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Terephthaloyl chloride

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Name

Terephthaloyl chloride

EINECS 202-829-5
CAS No. 100-20-9 Density 1.427 g/cm3
PSA 34.14000 LogP 2.44460
Solubility ethanol: 5%, clear Melting Point 79-81 °C(lit.)
Formula C8H4Cl2O2 Boiling Point 266 °C at 760 mmHg
Molecular Weight 203.025 Flash Point 143.1 °C
Transport Information UN 2923 8/PG 3 Appearance white crystalline flakes
Safety 26-27-36/37/39-45-38-28B Risk Codes 34-23
Molecular Structure Molecular Structure of 100-20-9 (Terephthaloyl chloride) Hazard Symbols CorrosiveC,ToxicT
Synonyms

Terephthaloylchloride (8CI);1,4-Benzenedicarbonyl chloride;1,4-Bis(chlorocarbonyl)benzene;1,4-Di(chlorocarbonyl)benzene;Benzene 1,4-dicarboxylic acid dichloride;NSC41885;Terephthalic acid chloride;Terephthalic acid dichloride;Terephthalicdichloride;Terephthaloyl dichloride;p-Phenylenedicarbonyl dichloride;p-Phthaloyl chloride;p-Phthaloyl dichloride;

Article Data 133

Terephthaloyl chloride Synthetic route

100-21-0

terephthalic acid

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%
75-44-5

phosgene

100-21-0

terephthalic acid

121-69-7

N,N-dimethyl-aniline

A

120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

B

100-20-9

terephthaloyl chloride

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

carbon monoxide

1711-02-0

4-iodobenzoic acid 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%
106-42-3

para-xylene

A

874-60-2

4-methyl-benzoyl chloride

B

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%
108-31-6

maleic anhydride

68-36-0

1,4-bis(trichloromethyl)benzene

5435-44-9, 22243-66-9

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

100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
at 140℃;
120-61-6

1,4-benzenedicarboxylic acid dimethyl ester

100-20-9

terephthaloyl chloride

Conditions
ConditionsYield
With chlorine at 220℃;
With chlorine In benzene for 12h; Solvent; UV-irradiation;
68-36-0

1,4-bis(trichloromethyl)benzene

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;
14815-86-2

4-trichloromethylbenzoyl chloride

100-20-9

terephthaloyl chloride

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

p-Toluic acid

100-20-9

terephthaloyl chloride

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

terephthalic acid

98-07-7

Benzotrichlorid

100-20-9

terephthaloyl chloride

Terephthaloyl chloride Consensus Reports

Reported in EPA TSCA Inventory.

Terephthaloyl chloride Specification

The Terephthaloyl dichloride with cas registry number of 100-20-9 can be classified in several categories which include Functional Materials; Reagent for High-Performance Polymer Research; Acid Halides; Carbonyl Compounds; Organic Building Blocks. It has an appearance of white crystalline flakes with EINECS registry number of 202-829-5. It also has other registry numbers which are 106158-15-0, 108454-76-8, 188665-55-6. This chemical has some superlist names such as 1,4-Benzenedicarbonyl dichloride and Terephthaloyl chloride. Both its systematic name and IUPAC name are the same which is called benzene-1,4-dicarbonyl dichloride.

The Physical properties about this chemical are: (1)ACD/LogP: 2.63; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 2.63; (4)ACD/LogD (pH 7.4): 2.63; (5)ACD/BCF (pH 5.5): 58.69; (6)ACD/BCF (pH 7.4): 58.69; (7)ACD/KOC (pH 5.5): 642.01; (8)ACD/KOC (pH 7.4): 642.01; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.571; (13)Molar Refractivity: 46.74 cm3; (14)Molar Volume: 142.2 cm3; (15)Surface Tension: 48.2 dyne/cm; (16)Density: 1.427 g/cm3; (17)Flash Point: 143.1 °C; (18)Enthalpy of Vaporization: 50.4 kJ/mol; (19)Boiling Point: 266 °C at 760 mmHg; (20)Vapour Pressure: 0.00887 mmHg at 25°C.

When you are using this chemical, please be cautious about it as the following:
This chemical is sensitive to moisture.It causes burns and toxic by inhalation. Therefore wear suitable protective clothing, gloves and eye/face protection if you are using it. In case of insufficient ventilation, wear suitable respiratory equipment. After using it, take off immediately all contaminated clothing. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If you feel unwell, seek medical advice immediately.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(Cl)c1ccc(C(Cl)=O)cc1;
(2)InChI: InChI=1/C8H4Cl2O2/c9-7(11)5-1-2-6(4-3-5)8(10)12/h1-4H;
(3)InChIKey: LXEJRKJRKIFVNY-UHFFFAOYAY

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 oral 2140mg/kg (2140mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(12), Pg. 35, 1984.
rabbit LD skin > 200mg/kg (200mg/kg)   National Technical Information Service. Vol. OTS0533726,
rabbit LD50 oral 950mg/kg (950mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(12), Pg. 35, 1984.
rat LC50 inhalation 700mg/m3/4H (700mg/m3) SENSE ORGANS AND SPECIAL SENSES: LACRIMATION: EYE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
National Technical Information Service. Vol. OTS0533726,
rat LD50 oral 2500mg/kg (2500mg/kg)   "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 475, 1969.

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