[ CAS No. 106014-21-5 ] {[proInfo.proName]}

Name: 106014-21-5|Dimethyl 3-chloropyridine-2,5-dicarboxylate|96%
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DV 2D 3D

3d Animation Molecule Structure of 106014-21-5

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Quality Control of [ 106014-21-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 106014-21-5 ]

SDS Specification

Alternatived Products of [ 106014-21-5 ]

Product Details of [ 106014-21-5 ]

CAS No. :	106014-21-5	MDL No. :	MFCD00129113
Formula :	C₉H₈ClNO₄	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SINDYKCLGNROTL-UHFFFAOYSA-N
M.W :	229.62	Pubchem ID :	11470236
Synonyms :

Calculated chemistry of [ 106014-21-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.22
Num. rotatable bonds :	4
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	51.81
TPSA :	65.49 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.62 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.08
Log Po/w (XLOGP3) :	1.52
Log Po/w (WLOGP) :	1.31
Log Po/w (MLOGP) :	0.86
Log Po/w (SILICOS-IT) :	1.77
Consensus Log Po/w :	1.51

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.25
Solubility :	1.28 mg/ml ; 0.00558 mol/l
Class :	Soluble
Log S (Ali) :	-2.5
Solubility :	0.72 mg/ml ; 0.00313 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-2.8
Solubility :	0.363 mg/ml ; 0.00158 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.06

Safety of [ 106014-21-5 ]

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

Application In Synthesis of [ 106014-21-5 ]

* 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 [ 106014-21-5 ]
Downstream synthetic route of [ 106014-21-5 ]

[ 106014-21-5 ] Synthesis Path-Upstream 1~5

1
[ 67-56-1 ]
[ 56055-54-0 ]
[ 201230-82-2 ]
[ 51269-81-9 ]
[ 220656-93-9 ]
[ 106014-21-5 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 2, p. 393 - 404

2
[ 67-56-1 ]
[ 56055-54-0 ]
[ 201230-82-2 ]
[ 51269-81-9 ]
[ 220656-93-9 ]
[ 106014-21-5 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 2, p. 393 - 404

3
[ 32658-54-1 ]
[ 67-56-1 ]
[ 106014-21-5 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5
[2] Patent: WO2009/36996, 2009, A2, . Location in patent: Page/Page column 111-112

4
[ 67-56-1 ]
[ 56055-54-0 ]
[ 201230-82-2 ]
[ 51269-81-9 ]
[ 220656-93-9 ]
[ 106014-21-5 ]

Reference： [1] Tetrahedron, 1999, vol. 55, # 2, p. 393 - 404

5
[ 100-26-5 ]
[ 106014-21-5 ]

Reference： [1] Organic Letters, 2004, vol. 6, # 1, p. 3 - 5

[ 106014-21-5 ] Synthesis Path-Downstream 1~10

1
[ 67-56-1 ]
[ 56055-54-0 ]
[ 201230-82-2 ]
[ 51269-81-9 ]
[ 220656-93-9 ]
[ 106014-21-5 ]
trimethyl pyridine-2,3,5-tricarboxylate [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 393 - 404

2
[ 32658-54-1 ]
[ 67-56-1 ]
[ 106014-21-5 ]

