99-63-8

Basic information

• Product Name: 1,3-Benzenedicarbonyl chloride
• Synonyms: Isophthaloylchloride (6CI,8CI);Isophthalic acidchloride;Isophthalic acid dichloride;1,3-Benzenedicarbonyl chloride;1,3-Bis(chlorocarbonyl)benzene;1,3-Di(chlorocarbonyl)benzene;Isophthalic chloride;Isophthaloyldichloride;Isophthalyl chloride;Isothaloyl chloride;NSC 41884;m-Benzenedicarbonyl chloride;m-Phthalic dichloride;m-Phthaloylchloride;m-Phthaloyl dichloride;Isophthaloyl Chloride;Isophthaloyl dichloride
• CAS NO: 99-63-8
• Molecular Formula: C₈H₄Cl₂O₂
• Molecular Weight: 203.02
• EINECS: 202-774-7
• Mol File: 99-63-8.mol
• Article Data: 77

Chemical Properties

• Melting Point: 43-45℃
• Boiling Point: 276.7 °C at 760 mmHg
• Flash Point: 131.9 °C
• Appearance: white crystalline mass
• Density: 1.427 g/cm³
• Vapor Pressure: 0.00473mmHg at 25°C
• Refractive Index: 1.571
• Storage Temp.: Store below +30°C.
• Water Solubility: reacts
• BRN: 638342
• CAS DataBase Reference: 1,3-Benzenedicarbonyl chloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Benzenedicarbonyl chloride(99-63-8)
• EPA Substance Registry System: 1,3-Benzenedicarbonyl chloride(99-63-8)

Safety Data

• Hazard Codes: C:Corrosive
• Statements: R34:
• Safety Statements: S24/25:; S7/8:
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 1
• RTECS: NT2625000
• F: 21
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 99-63-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 99-63-8 differently. You can refer to the following data:
1. Intermediate, dyes, synthetic fibers, resins, films, protective coatings, laboratory reagent.
2. Isophthaloyl dichloride is used in a variety of performance polymers and fibers, where it impacts flame resistance, temperature stability, chemical resistance, and flexibility. In addition, it is an effective stabilizer for urethane prepolymers due to its ability to scavenge water. Also used in aromatic fiber raw materials.

General Description

Isopthaloyl chloride acts as a crosslinking agent in various polymerization reactions.

Flammability and Explosibility

Nonflammable

InChI:InChI=1/C8H4Cl2O2/c9-7(11)5-2-1-3-6(4-5)8(10)12/h1-4H

Synthetic route

isophthalic acid (121-91-5) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With thionyl chloride at 80℃; for 4h;	100%
With thionyl chloride In N,N-dimethyl acetamide; acetonitrile at 120℃; for 1h; Solvent; Large scale;	99.4%
With thionyl chloride In N,N-dimethyl-formamide	98%

phosgene (75-44-5) + isophthalic acid (121-91-5) → dimethyl Isophthalate (1459-93-4) + benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With pyridine In dichloromethane	A n/a B 100%

m-xylene (108-38-3) → benzene-1,3-dicarbonyl dichloride (99-63-8) + 3-Methylbenzoyl chloride (1711-06-4)

Conditions	Yield
Stage #1: m-xylene With N-hydroxyphthalimide; cobalt(II) phthalocyanine; μ-oxo[manganese(III) tetraphenylporphine]2; oxygen at 135℃; under 3750.38 Torr; Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;	A 8.4% B 65.7%
Stage #1: m-xylene With manganese(IV) oxide; oxygen; cobalt(II) diacetate tetrahydrate at 156℃; under 7500.75 Torr; Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;	A 58% B 25%

dimethyl Isophthalate (1459-93-4) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With chlorine at 220℃;

