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Terephthaloyl chloride is a chemical compound that undergoes condensation reactions with difunctional α,ω-diaminopolystyrene to yield chain-extended polystyrene containing amide bonds along the polymer backbone. It is also known to undergo interfacial reactions with bovine serum albumin to form thin cross-linked films. Terephthaloyl chloride is characterized by its monoclinic crystal or white crystalline flake structure and is soluble in ethanol and various organic solvents.

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  • 100-20-9 Structure
  • Basic information

    1. Product Name: Terephthaloyl chloride
    2. Synonyms: 1,4-dichloroformylbenzene;p-Phenylenedicarbonyl dichloride;p-phenylenedicarbonyldichloride;p-Phthaloyl dichloride;p-phthaloyldichloride;p-Phthalyl dichloride;p-Phthanoylchloride;Terephthalic acid chloride
    3. CAS NO:100-20-9
    4. Molecular Formula: C8H4Cl2O2
    5. Molecular Weight: 203.02
    6. EINECS: 202-829-5
    7. Product Categories: ACID CHLORIDES;Fluorenes, etc. (reagent for high-performance polymer research);Functional Materials;Reagent for High-Performance Polymer Research;Acid Halides;Carbonyl Compounds;Organic Building Blocks;Piperidines ,Piperazines ,Homopiperidines
    8. Mol File: 100-20-9.mol
  • Chemical Properties

    1. Melting Point: 79-81 °C(lit.)
    2. Boiling Point: 266 °C(lit.)
    3. Flash Point: 356 °F
    4. Appearance: /flakes
    5. Density: 1,34 g/cm3
    6. Vapor Density: 7 (vs air)
    7. Vapor Pressure: 0.02 mm Hg ( 25 °C)
    8. Refractive Index: 1.5684 (estimate)
    9. Storage Temp.: 2-8°C
    10. Solubility: ethanol: 5%, clear
    11. Explosive Limit: 1.5-8.9%(V)
    12. Water Solubility: REACTS
    13. Sensitive: Moisture Sensitive
    14. BRN: 607796
    15. CAS DataBase Reference: Terephthaloyl chloride(CAS DataBase Reference)
    16. NIST Chemistry Reference: Terephthaloyl chloride(100-20-9)
    17. EPA Substance Registry System: Terephthaloyl chloride(100-20-9)
  • Safety Data

    1. Hazard Codes: C,T
    2. Statements: 34-23-35
    3. Safety Statements: 26-27-36/37/39-45-38-28B
    4. RIDADR: UN 2923 8/PG 3
    5. WGK Germany: 3
    6. RTECS: WZ1797000
    7. TSCA: Yes
    8. HazardClass: 6.1
    9. PackingGroup: II
    10. Hazardous Substances Data: 100-20-9(Hazardous Substances Data)

100-20-9 Usage

Uses

1. Specialty Fibers and Polymers:
Terephthaloyl chloride is used as a monomer for the synthesis of specialty fibers and serves as a raw material for polymers such as polyamides and polyesters. It is also used alongside isophthaloyl dichloride in similar applications.
2. Dye Manufacture:
In the dye industry, Terephthaloyl chloride is utilized in the production process.
3. Synthetic Fibers, Resins, and Films:
Terephthaloyl chloride is employed in the creation of synthetic fibers, resins, and films due to its chemical properties.
4. UV Absorption:
It is used for its UV absorption properties, making it a valuable component in various applications where protection from ultraviolet radiation is necessary.
5. Pharmaceuticals:
Terephthaloyl chloride finds use in the pharmaceutical industry, likely due to its ability to interact with other compounds and form new substances.
6. Rubber Chemicals:
It is also used in the rubber industry as a chemical additive, potentially for enhancing the properties of rubber products.
7. Cross-linking Agent:
Terephthaloyl chloride acts as a cross-linking agent for polyurethanes and polysulfides, improving the structural integrity and performance of these materials.
8. Performance Polymers and Aramid Fibers:
Used in the production of poly paraphenylene terephthalamide, Terephthaloyl chloride contributes to the creation of performance polymers and aramid fibers. These materials exhibit flame resistance, chemical resistance, temperature stability, light weight, and high strength.
9. Water Scavenger:
Terephthaloyl chloride is an effective water scavenger, used to stabilize isocyanates and urethane prepolymers.
10. Liquid Crystalline Thermosets:
It is involved in the preparation of liquid crystalline thermosets through the thermal cyclotrimerization of dicyanate compounds of ring substituted bis(4-hydroxyphenyl) terepthalates.
11. Chain-Extended Polystyrene:
Terephthaloyl chloride is used in the condensation reaction with difunctional alfa, μ-diaminopolystyrene to produce chain-extended polystyrene containing amide bonds along the polymer backbone.