Yield	Reaction Conditions	Operation in experiment
		Pyridine-2,5-dicarboxylic acid (10.0 g, 60.0 mmol) was suspended in 300 mL 0.2% (w/w) aq. Na2WO4 (0.6 g). To this solution was added H2O2 in water (30% w/w, 34 mL, 315 mmol). The resulting mixture was stirred and heated at 80-850C for 10 hours. The resulting solid was collected by filtration and washed with cold water. Drying the material under high vacuum <n="113"/>overnight yielded pyridine-2,5-dicarboxylic a lambdaf-oxide, which was used in the next step without further purification.To a solution of thionyl chloride (17.4 mL, 240 mmol) in DCM (500 mL) was addedDMF (5 mL) at O0C. Pyridine-2,5-dicarboxylic acid N-oxide from the first step was added into this mixture portionwise. The resulting mixture was heated at 650C for 2 hours. The reaction was cooled to RT then placed in an ice-bath. The reaction was quenched with methanol (100 mL) slowly at 0 0C. The solvent was removed in vacuo and the crude product was partitioned between DCM (200 mL) and aq. NaHCtheta3 (sat. 100 mL). The organic layer was separated and the aqueous layer was extracted with additional DCM (2 x 200 mL). The combined organic layer was dried (Na2SO4), filtered and the solvent was removed in vacuo.Purification of the crude oil through a short plug of silica gel using hexane/ethyl acetate (4:1) afforded dimethyl 3-chloropyridine-2,5-dicarboxylate. GC/MS (m/z): 229.0

Reference： [1]Organic Letters,2004,vol. 6,p. 3 - 5
[2]Patent: WO2009/36996,2009,A2 .Location in patent: Page/Page column 111-112

3
[ 64-17-5 ]
[ 220465-43-0 ]
[ 106014-21-5 ]
[ 653573-24-1 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3 - 5

4
[ 100-26-5 ]
[ 106014-21-5 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3 - 5

5
[ 106014-21-5 ]
[ 653573-29-6 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3 - 5

6
[ 106014-21-5 ]
[ 653573-28-5 ]

Reference： [1]Organic Letters,2004,vol. 6,p. 3 - 5

Yield	Reaction Conditions	Operation in experiment
		b Dimethyl 3-chloropyridine-2,5-dicarboxylate 17 ml of thionyl chloride, 35 ml of anhydrous chloroform and 1.5 ml of N,N-dimethylformamide were heated to 60 C. with stirring and 7.5 g of the above product were added in portions at this temperature. The mixture was then stirred at 60 C. for a further 60 min, the solvent and excess reagent were distilled off in vacuo after cooling, the residue was treated with dichloromethane and the N,N-dimethylformamideHCl complex was filtered off with suction and washed with dichloromethane. About 15 ml of triethylamine and 10 ml of methanol were added to the mother liquor with cooling and the mixture was stirred for 30 min. After evaporating in vacuo, the residue was dissolved in 50 ml of water and extracted 3with dichloromethane, the organic phase was dried and concentrated, and the residue was chromatographed on silica gel using n-heptane and n-heptane:ethyl acetate (3:1). 5.3 g of product were crystallized from appropriate fractions using petroleum ether, m.p. 36-38 C.
		b Dimethyl 3-chloropyridine-2,5-dicarboxylate 17 ml of thionyl chloride, 35 ml of anhydrous chloroform and 1.5 ml of N,N-dimethylformamide were heated to 60 C., while stirring, and 7.5 g of the above product were then added in portions at this temperature. The mixture was then stirred at 60 C. for a further 60 minutes, and, after cooling, the solvent and excess reagent were distilled off in vacuo; dichloromethane was added to the residue, and the N,N-dimethylformamide*HCl complex was filtered off with suction and washed with dichloromethane. Approximately 15 ml of triethylamine and 10 ml of methanol were added, While cooling, to the mother liquor and the mixture was stirred for 30 minutes. After concentrating by evaporation in vacuo, the residue was dissolved in 50 ml of water and this mixture was then extracted 3 x with dichloromethane; the organic phase was dried and concentrated, and the residue was chromatographed on silica gel using n-heptane and n-heptane:ethyl acetate (3:1). 5.3 g of product were crystallized, using petroleum ether, from appropriate fractions, m.p. 36 to 38 C.
		Example 4 Preparation of dimethyl 3-chloro-2,5-pyridinedicarboxylate Example 2 was repeated, except that the 2,3-dichloro-5-(methoxymethyl)pyridine was replaced by the same molar amount of methyl 2,3-dichloro-5-pyridinecarboxylate. After a reaction time of 6 hours at a bath temperature of 160 C., 1.20 g (73 percent) of a yellow product was obtained. Other data concerning the product was: m.p.: 35.5-36 C.

