[ CAS No. 593-71-5 ] {[proInfo.proName]}

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Quality Control of [ 593-71-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 593-71-5 ]

SDS Specification

Alternatived Products of [ 593-71-5 ]

Product Details of [ 593-71-5 ]

CAS No. :	593-71-5	MDL No. :	MFCD00001078
Formula :	CH₂ClI	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PJGJQVRXEUVAFT-UHFFFAOYSA-N
M.W :	176.38	Pubchem ID :	11644
Synonyms :

Calculated chemistry of [ 593-71-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	3
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	0.0
Num. H-bond donors :	0.0
Molar Refractivity :	24.68
TPSA :	0.0 ?2

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.27 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.4
Log Po/w (XLOGP3) :	1.56
Log Po/w (WLOGP) :	1.62
Log Po/w (MLOGP) :	1.82
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	1.68

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	3.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.92
Solubility :	2.14 mg/ml ; 0.0121 mol/l
Class :	Very soluble
Log S (Ali) :	-1.17
Solubility :	11.9 mg/ml ; 0.0676 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.85
Solubility :	2.5 mg/ml ; 0.0142 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.28

Safety of [ 593-71-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P310+P330-P302+P352-P304+P340+P312-P305+P351+P338-P332+P313-P337+P313-P403+P233-P405-P501	UN#:	2810
Hazard Statements:	H301-H315-H319-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 593-71-5 ]

* 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 [ 593-71-5 ]
Downstream synthetic route of [ 593-71-5 ]

[ 593-71-5 ] Synthesis Path-Upstream 1~1

1
[ 593-71-5 ]
[ 82034-46-6 ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: With sodium ethanolate In N,N,N,N,N,N-hexamethylphosphoric triamide at 20℃; for 24 h; Large scale Stage #2: at 20℃; for 2 h; Large scale	To 50L reactor, add 1.9 kg intermediate 4, hexamethylphosphoric acid triamide 19L, sodium ethoxide 0.26 kg. React under the condition of room temperature for 24 hours. Add chloroiodomethane 1.4 kg. Stir for 2 hours. The reaction liquid quickly add 570L in water, separate out a large amount of yellow solid, filtering. The filter cake is added to the chloroform 5.7L dissolved, for sequentially 0.3M sodium thiosulfate solution 1.9L, 0 . 4M sodium bicarbonate solution, 1.9L saturated salt water 1.9L washing liquid, anhydrous sodium sulfate drying, decolorized with active carbon. Filtered, concentrated under reduced pressure to dryness; anhydrous ethanol is added 13.3L, heating to reflux, the solid is completely dissolved, gradually cooling crystallization, filtration. 40 °C blast drying, to obtain white solid 1.6 kg, yield 89percent.

Reference： [1] Patent: CN106554383, 2017, A, . Location in patent: Paragraph 0025; 0031; 0032

[ 593-71-5 ] Synthesis Path-Downstream 1~14

1
[ 593-71-5 ]
[ 98045-03-5 ]
[ 70606-85-8 ]

Reference： [1]Journal of Medicinal Chemistry,1979,vol. 22,p. 657 - 661

2
[ 593-71-5 ]
[ 4522-04-7 ]
[ 102123-74-0 ]

Reference： [1]Tetrahedron Letters,1997,vol. 38,p. 3175 - 3178
[2]Tetrahedron Letters,1997,vol. 38,p. 3175 - 3178

3
[ 593-71-5 ]
[ 51987-73-6 ]
[ 102123-74-0 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 7344 - 7347

4
[ 4313-03-5 ]
[ 593-71-5 ]
1-chloro-octa-3,5-dien-2-ol [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2007,vol. 5,p. 318 - 323

5
[ 593-71-5 ]
[ 94242-85-0 ]
[ 82954-89-0 ]

Reference： [1]Organometallics,1985,vol. 4,p. 1687 - 1689

6
[ 593-71-5 ]
[ 557-20-0 ]
[ 151907-79-8 ]
[ 1201187-23-6 ]

