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Adipoyl chloride

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Name

Adipoyl chloride

EINECS 203-876-4
CAS No. 111-50-2 Density 1.265 g/cm3
PSA 34.14000 LogP 2.07760
Solubility Reacts with water Melting Point 262-264 °C
Formula C6H8Cl2O2 Boiling Point 273.9 °C at 760 mmHg
Molecular Weight 183.034 Flash Point 99.4 °C
Transport Information UN 3265 8/PG 2 Appearance colourless to dark brown liquid with a pungent odour
Safety 26-36/37/39-45-8 Risk Codes 34-29-20/21/22-14
Molecular Structure Molecular Structure of 111-50-2 (Adipoyl chloride) Hazard Symbols CorrosiveC
Synonyms

Hexanedioyl dichloride;Adipoylchloride (6CI,8CI);1,4-Bis(chlorocarbonyl)butane;Adipic acid dichloride;Adipoyl dichloride;Adipyl chloride;Adipyl dichloride;Hexanedioic aciddichloride;Hexanedioic dichloride;

Article Data 110

Adipoyl chloride Synthetic route

124-04-9

Adipic acid

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
With phosgene; N,N-dimethyl-formamide In toluene at 50 - 55℃;98.2%
With oxalyl dichloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 4h;91%
With thionyl chloride at 120℃; for 4h;81.2%
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

627-91-8

adipic acid monomethyl ester

A

111-50-2

Adipic acid dichloride

B

118380-06-6

1-methyl 6-succinimidyl adipate

Conditions
ConditionsYield
With triethylamine In thionyl chloride; dichloromethaneA n/a
B 87.5%
With triethylamine In thionyl chloride; dichloromethaneA n/a
B 87.5%
124-04-9

Adipic acid

A

102939-46-8

adipic acid monomethyl ester

B

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
With phosgene; N,N-dimethyl-formamide In toluene at 50 - 55℃; Product distribution / selectivity;A n/a
B 78.3%

3-dimethylamino-5-piperidinophenol

butylene-1,4-di[N-carbonyl-L-alanyl chloride]

A

butylene-1,4-di[N-carbonyl-L-alanyloxy-3-dimethylamino-5-piperidinophenol]

B

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
With sodium hydrogencarbonate In pyridine; chloroformA 65.8%
B n/a
124-04-9

Adipic acid

4885-02-3

Dichloromethyl methyl ether

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
With zinc(II) chloride
32564-25-3

bis(4-nitrophenyl)adipate

A

100-02-7

4-nitro-phenol

B

73430-11-2

mono-p-nitrophenyl adipate

C

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
With water at 25℃; Rate constant; hydrolysis in the presence or absence of human serum albumin in buffered soln.;
111-20-6

1,10-decanedioic acid

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: nitric acid
2: phosphorus pentachloride
View Scheme
110-94-1

1,5-pentanedioic acid

124-04-9

Adipic acid

110-15-6

succinic acid

A

2873-74-7

gloutaric dichloride

B

543-20-4

succinoyl dichloride

C

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
With thionyl chloride at 20℃;
773837-37-9

sodium cyanide

110-56-5

1,4-dichlorobutane

A

1575-61-7

5-Chlorovaleroyl chloride

B

111-50-2

Adipic acid dichloride

Conditions
ConditionsYield
Stage #1: sodium cyanide; 1,4-dichlorobutane With tetrabutylammomium bromide In water at 80 - 85℃; for 6h; Large scale;
Stage #2: With hydrogenchloride In water at 55 - 70℃; for 5h; Large scale;
Stage #3: With thionyl chloride at 20 - 30℃; for 18h; Large scale;
A 422 kg
B 163 kg
111-50-2

Adipic acid dichloride

71-43-2

benzene

3375-38-0

1,4-dibenzoylbutane

Conditions
ConditionsYield
With zinc(II) chloride In dichloromethane at 20℃; for 24h;100%
With aluminium trichloride58%
With aluminum (III) chloride at 50 - 60℃; for 2h;50%

Adipoyl chloride Specification

The Hexanedioyl dichloride, with the CAS registry number 111-50-2 and EINECS registry number 203-876-4, is also called 1,4-Butanedicarbonyl chloride. It belongs to the product category of Industrial/Fine Chemicals. And it should be stored in the refrigerator. The molecular formula of the chemical is C6H8Cl2O2.

The characteristics of Hexanedioyl dichloride are as followings: (1)ACD/LogP: 1.52; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.52; (4)ACD/LogD (pH 7.4): 1.52; (5)ACD/BCF (pH 5.5): 8.48; (6)ACD/BCF (pH 7.4): 8.48; (7)ACD/KOC (pH 5.5): 160.75; (8)ACD/KOC (pH 7.4): 160.75; (9)#H bond acceptors: 2; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 34.14 Å2; (13)Index of Refraction: 1.46; (14)Molar Refractivity: 39.6 cm3; (15)Molar Volume: 144.5 cm3; (16)Polarizability: 15.7×10-24cm3; (17)Surface Tension: 37.5 dyne/cm; (18)Density: 1.265 g/cm3; (19)Flash Point: 99.4 °C; (20)Enthalpy of Vaporization: 51.23 kJ/mol; (21)Boiling Point: 273.9 °C at 760 mmHg; (22)Vapour Pressure: 0.00557 mmHg at 25°C.

Preparation of Hexanedioyl dichloride: This chemical can be prepared by hexanedioic acid. The reaction will need reagent SOCl2. The reaction time is 4 hours with temperature of 120°C, and the yield is about 81.2%. 

Uses of Hexanedioyl dichloride: It can react with 4-methyl-aniline to produce N,N'-di-p-tolyl-adipamide. This reaction will need reagent pyridine. The reaction time is 24 hours with temperature of 20°C, and the yield is about 67%.  

You should be cautious while dealing with this chemical. It reacts violently with water, and will liberates toxic gas. It is also harmful by inhalation, in contact with skin and if swallowed,  and may cause burns. Therefore, you had better take the following instructions: Keep container dry; Wear suitable protective clothing, gloves and eye/face protection; In case of contacting with eyes, rinse immediately with plenty of water and seek medical advice; In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: O=C(Cl)CCCCC(Cl)=O
(2)InChI: InChI=1/C6H8Cl2O2/c7-5(9)3-1-2-4-6(8)10/h1-4H2
(3)InChIKey: PWAXUOGZOSVGBO-UHFFFAOYAI

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