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3680-69-1

Basic Information
CAS No.: 3680-69-1
Name: 7H-Pyrrolo[2,3-d]pyrimidine,4-chloro-
Article Data: 55
Cas Database
Molecular Structure:
Molecular Structure of 3680-69-1 (7H-Pyrrolo[2,3-d]pyrimidine,4-chloro-)
Formula: C6H4ClN3
Molecular Weight: 153.571
Synonyms: 1H-Pyrrolo[2,3-d]pyrimidine,4-chloro- (7CI,9CI);4-Chloro-7H-pyrrolo[2,3-d]pyrimidine;6-Chloro-7-deazapurine;NSC 64952;7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-;4-Chloropyrrolo[2,3-d]pyrimidine;
EINECS: 628-079-2
Density: 1.531 g/cm3
Melting Point: 183-184 °C
Boiling Point: 325.9 °C at 760 mmHg
Flash Point: 180.7 °C
Solubility: N/A
Appearance: light brown to brown crystalline powder
Hazard Symbols: IrritantXi,ToxicT,HarmfulXn
Risk Codes: 36/37/38-25-20/21/22
Safety: 26-37-45-36
Transport Information: UN 2811 6.1/PG 3
PSA: 41.57000
LogP: 1.61130
Synthetic route
3680-71-5

Allopurinol

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With chlorine In 1-methyl-pyrrolidin-2-one; toluene at 160 - 180℃; Temperature;95%
With 1,2,3-trichloropropane; chlorine In 1-methyl-pyrrolidin-2-one; toluene Reflux;95%
With dmap; bis(trichloromethyl) carbonate In chlorobenzene at 50 - 60℃; for 6h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;94.2%

6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 7.5h; Reflux;94%
Stage #1: 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine With hydrogenchloride; water In tetrahydrofuran at 20℃; Reflux;
Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1h;
With hydrogenchloride In tetrahydrofuran; water for 7.5h; Reflux;54.5 g
3680-71-5

7-deazahypoxanthine

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With trichlorophosphate for 2h; Reflux;93%
With trichlorophosphate92%
With trichlorophosphate for 4h; Reflux;91%

4-hydroxypyrrolo[2,3-D]pyrimidine

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With trichlorophosphate for 3h; Reflux;93%

4-amino-6-chloro-5-(2,2-diethoxyethyl)pyrimidine

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With hydrogenchloride In water at 50℃; for 4h; Reagent/catalyst;92%
With hydrogenchloride; water In Petroleum ether at 50℃; for 4h;91%

4-amino-6-chloropyrimidine-5-acetaldehyde

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With hydrogenchloride In methanol; water at 50℃; for 3h; Concentration; Temperature; Industrial scale;91.4%
With hydrogenchloride In methanol; water at 50 - 60℃; for 3h;82%
With acetic acid at 20℃; for 14h;26.1 g

1,1-dichloro-2-cyano-4-methoxy-1,3-butadiene

6313-33-3

formamidine hydrochloride

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With sodium methylate In methanol at 25 - 70℃; for 10h;91%

1,1-dichloro-2-cyano-4-methoxy-1,3-butadiene

3473-63-0

formamidine acetic acid

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With sodium methylate In methanol at 30 - 70℃; for 10h;90.2%
123148-78-7

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With potassium benzo[d][1,3]dioxol-5-yltrifluoroborate; PdCl2(1,1'-bis(diphenylphosphino)ferrocene); triethylamine In ethanol; dichloromethane for 19h; Reagent/catalyst; Reflux;90%
3680-71-5

1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

3680-69-1

4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions
ConditionsYield
With trichlorophosphate at 100℃; for 5h;65.7%
With trichlorophosphate for 5h; Reflux;54%
With trichlorophosphate for 5h; Reflux;54%
With trichlorophosphate for 5h; Reflux;54%
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Chemistry

IUPAC Name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
Systematic of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS NO.3680-69-1): 4-Chloropyrrolo(2,3-d)pyrimidine ; BRN 0607871 ; NSC 64952 ; 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-
CAS NO: 3680-69-1
Classification Code: Drug / Therapeutic Agent
Molecular Formula of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS NO.3680-69-1): C6H4ClN3
Molecular Weight: 153.5691
Molecular Structure:

ProductCategories: Heterocycles ; Heterocycles series ; Halides ; Pyrimidine ; Heterocyclic Compounds ; Biochemistry ; Nucleobases and their analogs ; Nucleosides, Nucleotides & Related Reagents ; CHIRAL CHEMICALS ; Naphthyridine,Quinoline ; Bases & Related Reagents ; Intermediates ; Nucleotides ; Fused Ring Systems ; Heterocyclic Building Blocks
Melting Point: 183-184°C
Polar Surface Area: 30.71 Å2
Index of Refraction: 1.72
Molar Refractivity: 39.6 cm3
Molar Volume: 100.2 cm3
Surface Tension: 74.7 dyne/cm
Density of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS NO.3680-69-1): 1.531 g/cm3
Flash Point: 180.7 °C
Enthalpy of Vaporization: 54.55 kJ/mol
Boiling Point: 325.9 °C at 760 mmHg
Vapour Pressure: 0.000424 mmHg at 25°C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 297mg/kg (297mg/kg)   Gann. Japanese Journal of Cancer Research. Vol. 56, Pg. 219, 1965.

Safety Profile

Hazard Codes: IrritantXi,ToxicT,Xn
Risk Statements: 36/37/38-25-20/21/22 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R25: Toxic if swallowed. 
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-37-45-36 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37: Wear suitable gloves. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
RTECS: UY9360000
HazardClass: IRRITANT