1,3-bis-trichloromethyl-benzene (881-99-2) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With water; iron(III) chloride at 130℃;
With titanium(IV) oxide at 270℃;
With maleic acid; zinc(II) chloride at 130℃;
With iron(III) chloride at 110℃; for 1h; Temperature;
With iron(III) chloride; isophthalic acid In melt at 100 - 110℃;

isophthalic acid (121-91-5) + acetyl chloride (75-36-5) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
at 130℃;
at 130℃;

isophthalic acid (121-91-5) + 1,3-bis-trichloromethyl-benzene (881-99-2) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
iron(III) chloride In benzene at 80℃; Rate constant; Kinetics; Mechanism; activation energy, reaction order;

ethanol (64-17-5) + isophthalic acid (121-91-5) → diethyl 3,3'-(1,3,4-oxadiazole-2,5-diyl)dibenzoate (2425-96-9) + benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
Yield given. Multistep reaction;	A n/a B 4.2 g

isophthalic acid bis(trimethylsilyl)ester → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane 1.) 0 deg C, 1 h, 2.) RT, 1 h;

thionyl chloride (7719-09-7) + isophthalic acid (121-91-5) → benzene-1,3-dicarbonyl dichloride (99-63-8)

isophthalic acid (121-91-5) + phosphorus pentachloride (10026-13-8, 874483-75-7) → benzene-1,3-dicarbonyl dichloride (99-63-8)

1,3-bis-trichloromethyl-benzene (881-99-2) + titanium (IV)-oxide + vanadium(V)-oxide → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
at 270℃;

Tributylphosphine oxide (814-29-9) + isophthalic acid (121-91-5) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With thionyl chloride

Isophthalaldehyde (626-19-7) + terephthalaldehyde, (623-27-8) → terephthaloyl chloride (100-20-9) + benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
With chlorine at 43℃; for 0.5h; Product distribution / selectivity; visible light irradiation;

m-xylene (108-38-3) → benzene-1,3-dicarbonyl dichloride (99-63-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorine / 14 h / 60 - 180 °C 2: iron(III) chloride / 1 h / 110 °C View Scheme
Multi-step reaction with 2 steps 1: chlorine / 80 - 180 °C / Irradiation; Industrial scale 2: isophthalic acid; iron(III) chloride / melt / 100 - 110 °C View Scheme

glycine (56-40-6) + benzene-1,3-dicarbonyl dichloride (99-63-8) → [(3-{[(carboxymethyl)amino]carbonyl}benzoyl)amino]acetic acid (124842-39-3)

Conditions	Yield
Stage #1: glycine With sodium hydroxide In water at 10℃; Cooling with ice; Stage #2: benzene-1,3-dicarbonyl dichloride In water; toluene for 1h; pH=1;	100%
With sodium hydroxide In diethyl ether	87%
With sodium hydroxide
With sodium hydroxide

benzene-1,3-dicarbonyl dichloride (99-63-8) + ethyl (triphenylphosphoranylidene)acetate (1099-45-2) → 1,3-bis[(ethoxycarbonyl)(triphenylphosphoranylidene)acetyl]benzene

Conditions	Yield
With triethylamine In toluene at 20℃; for 12h; Acylation; transylidation;	100%

(S)-valinol (2026-48-4) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N,N'-bis-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-isophthalamide (475110-08-8)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 12h;	100%
With triethylamine In dichloromethane at 20℃; for 12h;	95%
With triethylamine In dichloromethane at 0 - 25℃; for 8h;	69%

L-Phenylalaninol (3182-95-4) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N1,N3-bis[(S)-1-hydroxy-3-phenylpropan-2-yl]isophthalamide (475110-10-2)

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 12h;	100%
With triethylamine In dichloromethane at 0 - 25℃; for 8h;	70%
With triethylamine In dichloromethane at 0 - 20℃;	53%

1-methylaminopyrene hydrochloride (93324-65-3) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N,N'-bis(1-pyrenylmethyl)isophthalamide

Conditions	Yield
With triethylamine In tetrahydrofuran Reflux;	100%
With triethylamine In dichloromethane at 20℃;	54%

2,2-bis(3-amino-4-hydroxyphenyl)hexafluoropropane (83558-87-6) + benzene-1,3-dicarbonyl dichloride (99-63-8) + 4,4'-bis(chlorocarbonyl)diphenyl oxide (7158-32-9) → poly(hexafluoro-2,2-bis(3-amino-4-hydroxyphenyl)propane-co-isophthaloyl chloride-co-4,4-oxydibenzoyl chloride)

