3634-83-1

Basic information

• Product Name: 1,3-Bis(isocyanatomethyl)benzene
• Synonyms: 1,3-bis(isocyanatomethyl)-benzen;1,3-bis-(isokyanatomethyl)benzen;1,3-xylylenediisocyanate;isocyanicacid,m-phenylenedimethyleneester;m-phenylenedimethyleneisocyanate;m-xdi;m-xylene-alpha,alpha’-diisocyanate;m-xylidenediisocyanate
• CAS NO: 3634-83-1
• Molecular Formula: C₁₀H₈N₂O₂
• Molecular Weight: 188.18
• EINECS: 222-852-4
• Product Categories: Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research
• Mol File: 3634-83-1.mol
• Article Data: 30

Chemical Properties

• Melting Point: -7°C
• Boiling Point: 88-90 °C0.02 mm Hg(lit.)
• Flash Point: 42°C
• Appearance: /
• Density: 1.202 g/mL at 20 °C(lit.)
• Vapor Pressure: 0.021Pa at 20℃
• Refractive Index: n20/D 1.451
• Storage Temp.: 2-8°C
• BRN: 781825
• CAS DataBase Reference: 1,3-Bis(isocyanatomethyl)benzene(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Bis(isocyanatomethyl)benzene(3634-83-1)
• EPA Substance Registry System: 1,3-Bis(isocyanatomethyl)benzene(3634-83-1)

Safety Data

• Hazard Codes: C
• Statements: 10-34-42
• Safety Statements: 16-23-26-36/37/39-45
• RIDADR: UN 2920 8/PG 2
• WGK Germany: 2
• RTECS: NR0147000
• F: 8-10-19-21
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 3634-83-1(Hazardous Substances Data)

Usage

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. A severe skin and eye irritant. A sensitizer. A flammable liquid. When heated to decomposition it emits very toxic fumes of NOx. See also ISOCYANATES.

InChI:InChI=1/C8H8N2O2/c11-9-5-7-2-1-3-8(4-7)6-10-12/h1-4H,5-6H2

Synthetic route

phosgene (75-44-5) + 1,3-di(aminomethyl)benzene (1477-55-0) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In water; 1,2-dichloro-benzene at 20℃; Autoclave; Large scale; Stage #2: phosgene In water; 1,2-dichloro-benzene at 145℃; for 2h; Autoclave; Large scale;	99.9%
With picoline In dichloromethane at -5 - 140℃; for 4h; Reagent/catalyst; Temperature;	98.3%
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In chlorobenzene at 10℃; under 750.075 Torr; for 1.5h; Flow reactor; Large scale; Stage #2: phosgene In chlorobenzene at 131℃; under 750.075 Torr; for 3h; Temperature; Pressure; Solvent; Flow reactor; Large scale;	98.5%

diethyl 1,3-phenylenebis(methylene)dicarbamate (13406-38-7) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
With zinc(II) oxide In 1,2-dichloro-benzene at 270℃; under 5625.56 Torr; for 2h; Temperature; Solvent; Reagent/catalyst; Pressure; Inert atmosphere; Sealed tube;	99.1%

1,3-bis-[(methoxycarbonylamino)-methyl]-benzene (54772-36-0) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
With phthalic acid dimethyl ester; lead(II) acetate trihydrate; zinc(II) acetate dihydrate; sodium 4-dodecylbenzenesulfonate at 250℃; under 3750.38 Torr; for 0.333333h; Reagent/catalyst; Pressure; Inert atmosphere;	98.6%

1,3-di(aminomethyl)benzene (1477-55-0) + bis(trichloromethyl) carbonate (32315-10-9) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In chlorobenzene at 60 - 65℃; for 1h; Stage #2: bis(trichloromethyl) carbonate With hydrogenchloride; triphenylphosphine In chlorobenzene at 132℃; Solvent; Temperature;	94.8%
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In water at 10 - 60℃; for 2h; Large scale; Stage #2: bis(trichloromethyl) carbonate In 1,2-dichloro-benzene at 130℃; for 28h; Temperature; Large scale;	94%
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride In water at 50℃; for 1h; Stage #2: bis(trichloromethyl) carbonate In 1,2-dichloro-benzene at 130℃; Temperature;	90%

silver (I) nitro cyanamide (20236-50-4) + 1,3-bis-(bromomethyl)benzene (626-15-3) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
With magnesium sulfate In benzene at 80℃; for 3h;	94%

phosgene (75-44-5) → 3-chloromethylbenzyl isocyanate + m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Stage #1: 1,3-di(aminomethyl)benzene With hydrogenchloride; 1,2-dichloro-benzene at 120℃; for 3 - 7h; Pressure between atmospheric and 0.05 MPa higher than atmospheric; Stage #2: phosgene In 1,2-dichloro-benzene at 160℃; for 6 - 8h; Product distribution / selectivity;	A n/a B 93.71%