8
[ 106014-21-5 ]
[ 1134777-22-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tetrahydroborate; calcium chloride; In tetrahydrofuran; methanol; at 0℃; for 3h;	To a solution of <strong>[106014-21-5]dimethyl 3-chloropyridine-2,5-dicarboxylate</strong> (1.0 g, 4.4 mmol) in THF(10 mL) and MeOH (20 mL) was added powdered calcium chloride (3.9 g, 35 mmol). The suspension was cooled to 00C and sodium borohydride (416 mg, 11.0 mmol) was added portionwise. The resulting mixture was stirred for 3 h at 00C and poured into ice-water (200 mL), and extracted with DCM (2 x 100 mL). The combined organic layers were dried (Na2SO4), filtered and the solvent was removed in vacuo to yield methyl 5-chloro-6- (hydroxymethyl)nicotinate which was used in the next step without further purification. GC/MS (m/z): 201.0

Reference： [1]Patent: WO2009/36996,2009,A2 .Location in patent: Page/Page column 112

9
[ 106-95-6 ]
[ 106014-21-5 ]
[ 1309790-91-7 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 3174 - 3177

10
[ 96-43-5 ]
[ 106014-21-5 ]
[ 1333434-95-9 ]

Reference： [1]Angewandte Chemie - International Edition,2011,vol. 50,p. 7290 - 7294

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Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Acyl Group Substitution • Addition of a Hydrogen Halide to an Internal Alkyne • Alcohols Convert Acyl Chlorides into Esters • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcoholysis of Anhydrides • Alkyl Halide Occurrence • Alkylation of an Alkynyl Anion • Amines Convert Esters into Amides • An Alkane are Prepared from an Haloalkane • Bouveault-Blanc Reduction • Catalytic Hydrogenation • Chichibabin Reaction • Chloroalkane Synthesis with SOCI2 • Claisen Condensations Produce β-Dicarbonyl Compounds • Claisen Condensations Produce β-Dicarbonyl Compounds • Complex Metal Hydride Reductions • Convert Esters into Aldehydes Using a Milder Reducing Agent • Convert Haloalkanes into Alcohols by SN2 • Decarboxylation of 3-Ketoacids Yields Ketones • Deprotection of Cbz-Amino Acids • Ester Cleavage • Ester Hydrolysis • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Grignard Reaction • Grignard Reagents Transform Esters into Alcohols • Halogenation of Alkenes • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Ketones Undergo Mixed Claisen Reactions to Form β-Dicarbonyl Compounds • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Methylation of Ammonia • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions with Organometallic Reagents • Reduction of an Ester to an Alcohol • Reduction of an Ester to an Aldehyde • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • Transesterification

Historical Records

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[ 106014-21-5 ]

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Ghs Precautionary Statements

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Code	Phrase
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P102	Keep out of reach of children.
P103	Read label before use
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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.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P251	Pressurized container: Do not pierce or burn, even after use.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
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.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
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:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
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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.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
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.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
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P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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P406	Store in corrosive resistant/ container with a resistant inner liner.
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P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
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P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
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Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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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
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
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
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
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. 106014-21-5 ] {[proInfo.proName]}

Quality Control of [ 106014-21-5 ]

Related Doc. of [ 106014-21-5 ]

Product Details of [ 106014-21-5 ]

Calculated chemistry of [ 106014-21-5 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 106014-21-5 ]

Application In Synthesis of [ 106014-21-5 ]

[ 106014-21-5 ] Synthesis Path-Upstream 1~5

[ 106014-21-5 ] Synthesis Path-Downstream 1~10

Technical Information

Related Functional Groups of [ 106014-21-5 ]

Chlorides

Esters

Related Parent Nucleus of [ 106014-21-5 ]

Pyridines

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 106014-21-5 ]

Related Parent Nucleus of
[ 106014-21-5 ]