Conditions	Yield
With pyridine In 1-methyl-pyrrolidin-2-one at 0 - 20℃;	100%

potassium thioacyanate (333-20-0) + benzene-1,3-dicarbonyl dichloride (99-63-8) → 1,3-benzenedicarbonyl diisothiocyanate (70112-91-3)

Conditions	Yield
In acetone at 20℃; for 1h;	100%
In benzene at 110 - 120℃; for 6h; Reflux;
In acetone at 20℃; for 1h;

5,10,15-tri[p-(9-methoxytriethylenenoxy)phenyl]-20-[p-hydroxyphenyl]porphyrin + benzene-1,3-dicarbonyl dichloride (99-63-8) → 5,10,15-tri[p-(9-methoxytriethyleneoxy)phenyl]-20-[p-phenylisophthalate chloride]porphyrin

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h;	100%

benzene-1,3-dicarbonyl dichloride (99-63-8) + benzene (71-43-2) → 1,3-dibenzoylbenzene (3770-82-9)

Conditions	Yield
With aluminium trichloride at 23℃; for 20h; Friedel-Crafts acylation;	99%
With aluminium trichloride
With aluminum (III) chloride Friedel Crafts acylation;
With aluminum (III) chloride
With aluminum (III) chloride at 20 - 60℃; for 20h; Inert atmosphere; Darkness;	10.52 g

benzene-1,3-dicarbonyl dichloride (99-63-8) + phenol (108-95-2) → diphenyl isophthalate (744-45-6)

Conditions	Yield
With N-benzyl-N,N,N-triethylammonium chloride In cyclohexane at 25℃; for 4h; Concentration; Temperature; Reflux;	98.87%
With N-benzyl-N,N,N-triethylammonium chloride In ethanol at 10℃; for 3h; Temperature; Reflux;	98.91%
With potassium carbonate In 1,2-dichloro-ethane at 10℃; for 4h; Concentration; Temperature; Solvent; Reagent/catalyst;	92.1%
In chloroform at 20℃; for 4.5h; Temperature; Concentration;	89.7%

1,2,4-Triazole (288-88-0) + benzene-1,3-dicarbonyl dichloride (99-63-8) → isophthaloyl bis(1,2,4-triazole)

Conditions	Yield
In dichloromethane at 20℃; for 1.5h;	98.8%

1,2,4-Triazole (288-88-0) + benzene-1,3-dicarbonyl dichloride (99-63-8) → isophthaloyl bis(1,2,4-triazole)

Conditions	Yield
In dichloromethane for 1.5h;	98.8%
With triethylamine In toluene for 36h; Schlenk technique; Inert atmosphere; Reflux;	54%

fluorobenzene (462-06-6) + benzene-1,3-dicarbonyl dichloride (99-63-8) → 1,3-bis(4'-fluorobenzoyl)benzene (108464-88-6)

Conditions	Yield
With aluminium trichloride at 23℃; for 4h; Friedel-Crafts acylation;	98%
Stage #1: benzene-1,3-dicarbonyl dichloride With aluminum (III) chloride In dichloromethane for 0.5h; Friedel-Crafts Acylation; Inert atmosphere; Reflux; Stage #2: fluorobenzene In dichloromethane for 12h; Friedel-Crafts Acylation; Inert atmosphere;	56%
Stage #1: benzene-1,3-dicarbonyl dichloride With aluminum (III) chloride In dichloromethane for 0.5h; Reflux; Stage #2: fluorobenzene In dichloromethane for 12h; Reflux;	42%
With aluminum (III) chloride for 8h; Friedel-Crafts Acylation; Inert atmosphere;	3.24 g

benzene-1,3-dicarbonyl dichloride (99-63-8) → isophthaloyl diazide (3027-36-9)