C40H56N2O4 → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
With isocyanurate at 200 - 250℃; for 200h;	87%

[3-(Phenoxycarbonylamino-methyl)-benzyl]-carbamic acid phenyl ester (16578-54-4) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
With DURANATE TPA-100 In 1,2-dichloro-benzene at 250℃; under 6000.6 Torr; for 200h; Inert atmosphere;	85%
In 1,2-dichloro-benzene at 160 - 250℃; under 6000.6 Torr; Inert atmosphere;	82%

phosgene (75-44-5) + Trimethylsilanyl-{3-[(trimethylsilanyl-amino)-methyl]-benzyl}-amine (54731-28-1) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
In toluene

phosgene (75-44-5) + 1,3-Bis-(1,1,3,3-tetramethyl-disilazan-2-ylmethyl)-benzene (57586-52-4) → m-xylylene diisocyanate (3634-83-1)

1,3-di(aminomethyl)benzene (1477-55-0) + trichloromethyl chloroformate (503-38-8) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
With pyrographite In ethyl acetate Heating;

1,3-di(aminomethyl)benzene (1477-55-0) + di-tert-butyl tricarbonate (24424-95-1) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
In dichloromethane at 20℃; for 1h;

1,3-di(aminomethyl)benzene (1477-55-0) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: H2SO4, (NH4)2SO4 2: toluene View Scheme
Multi-step reaction with 2 steps 1: H2SO4 View Scheme
Multi-step reaction with 2 steps 1.1: 12 h / 140 °C / 7500.75 - 60006 Torr / Autoclave 1.2: 10 h / 80 °C 2.1: 1,2-dichloro-benzene / 160 - 250 °C / 6000.6 Torr / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1.1: 12 h / 200 °C / 7500.75 - 60006 Torr / Autoclave 1.2: 10 h / 80 °C 2.1: 1,2-dichloro-benzene / 160 - 250 °C / 6000.6 Torr / Inert atmosphere View Scheme

N,N'-(1,3-phenylenebis(methylene))diformamide (59276-03-8) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
In 1-Methylnaphthalene

m-xylylene bis(2,2,3,3-tetrafluoropropylcarbamate) (1338600-43-3) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
at 200℃; under 7.05071 Torr;

m-xylylene bis(2,2,3,3-tetrafluoropropylcarbamate) (1338600-43-3) → C13H12F4N2O3 + m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
at 235℃;

C13H12F4N2O3 → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Heating;

C18H27ClN2O4 → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: palladium on activated charcoal; sodium carbonate; hydrogen / 5 h / 90 °C / 3750.38 Torr / Autoclave 2: 200 - 300 °C / 100 Torr View Scheme

dibutyl (1,3-phenylenebis(methylene))dicarbamate → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
at 200 - 300℃; under 100 Torr;	51.9 g
at 200 - 300℃; under 100 Torr;	51.9 g

N,N'-meta-xylylene bis(N,N-diisobutylurea) → m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
at 200 - 300℃; under 100 Torr;	37.6 g
at 200 - 300℃; under 100 Torr;	37.6 g

1,3-di(aminomethyl)benzene (1477-55-0) + bis(trichloromethyl) carbonate (32315-10-9) → 3-chloromethylbenzyl isocyanate + 3-(dichloromethyl)benzylisocyanate + m-xylylene diisocyanate (3634-83-1)

Conditions	Yield
In 1,2-dichloro-benzene at 60 - 160℃; for 4h; Large scale;

m-xylylene diisocyanate (3634-83-1) → C10H10Cl2N2O2

Conditions	Yield
With hydrogenchloride In chlorobenzene at 30℃;	99%

m-xylylene diisocyanate (3634-83-1) + hydroxylauryl ether (209588-59-0) → Polymer, Mw 27300; Monomer(s): 13-oxapentacosane-1,25-diol; 1,3-bis(isocyanatomethyl)benzene

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 100℃; for 20h; Polymerization;	98%

methanol (67-56-1) + m-xylylene diisocyanate (3634-83-1) → 1,3-bis-[(methoxycarbonylamino)-methyl]-benzene (54772-36-0)

Conditions	Yield
With triethylamine 15 min, r.t., 30 min, reflux;	95%

5-amino-1H-imidazole-4-carboxamide monohydrochloride (72-40-2) + m-xylylene diisocyanate (3634-83-1) → 1,3-bis(5-amino-4-carbamoylimidazolecarboxamidomethyl)benzene

