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1,1-Cyclobutanedicarboxylic acid

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Name

1,1-Cyclobutanedicarboxylic acid

EINECS 226-651-2
CAS No. 5445-51-2 Density 1.534 g/cm3
PSA 74.60000 LogP 0.32590
Solubility Soluble in water, ethyl ether, chloroform and benzene Melting Point 158 °C(lit.)
Formula C6H8O4 Boiling Point 366.4 °C at 760 mmHg
Molecular Weight 144.127 Flash Point 189.6 °C
Transport Information UN 3261 8/PG 2 Appearance white fine crystalline powder
Safety 26-36/37/39-45 Risk Codes 34
Molecular Structure Molecular Structure of 5445-51-2 (1,1-Cyclobutanedicarboxylic acid) Hazard Symbols CorrosiveC
Synonyms

1,1-Dicarboxycyclobutane;1-Carboxycyclobutanecarboxylic acid;NSC 22073;Cyclobutane-1,1-dicarboxylic acid;

Article Data 11

1,1-Cyclobutanedicarboxylic acid Synthetic route

109-64-8

1,3-dibromo-propane

105-53-3

diethyl malonate

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 2h; Ambient temperature;23%
28246-87-9

ethyl 1-cyano-1-cyclobutanecarboxylate

A

141-82-2

malonic acid

B

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

Conditions
ConditionsYield
Hydrolysis;
3779-29-1

diethyl cyclobutane-1,1-dicarboxylate

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

Conditions
ConditionsYield
With potassium carbonate
With oxonium
With sodium hydroxide; water at 20℃; for 48h; Hydrolysis;
30491-91-9

1-cyanocyclobutane-1-carboxylic acid

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide
109-64-8

1,3-dibromo-propane

105-53-3

diethyl malonate

A

3721-95-7

Cyclobutanecarboxylic acid

B

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

Conditions
ConditionsYield
With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride for 1h; Ambient temperature; other subst. 1,3-dibromo compounds, other phase transfer catalysts;
With sodium hydroxide; tetrabutyl-ammonium chloride for 1h; Ambient temperature; Yield given. Yields of byproduct given;
300687-20-1

(3-iodo-propyl)-malonic acid diethyl ester

108-88-3

toluene

sodium phenylmalonic acid ester

sodium phenylmalonic acid ester

A

103-82-2

phenylacetic acid

B

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

60-29-7

diethyl ether

300687-20-1

(3-iodo-propyl)-malonic acid diethyl ester

sodium compound of phenylacetonitrile

sodium compound of phenylacetonitrile

A

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

B

2-phenyl-pimelic acid

2-phenyl-pimelic acid

Conditions
ConditionsYield
Hydrolyse mit alkoh. KOH und Decarboxylierung;
7664-93-9

sulfuric acid

3-(1-ethoxycarbonyl-cyclobutyl)-3-amino-2-cyano-acrylic acid ethyl ester

A

141-82-2

malonic acid

B

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

dipotassium cyclobutane-1,1-dicarboxylic acid

Conditions
ConditionsYield
With potassium hydroxide pH=7; Inert atmosphere; Schlenk technique;100%
With potassium hydroxide In water
With potassium hydroxide In water
41575-94-4

carboplatinum

5445-51-2

cyclobutane-1,1'-dicarboxylic acid

2C6H12N2O4Pt*3C6H8O4

Conditions
ConditionsYield
In water at 20℃; for 5h;99.6%

1,1-Cyclobutanedicarboxylic acid Specification

The 1,1-Cyclobutanedicarboxylic acid, with the CAS registry number 5445-51-2, is also known as 1-Carboxycyclobutanecarboxylic acid. It belongs to the product categories of Carboxylic Acids; Organic acids; Cyclobutanes & Cyclobutenes; Simple 4-Membered Ring Compounds; Carboxylic Acids; Ring Systems; Cycloalkanes; C6; Carbonyl Compounds. Its EINECS number is 226-651-2. This chemical's molecular formula is C6H8O4 and molecular weight is 144.13. What's more, its systematic name is cyclobutane-1,1-dicarboxylic acid. It is stable at common pressure and temperature, and it should be sealed and stored in a cool and dry place. It is used as drug intermediates.

Physical properties of 1,1-Cyclobutanedicarboxylic acid are: (1)ACD/LogP: -0.24; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -2.6; (4)ACD/LogD (pH 7.4): -4.19; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 52.6 Å2; (13)Index of Refraction: 1.564; (14)Molar Refractivity: 30.56 cm3; (15)Molar Volume: 93.9 cm3; (16)Polarizability: 12.11×10-24cm3; (17)Surface Tension: 80.5 dyne/cm; (18)Density: 1.534 g/cm3; (19)Flash Point: 189.6 °C; (20)Enthalpy of Vaporization: 67.31 kJ/mol; (21)Boiling Point: 366.4 °C at 760 mmHg; (22)Vapour Pressure: 2.27E-06 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-bromo-3-chloropropane and diethyl malonate with the existence of sodium ethoxide, then diethyl cyclobutane-1,1-dicarboxylate is produced, and finally the product is made through hydrolysis.

Uses of 1,1-Cyclobutanedicarboxylic acid: it can be used to produce cyclobutane-1,1-diyl-bis-methanol by heating. It will need reagent LiAlH4 and solvent tetrahydrofuran with the reaction time of 12 hours. The yield is about 88%.

1,1-Cyclobutanedicarboxylic acid can be used to produce cyclobutane-1,1-diyl-bis-methanol by heating

When you are using this chemical, please be cautious about it as the following:
This chemical can cause burns. It is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need wear suitable protective clothing, gloves and eye/face protection. In case of accident or if you feel unwell, you must seek medical advice immediately (show the label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O)C1(C(=O)O)CCC1
(2)Std. InChI: InChI=1S/C6H8O4/c7-4(8)6(5(9)10)2-1-3-6/h1-3H2,(H,7,8)(H,9,10)
(3)Std. InChIKey: CCQPAEQGAVNNIA-UHFFFAOYSA-N

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