Conditions	Yield
With sodium azide In tetrahydrofuran; water for 1h; cooling;	98%
With sodium azide In N,N-dimethyl-formamide at 20℃; for 2h;
With sodium azide In tetrahydrofuran; water for 2h; Cooling with ice;

benzene-1,3-dicarbonyl dichloride (99-63-8) + 3,3-diphenyl-9-hydroxy-3H-naphtho[2,1-b]pyran → bis(3,3-biphenyl-3H-benzo[f]chromene-9-yl) isophthalic acid ester (1029134-36-8)

Conditions	Yield
With triethylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 12h;	98%

toluene-4-sulfonic acid hydrazide (1576-35-8) + benzene-1,3-dicarbonyl dichloride (99-63-8) → C22H22N4O6S2

Conditions	Yield
In dichloromethane at 0℃; for 2h;	98%

4-AMINO-2,2,6,6-TETRAMETHYLPIPERIDINE (36768-62-4) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N,N'-bis(2,2,6,6-tetramethyl-4-piperidinyl)-1,3-benzenedicarboxamide (42774-15-2)

Conditions	Yield
With aluminum (III) chloride; sodium hydroxide In toluene at 110℃; Concentration;	97.38%
With sodium hydroxide In water; isopropyl alcohol at 30 - 130℃; under 1125.11 - 2475.25 Torr; Alkaline aqueous solution;	95.3%
With sodium hydroxide In chloroform Solvent; Reflux;	94.9%
With sodium hydroxide In water at 7 - 25℃; for 3.5h; Alkaline aqueous solution;	83.6%
With sodium hydroxide In water; isopropyl alcohol at 100℃;	200 g

methyl thiocyanate (556-64-9) + benzene-1,3-dicarbonyl dichloride (99-63-8) → 2,2'-(1,3-Phenylen)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V) (125077-78-3)

Conditions	Yield
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature;	97%

N-(benzyloxycarbonyl)-L-tyrosine methyl ester (13512-31-7) + benzene-1,3-dicarbonyl dichloride (99-63-8) → Isophthalic acid bis-[4-((S)-2-benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-phenyl] ester (226889-63-0)

Conditions	Yield
With dmap In dichloromethane; acetonitrile at 20℃; for 12h; Substitution;	97%

p-xylylidenediamine (539-48-0) + benzene-1,3-dicarbonyl dichloride (99-63-8) + (E)-But-2-enedioic acid bis-[(2,2-diphenyl-ethyl)-amide] → [2]-(1,2,14,20-tetraaza-2,6,15,19-tetraoxo-3,5,9,12,16,18,22,25-tetrabenzocyclohexacosane)-(E)-(N,N'-bis(2',2'-diphenylethyl)-2'-butenediamide)rotaxane

Conditions	Yield
With triethylamine In chloroform; acetonitrile	97%
With triethylamine In chloroform; acetonitrile for 2h;	97%

(1R,2S)-2-Amino-1,2-diphenylethanol (23190-16-1) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N,N'-bis((1S,2R)-2-hydroxy-1,2-diphenylethyl)isophthalamide

Conditions	Yield
With triethylamine In dichloromethane for 4h; Heating;	97%
With triethylamine In tetrahydrofuran at 20℃;	43%
With triethylamine In dichloromethane

benzene-1,3-dicarbonyl dichloride (99-63-8) + 3,5-Bis-(trifluoromethyl)aniline (328-74-5) → N1,N3-bis(3,5-bis(trifluoromethyl)phenyl)benzene-1,3-dicarboxamide (181872-56-0)

Conditions	Yield
With triethylamine In chloroform at 40℃; for 70h;	97%
Stage #1: 3,5-Bis-(trifluoromethyl)aniline With triethylamine In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: benzene-1,3-dicarbonyl dichloride In N,N-dimethyl-formamide at 20℃; for 4h; Inert atmosphere;	72%
With dmap; triethylamine In N,N-dimethyl-formamide at 0 - 75℃;	52%
With dmap; triethylamine In dichloromethane at 20℃; for 24h;	22%

benzene-1,3-dicarbonyl dichloride (99-63-8) + 4-amino-1,5-naphthalenedisulphonic acid disodium salt → tetrasodium 4,4'-[1,3-phenylenebis(carbonylimino)]bis-1,5-naphthalenedisulfonate

