1,1-Cyclopropanedicarboxylic acid supplier

Name
1,1-Cyclopropanedicarboxylic acid
EINECS 209-917-2
CAS No. 598-10-7
Article Data32
CAS DataBase
Density 1.708 g/cm³
Solubility Soluble in water
Melting Point 134-136 °C(lit.)
Formula C₅H₆O₄
Boiling Point 371.307 °C at 760 mmHg
Molecular Weight 130.1
Flash Point 192.54 °C
Transport Information UN 3261 8/PG 2
Appearance white to almost white crystalline powder
Safety 26-45-36/37/39
Risk Codes 36/37/38-34
Molecular Structure
Hazard Symbols Xi, C
Synonyms Cyclopropane-1,1-dicarboxylic acid;1,1-Cyclopropane dicarboxylic acid;Cyclopropane-1,1-dicarboxylic acid;
PSA 74.60000
LogP -0.06420

Synthetic route

: 1634-04-4
tert-butyl methyl ether

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
In water	90.7%

: 1247181-41-4
C13H14O5

: 1247181-42-5
C13H14O5

A: 93-56-1
phenylethane 1,2-diol

B: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide at 60℃; for 4h;	A 89% B 87%

...Expand

: 6914-71-2
dimethyl 1,1-cyclopropanedicarboxylate

A: 598-10-7
cyclopropane-1,1-dicarboxylic acid

B: 113020-21-6
1,1-cyclopropanedicarboxylic acid monomethyl ester

Conditions

Conditions	Yield
With sodium hydroxide In water at 40℃; for 2h;	A 11.6% B 87%

: 106-93-4
ethylene dibromide

: 105-53-3
diethyl malonate

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With benzyltrimethylammonium chloride; sodium hydroxide In water at 20℃; for 2h;	78%
With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide In water at 20℃; for 2h;	78%
Stage #1: diethyl malonate With N-benzyl-N,N,N-triethylammonium chloride; sodium hydroxide at 20℃; for 0.166667h; Stage #2: ethylene dibromide at 20℃;	76.1%

: 6947-77-9
pyrimidine-5-spirocyclopropane-2,4,6(1H,3H,5H)-trione

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With sodium hydroxide at 85℃; for 4h;	77%

: 1559-02-0
diethyl cyclopropane-1,1-dicarboxylate

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
Stage #1: diethyl cyclopropane-1,1-dicarboxylate With sodium hydroxide Stage #2: With hydrogenchloride In water	50%
Stage #1: diethyl cyclopropane-1,1-dicarboxylate With sodium hydroxide Stage #2: With hydrogenchloride; water	50%
With barium dihydroxide

: 124-38-9
carbon dioxide

: 110419-17-5
lithium α-lithiocyclopropanecarboxylate

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
-20 deg C to room temp., 1 h;	22%

: 1558-81-2
1-carbethoxy-1-cyanocyclopropane

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide
Multi-step reaction with 2 steps 1: methanolic-aqueous KOH-solution 2: aqueous KOH-solution View Scheme

: 1558-81-2
1-carbethoxy-1-cyanocyclopropane

A: 598-10-7
cyclopropane-1,1-dicarboxylic acid

B: 6914-75-6
Cyclopropan-1-carbonsaeureethylester-1-carbonsaeureamid

Conditions

Conditions	Yield
With potassium hydroxide; dihydrogen peroxide

: 6914-79-0
1-cyano-cyclopropanecarboxylic acid

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide

: 146653-73-8
N,N'-bis(phenyl)cyclopropane-1,1-diamide

A: 598-10-7
cyclopropane-1,1-dicarboxylic acid

B: 56137-52-1
1-phenyl-2-oxo-3-pyrrolidine-3-carboxylic acid

Conditions

Conditions	Yield
With hydrogen bromide at 130℃;

: 6914-75-6
Cyclopropan-1-carbonsaeureethylester-1-carbonsaeureamid

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol

: 39590-81-3
[1-(hydroxymethyl)cyclopropyl]methanol

KMnO4: KMnO4

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 6914-79-0
1-cyano-cyclopropanecarboxylic acid

aqueous KOH-solution: aqueous KOH-solution

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 7664-93-9
sulfuric acid

: 4,7-dioxo-spiro[2.4]heptane-5,6-dicarboxylic acid

A: 110-15-6
succinic acid

B: 598-10-7
cyclopropane-1,1-dicarboxylic acid

...Expand

: 4,7-dioxo-spiro[2.4]heptane-5,6-dicarboxylic acid

alkali: alkali

A: 110-15-6
succinic acid

B: 598-10-7
cyclopropane-1,1-dicarboxylic acid

...Expand

: 146653-73-8
N,N'-bis(phenyl)cyclopropane-1,1-diamide

: 10035-10-6, 12258-64-9
hydrogen bromide

A: 598-10-7
cyclopropane-1,1-dicarboxylic acid

B 1-phenyl-pyrrolidone-(2)-carboxylic acid-(3): 1-phenyl-pyrrolidone-(2)-carboxylic acid-(3)

