[ CAS No. 260352-79-2 ]

Name: 260352-79-2|Butyl 2,2-difluorocyclopropanecarboxylate|98%
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3d Animation Molecule Structure of 260352-79-2

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Quality Control of [ 260352-79-2 ]

COA NMR CNMR HPLC LC-MS

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Alternatived Products of [ 260352-79-2 ]

Product Details of [ 260352-79-2 ]

CAS No. :	260352-79-2	MDL No. :	MFCD06797747
Formula :	C₈H₁₂F₂O₂	Boiling Point :	175.2°C at 760 mmHg
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	178.18 g/mol	Pubchem ID :	2761400
Synonyms :

Calculated chemistry of of [ 260352-79-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.88
Num. rotatable bonds :	5
Num. H-bond acceptors :	4.0
Num. H-bond donors :	0.0
Molar Refractivity :	39.88
TPSA :	26.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.87 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.1
Log Po/w (XLOGP3) :	2.14
Log Po/w (WLOGP) :	2.83
Log Po/w (MLOGP) :	1.88
Log Po/w (SILICOS-IT) :	2.41
Consensus Log Po/w :	2.27

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.96
Solubility :	1.94 mg/ml ; 0.0109 mol/l
Class :	Very soluble
Log S (Ali) :	-2.32
Solubility :	0.845 mg/ml ; 0.00474 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.31
Solubility :	0.863 mg/ml ; 0.00484 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.54

Safety of [ 260352-79-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 260352-79-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 260352-79-2 ]
Downstream synthetic route of [ 260352-79-2 ]

[ 260352-79-2 ] Synthesis Path-Upstream 1~10

1
[ 260352-79-2 ]
[ 107873-03-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	for 14 h; Reflux	A colorless solution of butyl 2,2-difluorocyclopropanecarboxylate (1-136) (65.0 g, 330 mmol) in aq .NaOH (750 ml_ H20, 52.5 g NaOH) was refluxed for ~14 hr. A pale yellow solution was formed. The reaction solution was cooled to room temperature, and then concentrated in vacuo to ~250 mL volume. In an ice bath (~0-5 °C), the residue was adjusted to pH ~3-4 using cone, aq. HCI (~70 mL). The resulting solution was extracted with EtOAc (2 x 500 mL). The combined organic layers were dried over Na2S04 and concentrated under high vacuum to give 2,2-difluorocyclopropanecarboxylic acid (1-137) (30 g, 75percent) as a yellow oil which gradually solidified on standing to give a pale yellow solid. 1H NMR (400 MHz, CDCI3) δ ppm 10.78 (s, 1 H), 2.41 - 2.47 (m, 1 H), 2.05 - 2.08 (m, 1 H), 1 .80 -1 .83 (m, 1 H).

Reference： [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 339 - 343
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4104 - 4114
[3] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 96-97
[4] Journal of Organic Chemistry, 2011, vol. 76, # 9, p. 3450 - 3456

2
[ 141-32-2 ]
[ 120801-75-4 ]
[ 260352-79-2 ]

Yield	Reaction Conditions	Operation in experiment
59%	Stage #1: With sodium fluoride In toluene for 1 h; Inert atmosphere; Reflux Stage #2: for 8 h; Inert atmosphere; Reflux	A solution of butyl prop-2-enoate (80 g, 6.24 mol) and a catalytic amount of NaF (1 .57 g, 375 mmol) in anhydrous toluene (800 ml_) was degassed with nitrogen 3 times, and then refluxed for 1 hr. Then, tri methylsilyl difluoro(fluorosulfonyl)acetate (250 g, 9.99 mol) was added dropwise to the refluxing solution over a period of 40 mins. After the addition, the resulting pale colorless solution was refluxed under N2 for a further 8 hr. The reaction solution was cooled to room temperature to afford a pale yellow solution. The solvent was removed under vacuum at ~45 °C, The combined residue (~130 ml_) was firstly distilled at 130 °C under atmospheric pressure to remove residual toluene, and then distilled under reduced pressure (~0.02 atm) at the same temperature to give butyl 2,2-difluorocyclopropanecarboxylate (1-136) (65 g, 59percent) as a colorless oil. 1H NMR (400 MHz, CDCI3) δ ppm 4.09 - 4.21 (m, 2 H), 2.36 - 2.47 (m, 1 H), 2.04 - 2.07 (m, 1 H), 1 .60 - 1 .66 (m, 3 H), 1 .36 - 1 .42 (m, 2 H), 0.94 (t, J = 7.2 Hz, 3 H).