Conditions	Yield
With sodium carbonate In chloroform; water at 0 - 25℃;	97%

N,O-dimethylhydroxylamine*hydrochloride (6638-79-5) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N1,N3-bismethoxy-N1,N3-dimethyl-1,3-benzenedicarboxamide (1458033-48-1)

Conditions	Yield
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; Stage #2: benzene-1,3-dicarbonyl dichloride In dichloromethane at 0 - 20℃;	97%
Stage #1: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In dichloromethane at 0℃; for 0.166667h; Inert atmosphere; Stage #2: benzene-1,3-dicarbonyl dichloride In dichloromethane at 0 - 20℃; for 5h; Inert atmosphere;	97%

meta-aminobenzoic acid (99-05-8) + benzene-1,3-dicarbonyl dichloride (99-63-8) → 3,3'-(Isophthaloylbis(azanediyl))dibenzoic acid

Conditions	Yield
With pyridine at 20℃;	97%

2,4-Dichloroaniline (554-00-7) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N,N'-bis(2,4-dichlorophenyl)isophthalamide

Conditions	Yield
With potassium hydroxide In acetonitrile at 20℃; Inert atmosphere;	97%

tert-butylamine (75-64-9) + benzene-1,3-dicarbonyl dichloride (99-63-8) → N1,N3-di-tert-butylisophthalamide (82292-40-8)

Conditions	Yield
In dichloromethane for 2h; Acylation;	96%

benzene-1,3-dicarbonyl dichloride (99-63-8) + (9,10-di(1,3-dithiol-2-ylidene)-9,10-dihydroanthracen-2-yl)methanol (475290-46-1) → bis{[9,10-di(1,3-dithiol-2-ylidene)-9,10-dihydroanthracen-2-yl]methyl} isophthalate

Conditions	Yield
With dmap In dichloromethane at 20℃; for 2h;	96%

Upstream product

• 108-38-3 m-xylene 
• 626-19-7 Isophthalaldehyde 
• 623-27-8 terephthalaldehyde, 
• 75-44-5 phosgene 
• 121-91-5 isophthalic acid 
• 814-29-9 Tributylphosphine oxide 
• 881-99-2 1,3-bis-trichloromethyl-benzene 
• 10026-13-8 phosphorus pentachloride 
• 7719-09-7 thionyl chloride 
• 64-17-5 ethanol 
• 75-36-5 acetyl chloride 
• 1459-93-4 dimethyl Isophthalate 

Downstream Products

• 1087-21-4 diallyl isophthalate 
• 124842-39-3 [(3-{[(carboxymethyl)amino]carbonyl}benzoyl)amino]acetic acid 
• 112817-57-9 N,N'-bis(6-amino-2-pyridinyl)-1,3-benzenedicarboxamide 
• 81930-85-0 N,N'-Bis(3-ethoxycarbonyl-4,5-dihydrothien-2-yl)-isophthalsaeurediamid 
• 125077-78-3 2,2'-(1,3-Phenylen)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V) 
• 65745-83-7 3,6,9,12,15-pentaoxabicyclo<15.3.1>heneicosa-1(21),17,19-triene-2,16-dione 
• 105410-04-6 m-(Chlorodimethylsilyl)benzoyl chloride 
• 74606-84-1 1,3-bis(chlorodimethylsilyl)benzene 
• 125016-33-3 Isophthaloyl-bis(S-methylhydrazinecarbodithioate) 
• 151322-19-9 dimethyl 3,3'-isophthaloyl-bis-(2-methyldithiocarbazate) 
• 84369-68-6 1,3-bis(2,4,6-triisopropylbenzoyl)benzene 
• 205311-42-8 3'-chloroformyl-2,4,6-triisopropylbenzophenone 
• 85566-05-8 <3-(3-methylbenzoyl)phenyl>(3-methylphenyl)methanone 
• 134639-74-0 1,3-bis-<4-(4-nitrophenoxy)benzoyl>benzene 

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