Preparation

Synthesis of terephthaloyl chloride by thionyl chloride method: terephthalic acid is mixed with thionyl chloride, refluxed at 80℃ for 10-12h, then the thionyl chloride is evaporated, and the resulting crude product is distilled under reduced pressure to obtain the finished product.

Hazard

Skin irritant.

Flammability and Explosibility

Nonflammable

Safety Profile

Moderately toxic by ingestion. Corrosive. Combustible when exposed to heat or flame. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORIDES.

Purification Methods

Crystallise the acid chloride from dry hexane. [Beilstein 9 IV 3318.]

Check Digit Verification of cas no

The CAS Registry Mumber 100-20-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 0 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 100-20:
(5*1)+(4*0)+(3*0)+(2*2)+(1*0)=9
9 % 10 = 9
So 100-20-9 is a valid CAS Registry Number.
InChI:InChI=1/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H

100-20-9 Well-known Company Product Price

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  • CAS number
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  • Detail
  • Alfa Aesar

  • (A11224)  Terephthaloyl chloride, 99%   

  • 100-20-9

  • 250g

  • 327.0CNY

  • Detail
  • Alfa Aesar

  • (A11224)  Terephthaloyl chloride, 99%   

  • 100-20-9

  • 1000g

  • 833.0CNY

  • Detail
  • Aldrich

  • (120871)  Terephthaloylchloride  ≥99%, flakes

  • 100-20-9

  • 120871-5G

  • 288.99CNY

  • Detail
  • Aldrich

  • (120871)  Terephthaloylchloride  ≥99%, flakes

  • 100-20-9

  • 120871-250G

  • 486.72CNY

  • Detail
  • Aldrich

  • (120871)  Terephthaloylchloride  ≥99%, flakes

  • 100-20-9

  • 120871-1KG

  • 1,310.40CNY

  • Detail

100-20-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name Terephthaloyl Chloride

1.2 Other means of identification

Product number -
Other names Terephthaloyl Dichloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:100-20-9 SDS

100-20-9Synthetic route

terephthalic acid
100-21-0

terephthalic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With thionyl chloride for 2h; Reflux;100%
With aluminum (III) chloride; Methyltrichlorosilane In tetrachloromethane at 70℃; for 13h; Temperature; Reagent/catalyst;99.13%
With thionyl chloride for 5h; Reflux;98%
phosgene
75-44-5

phosgene

terephthalic acid
100-21-0

terephthalic acid

N,N-dimethyl-aniline
121-69-7

N,N-dimethyl-aniline

A

1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
In dichloromethaneA n/a
B 90.2%
carbon monoxide
201230-82-2

carbon monoxide

4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With bis(tri-t-butylphosphine)palladium(0); benzyltriphenylphosphonium chloride In toluene at 110℃; under 38002.6 Torr; for 48h; Glovebox; Autoclave; Inert atmosphere;88%
para-xylene
106-42-3

para-xylene

A

4-methyl-benzoyl chloride
874-60-2

4-methyl-benzoyl chloride

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
Stage #1: para-xylene With 5,10,15,20-tetrakis(4-methylphenyl)porphyrinatocopper(II); C40H32MnN8; oxygen at 180℃; under 2 Torr;
Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;
A 59.4%
B 9.3%
Stage #1: para-xylene With 5,10,15,20-tetrakis(4-methylphenyl)porphyrinatocopper(II); C36H24MnN8; oxygen; cobalt(II) diacetate tetrahydrate at 180℃; under 15001.5 Torr;
Stage #2: With thionyl chloride Reagent/catalyst; Temperature; Pressure;
A 27.1%
B 37.1%
maleic anhydride
108-31-6

maleic anhydride

1,4-bis(trichloromethyl)benzene
68-36-0

1,4-bis(trichloromethyl)benzene

(E)-3-Ureido-but-2-enoic acid ethyl ester
5435-44-9, 22243-66-9

(E)-3-Ureido-but-2-enoic acid ethyl ester

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
at 140℃;
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With chlorine at 220℃;
With chlorine In benzene for 12h; Solvent; UV-irradiation;
1,4-bis(trichloromethyl)benzene
68-36-0

1,4-bis(trichloromethyl)benzene

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With titanium(IV) oxide
With maleic acid; zinc(II) chloride
With water; iron(III) chloride at 125 - 140℃;
With aluminium trichloride; water at 125 - 140℃;
at 125℃; for 1h; Temperature;
4-trichloromethylbenzoyl chloride
14815-86-2