Yield	Reaction Conditions	Operation in experiment
35%		To <strong>[151907-79-8](1S,4R)-4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylic acid</strong> (2.70 g, 11.8 mmol, Preparation No.17) in DCM (170 mL) was slowly added diethylzinc (1.1 M in toluene, 54.0 mL, 59.4 mmol). The mixture was stirred for about 10 min at ambient temperature, cooled to about 0 C., and treated drop-wise with a solution of chloroiodomethane (4.30 mL, 59.4 mmol) in DCM (24 mL). The reaction mixture was allowed to warm to room temperature and was stirred for about 18 h. Saturated aqueous NH4Cl (10 mL) was added and the mixture was stirred for about 20 min. The layers were separated and the aqueous layer was further extracted with DCM (20 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 0-100% EtOAc/heptane to afford (1R,2S,4R,5S)-methyl 4-(ethoxycarbonylamino)bicyclo[3.1.0]hexane-2-carboxylate (0.95 g, 35%): LC/MS (Table 2, Method a) Rt=1.88 min; MS m/z: 228 (M+H)+.

Reference： [1]Patent: US2009/312338,2009,A1 .Location in patent: Page/Page column 129

7
[ 593-71-5 ]
[ 145576-28-9 ]
ethyl spiro[2.5]octane-6-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diethylzinc; In hexane; 1,2-dichloro-ethane; at 0 - 20℃; for 19h;	Cap N-8 At 0 C., to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed by the addition of 1 N diethylzinc in hexane (0.761 mL, 0.761 mmol). The reaction was stirred at 0 C. for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HCl, the organic phase was washed with sat. NaCl, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 min gradient of 0-6% EtOAc in hexane to yield ethyl spiro[2.5]octane-6-carboxylate. 1H NMR (400 MHz, CDCl3) delta ppm 4.08-4.18 (2H, m), 2.32 (1H, tq, J=11.01, 3.53 Hz), 1.85-1.93 (2H, m), 1.53-1.74 (4H, m), 1.28-1.35 (2H, m), 1.22-1.28 (3H, m), 0.28 (2H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17-0.25 (2H, m).
	With diethylzinc; In hexane; 1,2-dichloro-ethane; at 0 - 20℃; for 19h;	At 0 C, to a solution of ethyl 4-methylenecyclohexanecarboxylate (0.08 g) in DCE (1 mL) was added chloroiodomethane (0.110 mL, 1.522 mmol), followed bythe addition of 1 N diethylzinc in hexane (0.76 1 mL, 0.76 1 mmol). The reaction was stirred at 0 C for 1 hr, then stirred at rt for 18 hrs. The reaction mixture was diluted with EtOAc and 1 N HC1, the organic phase was washed with sat. NaC1, dried over anhydrous Na2SO4, filtered and concentrated. The crude product was charged to a 25 g silica gel cartridge which was eluted with a 20 mm gradient of 0-6% EtOAc inhexane to yield ethyl spiro[2.5]octane-6-carboxylate. ?H NMR (400 MHz, CDC13) ppm 4.08-4.18(2 H, m), 2.32 (1 H, tq, J=11.01, 3.53 Hz), 1.85 - 1.93 (2 H, m), 1.53- 1.74 (4 H, m), 1.28 - 1.35 (2 H, m), 1.22 - 1.28 (3 H, m), 0.28 (2 H, ddd, J=8.53, 5.52, 1.51 Hz), 0.17 - 0.25 (2 H, m).

Reference： [1]Patent: US2013/183269,2013,A1 .Location in patent: Paragraph 1343; 1344
[2]Patent: WO2015/5901,2015,A1 .Location in patent: Page/Page column 543

8
[ 593-71-5 ]
[ 4747-72-2 ]
[ 19047-31-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With methyllithium; lithium bromide; In diethyl ether; at -78℃; for 1h;	General procedure: To a cooled (-78C) solution of isocyanate (1.0 equiv) in dry Et2O (1 M concentration) was added the dihalomethane derivative (1.5 equiv). After 2 min, an ethereal solution of 1.5 M MeLi-LiBr (1.25equiv) was added dropwise over 5 min. The resulting solution was stirred for the appropriate time (see Table 1 and Scheme 2) at that temperature. Sat. aq NH4Cl was added (2 mL/mmol substrate) and the cooling bath was removed, the mixture was stirred till it reached r.t., and then it was extracted with additional Et2O (2 × 5 mL) and washed with water (5 mL) and brine (10 mL). The organic phase was dried (anhyd Na2SO4), filtered, and the solvent removed under reduced pressure to give pure samples of haloacetamides.

