-pyridyl)-1,3,5-triazine)2(tatb)] In ethanethiol at 60℃;	95 %Spectr.

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1,3-di(isothiazol-4-yl)benzene

Conditions	Yield
With ammonium iodide; potassium ethyl xanthogenate In water; dimethyl sulfoxide at 130℃; for 24h; Schlenk technique;	41%

maleic anhydride (108-31-6) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → 1,1a,2,3,5a,5,6,7-Octahydro-4,8-dimethylphenanthrene-1,2,5,6-tetracarboxylic Acid Dianhydride (13592-50-2)

Conditions	Yield
In acetonitrile for 18h; Heating;	40%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → Ru3(CO)7(μ3-η(2):η(2):η(2)-C6H4-(η(2)-CCH3CH2)2-1,3) (169829-99-6) + Ru4(CO)9(μ3-η(2):η(2):η(2)-C6H4-(η(2)-CCH3CH2)2-1,3)

Conditions	Yield
In octane refluxing (1.5 h); filtering, evapn. (reduced pressure), chromy. (CH2Cl2 / hexane = 1 : 4),extg. (CH2Cl2);	A 32% B 27%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) + dithiobenzoic acid sodium salt (3682-36-8) → C26H26S4 (257955-88-7)

Conditions	Yield
With hydrogenchloride In n-heptane; water for 16h;	27%

dodecacarbonyl-triangulo-triruthenium (15243-33-1) + 1,3-bis(1-methylethenyl)-benzene (3748-13-8) → Ru4(CO)9C6H4[C(CH3)CH2]2 (169830-00-6, 164663-47-2)

Conditions	Yield
In octane thermolysis for 1.5 h; evapn., TLC;	27%

1,3-bis(1-methylethenyl)-benzene (3748-13-8) → poly(1,3-diisopropenylbenzene peroxide); Monomer(s): 1,3-diisopropenylbenzene

Conditions	Yield
With 2,2'-azobis(isobutyronitrile); oxygen In benzene at 55℃; under 5171.48 Torr; for 24h;	26%

Upstream product

• 6781-42-6 1,3-diacetylbenzene 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 1999-85-5 1,3-bis(1',1'-dimethylhydroxymethyl)benzene 

Downstream Products

• 41009-75-0 1,3-bis(1-methylcyclopropyl)benzene 
• 2778-42-9 1,3-bis(1-isocyanato-1-methylethyl)benzene 
• 2094-99-7 1-(1-isocyanato-1-methylethyl)-3-(1-methylethenyl)benzene 

Relevant articles and documents

Tiara-like octanuclear palladium(II) and platinum(II) thiolates and their inclusion complexes with dihalo- or iodoalkanes

A tiara-like octanuclear palladium thiolate complex, [Pd(μ-SCH 2CO2Me)2]8, that has a toroidal structure was synthesized via reactions of either PdCl2 with methyl thioglycolate/N,N-diisopropylethylamine (DIEA) (conventional method) or [PdCl2(MeCN)2] with m-C6H4(CMe 2SCH2CO2Me)2 (alternative method). In the latter method, the tiara-like complex formed via the corresponding SCS-pincer complex and/or 1:1 PdCl2 and ligand complexes. With respect to the platinum analogues, the alternative method efficiently produced the tiara-like octanuclear complex [Pt(μ-SCH2CO 2Me)2]8 in high purity. Small molecules, such as CH2Cl2, ClCH2CH2Cl, CH 2Br2, and CH3I, were accommodated in the inner voids of the tiara rings to form 1:1 inclusion complexes. These complexes are stabilized not only by weak CH...X hydrogen bonds (X = Cl or Br) between the methylene protons of four or eight axially positioned methoxycarbonylmethyl groups on the tiara rings and the halogen atoms of the guest molecules but also by weak coordination of the halogen atoms to the transition-metal atoms.

PROCESS FOR PRODUCING DIHYDROXYBENZENE AND DIISOPROPYLBENZENDICARBINOL

A process for simultaneously producing a dihydroxybenzene and a diisopropylbenzene dicarbinol, which contains subjecting a diisopropylbenzene with an oxygen containing gas to obtain an oxidation reaction mixture containing a diisopropylbenzene dihydroperoxide and a diisopropylbenzene hydroxy hydroperoxide followed by an extraction separation step, a decomposition step, a distillation separation step, a reduction step and a post-treatment step in this order, the process containing purifying the diisopropylbenzene dicarbinol from the liquid containing the diisopropylbenzene dicarbinol obtained in the reduction step through purification operations containing crystallization, filtration and subsequent drying, and supplying a filtrate obtained by the filtration to the decomposition step and/or distillation separation step.