Conditions

Conditions	Yield
at 130℃;

...Expand

: sodium 1,1-cyclopropyldicarboxylate

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

Conditions

Conditions	Yield
With hydrogenchloride In water

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: diethyl malonate

Conditions

Conditions	Yield
With 18O-labeled water at 40℃; for 672h; Inert atmosphere;	100%

: 372-19-0
meta-fluoroaniline

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 1247859-37-5
1-((3-fluorophenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride; triethylamine In dichloromethane for 0.5h; Cooling with ice; Stage #2: meta-fluoroaniline In dichloromethane at 20℃; for 1.5h; Cooling with ice;	94.5%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: meta-fluoroaniline With triethylamine In Isopropyl acetate for 3h;	76%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: meta-fluoroaniline With triethylamine In Isopropyl acetate for 2h;	76%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 12h; Inert atmosphere;	33%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 371-40-4
4-fluoroaniline

: 849217-48-7
((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With triethylamine In tetrahydrofuran at 10℃; for 0.5h; Stage #2: 4-fluoroaniline With thionyl chloride In tetrahydrofuran at 10 - 20℃; for 4h;	93%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride; triethylamine In tetrahydrofuran for 1h; Cooling with ice; Stage #2: 4-fluoroaniline In tetrahydrofuran for 3h; Cooling with ice;	92%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 25℃; for 5h; Large scale; Stage #2: 4-fluoroaniline With triethylamine In Isopropyl acetate for 1h; Large scale;	77%

: 13257-67-5
2-amino-2-methylpropionic acid methyl ester

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 2-{[1-(1-methoxycarbonyl-1-methyl-ethylcarbamoyl)-cyclopropanecarbonyl]-amino}-2-methyl-propionic acid methyl ester

Conditions

Conditions	Yield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 72h;	92%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 4360-91-2, 131953-20-3
α-carboxy-γ-butyrolactone

Conditions

Conditions	Yield
With triethylamine hydrobromide In acetonitrile at 75℃; for 16h;	90%
With triethylamine hydrobromide In acetonitrile at 75℃; for 16h; Inert atmosphere;	90%
With triethylamine hydrobromide In acetonitrile at 75℃; for 16h; Inert atmosphere;	90%
With tetrabutylammomium bromide In acetonitrile at 75℃; for 16h; Inert atmosphere;

: 67-56-1
methanol

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 6914-71-2
dimethyl 1,1-cyclopropanedicarboxylate

Conditions

Conditions	Yield
With Oxone In toluene at 60℃; for 48h; Green chemistry;	85%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 106-40-1
4-bromo-aniline

: 113136-80-4
1-((4-bromophenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 4-bromo-aniline With triethylamine In Isopropyl acetate for 3h;	84%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 4-bromo-aniline With triethylamine In Isopropyl acetate for 2h;	84%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 123-30-8
4-amino-phenol

: C17H16N2O4

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With O‑(6‑chlorobezotriazol‑1‑yl)‑N,N,N,N‑tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 40℃; for 1.5h; Stage #2: 4-amino-phenol In tetrahydrofuran at 20 - 40℃;	83%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 106-95-6
allyl bromide

: 126525-80-2
2-allyloxycarbonyl-γ-butyrolactone

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 75℃; for 16h;	82%
With triethylamine 1) CH3CN; 2) CH3CN, room temperature (2 h), 75 deg C (16 h); Yield given. Multistep reaction;

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 90-04-0
2-methoxy-phenylamine

: 918642-60-1
1-((4-methoxyphenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With triethylamine In tetrahydrofuran for 0.25h; Cooling with ice; Stage #2: With thionyl chloride In tetrahydrofuran for 0.25h; Cooling with ice; Stage #3: 2-methoxy-phenylamine In tetrahydrofuran at 20℃; for 18h;	82%

: 455-14-1
4-trifluoromethylphenylamine

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 113136-89-3
1-((4-(trifluoromethyl)phenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 4-trifluoromethylphenylamine With triethylamine In Isopropyl acetate for 3h;	82%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 4-trifluoromethylphenylamine With triethylamine In Isopropyl acetate for 2h;	82%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 108-42-9
3-chloro-aniline

: 146653-80-7
1-((3-chlorophenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 3-chloro-aniline With triethylamine In Isopropyl acetate for 3h;	81%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 3-chloro-aniline With triethylamine In Isopropyl acetate for 2h;	81%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 98-16-8
3-trifluoromethylaniline