4-trichloromethylbenzoyl chloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With water; iron(III) chloride at 120 - 130℃;
p-Toluic acid
99-94-5

p-Toluic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With tetrachloromethane; chlorine at 250℃;
terephthalic acid
100-21-0

terephthalic acid

Benzotrichlorid
98-07-7

Benzotrichlorid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalic acid
100-21-0

terephthalic acid

acetyl chloride
75-36-5

acetyl chloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
at 130℃;
terephthalic acid
100-21-0

terephthalic acid

acetyl chloride
75-36-5

acetyl chloride

A

terephthaloyl chloride
18708-46-8

terephthaloyl chloride

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
at 130℃;
at 130℃;
terephthalic acid
100-21-0

terephthalic acid

1,4-bis(trichloromethyl)benzene
68-36-0

1,4-bis(trichloromethyl)benzene

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
iron(III) chloride In chlorobenzene at 115℃; Rate constant; Kinetics; Mechanism; activation energy, reaction order;
terephthaloyl chloride
18708-46-8

terephthaloyl chloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With thionyl chloride; N,N-dimethyl-formamide at 40℃; Kinetics; Thermodynamic data; 50, 60 deg C, E(excit.), lg A, -ΔS(excit.) at 313 K;
p-phenylenebis(chlorodiazirine)

p-phenylenebis(chlorodiazirine)

A

1,4-bis-chlorocarbonyloxy-benzene
1885-20-7

1,4-bis-chlorocarbonyloxy-benzene

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With oxygen In solid matrix at -263.2℃; Irradiation; var. conc. of O2;
ethanol
64-17-5

ethanol

terephthalic acid
100-21-0

terephthalic acid

A

diethyl-4,4-(1,3,4-oxadiazole-2,5-diyl)dibenzoate
109865-79-4

diethyl-4,4-(1,3,4-oxadiazole-2,5-diyl)dibenzoate

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
Yield given. Multistep reaction;A n/a
B 4.0 g
terephthalic acid bis(trimethylsilyl) ester
4147-84-6

terephthalic acid bis(trimethylsilyl) ester

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane 1.) 0 deg C, 1 h, 2.) RT, 1 h;
terephthalic acid
100-21-0

terephthalic acid

2.4-dichloro-trichloromethyl-benzene

2.4-dichloro-trichloromethyl-benzene

terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalic acid
100-21-0

terephthalic acid

phosphorus pentachloride
10026-13-8, 874483-75-7

phosphorus pentachloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalic acid
100-21-0

terephthalic acid

2-chloro-1,3-dimethylimidazolinium chloride
37091-73-9

2-chloro-1,3-dimethylimidazolinium chloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
In toluene
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

methyl terephthalate chloride

methyl terephthalate chloride

Triphenylphosphine oxide
791-28-6

Triphenylphosphine oxide

terephthaloyl chloride
100-20-9

terephthaloyl chloride

phosgene
75-44-5

phosgene

terephthalic acid
100-21-0

terephthalic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With pyridine In dichloromethane
1,4-benzenedicarboxylic acid dimethyl ester
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

1,4-bis(trichloromethyl)benzene
68-36-0

1,4-bis(trichloromethyl)benzene

benzamide
55-21-0

benzamide

terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalaldehyde,
623-27-8

terephthalaldehyde,

A

4-formylbenzoyl chloride
16173-52-7

4-formylbenzoyl chloride

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With chlorine at 90℃; for 3.16667h; Product distribution / selectivity;
terephthalaldehyde,
623-27-8

terephthalaldehyde,

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With chlorine at 90℃; for 3.45h; Product distribution / selectivity; visible light irradiation;
Isophthalaldehyde
626-19-7

Isophthalaldehyde

terephthalaldehyde,
623-27-8

terephthalaldehyde,

A

terephthaloyl chloride
100-20-9

terephthaloyl chloride

B

benzene-1,3-dicarbonyl dichloride
99-63-8

benzene-1,3-dicarbonyl dichloride

Conditions
ConditionsYield
With chlorine at 43℃; for 0.5h; Product distribution / selectivity; visible light irradiation;
disodium terephthalate
10028-70-3

disodium terephthalate

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With thionyl chloride for 0.0833333h;
4-iodobenzoic acid chloride
1711-02-0

4-iodobenzoic acid chloride

A

para-diiodobenzene
624-38-4

para-diiodobenzene

B

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 100℃; for 12h; Mechanism;A 11 %Chromat.
B 7 %Chromat.
terephthaloyl chloride
100-20-9

terephthaloyl chloride

benzylamine
100-46-9

benzylamine

N1,N4-dibenzylterephthalamide
15771-25-2

N1,N4-dibenzylterephthalamide

Conditions
ConditionsYield
With triethylamine In dichloromethane100%
(2S,3S,4S,5S)-4-(tert-butyldimethylsiloxy)-2,5-bis[(tert-butyldimethylsiloxy)methyl]-6,6-dimethyltetrahydro-2H-pyran-3-amine