Conditions	Yield
With triethylamine In acetonitrile for 60h; Ambient temperature;	92%

m-xylylene diisocyanate (3634-83-1) + 3,3-bis(aminomethyl)-2,2′-dimethoxy-1,1′-binaphthalene (201138-33-2) → C34H32N4O4 (1474026-04-4)

Conditions	Yield
In chloroform for 2h; Reflux;	92%

m-xylylene diisocyanate (3634-83-1) + 6-[4-(6-hydroxy-hexyloxy)-phenoxy]-hexan-1-ol (154876-99-0) → Polymer, Mw 24900; Monomer(s): 1,4-bis(6-hydroxyhexyloxy)benzene; 1,3-bis(isocyanatomethyl)benzene

Conditions	Yield
In 1-methyl-pyrrolidin-2-one at 100℃; for 20h; Polymerization;	89%

m-xylylene diisocyanate (3634-83-1) + 4,6-diisopropyl-1,3-bis[methylene-(N'-2-aminophenylureylene)]-m-xylene (246018-53-1) → C38H44N8O4

Conditions	Yield
In N,N-dimethyl-formamide Cycloaddition;	85%

1-(4-nitrophenyl)-3-(2-amino-phenyl)urea (57709-67-8) + m-xylylene diisocyanate (3634-83-1) → 1,1'-(1,3-phenylenebis(methylene))bis(3-(2-(3-(4-nitrophenyl)ureido)phenyl)urea)

Conditions	Yield
In tetrahydrofuran for 4h; Reflux;	85%

(S)-2,2'-diamino-1,1'-binaphthalene (18531-95-8) + m-xylylene diisocyanate (3634-83-1) → (S)-N',N'''-(α,α'-m-xylenediyl)-[2,2'-bis(ureido)-1,1'-binaphthyl]

Conditions	Yield
In toluene for 5h; Inert atmosphere; Reflux;	83%

4,7,10-trioxa-1,13-diaminotridecane (4246-51-9) + m-xylylene diisocyanate (3634-83-1) → C22H36N4O6

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; Cooling with ice;	78%

1,3-dimethanol benzene (626-18-6) + m-xylylene diisocyanate (3634-83-1) → 5,13-Diaza-3,15-dioxatricyclo<15.3.1.117,11>docosa-1(21),7,9,11(22),17,19-hexaene-4,14-dione

Conditions	Yield
With 1H-imidazole In toluene Heating;	77%
With triethylamine In tetrahydrofuran; toluene for 14h; Heating;	77%

1,8-diaminooctan (373-44-4) + m-xylylene diisocyanate (3634-83-1) → C18H28N4O2 (1092725-10-4)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 72h; Inert atmosphere; Cooling with ice;	75%

1-dicyanomethylene-5-(4-aminophenyl)indane (1290140-63-4) + m-xylylene diisocyanate (3634-83-1) → 1,3-bis[4-(1-dicyanomethyleneindan-5-yl)phenylureidomethyl]benzene (1290140-64-5)

Conditions	Yield
In chloroform at 20℃;	75%
In chloroform at 20℃; for 48h; Inert atmosphere;

3,6-dioxa-1,8-diaminooctane (929-59-9) + m-xylylene diisocyanate (3634-83-1) → C16H24N4O4 (1092725-06-8)

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 72.5h; Inert atmosphere; Cooling with ice;	72%

4-vinyl benzylamine (1520-21-4) + m-xylylene diisocyanate (3634-83-1) → 1,1’-(1,3-phenylenebis(methylene))bis(3-(4-vinylphenyl)urea)

Conditions	Yield
In tetrahydrofuran at 20℃;	70%
In tetrahydrofuran at 20℃; Inert atmosphere;	70%

1 ,5-pentanediol (111-29-5) + m-xylylene diisocyanate (3634-83-1) → 5,11-Dioxa-3,13-diaza-bicyclo[13.3.1]nonadeca-1(18),15(19),16-triene-4,12-dione

Conditions	Yield
With triethylamine In tetrahydrofuran; toluene for 14h; Heating;	69%

2.6-bis(hydroxymethyl)pyridine (1195-59-1) + m-xylylene diisocyanate (3634-83-1) → 3,15-Dioxa-5,13,21-triaza-tricyclo[15.3.1.17,11]docosa-1(20),7,9,11(22),17(21),18-hexaene-4,14-dione

Conditions	Yield
With triethylamine In tetrahydrofuran; toluene for 14h; Heating;	68%

N,N'-dicyclohexyl-4-morpholine carboxamidine (4975-73-9) + m-xylylene diisocyanate (3634-83-1) → C44H70N8O4 (117688-76-3)