Reference： [1] Journal of Fluorine Chemistry, 2005, vol. 126, # 3, p. 339 - 343
[2] Patent: WO2016/97918, 2016, A1, . Location in patent: Page/Page column 96
[3] Organic Syntheses, 2003, vol. 80, p. 172 - 176

3
[ 141-32-2 ]
[ 260352-79-2 ]

Reference： [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469

4
[ 141-32-2 ]
[ 757203-27-3 ]
[ 260352-79-2 ]

Reference： [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469

5
[ 111-66-0 ]
[ 141-32-2 ]
[ 260352-79-2 ]

Reference： [1] Organic Letters, 2000, vol. 2, # 4, p. 563 - 564

6
[ 141-32-2 ]
[ 260352-79-2 ]

Reference： [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469

7
[ 141-32-2 ]
[ 81290-20-2 ]
[ 260352-79-2 ]

Reference： [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4104 - 4114
[2] Chemical Communications, 2017, vol. 53, # 31, p. 4382 - 4385

8
[ 141-32-2 ]
[ 260352-79-2 ]

Reference： [1] Journal of Fluorine Chemistry, 2004, vol. 125, # 3, p. 459 - 469

9
[ 141-32-2 ]
[ 680-15-9 ]
[ 260352-79-2 ]

Reference： [1] Journal of Organic Chemistry, 2012, vol. 77, # 12, p. 5461 - 5464

10
[ 141-32-2 ]
[ 260352-79-2 ]

Reference： [1] Chemical Communications, 2017, vol. 53, # 31, p. 4382 - 4385

[ 260352-79-2 ] Synthesis Path-Downstream 1~11

1
[ 111-66-0 ]
[ 141-32-2 ]
[ 260352-79-2 ]

Reference： [1]Organic Letters,2000,vol. 2,p. 563 - 564

2
[ 141-32-2 ]
ethyldimethylsilyl fluorosulfonyldifluoroacetate [ No CAS ]
[ 260352-79-2 ]

Reference： [1]Journal of Fluorine Chemistry,2004,vol. 125,p. 459 - 469

3
[ 141-32-2 ]
chloromethyldimethylsilyl fluorosulfonyldifluoroacetate [ No CAS ]
[ 260352-79-2 ]

Reference： [1]Journal of Fluorine Chemistry,2004,vol. 125,p. 459 - 469

4
[ 141-32-2 ]
2-(trimethylsilyl)ethyl fluorosulfonyldifluoroacetate [ No CAS ]
[ 260352-79-2 ]

Reference： [1]Journal of Fluorine Chemistry,2004,vol. 125,p. 459 - 469

5
[ 141-32-2 ]
[ 757203-27-3 ]
[ 260352-79-2 ]

Reference： [1]Journal of Fluorine Chemistry,2004,vol. 125,p. 459 - 469

6
[ 141-32-2 ]
[ 120801-75-4 ]
[ 260352-79-2 ]

Yield	Reaction Conditions	Operation in experiment
59%		A solution of butyl prop-2-enoate (80 g, 6.24 mol) and a catalytic amount of NaF (1 .57 g, 375 mmol) in anhydrous toluene (800 ml_) was degassed with nitrogen 3 times, and then refluxed for 1 hr. Then, tri methylsilyl difluoro(fluorosulfonyl)acetate (250 g, 9.99 mol) was added dropwise to the refluxing solution over a period of 40 mins. After the addition, the resulting pale colorless solution was refluxed under N2 for a further 8 hr. The reaction solution was cooled to room temperature to afford a pale yellow solution. The solvent was removed under vacuum at ~45 C, The combined residue (~130 ml_) was firstly distilled at 130 C under atmospheric pressure to remove residual toluene, and then distilled under reduced pressure (~0.02 atm) at the same temperature to give butyl 2,2-difluorocyclopropanecarboxylate (1-136) (65 g, 59%) as a colorless oil. 1H NMR (400 MHz, CDCI3) delta ppm 4.09 - 4.21 (m, 2 H), 2.36 - 2.47 (m, 1 H), 2.04 - 2.07 (m, 1 H), 1 .60 - 1 .66 (m, 3 H), 1 .36 - 1 .42 (m, 2 H), 0.94 (t, J = 7.2 Hz, 3 H).

Reference： [1]Journal of Fluorine Chemistry,2005,vol. 126,p. 339 - 343
[2]Patent: WO2016/97918,2016,A1 .Location in patent: Page/Page column 96
[3]Organic Syntheses,2003,vol. 80,p. 172 - 176

7
[ 260352-79-2 ]
[ 107873-03-0 ]

Yield	Reaction Conditions	Operation in experiment
75%	With water; sodium hydroxide; for 14h;Reflux;	A colorless solution of <strong>[260352-79-2]butyl 2,2-difluorocyclopropanecarboxylate</strong> (1-136) (65.0 g, 330 mmol) in aq .NaOH (750 ml_ H20, 52.5 g NaOH) was refluxed for ~14 hr. A pale yellow solution was formed. The reaction solution was cooled to room temperature, and then concentrated in vacuo to ~250 mL volume. In an ice bath (~0-5 C), the residue was adjusted to pH ~3-4 using cone, aq. HCI (~70 mL). The resulting solution was extracted with EtOAc (2 x 500 mL). The combined organic layers were dried over Na2S04 and concentrated under high vacuum to give 2,2-difluorocyclopropanecarboxylic acid (1-137) (30 g, 75%) as a yellow oil which gradually solidified on standing to give a pale yellow solid. 1H NMR (400 MHz, CDCI3) delta ppm 10.78 (s, 1 H), 2.41 - 2.47 (m, 1 H), 2.05 - 2.08 (m, 1 H), 1 .80 -1 .83 (m, 1 H).