(2S,3S,4S,5S)-4-(tert-butyldimethylsiloxy)-2,5-bis[(tert-butyldimethylsiloxy)methyl]-6,6-dimethyltetrahydro-2H-pyran-3-amine

terephthaloyl chloride
100-20-9

terephthaloyl chloride

C62H124N2O10Si6

C62H124N2O10Si6

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 21h; Schotten-Baumann Reaction; Inert atmosphere;100%
anthranilic acid
118-92-3

anthranilic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

cyassorb 3638
18600-59-4

cyassorb 3638

Conditions
ConditionsYield
Stage #1: anthranilic acid; terephthaloyl chloride In N,N-dimethyl acetamide at 0 - 5℃; for 1h; Cooling with ice-methanol;
Stage #2: With acetic anhydride In N,N-dimethyl acetamide; toluene for 1.5h; Product distribution / selectivity; Heating / reflux;
99%
Stage #1: anthranilic acid; terephthaloyl chloride In 1-methyl-pyrrolidin-2-one at 3 - 8℃; for 2h; Cooling with ice;
Stage #2: With acetic anhydride In 1-methyl-pyrrolidin-2-one at 108 - 116℃; for 2h; Product distribution / selectivity;
96%
Stage #1: anthranilic acid; terephthaloyl chloride In sulfolane at 6 - 8℃; for 2h; Cooling with ice;
Stage #2: With acetic anhydride In 1,4-dioxane; sulfolane for 2h; Product distribution / selectivity; Heating / reflux;
96%
In pyridine
2-isopropenylaniline
52562-19-3

2-isopropenylaniline

terephthaloyl chloride
100-20-9

terephthaloyl chloride

N,N'-Bis-(2-isopropenyl-phenyl)-terephthalamide
148336-18-9

N,N'-Bis-(2-isopropenyl-phenyl)-terephthalamide

Conditions
ConditionsYield
With pyridine at 0℃; for 2h;99%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

10-(4,5-dimethyl-1,3-dithiol-2-ylidene)-9,10-dihydro-9-(4-hydroxymethyl-5-methyl-1,3-dithiol-2-ylidene)anthracene
336196-13-5

10-(4,5-dimethyl-1,3-dithiol-2-ylidene)-9,10-dihydro-9-(4-hydroxymethyl-5-methyl-1,3-dithiol-2-ylidene)anthracene

terephthalic acid bis-{2-[10-(4,5-dimethyl-[1,3]dithiol-2-ylidene)-10H-anthracen-9-ylidene]-5-methyl-[1,3]dithiol-4-ylmethyl} ester

terephthalic acid bis-{2-[10-(4,5-dimethyl-[1,3]dithiol-2-ylidene)-10H-anthracen-9-ylidene]-5-methyl-[1,3]dithiol-4-ylmethyl} ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃;99%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

4-hydroxymethyldibenzo-24-crown-8 ether
221002-03-5

4-hydroxymethyldibenzo-24-crown-8 ether

terephthalic acid bis-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.012,17]dotriaconta-1(32),12,14,16,28,30-hexaen-14-ylmethyl) ester

terephthalic acid bis-(2,5,8,11,18,21,24,27-octaoxa-tricyclo[26.4.0.012,17]dotriaconta-1(32),12,14,16,28,30-hexaen-14-ylmethyl) ester

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃; for 0.25h;99%
1-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)piperazine

1-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)piperazine

terephthaloyl chloride
100-20-9

terephthaloyl chloride

[4-[4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)piperazine-1-carbonyl]phenyl]-[4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)piperazin-1-yl]methanone

[4-[4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)piperazine-1-carbonyl]phenyl]-[4-(1,1,2,2,3,3,4,4,4-nonafluorobutylsulfonyl)piperazin-1-yl]methanone

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;99%
N-(tert-butoxycarbonyl)-1,4-phenylenediamine
71026-66-9

N-(tert-butoxycarbonyl)-1,4-phenylenediamine

terephthaloyl chloride
100-20-9

terephthaloyl chloride

di-tert-butyl ((terephthaloylbis(azanediyl))bis(4,1-phenylene))dicarbamate

di-tert-butyl ((terephthaloylbis(azanediyl))bis(4,1-phenylene))dicarbamate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 20℃; for 15h;99%
L-valine methylester hydrochloride
6306-52-1

L-valine methylester hydrochloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

