[ CAS No. 166247-63-8 ] {[proInfo.proName]}

Name: 166247-63-8|(2R,3S,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol|98%
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3d Animation Molecule Structure of 166247-63-8

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Quality Control of [ 166247-63-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 166247-63-8 ]

Product Details of [ 166247-63-8 ]

CAS No. :	166247-63-8	MDL No. :	MFCD07778650
Formula :	C₁₁H₁₃IN₄O₃	Boiling Point :	-
Linear Structure Formula :	HOCH₂C₄H₅O(OH)C₆H₂N₃(NH₂)I	InChI Key :	LIIIRHQRQZIIRT-XLPZGREQSA-N
M.W :	376.15	Pubchem ID :	15289165
Synonyms :		Chemical Name :	(2R,3S,5R)-5-(4-Amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

Calculated chemistry of [ 166247-63-8 ] Expand+

Physicochemical Properties

Num. heavy atoms :	19
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.45
Num. rotatable bonds :	2
Num. H-bond acceptors :	5.0
Num. H-bond donors :	3.0
Molar Refractivity :	76.43
TPSA :	106.42 Å²

Pharmacokinetics

GI absorption :	High
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) :	-8.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.48
Log Po/w (XLOGP3) :	0.28
Log Po/w (WLOGP) :	-0.06
Log Po/w (MLOGP) :	0.36
Log Po/w (SILICOS-IT) :	-0.01
Consensus Log Po/w :	0.41

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.57
Solubility :	1.02 mg/ml ; 0.00271 mol/l
Class :	Soluble
Log S (Ali) :	-2.08
Solubility :	3.15 mg/ml ; 0.00838 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-1.66
Solubility :	8.25 mg/ml ; 0.0219 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	3.76

Safety of [ 166247-63-8 ]

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:

Applications of [ 166247-63-8 ]

7-Deaza-2'-deoxy-7-iodoadenosine(CAS: 166247-63-8 ) is an oligonucleotide modified with 7-Deazaadenine.

Application In Synthesis of [ 166247-63-8 ]

* 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 [ 166247-63-8 ]
Downstream synthetic route of [ 166247-63-8 ]

[ 166247-63-8 ] Synthesis Path-Upstream 1~4

1
[ 178420-94-5 ]
[ 166247-63-8 ]

Reference： [1] Journal of the Chemical Society. Perkin Transactions 2, 1996, vol. 0, # 11, p. 2373 - 2376
[2] Synthesis, 1996, # 6, p. 726 - 730
[3] Patent: US8853373, 2014, B2, . Location in patent: Page/Page column 16
[4] Patent: WO2015/143712, 2015, A1, . Location in patent: Page/Page column 54; 55; 56

2
[ 178995-71-6 ]
[ 166247-63-8 ]

Reference： [1] Synthesis, 1996, # 6, p. 726 - 730

3
[ 123148-78-7 ]
[ 166247-63-8 ]

Reference： [1] Synthesis, 1996, # 6, p. 726 - 730

4
[ 4330-21-6 ]
[ 166247-63-8 ]

Reference： [1] Synthesis, 1996, # 6, p. 726 - 730

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Isomers

Technical Information

• Acid-Catalyzed α -Halogenation of Ketones • Alcohols from Haloalkanes by Acetate Substitution-Hydrolysis • Alcohols React with PX3 • Alkyl Halide Occurrence • Chichibabin Reaction • Convert Aldonic Acid into the Lower Aldose by Oxidative Decarboxylation • Convert Haloalkanes into Alcohols by SN2 • Friedel-Crafts Alkylation of Benzene with Haloalkanes • General Reactivity • Hantzsch Pyridine Synthesis • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Methylation of Ammonia • Preparation of Amines • Pyridines React with Grignard or Organolithium Reagents • Pyrroles, Furans, and Thiophenes are Prepared from γ-Dicarbonyl Compounds • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