Reference： [1]Journal of Fluorine Chemistry,2005,vol. 126,p. 339 - 343
[2]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4104 - 4114
[3]Patent: WO2016/97918,2016,A1 .Location in patent: Page/Page column 96-97
[4]Journal of Organic Chemistry,2011,vol. 76,p. 3450 - 3456

8
[ 75-05-8 ]
[ 260352-79-2 ]
[ 1186609-06-2 ]

Yield	Reaction Conditions	Operation in experiment
		Referential Example 2 5-(2,2-Difluorocyclopropyl)-lH-pyrazol-3-amine (45) To a solution of MeCN (1.1 g, 16.8 mmol) in THF (60 mL) was added dropwise n-BuLi in THF (11.2 mL, 40.3 mmol) at -78C, and the reaction mixture was stirred at -78 C under N2 for 30 min. Butyl 2,2- difluorocyclopropanecarboxylate (3.0 g, 16.8 mmol) was added at -78 C, and the reaction mixture was allowed to warm to RT over 3 h. The reaction mixture was quenched with water and adjusted to pH 7 with IN HCl. The mixture was extracted with EtOAc, and the organic layer was washed with brine, dried (Na2S04), filtered and concentrated in vacuo to afford crude 3-(2,2-difluorocyclopropyl)-3- oxopropanenitrile. A mixture of crude 3-(2,2-difluorocyclopropyl)-3-oxopropanenitrile and hydrazine (2.0 g, 50.4 mmol, 85% pure) in EtOH (30 mL) was stirred at reflux for 16 h. The reaction mixture was concentrated to dryness under reduced pressure. The crude residue was purified by chromatography eluting with an EtO Ac/petroleum ether gradient (12.5 to 100% EtOAc) to afford 2.1 g (78.5%>) of 45 as a yellow solid: 1H NMR (400 MHz, DMSO-d6): delta 11.40 (br s, 1H), 5.26 (s, 1H), 4.80 (br s, 2H), 2.78 - 2.66 (m, 1H), 2.04 - 1.75 (m, 1H), 1.73 - 1.21 (m, 1H); MS (ESI+) m/z = 160.1 [M +1]+.
		A solution of acetonitrile (0.97 mL, 18.5 mmol) in tetrahydrofuran(50 mL) was cooled to -78C and treated with n-butyllithium in hexanes (11.7 mL, 19.0 mmol) over 5 minutes. The reaction mixture was stirred for 30 minutes, and then n-butyl 2,2- difluorocyclopropane carboxylate (3.0 g, 16.8 mmol) was added. The reaction mixture was allowed to warm to room temperature over 2 hours. The reaction mixture was poured into water (25 mL) and acidified by addition of 10% aqueous hydrochloric acid. The organic layers were extracted into diethyl ether (3 X 30 mL), dried (MgSO4) and concentrated to afford crude 3-(2,2-difluorocyclopropyl)-3-oxo-propionitrile (2 g).

Reference： [1]Patent: WO2013/26914,2013,A1 .Location in patent: Page/Page column 90-91
[2]Patent: WO2009/111279,2009,A1 .Location in patent: Page/Page column 112

9
[ 141-32-2 ]
[ 680-15-9 ]
[ 260352-79-2 ]

Reference： [1]Journal of Organic Chemistry,2012,vol. 77,p. 5461 - 5464

10
[ 141-32-2 ]
[Co^III(meso-tetraphenylporphyrinato)(CF₃)] [ No CAS ]
[ 260352-79-2 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 4382 - 4385

11
[ 141-32-2 ]
[ 81290-20-2 ]
[ 260352-79-2 ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4104 - 4114
[2]Chemical Communications,2017,vol. 53,p. 4382 - 4385

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Physical hazards
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H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
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H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 260352-79-2 ]

Quality Control of [ 260352-79-2 ]

Related Doc. of [ 260352-79-2 ]

Product Details of [ 260352-79-2 ]

Calculated chemistry of of [ 260352-79-2 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 260352-79-2 ]

Application In Synthesis of [ 260352-79-2 ]

[ 260352-79-2 ] Synthesis Path-Upstream 1~10

[ 260352-79-2 ] Synthesis Path-Downstream 1~11

Related Functional Groups of [ 260352-79-2 ]

Fluorinated Building Blocks

Aliphatic Cyclic Hydrocarbons

Esters

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 260352-79-2 ]