C20H28N2O6

C20H28N2O6

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;98.5%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalaldehyde,
623-27-8

terephthalaldehyde,

Conditions
ConditionsYield
With sodium tris(tert-butoxo)aluminium hydride In tetrahydrofuran; diethylene glycol dimethyl ether at -78℃; for 3h;98%
With tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) In benzene for 0.166667h; Ambient temperature;87%
With tri-n-butyl-tin hydride In 1-methyl-pyrrolidin-2-one at 20℃; Inert atmosphere;86%
methyl thiocyanate
556-64-9

methyl thiocyanate

terephthaloyl chloride
100-20-9

terephthaloyl chloride

2,2'-(1,4-Phenylen)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)
125077-76-1

2,2'-(1,4-Phenylen)bis<4,6-bis(methylthio)-1,3,5-oxadiazinium>-dihexachloroantimonat(V)

Conditions
ConditionsYield
With antimonypentachloride In tetrachloromethane for 2h; Ambient temperature;98%
sebacoyl chloride
111-19-3

sebacoyl chloride

2,5-dimethyl-2,5-dihydroperoxyhexane
3025-88-5

2,5-dimethyl-2,5-dihydroperoxyhexane

terephthaloyl chloride
100-20-9

terephthaloyl chloride

4-(4-{4-[4-(9-{4-[9-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-nonanoylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-nonanoylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid

4-(4-{4-[4-(9-{4-[9-(4-Hydroperoxy-1,1,4-trimethyl-pentylperoxycarbonyl)-nonanoylperoxy]-1,1,4-trimethyl-pentylperoxycarbonyl}-nonanoylperoxy)-1,1,4-trimethyl-pentylperoxycarbonyl]-benzoylperoxy}-1,1,4-trimethyl-pentylperoxycarbonyl)-benzoic acid

Conditions
ConditionsYield
With pyridine In dichloromethane at 20℃; for 1.5h;98%
N-methyl-hydrazinecarbodithioic acid methyl ester
20184-94-5

N-methyl-hydrazinecarbodithioic acid methyl ester

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Dimethyl 3,3'-terephthaloylbis-(2-methyldithiocarbazate)
134897-08-8

Dimethyl 3,3'-terephthaloylbis-(2-methyldithiocarbazate)

Conditions
ConditionsYield
In toluene for 4h; Heating;98%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

4-<<(S)-6-methyloctyl>oxy>phenol
114243-83-3

4-<<(S)-6-methyloctyl>oxy>phenol

4-<<(S)-6-methyloctyl>oxy>phenyl 4-(chloroformyl)benzoate
115607-32-4

4-<<(S)-6-methyloctyl>oxy>phenyl 4-(chloroformyl)benzoate

Conditions
ConditionsYield
With toluene Ambient temperature;98%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

1,1'-bi-2-naphthol
602-09-5

1,1'-bi-2-naphthol

Polymer, Mw 0.9E4; Monomer(s): terephthaloyl chloride; (R)-1,1\-bi-2-naphthol

Polymer, Mw 0.9E4; Monomer(s): terephthaloyl chloride; (R)-1,1\-bi-2-naphthol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran under 12 Torr; Heating;98%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

1,1'-bi-2-naphthol
602-09-5

1,1'-bi-2-naphthol

Polymer, Mw 1.0E4; Monomer(s): terephthaloyl chloride; (S)-1,1\-bi-2-naphthol

Polymer, Mw 1.0E4; Monomer(s): terephthaloyl chloride; (S)-1,1\-bi-2-naphthol

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran under 12 Torr; Heating;98%
4,4'-bis(phenoxy)benzophenone
14984-21-5

4,4'-bis(phenoxy)benzophenone

terephthaloyl chloride
100-20-9

terephthaloyl chloride

trimellitic anhydride acid chloride
1204-28-0

trimellitic anhydride acid chloride

polymer, ratio of trimellitic anhydride acid chloride/(terephthaloyl chloride + trimellitic anhydride acid chloride) = 30 mol percent; monomer(s): 4,4\-diphenoxybenzophenone; terephthaloyl chloride; trimellitic anhydride acid chloride

polymer, ratio of trimellitic anhydride acid chloride/(terephthaloyl chloride + trimellitic anhydride acid chloride) = 30 mol percent; monomer(s): 4,4\-diphenoxybenzophenone; terephthaloyl chloride; trimellitic anhydride acid chloride

Conditions
ConditionsYield
With aluminium trichloride In 1,2-dichloro-ethane Friedel-Crafts copolycondensation;98%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

1-[(2-methyl-5-methylenehydroxy-3-thienyl)]-2-[(2-methyl-5-methylenehydroxy-3-thienyl)]perfluorocyclopentene
216864-70-9

1-[(2-methyl-5-methylenehydroxy-3-thienyl)]-2-[(2-methyl-5-methylenehydroxy-3-thienyl)]perfluorocyclopentene

Reaxys ID: 11385926

Reaxys ID: 11385926

Conditions
ConditionsYield
With pyridine In 1,1-dichloroethane at 40℃; for 2h;98%
2-Amino-5-methylbenzoic acid
2941-78-8