Reference： [1]Chemical Communications,2013,vol. 49,p. 8383 - 8385
[2]Synthesis,2014,vol. 46,p. 2897 - 2909

9
[ 41042-12-0 ]
[ 593-71-5 ]
1-n-propylspiro[indole-3,2'-oxiran]-2(1H)-one [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2016,vol. 358,p. 172 - 177

10
[ 198967-24-7 ]
[ 593-71-5 ]
[ 18156-74-6 ]
2-chloro-1-(2-fluorophenyl)-N-methoxy-N-methyl-1-[(trimethylsilyl)oxy]ethanamine [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 9498 - 9501

11
[ 593-71-5 ]
[ 95091-92-2 ]
[ 18156-74-6 ]
2-chloro-1-(2-furyl)-N-methoxy-N-methyl-1-[(trimethylsilyl)oxy]ethanamine [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 9498 - 9501

12
[ 593-71-5 ]
[ 1626-24-0 ]
[ 27259-63-8 ]

Reference： [1]Chemical Communications,2018,vol. 54,p. 10112 - 10115

13
[ 593-71-5 ]
[ 180609-56-7 ]
benzyl 2-(2-chloroacetyl)-1-piperidinecarboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		To a cooled solution (-78C) of 0.42 g (2.2 eq.) chloro-iodo-methane in 10 mL THF, 1.58 mL (2.2 eq.) of LDA 1.5 M solution in THF was added dropwise in a nitrogen atmosphere. The temperature was maintained below -72C. After stirring for additional 10 min at -78 C a solution of 0.3 g (1 eq.) of 1- benzyl 2-methyl 1,2-piperidinedicarboxylate in 3 mL THF was added dropwise. The internal temperature was maintained not higher than -72 C. After stirring for additional 5 min 1.08 mL (1.5 eq.) of LDA 1.5 M solution in THF was added dropwise. The internal temperature was maintained below - 72C. After stirring for further 30 min at -78C the reaction mixture was quenched with a solution of 1.2 g acetic acid in lOmL THF. The reaction mixture was allowed to warm to ambient temperature and 20 mL of water was added. The organic and aqueous phases were separated and the aqueous phase 3 times extracted with 25 mL of ethyl acetate. The combined organic washings were dried over magnesium sulphate, filtered, the solvents evaporated in vacuum and flashed chromatographed using heptane/dioxane 4: 1 mixture to give 0.15 g of the title product as almost colorless oil (Rf 0.12, yield 47%).

Reference： [1]Patent: WO2019/86469,2019,A1 .Location in patent: Page/Page column 33; 34

14
[ 593-71-5 ]
[ 21221-93-2 ]
1-(2-chloro-1-phenylethyl)-3,5-bis(trifluoromethyl)benzene [ No CAS ]

Reference： [1]Organic Letters,2020,vol. 22,p. 7629 - 7634

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Heat of Combustion ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

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Prevention
Code	Phrase
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P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
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P240	Ground/bond container and receiving equipment.
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Code	Phrase
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P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
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P315	Get immediate medical advice/attention.
P320
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P321
P322
P330	Rinse mouth.
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P334	Immerse in cool water/wrap n wet bandages.
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P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
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P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
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P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
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P378
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P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
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Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
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H221	Flammable gas
H222	Extremely flammable aerosol
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H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
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H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
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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
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H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
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H351	Suspected of causing cancer
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H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
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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

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[ CAS No. 593-71-5 ] {[proInfo.proName]}

Quality Control of [ 593-71-5 ]

Related Doc. of [ 593-71-5 ]

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Calculated chemistry of [ 593-71-5 ] Expand+

Physicochemical Properties

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Druglikeness

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Medicinal Chemistry

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[ 593-71-5 ] Synthesis Path-Upstream 1~1

[ 593-71-5 ] Synthesis Path-Downstream 1~14

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