Conditions	Yield
In dichloromethane Ambient temperature;	65%

3α-amino-5β-colanato di metile (106697-49-8) + m-xylylene diisocyanate (3634-83-1) → bis[(24-methoxycarbonyl)-3-lithocholanyl]-N',N-xylene diurea

Conditions	Yield
In tetrahydrofuran at 20℃;	65%

C17H29NO4S + m-xylylene diisocyanate (3634-83-1) → C37H45N5O8S (870537-25-0)

Conditions	Yield
tin di(2-ethylhexanoate) In acetonitrile at 50℃; for 0.5h;	50%

Upstream product

• 75-44-5 phosgene 
• 1477-55-0 1,3-di(aminomethyl)benzene 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 54772-36-0 1,3-bis-[(methoxycarbonylamino)-methyl]-benzene 
• 16578-54-4 [3-(Phenoxycarbonylamino-methyl)-benzyl]-carbamic acid phenyl ester 
• 13406-38-7 diethyl 1,3-phenylenebis(methylene)dicarbamate 
• 1338600-43-3 m-xylylene bis(2,2,3,3-tetrafluoropropylcarbamate) 
• 59276-03-8 N,N'-(1,3-phenylenebis(methylene))diformamide 
• 24424-95-1 di-tert-butyl tricarbonate 
• 503-38-8 trichloromethyl chloroformate 
• 20236-50-4 silver (I) nitro cyanamide 
• 626-15-3 1,3-bis-(bromomethyl)benzene 
• 57586-52-4 1,3-Bis-(1,1,3,3-tetramethyl-disilazan-2-ylmethyl)-benzene 
• 54731-28-1 Trimethylsilanyl-{3-[(trimethylsilanyl-amino)-methyl]-benzyl}-amine 

Downstream Products

• 124887-69-0 1,3-Bis<(1-carboxymethyl-3-hydantoinyl)methyl>benzene 
• 870537-25-0 C₃₇H₄₅N₅O₈S 
• 391894-58-9 C₁₈H₂₂N₄O₁₀ 
• 124887-70-3 1,3-Bis<(1-carboxymethyl-3-hydantoinyl)methyl>benzene dihydrate 
• 54772-36-0 1,3-bis-[(methoxycarbonylamino)-methyl]-benzene 
• 98128-51-9 Bis-(buta-1,3-dien-2-yl-methyl)-(m-xylylen)-dicarbamat 

Relevant articles and documents

METHOD FOR PRODUCING CARBAMATE AND METHOD FOR PRODUCING ISOCYANATE

The present invention provides a method for producing a carbamate that includes a step (1) and a step (2) described below: (1) a step of producing a compound (A) having a urea linkage, using an organic primary amine having at least one primary amino group per molecule and at least one compound selected from among carbon dioxide and carbonic acid derivatives, at a temperature lower than the thermal dissociation temperature of the urea linkage; and(2) a step of reacting the compound (A) with a carbonate ester to produce a carbamate.

Method for preparing high-purity m-xylylene diisocyanate from non-phosgene

The invention relates to the technical field of isocyanate preparation, in particular to a method for preparing high-purity m-xylylene diisocyanate from non-phosgene. The method for preparing the high-purity m-xylylene diisocyanate from the non-phosgene comprises the following steps: subjecting m-xylylenediamine and dimethyl carbonate to reacting under the action of a catalyst A to obtain methyl m-xylylene dicarbamate; and carrying out a decomposition reaction on methyl m-xylylene dicarbamate under the action of a catalyst B, emptying methanol through nitrogen replacement in the reaction process, and carrying out reduced-pressure distillation after the reaction is finished so as to obtain m-xylylene diisocyanate, wherein the catalyst A is a supported catalyst taking Lewis acid as an activecomponent and nano-SiO2 or nano-TiO2 as a carrier, and the catalyst B is an ultrafine composite oxide. The preparation method of the invention is good in product selectivity, high in yield, high in purity and free of catalyst residues, product quality is improved, and the requirements of high-end fields are met.

METHOD OF PREPARING DIISOCYANATE COMPOSITION AND OPTICAL LENS

In the embodiments, an aqueous hydrochloric acid solution instead of hydrogen chloride gas and solid triphosgene instead of phosgene gas may be used in the process of preparing a diisocyanate from a diamine through a diamine hydrochloride. In addition, the embodiments provide processes for preparing a diisocyanate composition and an optical lens of higher quality, in which the reaction temperature of a diamine hydrochloride composition and triphosgene is controlled to a specific range, or a crude diisocyanate composition obtained from the reaction of a diamine hydrochloride composition and triphosgene is distilled at a specific temperature range, or the molar ratio of a diamine hydrochloride and triphosgene is adjusted to a specific range.