2-Amino-5-methylbenzoic acid

terephthaloyl chloride
100-20-9

terephthaloyl chloride

C24H16N2O4
163005-38-7

C24H16N2O4

Conditions
ConditionsYield
Stage #1: 2-Amino-5-methylbenzoic acid; terephthaloyl chloride In N,N-dimethyl acetamide at -3 - 4℃; for 2h; Cooling with ice-methanol;
Stage #2: With acetic anhydride In N,N-dimethyl acetamide; toluene for 1.5h; Product distribution / selectivity; Heating / reflux;
98%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

3-aminophenylboronic acid pinacolate
210907-84-9

3-aminophenylboronic acid pinacolate

N1,N4-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)terephthalamide

N1,N4-bis(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)terephthalamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 4 - 20℃; for 18h;98%
isopropylamine
75-31-0

isopropylamine

terephthaloyl chloride
100-20-9

terephthaloyl chloride

N,N'-bis(isopropyl)-1,4-benzenedicarboxamide
15208-70-5

N,N'-bis(isopropyl)-1,4-benzenedicarboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;98%
With triethylamine; lithium chloride In tetrahydrofuran at 0℃; for 12h; Inert atmosphere; Reflux;2.4 g
L-valine methyl ester
4070-48-8

L-valine methyl ester

terephthaloyl chloride
100-20-9

terephthaloyl chloride

dimethyl 2,2′-(terephthaloylbis(azanediyl))bis(3-methylbutanoate)

dimethyl 2,2′-(terephthaloylbis(azanediyl))bis(3-methylbutanoate)

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;98%
D-Valine methyl ester hydrochloride
7146-15-8

D-Valine methyl ester hydrochloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

C20H28N2O6

C20H28N2O6

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;97.5%
aniline
62-53-3

aniline

terephthaloyl chloride
100-20-9

terephthaloyl chloride

N,N'-diphenylterephthalamide
7154-31-6

N,N'-diphenylterephthalamide

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.716667h;97%
With triethylamine In tetrahydrofuran at 20℃; for 18h;92%
With potassium carbonate In dichloromethane at 20℃; for 4h;73.2%
propan-1-ol
71-23-8

propan-1-ol

terephthaloyl chloride
100-20-9

terephthaloyl chloride

terephthalic acid dipropyl ester
1962-74-9

terephthalic acid dipropyl ester

Conditions
ConditionsYield
In toluene97%
methyl 4,6-O-benzylidene-α-D-allopyranoside
79549-74-9

methyl 4,6-O-benzylidene-α-D-allopyranoside

terephthaloyl chloride
100-20-9

terephthaloyl chloride

Terephthalic acid 1-((2S,4aS,6R,7S,8S,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester 4-((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester

Terephthalic acid 1-((2S,4aS,6R,7S,8S,8aR)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester 4-((2R,4aR,6S,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl) ester

Conditions
ConditionsYield
With di(n-butyl)tin oxide; triethylamine In toluene at 22℃; for 0.33h;97%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

N-((R)-1-phenyl-ethyl)-N-propargylamine
808770-44-7

N-((R)-1-phenyl-ethyl)-N-propargylamine

N,N'-bis-(1-phenyl-ethyl)-N,N'-di-prop-2-ynyl-terephthalamide
808770-46-9

N,N'-bis-(1-phenyl-ethyl)-N,N'-di-prop-2-ynyl-terephthalamide

Conditions
ConditionsYield
With triethylamine In dichloromethane97%
terephthaloyl chloride
100-20-9

terephthaloyl chloride

5-chloroanthranilic acid
635-21-2

5-chloroanthranilic acid

C22H10Cl2N2O4
163005-37-6

C22H10Cl2N2O4

Conditions
ConditionsYield
Stage #1: terephthaloyl chloride; 5-chloroanthranilic acid In N,N-dimethyl acetamide at 4 - 11℃; for 4h; Cooling with ice;
Stage #2: With acetic anhydride In N,N-dimethyl acetamide at 105 - 126℃; for 2h;
97%
4,6-diaminoresorcin dihydrochloride
16523-31-2

4,6-diaminoresorcin dihydrochloride

terephthaloyl chloride
100-20-9

terephthaloyl chloride

2-(p-chloroformylphenyl)-5-amino-6-hydroxyl benzoxazole

2-(p-chloroformylphenyl)-5-amino-6-hydroxyl benzoxazole

Conditions
ConditionsYield
Stage #1: 4,6-diaminoresorcin dihydrochloride at 70℃; for 2h; Inert atmosphere; Ionic liquid;
Stage #2: terephthaloyl chloride at 110℃; for 12h; Time; Temperature; Inert atmosphere; Ionic liquid;
97%

100-20-9Relevant articles and documents

Incorporating Pendent Fullerenes with High Refractive Index Backbones: A Conjunction Effect Method for High Refractive Index Polymers

Chen, Shuang,Chen, Dongxue,Lu, Min,Zhang, Xin,Li, He,Zhang, Xiaoyan,Yang, Xiaoming,Li, Xiaohong,Tu, Yingfeng,Li, Christopher Y.