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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.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
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.
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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:
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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
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P331	Do NOT induce vomiting.
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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.
P381	Eliminate all ignition sources if safe to do so.
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
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P411 + P235	Keep cool.
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P501	Dispose of contents/container to ...
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Yield	Reaction Conditions	Operation in experiment
	With ethanol; ammonia; at 65℃; for 20h;	The target substance 3 (500 mg, 0.791 mmol, F.W. 631.85) was suspended in a saturated ammonium ethanol solution. Next, the mixture was stirred in a pressure-resistant vessel at65 C. for 20 hours, and the reaction solution was distilled away under reduced pressure. A residue was dissolved in methanol (30 mL), and saturated aqueous ammonia (30 mL) was added thereto. The mixture was stirred for 5 hours, and the reaction solution was distilled away under reduced pres55 sure. Then, a residue was dissolved in a small amount ofmethanol, and was recrystallized with hexane. The recrystallized product was subjected to suction filtration to yield target substance 4.
	With ammonia; In isopropyl alcohol; at -50 - 90℃; for 48h;	Step 3: Synthesis of (2/f,35,5/f)-5-(4-amino-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(hydroxymethyl)tetrahydrofuran-3-o(2R,3^5R)-5-(4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-2-(((4-methylbenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-methylbenzoate (12 g, 18.99 mmol) was added to a stirred, cooled -50 C mixture of ammonia (120 ml, 240 mmol) in 2-Propanol (30 mL) and the mixture was stirred at 90 C for 48 hours. The solvent was evaporated under reduce pressure. The residue was purified by column chromatography on silica gel 100-200, eluting with DCM / MeOH (10/1) to give the title compound. LC-MS: (ES, m/z): 377.0[M+H]+. 1H- MR: (300MHz, CD3SOCD3, ppm): 8.10 (s, 1H), 7.81 (s, 1H), 6.79 (brs, 2H), 6.79-6.51 (dd, J= 8.1 Hz, 3 Hz, 1H), 5.27 (d, J= 3.9 Hz, 1H), 5.05 (t, J= 5.4 Hz, 1H), 4.33 (brs, 1H), 3.81 (brs, 1H), 3.60-3.46 (m, 2H), 2.51-2.44 (m, 1H), 2.19-2.10 (m, 1H)

Yield	Reaction Conditions	Operation in experiment
95%		To a suspension of 7-deaza-7-iodo-2'-deoxyadenosine (1 g, 2.65 mmol) and CuI (100 mg, 0.53 mmol) in dry DMF (20 ml) was added triethylamine (740 mul, 5.3 mmol). After stirring for 5 min trifluoro-N-prop-2-ynyl-acetamide (1.2 g, 7.95 mmol) and Pd(PPh3)4 (308 mg, 0.26 mmol) were added to the mixture and the reaction was stirred at room temperature in the dark for 16 h. MeOH (40 ml) and bicarbonate dowex was added to the reaction mixture and stirred for 45 min.The mixture was filtered. The filtrate washed with MeOH and the solvent was removed under vacuum. The crude mixture was purified by chromatography on silica (EtOAc to EtOAc: MeOH 95:20) to give slightly yellow powder (25) (1.0 g, 95 %).1H NMR (d6 DMSO) delta 2.11-2.19 (m, 1H, H-2?), 2.40-2.46 (m, 1H, H-2?), 3.44-3.58 (m, 2H, H-5?), 3.80(m, 1H, H-4?), 4.29 (m, 3H, H-3?, CH2N), 5.07 (t, J = 5.5 Hz, 1H, OH), 5.26 (d, J = 4.0 Hz, 1H, OH), 6.45 (dd, J = 6.1, 8.1Hz, 1H, H-1?), 7.74 (s, 1H, H-8), 8.09 (s, 1H, H-2), 10.09 (t, J = 5.3 Hz, 1H, NH).
92%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	DA-I7-Deaza-7-iodo-2'-deoxyadenosine (0.35 mmol, 132 mg) was added to a one-necked flask and 5 mg of CuI (25.2 mumol) and 10 mg of Pd (PPh3) 4 The reaction flask, vacuum, nitrogen protection, aluminum foil wrapped,Add 1.5ml DMF, dissolved with stirring, add 0.1ml TEA,Weigh compound F2 (127mg, 0.84mmol) dissolved in 1ml DMF was added to the above reaction flask, stirred at room temperature,TLC tracks the progress of the reaction. After the reaction was completed, the solvent was spun off,Column chromatography [V (DCM): V (MeOH) = 10: 1] gave 129 mg of dA (AP3) in 92% yield.
	With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere; Darkness;	0.5 mmol of dA-I was added with 2.5 ml of DMF to a single-mouth bottle. Then, 8.9 mg of Cul and 22.7 mg of Pd(PPh3)4 were weighed into a reaction flask, vacuumed, protected with nitrogen, wrapped in an aluminum foil. After stirring, 0.23 ml of TEA and 1.8 mmol of trifluoroethylpropynylamine was dissolved in DMF, and then added to the above reaction flask, and stirred at room temperature, and allowed to react overnight. After completion of the reaction, the solvent was evaporated under reduced pressure, direct column chromatography, dichloromethane and methanol in a 20: 1 volume ratio mixture as eluent, to obtain the final dA-F3.

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. 166247-63-8 ] {[proInfo.proName]}

Quality Control of [ 166247-63-8 ]

Related Doc. of [ 166247-63-8 ]

Product Details of [ 166247-63-8 ]

Calculated chemistry of [ 166247-63-8 ] Expand+

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 166247-63-8 ]

Applications of [ 166247-63-8 ]

Application In Synthesis of [ 166247-63-8 ]

[ 166247-63-8 ] Synthesis Path-Upstream 1~4

[ 166247-63-8 ] Synthesis Path-Downstream 1~109

Technical Information

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

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