: 796883-79-9
1-((3-(trifluoromethyl)phenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 3-trifluoromethylaniline With triethylamine In Isopropyl acetate for 3h;	81%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 3-trifluoromethylaniline With triethylamine In Isopropyl acetate for 2h;	81%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 106-49-0
p-toluidine

: 1248667-63-1
1-(p-tolylcarbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: p-toluidine With triethylamine In Isopropyl acetate for 3h;	79%
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: p-toluidine With triethylamine In Isopropyl acetate for 2h;	79%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 25℃; for 12h; Inert atmosphere;	37%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 2237-30-1
m-cyanoaniline

: 1-((3-cyanophenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: m-cyanoaniline With triethylamine In Isopropyl acetate for 3h;	79%

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 873-74-5
4-Aminobenzonitrile

: 1-((3-cyanophenyl)carbamoyl)cyclopropane-1-carboxylic acid

Conditions

Conditions	Yield
Stage #1: cyclopropane-1,1-dicarboxylic acid With thionyl chloride In Isopropyl acetate at 0 - 20℃; for 6h; Stage #2: 4-Aminobenzonitrile With triethylamine In Isopropyl acetate for 3h;	79%

: gadolinium(III) nitrate hexahydrate

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 7732-18-5
water

: 1310-73-2
sodium hydroxide

: 6C5H4O4(2-)*7Gd(3+)*3CHO2(1-)*6HO(1-)*8H2O

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 72h; Autoclave;	79%

...Expand

: dysprosium(III) nitrate hexahydrate

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 7732-18-5
water

: 1310-73-2
sodium hydroxide

: 6C5H4O4(2-)*3CHO2(1-)*6HO(1-)*8H2O*7Dy(3+)

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 72h; Autoclave;	79%

...Expand

: 598-10-7
cyclopropane-1,1-dicarboxylic acid

: 36050-78-9
Bis(trimethylsilyl)methylidene triphenylphosphorane

: 141957-45-1
2-(Triphenyl-λ5-phosphanylidene)-1-{1-[2-(triphenyl-λ5-phosphanylidene)-acetyl]-cyclopropyl}-ethanone

Conditions

Conditions	Yield
In tetrahydrofuran 1) RT, 30 min, 2) reflux, 3-4 d;	78%

1,1-Cyclopropanedicarboxylic acid Specification

1,1-Cyclopropanedicarboxylic acid is an organic compound with the formula C₅H₆O₄, and its systematic name is the same with the product name. With the CAS registry number 598-10-7, it is also named as Cyclopropane-1,1-dicarboxylic acid. It belongs to the product categories of Carboxylic Acids; Organic acids; Cyclopropanes; Simple 3-Membered Ring Compounds; Carboxylic Acids; Ring Systems; C1 to C5; Carbonyl Compounds. Its EINECS number is 209-917-2. In addition, the molecular weight is 130.10.

Physical properties of 1,1-Cyclopropanedicarboxylic acid are: (1)ACD/LogP: -0.768; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -4.69; (4)ACD/LogD (pH 7.4): -5.50; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 1.00; (8)ACD/KOC (pH 7.4): 1.00; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 74.6 Å²; (13)Index of Refraction: 1.597; (14)Molar Refractivity: 25.955 cm³; (15)Molar Volume: 76.169 cm³; (16)Polarizability: 10.289×10^-24cm³; (17)Surface Tension: 100.657997131348 dyne/cm; (18)Density: 1.708 g/cm³; (19)Flash Point: 192.54 °C; (20)Enthalpy of Vaporization: 67.902 kJ/mol; (21)Boiling Point: 371.307 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Preparation: this chemical can be prepared by 5,7-diaza-spiro[2.5]octane-4,6,8-trione at the temperature of 85 °C. This reaction will need reagent 0.2 N NaOH with the reaction time of 4 hours. The yield is about 77%.

1,1-Cyclopropanedicarboxylic acid can be prepared by 5,7-diaza-spiro[2.5]octane-4,6,8-trione at the temperature of 85 °C

Uses of 1,1-Cyclopropanedicarboxylic acid: it can be used to produce 1,1-Bis(trifluormethyl)cyclopropan at the temperature of 120 °C. It will need reagent SF₄with the reaction time of 24 hours. The yield is about 59%.

1,1-Cyclopropanedicarboxylic acid can be used to produce 1,1-Bis(trifluormethyl)cyclopropan at the temperature of 120 °C

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 to 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)CC1
(2)Std. InChI: InChI=1S/C5H6O4/c6-3(7)5(1-2-5)4(8)9/h1-2H2,(H,6,7)(H,8,9)
(3)Std. InChIKey: FDKLLWKMYAMLIF-UHFFFAOYSA-N

Product Name

1,1-Cyclopropanedicarboxylic acid

Synthetic route

1,1-Cyclopropanedicarboxylic acid Specification

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