, p. 8480 - 8488 (2015)

To achieve high refractive index polymers (HRIPs), we report here the design and synthesis of four fullerene polyesters (P1-P4), based on the conjunction effect from the high refractive index polyester backbones and pendent fullerene side chains. At sodiu

C-I···π Halogen Bonding Driven Supramolecular Helix of Bilateral N-Amidothioureas Bearing β-Turns

Cao, Jinlian,Yan, Xiaosheng,He, Wenbin,Li, Xiaorui,Li, Zhao,Mo, Yirong,Liu, Maili,Jiang, Yun-Bao

, p. 6605 - 6610 (2017)

We report the first example of C-I···π halogen bonding driven supramolecular helix in highly dilute solution of micromolar concentration, using alanine based bilateral I-substituted N-amidothioureas that contain helical fragments, the β-turn structures. T

Synthesis, thermal, and photocrosslinking studies of thermotropic liquid crystalline poly(benzylidene-ether)esters containing α,β-unsaturated ketone moiety in the main chain

Muthusamy, Athianna,Balaji, Krishnasamy,Murugavel, Salem Chandrasekaran

, p. 1707 - 1715 (2013)

A series of poly(benzylidene-ether)esters containing a photoreactive benzylidene chromophore in the main chain were synthesized from 2,6-bis(4-hydroxy-3-methoxybenzylidene)cyclohexanone (BHMBCH) with various aliphatic and aromatic diacid chlorides by an interfacial polycondensation technique. The intrinsic viscosity of the synthesized homo and copolymers determined by Ubbelohde viscometer was found to be 0.12 to 0.17 dL/g. The molecular structure of the monomer and polymers was confirmed by FT-IR, 1H NMR, and 13C NMR spectral analyses. These polymers were studied for their thermal stability and photochemical properties. Thermal properties were evaluated by thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). It was found that the polymers were stable up to 280 °C and start degrading thereafter. Increase in acid methylene spacer length decreased the thermal stability. The self-extinguishing property of the synthesized polymers was studied by calculating the limiting oxygen index (LOI) value using a Van Krevelen's equation. The influence of the length of methylene spacer on phase transition was investigated using DSC and odd-even effect has been observed. Hot-stage optical polarizing microscopic (HOPM) study showed that most of the polymers exhibited birefringence and opalescence properties. The photolysis of liquid crystalline poly(benzylidene-ether)esters revealed that α,β-unsaturated ketone moiety in the main chain dimerises through 2π + 2π cycloaddition reaction to form a cyclobutane derivative and leads to crosslinking.

Exploiting Peptidomimetics to Synthesize Compounds That Activate Ryanodine Receptor Calcium Release Channels

Robinson, Ken,Easton, Christopher J.,Dulhunty, Angela F.,Casarotto, Marco G.

, p. 1957 - 1971 (2018)

Ryanodine receptor (RyR) Ca2+-release channels are essential for contraction in skeletal and cardiac muscle and are prime targets for modification of contraction in disorders that affect either the skeletal or heart musculature. We designed and synthesized a number of compounds with structures based on a naturally occurring peptide (A peptides) that modifies the activity of RyRs. In total, 34 compounds belonging to eight different classes were prepared. The compounds were screened for their ability to enhance Ca2+ release from isolated cardiac sarcoplasmic reticulum (SR) vesicles, with 25 displaying enhanced Ca2+ release. Competition studies with the parent peptides indicated that the synthetic compounds act at a competing site. The activity of the most effective of the compounds, BIT 180, was further explored using Ca2+ release from skeletal SR vesicles and contraction in intact skeletal muscle fibers. The compounds did not alter tension in intact fibers, indicating that (as expected) they are not membrane permeable, but importantly, that they are not toxic to the intact cells. Proof in principal that the compounds would be effective in intact muscle fibers if rendered membrane permeable was obtained with a structurally related membrane-permeable scorpion toxin (imperatoxin A), which was found to enhance contraction.

Infrared and Raman spectra of terephthalonitrile and terephthalonitrile-15N2. Force field for out-of-plane vibrations

Arenas, J. F.,Marcos, J. I.,Ramirez, F. J.

, p. 1045 - 1052 (1988)

A general assignment of the vibrational spectra of terephthalonitrile and terephthalonitrile-15N2 is proposed on the basis of their infrared and Raman spectra.The relevant symmetry is found to be D2h.The force field for the out-of-plane vibrati

Phosphazenium chloride catalysts immobilized on SBA-15 mesoporous material and silica gel: New exceptionally active catalysts for the chlorination of organic acids

Kim, Keun-Sik,Kim, Jong-Ho,Seo, Gon

, p. 372 - 373 (2003)

Novel reusable phosphazenium chloride catalysts immobilized on SBA-15 mesoporous material and silica gel show exceptional activities and selectivities even in the continuous chlorination reaction of organic acids with thionyl chloride or phosgene.

Effect of regioisomerism on the self-assembly and photophysical behavior of 1,3,4-thiadiazole-based polycatenars

Pathak, Suraj Kumar,Nath, Subrata,Gupta, Ravindra Kumar,Rao, D. S. Shankar,Prasad, S. Krishna,Achalkumar, Ammathnadu S.

, p. 8166 - 8182 (2015)

A new class of polycatenars, where the central benzene ring is connected to two arms derived from substituted 1,3,4-thiadiazoles at the 1,3- and 1,4-positions, was synthesized and characterized. These thiadiazole-based molecules are promising as they stabilize columnar phases over a wide temperature range, in comparison to their oxadiazole analogues. The para-substituted polycatenars exhibited a columnar hexagonal and/or a columnar oblique phase, while the meta-substituted polycatenars exhibited solely a columnar oblique phase. The para-substituted polycatenars exhibited green emission, while the meta-substituted polycatenars exhibited blue emission in solution and film states. Stabilization of a broad range columnar phase and luminescence in the solid state make these new compounds promising from the viewpoint of applications in emissive displays. The self-assembly and luminescence of these regioisomers was greatly influenced by the molecular structure.

Aromatic Esters, Carbinols, and Derivatives Thereof with Perfluorohexyl Residues as Alternatives to Perfluoroalkanecarboxylic and -sulfonic Acids

Alpers, Torben,Muesmann, Thomas W. T.,Temme, Oliver,Christoffers, Jens

, p. 609 - 617 (2017)

Four perfluorohexyl carbinols have been prepared from the corresponding Grignard reagent and benzaldehyde, terephthalaldehyde, isophthalaldehyde, and trimesaldehyde. The corresponding secondary alcohols were then transformed by alkylation and acylation reactions to form a total of 14 ethers (methyl, ethyl, propyl, and n-hexyl ethers) and esters (acetyl and 2-ethylhexanoyl), respectively. Furthermore, 11 perfluoroalkyl carboxylates were prepared from aromatic, heteroaromatic, and aliphatic mono-, di-, tri-, and tetracarboxylic acids and tridecafluorooctanol. The wettability of all 29 materials was investigated by the water contact angle measurements of thin films on glass surfaces. In up to six cases, contact angles greater than 130° were observed, which indicates that the products might be suitable candidates for the impregnation of surfaces. With their relatively short perfluoroalkyl side-chains and therefore low bioaccumulativity, the target compounds might be beneficial alternatives to established products.

Photo-on-Demand Synthesis of Vilsmeier Reagents with Chloroform and Their Applications to One-Pot Organic Syntheses

Liang, Fengying,Eda, Kazuo,Okazoe, Takashi,Wada, Akihiro,Mori, Nobuaki,Konishi, Katsuhiko,Tsuda, Akihiko

, p. 6504 - 6517 (2021)

The Vilsmeier reagent (VR), first reported a century ago, is a versatile reagent in a variety of organic reactions. It is used extensively in formylation reactions. However, the synthesis of VR generally requires highly toxic and corrosive reagents such as POCl3, SOCl2, or COCl2. In this study, we found that VR is readily obtained from a CHCl3 solution containing N,N-dimethylformamide or N,N-dimethylacetamide upon photo-irradiation under O2 bubbling. The corresponding Vilsmeier reagents were obtained in high yields with the generation of gaseous HCl and CO2 as byproducts to allow their isolations as crystalline solid products amenable to analysis by X-ray crystallography. With the advantage of using CHCl3, which bifunctionally serves as a reactant and a solvent, this photo-on-demand VR synthesis is available for one-pot syntheses of aldehydes, acid chlorides, formates, ketones, esters, and amides.

Synthesis of poly β ketoesters via double acylketene trapping

Palma, Aniello,Serginson, James M.,Barrett, Anthony G.M.

, p. 674 - 676 (2015)

The synthesis and characterization of polymeric β ketoesters is herein reported. These polymers were prepared by allowing highly electrophilic acylketenes, generated in situ via thermolysis of stable 6-substituted-2,2-dimethyl-4H-1,3-dioxin-4-ones, to rea

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